WO2012017955A1 - 接着剤層付き半導体ウェハの製造方法、感光性接着剤及び半導体装置 - Google Patents
接着剤層付き半導体ウェハの製造方法、感光性接着剤及び半導体装置 Download PDFInfo
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- WO2012017955A1 WO2012017955A1 PCT/JP2011/067494 JP2011067494W WO2012017955A1 WO 2012017955 A1 WO2012017955 A1 WO 2012017955A1 JP 2011067494 W JP2011067494 W JP 2011067494W WO 2012017955 A1 WO2012017955 A1 WO 2012017955A1
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- photosensitive adhesive
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- KNDQHSIWLOJIGP-UHFFFAOYSA-N O=C(C1C2C3C=CC1C3)OC2=O Chemical compound O=C(C1C2C3C=CC1C3)OC2=O KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N OC(c(cc1C(O2)=O)ccc1C2=O)=O Chemical compound OC(c(cc1C(O2)=O)ccc1C2=O)=O SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- PXHIYFMTRHEUHZ-UHFFFAOYSA-N Oc(cc1C(O2)=O)ccc1C2=O Chemical compound Oc(cc1C(O2)=O)ccc1C2=O PXHIYFMTRHEUHZ-UHFFFAOYSA-N 0.000 description 1
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/52—Mounting semiconductor bodies in containers
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
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- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/27—Manufacturing methods
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- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
- H01L2224/321—Disposition
- H01L2224/32135—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip
- H01L2224/32145—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip the bodies being stacked
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- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
- H01L2224/321—Disposition
- H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/32225—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
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- H01L2224/42—Wire connectors; Manufacturing methods related thereto
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- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/48225—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
- H01L2224/48227—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation connecting the wire to a bond pad of the item
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- H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
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- H01L2924/1531—Connection portion the connection portion being formed only on the surface of the substrate opposite to the die mounting surface
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Definitions
- the present invention relates to a method for manufacturing a semiconductor wafer with an adhesive layer, a photosensitive adhesive, and a semiconductor device. More specifically, a photosensitive adhesive for die bonding used as a bonding material (die bonding material) when laminating semiconductor elements such as IC and LSI and a support member such as a lead frame or an insulating support substrate, or semiconductor chips.
- a photosensitive adhesive for die bonding used as a bonding material (die bonding material) when laminating semiconductor elements such as IC and LSI and a support member such as a lead frame or an insulating support substrate, or semiconductor chips.
- the present invention relates to a semiconductor wafer manufacturing method and a semiconductor device using the same.
- an adhesive film using a specific polyimide resin, a conductive filler or an inorganic filler on a specific polyimide resin Added die bonding adhesive films are known.
- wafer a semiconductor wafer
- the thickness of the wafer tends to be reduced.
- a process using an adhesive film or a process of applying a die bonding adhesive to a semiconductor wafer by a spin coating method is applied.
- an adhesive film is laminated on the entire surface of a semiconductor wafer, a support film for dicing is further laminated, and a semiconductor chip on which the adhesive film is laminated is separated into a semiconductor substrate or a semiconductor chip by a dicing process.
- the method of sticking to is mentioned.
- a spin coating method in which a liquid adhesive on a semiconductor wafer is applied to the entire surface by high-speed rotation is also widely known.
- the strength of the wafer tends to decrease. Therefore, after the wafer back grinding step, it is desirable to apply a die bonding adhesive while the back grind tape is bonded to form a B stage.
- JP 2008-98213 A Japanese Patent Publication No. 5-54262
- the adhesive film is likely to be wasted at portions other than the wafer in the process of laminating the adhesive film onto the wafer. Even in the case of using the spin coating method, it is necessary to supply and discard the adhesive on the semiconductor wafer until a uniform adhesive layer is formed, and the adhesive is likely to be wasted.
- the heat resistance of the back grind tape is about 80 ° C. to 100 ° C., and the back grind tape shrinks when heated to 100 ° C. or higher. Shrinkage of the back grind tape can cause warping of the semiconductor wafer. Even when heating at 80 ° C. or lower, the semiconductor wafer tends to warp during cooling after heating due to the difference between the thermal expansion coefficient of the back grind tape and the thermal expansion coefficient of the semiconductor wafer.
- the present invention has been made in view of the above circumstances, and is capable of forming an adhesive layer on a semiconductor wafer with a uniform film thickness and less waste of the adhesive, and for the B-stage of the adhesive layer.
- the manufacturing method of the semiconductor wafer with an adhesive layer which can avoid the curvature of the semiconductor wafer resulting from heating, the photosensitive adhesive used for the manufacturing method, and the semiconductor wafer with an adhesive layer which can be manufactured by the manufacturing method
- An object of the present invention is to provide a semiconductor device and a photosensitive adhesive for screen printing.
- the present invention includes a step of applying a photosensitive adhesive to a whole surface of a semiconductor wafer by a screen printing method to form a photosensitive adhesive layer, and a step of exposing the photosensitive adhesive layer to a B-stage by exposure.
- a method for manufacturing a semiconductor wafer with an adhesive layer is provided.
- an adhesive layer can be formed on a semiconductor wafer with a uniform film thickness and less waste of the adhesive, and also due to heating for B-stage formation of the adhesive layer. Semiconductor wafer warpage can be avoided.
- the photosensitive adhesive can contain a thermosetting resin, a radiation polymerizable compound, and a photopolymerization initiator.
- the photosensitive adhesive may further contain a thermosetting initiator.
- the viscosity of the photosensitive adhesive at 25 ° C. is 1 to 100 Pa ⁇ s, and the thixotropic index of the photosensitive adhesive may be 1.0 to 3.0.
- the photosensitive adhesive according to the present invention contains a thermosetting resin, a radiation polymerizable compound and a photopolymerization initiator, and is used for forming a photosensitive adhesive layer in the above production method.
- the present invention also provides a process of obtaining a semiconductor chip with an adhesive layer by separating the semiconductor wafer with an adhesive layer obtained by the manufacturing method according to the present invention, and supporting the semiconductor chip of the semiconductor wafer with an adhesive layer. And a step of adhering to a member or another semiconductor chip.
- the present invention contains a thermosetting resin, a radiation polymerizable compound and a photopolymerization initiator, has a viscosity at 25 ° C. of 1 to 100 Pa ⁇ s, and a thixotropic index of 1.0 to 3.0.
- a photosensitive adhesive for screen printing is provided.
- an adhesive layer can be formed on a semiconductor wafer with a uniform film thickness and less waste of the adhesive, and the warp of the semiconductor wafer due to heating for B-stage of the adhesive layer is caused.
- a method for manufacturing a semiconductor wafer with an adhesive layer a photosensitive adhesive used in the manufacturing method, a semiconductor device including the semiconductor wafer that can be manufactured by the manufacturing method, and a photosensitive adhesive for screen printing.
- the method for manufacturing a semiconductor device includes a step of applying a photosensitive adhesive to a whole surface of a semiconductor wafer by a screen printing method to form a photosensitive adhesive layer (photosensitive adhesive layer forming step). ), And a step of B-stage the photosensitive adhesive layer by exposure (B-stage forming step), and a step of cutting the semiconductor wafer together with the B-staged photosensitive adhesive layer (dicing step).
- a semiconductor wafer 6 shown in FIG. 1 is used to form semiconductor chips 13a and 13b (FIG. 6) incorporated in a semiconductor package (semiconductor device) (FIG. 6).
- the semiconductor wafer 6 is typically a silicon wafer.
- a circuit may already be formed in the semiconductor wafer 6 by a previous process.
- the photosensitive adhesive layer forming step for example, as shown in FIG. 1, the photosensitive adhesive 5 is applied to the surface (back surface) opposite to the surface on which the circuit of the semiconductor wafer 6 is formed by screen printing. Apply (print). As a result, a photosensitive adhesive layer 7 having a uniform thickness is formed on the back surface of the semiconductor wafer 6 as shown in FIG.
- the screen printing method generally includes the following two methods.
- One is a method using a so-called metal printing plate in which a patterned opening is provided on a flat metal plate.
- a metal printing plate is placed on an object to be printed, and ink is applied by sweeping ink mounted on the metal printing plate with a metal plate called a squeegee. By this step, the ink is applied in the shape of the opening pattern provided on the metal printing plate.
- the adhesive in any printing method, can be selectively applied only to a desired position and region, so that the waste of the adhesive can be reduced and the material yield is excellent.
- the mesh yarn in the opening also functions as a support member even at the center of the squeegee, so that the squeegee is not strongly pushed into the opening. For this reason, the film thickness does not decrease even in the center of the squeegee, and a uniform photosensitive adhesive layer can be obtained.
- a method using a mesh printing plate is preferable from the viewpoint of providing a photosensitive adhesive layer having a uniform film thickness over a relatively wide range of the entire wafer surface.
- the photosensitive adhesive layer 7 is a photosensitive adhesive layer having adhesion to an adherend after being B-staged by exposure.
- the applied photosensitive adhesive layer 7 is irradiated with visible light or ultraviolet rays by an exposure device, and the photosensitive adhesive 5 constituting the photosensitive adhesive layer 7 is made into a B-stage.
- a polymerization reaction by the photopolymerization initiator and the radiation polymerizable compound contained in the photosensitive adhesive 5 proceeds, and the B-staged photosensitive adhesive layer 8 has appropriate tackiness and adhesiveness.
- the photosensitive adhesive layer 8 is fixed to the semiconductor wafer 6.
- the photosensitive adhesive layer 7 is B-staged not by heating but by exposure, so that the photosensitive adhesive 5 can be applied and photosensitive while the back grind tape is still bonded to the semiconductor wafer 6.
- the adhesive adhesive layer 7 can be made into a B-stage.
- the exposure is preferably performed in a nitrogen atmosphere or under vacuum, or in a state where a transparent cover film is laminated on the photosensitive adhesive layer 7 from the viewpoint of avoiding the inhibition of the photopolymerization reaction due to oxygen.
- the photosensitive adhesive layer 8 that has been B-staged by exposure is divided into individual pieces by dicing, and appropriate adhesiveness that enables peeling from the support during dicing, and a semiconductor chip and It has adhesiveness to an adherend such as a glass substrate. Details of the photosensitive adhesive layer 8 having such a function will be described later.
- the surface tack force at 30 ° C. exceeds 200 gf / cm 2 , the adhesiveness of the surface of the photosensitive adhesive layer 8 at room temperature increases, and the handleability tends to decrease. Furthermore, the peelability from the dicing film after dicing tends to decrease, and the pick-up property tends to decrease. Further, when the surface tack force at 30 ° C. is 1 gf / cm 2 or less, the tackiness of the photosensitive adhesive is lowered, and water penetrates into the interface between the photosensitive adhesive and the dicing film during dicing, and the chip jumps. Tend to occur.
- the surface tack force at 120 ° C. of the exposed photosensitive adhesive layer 8 is 200 gf / cm 2 or more.
- the thermocompression bonding property is impaired, voids are generated during thermocompression bonding, and the thermocompression bonding temperature tends to increase.
- the surface tack force at 120 ° C. is 500 gf / cm 2 or more, the photosensitive adhesive excessively spreads during thermocompression bonding, and the photosensitive adhesive tends to protrude from the side surface of the chip.
- the surface tack force is a value measured as follows. Photosensitive adhesive was applied onto a silicon wafer by screen printing, and the resulting coating film was subjected to nitrogen by a high-precision parallel exposure machine (“EXM-1172-B- ⁇ ” (trade name), manufactured by Oak Seisakusho). Exposure is performed at 1000 mJ / cm 2 in an atmosphere. Then, using a probe tacking tester manufactured by Reska, 30 ° C. and 120 ° C. under conditions of probe diameter: 5.1 mm, peeling speed: 10 mm / s, contact load: 100 gf / cm 2 , contact time: 1 s. The tack force on the surface of the photosensitive adhesive layer 8 is measured. A parallel exposure machine (“ML-210FM Mask Aligner” (trade name) manufactured by Luminous Co., Ltd.) may be used instead of the high-precision parallel exposure machine.
- ML-210FM Mask Aligner (trade name) manufactured by Luminous Co., Ltd.
- the semiconductor wafer 20 with the adhesive layer having the photosensitive adhesive layer 8 formed on the semiconductor wafer 6 and the back surface thereof is diced from the wafer side, and the separated semiconductor chip 11 is manufactured (FIG. 4). ). That is, the semiconductor wafer 6 is cut into a plurality of semiconductor chips 11 by cutting the semiconductor wafer 6 with a dicing machine. Prior to this dicing step, it is preferable that the dicing film 10 is attached to the back surface of the semiconductor wafer 6 on which the photosensitive adhesive layer 8 is formed. Affixing may be performed while heating if necessary. For example, it is preferably carried out using a dicing blade 12 with the dicing film 10 fixed to the frame (wafer ring) 9 (FIG. 3) (FIG. 4). The separated semiconductor chip 11 with the photosensitive adhesive layer is picked up using a die bonding apparatus or the like (FIG. 5).
- the semiconductor chip 13a obtained by the dicing process is arranged on a support member 14 prepared separately.
- a semiconductor chip 13 b different from the semiconductor chip 13 a is disposed on the semiconductor chip 13 a that is bonded to the support member 14 in advance.
- the photosensitive adhesive layers 16 and 17 are thermocompression bonded to bond the semiconductor chip 13a and the support member 14, and the semiconductor chip 13b and the semiconductor chip 13a, and the semiconductor chips 13a and 13b are connected to the support member 14 or the semiconductor. It is bonded and fixed to the chip 13a.
- the photosensitive adhesive 5 for bonding the semiconductor chip 13a and the support member 14 or the semiconductor chips 13a and 13b is applied only on the semiconductor wafer 6 by screen printing. Is possible. Thereby, it is possible to apply a desired film thickness by changing the printing plate regardless of the composition of the photosensitive adhesive 5. Accordingly, it is possible to reduce the waste of the adhesive in the manufacturing method of the semiconductor device or the semiconductor wafer with the adhesive layer, and to apply a plurality of film thicknesses with a single adhesive.
- This photosensitive adhesive can be suitably used as the photosensitive adhesive 5 in the semiconductor device manufacturing method described above.
- the photosensitive adhesive according to this embodiment contains (A) a thermosetting resin, (B) a radiation polymerizable compound, and (C) a photopolymerization initiator.
- thermosetting resin is not particularly limited as long as it is a component composed of a reactive compound that causes a crosslinking reaction by heating.
- a reactive compound that causes a crosslinking reaction by heating For example, epoxy resin, cyanate ester resin, maleimide resin, allyl nadiimide resin, phenol Resin, urea resin, melamine resin, alkyd resin, acrylic resin, unsaturated polyester resin, diallyl phthalate resin, silicone resin, resorcinol formaldehyde resin, xylene resin, furan resin, polyurethane resin, ketone resin, triallyl cyanurate resin, polyisocyanate Resin, resin containing tris (2-hydroxyethyl) isocyanurate, resin containing triallyl trimellitate, thermosetting resin synthesized from cyclopentadiene, and thermosetting by trimerization of aromatic dicyanamide sex Butter, and the like.
- thermosetting resins are preferred in that they can have excellent adhesive strength at high temperatures in combination with polyimide resins.
- these thermosetting resins can be used individually by 1 type or in combination of 2 or more types.
- epoxy resin those containing at least two epoxy groups in the molecule are preferable, and phenol glycidyl ether type epoxy resins are more preferable from the viewpoints of thermocompression bonding, curability and cured product characteristics.
- examples of such resins include bisphenol A type (or AD type, S type, and F type) glycidyl ether, water-added bisphenol A type glycidyl ether, ethylene oxide adduct bisphenol A type glycidyl ether, and propylene oxide adduct.
- the epoxy resin it is possible to use a high-purity product in which the impurity ions, alkali metal ions, alkaline earth metal ions, halogen ions, particularly chlorine ions and hydrolyzable chlorine are reduced to 300 ppm or less, to prevent electromigration. This is preferable from the viewpoint of preventing corrosion of the metal conductor circuit.
- the amount of the thermosetting resin such as an epoxy resin is preferably 10 to 80% by mass with respect to the total amount of the photosensitive adhesive, and 20 to 60% by mass from the viewpoint of the reliability of the photosensitive adhesive. More preferred. When this amount exceeds 80% by mass, the viscosity of the photosensitive adhesive tends to increase, and the printability tends to decrease. On the other hand, when it is less than 10% by mass, there is a tendency that sufficient thermocompression bonding property and high temperature adhesiveness cannot be obtained.
- the upper limit and lower limit of the amount of the thermosetting resin are 10% by mass, 20% by mass, 33% by mass, 42.5% by mass, 60% by mass, or 80% by mass with respect to the total amount of the photosensitive adhesive. Also good.
- the thermosetting resin preferably has a 5% mass reduction temperature of 150 ° C. or higher, more preferably 180 ° C. or higher, and even more preferably 200 ° C. or higher.
- the 5% mass reduction temperature refers to a thermosetting resin using a differential thermothermogravimetric simultaneous measurement apparatus (SII Nanotechnology: TG / DTA6300), a heating rate of 10 ° C./min, and a nitrogen flow (400 ml).
- / Min is a 5% mass loss temperature when measured under.
- thermosetting resins having heat resistance examples include epoxy resins having an aromatic ring in the molecule, and in particular, trifunctional (or tetrafunctional) glycidylamine and bisphenol from the viewpoint of adhesion and heat resistance.
- A-type (or AD-type, S-type, F-type) glycidyl ether is preferably used.
- the photosensitive adhesive according to this embodiment preferably contains a thermosetting initiator (curing accelerator).
- the thermosetting initiator is not particularly limited as long as it is a compound that accelerates curing or polymerization of the epoxy resin by heating, and examples thereof include phenolic compounds, aliphatic amines, alicyclic amines, aromatic polyamines, polyamides, aliphatics.
- imidazoles are preferably used from the viewpoint of solubility and dispersibility when no solvent is contained.
- the amount of the thermosetting initiator is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the thermosetting resin such as an epoxy resin.
- imidazoles are particularly preferable from the viewpoints of adhesiveness, heat resistance, and storage stability.
- the upper limit and lower limit of the amount of the thermosetting initiator may be 0.01 parts by mass, 0.67 parts by mass, 1 part by mass or 50 parts by mass with respect to 100 parts by mass of the thermosetting resin.
- the reaction start temperature is preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and most preferably 100 ° C. or higher.
- the reaction start temperature is less than 50 ° C., the storage stability of the photosensitive adhesive is lowered, so that the viscosity of the photosensitive adhesive is increased and the film thickness tends to be difficult to control.
- the imidazoles it is preferable to use a compound having an average particle size of 10 ⁇ m or less, more preferably 8 ⁇ m or less, and most preferably 5 ⁇ m or less.
- a compound having an average particle size of 10 ⁇ m or less, more preferably 8 ⁇ m or less, and most preferably 5 ⁇ m or less.
- imidazoles having such an average particle diameter the change in the viscosity of the photosensitive adhesive can be suppressed, and the precipitation of imidazoles can be suppressed.
- a uniform film can be obtained by reducing surface irregularities.
- the outgas can be reduced because the curing of the photosensitive adhesive can be uniformly progressed during the curing.
- favorable storage stability can be obtained by using imidazole with poor solubility in an epoxy resin.
- imidazoles As imidazoles, imidazoles that are soluble in epoxy resins can also be used. By using such imidazoles, surface irregularities when a thin film of a photosensitive adhesive is formed can be further reduced.
- imidazoles include, but are not limited to, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2- Examples include phenylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole and the like.
- the photosensitive adhesive may contain a phenolic compound as a curing agent.
- a phenolic compound having at least two phenolic hydroxyl groups in the molecule is more preferable.
- examples of such compounds include phenol novolak, cresol novolak, t-butylphenol novolak, dicyclopentadiene cresol novolak, dicyclopentadienephenol novolak, xylylene-modified phenol novolak, naphthol compound, trisphenol compound, tetrakisphenol novolak, Bisphenol A novolac, poly-p-vinylphenol and phenol aralkyl resin.
- those having a number average molecular weight in the range of 400 to 4000 are preferable.
- the amount of the phenolic compound is preferably 50 to 120 parts by mass and more preferably 70 to 100 parts by mass with respect to 100 parts by mass of the thermosetting resin.
- Examples of the radiation polymerizable compound include compounds having an ethylenically unsaturated group.
- Examples of the ethylenically unsaturated group include a vinyl group, an allyl group, a propargyl group, a butenyl group, an ethynyl group, a phenylethynyl group, and a maleimide. Group, nadiimide group, (meth) acryl group and the like.
- a (meth) acryl group is preferable, and a monofunctional (meth) acrylate is preferably included. By adding monofunctional (meth) acrylate, it is possible to reduce the crosslink density of the photosensitive adhesive, especially during exposure for B-stage, and the post-exposure thermocompression, low stress and adhesiveness can be reduced. It can be in a good state.
- the 5% mass reduction temperature of the monofunctional (meth) acrylate is preferably 100 ° C. or higher, more preferably 120 ° C. or higher, still more preferably 150 ° C. or higher, and 180 ° C. or higher. Is most preferred.
- the 5% mass reduction temperature means a monofunctional (meth) acrylate using a differential thermothermal gravimetric simultaneous measurement apparatus (SII Nanotechnology: TG / DTA6300), a temperature rising rate of 10 ° C./min, and a nitrogen flow. 5% mass loss temperature when measured under (400 ml / min).
- glycidyl group-containing (meth) acrylate phenol EO modified (meth) acrylate, phenol PO modified (meth) acrylate, nonylphenol EO modified (meth) acrylate , Aromatic (meth) acrylates such as nonylphenol PO-modified (meth) acrylate, phenolic hydroxyl group-containing (meth) acrylate, hydroxyl group-containing (meth) acrylate, phenylphenol glycidyl ether (meth) acrylate, and phenoxyethyl (meth) acrylate , Imide group-containing (meth) acrylate, carboxyl group-containing (meth) acrylate, isoboronyl-containing (meth) acrylate, dicyclopentadienyl group-containing (meth) acrylate, and isoboroni (Meth) acrylate can be
- the monofunctional (meth) acrylate preferably has a urethane group, an isocyanuric group, an imide group, or a hydroxyl group from the viewpoints of adhesion to an adherend after B-stage formation, adhesion after curing, and heat resistance,
- a monofunctional (meth) acrylate having an imide group in the molecule is preferable.
- a monofunctional (meth) acrylate having an epoxy group can also be preferably used.
- the monofunctional (meth) acrylate having an epoxy group preferably has a 5% mass reduction temperature of 150 ° C. or more from the viewpoints of storage stability, adhesiveness, low outgas properties, heat resistance reliability, and moisture resistance reliability.
- the temperature is more preferably 180 ° C. or higher, and most preferably 200 ° C. or higher.
- the said heat resistance can be satisfied by using the polyfunctional epoxy resin whose 5% mass reduction
- the monofunctional (meth) acrylate having an epoxy group is not particularly limited, but in addition to glycidyl methacrylate, glycidyl acrylate, 4-hydroxybutyl acrylate glycidyl ether, 4-hydroxybutyl methacrylate glycidyl ether, functional groups that react with epoxy groups And compounds obtained by reacting a compound having an ethylenically unsaturated group with a polyfunctional epoxy resin.
- a functional group which reacts with the said epoxy group An isocyanate group, a carboxyl group, a phenolic hydroxyl group, a hydroxyl group, an acid anhydride, an amino group, a thiol group, an amide group etc. are mentioned. These compounds can be used individually by 1 type or in combination of 2 or more types.
- the monofunctional (meth) acrylate having an epoxy group is, for example, in the presence of triphenylphosphine or tetrabutylammonium bromide, a polyfunctional epoxy resin having at least two epoxy groups in one molecule, and 1 equivalent of an epoxy group. It is obtained by reacting with 0.1 to 0.9 equivalent of (meth) acrylic acid. Also, by reacting a polyfunctional isocyanate compound with a hydroxy group-containing (meth) acrylate and a hydroxy group-containing epoxy compound in the presence of dibutyltin dilaurate, or reacting a polyfunctional epoxy resin with an isocyanate group-containing (meth) acrylate. And glycidyl group-containing urethane (meth) acrylate and the like.
- the monofunctional (meth) acrylate having an epoxy group is 5% by mass from the viewpoint of storage stability, adhesiveness, low outgassing of the package during assembly heating of the semiconductor device and after assembly of the semiconductor device, heat resistance and moisture resistance.
- the decrease temperature is preferably 150 ° C. or higher in that it can suppress volatilization due to heat drying or segregation on the surface during the formation of an adhesive film (photosensitive adhesive layer), and voids, separation or adhesion due to outgassing during thermosetting. It is more preferably 180 ° C. or higher in terms of being able to suppress deterioration in properties, and even more preferably 200 ° C. or higher, and 260 ° C.
- a monofunctional (meth) acrylate having an epoxy group a compound having an aromatic ring in the molecule is preferable.
- the monofunctional (meth) acrylate having an epoxy group has a high purity in which impurity ions such as alkali metal ions, alkaline earth metal ions, halogen ions, especially chlorine ions and hydrolyzable chlorine are reduced to 1000 ppm or less. It is preferable to use a product from the viewpoint of preventing electromigration and preventing corrosion of a metal conductor circuit.
- the impurity ion concentration can be satisfied by using a polyfunctional epoxy resin with reduced alkali metal ions, alkaline earth metal ions, halogen ions, and the like as a raw material.
- the total chlorine content can be measured according to JIS K7243-3.
- the number of epoxy groups and ethylenically unsaturated groups is preferably 3 or less, respectively, and in particular, the number of ethylenically unsaturated groups is 2. It is preferable that it is one or less.
- a compound is not particularly limited, but a compound represented by the following general formula (1), (2), (3), (4) or (5) is preferably used.
- R 12 and R 16 represent a hydrogen atom or a methyl group
- R 10 , R 11 , R 13 and R 14 represent a divalent organic group
- R 15 , R 17 and R 18 represent an organic group having an epoxy group or an ethylenically unsaturated group.
- f represents an integer. f is, for example, 1 to 10.
- the amount of the monofunctional (meth) acrylate is preferably 20 to 100% by mass, more preferably 40 to 100% by mass, and more preferably 50 to 100% by mass with respect to the radiation polymerizable compound (B). Most preferably.
- the radiation polymerizable compound may contain a bifunctional or higher functional (meth) acrylate.
- acrylates are not particularly limited, but are diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane diacrylate.
- R 19 and R 20 each independently represent a hydrogen atom or a methyl group
- g and h each independently represent an integer of 1 to 20.
- the radiation polymerizable compound having a glycol skeleton represented by the general formula (6) is preferable in that it can sufficiently impart solvent resistance after curing, has low viscosity, and has a high 5% mass reduction temperature. .
- the radiation-polymerizable compound having a high functional group equivalent preferably has a polymerization functional group equivalent of 200 eq / g or more, more preferably 300 eq / g or more, and most preferably 400 eq / g or more.
- a radiation-polymerizable compound having an ether skeleton, urethane group and / or isocyanuric group having a polymerization functional group equivalent of 200 eq / g or more By using a radiation-polymerizable compound having an ether skeleton, urethane group and / or isocyanuric group having a polymerization functional group equivalent of 200 eq / g or more, the adhesiveness of the photosensitive adhesive is improved, and the stress and the warpage are reduced. It becomes possible.
- a radiation polymerizable compound having a polymerization functional group equivalent of 200 eq / g or more and a radiation polymerizable compound having a polymerization functional group equivalent of less than 200 eq / g may be used in combination.
- the amount of the (B) radiation-polymerizable compound is preferably 10 to 95% by mass with respect to the total amount of the photosensitive adhesive, and more preferably 20 to 90% by mass from the viewpoint of wetting and spreading at the time of chip pressing. Preferably, it is most preferably 40 to 90% by mass from the viewpoint of shape retention after B-stage formation.
- the component (B) is less than 10% by mass, the tack force after B-stage formation tends to increase, and when it exceeds 95% by mass, the adhesive strength after thermosetting tends to decrease.
- the upper limit and lower limit of the amount of the radiation polymerizable compound are 10% by mass, 20% by mass, 40% by mass, 56.7% by mass, 66% by mass, 90% by mass or 95% with respect to the total amount of the photosensitive adhesive. It may be mass%.
- the radiation-polymerizable compound is preferably liquid at room temperature (15 ° C. to 30 ° C.), and the viscosity is preferably 5000 mPa ⁇ s or less in consideration of the removal of the photosensitive adhesive from the mesh printing plate. When considering further flattening due to self-flow after printing, it is more preferably 3000 mPa ⁇ s or less. When the viscosity exceeds 5000 mPa ⁇ s, the viscosity of the photosensitive adhesive tends to increase and the printability tends to decrease.
- the radiation-polymerizable compound preferably has a 5% mass reduction temperature of 120 ° C. or higher, more preferably 150 ° C. or higher, and even more preferably 180 ° C. or higher.
- the 5% mass reduction temperature refers to a radiation-polymerizable compound using a differential thermothermal gravimetric simultaneous measurement apparatus (SII Nanotechnology: TG / DTA6300), a temperature rising rate of 10 ° C./min, and a nitrogen flow (400 ml).
- / Min is a 5% mass loss temperature when measured under.
- the photopolymerization initiator is preferably one having a molecular extinction coefficient of 100 ml / g ⁇ cm or more with respect to light having a wavelength of 365 nm, from the viewpoint of improving the sensitivity of photopolymerization, and 200 ml / g ⁇ cm. The above is more preferable.
- a 0.001 mass% acetonitrile solution of the sample is prepared, and the absorbance of this solution is measured using a spectrophotometer (manufactured by Hitachi High-Technologies Corporation, “U-3310” (trade name)). Is required.
- component (C) examples include 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2,2-dimethoxy-1,2-diphenylethane-1-one. 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone-1, 2,4-diethylthioxanthone, 2-ethylanthraquinone, phenanthrenequinone, etc.
- Benzyl derivatives such as aromatic ketones, benzyldimethyl ketal, 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (m-methoxyphenyl) imidazole Dimer, 2- (o-fluorophenyl) -4,5-phenylimidazole dimer, 2- o-methoxyphenyl) -4,5-diphenylimidazole dimer, 2- (p-methoxyphenyl) -4,5-diphenylimidazole dimer, 2,4-di (p-methoxyphenyl) -5-phenyl 2,4,5-triarylimidazole dimers such as imidazole dimer and 2- (2,4-dimethoxyphenyl) -4,5-diphenylimidazole dimer, 9-phenylacridine and 1,7-bis Acridine derivatives such as (9,9'-
- 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-benzyl-2-dimethylamino-in terms of solubility in a photosensitive adhesive containing no solvent 1- (4-morpholinophenyl) -butanone-1,2,2-dimethoxy-1,2-diphenylethane-1-one and 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane -1-one is preferably used.
- 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2,2 is that the photosensitive adhesive layer can be B-staged by exposure even in an air atmosphere.
- -Dimethoxy-1,2-diphenylethane-1-one and 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one are preferably used.
- the component (C) may contain a photoinitiator that exhibits a function of promoting polymerization and / or reaction of the epoxy resin by irradiation with radiation.
- a photoinitiator include a photobase generator that generates a base by irradiation, a photoacid generator that generates an acid by irradiation, and the photobase generator is particularly preferable.
- the adhesiveness of the photosensitive adhesive to the adherend (high temperature adhesiveness) and moisture resistance can be further improved.
- the base generated from the photobase generator efficiently acts as a curing catalyst for the epoxy resin, so that the crosslinking density can be further increased, and the generated curing catalyst corrodes the substrate and the like.
- the crosslink density can be improved, and the outgas during standing at high temperature can be further reduced. Furthermore, it is considered that the temperature of the curing process can be lowered and shortened.
- the photobase generator can be used without particular limitation as long as it is a compound that generates a base upon irradiation with radiation.
- a strongly basic compound is preferable in terms of reactivity and curing speed.
- Examples of such bases generated upon irradiation include imidazole derivatives such as imidazole, 2,4-dimethylimidazole and 1-methylimidazole, piperazine derivatives such as piperazine and 2,5-dimethylpiperazine, piperidine and 1,2, -A piperidine derivative such as dimethylpiperidine, a proline derivative, a trialkylamine derivative such as trimethylamine, triethylamine and triethanolamine, an amino group or an alkylamino group substituted at the 4-position of 4-methylaminopyridine and 4-dimethylaminopyridine Fatty acids such as pyridine derivatives, pyrrolidine derivatives such as pyrrolidine and n-methylpyrrolidine, dihydropyridine derivatives, triethylenediamine and 1,8-diazabiscyclo (5,4,0) undecene-1 (DBU) Wherein the amine derivatives, as well as benzyl methyl amine, benzyl amine derivatives such as benzyl di
- the photobase generator a compound in which a group capable of generating a base is introduced into the main chain and / or side chain of the polymer may be used.
- the molecular weight is preferably from 1,000 to 100,000, more preferably from 5,000 to 30,000, from the viewpoints of adhesiveness, fluidity and heat resistance as a photosensitive adhesive.
- the photobase generator does not react with the epoxy resin when not exposed to light, the storage stability at room temperature is very excellent.
- the amount of the photopolymerization initiator may be 5 parts by mass or more or 1 part by mass with respect to 100 parts by mass of the radiation polymerizable compound.
- the amount of the photopolymerization initiator may be 0.1 parts by mass or less or 1 part by mass or less with respect to 100 parts by mass of the radiation polymerizable compound.
- the photosensitive adhesive according to the present embodiment can be used in combination with a sensitizer as necessary.
- this sensitizer include camphorquinone, benzyl, diacetyl, benzyldimethyl ketal, benzyl diethyl ketal, benzyl di (2-methoxyethyl) ketal, 4,4′-dimethylbenzyl-dimethyl ketal, anthraquinone, 1-chloroanthraquinone.
- the photosensitive adhesive according to the present embodiment may contain (D) a thermoplastic resin in terms of improving low stress, adhesion to an adherend, and thermocompression bonding.
- the glass transition temperature (Tg) of the component (D) is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, still more preferably 100 ° C. or lower, and most preferably 80 ° C. or lower. preferable. When this Tg exceeds 150 ° C., the viscosity of the photosensitive adhesive tends to increase. Further, a high temperature of 150 ° C. or higher is required for thermocompression bonding to the adherend, and the semiconductor wafer tends to be warped.
- Tg means the main dispersion peak temperature of the (D) component formed into a film.
- RSA-2 rheometer viscoelasticity analyzer
- the weight average molecular weight of the component (D) is preferably controlled within the range of 5000 to 500,000, and more preferably 10,000 to 300,000 in terms of achieving both high compatibility with thermocompression bonding and high temperature adhesiveness.
- the “weight average molecular weight” means a weight average molecular weight when measured in terms of polystyrene using high performance liquid chromatography “C-R4A” (trade name) manufactured by Shimadzu Corporation.
- polyester resin polyether resin, polyimide resin, polyamide resin, polyamideimide resin, polyetherimide resin, polyurethane resin, polyurethaneimide resin, polyurethaneamideimide resin, siloxane polyimide resin, polyesterimide resin, these Copolymer, precursors thereof (polyamide acid, etc.), polybenzoxazole resin, phenoxy resin, polysulfone resin, polyethersulfone resin, polyphenylene sulfide resin, polyester resin, polyether resin, polycarbonate resin, polyether ketone Examples thereof include resins, (meth) acrylic copolymers having a weight average molecular weight of 10,000 to 1,000,000, novolac resins, and phenol resins.
- the main chain and / or side chain of these resins may be provided with a glycol group such as ethylene glycol and propylene glycol, a carboxyl group, and / or a hydroxyl group.
- the component (D) is preferably a resin having an imide group.
- the resin having an imide group include polyimide resins, polyamideimide resins, polyetherimide resins, polyurethaneimide resins, polyurethaneamideimide resins, siloxane polyimide resins, polyesterimide resins, and copolymers thereof.
- the polyimide resin can be obtained by subjecting tetracarboxylic dianhydride and diamine to a condensation reaction by a known method.
- tetracarboxylic dianhydride and diamine are equimolar, or if necessary, the total amount of diamine is preferably 0.00 with respect to the total 1.0 mol of tetracarboxylic dianhydride.
- the composition ratio is adjusted in the range of 5 to 2.0 mol, more preferably 0.8 to 1.0 mol (the order of addition of each component is arbitrary), and the addition reaction is performed at a reaction temperature of 80 ° C. or lower, preferably 0 to 60 ° C. .
- the viscosity of the reaction solution gradually increases, and polyamic acid, which is a polyimide resin precursor, is generated.
- the tetracarboxylic dianhydride is preferably purified by recrystallization with acetic anhydride in order to suppress deterioration of various characteristics of the photosensitive adhesive.
- the polyimide resin can be obtained by dehydrating and ring-closing the reactant (polyamide acid).
- the dehydration ring closure can be performed by a thermal ring closure method in which heat treatment is performed, a chemical ring closure method using a dehydrating agent, or the like.
- the tetracarboxylic dianhydride used as a raw material for the polyimide resin is not particularly limited.
- the tetracarboxylic dianhydride represented by the general formula (7) can be synthesized from, for example, trimellitic anhydride monochloride and the corresponding diol. Specifically, 1,2- (ethylene) bis (trimellitic anhydride), 1,3- (trimethylene) bis (trimellitic anhydride), 1,4- (tetramethylene) bis (trimellitic anhydride), 1,5 -(Pentamethylene) bis (trimellitic anhydride), 1,6- (hexamethylene) bis (trimellitic anhydride), 1,7- (heptamethylene) bis (trimellitic anhydride), 1,8- (octamethylene) Bis (trimellitic anhydride), 1,9- (nonamethylene) bis (trimellitic anhydride), 1,10- (decamethylene) bis (trimellitic anhydride), 1,12- (dodecamethylene) bis (trimellitic anhydride), 1,16- (hexadecamethylene) bis (trimell
- the tetracarboxylic dianhydride is a tetracarboxylic dianhydride represented by the following formula (8) or (9) from the viewpoint of imparting good solubility in solvents and moisture resistance and transparency to light having a wavelength of 365 nm.
- Anhydrides are preferred.
- tetracarboxylic dianhydrides can be used singly or in combination of two or more.
- a polyimide resin containing a carboxyl group and / or a phenolic hydroxyl group can be used in terms of further increasing the adhesive strength.
- the diamine used as a raw material for the carboxyl group and / or hydroxyl group-containing polyimide resin preferably contains an aromatic diamine represented by the following formula (10), (11), (12) or (13).
- the other diamine used as the raw material for the polyimide resin is not particularly limited, and examples thereof include o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 3,3′-diaminodiphenyl ether, and 3,4′-diaminodiphenyl ether.
- aliphatic ether diamines represented by the following general formula (14) are preferable, and ethylene glycol and / or propylene glycol-based diamines are more preferable in terms of imparting compatibility with other components.
- R 1 , R 2 and R 3 each independently represents an alkylene group having 1 to 10 carbon atoms, and b represents an integer of 2 to 80.
- aliphatic ether diamines include Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-900, ED-2000, and EDR manufactured by Sun Techno Chemical Co., Ltd. 148, aliphatic diamines such as polyoxyalkylene diamines such as polyetheramine D-230, D-400 and D-2000. These diamines are preferably 20 mol% or more of the total diamines, and are compatible with other compounding components such as (A) thermosetting resins and (B) radiation-polymerizable compounds, and thermocompression bonding properties and high temperatures. It is more preferably 50 mol% or more from the viewpoint that the adhesiveness is highly compatible.
- the siloxane diamine represented by following General formula (15) is preferable at the point which provides the adhesiveness and adhesiveness in room temperature.
- R 4 and R 9 each independently represent an alkylene group having 1 to 5 carbon atoms or a phenylene group which may have a substituent
- R 5 , R 6 , R 7 and R Each of 8 independently represents an alkyl group having 1 to 5 carbon atoms, a phenyl group or a phenoxy group
- d represents an integer of 1 to 5.
- diamines are preferably 0.5 to 80 mol% of the total diamine, and more preferably 1 to 50 mol% in terms of achieving both high thermocompression bonding and high temperature adhesiveness. If the amount is less than 0.5 mol%, the effect of adding siloxane diamine is reduced. If the amount exceeds 80 mol%, the compatibility with other components and high-temperature adhesiveness tend to be reduced.
- siloxane diamine represented by the general formula (15) is 1, 1,1,3,3-tetramethyl-1,3-bis (4- Aminophenyl) disiloxane, 1,1,3,3-tetraphenoxy-1,3-bis (4-aminoethyl) disiloxane, 1,1,3,3-tetraphenyl-1,3-bis (2- Aminoethyl) disiloxane, 1,1,3,3-tetraphenyl-1,3-bis (3-aminopropyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (2- Aminoethyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane, 1,1,3,3-tetramethyl-1,3-bis (3- Aminobutyl) disiloxane and 1,3-dimethyl- , 3-dimeth
- d is 2, 1,1,3,3,5,5-hexamethyl-1,5-bis (4-aminophenyl) trisiloxane, 1,1,5,5-tetra Phenyl-3,3-dimethyl-1,5-bis (3-aminopropyl) trisiloxane, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-bis (4-aminobutyl) Trisiloxane, 1,1,5,5-tetraphenyl-3,3-dimethoxy-1,5-bis (5-aminopentyl) trisiloxane, 1,1,5,5-tetramethyl-3,3-dimethoxy -1,5-bis (2-aminoethyl) trisiloxane, 1,1,5,5-tetramethyl-3,3-dimethoxy-1,5-bis (4-aminobutyl) trisiloxane, 1,1, 5,5-tetramethyl-3,3-dimethoxy-1,5
- diamines can be used singly or in combination of two or more.
- the above polyimide resins can be used alone or as a mixture (blend) of two or more if necessary.
- the composition of the polyimide resin when determining the composition of the polyimide resin, it is preferably designed so that the Tg of the polyimide resin is 150 ° C. or less.
- the diamine that is a raw material of the polyimide resin the general formula (14) It is particularly preferred to use the aliphatic ether diamine represented.
- a polymer By synthesizing a monofunctional acid anhydride such as a compound represented by the following formula (16), (17) or (18) and / or a monofunctional amine into the condensation reaction solution during the synthesis of the polyimide resin, a polymer is obtained.
- a functional group other than acid anhydride or diamine can be introduced at the terminal. Further, this can lower the molecular weight of the polymer, reduce the viscosity of the photosensitive adhesive, and improve the thermocompression bonding property.
- the (D) component may have a functional group having a function of accelerating the curing of an epoxy resin such as imidazole as its main chain and / or side chain.
- an imidazole-containing polyimide can be obtained as follows. A part of the diamine component shown above can be obtained using an imidazole group-containing diamine as represented by the following structural formula.
- the transmittance for light having a wavelength of 365 nm when the thickness is formed to 30 ⁇ m is preferably 10% or more, and can be B-staged with a lower exposure amount. And more preferably 20% or more.
- a polyimide resin is represented by, for example, an acid anhydride represented by the general formula (7), an aliphatic ether diamine represented by the general formula (14), and / or the general formula (15). It can be synthesized by reacting with siloxane diamine.
- thermoplastic resin it is preferable to use a liquid thermoplastic resin that is liquid at room temperature (25 ° C.) from the viewpoint of suppressing an increase in viscosity and further reducing undissolved residue in the photosensitive adhesive.
- a thermoplastic resin can be reacted by heating without using a solvent, and in the case of a photosensitive adhesive that does not apply a solvent as in this embodiment, the solvent removal process is reduced, and the remaining solvent is reduced. This is useful in terms of reducing the reprecipitation process. Further, the liquid thermoplastic resin can be easily taken out from the reaction furnace.
- Such a liquid thermoplastic resin is not particularly limited, but rubber-like polymers such as polybutadiene, acrylonitrile-butadiene oligomer, polyisoprene and polybutene, polyolefin, acrylic polymer, silicone polymer, polyurethane, polyimide, polyamideimide, etc. Is mentioned. Of these, a polyimide resin is preferably used.
- the liquid polyimide resin can be obtained, for example, by reacting the acid anhydride with an aliphatic ether diamine or siloxane diamine.
- an acid anhydride is dispersed in an aliphatic ether diamine or siloxane diamine without adding a solvent and heated.
- the photosensitive adhesive according to this embodiment is subjected to exposure using a high-precision parallel exposure machine (“EXM-1172-B- ⁇ ” (trade name) manufactured by Oak Manufacturing Co., Ltd.), and then melted at 20 ° C. to 300 ° C.
- a photosensitive adhesive having a viscosity of 30000 Pa ⁇ s or less is preferable.
- a parallel exposure machine (“ML-210FM Mask Aligner” (trade name) manufactured by Luminous Co., Ltd.) may be used instead of the high-precision parallel exposure machine.
- the “minimum melt viscosity” is measured using a viscoelasticity measuring device ARES (manufactured by Rheometrics Scientific FP Co., Ltd.) after exposing the sample with light having a light amount of 1000 mJ / cm 2.
- ARES viscoelasticity measuring device
- the minimum value of the melt viscosity at 20 ° C. to 300 ° C. is shown. Note that a parallel plate having a diameter of 8 mm is used as the measurement plate.
- the temperature rise rate is 5 ° C./min
- the measurement temperature is 20 ° C. to 300 ° C.
- the frequency is 1 Hz.
- the minimum melt viscosity is preferably 20000 Pa ⁇ s or less, more preferably 18000 Pa ⁇ s or less, and even more preferably 15000 Pa ⁇ s or less.
- the lower limit of the minimum melt viscosity is not particularly provided, but is preferably 10 Pa ⁇ s or more from the viewpoint of handleability.
- the photosensitive adhesive according to the present embodiment can use a thermal radical generator as necessary.
- the thermal radical generator is preferably an organic peroxide.
- the organic peroxide preferably has a 1 minute half-life temperature of 80 ° C. or higher, more preferably 100 ° C. or higher, and most preferably 120 ° C. or higher.
- the organic peroxide is selected in consideration of the preparation conditions of the photosensitive adhesive, the film forming temperature, the curing (bonding) conditions, other process conditions, storage stability, and the like.
- the organic peroxide that can be used is not particularly limited.
- the organic peroxide the unreacted radiation-polymerizable compound remaining after the exposure can be reacted, and the outgas can be reduced (lower outgassing) and the adhesion can be increased.
- the amount of the thermal radical generator is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, and most preferably 0.5 to 5% by mass with respect to the total amount of the radiation polymerizable compound. If it is less than 0.01% by mass, the curability is lowered and the effect of addition becomes small, and if it exceeds 5% by mass, the amount of outgas increases and the storage stability tends to be reduced.
- the thermal radical generator is not particularly limited as long as it has a half-life temperature of 80 ° C. or more for 1 minute.
- a half-life temperature 80 ° C. or more for 1 minute.
- perhexa 25B manufactured by NOF Corporation
- 2,5-dimethyl-2,5-di and t-butylperoxyhexane (1 minute half-life temperature: 180 ° C.
- Parkmill D manufactured by NOF Corporation
- dicumyl peroxide 1 minute half-life temperature: 175 ° C.
- the photosensitive adhesive according to the present embodiment is prohibited from polymerization of quinones, polyphenols, phenols, phosphites, sulfurs, etc. in order to impart storage stability, process adaptability or antioxidant properties.
- An agent or an antioxidant may be further added as long as the curability of the photosensitive adhesive is not impaired.
- the photosensitive adhesive according to this embodiment may contain a filler as appropriate.
- the filler include metal fillers such as silver powder, gold powder, copper powder and nickel powder, alumina, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide,
- metal fillers such as silver powder, gold powder, copper powder and nickel powder, alumina, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, calcium silicate, magnesium silicate, calcium oxide, magnesium oxide
- inorganic fillers such as aluminum oxide, aluminum nitride, crystalline silica, amorphous silica, boron nitride, titania, glass, iron oxide and ceramic, and organic fillers such as carbon and rubber fillers, types and shapes, etc. It can be used without any particular limitation.
- the filler can be used properly according to the desired function.
- the metal filler is added for the purpose of imparting conductivity, thermal conductivity, thixotropy and the like to the photosensitive adhesive.
- Non-metallic inorganic filler is added for the purpose of imparting thermal conductivity, low thermal expansion and low hygroscopicity to the photosensitive adhesive layer, and the organic filler is for the purpose of imparting toughness to the photosensitive adhesive layer. Added.
- metal fillers, inorganic fillers or organic fillers can be used singly or in combination of two or more.
- a metal filler or an inorganic filler is preferable in that it can provide conductivity, thermal conductivity, or low moisture absorption characteristics required for an adhesive material for a semiconductor device
- an insulating filler is preferable in that it can provide insulation.
- silica fillers are more preferable because they have good dispersibility with respect to the photosensitive adhesive and can impart high adhesive strength during heating.
- the filler preferably has an average particle size of 10 ⁇ m or less and a maximum particle size of 30 ⁇ m or less, more preferably an average particle size of 5 ⁇ m or less and a maximum particle size of 20 ⁇ m or less. If the average particle size exceeds 10 ⁇ m and the maximum particle size exceeds 30 ⁇ m, the effect of improving fracture toughness tends to be insufficient.
- the lower limit of the average particle size and the maximum particle size is not particularly limited, but usually both are 0.001 ⁇ m or more.
- the amount of the filler is determined according to the properties or functions to be imparted, but is preferably 0 to 50% by mass, more preferably 1 to 40% by mass with respect to the total of the resin component (component (A) and the like) and the filler. 3 to 30% by mass is more preferable.
- the amount of the filler is preferably within the above range.
- the optimum amount of filler is determined in order to balance the required properties. Mixing and kneading in the case of using a filler can be carried out by appropriately combining ordinary stirrers, crackers, three-rollers, ball mills and other dispersers.
- various coupling agents can be added in order to improve interfacial bonding between different materials.
- the coupling agent include a silane coupling agent, a titanium coupling agent, and an aluminum coupling agent.
- a silane coupling agent is preferable because of its high effect, and a compound having a thermosetting functional group such as an epoxy group and a radiation polymerizable functional group such as methacrylate and / or acrylate is more preferable.
- the boiling point and / or decomposition temperature of the silane coupling agent is preferably 150 ° C. or higher, more preferably 180 ° C. or higher, and even more preferably 200 ° C. or higher.
- a silane coupling agent having a boiling point of 200 ° C. or higher and / or a decomposition temperature and having a thermosetting functional group such as an epoxy group and a radiation polymerizable functional group such as methacrylate and / or acrylate is most preferably used. It is done.
- the amount of the coupling agent is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the photosensitive adhesive to be used from the viewpoint of the effect, heat resistance and cost.
- an ion scavenger can be further added in order to adsorb ionic impurities and improve insulation reliability during moisture absorption.
- an ion scavenger is not particularly limited.
- triazine thiol compound a compound known as a copper damage preventer for preventing copper from being ionized and dissolved, such as a phenol-based reducing agent, Inorganic compounds such as bismuth-based, antimony-based, magnesium-based, aluminum-based, zirconium-based, calcium-based, titanium-based, zuzu-based, and mixed systems thereof.
- IXE-300 antimony type
- IXE-500 bismuth type
- IXE-600 antimony, bismuth mixed type
- IXE-700 magnesium and aluminum mixed system
- IXE-800 zirconium system
- IXE-1100 calcium system
- the amount of the ion scavenger is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the photosensitive adhesive from the viewpoint of the effect of addition, heat resistance, cost, and the like.
- the thixotropy index of the photosensitive adhesive is 1.0 to 3.0 from the viewpoint of flattening bubbles and mesh marks of the photosensitive adhesive layer by spontaneous flow of the photosensitive adhesive. Is preferred.
- the thixotropy index is 1.0 or more, there is a tendency that generation of sagging or the like in the photosensitive adhesive supplied and applied by a printing method can be suppressed and the printed shape can be kept good.
- the thixotropy index is 3.0 or less, it tends to be possible to suppress the occurrence of “chips” or blurring in the photosensitive adhesive supplied and applied by the printing method.
- the upper and lower limit values of the thixotropy index of the photosensitive adhesive may be 1.0, 1.2, 1.3, or 3.0.
- the viscosity at 25 ° C. of the photosensitive adhesive is such that the photosensitive adhesive is supplied from the mesh opening during printing from the viewpoint of handling the photosensitive adhesive such as supplying the photosensitive adhesive onto the printing plate at the time of work. It is preferably 1 to 100 Pa ⁇ s from the standpoint of omission and from the viewpoint of flattening the bubbles and mesh marks of the photosensitive adhesive layer after the printing by spontaneous flow of the photosensitive adhesive.
- the upper and lower limits of the viscosity of the photosensitive adhesive at 25 ° C. may be 1 Pa ⁇ s, 8.5 Pa ⁇ s, 12.8 Pa ⁇ s, 16.0 Pa ⁇ s, or 100 Pa ⁇ s.
- the above viscosity is a value when measured using an E-type rotational viscometer (manufactured by Tokyo Keiki Co., Ltd.) under conditions of 3 ° cone, 25 ° C., and rotation speed 0.5 rpm.
- thermosetting resin and a radiation polymerizable compound were stirred and dissolved in a four-necked separable flask installed in an oil bath while heating to 60 ° C. in a nitrogen atmosphere.
- a thermosetting initiator and a photopolymerization initiator were added to the obtained solutions, respectively, placed in a raking machine, kneaded, and then defoamed and kneaded at 5 Torr or less for 1 hour.
- the viscosity was adjusted by adding a radiation-polymerizable compound and defoaming kneading, and a photosensitive adhesive having a ratio of each component shown in Table 1 was obtained.
- Table 1 shows the viscosity and thixotropy index at 25 ° C. of each photosensitive adhesive.
- ML-210FM Mask Aligner (trade name) manufactured by Luminous Co., Ltd.) was used for the photosensitive adhesive layer formed on the silicon wafer by the screen printing method. Exposure was performed at 1000 mJ / cm 2 in a nitrogen atmosphere, and the photosensitive adhesive layer was changed to B stage. Further, as Comparative Example 1, a silicon wafer printed with the same photosensitive adhesive as that in Example 1 was prepared, put into a dryer at 100 ° C. for 1 hour, and B-staged by heating. After B-stage, using a probe tacking tester manufactured by Reska, 30 ° C.
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Abstract
Description
図1に示す半導体ウェハ6は、半導体パッケージ(半導体装置)(図6)に内蔵される半導体チップ13a及び13b(図6)を形成するために用いられる。半導体ウェハ6は典型的にはシリコンウェハである。半導体ウェハ6には、既に前工程によって回路が形成されていてもよい。感光性接着剤層形成工程では、例えば、図1に示されるように、半導体ウェハ6の回路が形成されている面とは反対側の面(裏面)に感光性接着剤5をスクリーン印刷法によって塗布(印刷)する。これによって、図2に示すように、半導体ウェハ6の裏面上に、均一な厚さの感光性接着剤層7が形成される。
上記感光性接着剤層7は、露光によってBステージ化された後に被着体に対する接着性を有する感光性接着剤層である。塗布された感光性接着剤層7に対して、露光装置によって可視光又は紫外線を照射して、感光性接着剤層7を構成する感光性接着剤5をBステージ化する。これによって感光性接着剤5に含まれる光重合開始剤と放射線重合性化合物による重合反応が進行し、Bステージ化された感光性接着剤層8は適切な粘着性と接着性を有する。具体的には、感光性接着剤層8が半導体ウェハ6に固定される。このように、加熱ではなく、露光によって感光性接着剤層7のBステージ化を行うことにより、バックグラインドテープを半導体ウェハ6に貼り合わせたままの状態で、感光性接着剤5の塗布及び感光性接着剤層7のBステージ化を行うことが可能となる。
次に、半導体ウェハ6及びその裏面上に形成された感光性接着剤層8を有する接着剤層付き半導体ウェハ20をウェハ側からダイシングし、個片化された半導体チップ11を作製する(図4)。すなわち、ダイシングマシーンによって、半導体ウェハ6を切断することで、半導体ウェハ6が複数の半導体チップ11に切り分けられる。このダイシング工程の前に、上記感光性接着剤層8が形成された半導体ウェハ6の裏面に、ダイシングフィルム10が貼り付けられることが好ましい。貼り付けは必要によって加熱しながら行われてもよい。例えば、ダイシングフィルム10によって全体をフレーム(ウェハリング)9に固定した状態で(図3)、ダイシングブレード12を用いて行われるのが好ましい(図4)。個片化された感光性接着剤層付き半導体チップ11は、ダイボンディング装置等を用いてピックアップされる(図5)。
まず熱硬化性樹脂と放射線重合性化合物とを、オイルバスに設置した4つ口セパラブルフラスコにて、窒素雰囲気下で60℃に加熱しながら攪拌し、溶解させた。得られた溶液にそれぞれ熱硬化開始剤と光重合開始剤とを加え、らいかい機に入れ、混練した後、5Torr以下で更に1時間脱泡混練を行った。さらに、放射線重合性化合物の添加と脱泡混練をすることで粘度を調整し、各成分が表1に示す割合の感光性接着剤を得た。各感光性接着剤の25℃での粘度及びチキソトロピー指数は表1に示す通りである。
得られた感光性接着剤を、V-screen V160メッシュ印刷版(株式会社NBCメッシュテック社製)を設置したMK-838SV印刷機(ミナミ株式会社製)を用いて、サイズ8インチφ、厚み50μmのシリコンウェハの裏面上に、6インチφの円形状に印刷塗布を行った。印刷後の感光性接着剤の様子を目視にて確認したところ、かすれ等が無く、均一な感光性接着剤層を設ける事ができた。
実施例1~4として、スクリーン印刷法によりシリコンウェハ上に形成された感光性接着剤層に、平行露光機(株式会社ルミナス製、「ML-210FMマスクアライナ」(商品名))を用いて、窒素雰囲気下、1000mJ/cm2で露光を行い、感光性接着剤層をBステージ化した。さらに、比較例1として、実施例1と同じ感光性接着剤を印刷したシリコンウェハを用意し、100℃の乾燥機に一時間投入し、加熱によるBステージ化を行った。Bステージ化後、レスカ社製のプローブタッキング試験機を用いて、プローブ直径:5.1mm、引き剥がし速度:10mm/s、接触荷重:100gf/cm2、接触時間:1sの条件で、30℃における感光性接着剤層の表面タック力を測定した。Bステージ化後の表面タック力は表1に示すとおりである。
上記「Bステージ化後の感光性接着剤層の表面のタック力測定」で得られたBステージ化後のシリコンウェハを観察した結果、実施例1~4で得られた感光性接着剤層が形成されたシリコンウェハには反りが見られなかった。しかし、比較例1で得られた感光性接着剤層が形成されたシリコンウェハでは加熱に伴うシリコンウェハの反りが見られ、シリコンウェハの端部と中央部との高低差は1.5cm程度であった。Bステージ化後のシリコンウェハの反りの観察結果は表1に示すとおりである。
スクリーン印刷法により感光性接着剤層が形成されたシリコンウェハのシリコンウェハ側にダイシングテープをラミネートし、ウェハリングに設置した後、ダイシング装置(株式会社ディスコ製、「DAD-3220」(商品名))を用いて、10×10mm角にダイシングを行った。実施例1~4において、ダイシング後のシリコンウェハの様子を確認したところ、シリコンチップが欠如すること無くダイシングが可能であった。また、ダイシングテープからシリコンチップを10個ピックアップしたところ、ダイシングテープへの感光性接着剤の転写は無く、ピックアップ性も良好であった。一方、比較例1では、Bステージ化後の感光性接着剤層のタック力が強すぎて、ダイシングを行うことができなかった。
上記と同様にして得られた接着剤層付きシリコンチップ(5×5mm角)を、別途用意したシリコンチップ(8×8mm角)上に熱圧着(200gf、120℃、3秒)し、オーブンにて180℃1時間、加熱硬化を行った。得られたサンプルを自動接着力試験機(株式会社アークテック製、「DAGE SERIES4000」(商品名))を用いて、250℃におけるせん断強度を測定した。測定結果は表1に示すとおりである。
YDCN700-7:東都化成(株)、クレゾールノボラック型エポキシ樹脂
YDF-8170C:東都化成(株)、ビスフェノールF型エポキシ樹脂
EP1032H60:JER(株)、トリス(ヒドロキシフェニル)メタン型固形エポキシ樹脂
アロニックスM-140:東亞合成(株)、N-アクリロイルオキシエチルヘキサヒドロフタルイミド
FA-220M:日立化成工業(株)、ポリエチレングリコール#200ジメタクリレート
I-819:チバ・ジャパン(株)、フェニルビス(2,4,6-トリメチルベンゾイル)-ホスフィンオキシド
I-379EG:チバ・ジャパン(株)、2-(ジメチルアミノ)-2-(4-メチルベンジル)-1-(4-モルホリノフェニル)ブタン-1-オン
1B2PZ:四国化成工業(株)、1-ベンジル-2-フェニルイミダゾール。
Claims (9)
- 半導体ウェハの一方の表面全体に、スクリーン印刷法によって感光性接着剤を塗布して感光性接着剤層を形成する工程と、
前記感光性接着剤層を露光によりBステージ化する工程と、
を含む、接着剤層付き半導体ウェハの製造方法。 - 前記感光性接着剤が、熱硬化性樹脂、放射線重合性化合物及び光重合開始剤を含有する、請求項1に記載の製造方法。
- 前記感光性接着剤が、熱硬化開始剤をさらに含有する、請求項1又は2に記載の製造方法。
- 前記感光性接着剤の25℃での粘度が1~100Pa・sであり、前記感光性接着剤のチキソトロピー指数が1.0~3.0である、請求項1~3のいずれか一項に記載の製造方法。
- 熱硬化性樹脂、放射線重合性化合物及び光重合開始剤を含有し、請求項1に記載の製造方法に用いるための感光性接着剤。
- 熱硬化開始剤をさらに含有する、請求項5に記載の感光性接着剤。
- 25℃での粘度が1~100Pa・sであり、チキソトロピー指数が1.0~3.0である、請求項5又は6に記載の感光性接着剤。
- 請求項1~4のいずれか一項に記載の製造方法によって得られた接着剤層付き半導体ウェハを個片化して、接着剤層付き半導体チップを得る工程と、
前記接着剤層付き半導体チップの半導体チップを支持部材又は他の半導体チップに接着する工程と、
を含む方法によって得られる半導体装置。 - 熱硬化性樹脂、放射線重合性化合物及び光重合開始剤を含有し、25℃での粘度が1~100Pa・sであり、チキソトロピー指数が1.0~3.0である、スクリーン印刷用感光性接着剤。
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