Method for manufacturing semiconductor device, and curable resin composition

Abstract

This method for manufacturing a semiconductor device involves: forming a preliminary pressure-bonded body by thermo-pressure-bonding a second circuit member having a second insulating film to a first circuit member having a second insulating film by means of a preliminary pressure-bonding head; and forming a bonded body in which the first insulating film and the second insulating film are bonded by pressurizing the preliminary pressure-bonded body while heating. At least one among the first insulating film and the second insulating film is an organic insulating film. The plurality of second circuit members are sequentially thermo-pressure-bonded to the first circuit member by means of the preliminary pressure-bonding head while maintaining the temperature of the preliminary pressure-bonding head within a range of equal to or higher than a predetermined minimum temperature and equal to or lower than the preliminary pressure-bonding temperature.

Description

Method for manufacturing semiconductor device and curable resin composition

[0001] The present disclosure relates to a method for producing a semiconductor device and a curable resin composition for hybrid bonding used therein.

[0002] In the three-dimensional packaging of semiconductor chips, hybrid bonding technology, which bonds electrodes and insulating films, has been considered for miniaturizing wiring. It has also been proposed to form the insulating film for hybrid bonding technology using a resin material such as polyimide (Patent Document 1).

[0003] On the other hand, it is known that compositions containing maleimide compounds and allyl compounds are thermally cured by addition reactions including ene reactions and Diels-Alder reactions or radical polymerization (Non-Patent Document 1).

[0004] International Publication No. 2020 / 085183

[0005] Handbook of Thermoset Plastics, Third Edition, 2014, p. 459-510

[0006] The present disclosure relates to the efficient manufacture of large numbers of semiconductor devices having semiconductor substrates joined to other circuit components by hybrid bonding.

[0007] The present disclosure includes the following: [1] Preparing a first circuit member having 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 forms an opening, and the first electrode is provided within the opening; Preparing a second circuit member having 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 forms an opening, and the second electrode is provided within the opening; Placing the first circuit member on a stage in an orientation where the first substrate is located on the stage side; Holding the second circuit member in a preliminary compression bonding head in an orientation where the second substrate is in contact with the preliminary compression bonding head; Thermocompression bonding the second circuit member held by the preliminary compression bonding head to the first circuit member on the stage in an orientation where the first electrode and the second electrode face each other, by using the preliminary compression bonding head heated to a preliminary compression temperature of 250°C or less, thereby forming a pre-compression-bonded body having the first circuit member and the second circuit member; and applying pressure to the pre-bonded body while heating it to a bonding temperature equal to or higher than the pre-bonding temperature to form a bonded body having the first circuit member and the second circuit member, wherein 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, and 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 or the second insulating film is an organic insulating film; and while maintaining the temperature of the pre-bonding head within a range equal to or higher than a predetermined minimum temperature and equal to or lower than the pre-bonding temperature, a plurality of the second circuit members are sequentially thermocompression-bonded to the first circuit member by the pre-bonding head, and the minimum temperature is 70°C or higher and equal to or lower than the pre-bonding temperature.[2] The method according to [1], wherein the pre-compression bonding temperature is 80°C or higher and 250°C or lower. [3] The method according to [1], wherein the pre-compression bonding temperature is 100°C or higher and 250°C or lower. [4] The method according to [1], wherein the pre-compression bonding temperature is 100°C or higher and 220°C or lower. [5] The method according to any one of [1] to [4], wherein the difference between the pre-compression bonding temperature and the lowest temperature is 20°C or lower. [6] The method according to any one of [1] to [4], wherein the difference between the pre-compression bonding temperature and the lowest temperature is 10°C or lower. [7] The method according to any one of [1] to [6], wherein the bonding temperature is 200°C or higher and 350°C or lower. [8] The method according to any one of [1] to [7], wherein the organic insulating film comprises a resin containing an imide group. [9] The method according to [8], wherein the organic insulating film comprises a cured product of a curable resin composition containing a maleimide compound having a maleimide group and an allyl compound having an allyl group.

[10] The method according to [8], wherein the resin containing an imide group is a polyimide resin, a polyamideimide resin, a bismaleimide resin, or a combination thereof.

[11] The method according to [8], wherein the resin containing an imide group is a resin having a structural unit containing an imide group and a polysiloxane bonded to the structural unit.

[12] The method according to any one of [1] to [7], wherein the organic insulating film comprises a cured product of a curable resin composition containing an epoxy resin.

[13] The method according to any one of [1] to [7], wherein the organic insulating film comprises a polybenzoxazole resin.

[14] The method according to any one of [1] to [7], wherein the organic insulating film comprises a benzocyclobutene resin.

[15] A curable resin composition used to form the organic insulating film according to any one of [1] to [7], comprising a maleimide compound having a maleimide group and an allyl compound having an allyl group.

[0008] Hybrid bonding allows for the efficient manufacture of large numbers of semiconductor devices having semiconductor substrates joined to other circuit components.

[0009] FIG. 1 is a process diagram showing an example of a method for manufacturing a semiconductor device. FIG. 2 is a process diagram showing an example of a method for manufacturing a semiconductor device. FIG. 3 is a process diagram showing an example of a method for manufacturing a semiconductor device. FIG. 4 is a process diagram showing an example of a method for manufacturing a semiconductor device. FIG. 5 is a process diagram showing an example of a method for manufacturing a semiconductor device. FIG. 6 is a graph showing an example of a temperature profile of a preliminary compression bonding head in a step of forming a preliminary compression bonded body. FIG. 7 is a graph showing an example of a temperature profile of a preliminary compression bonding head in a step of forming a preliminary compression bonded body.

[0010] The present invention is not limited to the following examples.

[0011] 1 to 6 are process diagrams showing an example of a method for manufacturing a semiconductor device. The method shown in Figures 1 to 6 includes the steps of preparing a first circuit member 10 having a first substrate 11, a first electrode 12, and a first insulating film 13, preparing a second circuit member 20A having a second substrate 21A, a second electrode 22, and a second insulating film 23, arranging the first circuit member 10 on a stage 60 with the first substrate 11 facing the stage 6, holding the second circuit member 20A on a preliminary compression bonding head 65 with the second substrate 21A in contact with the preliminary compression bonding head 65, and The method includes thermocompression bonding the second circuit member 20A to the first circuit member 10 on the stage 60, with the first electrode 12 and the second electrode 22 facing each other, by a precompression bonding head 65 heated to a predetermined precompression temperature as its maximum temperature, thereby forming a precompression-bonded body 30 having the first circuit member 10 and the second circuit member 20A, and forming a bonded body 35 having the first circuit member 10 and the second circuit member 20A by pressing the precompression-bonded body 30 while heating it to a bonding temperature equal to or higher than the precompression temperature. The first circuit member 10 of the bonded body 35 is divided on a dicing tape 80 to form a semiconductor device 35A that is a bonded body of the individualized first circuit member 10A and the second circuit member 20A.

[0012] The first insulating film 13 and the second insulating film 23 can be organic insulating films or inorganic insulating films applicable to hybrid bonding. At least one of the first insulating film 13 and the second insulating film 23 is an organic insulating film. Details of the organic insulating film will be described later. At least one of the first substrate 11A and the second substrate 21A is a semiconductor substrate (e.g., a silicon substrate) having a circuit surface on which an integrated circuit is provided. The first circuit member 10A or the second circuit member 20A having the first substrate 11A or the second substrate 21A that is not a semiconductor substrate may be, for example, an organic interposer.

[0013] The second circuit member 20A is prepared by a method including, for example, providing a plurality of second electrodes 22 on one main surface of an original substrate 21 including portions corresponding to a plurality of second substrates 21A, as shown in FIG. 1A; forming a second insulating film 23 covering the second electrodes 22 on the original substrate 21, as shown in FIG. 1B; removing a portion of the second insulating film 23 from the side opposite the original substrate 21 to expose the second electrodes 22, as shown in FIG. 1C; and dividing the original substrate 21 together with the second insulating film 23 on a dicing tape 40, as shown in FIG. 2, to form a plurality of second circuit members 20A each having an individualized second substrate 21A. The original substrate 21 may be a semiconductor wafer, and the second substrates 21A may be individualized semiconductor substrates (chips). The method for removing the portion of the second insulating film 23 may be, for example, chemical mechanical polishing (CMP). In the second circuit member 20A, the second insulating film 23 forms a plurality of openings 23a that are through holes exposing the second substrate 21A, and the first electrodes 12 are provided in the openings 23a. The second electrodes 22 and the second insulating film 23 may form a flat surface. Convex or concave portions may be formed at the positions of the second electrodes 22. When the second substrate 21A is a semiconductor substrate having a circuit surface, the second electrodes 22 and the second insulating film 23 are typically provided on the circuit surface. The original substrate 21 can be divided by ordinary dicing.

[0014] The original substrate 21 (particularly a semiconductor wafer) may be disk-shaped. In this case, the diameter of the original substrate 21 may be 150 mm or more and 300 mm or less. The thickness of the original substrate 21 may be 40 μm or more and 1000 μm or less.

[0015] As shown in FIG. 3A, a plurality of second circuit members 20A formed on the dicing tape 40 are sequentially picked up by a pickup tool 50. The second circuit members 20A are adsorbed to the pickup tool 50 with the second electrodes 22 and the second insulating films 23 facing the pickup tool 50. The picked-up second circuit members 20A are transferred from the pickup tool 50 to a preliminary compression bonding head 65 as shown in FIG. 3B. The preliminary compression bonding head 65 holds the second circuit members 20A with the second substrate 21A facing the preliminary compression bonding head 65. The second circuit members 20A may be adsorbed to the preliminary compression bonding head 65. The preliminary compression bonding head 65 may be, for example, the head of a conventional flip-chip bonder.

[0016] As shown in (a) of FIG. 4, the second circuit member 20A held by the preliminary crimping head 65 is aligned directly above the first circuit member 10A arranged on the stage 60 so that the first electrode 12 and second electrode 22 to be joined face to face.

[0017] The first circuit member 10 includes portions corresponding to the plurality of circuit members after singulation. Therefore, a first electrode 12 and a first insulating film 13 constituting the plurality of circuit members are provided on a single first substrate 11. The first insulating film 13 forms a plurality of openings 13a, which are through-holes through which the first substrate 11 is exposed, and the first electrodes 12 are provided in the openings 13a. The first circuit member 10 can be prepared by a method similar to the method illustrated in FIG. 1 , except that the first substrate 11 is not divided. The first substrate 11 of the prepared first circuit member 10 may be a semiconductor wafer having a circuit surface. In this case, the first electrode 12 and the first insulating film 13 are typically provided on the circuit surface. In this example, the first circuit member before singulation and the singulated second circuit member are bonded. The method disclosed herein may be used to bond singulated circuit members together, or to bond circuit members before singulation together.

[0018] The shapes of the first electrode 12 and the second electrode 22 are not particularly limited, but some or all of these electrodes are arranged so that the first electrode 12 and the second electrode 22 face each other and are bonded to each other. The widths of the first electrode 12 and the second electrode 22 may be, for example, 1 μm or more or 100 μm or more, and 300 μm or less or 30 μm or less. Here, width 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 21A. The spacing between adjacent first electrodes 12 and adjacent second electrodes 22 may be, for example, 1 μm or more or 100 μm or more, and 300 μm or less or 30 μm or less. The heights of the first electrodes 12 and the second electrodes 22 may be, for example, 1 μm or more or 10 μm or more, and 100 μm or less or 10 μm or less. The height of the first electrode 12 may be the same as or different from the thickness of the first insulating film 13. The height of the second electrode 22 may be the same as or different from the thickness of the second insulating film 23 .

[0019] The first electrode 12 and the second electrode 22 are formed from 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 plating.

[0020] 4(b), the second circuit member 20A is thermocompression bonded to the first circuit member 10 by a preliminary compression bonding head 65. This thermocompression bonding forms a preliminary compression body 30 in which the first circuit member 10 and the second circuit member 20A are preliminarily bonded. During the thermocompression bonding, the second circuit member 20A is heated by heat conduction from the heated preliminary compression bonding head 65 and is pressed by the preliminary compression bonding head 65. As shown in FIGS. 4 and 5, a plurality of second circuit members 20A are sequentially thermocompression bonded to the first circuit member 10 by one preliminary compression bonding head. At the stage of the preliminary compression body 30, mainly the first insulating film 13 and the second insulating film 23 are bonded to some extent.

[0021] Before the second circuit member 20A is thermocompression bonded to the first circuit member 10, the first insulating film 13, the second insulating film 23, or both may be irradiated with ultraviolet light.

[0022] While a plurality of second circuit members 20A are sequentially thermocompression-bonded, i.e., while the pre-compression head 65 holds the second circuit member 20A, aligns the second circuit member 20A on the first circuit member 10, and then repeatedly thermocompresses the second circuit member 20A to the first circuit member 10, the temperature of the pre-compression head 65 is maintained within a range of not less than a predetermined minimum temperature and not more than a pre-compression temperature. The temperature of the stage 60 may also be maintained within a range of not less than a predetermined minimum temperature and not more than a pre-compression temperature.

[0023] 7 and 8 are graphs showing an example of a temperature profile of the pre-compression bonding head 65 while a plurality of second circuit members 20A are sequentially thermocompression bonded to the first circuit member 10. The graphs show the relationship between the temperature of the pre-compression bonding head 65 and time. １Ｓ From time t １Ｅ During time t ２Ｓ From time t ２Ｅ During time t ３Ｓ From time t ３Ｅ and time t ４Ｓ From time t ４Ｅ During this time, the second circuit member 20A is pressed against the first circuit member 10 by the pre-pressing head 65. First, the temperature of the pre-pressing head 65° C. is set to the initial temperature T ０From the predetermined preliminary pressure bonding temperature T １ In the example of FIGS. 7 and 8, the time t １Ｓ Before this, the temperature of the pre-compression bonding head 65 is raised to the pre-compression temperature T １ The temperature of the pre-compression bonding head 65 reaches a temperature during the thermal compression bonding of the second circuit member 20A, that is, during the time t １Ｓ From time t １Ｅ The temperature may reach the preliminary compression bonding temperature T1 at any time during the period. １ is the maximum temperature of the pre-compression bonding head 65 while the holding and thermocompression bonding of a plurality of second circuit members 20A are repeated. When the first second circuit member 20A is held by the pre-compression bonding head 65, the temperature of the pre-compression bonding head 65 reaches the minimum temperature T ｍｉｎ an initial temperature T ０ and at temperature T ０ to preliminary bonding temperature T １ The temperature may be any temperature between

[0024] In the example of FIG. 7, the temperature of the pre-compression bonding head 65 is the pre-compression temperature T １ After the temperature reaches the preliminary compression temperature T １ That is, the preliminary compression temperature T １ However, the lowest temperature T ｍｉｎ Even in this case, the temperature of the pre-compression bonding head 65 may be lower than the desired pre-compression temperature T １ For example, if the temperature of the pre-compression head 65 is equal to or higher than the pre-compression temperature T １ It may be maintained within a range of ±2°C.

[0025] In the example of FIG. 8, the temperature of the pre-compression bonding head 65 is the pre-compression temperature T １ After reaching the minimum temperature T ｍｉｎ The preliminary compression temperature T １ In the example of FIG. 8, the temperature of the pre-compression bonding head 65 is maintained within the following range during the thermal compression bonding of one second circuit member 20A (for example, the time t １Ｓ From time t１Ｅ At any point during the period from １ After the completion of the thermocompression bonding of one second circuit member 20A, the temperature starts to decrease from the lowest temperature T ｍｉｎ When the temperature of the pre-compression bonding head 65 reaches the lowest temperature T ｍｉｎ At any time before or after the pre-pressing head 65 reaches the second circuit member 20A, the pre-pressing head 65 holds the second circuit member 20A to be next heat-pressed.

[0026] The temperature of the preliminary compression bonding head 65 is the lowest temperature T ｍｉｎ If the temperature is maintained at a high temperature of 1000 K or more, the time required for heating and cooling the pre-compression bonding head 65 can be shortened. If the process time is shortened, the thermal history that the first circuit member 10 is subjected to while a large number of second circuit members 20A are thermocompression bonded to one first circuit member 10 is reduced. If the thermal history that the first circuit member 10 is subjected to is reduced, deterioration due to oxidation of the first electrode 12, etc., can be suppressed. The second insulating film 23 used in hybrid bonding tends to maintain low fluidity even at high temperatures, so is less susceptible to the effects of temperature even when the second circuit member 20A is held by the pre-compression bonding head 65 maintained at a high temperature. Pre-compression bonding temperature T １ The minimum temperature T may be, for example, 80°C or higher, 90°C or higher, 100°C or higher, 110°C or higher, 120°C or higher, or 130°C or higher, or may be 250°C or lower, 240°C or lower, 230°C or lower, 220°C or lower, 210°C or lower, 200°C or lower, 190°C or lower, 180°C or lower, 170°C or lower, 160°C or lower, 150°C or lower, or 140°C or lower. ｍｉｎ is usually 70°C or higher, and the preliminary pressure bonding temperature T １ The minimum temperature T ｍｉｎ The temperature may be 80°C or higher, or 250°C or lower.

[0027] Preliminary bonding temperature T １ and the minimum temperature T ｍｉｎ If the difference between the temperature T １ and the minimum temperature T ｍｉｎ The difference may be 20°C or less, or 10°C or less.

[0028] After the pre-compressed body 30 having one first circuit member 10 and a plurality of second circuit members 20A is formed, the pre-compressed body 30 is heated to a pre-compression temperature T １ The pre-bonded body 30 is pressed while being heated to the above bonding temperature. In the example of FIG. 5 , the pre-bonded body 30 is placed on a stage 70, and a plurality of second circuit members 20A are pressed collectively against the first circuit member 10 by a pressing member 71. The pre-bonded body 30 is heated to the bonding temperature by the stage 70, the pressing member 71, or both. This heating and pressing forms a bonded body 35 having one first circuit member 10 and a plurality of second circuit members 20A, as shown in FIG. 6( a) . Heating and pressing at the bonding temperature primarily bonds the first electrode 12 and the second electrode 22 together by material bonding, and can further strengthen the bond between the first insulating film 13 and the second insulating film 23.

[0029] The bonding temperature can be a temperature at which the first electrode 12 and the second electrode 22 are electrically connected by a material bond, and is usually set to a pre-compression temperature T １ The temperature is equal to or higher than 200° C. For example, the bonding temperature may be 200° C. or higher and 350° C. or lower. The pressure for forming the bonded body 35 may be 1.0 MPa or higher and 5.0 MPa or lower. The heating and pressurizing time for forming the bonded body 35 may be, for example, 10 seconds or longer and 2 hours or shorter. The method of heating and pressurizing for forming the bonded body 35 is not limited to heat pressing using a pressing member, and may be, for example, heating in a pressurized atmosphere.

[0030] 6(b), the first circuit member 10 of the formed bonded body 35 is singulated into a plurality of first circuit members 10A on the dicing tape 80. This forms a plurality of semiconductor devices 35A (bonded bodies) each having the singulated first circuit members 10A and second circuit members 20A. A normal dicing method can be used as the dividing method for singulating the first circuit members 10.

[0031] Organic Insulating Film The first insulating film 13, the second insulating film 23, or both of them may be an organic insulating film that can be bonded to other insulating films by application of heat and pressure.

[0032] The organic insulating film may contain a resin containing an imide group. For example, an organic insulating film containing a cured product of a curable resin composition (hereinafter also referred to as a "curable maleimide resin composition") containing a maleimide compound having a maleimide group and an allyl compound having an allyl group contains a resin containing an imide group derived from the maleimide compound. An organic insulating film containing a cured product of the curable maleimide resin composition can be well bonded to other insulating films by heating and pressurization. The surface of an organic insulating film containing a cured product of the curable maleimide resin composition may contain many maleimide groups, allyl groups, or functional groups derived therefrom. Therefore, the organic insulating film may exhibit good bonding properties without necessarily requiring an activation treatment such as plasma treatment. In addition, the polishing rate of the organic insulating film may be adjustable based on the crosslink density of the cured product. Both the first insulating film 13 and the second insulating film 23 may be organic insulating films containing a cured product of the curable maleimide resin composition.

[0033] The maleimide compound is a compound having one or more maleimide groups. From the viewpoints of heat resistance and a reduced thermal expansion coefficient of the cured product, the curable maleimide resin composition may contain a maleimide compound having two or more maleimide groups.

[0034] The maleimide compound may have an imide group containing a nitrogen atom directly bonded to a cyclic group (e.g., an aromatic group). For example, the maleimide compound in the curable maleimide resin composition may be represented by the following formula (Ia) or (Ib): The compound may contain a compound represented by the following formula:

[0035] 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 may each independently be an aromatic group (e.g., a phenylene group). １may be a group containing one or more cyclic groups (excluding a maleimide group) selected from a monocyclic ring, a fused ring, a non-fused bridged ring, and a spiro ring, which may have a substituent, a linear alkylene group (e.g., a methylene group or a propane-1,3-diyl group) which may have a substituent, a propane-2,2-diyl group which may have a substituent, or a single bond. １ may have two or more cyclic groups and a single bond or a divalent organic group (for example, an optionally substituted methylene group, or an optionally substituted propane-2,2-diyl group) connecting the two or more cyclic groups. １ is a cyclic group and Q １ or Q ２ and may further have a methylene group connecting L １ The cyclic group in L may be substituted with, for example, a methyl group or a maleimide group. １ may have a cyclic group formed by removing one or more hydrogen atoms from benzene, 2,3-dihydro-1H-indene, or succinimide.

[0036] In formula (Ib), Q ３ represents a cyclic group which may have a substituent. ３ may be an aromatic group (e.g., a phenylene group). ３ The cyclic group therein may be substituted, for example, with a methyl group or a maleimide group.

[0037] Specific examples of the maleimide compound include compounds represented by the following formulas 11, 12, 13, and 14: In these formulas, n represents an integer of 1 or more.

[0038]

[0039] Examples of commercially available maleimide compounds include NE-X-9470S (trade name, DIC), MIR-3000-70MT (trade name, Nippon Kayaku), BMI-2300 (trade name, Yamato Chemical Industries), BMI-5100 (trade name, Yamato Chemical Industries), BMI-80 (trade name, Yamato Chemical Industries), BMI (trade name, Yamato Chemical Industries), and SFR-2300MR-T (trade name, Resonac).

[0040] Allyl compounds contain one or more allyl groups (2-propenyl groups, -CH ２ CH=CH ２ From the viewpoints of improving the heat resistance and reducing the thermal expansion coefficient of the cured product, the curable maleimide resin composition may contain an allyl compound having two or more allyl groups.

[0041] 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 be a compound represented by the following formula (IIa), (IIb), (IIc), or (IId): The compound may contain a compound represented by the following formula:

[0042] In formulas (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 may each independently be a group in which one or more hydrogen atoms have been removed from benzene, isocyanuric acid, or nadimide. ２ may be a group containing one or more cyclic groups (excluding a maleimide group) selected from a monocyclic ring, a fused ring, a non-fused bridged ring, and a spiro ring, which may have a substituent, a linear alkylene group (e.g., a methylene group or a propane-1,3-diyl group) which may have a substituent, a propane-2,2-diyl group which may have a substituent, or a single bond. ２ may have two or more cyclic groups and a single bond or a divalent organic group (for example, an optionally substituted methylene group, or an optionally substituted propane-2,2-diyl group) connecting the two or more cyclic groups. ２ is a cyclic group and Q ４ or Q ５ and may further have a methylene group connecting L ２ The cyclic group in L may be substituted with a substituent selected from, for example, a methyl group, a hydroxy group, and an allyl group. ２ may have a phenylene group which may have a substituent.

[0043] In formulas (IIc) and (IId), Q ６ represents a cyclic group which may have a substituent. ６ may be an aromatic group (e.g., a phenylene group) or a group in which one or more hydrogen atoms have been removed from isocyanuric acid. ３ The cyclic groups therein may be substituted, for example, with methyl or allyl groups.

[0044] Specific examples of the allyl compound include compounds represented by the following formulas 21, 22, 23, 24, 25, 26, 27, 28, and 29. In these formulas, n represents an integer of 1 or more.

[0045] Examples of commercially available allyl compounds include DABPA (trade name, Kanto Chemical), DA-BPF (trade name, Yokkaichi Chemical Industry), LVA01 (trade name, Gun-ei Chemical Industry), BPA-AE (trade name, Konishi Chemical Industry), BANI-X (trade name, Maruzen Petrochemical Industry), BANI-M (trade name, Maruzen Petrochemical Industry), FATC-809 (trade name, Gun-ei Chemical Industry), FATC-809AP (trade name, Gun-ei Chemical Industry), DAIC (trade name, Shikoku Chemical Industry), and DD-1 (trade name, Shikoku Chemical Industry).

[0046] 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 more, based on the total amount of the maleimide compound and the allyl compound, and may be 65% by mass or less, 60% by mass or less, or 55% by mass or less.

[0047] The curable maleimide resin composition may further comprise a component that initiates or accelerates the reaction of the maleimide compound and the allyl compound.

[0048] The curable maleimide resin composition may further contain a component that reduces the dielectric tangent of the cured product (hereinafter referred to as a "dielectric tangent adjuster"). The dielectric tangent adjuster may be, for example, a compound represented by the following formula (IIIa), (IIIb), or (IIIc): The aromatic compounds include those represented by the formula:

[0049] In formula (IIIa), R １１ , R １４ and R １５ each independently represents a hydrogen atom, a methyl group, or a t-butyl group; R １２ and R １３ each independently represents a hydrogen atom, a hydroxy group, or an organic group having 1 to 30 carbon atoms; Z １ 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.

[0050] 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 t-butyl group; R １７ , R １８ , R ２３ and R ２４ each independently represents a hydrogen atom, a hydroxy group, or an organic group having 1 to 30 carbon atoms; Z ２ represents a divalent organic group having 1 to 50 carbon atoms containing at least one heteroatom selected from the group consisting of sulfur, phosphorus, oxygen, and nitrogen, or a divalent organic group having 1 to 75 carbon atoms.

[0051] 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 t-butyl group; R ２７ , R ２８ , R ３２ , R３３ , R ３８ and R ３９ each independently represents a hydrogen atom, a hydroxyl group, or an organic group having 1 to 30 carbon atoms; Z ３ represents a trivalent organic group having 1 to 50 carbon atoms 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.

[0052] The content of the dielectric loss tangent adjuster may 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 adjuster may be 2% by mass or more or 5% by mass or more, based on the total amount of the maleimide compound and the allyl compound, and may be 50% by mass or less or 40% by mass or less.

[0053] The curable maleimide resin composition may further contain a solvent to dissolve or disperse 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.

[0054] The curable maleimide resin composition may further include an adhesion promoter, such as a silane coupling agent, an aluminum-based adhesion promoter, or a combination thereof.

[0055] Examples of the silane coupling agent include γ-aminopropyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-mercaptopropylmethyldimethoxysilane, 3-methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinopropylsilane, diethoxy-3-glycidoxypropylmethylsilane, N-( 3-diethoxymethylsilylpropyl)succinimide, N-[3-(triethoxysilyl)propyl]phthalamic acid, benzophenone-3,3'-bis(N-[3-triethoxysilyl]propylamido)-4,4'-dicarboxylic acid, benzene-1,4-bis(N-[3-triethoxysilyl]propylamido)-2,5-dicarboxylic acid, 3-(triethoxysilyl)propyl succinic anhydride, and N-phenylaminopropyltrimethoxysilane.

[0056] Examples of aluminum-based adhesion promoters include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] The curable maleimide resin composition may further comprise 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-t-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]phenyl ...

[0033] benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-benzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-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.

[0061] The content of the azole compound may be 0.1% by mass or more and 20% by mass or less, or 0.5% by mass or more and 5% by mass or less, based on the total amount of the maleimide compound and the allyl compound.

[0062] The curable maleimide resin composition may contain a hindered phenol compound. Examples of the hindered phenol compound include 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-butyl-hydroquinone, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, isooctyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 4,4'-methylenebis(2,6-di-t-butylphenol), 4,4'-thio-bis(3-methyl-6-t-butylphenol), and 4,4'-butylidene-bis(3-methyl-6-t-butylphenol). 1,6-hexanediol bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), 2,2'-methylene-bis(4-methyl-6-t-butylphenol), 2,2 '-Methylene-bis(4-ethyl-6-t-butylphenol), pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris(3-hydroxy-2,6-dimethyl-4-isopropylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5 H)-trione, 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-s-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-t-butyl-3-hydroxy-2,5,6-trimethylbenzyl)-1,3 ,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-t-butyl-5-ethyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-t-butyl-6-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5 -tris(4-t-butyl-6-ethyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-t-butyl-5,6-diethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-t-butyl-3-hydroxy-2-methylbenzyl)- Examples include 1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-t-butyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, and 1,3,5-tris(4-t-butyl-5-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione.

[0063] The content of the hindered phenol compound may be 0.1% by mass or more and 20% by mass or less, or 0.5% by mass or more and 10% by mass or less, based on the total amount of the maleimide compound and the allyl compound.

[0064] The curable maleimide resin composition may contain an organotitanium compound, such as a titanium chelate compound having two or more alkoxy groups, a tetraalkoxytitanium compound, a titanocene compound, a monoalkoxytitanium compound, a titanium oxide compound, a titanium tetraacetylacetonate compound, a titanate coupling agent, or a combination thereof.

[0065] Examples of titanium chelate compounds having two or more alkoxy groups include titanium bis(triethanolamine) diisopropoxide, titanium di(n-butoxide) bis(2,4-pentanedionate), titanium diisopropoxide bis(2,4-pentanedionate), titanium diisopropoxide bis(tetramethylheptanedionate), and titanium diisopropoxide bis(ethylacetoacetate).

[0066] Examples of tetraalkoxytitanium compounds include titanium tetra(n-butoxide), titanium tetraethoxide, titanium tetra(2-ethylhexoxide), titanium tetraisobutoxide, titanium tetraisopropoxide, titanium tetramethoxide, titanium tetramethoxypropoxide, titanium tetramethylphenoxide, titanium tetra(n-nonyloxide), titanium tetra(n-propoxide), titanium tetrastearyloxide, and titanium tetrakis[bis{2,2-(allyloxymethyl)butoxide}].

[0067] Examples of titanocene compounds include pentamethylcyclopentadienyltitanium trimethoxide, 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.

[0068] Examples of monoalkoxytitanium compounds include titanium tris(dioctylphosphate) isopropoxide and titanium tris(dodecylbenzenesulfonate) isopropoxide.

[0069] Examples of titanium oxide compounds include titanium oxide bis(pentanedionate), titanium oxide bis(tetramethylheptanedionate), and phthalocyanine titanium oxide.

[0070] An example of a titanium tetraacetylacetonate compound is titanium tetraacetylacetonate.

[0071] An example of a titanate coupling agent is isopropyl tridodecylbenzenesulfonyl titanate.

[0072] The content of the organotitanium 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.

[0073] The organic insulating film containing the cured product of the curable maleimide resin composition is formed by a method including, for example, applying a solvent-containing curable maleimide resin composition to the original substrate 21 or the first substrate before singulation, removing the solvent from the applied film of the curable maleimide resin composition as necessary to form a resin film, and curing the resin film by heating to form an organic insulating film containing the cured product of the curable maleimide resin composition. The heating temperature for removing the solvent may be, for example, 60°C or higher and 150°C or lower. Heating the resin film promotes curing reactions such as an ene reaction between maleimide groups and allyl groups, a Diels-Alder reaction involving the addition of maleimide groups, and radical polymerization, to form a cured product. Since the curing reaction proceeds primarily via an addition reaction, volatile components resulting from elimination are less likely to be generated. Furthermore, since the curing reaction proceeds at a relatively low temperature, thermal damage to the semiconductor substrate or the like can be reduced. The heating temperature for curing the resin film may be, for example, 170°C or higher and 260°C or lower. The heating time for curing the resin film may be, for example, 60 minutes or more and 180 minutes or less.

[0074] Other examples of resins containing imide groups that can be contained in the organic insulating film include polyimide resins, polyamideimide resins, and bismaleimide resins. The polyimide resin can be, for example, a polymer containing a structural unit (imide unit) represented by the following formula (1A). The polyamideimide resin can be a polymer containing a structural unit (imide unit) represented by the following formula (1B) or (1C). Alternatively, the resin containing imide groups may be a resin having an imide unit represented by formula (1A), (1B), or (1C) and a linear, branched, or cage-shaped polysiloxane bonded to the imide unit.

[0075]

[0076] In formulas (1A) to (1C), R １ represents a tetravalent organic group, and R ２ represents a trivalent organic group, and R １０ teeth ２ represents a 2-valent organic group, and * represents a bond.

[0077] R １ can be a group containing an aromatic group, for example, R １ may be a group obtained by removing four hydrogen atoms from a compound represented by the following formula (11), (12), or (13): ２ can be a group containing an aromatic group, for example, R ２ Alternatively, it may be a group obtained by removing three hydrogen atoms from a compound represented by the following formula (11), (12), or (13): In formula (13), X represents a direct bond, a methanediyl group, a propane-2,2-diyl group, a 1,1,1,3,3,3-hexafluoropropane-2,2-diyl group, a carbonyl group, a sulfonyl group, a thio group, a carbonyloxy group, an oxy group, a fluorene-9,9-diyl group, or an amide group.

[0078]

[0079] R in formulas (1A) to (1C) １０may be an optionally substituted alkylene group, a group containing an optionally substituted aromatic group, a group containing an optionally substituted cycloaliphatic group, or a group containing a combination thereof. The aromatic group may be a group obtained by removing two hydrogen atoms from a compound represented by formula (11), (12), or (13).

[0080] An organic insulating film containing a resin containing imide groups can be formed, for example, by a method including applying a resin varnish containing a resin precursor onto a first semiconductor substrate or a second semiconductor substrate and heating the coating to form an organic insulating film containing a resin containing imide groups. When forming an organic insulating film containing a polymer containing imide units (polyimide resin or polyamideimide resin), the resin precursor can be a polyamic acid having structural units corresponding to the imide units. A curing reaction, including an imidization reaction, occurs upon heating the coating, thereby forming an organic insulating film containing a polyimide resin or a polyamideimide resin. When forming an organic insulating film containing a resin containing a polysiloxane bonded to imide units, the resin precursor can include a combination of a polycarboxylic acid compound corresponding to the imide units and a polysiloxane substituted with a substituent having an amino group. The polycarboxylic acid compound may include an anhydride or a carboxylic acid ester. An organic insulating film containing a resin containing imide groups is formed by a reaction between the amino group of the substituent bonded to the polysiloxane and the polycarboxylic acid compound, followed by a curing reaction, including an imidization reaction.

[0081] The organic insulating film may contain a cured product of a curable resin composition (curable epoxy resin composition) containing an epoxy resin. The curable epoxy resin composition may contain optional components such as a curing agent in addition to an epoxy resin, which is a compound having two or more epoxy groups. The organic insulating film containing a cured product of the curable epoxy resin composition can be formed using a curable epoxy resin composition containing a solvent in the same manner as the organic insulating film containing a cured product of a curable maleimide resin composition.

[0082] The organic insulating film may include a polybenzoxazole resin, a benzocyclobutene resin, or a combination thereof.

[0083] The organic insulating film containing a polybenzoxazole resin can be formed, for example, by a method including: applying a resin varnish containing a resin precursor onto a first semiconductor substrate or a second semiconductor substrate; and heating the coating to cause a curing reaction, including a reaction to form benzoxazole groups, to form an insulating resin film containing a polybenzoxazole resin.

[0084] Verification Example (1) Preparation of Curable Resin Composition The following maleimide compounds and allyl compounds were prepared. Maleimide compounds: Phenylmethane maleimide (compound of formula 13, BMI-2300, Daiwa Chemical Industry Co., Ltd.) 4,4'-diphenylmethane bismaleimide (compound of formula 14, BMI, Daiwa Chemical Industry Co., Ltd.) Allyl compounds: Arylphenol resin (compound of formula 23, LVA01, Gunei Chemical Industry Co., Ltd.) 2,2'-diallyl bisphenol A (DABPA, Kanto Chemical Co., Ltd.) Compound of formula 25 (BATE, synthesized according to a conventional method) Bisallylnadimide (compound of formula 29, BANI-M, Maruzen Petrochemical Co., Ltd.)

[0085] (2) Evaluation of Thermal Properties of Organic Insulating Film A maleimide compound and an allyl compound in the compounding ratio (parts by mass) shown in Table 1 were mixed while being melted by heating to prepare a resin composition. 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, at 200°C for 30 minutes, and at 250°C for 1 hour, in that order. 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.

[0086] Glass Transition Temperature (Tg) The Tg of the organic insulating film was measured by dynamic mechanical analysis (DMA) under the following conditions: The temperature at which Tan δ showed a maximum value was recorded as Tg. Frequency: 10 Hz; Heating rate: 5°C / min

[0087] Coefficient of Linear Thermal Expansion (CTE) The coefficient of linear thermal expansion (CTE) of the organic insulating film was measured by the TMA method. The CTE was determined in the temperature range of 50°C to 100°C. The measurement results are shown in Table 1.

[0088]

[0089] (4) Bonding Test Test #1-1 The curable resin composition of Example 2 was applied to a silicon wafer using a spin coater. The coating was heated at 175°C for 1 hour in a nitrogen atmosphere to form an organic insulating film (10 μm thick) containing a cured product of the curable resin composition. The organic insulating film formed on the silicon wafer was polished by CMP. The silicon wafer was then diced into individual pieces together with the organic insulating film using a blade dicing tool to obtain a lower test piece having an 8 mm x 8 mm chip and an organic insulating film, and an upper test piece having a 4 mm x 4 mm chip and an organic insulating film. The lower test piece was placed on the stage with the organic insulating film facing upward. The upper test piece, held by the preliminary bonding head with the chip in contact with the preliminary bonding head, was thermocompression-bonded to the lower test piece on the stage for 10 seconds using the preliminary bonding head so that the organic insulating films were in contact with each other. During thermocompression bonding, the pressure applied to the upper test piece by the preliminary bonding head was 0.5 MPa. The temperature of the pre-bonding head was maintained at 130°C from the start of holding the upper test piece until the end of thermocompression bonding. The pre-bonded body was heated and pressed at a pressure of 2.5 MPa for 5 minutes using a hot press set at a temperature of 250°C to obtain a bonded body for evaluation. A total of three bonded bodies for evaluation were produced under similar conditions.

[0090] Tests #2-1 and #3-1 Bonded bodies for evaluation were prepared under the same conditions as in Test #1-1, except that the temperature of the pre-bonding head was maintained at 150°C or 200°C from the start of holding the upper test piece until the end of thermocompression bonding.

[0091] Tests #1-2, #2-2, #2-3 The temperature of the preliminary compression bonding head was set to 50°C from the time the upper test piece began to be held until the start of thermocompression bonding. From the time the upper test piece and the lower test piece came into contact and thermocompression bonding began, the temperature of the preliminary compression bonding head was raised to 130°C, 150°C, or 200°C over 3 seconds, held at that temperature for 10 seconds, and then lowered to 50°C over 4 seconds. A total of three bonded bodies for evaluation were produced under the same conditions as in Test #1-1 except for the above.

[0092] Shear test: The shear strength at 60°C was measured by a peel test in which stress was applied along the bonding surface of the organic insulating film to a test piece for the upper part of the bonded body. The shear strength of the pre-bonded body obtained under each temperature condition was also measured. The shear strength shown in Table 2 is the average value of the values ​​measured for three bonded bodies or pre-bonded bodies for evaluation.

[0093]

[0094] The evaluation results are shown in Table 2. It was confirmed that a bonded body in which organic insulating films are bonded sufficiently strongly to each other can be efficiently formed under conditions in which the temperature of the pre-bonding head is maintained at a high temperature.

[0095] 10, 10A... First circuit member, 11, 11A... First substrate, 12... First electrode, 13... First insulating film, 13a... Opening, 20A... Second circuit member, 21... Original substrate, 21A... Second substrate, 22... Second electrode, 23... Second insulating film, 23a... Opening, 30... Preliminary pressure-bonded body, 35... Bonded body, 35A... Semiconductor device (bonded body), 40... Dicing tape, 50... Pickup tool, 65... Preliminary pressure-bonding head, 70... Stage, 80... Dicing tape, T ０ ...initial temperature, T １ ...Pre-compression temperature, T ｍｉｎ ...minimum temperature.

Claims

1. Preparing a first circuit member having a first substrate, a first electrode, and a first insulating film, the first electrode and the first insulating film being provided on the first substrate, the first insulating film forming an opening, and the first electrode being provided within the opening; Preparing a second circuit member having a second substrate, a second electrode, and a second insulating film, the second electrode and the second insulating film being provided on the second substrate, the second insulating film forming an opening, and the second electrode being provided within the opening; Arranging the first circuit member on a stage in a direction such that the first substrate is located on the stage side; Holding the second circuit member on a preliminary bonding head in a direction such that the second substrate is in contact with the preliminary bonding head; Thermocompressing the second circuit member held on the preliminary bonding head to the first circuit member on the stage in a direction such that the first electrode and the second electrode face each other, by using the preliminary bonding head heated to a maximum temperature of 250°C or less, thereby forming a pre-compressed body having the first circuit member and the second circuit member; forming a bonded body having the first circuit member and the second circuit member, wherein 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 pre-bonded body to a bonding temperature equal to or higher than the pre-bonding temperature; 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, and 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 or the second insulating film is an organic insulating film; and while maintaining a temperature of the pre-bonding head within a range equal to or higher than a predetermined minimum temperature and equal to or lower than the pre-bonding temperature, a plurality of the second circuit members are sequentially thermocompression-bonded to the first circuit member by the pre-bonding head; and the minimum temperature is a temperature of 70° C. or higher and equal to or lower than the pre-bonding temperature.

2. The method according to claim 1, wherein the pre-pressing temperature is 80°C or higher and 250°C or lower.

3. The method according to claim 1, wherein the pre-pressing temperature is 100°C or higher and 250°C or lower.

4. The method according to claim 1, wherein the pre-pressing temperature is 100°C or higher and 220°C or lower.

5. The method of claim 1, wherein the difference between said pre-compression temperature and said minimum temperature is 20° C. or less.

6. The method of claim 1, wherein the difference between said pre-compression temperature and said minimum temperature is 10° C. or less.

7. The method of claim 1, wherein the bonding temperature is between 200°C and 350°C.

8. The method according to claim 1, wherein the organic insulating film comprises a resin containing an imide group.

9. The method according to claim 8, wherein the organic insulating film comprises a cured product of a curable resin composition containing a maleimide compound having a maleimide group and an allyl compound having an allyl group.

10. The method of claim 8, wherein the resin containing imide groups is a polyimide resin, a polyamideimide resin, a bismaleimide resin, or a combination thereof.

11. The method according to claim 8, wherein the resin containing an imide group is a resin having a structural unit containing an imide group and a polysiloxane bonded to the structural unit.

12. The method according to claim 1, wherein the organic insulating film comprises a cured product of a curable resin composition containing an epoxy resin.

13. The method of claim 1, wherein the organic insulating film comprises a polybenzoxazole resin.

14. The method of claim 1, wherein the organic insulating film comprises a benzocyclobutene resin.

15. A curable resin composition which contains a maleimide compound having a maleimide group and an allyl compound having an allyl group and is used to form an organic insulating film in the method according to claim 1.