WO2023120627A1 - 硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置、積層体の製造方法及び接合電極を有する素子の製造方法 - 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、積層体の製造方法及び接合電極を有する素子の製造方法 Download PDF

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WO2023120627A1
WO2023120627A1 PCT/JP2022/047305 JP2022047305W WO2023120627A1 WO 2023120627 A1 WO2023120627 A1 WO 2023120627A1 JP 2022047305 W JP2022047305 W JP 2022047305W WO 2023120627 A1 WO2023120627 A1 WO 2023120627A1
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Prior art keywords
laminate
cured film
curable resin
resin composition
electrode
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PCT/JP2022/047305
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English (en)
French (fr)
Japanese (ja)
Inventor
颯 野元
太郎 塩島
徳重 七里
憲一朗 佐藤
英寛 出口
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Priority to CN202280069200.5A priority Critical patent/CN118139931A/zh
Priority to US18/720,896 priority patent/US20250051573A1/en
Priority to EP22911329.5A priority patent/EP4455224A4/en
Priority to JP2023503049A priority patent/JP7425257B2/ja
Priority to KR1020247007674A priority patent/KR20240121703A/ko
Publication of WO2023120627A1 publication Critical patent/WO2023120627A1/ja
Priority to JP2024005955A priority patent/JP2024052692A/ja
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    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2479/00—Characterised by the use of 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 C08J2461/00 - C08J2477/00
    • C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
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    • H10W20/40—Interconnections external to wafers or substrates, e.g. back-end-of-line [BEOL] metallisations or vias connecting to gate electrodes
    • H10W20/45—Interconnections external to wafers or substrates, e.g. back-end-of-line [BEOL] metallisations or vias connecting to gate electrodes characterised by their insulating parts
    • H10W20/48—Insulating materials thereof
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    • H10W72/012—Manufacture or treatment of bump connectors, dummy bumps or thermal bumps
    • H10W72/01231—Manufacture or treatment of bump connectors, dummy bumps or thermal bumps using blanket deposition
    • H10W72/01233—Manufacture or treatment of bump connectors, dummy bumps or thermal bumps using blanket deposition in liquid form, e.g. spin coating, spray coating or immersion coating
    • H10W72/01235—Manufacture or treatment of bump connectors, dummy bumps or thermal bumps using blanket deposition in liquid form, e.g. spin coating, spray coating or immersion coating by plating, e.g. electroless plating or electroplating
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    • H10W72/013—Manufacture or treatment of die-attach connectors
    • H10W72/01331—Manufacture or treatment of die-attach connectors using blanket deposition
    • H10W72/01333—Manufacture or treatment of die-attach connectors using blanket deposition in liquid form, e.g. spin coating, spray coating or immersion coating
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    • H10W72/01361—Chemical or physical modification, e.g. by sintering or anodisation
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    • H10W72/244—Dispositions, e.g. layouts relative to underlying supporting features, e.g. bond pads, RDLs or vias
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    • H10W72/351—Materials of die-attach connectors
    • H10W72/353—Materials of die-attach connectors not comprising solid metals or solid metalloids, e.g. ceramics
    • H10W72/354—Materials of die-attach connectors not comprising solid metals or solid metalloids, e.g. ceramics comprising polymers
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    • H10W90/721—Package configurations characterised by the relative positions of pads or connectors relative to package parts of bump connectors
    • H10W90/722—Package configurations characterised by the relative positions of pads or connectors relative to package parts of bump connectors between stacked chips
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    • H10W90/701—Package configurations characterised by the relative positions of pads or connectors relative to package parts
    • H10W90/731—Package configurations characterised by the relative positions of pads or connectors relative to package parts of die-attach connectors
    • H10W90/732—Package configurations characterised by the relative positions of pads or connectors relative to package parts of die-attach connectors between stacked chips

Definitions

  • the present invention provides a curable resin composition, a cured film using the curable resin composition, a laminate having the cured film, an imaging device and a semiconductor device having the laminate, a method for producing the laminate, and the laminate
  • the present invention relates to a method of manufacturing an element having bonding electrodes for use in manufacturing a body.
  • the insulating layer used to form the joint surface is required to have high heat resistance.
  • an insulating inorganic material such as Si 3 N 4 or SiO 2 is used as an insulating layer.
  • an insulating layer made of an inorganic material is likely to warp in an element. Connection reliability may be low.
  • the performance of semiconductor devices has been improved, and elements have become larger and thinner, so that the elements are more likely to warp.
  • An insulating layer made of an organic compound may be used to suppress the warp of the element, but the insulating layer made of the organic compound has a problem that it is vulnerable to heat. On the other hand, it is possible to use a heat-resistant organic compound. , 400° C. for 4 hours, resulting in film cracking.
  • the present invention includes a curable resin composition that does not easily cause film cracking at high temperatures in a nitrogen atmosphere even when a thick film is formed, a cured film using the curable resin composition, and the cured film.
  • An object of the present invention is to provide a laminate, an imaging device and a semiconductor device having the laminate, a method for manufacturing the laminate, and a method for manufacturing an element having a junction electrode used for manufacturing the laminate.
  • the present invention includes the following disclosures. The present invention will be described in detail below.
  • [Disclosure 1] A curable resin composition comprising a polyimide and a silsesquioxane, wherein the content of the polyimide is 0.5 parts by weight or more and 50 parts by weight or less with respect to 100 parts by weight of the silsesquioxane.
  • [Disclosure 2] The curable resin composition according to Disclosure 1, wherein the polyimide has a siloxane bond.
  • R 0 , R 1 and R 2 each independently represent a linear, branched or cyclic aliphatic group, 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.
  • a method for manufacturing a laminate comprising a step of bonding the first element having the bonding electrode formed thereon and the second element having the bonding electrode formed thereon so that the bonding electrodes are bonded to each other.
  • [Disclosure 15] A step of forming a film of the curable resin composition according to any one of Disclosures 1 to 7 on the electrode-formed surface of an element having an electrode, and curing the solvent after drying to form a cured film; forming through holes in the cured film; filling the through holes with a conductive material; and polishing the surface of the element to form a bonding electrode.
  • [Disclosure 16] A laminate having the cured film according to Disclosure 8 or 9 between a support substrate and a third element, The third element has a first surface and a second surface, and the first surface has a plurality of stacked chips electrically connected to the third element, A laminate having the cured film between the first surface and the support substrate.
  • the curable resin composition of the present invention contains polyimide.
  • polyimide By using polyimide in the curable resin composition, it is possible to obtain a cured film that is less likely to crack during high-temperature treatment even when the cured film is thick.
  • the polyimide preferably has a siloxane bond. Since the polyimide has a siloxane bond, the compatibility with silsesquioxane contained in the curable resin composition is enhanced, so that unevenness (surface roughness) due to deposition of polyimide during coating can be suppressed. .
  • the polyimide When the polyimide has a siloxane bond, the polyimide preferably has a ratio C/Si of carbon atoms to silicon atoms in the main chain structure of 17 or less.
  • the ratio of carbon atoms and silicon atoms in the main chain structure of the polyimide is within the above range, the compatibility with silsesquioxane contained in the curable resin composition is further increased, so surface roughness during application is improved. can be suppressed further.
  • the above C/Si is more preferably 16.5 or less, even more preferably 16 or less.
  • the lower limit of C/Si is not particularly limited, it is preferably 4 or more for practical use and from the viewpoint of further improving the 400° C. heat resistance.
  • 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 terminals.
  • the above C/Si can be obtained by obtaining the structure of the above polyimide by 1 H-NMR, 13 C-NMR and 29 Si-NMR and measuring the number of C atoms and Si atoms from the main chain repeating unit. can be done.
  • the above polyimide does not have a siloxane bond, or the ratio C / Si of carbon atoms and silicon atoms in the main chain structure is 20 or more. It is also preferable to have The above polyimide does not have a siloxane bond or the ratio of carbon atoms and silicon atoms in the main chain structure of the polyimide is within the above range, so due to restrictions on equipment and manufacturing methods, etc., an oxygen atmosphere that is more severe than a nitrogen atmosphere Even in the case where a laminate must be produced at high temperatures, it is possible to obtain a cured film that is less likely to crack due to high-temperature treatment.
  • the above C/Si is more preferably 21 or more. In the normal production of the laminate, since the element is joined in a nitrogen atmosphere, sufficient connection reliability can be exhibited if the insulating layer does not crack at a high temperature in the nitrogen atmosphere.
  • the polyimide preferably has a plurality of aromatic rings.
  • the polyimide has a plurality of aromatic rings, even when a thick cured film is formed, it is possible to obtain a cured film that is less likely to crack during high-temperature treatment under various conditions.
  • the polyimide preferably has an oxazine ring or imide ring structure at least one of its terminals, and more preferably has an oxazine ring or imide ring structure at both terminals. Having an oxazine ring or imide ring structure at the end of the polyimide makes it possible to further suppress surface roughness when a thick film is formed.
  • the oxazine ring and imide ring structures may have substituents. Among them, it is more preferable that at least one end of the polyimide has a structure of one of the following formulas (1) to (6), and both ends have one of the following formulas (1) to (6). Having a structure is particularly preferred.
  • "*" in the following formula represents a bonding site with a portion other than the end of the polyimide.
  • the polyimide preferably has a weight average molecular weight of 1,000 or more and 20,000 or less.
  • the weight average molecular weight is more preferably 2,000 or more, still more preferably 3,000 or more, more preferably 18,000 or less, and even more preferably 15,000 or less.
  • the weight average molecular weight of the polyimide is measured as a polystyrene equivalent molecular weight by a gel permeation chromatography (GPC) method. Using THF as an elution solvent, using a column of Time-MB-M 6.0 ⁇ 150 mm (manufactured by Waters) or its equivalent, the calculation can be performed according to a polystyrene standard.
  • the content of the polyimide is 0.5 parts by weight or more and 50 parts by weight or less with respect to 100 parts by weight of silsesquioxane described later. By setting the content of the polyimide within the above range, it is possible to obtain a cured film that is less likely to crack during high-temperature treatment even when the cured film is thick.
  • the content of the polyimide is preferably 0.7 parts by weight or more, more preferably 0.75 parts by weight or more, and preferably 1 part by weight or more with respect to 100 parts by weight of silsesquioxane. More preferably, it is 20 parts by weight or less, more preferably 10 parts by weight or less, and even more preferably 5 parts by weight or less.
  • the curable resin composition of the present invention contains silsesquioxane.
  • a cured film of an organic curable resin composition as the insulating layer, the flexibility can be increased, the warpage of the element can be suppressed, and the electrical connection reliability can be improved.
  • silsesquioxane in the curable resin composition an insulating layer having excellent heat resistance can be obtained.
  • the silsesquioxane preferably has a structure represented by the following formula (7).
  • the silsesquioxane has the structure of formula (7), the heat resistance can be further improved, and the displacement and cracking of the electrodes can be further suppressed to improve electrical connection reliability.
  • R 0 , R 1 and R 2 each independently represent a linear, branched or cyclic aliphatic group, 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.
  • Each R 0 in the formula (1) independently represents a linear, branched or cyclic aliphatic group, 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 in the above formula (1) each independently represent a linear, branched or cyclic aliphatic group, 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, more preferably a phenyl group or a methyl group.
  • R 1 and R 2 are 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 integers 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, more preferably 6 or less.
  • the silsesquioxane preferably has a reactive site.
  • silsesquioxane having a reactive site As the curable resin of the curable resin composition, cracking of the cured film of the curable resin composition is further suppressed even when heat treatment is performed at 400 ° C. can do.
  • the reactive sites include hydroxyl groups and alkoxy groups.
  • the silsesquioxane having the reactive site include silsesquioxane represented by the above formula (7). Although not shown in the structural formula, the silsesquioxane represented by the above formula (7) has reactive functional groups derived from raw materials at both ends.
  • the content of the silsesquioxane is preferably 85 parts by weight or more, more preferably 90 parts by weight or more, and 95 parts by weight or more in 100 parts by weight of the solid content in the curable resin composition. is more preferable.
  • the content of the silsesquioxane is preferably 99 parts by weight or less, more preferably 98 parts by weight or less, based on 100 parts by weight of the solid content in the curable resin composition.
  • the weight average molecular weight of the silsesquioxane is not particularly limited, it is preferably 5,000 or more and 150,000 or less. When the molecular weight of the silsesquioxane is within the above range, the film-forming property during coating is improved, the flattening performance is further improved, and displacement and cracking of the electrode can be further suppressed.
  • the molecular weight of the silsesquioxane is more preferably 10,000 or more, still more preferably 30,000 or more, more preferably 100,000 or less, and even more preferably 70,000 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, using a column of Time-MB-M 6.0 ⁇ 150 mm (manufactured by Waters) or its equivalent, the calculation can be performed according to a polystyrene standard.
  • the silsesquioxane having the structure of the above formula (7) can be obtained, for example, by reacting a compound (8) represented by the following formula (8) with a compound (9) represented by the following formula (9). can be obtained by
  • R 0 and R 1 represent the same functional groups as R 0 and R 1 in the above formula (7).
  • R 2 represents the same functional group as R 2 in formula (7) above.
  • h represents a natural number, preferably 3-6, more preferably 3 or 4.
  • the compound having the structure of the above formula (7) is obtained by reacting the compound (8) with a halogenated siloxane having R 2 (for example, terminally chlorinated dimethylsiloxane, etc.) instead of the compound (9). It can also be obtained by letting
  • the compound (8) can be obtained, for example, by reacting a salt such as the compound (10) represented by the following formula (10) with the compound (11) represented by the following formula (11). .
  • the compound (8) can also be obtained by reacting the compound (11) in which X is hydrogen with the compound (10), followed by hydrolysis.
  • R 0 represents the same functional group as R 0 in formula (7) above.
  • R 1 means the same functional group as R 1 in formula (7) above, and X means hydrogen, chlorine or hydroxyl.
  • the compound (10) is obtained by, for example, hydrolyzing a compound (12) represented by the following formula (12) in the presence or absence of an organic solvent in the presence of a monovalent alkali metal hydroxide and water, It can be produced by polycondensation.
  • a compound (12) represented by the following formula (12) in the presence or absence of an organic solvent in the presence of a monovalent alkali metal hydroxide and water, It can be produced by polycondensation.
  • Lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide and the like can be used as the monovalent alkali metal hydroxide.
  • R 0 means the same functional group as R 0 in formula (7) above.
  • the curable resin composition of the present invention preferably contains a catalyst that accelerates the curing reaction.
  • the curable resin composition has a catalyst, the curable resin composition can be cured more completely, and decomposition of the cured film due to high-temperature treatment can be further suppressed.
  • the catalyst include organic tin compounds such as dibutyltin dilaurate and stannous acetate, metal carboxylates such as zinc naphthenate, zirconia compounds such as zirconium tetraacetylacetonate, and titanium compounds. Among them, zirconium tetraacetylacetonate is preferable because thermal decomposition of a cured film obtained by curing the curable resin composition is further suppressed.
  • the catalyst is present even after the curable resin composition is cured. That is, the cured film formed by curing the curable resin composition of the present invention preferably contains a catalyst that accelerates the curing reaction.
  • the content of the catalyst is not particularly limited, it is preferably 0.01 parts by weight or more and 10 parts by weight or less with respect to 100 parts by weight of silsesquioxane in the curable resin composition.
  • the content of the catalyst is more preferably 0.1 parts by weight or more, still more preferably 0.2 parts by weight or more, more preferably 7 parts by weight or less, and 5 parts by weight or less. is more preferred.
  • the curable resin composition preferably contains a polyfunctional cross-linking agent capable of reacting with the reactive site of the silsesquioxane having the reactive site.
  • a polyfunctional cross-linking agent capable of reacting with the reactive sites of silsesquioxane By cross-linking between the silsesquioxane polymers having the above reactive sites with a polyfunctional cross-linking agent capable of reacting with the reactive sites of silsesquioxane, the cross-linking density of the cured product increases, and decomposition at high temperatures is more suppressed. As a result, it is possible to further suppress the generation of voids due to the generation of decomposition gas during high-temperature processing, the displacement of the electrodes during connection, and the deterioration of electrical connection reliability due to such voids.
  • polyfunctional cross-linking agent examples include, when the reactive sites are silanol groups, alkoxysilane compounds such as dimethoxysilane compounds, trimethoxysilane compounds, diethoxysilane compounds, and triethoxysilane compounds, or tetramethoxysilane.
  • alkoxysilane compounds such as dimethoxysilane compounds, trimethoxysilane compounds, diethoxysilane compounds, and triethoxysilane compounds, or tetramethoxysilane.
  • silicate oligomer obtained by condensation of a compound and a tetraethoxysilane compound, and the like. Of these, silicate oligomers are preferred from the viewpoint of improving crosslink density and improving heat resistance.
  • alkoxysilane compounds include dimethoxydimethylsilane, trimethoxymethylsilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, etc.
  • silicate oligomers include silicates MS51, MS56, MS57 and MS56S (all Mitsubishi Chemical Co., Ltd.), Ethyl Silicate 40, Ethyl Silicate 48, EMS485 (all of Colcoat Co., Ltd.), and the like.
  • the content of the polyfunctional cross-linking agent is not particularly limited, it is preferably 1 part by weight or more and 50 parts by weight or less with respect to 100 parts by weight of the curable resin in the curable resin composition.
  • the content of the polyfunctional cross-linking agent is more preferably 3 parts by weight or more, still more preferably 3.2 parts by weight or more, more preferably 30 parts by weight or less, and 20 parts by weight or less. It is even more preferable to have
  • the above curable resin composition may contain other additives such as a viscosity modifier, a filler, an adhesion imparting agent and a solvent, if necessary.
  • the use of the curable resin composition of the present invention is not particularly limited, but even when it is formed into a thick cured film, it is difficult to cause film cracking due to high temperature in a nitrogen atmosphere, so it is used as an electrode for two elements having electrodes. It can be suitably used as an insulating layer when electrically connecting between them to produce a laminate.
  • a cured film formed using such a curable resin composition of the present invention is also one aspect of the present invention.
  • a laminate having the cured film of the present invention between a first element having an electrode and a second element having an electrode the electrode of the first element and the electrode of the second element is electrically connected via a through-hole penetrating the cured film (hereinafter also simply referred to as a laminate or laminate A).
  • the laminate of the present invention will be described below.
  • the laminated body of the present invention has the cured film of the present invention between a first element having an electrode and a second element having an electrode, and the electrode of the first element and the second element and electrodes are electrically connected through through-holes passing through the cured film.
  • the cured film provided between the electrode of the first element (hereinafter also referred to as the first electrode) and the electrode of the second element (hereinafter also referred to as the second electrode) acts as an insulating layer, Short circuit of current can be suppressed.
  • Conventional insulating layers use hard inorganic materials such as Si 3 N 4 and SiO 2 . Therefore, if warping occurs during the formation of the insulating layer or the formation of the laminate, this cannot be resolved by stress relaxation.
  • the warp of the element and the displacement and cracking of the electrodes caused by this tend to occur.
  • a cured film having higher flexibility than an inorganic material as an insulating layer, high electrical connection reliability can be exhibited.
  • the effect film of the present invention is less likely to crack even when it is thick, so that a laminate having higher electrical connection reliability can be obtained.
  • the conventional insulating layer is formed by vapor deposition, which takes a long time to form. Efficiency can be increased.
  • “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 first element and the second element are not particularly limited, and circuit elements in which elements, wirings and electrodes are formed can be used.
  • a sensor circuit element provided with a pixel section (pixel region), or a circuit element provided with a peripheral circuit section such as a logic circuit for executing various signal processing related to the operation of the solid-state imaging device.
  • the material of the electrodes of the first element and the second element and the conductive material are not particularly limited, and conventionally known electrode materials such as gold, copper, and aluminum can be used.
  • the thickness of the cured film is not particularly limited, it is preferably 10 ⁇ m or more and 300 ⁇ m or less. When the thickness of the cured film is within the above range, the function as an insulating layer can be exhibited more effectively, and displacement and cracking of the electrode can be further suppressed.
  • the thickness of the cured film is more preferably 20 ⁇ m or more, still more preferably 30 ⁇ m or more, more preferably 200 ⁇ m or less, and even more preferably 100 ⁇ m or less.
  • the laminate of the present invention preferably has an inorganic layer between the first element and the second element.
  • an inorganic layer between the first element and the second element By providing an inorganic layer between the first element and the second element, it is possible to obtain a laminate having improved insulation and excellent connection reliability.
  • the conventional laminate uses an insulating layer made of an inorganic material having a thickness of about 10 to 20 ⁇ m, the warpage of the element and the laminate cannot be eliminated, which causes a decrease in connection reliability.
  • the insulating layer is the cured film, if the thickness of the inorganic layer is reduced, the effect of the inorganic layer can be exhibited and the warpage occurring in the element and the laminated body can be eliminated.
  • the material of the inorganic layer is not particularly limited, and examples thereof include Si 3 N 4 , SiO 2 , Al 2 O 3 and the like. Among them, Si 3 N 4 and SiO 2 are preferable 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, still more preferably 10 nm or more, and 1 ⁇ m or less from the viewpoint of further improving the connection reliability of the laminate. It is preferably 500 nm or less, more preferably 100 nm or less.
  • the laminate of the present invention preferably has a barrier metal layer on the surfaces of the through holes.
  • the barrier metal layer has a role of preventing diffusion of the conductive material (for example, Cu atoms in the case of a Cu electrode) filled in the through hole into the cured film.
  • the conductive material for example, Cu atoms in the case of a Cu electrode
  • the barrier metal layer By providing the barrier metal layer on the surface of the through hole, the conductive material filling the through hole is covered with the barrier metal layer except for the surface in contact with the electrode. Conduction failure can be further suppressed.
  • materials for the barrier metal layer known materials such as tantalum, tantalum nitride, titanium nitride, silicon oxide, and silicon nitride can be used.
  • the thickness of the barrier metal layer is not particularly limited, it is more preferably 1 nm or more, still more preferably 10 nm or more, and more preferably 100 nm or less from the viewpoint of increasing the connection reliability of the laminate. It is more preferably 50 nm or less.
  • FIG. 1 shows a diagram schematically showing one aspect of the laminate of the present invention.
  • a first element 1 having an electrode 3 and a second element 2 are bonded via a cured film 4, and the first element 1 and the second element 2 are bonded together.
  • the electrodes 3 on the element 2 are electrically connected through the conductive material filled in the through holes 5 provided in the cured film 4 .
  • the portion of the cured film 4 corresponding to the insulating layer is made of a hard inorganic material, so when the element or laminate is warped, it cannot be eliminated by stress relaxation, and the electrodes are likely to shift or crack.
  • the present invention by using a flexible organic compound for the insulating layer, warping of the element and the laminate can be eliminated, and displacement and cracking of the electrodes can be suppressed.
  • FIG. 2 shows a diagram schematically showing one aspect of the laminate of the present invention.
  • the inorganic layer 6 is provided between the cured films 4 to further enhance the insulation. Since the thickness of the inorganic layer 6 of the present invention may be significantly thinner than the insulating layer of the conventional laminate, it does not hinder the elimination of warpage of the element or laminate.
  • the inorganic layer 6 is provided between the cured films 4 in FIG. 2, it may be provided on the first element 1 and the second element 2 .
  • the inorganic layer 6 is provided on each of the cured films 4 on the first element 1 side and the second element 2 side in FIG. 2, it may be provided on only one of them. Furthermore, in the embodiment of FIG.
  • a barrier metal layer 7 is provided on the surface of the through hole 5 . Forming the barrier metal layer 7 on the surface of the through-hole 5 makes it difficult for the conductive material filled in the through-hole 5 to diffuse into the cured film 4, thereby further suppressing short circuits and defective conduction.
  • the curable resin composition of the present invention is formed on the surface on which the electrodes of the first element having the electrode and the second element having the electrode are formed, forming a cured film by curing after solvent drying; forming through holes in each of the cured films; filling each of the through holes with a conductive material; a step of polishing the surface of the element filled with the conductive material to form a junction electrode; and a step of bonding the bonding electrodes so that they are bonded to each other.
  • a method for producing such a laminate is also one aspect of the present invention.
  • the curable resin composition of the present invention is formed on the surface of the first element having the electrode on which the electrode is formed, and the solvent is dried and then cured to form a cured film.
  • the first and second elements having the electrodes and the curable resin composition are the same as the first and second elements having electrodes of the laminate of the present invention and the curable resin composition of the present invention. can be used.
  • the cured film of the present invention is less likely to crack even when it is thick, so that the reliability of electrical connection can be improved.
  • the film formation method is not particularly limited, and conventionally known methods such as spin coating can be used.
  • Solvent drying conditions are not particularly limited, but from the viewpoint of reducing the residual solvent and improving the heat resistance of the cured film, it is preferably 70 ° C. or higher, more preferably 100 ° C. or higher, preferably 250 ° C. or lower, more preferably 200 ° C. or lower. It is preferable to heat at the temperature for, for example, 10 minutes, preferably 15 minutes, more preferably 30 minutes, and still more preferably about 1 hour.
  • the curing conditions are not particularly limited, but from the viewpoint of sufficiently advancing the curing reaction and further improving heat resistance, it is preferably 200° C. or higher, more preferably 220° C. or higher, preferably 400° C.
  • the heating time is not particularly limited, it is preferably 3 hours or less from the viewpoint of suppressing thermal decomposition of the cured film.
  • the step of forming through-holes in the cured film is then performed.
  • the through holes may be patterned.
  • the method for forming the through-hole is not particularly limited, and can be formed by laser irradiation such as CO 2 laser, etching, or the like.
  • the through hole is formed so as to penetrate the other layer and expose the electrode surface of the element.
  • the method for producing a laminate of the present invention then performs a step of forming an inorganic layer and/or a barrier metal layer as necessary.
  • the same inorganic layer and barrier metal layer as those used in the laminate of the present invention can be used.
  • the inorganic layer and the barrier metal layer can be formed by sputtering, vapor deposition, or the like.
  • the step of forming the inorganic layer is preferably performed before and/or after the step of forming the cured film. It is preferable that the formation of the barrier metal layer is performed after the step of forming the through holes.
  • the method for manufacturing a laminate of the present invention then performs a step of filling the through holes with a conductive material.
  • Plating or the like can be used as a method of filling the conductive material.
  • the conductive material the same conductive material as that of the laminate of the present invention can be used.
  • the step of polishing the surface of the conductive material-filled side of the first element to form a bonding electrode is then carried out.
  • a junction electrode connecting the electrodes formed on the two elements is formed.
  • the polishing preferably planarizes and removes the layer formed of the conductive material until the cured film is exposed or, if the inorganic layer is present, the inorganic layer is exposed.
  • the polishing method is not particularly limited, and for example, a chemical mechanical polishing method can be used.
  • the element having the bonding electrodes is a member for forming a laminate by bonding together so that the bonding electrodes between the elements are bonded to each other.
  • the elements, the cured film, the curable resin composition, and other configurations and steps are the same as those described for the curable resin composition, the laminate, and the method for producing the laminate of the present invention.
  • the first element having the bonding electrode formed thereon and the second element having the bonding electrode formed thereon are bonded together so that the bonding electrodes are bonded to each other.
  • a method of bonding the first element and the second element together there is a method of melting the electrodes and connection electrodes by heat treatment and connecting them. The heat treatment is usually performed at 400° C. for about 4 hours.
  • the use of the laminate of the present invention is not particularly limited. It can be suitably used for a laminate constituting an apparatus and an imaging apparatus.
  • a semiconductor device having such a laminate of the present invention and an imaging device having the laminate of the present invention are also one aspect of the present invention.
  • a laminated body using the cured film of the present invention in addition to the laminated body A, a plurality of chips electrically connected to the element are laminated, and the surface of the element on which the chips are laminated and the support substrate A laminate having a structure in which the cured film of the present invention is interposed is also included.
  • the supporting substrate and the elements and chips are not electrically connected, so the cured film of the present invention does not directly protect the electrical connection paths.
  • the cured film of the present invention is thick, film cracking is unlikely to occur at high temperatures, so warping and cracking of elements and chips caused by film cracking can be suppressed.
  • the electrical connection reliability between each chip can be improved.
  • the third element has a first surface and a second surface, and the first surface is the A laminated body in which a plurality of chips electrically connected to a third element are laminated and which has the cured film between the first surface and the supporting substrate is also one aspect of the present invention. (hereinafter referred to as laminate B).
  • the laminate B of the present invention has a support substrate.
  • the support substrate include glass and single crystal silicon.
  • a laminate B of the present invention has a third element having a first surface and a second surface, and a plurality of chips electrically connected to the third element are laminated on the first surface.
  • the third element the same elements as the first element and the second element can be used.
  • the chip include memory circuit elements, logic circuit elements, and the like. These multiple chips may be of a single type or a combination of different types.
  • the above-mentioned "electrically connected" has the same meaning as that of the laminated body A above.
  • the laminate B of the present invention preferably has an inorganic layer between the support substrate and the cured film.
  • the insulation can be further improved.
  • the inorganic layer the same inorganic layer as that of the laminate A can be used.
  • the laminate B of the present invention further has a fourth element on the second surface of the third element, and the third element and the fourth element are electrically connected.
  • the fourth element can be the same as the first to third elements.
  • FIG. 3 shows a diagram schematically showing one aspect of the laminate B of the present invention.
  • a plurality of chips 9 electrically connected to the third element 8 are laminated on the first surface of the third element 8.
  • a fourth element 10 electrically connected to the third element 8 is laminated on the second surface, which is the opposite surface, and the first surface of the third element 8 and the support substrate 11 are cured. It has a laminated structure with the film 4 interposed therebetween.
  • the portion of the cured film 4 that corresponds to the insulating layer is made of a hard inorganic material, so when warping occurs in the element or laminate, it cannot be eliminated by stress relaxation, and cracks occur in the element or chip. something happened.
  • the warpage of the element or chip can be eliminated by stress relaxation, so that the element can have high electrical connection reliability. be able to.
  • film cracking is less likely to occur due to high temperatures, so warping and cracking of elements and chips can be further suppressed.
  • FIG. 4 shows a diagram schematically showing one aspect of the laminate of the present invention.
  • an inorganic layer 6 is provided between the cured film 4 and the support substrate, and the insulation is further enhanced. Since the thickness of the inorganic layer 6 of the present invention may be significantly thinner than the insulating layer of the conventional laminate, it does not hinder the elimination of warpage of the element or laminate.
  • a step of forming a film of the curable resin composition of the present invention on the first surface of the third element drying the solvent, and then curing to form a cured film. and a step of bonding together the first surface of the third element on which the cured film is formed and the support substrate.
  • the curable resin composition of the present invention is formed as a film on the first surface of the third element, and the solvent is dried and then cured to form a cured film.
  • the curable resin composition of the present invention is resistant to film cracking due to high temperatures even when it is formed into a thick cured film. connection reliability can be given.
  • the film forming method and conditions are the same as those of the laminate A manufacturing method.
  • the step of forming an inorganic layer is then performed as necessary.
  • the method for forming the inorganic layer is the same as the method for producing the laminate A.
  • a step of bonding the first surface of the third element on which the cured film is formed and the support substrate is performed.
  • a method of bonding the third element and the support substrate together there is a method of chemically bonding the surfaces by heat treatment, and the like.
  • the heat treatment is usually performed at 400° C. for about 4 hours.
  • the use of the laminate B of the present invention is not particularly limited, it has high electrical connection reliability, and even when joining thin elements, warping and cracking of the elements and laminates can be suppressed. It can be suitably used for laminates constituting semiconductor devices and imaging devices. A semiconductor device and an imaging device having such a laminate B of the present invention are also one aspect of the present invention.
  • a curable resin composition that does not easily crack at high temperatures in a nitrogen atmosphere even when a thick film is formed, a cured film using the curable resin composition, and the cured film.
  • an imaging device and a semiconductor device having the laminate a method for manufacturing the laminate, and a method for manufacturing an element having a junction electrode used for manufacturing the laminate.
  • BRIEF DESCRIPTION OF THE DRAWINGS It is the figure which represented typically the one aspect
  • BRIEF DESCRIPTION OF THE DRAWINGS It is the figure which represented typically the one aspect
  • BRIEF DESCRIPTION OF THE DRAWINGS It is the figure which represented typically the one aspect
  • BRIEF DESCRIPTION OF THE DRAWINGS It is the figure which represented typically the one aspect
  • silsesquioxane derivative (DD(Me)-OH) (150 g), octamethylcyclotetrasiloxane (D4) (54.4 g), sulfuric acid (15.2 g), toluene (176 g), 4-methyl Tetrahydropyran (43.9 g) was added to the reactor and heated to 100° C. and stirred 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, aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate.
  • a polyimide C-BO (weight average molecular weight: 5600) having the structure of the above formula (3) at both ends of (14) was obtained. Also, by changing the molar ratio of PAM-E and 6FDA from 1:0.83 to 1:0.50, a polyimide C-BO having a weight average molecular weight of 2200 was obtained.
  • Example 1 100 parts by weight of main polymer A, 3.2 parts by weight of cross-linking agent (silicate MS-51, manufactured by Mitsubishi Chemical Co., Ltd.), 0.2 parts by weight of catalyst (ZC-162, manufactured by Matsumoto Fine Chemical Co., Ltd.), 1 part by weight of polyimide C-BSI, solvent A curable resin composition was obtained by mixing 67.5 parts by weight of ethyl benzoate.
  • cross-linking agent silicate MS-51, manufactured by Mitsubishi Chemical Co., Ltd.
  • catalyst ZC-162, manufactured by Matsumoto Fine Chemical Co., Ltd.
  • solvent A curable resin composition was obtained by mixing 67.5 parts by weight of ethyl benzoate.
  • Examples 2-9, 11-15, Comparative Examples 1-4 A curable resin composition was obtained in the same manner as in Example 1, except that the compositions were as shown in Tables 1 and 2.
  • Example 10 A curable resin composition was obtained in the same manner as in Example 1 except that ethyl benzoate was changed to a 1:1 mixed solvent of anisole and MEK and the composition was changed as shown in Table 1.
  • a curable resin composition in which film cracking is unlikely to occur at high temperatures even when a thick film is formed a cured film using the curable resin composition, and a laminate having the cured film , an imaging device and a semiconductor device having the laminate, a method for manufacturing the laminate, and a method for manufacturing an element having a bonding electrode used for manufacturing the laminate.

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PCT/JP2022/047305 2021-12-23 2022-12-22 硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置、積層体の製造方法及び接合電極を有する素子の製造方法 Ceased WO2023120627A1 (ja)

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CN202280069200.5A CN118139931A (zh) 2021-12-23 2022-12-22 固化性树脂组合物、固化膜、层叠体、拍摄装置、半导体装置、层叠体的制造方法和具有接合电极的元件的制造方法
US18/720,896 US20250051573A1 (en) 2021-12-23 2022-12-22 Curable resin composition, cured film, laminate, imaging device, semiconductor device, method for manufacturing laminate, and method for manufacturing element having contact electrode
EP22911329.5A EP4455224A4 (en) 2021-12-23 2022-12-22 Composition of hardenable resin, hardened film, laminate, imaging device, semiconducting device, method for manufacturing a laminate and method for manufacturing an element comprising a contact electrode
JP2023503049A JP7425257B2 (ja) 2021-12-23 2022-12-22 硬化性樹脂組成物、硬化膜、積層体、撮像装置、半導体装置、積層体の製造方法及び接合電極を有する素子の製造方法
KR1020247007674A KR20240121703A (ko) 2021-12-23 2022-12-22 경화성 수지 조성물, 경화막, 적층체, 촬상 장치, 반도체 장치, 적층체의 제조 방법 및 접합 전극을 갖는 소자의 제조 방법
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