Method for manufacturing semiconductor device, semiconductor device, and curable resin composition

Abstract

A method of manufacturing a semiconductor device includes: preparing a first circuit member having a first substrate, a first electrode, and a first insulating film; preparing a second circuit component, wherein the second circuit component is provided with a second substrate, a second electrode and a second insulating film; and bonding the first circuit member and the second circuit member such that the first insulating film and the second insulating film are bonded and the first electrode and the second electrode are bonded by heating and pressurizing the first circuit member and the second circuit member. At least one of the first substrate and the second substrate is a semiconductor substrate having a circuit surface. At least one of the first insulating film and the second insulating film is an organic insulating film containing a cured product of a curable resin composition containing a maleimide compound having a maleimide group and an allyl compound having an allyl group.

Description

Technical Field

[0001] The present invention relates to a method for manufacturing a semiconductor device, a semiconductor device, and a curable resin composition. Background Art

[0002] In the three-dimensional packaging of semiconductor chips, hybrid bonding technology, which combines electrodes with insulating films to achieve miniaturization of wiring, is being studied. A proposal has also been made to use resin materials such as polyimide to form insulating films for hybrid bonding technology (Patent Document 1).

[0003] On the other hand, it is known that a composition containing a maleimide compound and an allyl compound is thermally cured by an addition reaction including an ene reaction and a Diels-Alder reaction or by radical polymerization (Non-Patent Document 1).

[0004] Previous technical literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2020 / 085183

[0007] Non-patent literature

[0008] Non-Patent Literature 1: Handbook of Thermoset Plastics, Third Edition, 2014, pp. 459-510 Summary of the Invention

[0009] Technical issues to be solved by the invention

[0010] An organic insulating film formed of a resin material is expected to have advantages over an inorganic insulating film in terms of reducing the influence of debris, etc. The present invention relates to a method for manufacturing a semiconductor device based on a novel hybrid bonding technology using an organic insulating film as a bonding material.

[0011] Means for solving technical problems

[0012] The present invention includes the following. [1]

[0014] A method for manufacturing a semiconductor device comprises the following steps:

[0015] preparing a first circuit component, the first circuit component including a first substrate, a first electrode, and a first insulating film, wherein the first electrode and the first insulating film are provided on the first substrate, the first insulating film is formed with an opening, and the first electrode is provided in the opening;

[0016] preparing a second circuit component, the second circuit component including a second substrate, a second electrode, and a second insulating film, wherein the second electrode and the second insulating film are provided on the second substrate, the second insulating film is formed with an opening, and the second electrode is provided in the opening; and

[0017] The first circuit component and the second circuit component are heated and pressurized, thereby bonding the first circuit component and the second circuit component such that the first insulating film is bonded to the second insulating film and the first electrode is bonded to the second electrode.

[0018] At least one of the first substrate or the second substrate is a semiconductor substrate having a circuit surface.

[0019] When the first substrate is a semiconductor substrate having a circuit surface, the first electrode and the first insulating film are provided on the circuit surface; when the second substrate is a semiconductor substrate having a circuit surface, the second electrode and the second insulating film are provided on the circuit surface.

[0020] At least one of the first insulating film and the second insulating film is an organic insulating film including a cured product of a curable resin composition including a maleimide compound having a maleimide group and an allyl compound having an allyl group. [2]

[0022] The method according to [1], wherein

[0023] When the first insulating film is the organic insulating film, the first circuit component is prepared by a method including the steps of forming a resin film containing the curable resin composition on the first substrate and curing the resin film.

[0024] When the second insulating film is a cured product of the curable resin composition, the second circuit component is prepared by a method including forming a resin film containing the curable resin composition on the second substrate and curing the resin film. [3]

[0026] The method according to [1] or [2], wherein

[0027] The first insulating film and the second insulating film are the organic insulating films. [4]

[0029] A semiconductor device comprising:

[0030] a first circuit component comprising a first substrate, a first electrode, and a first insulating film, wherein the first electrode and the first insulating film are provided on the first substrate, the first insulating film is formed with an opening, and the first electrode is provided in the opening; and

[0031] a second circuit component joined to the first circuit component and comprising a second substrate, a second electrode, and a second insulating film, wherein the second electrode and the second insulating film are provided on the second substrate, the second insulating film is formed with an opening, and the second electrode is provided in the opening;

[0032] The first circuit component and the second circuit component are bonded together in such a manner that the first insulating film and the second insulating film are bonded together and the first electrode and the second electrode are bonded together.

[0033] At least one of the first substrate or the second substrate is a semiconductor substrate having a circuit surface.

[0034] When the first substrate is a semiconductor substrate having a circuit surface, the first electrode and the first insulating film are provided on the circuit surface; when the second substrate is a semiconductor substrate having a circuit surface, the second electrode and the second insulating film are provided on the circuit surface.

[0035] At least one of the first insulating film and the second insulating film is an organic insulating film including a cured product of a curable resin composition including a maleimide compound having a maleimide group and an allyl compound having an allyl group. [5]

[0037] The semiconductor device according to [4], wherein

[0038] The first insulating film and the second insulating film are the organic insulating films. [6]

[0040] A curable resin composition comprising a maleimide compound having a maleimide group and an allyl compound having an allyl group, and used for forming an organic insulating film in the method described in any one of [1] to [3]. [7]

[0042] A use of a curable resin composition for producing a semiconductor device by the method described in any one of [1] to [3], wherein the curable resin composition comprises a maleimide compound having a maleimide group and an allyl compound having an allyl group.

[0043] Effects of the Invention

[0044] Provided is a method for manufacturing a semiconductor device based on a novel hybrid bonding technology using an organic insulating film as a bonding material. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] Figure 1 This is a process diagram showing an example of a method for manufacturing a semiconductor device.

[0046] Figure 2 This is a process diagram showing an example of a method for manufacturing a semiconductor device.

[0047] Figure 3 This is a process diagram showing an example of a method for manufacturing a semiconductor device. DETAILED DESCRIPTION

[0048] The present invention is not limited to the following examples.

[0049] (Method for Manufacturing Semiconductor Device)

[0050] Figure 1 、 Figure 2 and Figure 3 This is a process diagram showing an example of a method for manufacturing a semiconductor device. Figures 1 to 3 The method shown includes the following steps: preparing a first circuit component 10 having a first substrate 11, a first electrode 12, and a first insulating film 13; preparing a second circuit component 20 having a second substrate 21, a second electrode 22, and a second insulating film 23; and heating and pressurizing the first and second circuit components 10, 20 to bond them together so that the first insulating film 13 is bonded to the second insulating film 23 and the first electrode 12 is bonded to the second electrode 22. At least one of the first substrate 11 or the second substrate 21 can be a semiconductor substrate having a circuit surface. Typically, an integrated circuit is provided on the circuit surface of the semiconductor substrate. This method forms a semiconductor device 1, which is a bonded structure of the first and second circuit components 10, 20. For example, the first substrate 11 can be a semiconductor wafer, and the second substrate 21 can be a semiconductor chip. Multiple second circuit components 20 having semiconductor chips can be bonded to a single first circuit component 10 having a semiconductor wafer. In this case, the semiconductor wafer (first substrate 11) of the obtained bonded body can be singulated to form a plurality of semiconductor chips. The semiconductor substrate can be, for example, a silicon substrate. When the first circuit component 10 or the second circuit component 20 is not a semiconductor substrate, these can be various wiring substrates (e.g., interposers).

[0051] In the first circuit component 10 before bonding, the first electrode 12 and the first insulating film 13 are provided on the first substrate 11. When the first substrate 11 is a semiconductor substrate having a circuit surface, the first electrode 12 and the first insulating film 13 are provided on the circuit surface. The first insulating film 13 is formed with a plurality of openings 13a, which serve as through-holes through which the first substrate 11 is exposed, and the first electrodes 12 are provided in the openings 13a.

[0052] In the second circuit component 20 before bonding, the second electrode 22 and the second insulating film 23 are provided on the second substrate 21. When the second substrate 21 is a semiconductor substrate, the second electrode 22 and the second insulating film 23 are provided on the circuit surface. The second insulating film 23 has a plurality of openings 23a formed therein, which serve as through-holes through which the second substrate 21 is exposed. The second electrodes 22 are provided in the openings 23a.

[0053] The shapes of the first electrode 12 and the second electrode 22 are not particularly limited, but some or all of these electrodes are configured in such a manner that the first electrode 12 and the second electrode 22 are opposed to each other and bonded. The width of the first electrode 12 and the second electrode 22 can be, for example, greater than 1 μm or greater than 100 μm, or less than 300 μm or less than 30 μm. The width here refers to the maximum width of each electrode in a direction parallel to the main surface (circuit surface) of the first substrate 11 or the second substrate 21. The spacing between adjacent first electrodes 12 and the spacing between adjacent second electrodes 22 can be, for example, greater than 1 μm or greater than 100 μm, or less than 300 μm or less than 30 μm. The height of the first electrode 12 and the second electrode 22 can be, for example, greater than 1 μm or greater than 10 μm, or less than 100 μm or less than 10 μm. The height of the first electrode 12 can be the same as or different from the thickness of the first insulating film 13. The height of the second electrode 22 can be the same as or different from the thickness of the second insulating film 23.

[0054] At least one of the first insulating film 13 or the second insulating film 23 can be an organic insulating film of a cured product comprising a curable resin composition (hereinafter also referred to as a "curable maleimide resin composition"), wherein the curable resin composition comprises a maleimide compound having a maleimide group and an allyl compound having an allyl group. The organic insulating film comprising a cured product of the curable maleimide resin composition can be well bonded to other insulating films by heating and pressurizing. On the surface of the organic insulating film comprising a cured product of the curable maleimide resin composition, there may be many maleimide groups, allyl groups or functional groups derived from these. Therefore, for example, activation treatments such as plasma treatment are not necessarily required for the organic insulating film to exhibit good bonding properties. In addition, it is possible to adjust the polishing speed of the organic insulating film according to the crosslinking density in the cured product, etc. More detailed examples of curable maleimide resin compositions will be described later.

[0055] When both the first insulating film 13 and the second insulating film 23 are organic insulating films comprising a cured product of a curable maleimide resin composition, particularly good bonding properties are likely to be exhibited. However, either the first insulating film 13 or the second insulating film 23 may be an organic insulating film other than an organic insulating film comprising a cured product of a curable maleimide resin composition, or may be an inorganic insulating film.

[0056] When the first insulating film 13 is an organic insulating film including a cured product of a curable maleimide resin composition, as shown in FIG. Figure 1 and Figure 2 As shown, the first circuit component 10 can be prepared by a method including the following steps: providing a plurality of columnar first electrodes 12 on a main surface 11S of a first substrate 11; forming a resin film 13A containing a curable resin composition (curable maleimide resin composition) and covering the first electrode 12 on the main surface 11S on the first electrode 12 side of the first substrate 11; curing the resin film 13A to form a first insulating film 13 as an organic insulating film; and grinding the first insulating film 13 from the side opposite to the first substrate 11 to form an opening 13a in the first insulating film 13 for exposing the first electrode 12.

[0057] The first electrode 12 is formed of a conductive material containing a metal such as copper. The first electrode 12 containing a metal can be formed by a common method such as a plating method.

[0058] After the first electrode 12 is formed, a resin film 13A containing a curable resin composition is formed on the main surface 11S on the first electrode 12 side of the first substrate 11. The resin film 13A is formed, for example, by applying a curable resin composition having fluidity. The curable resin composition having fluidity may contain a solvent. When a curable resin composition containing a solvent is used, the resin film 13A can be formed by heating the applied curable resin composition to remove the solvent. The heating temperature for removing the solvent may be, for example, 60°C or higher and 150°C or lower. The resin film 13A may be formed to fill the gaps between the plurality of first electrodes 12 and cover the entire first electrode 12.

[0059] The formed resin film 13A is cured by heating. The first insulating film 13 (organic insulating film) as a cured product of the curable resin composition is formed by curing the resin film 13A. By heating, an ene reaction between the maleimide group and the allyl group, a Diels-Alder reaction accompanied by the addition of the maleimide group, and free radical polymerization are carried out to form a cured product. Since curing is mainly carried out by addition reaction, volatile components caused by detached components are not easily generated. In addition, since curing is carried out at a relatively low temperature, thermal damage to semiconductor substrates and the like can be reduced. The heating temperature for curing the resin film 13A can be, for example, above 170°C and below 260°C. The heating time for curing the resin film 13A can be, for example, above 60 minutes and below 180 minutes.

[0060] When the formed first insulating film 13 covers the first electrode 12, the first insulating film 13 is ground from the side opposite to the first substrate 11. As a method of grinding, a common method such as chemical mechanical polishing (CMP) can be used. By this grinding, a portion of the first insulating film 13 is removed, and an opening 13a of the first insulating film 13 is formed to expose the first electrode 12. Usually, a portion of the first electrode 12 is also removed by grinding, thereby flattening the surface of the front end of the first electrode 12 (the surface on the side opposite to the first substrate 11). Due to the difference in grinding speed, the height of the first electrode 12 in the first circuit component 10 after grinding can be greater than the thickness of the first insulating film 13. The difference between the height of the first electrode 12 and the thickness of the first insulating film 13 can be adjusted by taking into account the difference in the linear thermal expansion coefficient of the first electrode 12 and the first insulating film 13. The difference between the height of the first electrode 12 and the thickness of the first insulating film 13 can be, for example, greater than 0.1 μm and less than 0.5 μm.

[0061] From the perspective of electrode bonding, the surface of the tip of the first electrode 12 may have a surface roughness Ra of 1 nm or less. The surface of the tip of the second electrode 22 may also have the same surface roughness Ra. The surface roughness Ra here is the arithmetic mean roughness (Ra) specified in JIS B 0601-2001.

[0062] The second circuit member 20 can also be prepared in the same manner as above. The second electrode 22 and the second insulating film 23 may have the same shape (including height, thickness, and surface roughness Ra) as the first electrode 12 and the first insulating film 13 .

[0063] like Figure 2 As shown in (e), the prepared first circuit component 10 and second circuit component 20 are aligned in such a manner that the first electrode 12 and the second electrode 22 to be bonded are opposed to each other. Figure 3As shown, the first circuit member 10 and the second circuit member 20 are heated and pressurized to bond the first electrode 12 to the second electrode 22 and the first insulating film 13 to the second insulating film 23 .

[0064] The bonding of the first electrode 12 and the second electrode 22 and the bonding of the first insulating film 13 and the second insulating film 23 may be performed simultaneously or sequentially. For example, after heating and pressurizing the first insulating film 13 and the second insulating film 23, the first circuit component 10 and the second circuit component 20 may be further heated and pressurized to bond the first electrode 12 and the second electrode 22.

[0065] The heating and pressurizing conditions for bonding are adjusted to appropriately bond the insulating film and the electrode. For example, the heating temperature for bonding can be between 150°C and 250°C, and the pressure for bonding can be between 1.0 MPa and 5.0 MPa. The heating and pressurizing time can be, for example, between 10 seconds and 1 hour.

[0066] Curable resin composition

[0067] In the above manufacturing method, the curable resin composition for forming the organic insulating film (the first insulating film 13 and / or the second insulating film 23 ) may be a curable maleimide resin composition containing a maleimide compound having a maleimide group and an allyl compound having an allyl group.

[0068] The maleimide compound is a compound having one or more maleimide groups. From the viewpoint of reducing the heat resistance and thermal expansion coefficient of the cured product, the curable maleimide resin composition may contain a maleimide compound having two or more maleimide groups.

[0069] The maleimide compound may have an imide group containing a nitrogen atom directly bonded to a cyclic group (eg, an aromatic group). For example, the maleimide compound in the curable maleimide resin composition may contain a compound represented by the following formula (Ia) or (Ib).

[0070]

[0071] In formula (Ia), Q 1 and Q 2 Each independently represents a cyclic group which may have a substituent, L 1 represents a divalent organic group or a single bond. 1 and Q 2 L may be independently an aromatic group (for example, a phenylene group). 1It may be a group selected from a monocyclic ring, a condensed ring, a non-condensed bridged ring, and a spirocyclic ring containing one or more cyclic groups (excluding maleimide groups) which may have a substituent, a linear alkylene group which may have a substituent (for example, a methylene group, a propane-1,3-diyl group), a propane-2,2-diyl group which may have a substituent, or a single bond. 1 It may have two or more cyclic groups and a single bond connecting the two or more cyclic groups, or a divalent organic group (for example, a methylene group which may have a substituent, or a propane-2,2-diyl group which may have a substituent). 1 It may further have a linking cyclic group and Q 1 or Q 2 The methylene group. 1 The cyclic group in L may be substituted by a methyl group or a maleimide group, for example. 1 It may have a cyclic group obtained by removing one or more hydrogen atoms from benzene, 2,3-dihydro-1H-indene, or succinimide.

[0072] In formula (Ib), Q 3 represents a cyclic group which may have a substituent. 3 It may be an aromatic group (e.g., phenylene). 3 The cyclic group in may be substituted by, for example, a methyl group or a maleimide group.

[0073] Specific examples of the maleimide compound include compounds represented by the following formula 11, 12, 13, or 14. In these formulas, n represents an integer of 1 or greater.

[0074]

[0075]

[0076] Examples of commercially available maleimide compounds include NE-X-9470S (trade name, DIC), MIR-3000-70MT (trade name, Nippon Kayaku Co., Ltd.), BMI-2300 (trade name, Daiwa Kasei Industry Co., Ltd.), BMI-5100 (trade name, Daiwa Kasei Industry Co., Ltd.), BMI-80 (trade name, Daiwa Kasei Industry Co., Ltd.), BMI (trade name, Daiwa Kasei Industry Co., Ltd.) and SFR-2300MR-T (trade name, Showa Denko Materials Co., Ltd.).

[0077] The allyl compound is a compound having one or more allyl groups (2-propenyl, -CH2CH=CH2). From the viewpoint of reducing the heat resistance and thermal expansion coefficient of the cured product, the curable maleimide resin composition may contain an allyl compound having two or more allyl groups.

[0078] The allyl compound may include a compound having a cyclic group and an allyl group or an allyloxy group directly bonded to the cyclic group. For example, the allyl compound in the curable maleimide resin composition may include a compound represented by the following formula (IIa), (IIb), (IIc), or (IId).

[0079]

[0080] In formula (IIa) and (IIb), Q 4 and Q 5 Each independently represents a cyclic group which may have a substituent, L 2 represents a divalent organic group or a single bond. 4 and Q 5 Each of them may independently be benzene, isocyanuric acid or a group obtained by removing one or more hydrogen atoms from nadicimide. 2 It may be a group containing one or more cyclic groups (excluding maleimide groups) selected from a monocyclic ring, a condensed ring, a non-condensed bridged ring, and a spirocyclic ring, which may have a substituent, a linear alkylene group (for example, a methylene group, a propane-1,3-diyl group), a propane-2,2-diyl group, or a single bond. 2 It may have two or more cyclic groups and a single bond connecting the two or more cyclic groups, or a divalent organic group (for example, a methylene group which may have a substituent, or a propane-2,2-diyl group which may have a substituent). 2 It may further have a linking cyclic group and Q 4 or Q 5 The methylene group. 2 The cyclic group in L may be substituted by a substituent selected from, for example, a methyl group, a hydroxyl group, and an allyl group. 2 It may have a phenylene group, and the phenylene group may have a substituent.

[0081] In formula (IIc) and (IId), Q 6 represents a cyclic group which may have a substituent. 6 It may be an aromatic group (e.g., phenylene) or a group obtained by removing one or more hydrogen atoms from isocyanuric acid. 3 The cyclic group in may be substituted, for example, by a methyl group or an allyl group.

[0082] Specific examples of the allyl compound include compounds represented by the following formula 21, 22, 23, 24, 25, 26, 27, 28, or 29. In these formulas, n represents an integer of 1 or greater.

[0083]

[0084]

[0085]

[0086] Examples of commercially available allyl compounds include DABPA (trade name, KANTO CHEMICAL CO., INC.), DA-BPF (trade name, Yokkaichi Chemical Co., Ltd.), LVA01 (trade name, Gun Ei Chemical Industry Co., Ltd.), BPA-AE (trade name, KONISHI CHEMICAL IND CO., Ltd.), BANI-X (trade name, Maruzen Petrochemical Co., Ltd.), BANI-M (trade name, Maruzen Petrochemical Co., Ltd.), FATC-809 (trade name, Gun Ei Chemical Industry Co., Ltd.), FATC-809AP (trade name, Gun Ei Chemical Industry Co., Ltd.), DAIC (trade name, SHIKOKU CHEMICALS CORPORATION), and DD-1 (trade name, SHIKOKU CHEMICALS CORPORATION).

[0087] The content of the allyl compound may be 10% by mass or more and 70% by mass or less, based on the total amount of the maleimide compound and the allyl compound. The content of the allyl compound may be 15% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or less, or 65% by mass or less, 60% by mass or less, or 55% by mass or less, based on the total amount of the maleimide compound and the allyl compound.

[0088] The curable maleimide resin composition may further contain a component that initiates or accelerates the reaction of the maleimide compound and the allyl compound.

[0089] The curable maleimide resin composition may further contain a component that reduces the dielectric loss tangent of the cured product (hereinafter referred to as a "dielectric loss tangent modifier"). The dielectric loss tangent modifier includes, for example, an aromatic compound represented by the following formula (IIIa), (IIIb), or (IIIc).

[0090]

[0091] In formula (IIIa), R 11 、R 14 and R 15 Each independently represents a hydrogen atom, a methyl group or a tert-butyl group, R 12 and R 13 Each independently represents a hydrogen atom, a hydroxyl group or an organic group having 1 to 30 carbon atoms, and Z 1 It represents an organic group having 7 to 80 carbon atoms and containing at least one heteroatom selected from the group consisting of sulfur, phosphorus, oxygen, and nitrogen, or an organic group having 2 to 15 carbon atoms and containing a carbonyl group.

[0092] In formula (IIIb), R 16 、R 19 、R 20 、R 21 、R 22 and R 25 Each independently represents a hydrogen atom, a methyl group or a tert-butyl group, R 17 、R 18 、R 23 and R 24 Each independently represents a hydrogen atom, a hydroxyl group or an organic group having 1 to 30 carbon atoms, and Z 2 It represents a divalent organic group having 1 to 50 carbon atoms or a divalent organic group having 1 to 75 carbon atoms, containing at least one heteroatom selected from the group consisting of sulfur, phosphorus, oxygen, and nitrogen.

[0093] In formula (IIIc), R 26 、R 29 、R 30 、R 31 、R 34 、R 35 、R 36 、R 37 and R 40 Each independently represents a hydrogen atom, a methyl group or a tert-butyl group, R 27 、R 28 、R 32 、R 33 、R 38 and R 39 Each independently represents a hydrogen atom, a hydroxyl group or an organic group having 1 to 30 carbon atoms, and Z 3It represents a trivalent organic group having 1 to 50 carbon atoms and containing at least one heteroatom selected from the group consisting of sulfur, phosphorus, oxygen, and nitrogen, or a trivalent organic group having 1 to 50 carbon atoms.

[0094] The content of the dielectric loss tangent modifier can be 1% by mass or more and 50% by mass or less, based on the total amount of the maleimide compound and the allyl compound. The content of the dielectric loss tangent modifier can be 2% by mass or more or 5% by mass or less, and can be 50% by mass or less or 40% by mass or less, based on the total amount of the maleimide compound and the allyl compound.

[0095] The curable maleimide resin composition may further contain a solvent for dissolving or dispersing the maleimide compound and the allyl compound. Examples of the solvent include γ-butyrolactone, cyclohexanone, cyclopentanone, mesitylene, N,N-dimethylformamide, propylene glycol monomethyl ether acetate, and ethyl lactate.

[0096] The curable maleimide resin composition may further contain an adhesion promoter. The adhesion promoter may include, for example, a silane coupling agent, an aluminum-based adhesion promoter, or a combination thereof.

[0097] Examples of silane coupling agents include γ-aminopropyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, 3-methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinylpropylsilane, diethoxy-3-glycidoxypropyltrimethoxysilane, Propylmethylsilane, N-(3-diethoxymethylsilylpropyl)succinimide, N-[3-(triethoxysilyl)propyl]phthalamic acid, benzophenone-3,3'-bis(N-[3-triethoxysilyl]propylamide)-4,4'-dicarboxylic acid, benzene-1,4-bis(N-[3-triethoxysilyl]propylamide)-2,5-dicarboxylic acid, 3-(triethoxysilyl)propylsuccinic anhydride, and N-phenylaminopropyltrimethoxysilane.

[0098] Examples of aluminum-based adhesion promoters include tris(ethyl acetoacetate)aluminum, tris(acetylacetonate)aluminum, and ethyl acetoacetate aluminum diisopropoxide.

[0099] The content of the adhesion promoter may be, for example, 0.5% by mass or more and 25% by mass or less based on the total amount of the maleimide compound and the allyl compound.

[0100] The curable maleimide resin composition may further contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, N-nitrosodiphenylamine, p-tert-butylcatechol, 4-methoxyphenol, phenothiazine, N-phenylnaphthylamine, ethylenediaminetetraacetic acid, 1,2-cyclohexanediaminetetraacetic acid, glycol ether diaminetetraacetic acid, 2,6-di-tert-butyl-p-methylphenol, 5-nitroso-8-hydroxyquinoline, 1-nitroso-2-naphthol, 2-nitroso-1-naphthol, 2-nitroso-5-(N-ethyl-N-sulfopropylamino)phenol, N-nitroso-N-phenylhydroxylamine ammonium salt, and N-nitroso-N(1-naphthyl)hydroxylamine ammonium salt.

[0101] The content of the polymerization inhibitor may be 0.005% by mass or more and 12% by mass or less based on the total amount of the maleimide compound and the allyl compound.

[0102] The curable maleimide resin composition may further contain an azole compound. Examples of the azole compound include 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole, 4-tert-butyl-5-phenyl-1H-triazole, 5-hydroxyphenyl-1H-triazole, phenyltriazole, p-ethoxyphenyltriazole, 5-phenyl-1-(2-dimethylaminoethyl)triazole, 5-benzyl-1H-triazole, hydroxyphenyltriazole, 1,5-dimethyltriazole, 4,5-diethyl-1H-triazole, 1H-benzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)] )phenyl]-benzotriazole, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)benzotriazole, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-benzotriazole, 2-(3,5-di-tert-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, hydroxyphenylbenzotriazole, tolyltriazole, 5-methyl-1H-benzotriazole, 4-methyl-1H-benzotriazole, 4-carboxy-1H-benzotriazole, 5-carboxy-1H-benzotriazole, 1H-tetrazole, 5-methyl-1H-tetrazole, 5-phenyl-1H-tetrazole, 5-amino-1H-tetrazole and 1-methyl-1H-tetrazole.

[0103] The content of the azole compound may be 0.1% by mass to 20% by mass, or 0.5% by mass to 5% by mass, based on the total amount of the maleimide compound and the allyl compound.

[0104] The curable maleimide resin composition may contain a hindered phenol compound. Examples of the hindered phenol compound include 2,6-di-tert-butyl-4-methylphenol, 2,5-di-tert-butylhydroquinone, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, isooctyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-thio-bis(3-methyl-6-tert-butylphenol), 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], and the like. esters], 2,2-thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamic acid), 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), 2,2'-methylene-bis(4-ethyl-6-tert-butylphenol), pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris(3-hydroxy-2 ,6-dimethyl-4-isopropylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-sec-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris[4-(1-ethylpropyl)-3-hydroxy-2,6-dimethylbenzyl]-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris[4- triethylmethyl-3-hydroxy-2,6-dimethylbenzyl]-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(3-hydroxy-2,6-dimethyl-4-phenylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,5,6-trimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione,5-Tris(4-tert-butyl-6-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-6-ethyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5,6-diethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione )-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione and 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione.

[0105] The content of the hindered phenol compound may be 0.1% by mass to 20% by mass, or 0.5% by mass to 10% by mass, based on the total amount of the maleimide compound and the allyl compound.

[0106] The curable maleimide resin composition may contain an organic titanium compound. The organic titanium compound may be, for example, a titanium chelate compound having two or more alkoxy groups, a tetraalkoxytitanium compound, a titanocene compound, a monoalkoxytitanium compound, a titanium oxide compound, a tetraacetylacetonate titanium compound, a titanate coupling agent, or a combination thereof.

[0107] Examples of titanium chelates having two or more alkoxy groups include bis(triethanolamine)diisopropoxytitanium, di(n-butoxy)bis(2,4-pentanedione)titanium, diisopropoxybis(2,4-pentanedione)titanium, diisopropoxybis(tetramethylheptanedione)titanium, and diisopropoxybis(ethyl acetoacetate)titanium.

[0108] Examples of tetraalkoxytitanium compounds include tetra(n-butoxy)titanium, tetraethoxytitanium, tetra(2-ethylhexyloxy)titanium, tetraisobutoxytitanium, tetraisopropoxytitanium, tetramethoxytitanium, tetramethoxypropoxytitanium, tetramethylphenoxytitanium, tetra(n-nonoxy)titanium, tetra(n-propoxy)titanium, tetrastearyloxytitanium, and tetra[bis{2,2-(allyloxymethyl)butoxy}]titanium.

[0109] Examples of the titanocene compound include pentamethylcyclopentadienyltrimethoxytitanium, bis(η5-2,4-cyclopentadien-1-yl)bis(2,6-difluorophenyl)titanium, and bis(η5-2,4-cyclopentadien-1-yl)bis(2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl)titanium.

[0110] Examples of the monoalkoxy titanium compound include tris(dioctyl phosphate)isopropoxytitanium and tris(dodecylbenzenesulfonate)isopropoxytitanium.

[0111] Examples of the titanium oxide compound include bis(pentanedione)titanium oxide, bis(tetramethylheptanedione)titanium oxide, and titanium phthalocyanine oxide.

[0112] Examples of the titanium tetraacetylacetonate compound include titanium tetraacetylacetonate.

[0113] As an example of the titanate coupling agent, isopropyl tridodecylbenzenesulfonyl titanate can be mentioned.

[0114] The content of the organic titanium compound may be 0.05% by mass or more and 10% by mass or less, or 0.1% by mass or more and 2% by mass or less, based on the total amount of the maleimide compound and the allyl compound.

[0115] [Example]

[0116] raw material

[0117] The following maleimide compounds and allyl compounds were prepared.

[0118] Maleimide compounds

[0119] Phenylmethanemaleimide (compound of formula 13, BMI-2300, Daiwa Kasei Industry Co., Ltd.)

[0120] 4,4'-Diphenylmethanebismaleimide (compound of formula 14, BMI, Daiwa Kasei Industry Co., Ltd.)

[0121] Allyl compounds

[0122] Arylphenol resin (compound of formula 23, LVA01, Gun Ei Chemical Industry Co., Ltd.)

[0123] 2,2'-Diallylbisphenol A (DABPA, KANTO CHEMICAL CO., INC.)

[0124] Compound of formula 25 (BATE, synthesized according to conventional methods)

[0125] Bisallylnadic acid imide (compound of formula 29, BANI-M, Maruzen Petrochemical Co., Ltd.)

[0126] (Examples 1 to 4)

[0127] (1) Evaluation of thermal properties of organic insulating films

[0128] A resin composition was prepared by melting and mixing a maleimide compound and an allyl compound in the proportions (parts by mass) shown in Table 1 by heating. The resin composition was applied to a substrate using a bar coater to form a resin film. The resin film was heated at 175°C for 1 hour, 200°C for 30 minutes, and 250°C for 1 hour. This heating cured the resin film. The curing of the resin film formed an organic insulating film having a thickness of 100 μm.

[0129] (2) Glass transition temperature (Tg)

[0130] The Tg of the organic insulating film was measured by dynamic viscoelasticity measurement (DMA) under the following conditions: The temperature at which Tan δ showed a maximum value was recorded as Tg.

[0131] Frequency: 10Hz

[0132] Heating rate: 5℃ / min

[0133] (3) Coefficient of linear thermal expansion (CTE)

[0134] The linear thermal expansion coefficient (CTE) of the organic insulating film was measured by the TMA method. The CTE was calculated within the temperature range of 50°C to 100°C. The measurement results are shown in Table 1.

[0135] [Table 1]

[0136]

[0137] (4) Bonding test

[0138] The curable resin composition of Example 2 was applied to a silicon wafer (diameter: 8 inches) by a spin coater. The coating was heated at 175°C for 1 hour, at 200°C for 30 minutes, and at 250°C for 1 hour. The resin film was cured by this heating. An organic insulating film with a thickness of 10 μm was formed by the curing of the resin film. The silicon wafer and the organic insulating film were singulated together by blade dicing to obtain a lower test piece with a size of 8 mm × 8 mm and an upper test piece with a size of 4 mm × 4 mm. The upper test piece was overlapped in the center of the organic insulating film of the lower test piece in a direction in which the organic insulating films were in contact with each other. In this state, the laminate of the lower test piece and the upper test piece was heated to 250°C and pressurized at a pressure of 2.6 MPa for 1 hour. By this heating and pressurization, a joint body in which the organic insulating film of the lower test piece and the organic insulating film of the upper test piece were joined was formed. A peel test was conducted on the upper test piece of the bonded structure, applying stress along the bonding surface of the organic insulating film, to measure the shear strength at 60°C. The peel test showed peeling in a mode that would cause the silicon wafer to break, resulting in a shear strength of 16.3 MPa. This result confirms that organic insulating films formed from a curable resin composition containing a maleimide compound and an allyl compound can be bonded to each other.

[0139] (Examples 5 to 8)

[0140] A resin composition was prepared by melting and mixing the maleimide compound and the allyl compound in the mixing ratio (parts by mass) shown in Table 2 by heating. The resin composition was applied to a substrate by a rod coater to form a resin film. The resin film was heated at 175°C for 1 hour, at 200°C for 30 minutes, and at 250°C for 1 hour in sequence. The resin film was cured by this heating. An organic insulating film with a thickness of 100 μm was formed by curing the resin film. The Tg of the organic insulating film was measured in the same manner as in Examples 1 to 4.

[0141] [Table 2]

[0142]

[0143] Explanation of symbols

[0144] 1- semiconductor device, 10- first circuit component, 11- first substrate, 12- first electrode, 13- first insulating film, 13a, 23a- openings, 13A- resin film, 20- second circuit component, 21- second substrate, 22- second electrode, 23- second insulating film.

Claims

1. A method for manufacturing a semiconductor device, comprising the following steps: A first circuit component is prepared, wherein the first circuit component includes a first substrate, a first electrode, and a first insulating film. The first electrode and the first insulating film are provided on the first substrate, the first insulating film is formed with an opening, and the first electrode is provided in the opening; preparing a second circuit component, the second circuit component comprising a second substrate, a second electrode, and a second insulating film, wherein the second electrode and the second insulating film are provided on the second substrate, the second insulating film is formed with an opening, and the second electrode is provided in the opening; and The first circuit component and the second circuit component are heated and pressurized, thereby bonding the first circuit component and the second circuit component such that the first insulating film is bonded to the second insulating film and the first electrode is bonded to the second electrode. At least one of the first substrate or the second substrate is a semiconductor substrate having a circuit surface. When the first substrate is a semiconductor substrate having a circuit surface, the first electrode and the first insulating film are provided on the circuit surface; when the second substrate is a semiconductor substrate having a circuit surface, the second electrode and the second insulating film are provided on the circuit surface. At least one of the first insulating film and the second insulating film is an organic insulating film including a cured product of a curable resin composition including a maleimide compound having a maleimide group and an allyl compound having an allyl group.

2. The method according to claim 1, wherein When the first insulating film is the organic insulating film, the first circuit component is prepared by a method including the steps of forming a resin film containing the curable resin composition on the first substrate and curing the resin film. When the second insulating film is a cured product of the curable resin composition, the second circuit component is prepared by a method including forming a resin film containing the curable resin composition on the second substrate and curing the resin film.

3. The method according to claim 1 or 2, wherein: The first insulating film and the second insulating film are the organic insulating films.

4. A semiconductor device comprising: The first circuit component includes a first substrate, a first electrode, and a first insulating film, wherein: The first electrode and the first insulating film are provided on the first substrate, the first insulating film is formed with an opening, and the first electrode is provided in the opening; and a second circuit component joined to the first circuit component and comprising a second substrate, a second electrode, and a second insulating film, wherein the second electrode and the second insulating film are provided on the second substrate, the second insulating film is formed with an opening, and the second electrode is provided in the opening; The first circuit component and the second circuit component are bonded together in such a manner that the first insulating film and the second insulating film are bonded together and the first electrode and the second electrode are bonded together. At least one of the first substrate or the second substrate is a semiconductor substrate having a circuit surface. When the first substrate is a semiconductor substrate having a circuit surface, the first electrode and the first insulating film are provided on the circuit surface; when the second substrate is a semiconductor substrate having a circuit surface, the second electrode and the second insulating film are provided on the circuit surface. At least one of the first insulating film and the second insulating film is an organic insulating film including a cured product of a curable resin composition including a maleimide compound having a maleimide group and an allyl compound having an allyl group.

5. The semiconductor device according to claim 4, wherein The first insulating film and the second insulating film are the organic insulating films. 6 . A curable resin composition comprising a maleimide compound having a maleimide group and an allyl compound having an allyl group, the composition being used for forming an organic insulating film in the method according to claim 1 .

Images