WO2011058998A1 - Liquid adhesive composition for semiconductor, semiconductor device, and method for manufacturing semiconductor device - Google Patents
Liquid adhesive composition for semiconductor, semiconductor device, and method for manufacturing semiconductor device Download PDFInfo
- Publication number
- WO2011058998A1 WO2011058998A1 PCT/JP2010/070018 JP2010070018W WO2011058998A1 WO 2011058998 A1 WO2011058998 A1 WO 2011058998A1 JP 2010070018 W JP2010070018 W JP 2010070018W WO 2011058998 A1 WO2011058998 A1 WO 2011058998A1
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- Prior art keywords
- semiconductor
- adhesive composition
- adhesive layer
- resin
- adhesive
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- PSCBTUOBFRWCPB-GWNMMOMOSA-N CCC(CCC1=NC(N)NC(N)=N1)/C=C(/C)\N=C(/C)\CC Chemical compound CCC(CCC1=NC(N)NC(N)=N1)/C=C(/C)\N=C(/C)\CC PSCBTUOBFRWCPB-GWNMMOMOSA-N 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- 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
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- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01084—Polonium [Po]
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/049—Nitrides composed of metals from groups of the periodic table
- H01L2924/0495—5th Group
- H01L2924/04953—TaN
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/0665—Epoxy resin
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/078—Adhesive characteristics other than chemical
- H01L2924/07802—Adhesive characteristics other than chemical not being an ohmic electrical conductor
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/102—Material of the semiconductor or solid state bodies
- H01L2924/1025—Semiconducting materials
- H01L2924/10251—Elemental semiconductors, i.e. Group IV
- H01L2924/10253—Silicon [Si]
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/181—Encapsulation
Definitions
- the present invention relates to an adhesive composition for a liquid semiconductor, a semiconductor device using the same, and a method for manufacturing the same.
- a stack package type semiconductor device in which a plurality of chips are stacked in multiple stages is used for applications such as memory.
- a film adhesive is applied to bond semiconductor elements or semiconductor elements and a semiconductor element mounting support member.
- it has been required to further reduce the film adhesive for semiconductors.
- it has been difficult to produce a film adhesive having a thickness of 10 ⁇ m or less because a uniform film thickness cannot be obtained and pinholes frequently occur.
- the thinned film has poor adhesion to a wafer and thermocompression bonding, it is difficult to manufacture a semiconductor device using the film.
- the manufacturing cost increases due to a decrease in yield due to the above-mentioned problems.
- Patent Document 1 a method of applying an adhesive composition (resin paste) containing a solvent and forming the applied resin paste into a B-stage by heat drying is studied. Has been.
- the present invention has been made in view of the above circumstances, and further reduces the thickness of an adhesive layer that bonds semiconductor elements to each other or between a semiconductor element and a semiconductor element mounting support member while maintaining sufficient reliability. It is an object to provide an adhesive composition for a liquid semiconductor that can be formed, a method for manufacturing a semiconductor device using the same, and a semiconductor device.
- the present invention includes (A) a radiation-polymerizable compound, (B) a photoinitiator, and (C) a thermosetting resin, and (B) has a component (B1) having a wavelength of 365 nm.
- a liquid semiconductor adhesive composition comprising a compound having a molecular extinction coefficient with respect to light of 100 ml / g ⁇ cm or more.
- the molecular extinction coefficient was determined by preparing a 0.001 mass% acetonitrile solution of the sample, placing the solution in a quartz cell, and measuring the spectrophotometer (Hitachi High-Technologies Corp., “U-” at room temperature (25 ° C.) under air. 3310 "(trade name)) to determine the absorbance.
- liquid means having fluidity at 25 ° C. and 1 atm.
- the adhesive composition for a liquid semiconductor of the present invention having the above-described configuration, it can be applied onto a substrate without using a solvent, and the coating film is irradiated with light to form a thin film adhesive.
- a layer can be formed, and even when the adhesive layer is B-staged, heating for drying the solvent is not required after coating, and thus the occurrence of pinholes due to heat flow and volatile components is sufficiently suppressed. be able to.
- the above-described problems when using a conventional resin paste containing a solvent can be sufficiently solved.
- the B-staged adhesive composition for liquid semiconductors of the present invention is excellent in thermal fluidity, it can perform good thermocompression bonding to the adherend.
- ADVANTAGE OF THE INVENTION According to this invention, it is excellent in adhesiveness, thermocompression-bonding property, and heat resistance, For liquid semiconductors which can form the layer of the adhesive agent which adhere
- the adhesive composition for a liquid semiconductor of the present invention can form a thin adhesive layer in a short time without using a solvent and without heating, it is possible to reduce heat energy and volatilization.
- the load on the environment that can reduce the organic compound (VOC) can be a material smaller than before.
- the solvent content in the composition is preferably 5% by mass or less.
- the solvent refers to an organic compound that does not have a photoreactive group and a heat reactive group, has a molecular weight of 500 or less, and is liquid at 25 ° C.
- the component (B) preferably contains a compound having an oxime ester skeleton or a morpholine skeleton in the molecule as the compound (B1).
- a photoinitiator By including such a photoinitiator, tack force can be reduced by light irradiation under air. Further, even when an adhesive layer having a thickness of 20 ⁇ m or less, which is considered to be easily inhibited by radical polymerization due to oxygen, can be formed in a short time without heating. .
- the component (A) preferably contains a monofunctional (meth) acrylate that is liquid at 25 ° C.
- monofunctional means having one carbon-carbon double bond in the molecule, and may have other functional groups.
- the liquid semiconductor adhesive composition of the present invention preferably further contains (D) a thermal radical generator.
- the component (A) remaining unreacted after the exposure can be polymerized during the thermosetting, thereby further suppressing foaming at the time of thermosetting and foaming and peeling in the subsequent heat history. Can do.
- the liquid semiconductor adhesive composition of the present invention preferably further contains (E) a thermoplastic resin, and the (E) component contains a resin having an imide group.
- E a thermoplastic resin
- the (E) component contains a resin having an imide group.
- the liquid semiconductor adhesive composition of the present invention preferably has a viscosity at 25 ° C. of 10 to 30000 mPa ⁇ s.
- the viscosity here is a value of viscosity measured at 25 ° C. under the conditions of a sample volume of 0.4 mL and a 3 ° cone using an EHD type rotational viscometer manufactured by Tokyo Keiki Seisakusho.
- the present invention also provides a semiconductor device having a structure in which semiconductor elements and / or a semiconductor element and a semiconductor element mounting support member are bonded together by the liquid semiconductor adhesive composition of the present invention.
- the reliability of the semiconductor device is sufficiently maintained by bonding the semiconductor elements and / or the semiconductor element and the semiconductor element mounting support member with the liquid semiconductor adhesive composition of the present invention.
- the adhesive layer can be made thin, it is possible to reduce the size and height.
- the present invention also includes a step of applying the liquid semiconductor adhesive composition of the present invention on one surface of a semiconductor wafer to provide an adhesive layer, a step of irradiating the adhesive layer with light, Cutting the semiconductor wafer together with the adhesive layer to obtain a semiconductor element with an adhesive layer, a semiconductor element with an adhesive layer, and another semiconductor element or a semiconductor element mounting support member.
- pinching on the other side of the adhesive bond layer is provided.
- the present invention also includes a step of applying an adhesive layer by applying the liquid semiconductor adhesive composition of the present invention to a semiconductor element, a step of irradiating the adhesive layer with light, and a light irradiated adhesive layer.
- a method for manufacturing a semiconductor device comprising: a step of bonding a semiconductor element including a semiconductor element or another semiconductor element or a semiconductor element mounting support member by pressure-bonding the adhesive layer irradiated with light.
- the present invention also includes a step of applying the liquid semiconductor adhesive composition of the present invention to a semiconductor element mounting support member to provide an adhesive layer, a step of irradiating the adhesive layer with light,
- a method for manufacturing a semiconductor device comprising: a semiconductor element mounting support member having an adhesive layer; and a step of bonding the semiconductor element by pressure-bonding the adhesive layer irradiated with light.
- the adhesive composition for liquid semiconductors which can form further thinner the layer of the adhesive agent which adhere
- a semiconductor device manufacturing method and a semiconductor device using the same can be provided.
- the adhesive composition for a liquid semiconductor of the present invention includes (A) a radiation polymerizable compound, (B) a photoinitiator, and (C) a thermosetting resin, and (B) component has a wavelength of 365 nm (B1). It includes a compound having a molecular extinction coefficient with respect to light of 100 ml / g ⁇ cm or more (hereinafter sometimes referred to as “B1 compound”).
- the (A) radiation polymerizable compound means a compound having an unsaturated bond between carbon atoms such as alkenes and alkynes.
- radiation refers to ionizing radiation or non-ionizing radiation, such as excimer laser light such as ArF and KrF, electron beam extreme ultraviolet light, vacuum ultraviolet light, X-rays, ion beams, i-rays, and g-rays. UV light.
- excimer laser light such as ArF and KrF
- electron beam extreme ultraviolet light such as ArF and KrF
- vacuum ultraviolet light such as ArF and KrF
- X-rays extreme ultraviolet light
- ion beams such as i-line
- g-line is preferably used from the viewpoint of mass productivity.
- the liquid semiconductor adhesive composition of the present invention is preferably a solventless liquid semiconductor adhesive composition having a solvent content of 5% by mass or less.
- solventless type means that the amount of solvent contained in the adhesive composition is 5% by mass or less.
- the above-mentioned solvent means photoreactive groups such as radiation polymerizable group, oxime ester group, ⁇ -aminoacetophenone, phosphine oxide, epoxy group, phenolic hydroxyl group, carboxyl group, amino group, acid anhydride, isocyanate, peroxide
- An organic compound which does not have a thermally reactive group such as diazo group, imidazole or alkoxysilane, has a molecular weight of 500 or less and is liquid at room temperature (25 ° C.).
- Examples of such a solvent include dimethylformamide, toluene, benzene, xylene, methyl ethyl ketone, tetrahydrofuran, ethyl cellosolve, ethyl cellosolve acetate, dioxane, cyclohexanone, ethyl acetate, ⁇ -butyrolactone and N-methyl-pyrrolidinone.
- tack can be reduced by light irradiation, and handling properties after light irradiation are improved. Furthermore, foaming during thermocompression bonding or heat curing can be suppressed.
- Examples of the component (A) used in the present invention include compounds having an ethylenically unsaturated group.
- the ethylenically unsaturated group include vinyl group, allyl group, propargyl group, butenyl group, ethynyl group, phenylethynyl group, maleimide group, nadiimide group, (meth) acryl group and the like.
- a (meth) acryl group is preferred from the viewpoint of reactivity, and the component (A) preferably contains (A1) monofunctional (meth) acrylate (hereinafter also referred to as A1 compound).
- the monofunctional here means having one carbon-carbon double bond in the molecule, and may have other functional groups.
- the monofunctional (meth) acrylate preferably has a 5% weight loss temperature of 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.
- a material design mainly comprising an organic compound is preferable.
- the 5% weight loss temperature is preferably 500 ° C. or lower.
- the 5% mass reduction temperature of the monofunctional (meth) acrylate was measured using a differential thermothermal gravimetric simultaneous measurement apparatus (manufactured by SII NanoTechnology: TG / DTA6300) with a temperature rising rate of 10 ° C./min and a nitrogen flow (400 ml / min) is the 5% weight loss temperature as measured under.
- the unreacted monofunctional (meth) acrylate remaining after being B-staged by exposure is volatilized during thermocompression bonding or thermosetting. This can be suppressed.
- Monofunctional (meth) acrylates include, for example, phenolic hydroxyl groups such as glycidyl group-containing (meth) acrylate, 4-hydroxyphenyl methacrylate, and 3,5-dimethyl-4-hydroxybenzylacrylamide in that the cured product can be toughened.
- Carboxy group-containing (meth) acrylates such as (meth) acrylate, 2-methacryloyloxyethylphthalic acid, 2-methacryloyloxypropylhexahydrophthalic acid, 2-methacryloyloxymethylhexahydrophthalic acid are preferable, and heat resistance is improved.
- R 1 represents a hydrogen atom or a methyl group
- R 3 represents a monovalent organic group
- R 2 and R 4 represent a divalent organic group, respectively.
- R 3 preferably has an aromatic group from the viewpoint of heat resistance.
- R 4 preferably has an aromatic group from the viewpoint of heat resistance.
- R 1 represents a hydrogen atom or a methyl group
- R 5 represents a divalent organic group
- R 6 , R 7 , R 8 , R 9 are Each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 6 and R 7 may be bonded to each other to form a ring
- R 8 and R 9 may be bonded to each other to form a ring. May be.
- examples thereof include a benzene ring structure and an alicyclic structure.
- the benzene ring structure and the alicyclic structure may have a thermosetting group such as a carboxyl group, a phenolic hydroxyl group, and an epoxy group, or may have an organic group such as an alkyl group.
- the compounds represented by the general formulas (A-3) and (A-4) include, for example, an N-hydroxyalkylimide compound obtained by reacting a monofunctional acid anhydride and ethanolamine, an acrylate ester or an acrylic ester. It can be synthesized by reacting with an acid ester by a known method.
- Examples of the compounds represented by the general formulas (A-3) and (A-4) include storage stability, low tack after B-stage, adhesion after B-stage, heat resistance after thermosetting, adhesion From the viewpoints of properties and reliability, compounds represented by the following general formulas (A-5) to (A-9) can be used as preferred, and from the viewpoint of low viscosity, the following general formula (A-5), The compounds represented by (A-7) to (A-9) can be used more preferably.
- R1 represents a hydrogen atom or a methyl group.
- monofunctional (meth) acrylate from a viewpoint of the adhesiveness with the adherend after B-stage formation, the adhesiveness after hardening, and heat resistance, a urethane group, an isocyanuric group, an imide group, a phenolic hydroxyl group, a hydroxyl group It is preferable to have either of these, and it is especially preferable that it is a monofunctional (meth) acrylate which has an imide group or a hydroxyl group in a molecule
- Monofunctional (meth) acrylates with epoxy groups have a 5% weight loss temperature during film formation from the viewpoints of storage stability, adhesion, assembly heating and low outgassing of the package after assembly, heat resistance and moisture resistance. It is preferably 150 ° C. or higher in that it can suppress volatilization or segregation on the surface due to heat drying, and it is further 180 ° C. or higher in that it can suppress voids and peeling due to outgassing during thermosetting and decrease in adhesion. Preferably, it is more preferably 200 ° C. or higher in terms of suppressing voids and peeling in the thermal history, and 260 ° C.
- a monofunctional (meth) acrylate having an epoxy group a compound having an aromatic ring in the molecule is preferable.
- the said heat resistance can be satisfied by using a polyfunctional epoxy resin whose 5% weight reduction temperature is 150 degreeC or more as a raw material.
- Examples of the monofunctional (meth) acrylate having an epoxy group include, for example, glycidyl methacrylate, glycidyl acrylate, 4-hydroxybutyl acrylate glycidyl ether, 4-hydroxybutyl methacrylate glycidyl ether, a functional group that reacts with an epoxy group, and an ethylenic group. Examples thereof include compounds obtained by reacting a compound having a saturated group with a polyfunctional epoxy resin.
- 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. More specifically, for example, in the presence of triphenylphosphine or tetrabutylammonium bromide, a polyfunctional epoxy resin having at least two or more epoxy groups in one molecule and 0.1 to 0 to 1 equivalent of epoxy groups. Obtained by reacting with 9 equivalents of (meth) acrylic acid.
- 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, particularly 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 monofunctional (meth) acrylate component having an epoxy group that satisfies the above heat resistance and purity is not particularly limited, but bisphenol A type (or AD type, S type, F type) glycidyl ether, water-added bisphenol A type Glycidyl ether, ethylene oxide adduct bisphenol A and / or F type glycidyl ether, propylene oxide adduct bisphenol A and / or F type glycidyl ether, phenol novolac resin glycidyl ether, cresol novolac resin glycidyl ether, bisphenol A novolak Glycidyl ether of resin, glycidyl ether of naphthalene resin, trifunctional (or tetrafunctional) glycidyl ether, glycidyl ether of dicyclopentadiene phenol resin, glycidyl of dimer acid Glycol ester, 3 glycidylamine functional type (or
- the number of epoxy groups is preferably 3 or less in order to improve thermocompression bonding, low stress properties, and adhesion.
- a compound is not particularly limited, but a compound represented by the following general formula (A-1), (A-2), (A-3), (A-4) or (A-5), etc. 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 is an organic group having an epoxy group
- R 17 and R 18 are each an organic group having an ethylenically unsaturated group
- the rest are organic groups having an epoxy group.
- f in (A-4) represents an integer of 0 to 3.
- the content of the monofunctional (meth) acrylate is preferably 20 to 100% by mass, more preferably 40 to 100% by mass, and 50 to 100% by mass with respect to the total amount of component (A). Most preferably it is.
- the compound which is liquid at 25 ° C. and has one carbon-carbon double bond in the molecule should be used alone or in combination of two or more. Can do.
- the A1 compound preferably has a viscosity at 25 ° C. of 5000 mPa ⁇ s or less from the viewpoint of solubility of other components such as the component (B) and the component (C). More preferably, it is 3000 mPa ⁇ s or less, and even more preferably 2000 mPa ⁇ s or less. Further, from the viewpoint of improving adhesion by adding a large amount of a solid or high viscosity thermosetting resin, it is 1000 mPa ⁇ s or less. Most preferably it is.
- the viscosity here is the value for the A1 compound, and the viscosity value measured at 25 ° C. under the conditions of a sample volume of 0.4 mL and a 3 ° cone using an EHD type rotational viscometer manufactured by Tokyo Keiki Seisakusho. It is.
- the viscosity of the A1 compound exceeds 5000 mPa ⁇ s, the viscosity of the adhesive composition tends to increase, making it difficult to make a thin film, or to discharge from a nozzle of a coating apparatus or the like.
- the viscosity of the A1 compound at 25 ° C. is preferably 10 mPa ⁇ s or more.
- the viscosity of the A1 compound is preferably 1000 mPa ⁇ s or less from the viewpoint of improving dischargeability when the adhesive composition is discharged from a nozzle or the like and reducing the film thickness, and 5 mPa ⁇ s from the viewpoint of reducing outgas. The above is preferable.
- the A1 compound preferably has a 5% weight loss temperature of 100 ° C. or higher, more preferably 120 ° C. or higher, even more preferably 150 ° C. or higher, and 180 ° C. or higher.
- the 5% mass reduction temperature means that the A1 compound was heated at a rate of temperature increase of 10 ° C./min, a nitrogen flow (400 ml / 400 ml) using a differential thermothermal gravimetric simultaneous measurement apparatus (manufactured by SII Nanotechnology: TG / DTA6300) min) is the 5% weight loss temperature as measured under.
- a material design mainly composed of an organic compound is preferable. Therefore, 5% by weight of the above A1 compound
- the decreasing temperature is preferably 500 ° C. or lower.
- the A1 compound is preferably one in which the Tg of the polymer obtained by polymerizing the A1 compound is 100 ° C. or lower from the viewpoint of low-temperature thermocompression bonding and hot fluidity after B-stage formation. From the viewpoint of later pickup properties, those having a Tg of 20 ° C. or higher are preferred.
- the Tg of the polymer of the A1 compound is a composition obtained by dissolving I-379EG (manufactured by Ciba Japan), a photoinitiator, in the A1 component at a ratio of 3% by mass based on the total amount of the composition.
- the measurement plate is a parallel plate having a diameter of 8 mm, and the measurement conditions are a heating rate of 5 ° C./min, a measurement temperature of ⁇ 50 ° C. to 200 ° C., and a frequency of 1 Hz.
- the liquid semiconductor adhesive composition of the present invention may contain a bifunctional or higher functional (meth) acrylate in addition to the A1 compound as the (A) radiation polymerizable compound.
- a bifunctional or higher as used herein means having two or more carbon-carbon double bonds in the molecule.
- Such acrylate is not particularly limited, but 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, and g and h each independently represent an integer of 1 to 20.
- a compound in which R 15 in the above formula (A-3) is an organic group having an ethylenically unsaturated group, and two or more of R 17 in the above formula (A-4) have an ethylenically unsaturated group.
- a compound in which the remainder is an organic group having an epoxy group, and two or more of R 18 in the formula (A-5) are an organic group having an ethylenically unsaturated group, and the rest Is an organic group having an epoxy group.
- the adhesive composition according to the present invention may contain a monofunctional maleimide compound represented by the following structural formula for the purpose of reducing tack after exposure and improving adhesiveness.
- the component (A) is preferably liquid at room temperature (25 ° C.), the viscosity at 25 ° C. is preferably 5000 mPa ⁇ s or less, more preferably 3000 mPa ⁇ s or less, and 2000 mPa ⁇ s or less. It is still more preferable that it is 1000 mPa ⁇ s or less.
- the viscosity here is the value of the entire component (A) contained in the adhesive composition, using an EHD rotational viscometer manufactured by Tokyo Keiki Seisakusho, under the conditions of a sample amount of 0.4 mL and a 3 ° cone. The value of the viscosity measured at 25 ° C.
- the viscosity of the component (A) exceeds 5000 mPa ⁇ s, the viscosity of the adhesive composition tends to increase, making it difficult to reduce the thickness of the adhesive composition, or to discharge from a nozzle of a coating apparatus or the like.
- the viscosity of the component (A) at 25 ° C. is preferably 10 mPa ⁇ s or more.
- Component (A) preferably has a 5% weight loss 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 is the value of the entire component (A) contained in the adhesive composition, and the component (A) is subjected to a differential thermothermal gravimetric simultaneous measurement apparatus (manufactured by SII Nanotechnology: TG / DTA6300) is a 5% weight loss temperature when measured at a heating rate of 10 ° C./min and under a nitrogen flow (400 ml / min).
- the component (A) has a functional group equivalent of 150 g / eq or more from the viewpoint of fluidity during heating, preferably 200 g / eq or more from the viewpoint of adhesiveness during heating, and more preferably 300 g from the viewpoint of low stress. It is preferable that the acrylate is not less than / eq.
- the content of the component (A) is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and most preferably 40 to 90% by mass with respect to the total amount of the adhesive composition. preferable.
- the content of the component (A) is less than 10% by mass, the surface tack force after exposure tends to increase, and when it exceeds 95% by mass, the adhesive strength after thermosetting tends to decrease. .
- the liquid semiconductor adhesive composition of the present invention has a weight average molecular weight of 50,000 to 50,000 when irradiated with light from the viewpoint of adhesion to an adherend, reduction of surface tack, dicing, and improvement of high-temperature adhesion after curing. It is preferable that the polymer of the said (A) component which is 1000000 is contained.
- the polymer of the component (A) having a weight average molecular weight of 5000 to 500,000 when irradiated with light is included.
- the weight average molecular weight refers to a composition in which I-379EG (manufactured by Ciba Japan), a photoinitiator, is dissolved in component (A) at a ratio of 3% by mass based on the total amount of the composition.
- component (A) Polyethylene terephthalate
- the film was applied to a film thickness of 30 ⁇ m, and this film was coated at 1000 mJ / min with a high-precision parallel exposure machine (trade name: EXM-1172-B- ⁇ ) at 25 ° C. under air.
- EXM-1172-B- ⁇ high-precision parallel exposure machine
- the ratio of the component having a weight average molecular weight of 5000 or more to the component having a weight average molecular weight of less than 5000 is preferably 0.5 to 5.0.
- the weight average molecular weight of the polymer of component (A) is the exposure conditions (oxygen concentration, temperature, strength), the amount of photoinitiator, the addition of thiol, phenolic hydroxyl group, amine or phenolic polymerization inhibitor, the type of acrylate and the heat. It can adjust with the compounding quantity of curable resin, and the viscosity of an adhesive composition.
- a compound having a molecular extinction coefficient with respect to light having a wavelength of 365 nm of 100 ml / g ⁇ cm or more (B1 compound) in view of being capable of being B-staged is used.
- the molecular extinction coefficient with respect to the light of wavelength 365nm of a photoinitiator is 30000 ml / g * cm or less from a viewpoint of storage stability.
- the time required for the B-stage is preferably within 60 s, and more preferably within 30 s in that a semiconductor device can be more efficiently manufactured.
- a 0.001% by 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.
- the B1 compound is preferably an intramolecular cleavage type photoinitiator from the viewpoint of film formation efficiency.
- 2,2-dimethoxy-1,2-diphenylethane-1-one 2-hydroxy-1 - ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl-propan-1-one, 2-dimethylamino-2- (4-methyl-benzyl)- 1- (4-Morpholin-4-yl-phenyl) -butan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2-methyl-1- (4 -(Methylthio) phenyl) -2-morpholinopropanone-1, 1- [4- (phenylthio)-, 2- (o-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2 Methylbenzoyl) -9H-
- Examples include lysine derivatives, bisacylphosphine oxides such as bis (2,4,6, -trimethylbenzoyl) -phenylphosphine oxide, and compounds having maleimide. These can be used alone or in combination of two or more.
- 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-benzyl-2-dimethylamino- and the like from the viewpoint of solubility in an adhesive composition containing no solvent.
- the B1 compound is preferably a compound having an oxime ester skeleton or a morpholine skeleton in the molecule in that it can be efficiently B-staged by exposure even in an air atmosphere (in the presence of oxygen).
- a compound is not particularly limited, but is a compound having an oxime ester group represented by the following general formula (B-1) and / or the following general formula (B-2), (B-3) or (B- A compound having a morpholine ring represented by 4) is preferred.
- each of R 51 and R 52 independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, or an organic group containing an aromatic hydrocarbon group
- R 53, R 54, and R 55 represent carbon
- An alkyl group of 1 to 7 or an organic group containing an aromatic hydrocarbon group is shown
- R 56 and R 57 show an organic group containing an aromatic hydrocarbon group.
- the aromatic hydrocarbon group is not particularly limited, and examples thereof include a phenyl group and a naphthyl group, a benzoin derivative, a carbazole derivative, a thioxanthone derivative, and a benzophenone derivative. Moreover, the aromatic hydrocarbon group may have a substituent.
- the B1 compound is a compound having an oxime ester group and / or a morpholine ring, a molecular extinction coefficient with respect to light having a wavelength of 365 nm of 1000 ml / g ⁇ cm or more, and a 5% mass reduction temperature of 150 ° C. These compounds.
- B1 compounds include compounds represented by the following structural formulas (B-5) to (B-9). Since these compounds are particularly excellent in solubility in the (A) radiation polymerizable compound, they can be preferably used.
- the component (B) contains a photoinitiator that expresses a function of promoting polymerization and / or reaction of the epoxy resin by irradiation with radiation. Also good.
- 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 high-temperature adhesiveness and moisture resistance of the adhesive composition to the adherend can be further improved.
- the base generated from the photobase generator acts as a curing catalyst for the epoxy resin efficiently, so that the crosslinking density can be further increased, and the generated curing catalyst corrodes the substrate and the like. This is thought to be because there are few.
- the crosslink density can be improved, and the outgas during standing at high temperature can be further reduced. Furthermore, the curing process temperature can be lowered and shortened.
- the photobase generator may be a compound that generates a base when irradiated with radiation.
- a strongly basic compound is preferable in terms of reactivity and curing speed.
- Examples of the base 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-dimethylpiperidine.
- Piperidine derivatives such as, proline derivatives, trialkylamine derivatives such as trimethylamine, triethylamine and triethanolamine, pyridine derivatives substituted with an amino group or alkylamino group at the 4-position such as 4-methylaminopyridine and 4-dimethylaminopyridine, Pyrrolidine derivatives such as pyrrolidine, n-methylpyrrolidine, dihydropyridine derivatives, triethylenediamine, alicyclic amine derivatives such as 1,8-diazabiscyclo (5,4,0) undecene-1 (DBU), Rumechiruamin, benzyldimethylamine, and the like benzylamine derivatives such as benzyl diethylamine.
- DBU 1,8-diazabiscyclo (5,4,0) undecene-1
- photobase generators that generate bases upon irradiation are 2,4-dimethoxy-1,2-diphenylethane-1-one, 1,2-octanedione, 1- [4- (phenylthio)-, 2- Oxime derivatives such as (O-benzoyloxime)], ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime) and light 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl, which is commercially available as a radical generator -1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butyl
- the photobase generator a compound in which a base generating group is introduced into the main chain and / or side chain of the polymer may be used.
- the molecular weight in this case 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 an adhesive.
- the above photobase generator does not show reactivity with the epoxy resin when not exposed to light, the storage stability at room temperature is very excellent.
- the content of the (B) photoinitiator is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A), from the viewpoint of B-stage tact and B-stage tuck. More preferably, it is 0.5 to 10 parts by mass. If this content exceeds 20 parts by mass, the outgas will increase and the adhesiveness will tend to decrease, and the storage stability will tend to decrease. On the other hand, when the content is less than 0.1 parts by mass, it tends to be difficult to make a B stage.
- the ratio of the B1 compound in the (B) photoinitiator is preferably 20 to 100 parts by mass with respect to 100 parts by mass of the component (B) in that it can be B-staged with a low exposure amount, and depends on the exposure atmosphere.
- the amount is more preferably 50 to 100 parts by mass in terms of reducing the influence.
- a sensitizer can be used in combination 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.
- an oxygen inhibition reducing agent can be used in combination as necessary.
- organic phosphorus compounds, amine compounds, and thiol compounds are preferably used.
- a compound having a tertiary amine is preferably used from the viewpoint of storage stability and B-stage formation efficiency under air.
- each R 1 independently represents an alkyl group having 1 to 7 carbon atoms.
- R 1 independently represents an alkyl group having 1 to 7 carbon atoms
- R 2 represents a hydrogen atom or a methyl group
- R 3 represents an organic group having 1 to 30 carbon atoms.
- the (C) thermosetting resin is not particularly limited as long as it is a component composed of a reactive compound that undergoes a crosslinking reaction by heat.
- epoxy resins, maleimide resins, and allyl nadiimide resins are preferable because they can be mentioned.
- 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 impurity ions such as alkali metal ions, alkaline earth metal ions, halogen ions, particularly chlorine ions and hydrolyzable chlorine are reduced to 300 ppm or less. From the viewpoint of prevention and corrosion prevention of metal conductor circuits.
- impurity ions such as alkali metal ions, alkaline earth metal ions, halogen ions, particularly chlorine ions and hydrolyzable chlorine are reduced to 300 ppm or less.
- maleimide resins examples include bismaleimide resins represented by the following general formula (I) and novolac maleimide resins represented by the following general formula (II).
- R 5 represents a divalent organic group containing an aromatic ring and / or a linear, branched or cyclic aliphatic hydrocarbon.
- n represents an integer of 0 to 20.
- a bismaleimide resin represented by the following structural formula (III) and / or a novolac maleimide resin represented by the above general formula (II) in that heat resistance and high-temperature adhesive force after curing of the adhesive film can be imparted.
- an allylated bisphenol A, a cyanate ester compound or the like can be used in combination, or a catalyst such as a peroxide can be added.
- a catalyst such as a peroxide
- allyl nadiimide resin a compound containing two or more allyl naimide groups in the molecule can be used, and examples thereof include a bisallyl nadiimide resin represented by the following general formula (IV).
- R 1 represents a divalent organic group containing an aromatic ring and / or a linear, branched or cyclic aliphatic hydrocarbon.
- liquid hexamethylene type bisallyl nadiimide represented by the following structural formula (V) and low melting point (melting point: 40 ° C.) solid xylylene type bisallyl nadiimide represented by the following structural formula (VI) which is preferable in terms of providing good hot fluidity.
- Solid xylylene-type bisallylnadiimide can suppress the increase in adhesiveness after B-stage in addition to good fluidity during heat treatment, handling property, and easy release from dicing tape during pick-up. It is more preferable in terms of suppressing re-fusion of the cut surface after dicing.
- the above bisallylnadiimide can be used alone or in combination of two or more.
- the allyl nadiimide resin described above requires a curing temperature of 250 ° C. or higher when singly cured in the absence of a catalyst, which is a major obstacle to practical use. Only metal corrosive catalysts, which are a serious drawback in electronic materials such as onium salts and onium salts, can be used, and final curing requires a temperature of around 250 ° C. Can be cured at a low temperature of 200 ° C. or less by using any one of acrylate compound, methacrylate compound, and maleimide resin (reference: A. Renner, A. Kramer, “Allylindic-Imides: A New Class”). of Heat-Resistant Thermosets ", J. Polym. Sc ., Part A Polym.Chem., 27,1301 (1989)).
- thermosetting resin can be used regardless of liquid or solid at room temperature. In the case of a liquid thermosetting resin, the viscosity can be further reduced, and in the case of a solid thermosetting resin, tack after light irradiation can be further reduced. Moreover, you may use together a liquid thermosetting resin and a solid thermosetting resin.
- the viscosity is preferably 10,000 mPa ⁇ s or less, more preferably 5000 mPa ⁇ s or less, still more preferably 3000 mPa ⁇ s or less, and even more preferably 2000 mPa ⁇ s or less. Most preferably. When the viscosity exceeds 10,000 mPa ⁇ s, the viscosity of the adhesive composition increases and it tends to be difficult to form a thin film.
- Such a liquid thermosetting resin is not particularly limited, but is preferably an epoxy resin from the viewpoint of adhesiveness and heat resistance, and particularly a trifunctional (or tetrafunctional) glycidylamine or bisphenol A type (or AD type, S type, and F type glycidyl ethers are preferably used.
- a solid thermosetting resin when using a solid thermosetting resin, for example, it can be used by being dissolved in the component (A).
- a solid thermosetting resin From a viewpoint of thermocompression bonding property and viscosity, it is preferable that molecular weight is 2000 or less, Preferably it is 1000 or less, and a softening point is 100 degrees C or less, Preferably it is 80 degrees C The following is preferable.
- a trifunctional or higher functional epoxy resin is preferable from the viewpoint of adhesiveness and heat resistance.
- an epoxy resin for example, an epoxy resin having the following structure is preferably used.
- n an integer of 0 to 10.
- the (C) thermosetting resin preferably has a 5% weight loss 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 of the thermosetting resin means that the thermosetting resin is heated at a rate of 10 ° C./temperature using a differential thermothermal gravimetric simultaneous measurement apparatus (manufactured by SII Nanotechnology: TG / DTA6300).
- Min 5% weight loss temperature when measured under a nitrogen flow (400 ml / min).
- thermosetting resin having such heat resistance an epoxy resin having an aromatic group in the molecule is exemplified, and in particular from the viewpoint of adhesion and heat resistance, trifunctional (or tetrafunctional) glycidylamine, Bisphenol A type (or AD type, S type, F type) glycidyl ether is preferably used.
- the content of the thermosetting resin is preferably 1 to 100 parts by mass and more preferably 2 to 50 parts by mass with respect to 100 parts by mass of the component (A). When this content exceeds 100 parts by mass, the tack after exposure tends to increase. On the other hand, when the content is less than 2 parts by mass, there is a tendency that sufficient high-temperature adhesiveness cannot be obtained.
- the liquid semiconductor adhesive composition of the present invention preferably further contains a curing accelerator.
- the curing accelerator is not particularly limited as long as it is a compound that accelerates curing / polymerization of the epoxy resin by heating.
- imidazoles are preferably used from the viewpoint of solubility and dispersibility when no solvent is contained.
- the content of the curing accelerator is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the epoxy resin.
- imidazoles are particularly preferable from the viewpoints of adhesiveness, heat resistance, and storage stability.
- the reaction start temperature is preferably 50 ° C. or higher, and more preferably 80 ° C. or higher.
- the reaction start temperature is 50 ° C. or lower, the storage stability is lowered, so that the viscosity of the resin composition is increased and the control of the film thickness becomes difficult.
- imidazoles it is preferable to use imidazole that is soluble in an epoxy resin. By using such imidazole, a coating film with less unevenness can be obtained.
- Such imidazoles are not particularly limited, but 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole and the like. From the viewpoint of storage stability, adhesiveness, and heat resistance, 1-benzyl-2-phenylimidazole is particularly preferably used.
- imidazoles compounds pulverized to an average particle size of preferably 10 ⁇ m or less, more preferably 8 ⁇ m or less, and most preferably 5 ⁇ m or less can be used.
- a change in viscosity of the adhesive composition can be suppressed, and precipitation of imidazoles can be suppressed.
- surface irregularities can be reduced, and thereby a uniform film can be obtained.
- outgas can be reduced.
- the liquid semiconductor adhesive composition of the present invention 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.
- the phenolic compound is preferably liquid, and the allyl-modified phenol novolak is preferably used because it is liquid and highly heat resistant.
- the content of the phenolic compound is preferably 50 to 100 parts by mass and more preferably 60 to 95 parts by mass with respect to 100 parts by mass of the thermosetting resin.
- the liquid semiconductor adhesive composition of the present invention may further contain (D) a thermal radical generator.
- 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 adhesive composition, film forming temperature, pressure bonding, curing conditions, other process conditions, storage stability, and the like.
- the peroxide that can be used is not particularly limited.
- the unreacted radiation-polymerizable compound remaining after exposure can be reacted, and low outgassing and high adhesion can be achieved.
- the content of the thermal radical generator is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, and more preferably 0.5 to 5%, based on the total amount of the (A) radiation polymerizable compound. Mass% is most preferred. When the content of the thermal radical generator is less than 0.01% by mass, the curability is lowered and the effect of addition is reduced, and when it exceeds 5% by mass, the outgas amount is increased and the storage stability is decreased.
- the liquid semiconductor adhesive composition of the present invention may further contain (E) a thermoplastic resin in terms of improving low stress, adhesion to an adherend, and thermocompression bonding.
- Tg of component (E) is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, even more preferably 100 ° C. or lower, and most preferably 80 ° C. or lower.
- this Tg exceeds 150 ° C., the viscosity of the adhesive composition 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 of the (E) component means a main dispersion peak temperature when the (E) component is formed into a film.
- the film thickness is 100 ⁇ m
- the heating rate is 5 ° C./min
- the frequency is 1 Hz
- the measurement temperature Measure at ⁇ 150 to 300 ° C., and determine the tan ⁇ peak temperature near Tg as Tg.
- the weight average molecular weight of the component (E) is preferably controlled within the range of 5000 to 500,000. Furthermore, the weight average molecular weight of the component (E) is more preferably 10,000 to 300,000 from the viewpoint that the thermocompression bonding property and the high temperature adhesiveness can be highly compatible.
- 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.
- component (E) examples include polyester resins, polyether resins, polyimide resins, polyamide resins, polyamideimide resins, polyetherimide resins, polyurethane resins, polyurethaneimide resins, polyurethaneamideimide resins, siloxane polyimide resins, and polyesterimide resins.
- polybenzoxazole resin phenoxy resin, polysulfone resin, polyethersulfone resin, polyphenylene sulfide resin, polyester resin, polyether resin, polycarbonate resin, poly Examples thereof include ether ketone resins, (meth) acrylic copolymers having a weight average molecular weight of 10,000 to 1,000,000, novolac resins, and phenol resins. These can be used individually by 1 type or in combination of 2 or more types.
- the main chain and / or side chain of these resins may be provided with a glycol group such as ethylene glycol or propylene glycol, a carboxyl group, and / or a hydroxyl group.
- the component (E) is preferably a resin having an imide group.
- the resin having an imide group include a polyimide resin, a polyamideimide resin, a polyetherimide resin, a polyurethaneimide resin, a polyurethaneamideimide resin, a siloxane polyimide resin, a polyesterimide resin, a copolymer thereof, and a monomer having an imide group. These polymers are mentioned.
- the polyimide resin and / or polyamideimide resin can be obtained, for example, by subjecting tetracarboxylic dianhydride and diamine to a condensation reaction by a known method. That is, in the organic solvent, 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 polyimide resin and / or the polyamideimide resin can be obtained by dehydrating and ring-closing the reaction product (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.
- Examples of the tetracarboxylic dianhydride used as a raw material for the polyimide resin and / or the polyamideimide resin include, for example, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride in that the linear expansion coefficient can be reduced.
- Acid dianhydrides having a biphenyl skeleton such as dianhydrides, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 2,3, Acid dianhydrides having a naphthyl skeleton such as 6,7-naphthalenetetracarboxylic dianhydride and 1,2,4,5-naphthalenetetracarboxylic dianhydride are preferably used.
- 3,4,3 ′, 4′-benzophenone tetracarboxylic dianhydride, 2,3,2 ′, 3′-benzophenone tetracarboxylic dianhydride, Acid dianhydrides having a benzophenone skeleton such as, 3,3 ′, 4′-benzophenone tetracarboxylic dianhydride are preferably used.
- 1,2,3,4-butanetetracarboxylic dianhydride decahydronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1, 2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic dianhydride, cyclopentane-1,2,3,4-tetracarboxylic dianhydride, 1,2 , 3,4-cyclobutanetetracarboxylic dianhydride, bis (exo-bicyclo [2,2,1] heptane-2,3-dicarboxylic dianhydride, bicyclo- [2,2,2] -oct-7 -Acid dianhydrides having an alicyclic skeleton such as ene-2,3,5,6-tetracarboxylic dianhydride and 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride
- tetracarboxylic dianhydride represented by the following general formula (1) is preferably used.
- a represents an integer of 2 to 20.
- the tetracarboxylic dianhydride represented by the general formula (1) can be synthesized from, for example, trimellitic anhydride monochloride and the corresponding diol, specifically 1,2- (ethylene) bis ( Trimellitate anhydride), 1,3- (trimethylene) bis (trimellitic anhydride), 1,4- (tetramethylene) bis (trimellitate anhydride), 1,5- (pentamethylene) bis (trimellitate 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 (trimellitate anhydrous), 1,12- (dodecamechi) Emissions) bis (trimellitate anhydride), 1,16 (hexamethylene decamethylene) bis (
- the tetracarboxylic dianhydride is represented by the following general formula (2) or (3) from the viewpoint of imparting good solubility in the component (A), transparency to 365 nm light, and thermocompression bonding. Tetracarboxylic dianhydride is preferred.
- tetracarboxylic dianhydrides can be used singly or in combination of two or more.
- Component can use a carboxyl group and / or phenolic hydroxyl group containing polyimide resin at the point which raises adhesive strength further.
- 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 general formula (4), (5), (6) or (7).
- diamines used as raw materials for the polyimide resin are not particularly limited, but the following diamines can be used to adjust the Tg and solubility of the polymer.
- 3,3′-diaminodiphenyl sulfide, 3,4′-diaminodiphenyl sulfide, 4,4′-diaminodiphenyl sulfide, bis (4- (3- Aminoenoxy) phenyl) sulfide and bis (4- (4-aminoenoxy) phenyl) sulfide are preferably used.
- diamines that can lower Tg include 1,3-bis (aminomethyl) cyclohexane, aliphatic ether diamines represented by the following general formula (8), and siloxane diamines represented by the following general formula (9). Etc.
- 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.
- 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 8 Each 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.
- aliphatic ether diamines represented by the general formula (8) are preferable, and ethylene glycol and / or propylene glycol diamines are more preferable in terms of imparting compatibility with other components.
- 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, D-2000 and the like. These diamines are preferably 20 mol% or more of the total diamine, and are compatible with other components such as (A) radiation-polymerizable compounds and (C) thermosetting resins, and thermocompression bonding and high-temperature adhesion. It is more preferable that it is 50 mol% or more from the standpoint of achieving high compatibility with the properties.
- the diamine is preferably a siloxane diamine represented by the general formula (9) from the viewpoint of imparting adhesiveness and adhesiveness at room temperature.
- 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.
- the above-mentioned diamines can be used alone or in combination of two or more.
- the said polyimide resin can be used individually by 1 type or in mixture (blend) of 2 or more types as needed.
- the Tg when determining the composition of the polyimide resin, it is preferable to design the Tg to be 150 ° C. or less.
- the diamine that is the raw material of the polyimide resin the general formula (8) It is particularly preferred to use the aliphatic ether diamine represented.
- the thermoplastic resin may have a functional group having a function of accelerating curing of an epoxy resin such as imidazole in its main chain and / or side chain.
- the imidazole-containing polyimide can be obtained, for example, by using a diamine group-containing diamine as shown in the following structural formula as a diamine component shown above.
- the transmittance for 365 nm when molded to 30 ⁇ m is preferably 10% or more, and is 20% or more in that it can be B-staged at a lower exposure. It is more preferable.
- a polyimide resin is represented by, for example, an acid anhydride represented by the general formula (2), an aliphatic ether diamine represented by the general formula (8), and / or the general formula (9). It can be synthesized by reacting with siloxane diamine.
- thermoplastic resin (E) it is preferable to use a liquid thermoplastic resin that is liquid at room temperature (25 ° C.) in terms of suppressing an increase in viscosity and further reducing undissolved residue in the adhesive composition.
- a thermoplastic resin can be reacted by heating without using a solvent, and in an adhesive composition that does not apply the solvent as in the present invention, the solvent removal process is reduced, the residual solvent is reduced, and the reprecipitation process is performed. This is useful in terms of reduction.
- the liquid thermoplastic resin can be easily taken out from the reaction furnace.
- liquid thermoplastic resin examples include rubber-like polymers such as polybutadiene, acrylonitrile / butadiene oligomer, polyisoprene, and polybutene, polyolefins, acrylic polymers, silicone polymers, polyurethanes, polyimides, and polyamideimides. Of these, a polyimide resin is preferably used.
- the liquid polyimide resin can be obtained, for example, by reacting the above acid anhydride with an aliphatic ether diamine or siloxane diamine.
- Examples of the synthesis method include a method in which an acid anhydride is dispersed in an aliphatic ether diamine or siloxane diamine without adding a solvent and heated.
- the content of the thermoplastic resin is preferably 0.1 to 50% by mass relative to the component (A), and 0.5 to 20% by mass from the viewpoints of film formability, film thickness uniformity, and suppression of increase in viscosity. % Is more preferable. If the content of the thermoplastic resin is less than 0.1% by mass, the effect of addition tends to be lost, and if it exceeds 50% by mass, the film thickness uniformity decreases due to undissolved or the like. It tends to rise and make thinning difficult.
- the liquid semiconductor adhesive composition of the present invention may appropriately contain a filler.
- 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, Inorganic fillers such as aluminum oxide, aluminum nitride, crystalline silica, amorphous silica, boron nitride, titania, glass, iron oxide, and ceramics, and organic fillers such as carbon and rubber fillers are included. Regardless, it can be used without any particular restrictions.
- 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, etc. to the adhesive composition
- the nonmetallic inorganic filler is thermally conductive, low thermal expansion, low hygroscopicity to the adhesive layer.
- the organic filler is added for the purpose of imparting toughness to the adhesive layer.
- metal fillers, inorganic fillers or organic fillers can be used singly or in combination of two or more.
- metal fillers, inorganic fillers, or insulating fillers are preferable in terms of being able to impart conductivity, thermal conductivity, low moisture absorption characteristics, insulating properties, and the like required for adhesive materials for semiconductor devices, and inorganic fillers or insulating fillers.
- a silica filler is more preferable in that the dispersibility with respect to the adhesive composition is good and a high adhesive force during heating can be imparted.
- 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 or the maximum particle size exceeds 30 ⁇ m, the effect of improving fracture toughness tends to be insufficient. Further, the lower limits of the average particle size and the maximum particle size are not particularly limited, but both are preferably 0.001 ⁇ m or more.
- the content of the filler is determined according to the properties or functions to be imparted, but is preferably 50% by mass or less, more preferably 1 to 40% by mass with respect to the total amount of the adhesive composition containing the filler. More preferred is 30% by mass.
- the amount of filler By increasing the amount of filler, low alpha, low moisture absorption, and high elastic modulus can be achieved, and dicing performance (cutability with a dicer blade), wire bonding performance (ultrasonic efficiency), and adhesive strength during heating are effectively improved. Can be made.
- the amount of filler is increased more than necessary, the viscosity tends to increase or the thermocompression bonding property tends to be impaired. Therefore, the filler content is preferably within the above range.
- the optimum filler content can be determined to balance the required properties. Mixing and kneading in the case of using a filler can be carried out by appropriately combining dispersers such as ordinary stirrers, raking machines, three rolls, and ball mills.
- various coupling agents can be added in order to improve interfacial bonding between different materials.
- the coupling agent include silane-based, titanium-based, and aluminum-based.
- a silane-based coupling agent is preferable because of its high effect, and a thermosetting group such as an epoxy group, methacrylate, and / or acrylate.
- a compound having a radiation polymerizable group such as is more preferred.
- 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 group such as an epoxy group and a radiation polymerizable group such as methacrylate and / or acrylate is most preferably used.
- the amount of the coupling agent used is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the adhesive composition from the viewpoint of its effect, heat resistance and cost.
- an ion scavenger may be further added in order to adsorb ionic impurities and improve insulation reliability when absorbing moisture.
- an ion scavenger is not particularly limited, for example, a compound known as a copper damage inhibitor for preventing copper from being ionized and dissolved, such as a triazine thiol compound and a phenol-based reducing agent, a powder form Inorganic compounds such as bismuth-based, antimony-based, magnesium-based, aluminum-based, zirconium-based, calcium-based, titanium-based, zuz-based, and mixed systems thereof.
- IXE-300 antimony type
- IXE-500 bismuth type
- IXE-600 antimony and bismuth mixed type
- IXE-700. Matture of magnesium and aluminum
- IXE-800 zirconium
- IXE-1100 calcium and the like.
- the amount of the ion scavenger used is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the adhesive composition from the viewpoint of the effect of addition, heat resistance, cost and the like.
- the liquid semiconductor adhesive composition of the present invention preferably contains a compound having an imide group.
- the compound having an imide group is, for example, a low molecular compound such as a monofunctional (meth) acrylate having an imide group cited as the A1 compound, or a resin having an imide group such as a polyimide resin cited as the component (E). It can be included.
- the liquid semiconductor adhesive composition of the present invention preferably has a viscosity at 25 ° C. of 10 to 30000 mPa ⁇ s, preferably 30 to 20000 mPa ⁇ s from the viewpoint of improving the dischargeability of the adhesive composition and reducing the film thickness. More preferably, from the viewpoint of the heat resistance of the adhesive composition, the adhesiveness after curing, and the film thickness uniformity at the time of application, it is even more preferable that it is 50 to 10000 mPa ⁇ s, and 100 to 5000 mPa ⁇ s. Is most preferred.
- the viscosity is a value of viscosity measured at 25 ° C. under the conditions of a sample volume of 0.4 mL and a 3 ° cone using an EHD type rotational viscometer manufactured by Tokyo Keiki Seisakusho.
- the liquid semiconductor adhesive composition of the present invention can form a thin adhesive layer.
- the adhesive composition is applied at a temperature of 25 ° C.
- the film thickness after exposure is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less from the viewpoint of reducing the stress, and the film thickness uniformity. From the viewpoint, it is still more preferably 20 ⁇ m or less, and most preferably 10 ⁇ m or less because the package can be made thinner.
- the film thickness is preferably 0.5 ⁇ m or more in order to ensure good thermocompression bonding and adhesion, and 1 ⁇ m or more in order to reduce defective bonding such as voids due to dust or cutting residue during dicing. It is more preferable.
- the relationship between the thickness x of the wafer and the thickness y of the adhesive layer satisfies x ⁇ y from the viewpoint of chip retention during curing (distortion due to thermal melting during curing).
- X ⁇ 2 ⁇ y is more preferable.
- the film thickness here can be measured by the following method.
- the adhesive composition was applied onto a silicon wafer by spin coating, and the obtained coating film was laminated with a release-treated PET film, and a high-precision parallel exposure machine (manufactured by Oak Manufacturing Co., Ltd., “EXM-1172-B- ⁇ ”). (Product name)), exposure is performed at 1000 mJ / cm 2 . Thereafter, the thickness of the adhesive layer is measured using a surface roughness measuring instrument (manufactured by Kosaka Laboratory).
- the adhesive composition for a liquid semiconductor of the present invention preferably has a 5% weight reduction temperature of 150 ° C. or higher, more preferably 180 ° C. or higher, of the B-staged adhesive composition by light irradiation. Most preferably, it is 200 ° C. or higher.
- the 5% weight reduction temperature is lower than 150 ° C., the adherend tends to peel off at the time of thermosetting after the adherend is bonded or at the time of heat history such as reflow, and heat drying is required before the thermocompression.
- the 5% weight reduction temperature is 500. It is preferable that it is below °C.
- the amount of the solvent contained in the adhesive composition is preferably 5% by mass or less, more preferably 3% by mass or less, and more preferably 1% by mass. Most preferably:
- the 5% weight loss temperature is a value measured as follows.
- the adhesive composition is applied onto a silicon wafer by spin coating (2000 rpm / 10 s, 4000 rpm / 20 s), and the obtained coating film is laminated with a hand roller at room temperature to obtain a high-precision coating. Exposure is performed at 1000 mJ / cm 2 using a parallel exposure machine (Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name)).
- the B-staged adhesive was measured using a differential thermothermal gravimetric simultaneous measurement apparatus (trade name “TG / DTA6300” manufactured by SII Nano Technology) with a temperature rising rate of 10 ° C./min, nitrogen flow (400 ml / Measure the 5% weight loss temperature under min).
- TG / DTA6300 manufactured by SII Nano Technology
- the B-stage of the liquid semiconductor adhesive composition of the present invention has a surface tack force of 200 gf / cm 2 at 30 ° C. after the adhesive composition is applied on a substrate and exposed from the viewpoint of handleability.
- a surface tack force of 200 gf / cm 2 at 30 ° C. after the adhesive composition is applied on a substrate and exposed from the viewpoint of handleability.
- Is preferably 150 gf / cm 2 or less from the viewpoint of adhesiveness during thermocompression bonding, more preferably 100 gf / cm 2 or less from the viewpoint of peelability of the dicing tape. From the viewpoint of properties, it is most preferably 50 gf / cm 2 or less.
- the surface tack force is 0.1 gf / cm 2 or more in order to suppress chip jumping during dicing. When the surface tack force at 30 ° C.
- the surface tack force here is a value measured as follows.
- the adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, 4000 rpm / 20 s), and the obtained coating film was laminated with a release-treated PET film, and a high-precision parallel exposure machine (manufactured by Oak Seisakusho). , “EXM-1172-B- ⁇ ” (trade name)) is exposed at 1000 mJ / cm 2 . Thereafter, the surface tack strength at 30 ° C.
- the tack force at 30 ° C. is measured five times and calculated from the average value.
- the liquid semiconductor adhesive composition of the present invention is exposed to a high precision parallel exposure machine (“EXM-1172-B- ⁇ ” (trade name) manufactured by Oak Manufacturing Co., Ltd.), and then exposed to a minimum temperature at 20 ° C. to 300 ° C. Those having a melt viscosity of 30000 Pa ⁇ s or less are preferred.
- the minimum melt viscosity here is a value obtained by measuring a sample after exposure with a light amount of 1000 mJ / cm 2 using a viscoelasticity measuring device ARES (manufactured by Rheometrics Scientific F.E.). The minimum melt viscosity at 20 ° C to 300 ° C is shown.
- the measurement plate is a parallel plate having a diameter of 8 mm, the measurement conditions are a temperature increase of 5 ° C./min, the measurement temperature is 20 ° C. to 300 ° C., and the frequency is 1 Hz.
- the minimum melt viscosity is more preferably 10000 Pa ⁇ s or less from the viewpoint of thermocompression bonding, more preferably 5000 Pa ⁇ s or less from the viewpoint that thermocompression bonding can be performed when forming a thin film, and thermocompression bonding at a lower temperature and in a shorter time. It is particularly preferable that the pressure is 3000 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 handling property and imparting adhesiveness when heated.
- the liquid semiconductor adhesive composition of the present invention is B-staged by light irradiation, and the 5% weight reduction temperature after heat curing is 260 ° C. or higher in terms of suppressing peeling due to thermal history. It is more preferable that it is 280 ° C. or higher in terms of suppressing voids due to heat history, and most preferably 300 ° C. or higher from the viewpoint of moisture absorption reflow resistance. If the 5% weight loss temperature is less than 260 ° C., peeling tends to occur due to a thermal history such as a reflow process.
- the liquid semiconductor adhesive composition of the present invention can suppress delamination by the amount of outgas when heated in an oven at 140 ° C. for 1 hour and then at 180 ° C. for 3 hours after being B-staged (during heat curing). It is preferably 10% or less in terms of point, more preferably 7% or less in terms of suppressing voids, and most preferably 5% or less in terms of further suppressing voids and peeling due to heat history after curing. preferable. When the amount of outgas exceeds 10%, voids and separation tend to occur during heat curing.
- the outgas amount here is a value measured as follows.
- the adhesive composition is applied onto a silicon wafer by spin coating (2000 rpm / 10 s, 4000 rpm / 20 s), and the obtained coating film is laminated with a hand roller at room temperature to obtain a high-precision coating. Exposure is performed at 1000 mJ / cm 2 using a parallel exposure machine (Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name)). Thereafter, the temperature of the B-staged adhesive was increased under a nitrogen flow (400 ml / min) using a differential thermothermal gravimetric simultaneous measurement apparatus (product name “TG / DTA6300” manufactured by SII Nano Technology).
- the liquid semiconductor adhesive composition of the present invention is preferably used so as to be subjected to a thermosetting treatment at 100 to 150 ° C. for 5 to 120 minutes after B-staging and thermocompression bonding.
- thermosetting treatment By such thermosetting treatment, voids and separation due to a high-temperature heat history process at 170 ° C. or higher can be suppressed, and a highly reliable semiconductor device can be obtained.
- the adhesive composition for a liquid semiconductor according to the present invention has an adhesive layer composed of an adhesive composition formed on an adherend, and the shear adhesive strength at 260 ° C. at the stage where the semiconductor element is bonded is peeled off due to thermal history.
- the shear adhesive strength is preferably 50 MPa or less. In order to set the shear bond strength at 260 ° C. to 50 MPa or more, it is necessary to blend a large amount of thermosetting components and inorganic particles, and the film thickness uniformity after coating and the storage stability of the adhesive composition are impaired, In addition, the stress after thermosetting tends to increase.
- the shear adhesive strength here, a silicon wafer on which an adhesive composition is formed is prepared in the same manner as when measuring the film thickness, the entire surface of the adhesive film is exposed, and the silicon wafer is cut into 3 ⁇ 3 mm squares.
- the cut silicon chip with adhesive is placed on a silicon chip that has been cut into 5 ⁇ 5 mm squares, and pressed with pressure of 200 gf for 2 seconds at 120 ° C. Thereafter, it is heated in an oven at 140 ° C. for 1 hour and then at 180 ° C. for 3 hours to obtain an adhesive sample.
- the shear adhesive strength at 260 ° C. was measured using a shear adhesive strength tester “Dage-4000” (trade name), and this was used as the value of the shear adhesive strength.
- Step 1 A peelable adhesive tape (back grind tape) 4 is laminated on the circuit surface S1 of the semiconductor chip (semiconductor element) 2 formed in the semiconductor wafer 1 (see FIG. 1).
- Step 2 The semiconductor wafer 1 is polished from the surface (back surface) S2 opposite to the circuit surface S1 to thin the semiconductor wafer 1 (see FIG. 2).
- Step 3 The liquid semiconductor adhesive composition 5 of the present invention is applied to the surface S2 of the semiconductor wafer 1 opposite to the circuit surface S1 (see FIGS. 3 and 4).
- Process 4 It exposes from the adhesive layer 5 side which consists of the apply
- Step 5 A peelable adhesive tape (dicing tape) 6 is laminated on the adhesive layer 5 (see FIG. 6).
- Step 6 The peelable adhesive tape 4 is peeled off (see FIG. 7).
- Step 7 The semiconductor wafer 1 is cut into a plurality of semiconductor chips (semiconductor elements) 2 by dicing (see FIG. 8).
- Step 8 The semiconductor chip 2 is picked up and pressure-bonded (mounted) to the semiconductor device support member (semiconductor element mounting support member) 7 or the semiconductor chip (see FIGS. 9, 10, and 11).
- Step 9 The mounted semiconductor chip is connected to an external connection terminal on the support member 7 through the wire 16 (see FIG. 12).
- Step 10 A stacked body including a plurality of semiconductor chips 2 is sealed with a sealing material 17 to obtain a semiconductor device 100 (see FIG. 13).
- Step 1 (Step 1) to (Step 10) will be described in detail.
- a peelable adhesive tape 4 is laminated on the circuit surface S1 side of the semiconductor wafer 1 on which a circuit is formed. Lamination of the adhesive tape 4 can be performed by a method of laminating a film previously formed into a film shape.
- Process 2 The surface S2 opposite to the adhesive tape 4 of the semiconductor wafer 1 is polished to thin the semiconductor wafer 1 to a predetermined thickness. Polishing is performed using a grinding apparatus 8 in a state where the semiconductor wafer 1 is fixed to a polishing jig by an adhesive tape 4.
- the liquid semiconductor adhesive composition 5 of the present invention is applied to the surface S2 of the semiconductor wafer 1 opposite to the circuit surface S1.
- the application can be performed in a state where the semiconductor wafer 1 to which the adhesive tape 4 is attached is fixed to the jig 21 in the box 20.
- the coating method is selected from a printing method, a spin coating method, a spray coating method, a jet dispensing method, an ink jet method, and the like.
- the spin coat method (FIG. 3) and the spray coat method (FIG. 4) are preferable from the viewpoints of thinning and film thickness uniformity.
- a hole may be formed in the suction table included in the spin coater, or the suction table may be mesh-shaped.
- the suction table has a mesh shape from the point that adsorption marks are difficult to remain.
- Application by spin coating is preferably performed at a rotational speed of 500 to 5000 rpm in order to prevent the wafer from undulating and the edge from rising. From the same viewpoint, the rotational speed is more preferably 1000 to 4000 rpm.
- the spin coater can be provided with a temperature controller.
- the adhesive composition can be stored with a syringe or the like, and a temperature controller may be provided in the syringe set portion of the spin coater.
- an unnecessary adhesive composition may adhere to the edge portion of the semiconductor wafer.
- Such unnecessary adhesive can be removed by washing with a solvent after spin coating.
- a cleaning method is not particularly limited, but a method of discharging a solvent from a nozzle to a portion where an unnecessary adhesive is attached while spinning a semiconductor wafer is preferable. Any solvent may be used for the cleaning as long as it dissolves the adhesive.
- a low boiling point solvent selected from methyl ethyl ketone, acetone, isopropyl alcohol and methanol is used.
- Actinic rays are irradiated from the side of the adhesive layer 5 formed from the liquid semiconductor adhesive composition of the present invention by coating to make the adhesive composition B-staged.
- the adhesive layer 5 is fixed on the semiconductor wafer 1 and tack on the surface of the adhesive layer 5 can be reduced.
- the exposure can be performed in an atmosphere such as a vacuum, nitrogen, or air.
- exposure can be performed in a state where a substrate such as a PET film or a polypropylene film subjected to a release treatment is laminated on the adhesive layer 5.
- the process 5 can also be simplified by exposing in the state which laminated
- FIG. It is also possible to perform exposure through a patterned mask. Exposure can also be performed through a patterned mask. By using a patterned mask, it is possible to form adhesive layers having different fluidity during thermocompression bonding, or to obtain an adhesive pattern by development.
- the exposure amount is preferably 20 to 2000 mJ / cm 2 from the viewpoint of tack reduction and tact time. Moreover, you may heat at the temperature of 100 degrees C or less after exposure for the purpose of the tack
- the film thickness after exposure is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less from the viewpoint of reducing stress, and even more preferably 20 ⁇ m or less from the viewpoint of film thickness uniformity. Since it can be thinned, it is most preferably 10 ⁇ m or less.
- the film thickness is preferably 0.5 ⁇ m or more in order to ensure good thermocompression bonding and adhesion, and 1 ⁇ m or more in order to reduce defective bonding such as voids due to dust or cutting residue during dicing. It is more preferable.
- the film thickness can be measured in the same manner as described above.
- the relationship between the thickness x of the wafer and the thickness y of the adhesive layer preferably satisfies x ⁇ y, and more preferably satisfies x ⁇ 2 ⁇ y.
- the surface tackiness at 30 ° C. is 200 gf / cm 2 or less, more preferably 150 gf / cm 2 or less from the viewpoint of tackiness at the time of thermal compression bonding, the dicing tape peeling still more preferred from the viewpoint of sex is 100 gf / cm 2 or less, and most preferable from the viewpoint of pickup property is 50 gf / cm 2 or less.
- the surface tack force is 0.1 gf / cm 2 or more in order to suppress chip jumping during dicing. The surface tack force can be measured in the same manner as described above.
- a peelable adhesive tape 6 such as a dicing tape is attached to the adhesive layer 5.
- the adhesive tape 6 can be attached by a method of laminating an adhesive tape previously formed into a film shape.
- Step 6 Subsequently, the adhesive tape 4 attached to the circuit surface of the semiconductor wafer 1 is peeled off.
- an adhesive tape whose adhesiveness is reduced by irradiation with actinic rays typically ultraviolet rays
- it can be peeled off.
- Step 7 The semiconductor wafer 1 is cut along with the adhesive layer 5 along the dicing line D.
- the semiconductor wafer 1 is cut into a plurality of semiconductor chips 2 each provided with an adhesive layer 5 on the back surface.
- Dicing is performed using a dicing blade 11 in a state where the whole is fixed to a frame (wafer ring) 10 with an adhesive tape (dicing tape) 6.
- the cut semiconductor chip 2 is picked up together with the adhesive layer 5 by the die bonding apparatus 12, that is, the semiconductor element with the adhesive layer is picked up, and a support member for semiconductor device (support member for mounting semiconductor elements) 7 Alternatively, it is pressure-bonded (mounted) to another semiconductor chip 2.
- the pressure bonding is preferably performed while heating.
- the shear bond strength at 260 ° C. between the semiconductor chip and the supporting member or other semiconductor chip is preferably 0.2 MPa or more, more preferably 0.5 MPa or more in terms of suppressing peeling due to thermal history, Most preferred is 1.0 MPa or more from the viewpoint of moisture absorption reflow resistance.
- the shear adhesive strength is preferably 50 MPa or less. The shear bond strength can be measured in the same manner as described above.
- each semiconductor chip 2 is connected to an external connection terminal on the support member 7 through a wire 16 connected to the bonding pad.
- the semiconductor device 100 is obtained by sealing the stacked body including the semiconductor chip 2 with the sealing material 17.
- a semiconductor device having a structure in which semiconductor elements and / or a semiconductor element and a semiconductor element mounting support member are bonded is manufactured by the liquid semiconductor adhesive composition of the present invention. be able to.
- the configuration and the manufacturing method of the semiconductor device are not limited to the above embodiment, and can be appropriately changed without departing from the gist of the present invention.
- the order of steps 1 to 7 can be changed as necessary.
- the adhesive composition for a liquid semiconductor of the present invention is applied to the back surface of a semiconductor wafer that has been diced in advance, and then irradiated with actinic rays (typically ultraviolet rays) to form the adhesive composition B. It can also be staged. At this time, a patterned mask can also be used.
- the applied adhesive composition may be heated to 120 ° C. or lower, preferably 100 ° C. or lower, more preferably 80 ° C. or lower before or after exposure. Thereby, the remaining solvent and moisture can be reduced, and tack after exposure can be further reduced.
- thermoplastic resin Preparation of thermoplastic resin>.
- P-1 In a flask equipped with a stirrer, a thermometer, and a nitrogen substitution device, MBA (made by Wakayama Seika, trade name “MBAA”, molecular weight 286), which is a diamine, was 5.72 g (0.02 mol), “D-400” ( Trade name “D-400” (molecular weight: 433), manufactured by BASF) 13.57 g (0.03 mol), 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane ( 2.48 g (0.01 mol) of trade name “BY16-871EG”, manufactured by Toray Dow Corning Co., Ltd., and 1,4-butanediol bis (3-aminopropyl) ether (trade name “B-12”, Tokyo Chemical Industry, molecular weight 204.31) 8.17 g (0.04 mol) and NMP 110 g as a solvent were charged and stirred to dissolve
- the obtained polyimide varnish was purified by reprecipitation three times using pure water, and dried by heating at 60 ° C. for 3 days using a vacuum oven to obtain a polyimide solid.
- M-140 N-acryloyloxyethyl hexahydrophthalimide (5% weight loss temperature: 200 ° C., viscosity at 25 ° C .: 450 mPa ⁇ s) manufactured by Toa Gosei Co., Ltd.
- AMP-20GY manufactured by Shin-Nakamura Chemical Co., Ltd., phenoxydiethylene glycol acrylate (5% weight loss temperature: 175 ° C., viscosity at 25 ° C .: 16 mPa ⁇ s).
- A-BPE4 Shin-Nakamura Chemical Co., Ltd., ethoxylated bisphenol A acrylate (5% weight loss temperature: 330 ° C., viscosity at 25 ° C .: 980 mPa ⁇ s).
- I-651 manufactured by Ciba Japan, 2,2-dimethoxy-1,2-diphenylethane-1-one (5% weight loss temperature: 170 ° C., molecular extinction coefficient at 365 nm: 400 ml / g ⁇ cm).
- I-379EG Ciba Japan, 2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one (morpholine skeleton-containing photoinitiator Agent, 5% weight loss temperature: 260 ° C., molecular extinction coefficient at 365 nm: 8000 ml / g ⁇ cm).
- I-907 Ciba Japan, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one (morpholine skeleton-containing photoinitiator, 5% weight loss temperature: 220 C., molecular extinction coefficient at 365 nm: 450 ml / g ⁇ cm).
- I-OXE01 manufactured by Ciba Japan, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] (oxime ester skeleton-containing photoinitiator, 5% weight loss temperature: 220 ° C. at 365 nm Molecular extinction coefficient: 7000 ml / g ⁇ cm).
- I-OXE02 Etanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime), (oxime ester, manufactured by Ciba Japan Skeleton-containing photoinitiator, 5% weight loss temperature: 370 ° C., molecular extinction coefficient at 365 nm: 7700 ml / g ⁇ cm).
- DAROCUR-1173 manufactured by Ciba Japan, 2-hydroxy-2-methyl-1-phenyl-propan-1-one (5% weight loss temperature: 110 ° C., molecular extinction coefficient at 365 nm: 80 ml / g ⁇ cm) .
- DAROCUR-EHA 2-ethylhexyl-4-dimethylaminobenzoate (5% weight loss temperature: 150 ° C., molecular extinction coefficient at 365 nm: ⁇ 50 ml / g ⁇ cm) manufactured by Ciba Japan.
- YDF-8170C manufactured by Tohto Kasei Co., Ltd., bisphenol F type bisglycidyl ether (5% weight loss temperature: 270 ° C., viscosity at 25 ° C .: 1300 mPa ⁇ s).
- 1032H60 manufactured by Japan Epoxy Resin Co., Ltd., tris (hydroxyphenyl) methane type solid epoxy resin (5% weight loss temperature: 350 ° C., solid, melting point 60 ° C.).
- 2PHZ-PW 2-phenyl-4,5-dihydroxymethylimidazole (average particle diameter: about 3 ⁇ m) manufactured by Shikoku Chemicals.
- 1B2PZ 1-benzyl-2-phenylimidazole manufactured by Shikoku Kasei Co., Ltd. Park Mill D: Dicumyl peroxide (manufactured by NOF Corporation, 1 minute half-life temperature: 175 ° C.)
- the above 5% weight loss temperature is measured using a differential thermothermal gravimetric simultaneous measurement apparatus (product name “TG / DTA6300” manufactured by SII Nano Technology) with a heating rate of 10 ° C./min, nitrogen flow ( 400 ml / min).
- the above viscosity was measured at 25 ° C. under the conditions of a sample volume of 0.4 mL and a 3 ° cone using an EHD type rotational viscometer manufactured by Tokyo Keiki Seisakusho.
- the molecular extinction coefficient was determined by preparing a 0.001 mass% acetonitrile solution of the sample, placing the solution in a quartz cell, and measuring the spectrophotometer (Hitachi High-Technologies Corp., “U-” at room temperature (25 ° C.) under air. 3310 "(trade name)) and the absorbance was measured.
- the adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s).
- the obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name)). It was. Thereafter, the thickness of the adhesive layer was measured using a surface roughness measuring device (manufactured by Kosaka Laboratory).
- ⁇ Tack after light irradiation (surface tack force)>
- the adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s).
- the obtained coating film was laminated with a release-treated PET film, and 1000 mJ with a high-precision parallel exposure machine (manufactured by Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name), strength: 13 mW / cm 2 ). The exposure was performed at / cm 2 . Thereafter, the surface tack strength at 30 ° C.
- the adhesive composition was applied onto a polyethylene terephthalate (PET) film using an applicator so as to have a film thickness of 30 ⁇ m. 1172-B- ⁇ ”(trade name), intensity: 10 mW / cm 2 ), respectively, were exposed at 100, 200, 500, and 1000 mJ / cm 2 . After performing these predetermined amounts of exposure, the exposure amount at which the surface tack force at 30 ° C. measured by the above method was 200 gf / cm 2 or less was defined as the B-stage minimum required light amount (mJ / cm 2 ). Further, the required time at that time was defined as the B stage shortest required time (s).
- the adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s).
- the obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name)).
- a silicon wafer was cut into a 3 ⁇ 3 mm square.
- the cut silicon chip with adhesive was placed on a silicon chip that had been cut into 5 ⁇ 5 mm squares, and pressure-bonded at 120 ° C. for 2 seconds while being pressurized with 200 gf.
- shear adhesive strength at room temperature was measured using a shear adhesive strength tester “Dage-4000” (trade name) (measurement conditions, speed: 50 ⁇ m / sec, height: 50 ⁇ m), and 1 MPa or more And those below 1 MPa were designated as “C”.
- the adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s).
- the obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B- ⁇ ” (trade name)).
- a silicon wafer was cut into a 3 ⁇ 3 mm square.
- the cut silicon chip with adhesive was placed on a silicon chip that had been cut into 5 ⁇ 5 mm squares, and pressure-bonded at 120 ° C. for 2 seconds while being pressurized with 100 gf.
- the shear adhesive strength at 260 ° C. was measured using a shear adhesive strength tester “Dage-4000” (trade name) (measurement conditions, speed: 50 ⁇ m / sec, height: 50 ⁇ m). This was taken as the value of the shear bond strength.
- SYMBOLS 1 ... Semiconductor wafer, 2 ... Semiconductor chip, 4 ... Adhesive tape (back grind tape), 5 ... Adhesive composition (adhesive layer), 6 ... Adhesive tape (dicing tape), 7 ... Support member, 8 ... Grinding device DESCRIPTION OF SYMBOLS 9 ... Exposure apparatus, 10 ... Wafer ring, 11 ... Dicing blade, 12 ... Die bonding apparatus, 14, 15 ... Hot plate, 16 ... Wire, 17 ... Sealing material, 18 ... Connection terminal, 100 ... Semiconductor device, S1 ... Circuit surface of the semiconductor wafer, S2... Back surface of the semiconductor wafer.
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Abstract
Description
工程1:半導体ウェハ1内に形成された半導体チップ(半導体素子)2の回路面S1上にはく離可能な粘着テープ(バックグラインドテープ)4を積層する(図1を参照)。
工程2:半導体ウェハ1を回路面S1とは反対側の面(裏面)S2から研磨して半導体ウェハ1を薄くする(図2を参照)。
工程3:半導体ウェハ1の回路面S1とは反対側の面S2に本発明の液状半導体用接着剤組成物5を塗布する(図3及び4を参照)。
工程4:塗布された接着剤組成物からなる接着剤層5側から露光を行い、接着剤層5をBステージ化する(図5を参照)。
工程5:接着剤層5上にはく離可能な粘着テープ(ダイシングテープ)6を積層する(図6を参照)。
工程6:はく離可能な粘着テープ4をはく離する(図7を参照)。
工程7:半導体ウェハ1をダイシングにより複数の半導体チップ(半導体素子)2に切り分ける(図8を参照)。
工程8:半導体チップ2をピックアップして半導体装置用の支持部材(半導体素子搭載用支持部材)7または半導体チップに圧着(マウント)する(図9、10、11を参照)。
工程9:マウントされた半導体チップを、ワイヤ16を介して支持部材7上の外部接続端子と接続する(図12を参照)。
工程10:複数の半導体チップ2を含む積層体を封止材17によって封止して、半導体装置100を得る(図13を参照)。 1 to 13 are schematic views showing an embodiment of a method for manufacturing a semiconductor device. The manufacturing method according to the present embodiment includes the following steps.
Step 1: A peelable adhesive tape (back grind tape) 4 is laminated on the circuit surface S1 of the semiconductor chip (semiconductor element) 2 formed in the semiconductor wafer 1 (see FIG. 1).
Step 2: The
Step 3: The liquid
Process 4: It exposes from the
Step 5: A peelable adhesive tape (dicing tape) 6 is laminated on the adhesive layer 5 (see FIG. 6).
Step 6: The peelable
Step 7: The
Step 8: The
Step 9: The mounted semiconductor chip is connected to an external connection terminal on the
Step 10: A stacked body including a plurality of
表面に回路を形成した半導体ウェハ1の回路面S1側にはく離可能な粘着テープ4を積層する。粘着テープ4の積層は、予めフィルム状に成形されたフィルムをラミネートする方法により行なうことができる。 (Process 1)
A peelable
半導体ウェハ1の粘着テープ4とは反対側の面S2を研磨して、半導体ウェハ1を所定の厚さまで薄くする。研磨は、粘着テープ4によって半導体ウェハ1を研磨用の治具に固定した状態で、グラインド装置8を用いて行う。 (Process 2)
The surface S2 opposite to the
半導体ウェハ1の回路面S1とは反対側の面S2に本発明の液状半導体用接着剤組成物5を塗布する。塗布は、ボックス20内で、粘着テープ4が貼り付けられた半導体ウェハ1を治具21に固定した状態で行うことができる。塗布方法は、印刷法、スピンコート法、スプレーコート法、ジェットディスペンス法及びインクジェット法などから選ばれる。これらの中でも、薄膜化及び膜厚均一性の観点から、スピンコート法(図3)やスプレーコート法(図4)が好ましい。スピンコート装置が有する吸着台には穴が形成されていてもよいし、吸着台がメッシュ状であってもよい。吸着痕が残りにくい点から、吸着台はメッシュ状であることが好ましい。スピンコート法による塗布は、ウェハのうねり、及びエッジ部の盛り上がりを防止するために、500~5000rpmの回転数で行うことが好ましい。同様の観点から、回転数は1000~4000rpmがさらに好ましい。接着剤組成物の粘度を調整する目的でスピンコート台に温度調節器を備えることもできる。 (Process 3)
The liquid
塗布により本発明の液状半導体用接着剤組成物から形成された接着剤層5側から活性光線(典型的には紫外線)を照射して、接着剤組成物をBステージ化する。これにより接着剤層5が半導体ウェハ1上に固定されるとともに、接着剤層5表面のタックを低減することができる。露光は、真空下、窒素下、空気下などの雰囲気下で行なうことができる。酸素阻害を低減するために、離形処理されたPETフィルムやポリプロピレンフィルムなどの基材を接着剤層5上に積層した状態で、露光することもできる。また、ポリ塩化ビニル、ポリオレフィンや粘着テープ(ダイシングテープ)6を接着剤層5上に積層した状態で露光することにより工程5を簡略化することもできる。また、パターニングされたマスクを介して露光を行うこともできる。パターニングされたマスクを介して露光を行うこともできる。パターニングされたマスクを用いることにより、熱圧着時の流動性が異なる接着剤層を形成させることができたり、現像によって接着剤パターンを得ることができる。露光量は、タック低減及びタクトタイムの観点から、20~2000mJ/cm2が好ましい。また、Bステージ化後のタック低減及びアウトガス低減を目的に、露光後100℃以下の温度で加熱を行なってもよい。 (Process 4)
Actinic rays (typically ultraviolet rays) are irradiated from the side of the
露光後、接着剤層5にダイシングテープなどのはく離可能な粘着テープ6を貼り付ける。粘着テープ6は、予めフィルム状に成形された粘着テープをラミネートする方法により貼り付けることができる。 (Process 5)
After the exposure, a peelable
続いて、半導体ウェハ1の回路面に貼り付けられた粘着テープ4をはく離する。例えば、活性光線(典型的には紫外線)を照射することによって粘着性が低下する粘着テープを使用し、粘着テープ4側から露光した後、これをはく離することができる。 (Step 6)
Subsequently, the
ダイシングラインDに沿って半導体ウェハ1を接着剤層5とともに切断する。このダイシングにより、半導体ウェハ1が、それぞれの裏面に接着剤層5が設けられた複数の半導体チップ2に切り分けられる。ダイシングは、粘着テープ(ダイシングテープ)6によって全体をフレーム(ウェハリング)10に固定した状態でダイシングブレード11を用いて行われる。 (Step 7)
The
ダイシングの後、切り分けられた半導体チップ2を、ダイボンド装置12によって接着剤層5とともにピックアップし、すなわち接着剤層付き半導体素子をピックアップし、半導体装置用の支持部材(半導体素子搭載用支持部材)7または他の半導体チップ2に圧着(マウント)する。圧着は加熱しながら行なうことが好ましい。 (Process 8)
After dicing, the
工程8の後、それぞれの半導体チップ2はそのボンディングパッドに接続されたワイヤ16を介して支持部材7上の外部接続端子と接続される。 (Step 9)
After
半導体チップ2を含む積層体を封止材17によって封止することにより、半導体装置100が得られる。 (Process 10)
The
(P-1)
撹拌機、温度計及び窒素置換装置を備えたフラスコ内に、ジアミンであるMBAA(和歌山精化製、商品名「MBAA」、分子量286)5.72g(0.02mol)、「D-400」(商品名「D-400」(分子量:433)、BASF製)13.57g(0.03mol)、1,1,3,3-テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン(商品名「BY16-871EG」、東レ・ダウコーニング(株)製)2.48g(0.01mol)、及び1,4-ブタンジオール ビス(3-アミノプロピル)エーテル(商品名「B-12」、東京化成製、分子量204.31)8.17g(0.04mol)と、溶媒であるNMP110gを仕込み、撹拌してジアミンを溶媒に溶解させた。 <(E) component: Preparation of thermoplastic resin>.
(P-1)
In a flask equipped with a stirrer, a thermometer, and a nitrogen substitution device, MBA (made by Wakayama Seika, trade name “MBAA”, molecular weight 286), which is a diamine, was 5.72 g (0.02 mol), “D-400” ( Trade name “D-400” (molecular weight: 433), manufactured by BASF) 13.57 g (0.03 mol), 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane ( 2.48 g (0.01 mol) of trade name “BY16-871EG”, manufactured by Toray Dow Corning Co., Ltd., and 1,4-butanediol bis (3-aminopropyl) ether (trade name “B-12”, Tokyo Chemical Industry, molecular weight 204.31) 8.17 g (0.04 mol) and NMP 110 g as a solvent were charged and stirred to dissolve the diamine in the solvent.
撹拌機、温度計及び窒素置換装置(窒素流入管)を備えた500mLフラスコ内に、ジアミンであるポリオキシプロピレンジアミン(商品名「D-2000」(分子量:約2000)、BASF製)140g(0.07mol)、及び1,1,3,3-テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン(商品名「BY16-871EG」、東レ・ダウコーニング(株)製)3.72g(0.015mol)に、ODPA31.0g(0.1mol)を、フラスコ内の溶液に少量ずつ添加した。添加終了後、室温で5時間撹拌した。その後、フラスコに水分受容器付きの還流冷却器を取り付け、窒素ガスを吹き込みながら溶液を180℃に昇温させて5時間保温し水を除去して、液状ポリイミド樹脂(P-2)を得た。(P-2)のGPC測定を行ったところ、ポリスチレン換算で重量平均分子量(Mw)=40000であった。また、(P-2)のTgは20℃以下であった。 (P-2)
In a 500 mL flask equipped with a stirrer, a thermometer, and a nitrogen displacement device (nitrogen inflow pipe), 140 g (0 of polyoxypropylenediamine (trade name “D-2000” (molecular weight: about 2000), manufactured by BASF) as a diamine) .07 mol) and 1,1,3,3-tetramethyl-1,3-bis (3-aminopropyl) disiloxane (trade name “BY16-871EG”, manufactured by Toray Dow Corning Co., Ltd.) 3.72 g (0.015 mol), 31.0 g (0.1 mol) of ODPA was added to the solution in the flask little by little. After completion of the addition, the mixture was stirred at room temperature for 5 hours. Thereafter, a reflux condenser with a moisture acceptor was attached to the flask, and the solution was heated to 180 ° C. while blowing nitrogen gas, and kept for 5 hours to remove water, thereby obtaining a liquid polyimide resin (P-2). . When the GPC measurement of (P-2) was performed, the weight average molecular weight (Mw) was 40000 in terms of polystyrene. Further, the Tg of (P-2) was 20 ° C. or less.
上記で得られたポリイミド樹脂(P-1)及び(P-2)を用いて、下記表1~3に示す組成比(単位:質量部)にて各成分を配合し、実施例1~11の接着剤組成物及び比較例1~5の接着剤組成物(接着剤層形成用組成物)を得た。 <Preparation of adhesive composition>
Using the polyimide resins (P-1) and (P-2) obtained above, the respective components were blended at the composition ratios (unit: parts by mass) shown in Tables 1 to 3 below. Examples 1 to 11 And adhesive compositions (compositions for forming an adhesive layer) of Comparative Examples 1 to 5 were obtained.
M-140:東亜合成社製、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(5%重量減少温度:200℃、25℃での粘度:450mPa・s)。
AMP-20GY:新中村化学工業社製、フェノキシジエチレングリコールアクリレート(5%重量減少温度:175℃、25℃での粘度:16mPa・s)。
A-BPE4:新中村化学工業社製、エトキシ化ビスフェノールA型アクリレート(5%重量減少温度:330℃、25℃での粘度:980mPa・s)。
I-651:チバ・ジャパン社製、2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン(5%重量減少温度:170℃、365nmでの分子吸光係数:400ml/g・cm)。
I-379EG:チバ・ジャパン社製、2-ジメチルアミノ-2-(4-メチルーベンジル)-1-(4-モルフォリン-4-イルーフェニル)-ブタンー1-オン(モルフォリン骨格含有光開始剤、5%重量減少温度:260℃、365nmでの分子吸光係数:8000ml/g・cm)。
I-907:チバ・ジャパン社製、2-メチル-1-(4-(メチルチオ)フェニル)-2-モルフォリノプロパン-1―オン(モルフォリン骨格含有光開始剤、5%重量減少温度:220℃、365nmでの分子吸光係数:450ml/g・cm)。
I-OXE01:チバ・ジャパン社製、1-[4-(フェニルチオ)―,2-(O-ベンゾイルオキシム)](オキシムエステル骨格含有光開始剤、5%重量減少温度:220℃、365nmでの分子吸光係数:7000ml/g・cm)。
I-OXE02:チバ・ジャパン社製、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(o-アセチルオキシム)、(オキシムエステル骨格含有光開始剤、5%重量減少温度:370℃、365nmでの分子吸光係数:7700ml/g・cm)。
DAROCUR-1173:チバ・ジャパン社製、2-ヒドロキシ-2-メチル-1-フェニループロパンー1-オン(5%重量減少温度:110℃、365nmでの分子吸光係数:80ml/g・cm)。
DAROCUR-EHA:チバ・ジャパン社製、2-エチルヘキシル-4-ジメチルアミノベンゾエート(5%重量減少温度:150℃、365nmでの分子吸光係数:<50ml/g・cm)。
YDF-8170C:東都化成社製、ビスフェノールF型ビスグリシジルエーテル(5%重量減少温度:270℃、25℃での粘度:1300mPa・s)。
1032H60:ジャパンエポキシレジン社製、トリス(ヒドロキシフェニル)メタン型固形エポキシ樹脂(5%重量減少温度:350℃、固形、融点60℃)。
2PHZ-PW:四国化成社製、2-フェニル-4,5-ジヒドロキシメチルイミダゾール(平均粒子径:約3μm)。
1B2PZ:四国化成社製、1-ベンジル-2-フェニルイミダゾール。
パークミルD:日油社製、ジクミルパーオキサイド(1分間半減期温度:175℃)。 In Tables 1 to 3, each symbol means the following.
M-140: N-acryloyloxyethyl hexahydrophthalimide (5% weight loss temperature: 200 ° C., viscosity at 25 ° C .: 450 mPa · s) manufactured by Toa Gosei Co., Ltd.
AMP-20GY: manufactured by Shin-Nakamura Chemical Co., Ltd., phenoxydiethylene glycol acrylate (5% weight loss temperature: 175 ° C., viscosity at 25 ° C .: 16 mPa · s).
A-BPE4: Shin-Nakamura Chemical Co., Ltd., ethoxylated bisphenol A acrylate (5% weight loss temperature: 330 ° C., viscosity at 25 ° C .: 980 mPa · s).
I-651: manufactured by Ciba Japan, 2,2-dimethoxy-1,2-diphenylethane-1-one (5% weight loss temperature: 170 ° C., molecular extinction coefficient at 365 nm: 400 ml / g · cm).
I-379EG: Ciba Japan, 2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one (morpholine skeleton-containing photoinitiator Agent, 5% weight loss temperature: 260 ° C., molecular extinction coefficient at 365 nm: 8000 ml / g · cm).
I-907: Ciba Japan, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one (morpholine skeleton-containing photoinitiator, 5% weight loss temperature: 220 C., molecular extinction coefficient at 365 nm: 450 ml / g · cm).
I-OXE01: manufactured by Ciba Japan, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)] (oxime ester skeleton-containing photoinitiator, 5% weight loss temperature: 220 ° C. at 365 nm Molecular extinction coefficient: 7000 ml / g · cm).
I-OXE02: Etanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (o-acetyloxime), (oxime ester, manufactured by Ciba Japan Skeleton-containing photoinitiator, 5% weight loss temperature: 370 ° C., molecular extinction coefficient at 365 nm: 7700 ml / g · cm).
DAROCUR-1173: manufactured by Ciba Japan, 2-hydroxy-2-methyl-1-phenyl-propan-1-one (5% weight loss temperature: 110 ° C., molecular extinction coefficient at 365 nm: 80 ml / g · cm) .
DAROCUR-EHA: 2-ethylhexyl-4-dimethylaminobenzoate (5% weight loss temperature: 150 ° C., molecular extinction coefficient at 365 nm: <50 ml / g · cm) manufactured by Ciba Japan.
YDF-8170C: manufactured by Tohto Kasei Co., Ltd., bisphenol F type bisglycidyl ether (5% weight loss temperature: 270 ° C., viscosity at 25 ° C .: 1300 mPa · s).
1032H60: manufactured by Japan Epoxy Resin Co., Ltd., tris (hydroxyphenyl) methane type solid epoxy resin (5% weight loss temperature: 350 ° C., solid, melting point 60 ° C.).
2PHZ-PW: 2-phenyl-4,5-dihydroxymethylimidazole (average particle diameter: about 3 μm) manufactured by Shikoku Chemicals.
1B2PZ: 1-benzyl-2-phenylimidazole manufactured by Shikoku Kasei Co., Ltd.
Park Mill D: Dicumyl peroxide (manufactured by NOF Corporation, 1 minute half-life temperature: 175 ° C.)
東京計器製造所製のEHD型回転粘度計を用い、サンプル量0.4mL、3°コーンの条件下、25℃における粘度を測定した。 <Viscosity>
Using an EHD type rotational viscometer manufactured by Tokyo Keiki Seisakusho, the viscosity at 25 ° C. was measured under the conditions of a sample volume of 0.4 mL and a 3 ° cone.
接着剤組成物をシリコンウェハ上にスピンコート(2000rpm/10s、更に4000rpm/20s)によって塗布した。得られた塗膜に、離型処理したPETフィルムをラミネートし、高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名))により1000mJ/cm2で露光を行なった。その後、表面粗さ測定器(小坂研究所製)を用いて接着剤層の厚みを測定した。 <Film thickness>
The adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s). The obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B-∞” (trade name)). It was. Thereafter, the thickness of the adhesive layer was measured using a surface roughness measuring device (manufactured by Kosaka Laboratory).
接着剤組成物をシリコンウェハ上にスピンコート(2000rpm/10s、更に4000rpm/20s)によって塗布した。得られた塗膜に、離型処理したPETフィルムをラミネートし、高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名)、強度:13mW/cm2)により1000mJ/cm2で露光を行なった。その後、30℃での表面のタック強度を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により、30℃におけるタック力を5回測定し、その平均値を算出した。 <Tack after light irradiation (surface tack force)>
The adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s). The obtained coating film was laminated with a release-treated PET film, and 1000 mJ with a high-precision parallel exposure machine (manufactured by Oak Seisakusho, “EXM-1172-B-∞” (trade name), strength: 13 mW / cm 2 ). The exposure was performed at / cm 2 . Thereafter, the surface tack strength at 30 ° C. was measured using a probe tacking tester manufactured by Reska Co., Ltd., probe diameter: 5.1 mm, peeling speed: 10 mm / s, contact load: 100 gf / cm 2 , contact time: 1 s Thus, the tack force at 30 ° C. was measured 5 times, and the average value was calculated.
接着剤組成物をシリコンウェハ上にスピンコート(2000rpm/10s、更に4000rpm/20s)によって塗布した。得られた塗膜に、室温空気下で高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名))により1000mJ/cm2で露光を行なった。その後、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により、30℃におけるタック力を5回測定し、その平均値を算出した。 <Tack after light irradiation under air (surface tack force)>
The adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s). The obtained coating film was exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (“EXM-1172-B-∞” (trade name) manufactured by Oak Seisakusho) under room temperature air. Thereafter, using a probe tacking tester manufactured by Reska Co., Ltd., a probe diameter: 5.1 mm, a peeling speed: 10 mm / s, a contact load: 100 gf / cm 2 , a contact time: 1 s, a tack force at 30 ° C. The measurement was performed once and the average value was calculated.
接着剤組成物をポリエチレンテレフタレート(PET)フィルム上に、アプリケーターを用いて膜厚30μmとなるように塗布し、室温(25℃)空気下で、高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名)、強度:10mW/cm2)によりそれぞれ100、200、500、1000mJ/cm2の露光を行った。これら所定量の露光を行なった後、上記方法で測定した30℃での表面タック力が200gf/cm2以下となる露光量をBステージ化最低所要光量(mJ/cm2)とした。また、そのときの所要時間をBステージ化最短所要時間(s)とした。 <Minimum required amount of light for B-stage and minimum required time for B-stage>
The adhesive composition was applied onto a polyethylene terephthalate (PET) film using an applicator so as to have a film thickness of 30 μm. 1172-B-∞ ”(trade name), intensity: 10 mW / cm 2 ), respectively, were exposed at 100, 200, 500, and 1000 mJ / cm 2 . After performing these predetermined amounts of exposure, the exposure amount at which the surface tack force at 30 ° C. measured by the above method was 200 gf / cm 2 or less was defined as the B-stage minimum required light amount (mJ / cm 2 ). Further, the required time at that time was defined as the B stage shortest required time (s).
接着剤組成物をシリコンウェハ上にスピンコート(2000rpm/10s、更に4000rpm/20s)によって塗布した。得られた塗膜に、離型処理したPETフィルムをラミネートし、高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名))により1000mJ/cm2で露光を行なった後、3×3mm角にシリコンウェハを切り出した。切り出した接着剤付きシリコンチップを予め5×5mm角に切り出したシリコンチップ上に載せ、200gfで加圧しながら、120℃で2秒間圧着した。得られたサンプルについて、せん断接着力試験機「Dage-4000」(商品名)(測定条件、速度:50μm/sec、高さ:50μm)を用いて室温でのせん断接着力を測定し、1MPa以上であるものを「A」、1MPaを下回るものを「C」とした。 <Thermocompression bonding>
The adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s). The obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B-∞” (trade name)). After that, a silicon wafer was cut into a 3 × 3 mm square. The cut silicon chip with adhesive was placed on a silicon chip that had been cut into 5 × 5 mm squares, and pressure-bonded at 120 ° C. for 2 seconds while being pressurized with 200 gf. About the obtained sample, shear adhesive strength at room temperature was measured using a shear adhesive strength tester “Dage-4000” (trade name) (measurement conditions, speed: 50 μm / sec, height: 50 μm), and 1 MPa or more And those below 1 MPa were designated as “C”.
接着剤組成物をシリコンウェハ上にスピンコート(2000rpm/10s、更に4000rpm/20s)によって塗布した。得られた塗膜に、離型処理したPETフィルムをラミネートし、高精度平行露光機(オーク製作所製、「EXM-1172-B-∞」(商品名))により1000mJ/cm2で露光を行なった後、3×3mm角にシリコンウェハを切り出した。切り出した接着剤付きシリコンチップを予め5×5mm角に切り出したシリコンチップ上に載せ、100gfで加圧しながら、120℃で2秒間圧着した。その後、140℃、1時間、次いで180℃、3時間オーブンで加熱し接着サンプルを得た。得られたサンプルについて、せん断接着力試験機「Dage-4000」(商品名)(測定条件、速度:50μm/sec、高さ:50μm)を用いて260℃でのせん断接着力を測定した。これをせん断接着強度の値とした。 <260 ° C adhesive strength (shear adhesive strength)>
The adhesive composition was applied onto a silicon wafer by spin coating (2000 rpm / 10 s, further 4000 rpm / 20 s). The obtained coating film was laminated with a release-treated PET film and exposed at 1000 mJ / cm 2 with a high-precision parallel exposure machine (Oak Seisakusho, “EXM-1172-B-∞” (trade name)). After that, a silicon wafer was cut into a 3 × 3 mm square. The cut silicon chip with adhesive was placed on a silicon chip that had been cut into 5 × 5 mm squares, and pressure-bonded at 120 ° C. for 2 seconds while being pressurized with 100 gf. Thereafter, it was heated in an oven at 140 ° C. for 1 hour and then at 180 ° C. for 3 hours to obtain an adhesive sample. With respect to the obtained sample, the shear adhesive strength at 260 ° C. was measured using a shear adhesive strength tester “Dage-4000” (trade name) (measurement conditions, speed: 50 μm / sec, height: 50 μm). This was taken as the value of the shear bond strength.
Claims (11)
- (A)放射線重合性化合物、(B)光開始剤、及び(C)熱硬化性樹脂、を含み、
前記(B)成分が、(B1)波長365nmの光に対する分子吸光係数が100ml/g・cm以上である化合物を含む、液状半導体用接着剤組成物。 (A) a radiation polymerizable compound, (B) a photoinitiator, and (C) a thermosetting resin,
The liquid semiconductor adhesive composition, wherein the component (B) includes (B1) a compound having a molecular extinction coefficient of 100 ml / g · cm or more for light having a wavelength of 365 nm. - 前記液状半導体用接着剤組成物における溶剤の含有量が5質量%以下である、請求項1に記載の液状半導体用接着剤組成物。 The adhesive composition for a liquid semiconductor according to claim 1, wherein the content of the solvent in the adhesive composition for a liquid semiconductor is 5% by mass or less.
- 前記(B1)化合物が、分子内にオキシムエステル骨格又はモルホリン骨格を有する化合物である、請求項1又は2に記載の液状半導体用接着剤組成物。 The adhesive composition for a liquid semiconductor according to claim 1 or 2, wherein the (B1) compound is a compound having an oxime ester skeleton or a morpholine skeleton in the molecule.
- 前記(A)成分が、25℃で液状の単官能(メタ)アクリレートを含む、請求項1~3のいずれか一項に記載の液状半導体用接着剤組成物。 4. The liquid semiconductor adhesive composition according to claim 1, wherein the component (A) contains a monofunctional (meth) acrylate that is liquid at 25 ° C.
- (D)熱ラジカル発生剤を更に含有する、請求項1~4のいずれか一項に記載の液状半導体用接着剤組成物。 The liquid semiconductor adhesive composition according to any one of claims 1 to 4, further comprising (D) a thermal radical generator.
- (E)熱可塑性樹脂を更に含有し、当該(E)成分がイミド基を有する樹脂を含む、請求項1~5のいずれか一項に記載の液状半導体用接着剤組成物。 The liquid semiconductor adhesive composition according to any one of claims 1 to 5, further comprising (E) a thermoplastic resin, wherein the component (E) includes a resin having an imide group.
- 25℃での粘度が10~30000mPa・sである、請求項1~6のいずれか一項に記載の液状半導体用接着剤組成物。 The liquid semiconductor adhesive composition according to any one of claims 1 to 6, having a viscosity of 10 to 30,000 mPa · s at 25 ° C.
- 半導体素子同士及び/又は半導体素子と半導体素子搭載用支持部材とが請求項1~7のいずれか一項に記載の液状半導体用接着剤組成物により接着された構造を有する、半導体装置。 A semiconductor device having a structure in which semiconductor elements and / or a semiconductor element and a supporting member for mounting a semiconductor element are bonded with the adhesive composition for a liquid semiconductor according to any one of claims 1 to 7.
- 半導体ウェハの一方面上に、請求項1~7のいずれか一項に記載の液状半導体用接着剤組成物を塗布して接着剤層を設ける工程と、
前記接着剤層に光照射する工程と、
光照射された前記接着剤層とともに前記半導体ウェハを切断して接着剤層付き半導体素子を得る工程と、
前記接着剤層付き半導体素子と、他の半導体素子又は半導体素子搭載用支持部材とを、前記接着剤層付き半導体素子の接着剤層を挟んで圧着することにより接着する工程と、
を備える、半導体装置の製造方法。 Applying a liquid semiconductor adhesive composition according to any one of claims 1 to 7 on one surface of a semiconductor wafer to provide an adhesive layer;
Irradiating the adhesive layer with light;
Cutting the semiconductor wafer together with the adhesive layer irradiated with light to obtain a semiconductor element with an adhesive layer;
Bonding the semiconductor element with an adhesive layer and another semiconductor element or a support member for mounting a semiconductor element by crimping the adhesive layer of the semiconductor element with the adhesive layer, and
A method for manufacturing a semiconductor device. - 半導体素子に、請求項1~7のいずれか一項に記載の液状半導体用接着剤組成物を塗布して接着剤層を設ける工程と、
前記接着剤層に光照射する工程と、
光照射された前記接着剤層を有する前記半導体素子と、他の半導体素子又は半導体素子搭載用支持部材とを、光照射された前記接着剤層を挟んで圧着することにより接着する工程と、
を備える、半導体装置の製造方法。 Applying a liquid semiconductor adhesive composition according to any one of claims 1 to 7 to a semiconductor element to provide an adhesive layer;
Irradiating the adhesive layer with light;
Bonding the semiconductor element having the adhesive layer irradiated with light and another semiconductor element or a support member for mounting a semiconductor element by pressure bonding the adhesive layer irradiated with light; and
A method for manufacturing a semiconductor device. - 半導体素子搭載用支持部材に、請求項1~7のいずれか一項に記載の液状半導体用接着剤組成物を塗布して接着剤層を設ける工程と、
前記接着剤層に光照射する工程と、
光照射された前記接着剤層を有する前記半導体素子搭載用支持部材と、半導体素子とを、光照射された前記接着剤層を挟んで圧着することにより接着する工程と、
を備える、半導体装置の製造方法。 Applying a liquid semiconductor adhesive composition according to any one of claims 1 to 7 to a semiconductor element mounting support member to provide an adhesive layer;
Irradiating the adhesive layer with light;
Bonding the semiconductor element mounting support member having the adhesive layer irradiated with light by bonding the semiconductor element with the adhesive layer irradiated with light sandwiched therebetween;
A method for manufacturing a semiconductor device.
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CN2010800501522A CN102598233A (en) | 2009-11-13 | 2010-11-10 | Liquid adhesive composition for semiconductor, semiconductor device, and method for manufacturing semiconductor device |
JP2011540523A JPWO2011058998A1 (en) | 2009-11-13 | 2010-11-10 | Adhesive composition for liquid semiconductor, semiconductor device, and method for manufacturing semiconductor device |
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