WO2025009514A1 - 硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置及び積層体の製造方法 - Google Patents

硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置及び積層体の製造方法 Download PDF

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WO2025009514A1
WO2025009514A1 PCT/JP2024/023874 JP2024023874W WO2025009514A1 WO 2025009514 A1 WO2025009514 A1 WO 2025009514A1 JP 2024023874 W JP2024023874 W JP 2024023874W WO 2025009514 A1 WO2025009514 A1 WO 2025009514A1
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substrate
resin composition
curable resin
laminate
organic layer
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English (en)
French (fr)
Japanese (ja)
Inventor
太郎 塩島
主 國澤
颯 野元
憲一朗 佐藤
元彦 浅野
徳重 七里
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P14/00—Formation of materials, e.g. in the shape of layers or pillars
    • H10P14/40—Formation of materials, e.g. in the shape of layers or pillars of conductive or resistive materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W20/00—Interconnections in chips, wafers or substrates
    • H10W20/01—Manufacture or treatment
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W20/00—Interconnections in chips, wafers or substrates
    • H10W20/40—Interconnections external to wafers or substrates, e.g. back-end-of-line [BEOL] metallisations or vias connecting to gate electrodes

Definitions

  • the present invention relates to a curable resin composition, a cured film, a laminate, an imaging device, a semiconductor device, and a method for manufacturing a laminate.
  • a damascene process is used to form a bonding surface on the electrode surface of an element or circuit board (hereinafter simply referred to as a substrate) on which two electrodes are formed, in which a bonding electrode made of copper is surrounded by an insulating film.
  • the two substrates are then stacked so that the bonding electrodes on the bonding surfaces face each other, and a heat treatment is performed to manufacture the semiconductor device (Patent Document 1).
  • the insulating layer used to form the bonding surface is required to have high heat resistance.
  • insulating inorganic materials such as SiN and SiO2 are used as the insulating layer.
  • insulating layers made of inorganic materials are prone to warping of the substrate, and if the substrate is warped, the connection position of the electrodes may shift or the electrodes may crack when stacked, which may reduce the connection reliability of the semiconductor device.
  • the performance of semiconductor devices has improved, and substrates have become larger and thinner, making substrate warping more likely to occur, and the substrate may crack, especially when the substrate is thin.
  • the present invention aims to provide a curable resin composition that is less likely to cause wrinkles in the inorganic layer even when an inorganic layer is formed on the cured product, and that can suppress process abnormalities, a cured film of the curable resin composition, a laminate using the cured film, an imaging device and a semiconductor device having the laminate, and a method for manufacturing the laminate.
  • the present invention includes the following Disclosures 1 to 17. The present invention will be described in detail below.
  • [Disclosure 1] A curable resin composition comprising silsesquioxane, a solvent, and a silica filler as an inorganic filler, the solvent being dried at 125°C for 10 minutes, and the composition being thermally cured by heat treatment at 300°C for 1 hour, the cured product having an elastic modulus at 300°C of 0.2 MPa or more.
  • a laminate comprising an organic layer formed of the cured film according to Disclosure 8 on a first substrate, and an inorganic layer laminated on the organic layer,
  • the first substrate has a first surface having a plurality of chips and a second surface opposite thereto, and the organic layer and the inorganic layer are disposed on the first surface side of the first substrate.
  • Disclosure 10 Disclosure 10. The laminate according to Disclosure 9, wherein a supporting substrate is laminated on the inorganic layer.
  • the laminate according to Disclosure 9 or 10 further comprising a second substrate on the second surface of the first substrate, the first substrate and the second substrate being electrically connected to each other.
  • [Disclosure 12] A laminate having an organic layer and an inorganic layer, each of which is made of the cured film according to Disclosure 8, between a third substrate having an electrode and a fourth substrate having an electrode, a laminate in which the electrode of the third substrate and the electrode of the fourth substrate are electrically connected via a through hole penetrating the organic layer and the inorganic layer.
  • An imaging device having the laminate according to any one of Disclosures 9 to 13.
  • [Disclosure 15] A semiconductor device comprising the laminate according to any one of Disclosures 9 to 13.
  • [Disclosure 16] A step of applying a curable resin composition according to any one of Disclosures 1 to 6 onto a first surface of a first substrate having a first surface having a plurality of chips and a second surface opposite the first surface, and then drying the composition with a solvent and thermally curing the composition to form an organic layer; A method for producing a laminate, comprising the step of forming an inorganic layer on the organic layer.
  • [Disclosure 17] A step of applying the curable resin composition according to any one of Disclosures 1 to 6 onto a surface of a third substrate having an electrode and a fourth substrate having an electrode, and then drying the composition and thermally curing the composition to form an organic layer; forming an inorganic layer on the organic layer; forming through holes in each of the organic layer and the inorganic layer; filling each of the through holes with a conductive material; a step of polishing the surfaces of the third substrate having the electrode and the fourth substrate having the electrode, the surfaces being filled with the conductive material, to form bonding electrodes; A method for manufacturing a laminate, comprising a step of bonding a third substrate having the electrode and a fourth substrate having the electrode together so that the bonding electrodes of the third substrate and the fourth substrate are bonded to each other.
  • the curable resin composition of the present invention contains a silsesquioxane.
  • Silsesquioxane has high heat resistance while having the same degree of flexibility as organic compounds, so that by using a cured film mainly composed of silsesquioxane as the insulating layer of a laminate, it is possible to suppress warping and cracking of the substrate and improve the reliability of electrical connection.
  • the above-mentioned silsesquioxane is not particularly limited as long as it is thermosetting, but it is preferable that one molecule has a structure represented by the following structural formulas (A) and (B) in order to further suppress warping and cracking of the substrate.
  • R A and R B each independently represent an aliphatic group, an aromatic group, or hydrogen, and j and k each represent a repeating unit and an integer of 1 or more.
  • the silsesquioxane preferably has a reactive site.
  • silsesquioxane having a reactive site as the curable resin of the curable resin composition, warping and cracking of the element can be further suppressed.
  • silsesquioxane has excellent heat resistance, decomposition of the organic layer due to high-temperature treatment performed during the manufacture of a semiconductor device having multiple laminates can be further suppressed.
  • the reactive site include a hydroxyl group and an alkoxy group.
  • the content of the silsesquioxane having the reactive site is preferably 60 parts by weight or more, more preferably 70 parts by weight or more, and even more preferably 75 parts by weight or more, per 100 parts by weight of the resin solid content in the curable resin composition.
  • the content of the silsesquioxane having the reactive site is preferably less than 100 parts by weight, more preferably 90 parts by weight or less, per 100 parts by weight of the resin solid content in the curable resin composition.
  • the silsesquioxane preferably has a structure represented by the following structural formula (1).
  • the silsesquioxane has the structure of structural formula (1), warping of the element can be further suppressed.
  • the silsesquioxane further has an aromatic ring structure, since this further improves heat resistance and further suppresses warping and cracking of the element.
  • R 0 , R 1 and R 2 each independently represent a linear, branched or cyclic aliphatic group, an aromatic group or hydrogen.
  • the aliphatic group and the aromatic group may or may not have a substituent.
  • m and n each represent an integer of 1 or more.
  • R 0 each independently represents a linear, branched or cyclic aliphatic group, an aromatic group, or hydrogen.
  • the aliphatic group and the aromatic group may or may not have a substituent.
  • R 0 is preferably a phenyl group, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group, and more preferably a phenyl group.
  • R 0 is a phenyl group, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group, higher heat resistance can be exhibited.
  • R 1 and R 2 each independently represent a linear, branched or cyclic aliphatic group, an aromatic group, or hydrogen.
  • the aliphatic group and the aromatic group may or may not have a substituent.
  • R 1 and R 2 are preferably a phenyl group, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group, and more preferably a phenyl group or a methyl group.
  • R 1 and R 2 being a phenyl group, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group, higher heat resistance can be exhibited.
  • m and n are each an integer of 1 or more and represent the number of repeating units.
  • the above m is preferably 30 or more, more preferably 50 or more, and preferably 100 or less.
  • the above n is preferably 1 or more, more preferably 3 or more, and preferably 8 or less.
  • the weight average molecular weight of the silsesquioxane is not particularly limited, but is preferably 5000 to 150000. When the weight average molecular weight of the silsesquioxane is in the above range, the film-forming property during application is improved, the flattening performance is further improved, and warping and cracking of the element can be further suppressed.
  • the weight average molecular weight of the silsesquioxane is more preferably 10000 or more, even more preferably 30000 or more, more preferably 100000 or less, and even more preferably 70000 or less.
  • the weight average molecular weight of the silsesquioxane is measured as a polystyrene-equivalent molecular weight by gel permeation chromatography (GPC) using THF as an elution solvent and a Time-MB-M6.0 ⁇ 150 mm (manufactured by Waters Corporation) or an equivalent column, and can be calculated with a polystyrene standard.
  • GPC gel permeation chromatography
  • the content of the silsesquioxane is preferably 65% by weight or more and 99% by weight or less based on 100% by weight of the solid components of the curable resin composition.
  • the content of silsesquioxane in 100% by weight of the solid component of the curable resin composition is more preferably 70% by weight or more, even more preferably 75% by weight or more, more preferably 98% by weight or less, and even more preferably 97% by weight or less.
  • the curable resin composition of the present invention contains a solvent.
  • a solvent By adding a solvent to the curable resin composition, the viscosity of the silsesquioxane can be increased to a level that allows it to be applied to a substrate, and the unevenness of the substrate surface can be filled and made flat. As a result, the bonding reliability of the substrate can be increased, and the electrical connection reliability of the laminate can also be improved.
  • the solvent may be composed of a single component or a mixture of multiple components.
  • the solvent in the curable resin composition preferably has a boiling point of 130° C. or higher and 250° C. or lower.
  • the boiling point of the solvent is more preferably 150°C or higher, even more preferably 180°C or higher, more preferably 230°C or lower, and even more preferably 220°C or lower.
  • solvents having a boiling point in the above range include aromatic organic solvents, ketone organic solvents, lactam organic solvents, and lactone organic solvents.
  • R represents a hydrocarbon.
  • the compound examples include cyclopentanone (boiling point: 131° C.), propylene glycol monomethyl ether acetate (boiling point: 146° C.), anisole (boiling point: 154° C.), ethyl benzoate (boiling point: 211 to 213° C.), N-methyl-2-pyrrolidone (boiling point: 202° C.), 2-piperidone (boiling point: 256° C.), 2-pyrrolidone (boiling point: 245° C.), ⁇ -butyrolactone (boiling point: 204° C.), and ⁇ -valerolactone (boiling point: 207° C.).
  • the content of the solvent in the curable resin composition is preferably 50% by weight or less.
  • the content of the solvent in the curable resin composition is more preferably 45% by weight or less, even more preferably 40% by weight or less, and even more preferably 35% by weight or less.
  • the lower limit of the content of the solvent is not particularly limited, but is preferably 30% by weight or more from the viewpoint of further improving the flattening performance.
  • the content of the solvent is preferably 50 parts by weight or more and 100 parts by weight or less based on 100 parts by weight of the silsesquioxane.
  • the content of the solvent relative to the silsesquioxane in the above range can further improve the planarization performance of the substrate surface.
  • the content of the solvent relative to the silsesquioxane is more preferably 55 parts by weight or more, even more preferably 60 parts by weight or more, more preferably 80 parts by weight or less, and even more preferably 70 parts by weight or less.
  • the curable resin composition of the present invention contains a silica filler as an inorganic filler.
  • a silica filler in the curable resin composition and satisfying the elastic modulus described below wrinkles are less likely to occur in the inorganic layer even when an inorganic layer is formed on the cured film of the silsesquioxane, and process abnormalities due to wrinkles in the inorganic layer can be suppressed.
  • the silica filler is preferably not spherical in shape.
  • the elastic modulus is increased by the silica filler having a shape other than a perfect sphere, and the elastic modulus described later can be more easily satisfied.
  • a silica filler having a shape other than a perfect sphere it is possible to control the elastic modulus without using a crosslinking agent, and it is possible to avoid the increase in storage stability and viscosity caused by the use of a crosslinking agent in combination.
  • the reason why the elastic modulus is increased by the silica filler having a shape other than a perfect sphere is not clear, but it is thought that this is because the contact area with other fillers is small when the silica filler is a perfect sphere, making it difficult to interact with other fillers.
  • Examples of the shape of the silica filler other than a perfect sphere include needles, pulverized, and fibrous. Note that even when a perfect spherical silica filler is used, it is possible to adjust the elastic modulus to the range described later by combining it with a crosslinking agent.
  • the silica filler preferably has a bulk density of 0.01 g/cm 3 or more and 0.2 g/cm 3 or less. When the bulk density of the silica filler is in the above range, it is easier to satisfy the elastic modulus described below.
  • the bulk density of the silica filler is more preferably 0.05 g/ cm3 or more and more preferably 0.1 g/cm3 or less .
  • the content of the silica filler is preferably 15 parts by weight or more and 40 parts by weight or less based on 100 parts by weight of the silsesquioxane. By setting the content of the silica filler within the above range, it is possible to suppress warping and cracking of the substrate and to more easily satisfy the elastic modulus described below.
  • the content of the silica filler is more preferably 20 parts by weight or more, more preferably 25 parts by weight or more, more preferably 35 parts by weight or less, and even more preferably 30 parts by weight or less, relative to 100 parts by weight of the silsesquioxane.
  • the curable resin composition of the present invention preferably contains a catalyst.
  • the catalyst has a role of promoting the curing reaction.
  • the curable resin composition can be cured more completely, decomposition of the organic layer (cured film) due to high-temperature treatment can be further suppressed, and the elastic modulus can be easily controlled.
  • the catalyst include organotin compounds such as dibutyltin dilaurate and stannous acetate, metal carboxylates such as zinc naphthenate, acetylacetonate complexes with zirconium as the central metal, and titanium compounds.
  • acetylacetonate complexes with zirconium as the central metal are preferred because they can promote the curing of the curable resin composition.
  • the catalyst remains even after the curable resin composition is cured.
  • the curable resin composition of the present invention contains a catalyst
  • the cured film obtained by curing the curable resin composition also contains the catalyst.
  • the content of the catalyst is not particularly limited, but is preferably 0.01 parts by weight or more and 10 parts by weight or less per 100 parts by weight of the silsesquioxane. By setting the content of the catalyst within the above range, curing can be further promoted and decomposition of the cured film due to high-temperature treatment can be further suppressed.
  • the content of the catalyst is more preferably 0.1 parts by weight or more, even more preferably 0.2 parts by weight or more, more preferably 7 parts by weight or less, and even more preferably 5 parts by weight or less per 100 parts by weight of the silsesquioxane.
  • the curable resin composition may contain a crosslinking agent.
  • the crosslinking agent crosslinks between the curable resins, increasing the crosslink density of the cured product, and further suppressing decomposition at high temperatures. As a result, the warping and cracking of the substrate can be suppressed, and the connection reliability can be further improved.
  • the elastic modulus described below can be controlled by adjusting the blending amount and structure of the crosslinking agent. Furthermore, by containing a crosslinking agent, the elastic modulus described below can be controlled even if the shape of the silica filler is spherical.
  • crosslinking agent examples include alkoxysilane compounds such as dimethoxysilane compounds, trimethoxysilane compounds, diethoxysilane compounds, and triethoxysilane compounds, or silicate oligomers obtained by condensation of tetramethoxysilane compounds and tetraethoxysilane compounds.
  • alkoxysilane compounds such as dimethoxysilane compounds, trimethoxysilane compounds, diethoxysilane compounds, and triethoxysilane compounds
  • silicate oligomers obtained by condensation of tetramethoxysilane compounds and tetraethoxysilane compounds.
  • polyalkoxysilane is preferable from the viewpoint of improving the crosslink density and improving the heat resistance.
  • the content of the crosslinking agent is not particularly limited, but is preferably 1 part by weight or more and 50 parts by weight or less per 100 parts by weight of the silsesquioxane.
  • the content of the crosslinking agent is more preferably 3 parts by weight or more, even more preferably 3.2 parts by weight or more, more preferably 30 parts by weight or less, and even more preferably 20 parts by weight or less per 100 parts by weight of the silsesquioxane.
  • the curable resin composition preferably contains a heat-resistant resin.
  • a heat-resistant resin in the curable resin composition it is possible to obtain a cured film that is less likely to crack when subjected to high-temperature treatment, even in the case where the cured film has a large thickness.
  • the heat-resistant resins include polyimide, epoxy resin, silicone resin, benzoxazine resin, cyanate resin, phenolic resin, etc., and polyimide is particularly preferred from the viewpoint of heat resistance.
  • the molecular weight of the heat-resistant resin is not particularly limited, but is preferably 5,000 or more and 150,000 or less. By having the weight-average molecular weight of the heat-resistant resin in the above range, it is possible to obtain a cured film that is less likely to crack during high-temperature treatment, even if the cured film is thick.
  • the molecular weight of the heat-resistant resin is more preferably 10,000 or more, even more preferably 30,000 or more, more preferably 100,000 or less, and even more preferably 70,000 or less.
  • the content of the heat-resistant resin is preferably 0.5 parts by weight or more and 50 parts by weight or less based on 100 parts by weight of the silsesquioxane. By making the content of heat-resistant resin within the above range, even if it is made into a thick cured film, it can be made into a cured film that is less likely to crack when treated at high temperature.
  • the content of the heat-resistant resin is more preferably 0.7 parts by weight or more, more preferably 0.75 parts by weight or more, particularly preferably 1 part by weight or more, more preferably 20 parts by weight or less, more preferably 10 parts by weight or less, particularly preferably 5 parts by weight or less, based on 100 parts by weight of the silsesquioxane.
  • the polyimide preferably has a siloxane bond.
  • the compatibility with the silsesquioxane is increased, so that unevenness (surface roughness) caused by precipitation of the polyimide during application can be further suppressed.
  • the polyimide When the polyimide has a siloxane bond, the polyimide preferably has a ratio of carbon atoms to silicon atoms in the main chain structure, C/Si, of 17 or less.
  • C/Si a ratio of carbon atoms to silicon atoms in the main chain structure of the polyimide
  • the C/Si is more preferably 16.5 or less, and even more preferably 16 or less.
  • the lower limit of the C/Si is not particularly limited, but is preferably 4 or more from the viewpoint of practical use and further increasing the heat resistance at 400°C.
  • the ratio C/Si of carbon atoms to silicon atoms in the main chain structure of the polyimide is the ratio of C and Si in the repeating unit, and does not include C and Si at both ends.
  • the C/Si can be obtained by obtaining the structure of the polyimide by 1 H-NMR, 13 C-NMR, and 29 Si-NMR, and measuring the number of C atoms and Si atoms from the repeating unit of the main chain.
  • the polyimide preferably has an oxazine ring or imide ring structure at least at one of its terminals, and more preferably has an oxazine ring or imide ring structure at both terminals.
  • an oxazine ring or imide ring structure at the terminal of the polyimide surface roughness can be further suppressed when the polyimide is made into a thick film.
  • the oxazine ring and imide ring structures may have a substituent.
  • the polyimide has any one of the structures represented by the following structural formulas (2) to (7) at at least one terminal, and it is particularly preferable that both terminals have any one of the structures represented by the following structural formulas (2) to (7).
  • "*" in the structural formulas below represents a bonding site with a portion other than the terminal of the polyimide.
  • the polyimide preferably has a weight average molecular weight of 1,000 or more and 50,000 or less.
  • the weight average molecular weight of the polyimide is within the above range, the compatibility with the silsesquioxane is improved, and the handleability can be further improved.
  • the weight average molecular weight is more preferably 2000 or more, even more preferably 3000 or more, more preferably 35000 or less, and even more preferably 30000 or less.
  • the weight average molecular weight of the polyimide is measured as a polystyrene-equivalent molecular weight by gel permeation chromatography (GPC) using THF as an elution solvent and a Time-MB-M 6.0 ⁇ 150 mm (manufactured by Waters Corporation) or an equivalent column, and can be calculated with a polystyrene standard.
  • GPC gel permeation chromatography
  • the content of the polyimide is preferably 0.5 parts by weight or more and 50 parts by weight or less based on 100 parts by weight of the silsesquioxane.
  • the content of the polyimide is preferably 0.7 parts by weight or more, more preferably 0.75 parts by weight or more, and even more preferably 1 part by weight or more, and is preferably 20 parts by weight or less, more preferably 10 parts by weight or less, and even more preferably 5 parts by weight or less, based on 100 parts by weight of the silsesquioxane.
  • the curable resin composition of the present invention may contain other additives such as viscosity modifiers, fillers other than silica fillers, and adhesion promoters as necessary, within the scope of the invention.
  • the curable resin composition of the present invention has an elastic modulus at 300° C. of 0.2 MPa or more for a cured product after drying the solvent at 125° C. for 10 minutes and heat-curing by heat treatment at 300° C. for 1 hour.
  • the elastic modulus of the cured product at 300°C is preferably 0.2 MPa or more, more preferably 0.5 MPa or more, and even more preferably 1 MPa or more.
  • the upper limit of the elastic modulus of the cured product at 300°C is not particularly limited, but is preferably 100 MPa or less, more preferably 50 MPa or less, from the viewpoint of further suppressing warping and cracking of the substrate.
  • the elastic modulus can be adjusted by the type of the silsesquioxane, the type, shape and amount of the silica filler, the crosslinking structure, etc.
  • the elastic modulus can be specifically measured by the following method.
  • the curable resin composition is applied in a sheet form using an applicator or the like, dried at 125°C for 10 minutes, and then heated at 300°C for 1 hour to obtain a film of the cured product of the curable resin composition with a thickness of 500 ⁇ m.
  • the obtained film sample is punched out to a size of 5 mm x 35 mm to prepare a measurement sample.
  • the tensile modulus of the obtained measurement sample at 300°C is measured using a dynamic viscoelasticity measuring device (IT Measurement and Control Co., Ltd., DVA-200 or equivalent) under conditions of a constant temperature rise tensile mode, a temperature rise rate of 5°C/min, and a frequency of 1 Hz.
  • the curable resin composition of the present invention is preferably such that the coefficient of linear expansion (CTE) in the range of -40°C to 100°C is 500 ppm/°C or less for a cured product after drying the solvent under conditions of 125°C for 10 minutes and heat-curing by heat treatment at 300°C for 1 hour.
  • CTE coefficient of linear expansion
  • the linear expansion coefficient is more preferably 400 ppm/°C or less, and even more preferably 300 ppm/°C or less.
  • the lower limit of the linear expansion coefficient is not particularly limited, but is preferably 10 ppm/°C or more from the viewpoint of suppressing warping due to stress relaxation of the inorganic film.
  • the linear expansion coefficient can be adjusted by the type of the silsesquioxane, the type, shape and amount of the silica filler, crosslinking structure, etc.
  • the linear expansion coefficient can be measured by the following method.
  • the curable resin composition is applied in a sheet form using an applicator or the like, dried at 125°C for 10 minutes, and then heated at 300°C for 1 hour to obtain a film of the cured product of the curable resin composition with a thickness of 300 ⁇ m.
  • the obtained film sample is punched out to a size of 4 mm x 22 mm to prepare a measurement sample.
  • the obtained measurement sample is cooled to -70°C and then heated to 400°C at a heating rate of 5°C/min using a thermomechanical analyzer (Hitachi High-Tech Science Corporation, TMA7100 or equivalent), and the linear thermal expansion is measured, and the linear expansion coefficient in the range of -40°C to 100°C is calculated.
  • the method for producing the curable resin composition of the present invention is not particularly limited, and it can be produced, for example, by mixing the silsesquioxane, the solvent, the silica filler, and, if necessary, additives such as the catalyst and the heat-resistant resin with the solvent.
  • the curable resin composition of the present invention is preferably used as an insulating layer in a laminate consisting of multiple substrates in which the heat-cured cured product is used in semiconductor devices, image sensors, etc., and more preferably used by laminating an inorganic layer on the heat-cured cured product.
  • an insulating layer By forming such an insulating layer, it is possible to exhibit high moisture resistance while suppressing warping and cracking of the substrate, and further, wrinkles are less likely to occur in the inorganic layer, thereby suppressing process abnormalities caused by wrinkles in the inorganic layer.
  • Such a cured film obtained by thermally curing the curable resin composition of the present invention also constitutes the present invention.
  • a laminate using the cured film of the present invention that is, a laminate in which an organic layer made of the cured film of the present invention is laminated on a first substrate, and an inorganic layer is laminated on the organic layer, the first substrate has a first surface having a plurality of chips and a second surface which is the opposite surface, and the organic layer and the inorganic layer are on the first surface side (hereinafter also referred to as laminate A). is also one aspect of the present invention.
  • the laminate A of the present invention is a laminate in which an organic layer is laminated on a first element, and an inorganic layer is laminated on the organic layer.
  • the organic layer and inorganic layer serve as an insulating layer between each element and substrate in a semiconductor device in which a plurality of elements and substrates are laminated.
  • Conventional insulating layers use hard inorganic materials to withstand high-temperature treatment during manufacturing, so that when the substrate is deformed, the stress cannot be relieved and the substrate is prone to warping and cracking.
  • the substrate is less likely to warp or crack, and as a result, the electrode misalignment and cracking caused by the substrate warping and cracking can be suppressed, thereby improving the connection reliability between the substrates.
  • an inorganic layer as an auxiliary insulating layer on the organic layer, moisture in the atmosphere is less likely to permeate than the organic layer alone, so that high connection reliability can be achieved even under high temperature and high humidity.
  • the organic layer is made of a cured film of the curable resin composition of the present invention, wrinkles are less likely to occur in the inorganic layer even when the inorganic layer is laminated. As a result, process abnormalities such as alignment defects caused by wrinkles in the inorganic layer can be suppressed.
  • the inorganic layer of the laminate of the present invention is thin, the organic layer does not hinder the elimination of the warping of the substrate.
  • the first substrate is not particularly limited, and may be a circuit substrate on which elements and wiring are formed.
  • a sensor circuit substrate on which a pixel portion (pixel region) is provided a circuit substrate on which peripheral circuit portions such as logic circuits that perform various signal processing related to the operation of the solid-state imaging device are mounted, or a circuit substrate on which peripheral circuits such as memory circuits are mounted may be used.
  • the first substrate has a first surface having a plurality of chips and a second surface opposite thereto, and has the organic layer and the inorganic layer on the first surface side.
  • the chips form unevenness, so that the connection surface is not flat and the connection reliability is likely to decrease.
  • the organic layer fills the unevenness to make the connection surface flat, so that warping and cracking of the first substrate and the chips can be suppressed.
  • the inorganic layer covers the entire exposed surface of the organic layer.
  • Examples of the chips include memory circuit elements, logic circuit elements, etc.
  • the number of chips is not particularly limited as long as it is two or more.
  • the organic layer preferably has a thickness of 10 ⁇ m or more.
  • the thickness of the organic layer is preferably 20 ⁇ m or more, more preferably 30 ⁇ m or more, and preferably 200 ⁇ m or less, and more preferably 100 ⁇ m or less.
  • the material of the inorganic layer is not particularly limited, and examples thereof include SiN, SiO 2 , and Al 2 O 3. Among these, SiN and SiO 2 are preferred because of their excellent insulating properties and heat resistance.
  • the thickness of the inorganic layer is preferably 1 nm or more, more preferably 5 nm or more, and even more preferably 10 nm or more, from the viewpoint of further increasing the connection reliability of the laminate. Furthermore, from the viewpoint of not preventing the elimination of warpage in the substrate, the thickness is preferably 1 ⁇ m or less, more preferably 500 nm or less, and even more preferably 100 nm or less.
  • the laminate A of the present invention may further include a supporting substrate laminated on the inorganic layer.
  • a supporting substrate laminated on the inorganic layer.
  • the laminate A of the present invention may further have a second substrate on the second surface of the first substrate, and the first substrate and the second substrate may be electrically connected to each other.
  • the organic layer suppresses warping and cracking of the first substrate, warping and cracking of the second substrate further laminated on the first substrate are also suppressed, thereby improving connection reliability.
  • the second substrate may be the same as the first substrate.
  • the laminate A of the present invention has a structure in which an organic layer 3 and an inorganic layer 4 are laminated on the surface (first surface) of a first substrate 1 having a plurality of chips 2 on which the chips are laminated, and the organic layer 3 and the inorganic layer 4 act as insulating layers.
  • Conventional insulating layers consisting of an organic layer and an inorganic layer exhibit excellent connection reliability by suppressing warping and cracking of the substrate with the organic layer 3 and suppressing moisture permeation with the inorganic layer 4, but wrinkles in the inorganic layer, which cause process abnormalities, tend to occur.
  • the laminate of the present invention wrinkles are unlikely to occur in the inorganic layer by using the curable resin composition of the present invention as the material for the organic layer, so that process abnormalities such as alignment defects can be suppressed.
  • the laminate A of the present invention may have a support substrate 5 laminated on the inorganic layer 4, and a second substrate 6 may be laminated on the surface (second surface) opposite to the surface on which the organic layer 3 of the first substrate 1 is laminated, and the first substrate 1 and the second substrate 6 may be electrically connected.
  • the organic layer 3 and the inorganic layer 4 are single layers, but they may be made up of multiple layers.
  • a method for producing a laminate A of the present invention which includes a step of applying a curable resin composition of the present invention to a first surface of a first substrate having a first surface with a plurality of chips and a second surface opposite the first surface, and forming an organic layer by solvent drying and thermal curing, and a step of forming an inorganic layer on the organic layer, is also one aspect of the present invention.
  • the method for manufacturing the laminate A of the present invention first involves applying the curable resin composition of the present invention onto the first surface of a first substrate having a first surface having a plurality of chips and a second surface opposite the first surface, followed by solvent drying and thermal curing to form an organic layer.
  • Conventional laminates using inorganic materials for the insulating layer have been manufactured by time-consuming methods such as chemical vapor deposition (CVD) and sputtering. Since the main component of the insulating layer of the laminate of the present invention is an organic compound, it can be manufactured by applying a solution and drying it, which not only improves connection reliability but also increases production efficiency.
  • the first substrate and the curable resin composition are the same as the first substrate and the curable resin composition of the present invention in the laminate A of the present invention.
  • the method for forming the film is not particularly limited, and a conventionally known method such as spin coating can be used.
  • the solvent drying conditions are not particularly limited, but from the viewpoint of reducing the remaining solvent and improving the heat resistance of the organic layer, it is preferable to heat the organic layer at a temperature of preferably 70° C. or higher, more preferably 100° C. or higher, preferably 250° C. or lower, more preferably 200° C. or lower, for example, for 30 minutes, more preferably for about 1 hour.
  • the curing conditions are not particularly limited, but from the viewpoint of sufficiently progressing the curing reaction and further improving the heat resistance, it is preferable to heat for, for example, about 1 hour or more, more preferably 2 hours or more at a temperature of preferably 200° C.
  • the upper limit of the heating time is not particularly limited, but from the viewpoint of suppressing thermal decomposition of the organic layer, it is preferably 3 hours or less.
  • a step of forming an inorganic layer on the organic layer is then carried out.
  • Methods for forming the inorganic layer include chemical vapor deposition (CVD), sputtering, deposition, and the like.
  • the method for producing the laminate A of the present invention further includes a step of bonding the supporting substrate onto the inorganic layer.
  • the manufacturing method of the laminate A of the present invention includes a step of laminating a second substrate on the second surface of the first substrate and electrically connecting the first substrate and the second substrate.
  • the first and second substrates may be electrically connected by a method of melting and connecting the electrodes of the first and second substrates by heat treatment, etc.
  • the heat treatment is usually performed at 400° C. for about 4 hours.
  • An example of a laminate using the cured film of the present invention is a laminate having a structure in which two substrates having electrodes are electrically connected and an insulating layer made of the cured film of the present invention and an inorganic layer is disposed between the two substrates.
  • Such a laminate having an organic layer and an inorganic layer made of the cured film of the present invention between a third substrate having an electrode and a fourth substrate having an electrode, in which the electrode of the third substrate and the electrode of the fourth substrate are electrically connected via a through hole penetrating the organic layer and the inorganic layer (hereinafter, also referred to as laminate B), also constitutes one aspect of the present invention.
  • the laminate B of the present invention is a laminate having an organic layer and an inorganic layer composed of the cured film of the present invention between a third substrate having an electrode and a fourth substrate having an electrode, and the electrode of the third substrate and the electrode of the fourth substrate are electrically connected via a through hole penetrating the organic layer and the inorganic layer.
  • the cured film and inorganic layer provided between the electrode of the third substrate (hereinafter also referred to as the first electrode) and the electrode of the fourth substrate (hereinafter also referred to as the second electrode) act as an insulating layer, thereby suppressing short circuit of current.
  • the cured film made of a curable resin composition having higher flexibility than inorganic materials is used as the main insulating layer, so that the warping of the substrate can be eliminated, thereby exhibiting high connection reliability.
  • the moisture resistance can be increased by using a thin inorganic layer as an auxiliary insulating layer so as not to prevent the elimination of the warping of the substrate.
  • the cured film of the present invention is less likely to cause wrinkles in the inorganic layer even when an inorganic layer is laminated on the cured film, so that process defects such as alignment defects can be suppressed.
  • being electrically connected refers to a state in which the first electrode and the second electrode are connected by a conductive material or the like filled in the through hole.
  • the third and fourth substrates may be the same as the first substrate.
  • the organic and inorganic layers may be the same as the organic and inorganic layers of the laminate A of the present invention.
  • the inorganic layer may be formed on both the organic layers of the third and fourth substrates, or may be formed on only one of the organic layers.
  • the inorganic layer is preferably formed on the organic layers of both the third and fourth substrates, and more preferably covers the entire side surface of the organic layer, since this improves the connection reliability under high temperature and high humidity.
  • the materials of the electrodes of the third and fourth substrates and the conductive material are not particularly limited, and conventional electrode materials such as gold, copper, and aluminum can be used.
  • the laminate B of the present invention preferably has a barrier metal layer on the surface of the through hole.
  • the barrier metal layer has a role of preventing the diffusion of the conductive material (e.g., Cu atoms in the case of a Cu electrode) filled in the through hole into the organic layer.
  • the conductive material e.g., Cu atoms in the case of a Cu electrode
  • the material of the barrier metal layer can be a known material such as tantalum, tantalum nitride, titanium nitride, silicon oxide, silicon nitride, etc.
  • the thickness of the barrier metal layer is not particularly limited, but from the viewpoint of further improving the connection reliability of the laminate, it is preferably 1 nm or more, more preferably 10 nm or more, more preferably 100 nm or less, and even more preferably 50 nm or less.
  • the laminate B of the present invention has a structure in which a third substrate 7 having an electrode 8 and a fourth substrate 9 are bonded via an organic layer 3 and an inorganic layer 4, and the electrodes 8 on the third substrate 7 and the fourth substrate 9 are electrically connected through a conductive material filled in a through hole 10 provided in the organic layer 3.
  • the organic layer 3 corresponding to the insulating layer was a hard inorganic material, so that when warping occurred in the substrate or laminate, this could not be eliminated by stress relaxation, and the electrodes were prone to misalignment and cracking.
  • the laminate B of the present invention can eliminate warping of the substrate or laminate by using an organic layer made of the cured film of the present invention having flexibility in the insulating layer, so that the electrodes can be prevented from misaligning and cracking.
  • the moisture resistance can be improved by using a thin inorganic layer 4 as an auxiliary insulating layer so as not to prevent the elimination of the warp of the substrate. If the inorganic layer 4 covers the entire side surface of the organic layer 3, the moisture resistance can be further improved.
  • the cured film of the present invention is unlikely to cause wrinkles in the inorganic layer even when an inorganic layer is laminated on the cured film, so that process defects such as alignment defects can be suppressed.
  • the laminate B of the present invention may be provided with a barrier metal layer 11 on the surface of the through hole 10.
  • the barrier metal layer 11 By providing the barrier metal layer 11, the conductive material filled in the through hole 10 is unlikely to diffuse into the organic layer 3, so that short circuits and conduction defects can be further suppressed.
  • the inorganic layer 4 is provided on the organic layer 3 on the third substrate 7 side and the fourth substrate 9 side, but it may be provided on only one of them.
  • the present invention also provides a method for producing a laminate B, which includes the steps of applying the curable resin composition of the present invention onto the surfaces of a third substrate having an electrode and a fourth substrate having an electrode, drying the solvent, and thermally curing the composition to form an organic layer, forming an inorganic layer on the organic layer, forming through-holes in each of the organic layers and the inorganic layer, filling each of the through-holes with a conductive material, polishing the surfaces of the third substrate having an electrode and the fourth substrate having an electrode on the side filled with the conductive material to form a bonding electrode, and bonding the third substrate having an electrode and the fourth substrate having an electrode so that the bonding electrodes of the third substrate having an electrode and the fourth substrate having an electrode are bonded to each other.
  • a step of forming through holes in each of the organic layers and the inorganic layers is then carried out.
  • the through-hole may be patterned.
  • the method for forming the through-hole is not particularly limited, and the through-hole may be formed by laser irradiation such as CO2 laser or etching.
  • the through-hole is formed so as to penetrate the other layers and expose the electrode surface of the substrate.
  • a step of forming a barrier metal layer is then carried out as necessary.
  • the barrier metal layer may be the same as that of the laminate B of the present invention.
  • the barrier metal layer may be formed by sputtering, vapor deposition or the like.
  • the method for producing the laminate B of the present invention then includes a step of filling each of the through holes with a conductive material.
  • a method for filling the through holes with the conductive material plating or the like can be used.
  • the conductive material may be the same as the conductive material of the laminate B of the present invention.
  • the method for producing the laminate B of the present invention then includes a step of polishing the surfaces of the third substrate having the electrode and the fourth substrate having the electrode, the surfaces being filled with the conductive material, to form bonding electrodes.
  • the conductive material formed in the unnecessary portion is removed by grinding to form a bonding electrode connecting the electrodes formed on the two elements.
  • the polishing is preferably performed by planarizing and removing the layer formed of the conductive material until the inorganic layer is exposed.
  • the polishing method is not particularly limited, and for example, a chemical mechanical polishing method can be used.
  • the method for producing laminate B of the present invention then carries out a step of bonding the third substrate having the electrode and the fourth substrate having the electrode together so that the bonding electrodes of the third substrate having the electrode are bonded to each other.
  • the third substrate and the fourth substrate may be bonded to each other by a method of melting and connecting the electrodes and the connecting electrodes by heat treatment, etc.
  • the heat treatment is usually performed at 400° C. for about 4 hours.
  • the uses of the laminates A and B of the present invention are not particularly limited, but they are suitable for imaging devices and semiconductor devices because even when an inorganic layer is formed on an organic layer, wrinkles are unlikely to occur in the inorganic layer and process abnormalities can be suppressed.
  • imaging devices having the laminates of the present invention and semiconductor devices having the laminates of the present invention are also part of the present invention.
  • the present invention provides a curable resin composition that is less likely to cause wrinkles in the inorganic layer even when an inorganic layer is formed on the cured product, and that can suppress process abnormalities, a cured film of the curable resin composition, a laminate using the cured film, an imaging device and a semiconductor device having the laminate, and a method for manufacturing the laminate.
  • FIG. 1 is a schematic diagram showing an example of a laminate A of the present invention.
  • FIG. 2 is a schematic diagram showing an example of a laminate B of the present invention.
  • the reaction mixture thus obtained was separated, and the organic layer was washed once with 1N hydrochloric acid, once with a saturated aqueous solution of sodium bicarbonate, and then washed three times with ion-exchanged water.
  • the washed organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure using a rotary evaporator to obtain 7.1 g of a white powdery solid (DD(Me)-OH).
  • a 100 mL flask was fitted with a cooling tube, mechanical stirrer, Dean-Stark tube, oil bath and thermometer protection tube, and the inside of the flask was replaced with nitrogen.
  • 5.0 g of DD(Me)-OH, 11.6 g of octamethylcyclotetrasiloxane (D4), 3.9 g of sulfuric acid, 52 g of toluene and 13 g of 4-methyltetrahydropyran were placed in the flask. After stirring at 100°C for 5 hours, water was poured into the reaction mixture and the aqueous layer was extracted with toluene.
  • the combined organic layer was washed with water, an aqueous sodium bicarbonate solution, and saturated saline, and then dried with anhydrous sodium sulfate.
  • the flask was heated at 100°C for 1 hour, and then refluxed in an oil bath at 170°C for 1 hour.
  • the solution was cooled to room temperature, 1.3 g of citraconic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 120°C for 10 minutes, and then refluxed in an oil bath at 170°C for 1 hour to obtain a heat-resistant resin (resin D, weight average molecular weight: 9900) having the structure of the following structural formula (9).
  • l in the following structural formula (9) represents the number of repeating units.
  • Example 1 Production of a curable resin composition
  • a curable resin composition was obtained by adding and mixing 100 parts by weight of the obtained silsesquioxane, 1 part by weight of the obtained heat-resistant resin, 0.1 parts by weight of the catalyst, and 30 parts by weight of the silica filler to a solvent content of 65% by weight.
  • the details of each raw material used are as follows.
  • Silica filler MT-10, manufactured by Tokuyama Corporation, bulk density: 0.05 g/cm 3 , shape: pulverized
  • Solvent N-methyl-2-pyrrolidone (referred to as NMP in the table)
  • the curable resin composition applied in a sheet form using an applicator was dried under conditions of 125°C for 10 minutes, and then heated at 300°C for 1 hour to obtain a film of the cured product of the curable resin composition having a thickness of 500 ⁇ m.
  • the obtained film sample was punched out to a size of 5 mm x 35 mm to prepare a measurement sample.
  • the obtained measurement sample was measured for elastic modulus at 300°C using a dynamic viscoelasticity measuring device (manufactured by IT Measurement and Control Co., Ltd., DVA-200) under conditions of a constant temperature rise tensile mode, a temperature rise rate of 5°C/min, and a frequency of 1 Hz.
  • Examples 2 to 16, Comparative Examples 1 to 5 A laminate was obtained and each measurement was carried out under the same conditions as in Example 1, except that the compositions and thicknesses of the organic and inorganic layers were as shown in Tables 1 and 2. The details of the raw materials in the tables are as follows.
  • the surface of the inorganic layer of the obtained laminate was observed with a laser microscope to measure the surface roughness of the laminate (inorganic layer). Specifically, a laser microscope (OLS4100, manufactured by Olympus Corporation) was used to observe the surface at 20 times magnification in an observation range of 643 ⁇ m square, and the surface roughness Sa value was calculated.
  • OLS4100 manufactured by Olympus Corporation
  • the present invention provides a curable resin composition that is less likely to cause wrinkles in the inorganic layer even when an inorganic layer is formed on the cured product, and that can suppress process abnormalities, a cured film of the curable resin composition, a laminate using the cured film, an imaging device and a semiconductor device having the laminate, and a method for manufacturing the laminate.

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PCT/JP2024/023874 2023-07-03 2024-07-02 硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置及び積層体の製造方法 Ceased WO2025009514A1 (ja)

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JP2013504684A (ja) * 2009-09-14 2013-02-07 ナミックス株式会社 高密度相互接続フリップチップのためのアンダーフィル
WO2013073606A1 (ja) * 2011-11-15 2013-05-23 株式会社日本触媒 シラン含有組成物、硬化性樹脂組成物及び封止材
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