Method for polishing resin film and method for manufacturing circuit connection body

Abstract

Provided is a method for polishing a resin film, the method comprising: semi-curing, by heat treatment, a thermosetting resin film containing a maleimide compound with a maleimide group; and polishing the semi-cured resin film by chemical mechanical polishing while supplying an abrasive containing silica particles. Also provided is a method for manufacturing a circuit connection body, the method comprising polishing a resin film.

Description

Method for polishing a resin film and method for manufacturing a circuit connector

[0001] The present disclosure relates to a method for polishing a resin film and a method for manufacturing a circuit connection body.

[0002] In the three-dimensional packaging of semiconductor chips, hybrid bonding, which bonds electrodes and insulating films, has been considered for miniaturization of wiring. It has also been proposed to form the insulating film for hybrid bonding 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] Organic insulating films formed from resin materials are expected to be advantageous compared to inorganic insulating films in terms of reducing the influence of debris, etc. Resin films used as organic insulating films are sometimes formed by methods including a chemical mechanical polishing (CMP) process for planarization, etc. Resin films can generally be polished at an appropriate polishing rate by CMP using an abrasive containing alumina particles as abrasive grains. However, the surface of a resin film polished by CMP using an abrasive containing alumina particles tends to have a large surface roughness.

[0007] The present disclosure relates to a method for polishing a resin film, which can polish a resin film at an appropriate polishing rate and form a surface having sufficiently small surface roughness.

[0008] The present disclosure includes the following: [1] A method for polishing a resin film, comprising: semi-curing a thermosetting resin film containing a maleimide compound having a maleimide group by heat treatment; and polishing the semi-cured resin film by chemical mechanical polishing while supplying an abrasive containing silica particles. [2] A method for polishing a resin film, comprising: semi-curing a thermosetting resin film containing a maleimide compound by heat treatment; and polishing the semi-cured resin film by chemical mechanical polishing while supplying an abrasive containing silica particles. [3] A method for polishing a resin film, wherein the resin film semi-cured by the heat treatment has a curing rate of 90% or less, and the curing rate is expressed by the formula: Cure rate [%] = 100 - (Q １ / Q ０ ) × 100, and Q ０ is the heat generation amount [J / g] due to the curing reaction in the resin film before the heat treatment, and Q １ is the amount of heat generated [J / g] by the curing reaction in the resin film after the heat treatment. [3] The method according to [1] or [2], wherein the resin film before the heat treatment further contains a reactive component that reacts with the maleimide compound. [4] The reactive component contains one or more compounds selected from the group consisting of a styrene-based compound, an allyl compound having an allyl group, a phenolic compound having a phenolic hydroxyl group, and a benzoxazine compound having a benzoxazine group, and the styrene-based compound is represented by the following formula (IV): and R ２２ and R ２３are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [5] The method according to any one of [1] to [4], wherein the resin film is provided so as to cover an electrode, and the resin film is polished by the chemical mechanical polishing to remove a portion of the resin film so as to expose the electrode. [6] The method according to any one of [1] to [5], further comprising heating the polished resin film to further harden the resin film. [7] A method for manufacturing a circuit connection body including a first circuit member having a first electrode and a second circuit member having a second electrode, the method comprising: preparing the first circuit member having the first electrode and a first insulating film, the first insulating film forming an opening and the first electrode being provided in the opening; joining the first circuit member having the first electrode and the first insulating film to the second circuit member having the second electrode and a second insulating film, the second insulating film forming an opening and the second electrode being provided in the opening, by hybrid bonding so that the first electrode and the second electrode are electrically connected; wherein preparing the first circuit member comprises: forming a thermosetting first resin film containing a maleimide compound having a maleimide group, the first resin film including a portion provided around the first electrode and covering the first electrode; and polishing the first resin film by the method according to any one of [1] to [5]; wherein by polishing the first resin film, a portion of the first resin film is removed to expose the first electrode, and the polished first resin film is the first insulating film.[8] A method for manufacturing a circuit connection body including a first circuit member having a first electrode and a second circuit member having a second electrode, the method comprising: preparing the first circuit member having the first electrode and a first insulating film, the first insulating film forming an opening and the first electrode being provided in the opening; preparing the second circuit member having the second electrode and a second insulating film, the second insulating film forming an opening and the second electrode being provided in the opening; joining the first circuit member having the first electrode and the first insulating film and the second circuit member having the second electrode and the second resin film by hybrid bonding so that the first electrode and the second electrode are electrically connected; preparing the first circuit member comprises: forming a thermosetting first resin film containing a maleimide compound having a maleimide group, the first resin film including a portion provided around the first electrode and covering the first electrode; and polishing the first resin film by the method according to any one of [1] to [5]. a method in which the first resin film is polished to remove a portion of the first resin film so as to expose the first electrode, and the polished first resin film is the first insulating film; and preparing the second circuit member comprises: forming a thermosetting second resin film containing a maleimide compound having a maleimide group, the second resin film including a portion provided around the second electrode and covering the second electrode; and polishing the second resin film by the method in any one of [1] to [5]; and a method in which the second resin film is polished to remove a portion of the second resin film so as to expose the second electrode, and the polished second resin film is the second insulating film.

[0009] A method for polishing a resin film can be provided that can polish a resin film at an appropriate polishing rate and form a surface having sufficiently small surface roughness.

[0010] 1A and 1B are process diagrams showing an example of a method for manufacturing a circuit-connected body; 2A and 2B are process diagrams showing an example of a method for manufacturing a circuit-connected body; 3A and 3B are process diagrams showing an example of a method for manufacturing a circuit-connected body;

[0011] The present invention is not limited to the following examples.

[0012] One example of a method for polishing a resin film includes semi-curing a thermosetting resin film containing a maleimide compound having a maleimide group by heat treatment, and polishing the semi-cured resin film by chemical mechanical polishing (CMP) while supplying an abrasive containing silica particles. The semi-cured resin film can be polished at a high polishing rate by CMP using an abrasive containing silica particles, and the surface of the polished resin film can have a sufficiently small surface roughness.

[0013] The thermosetting resin film can be formed, for example, by applying a curable resin composition containing a maleimide compound. The applied curable resin composition may contain a solvent. When a solvent-containing curable resin composition is used, the applied curable resin composition is heated to remove the solvent, thereby forming a resin film. The heating temperature for removing the solvent may be, for example, 60°C or higher and 150°C or lower. The resin film before heat treatment and the curable resin composition may further contain a reactive component that reacts with the maleimide compound. Details of the curable resin composition for forming the resin film will be described later. The thickness of the resin film may be, for example, 1 μm or higher and 100 μm or lower.

[0014] The formed resin film is subjected to heat treatment. The heat treatment conditions are adjusted so that the resin film is semi-cured without being completely cured. A resin film formed from a curable resin composition containing a maleimide compound can be easily semi-cured by adjusting heating conditions such as temperature and time. The heat treatment conditions are adjusted, for example, within the range of a temperature of 100°C or higher and 220°C or lower, or 120°C or higher and 180°C or lower, and a heating time of 10 minutes or higher and 120 minutes or lower.

[0015] The semi-curing of a resin film can be confirmed, for example, by observing heat generation due to curing in a DSC thermogram obtained by differential scanning calorimetry of a resin film sample. In the case of a completely cured resin film or curable resin composition, heat generation due to curing is not substantially observed. For example, a resin film showing a cure rate of more than 0% and less than 100% can be considered to be a semi-cured resin film. The cure rate can be determined by differential scanning calorimetry. In this case, the cure rate can be calculated using the formula: Cure rate [%] = 100 - (Q １ / Q ０ ) × 100. ０ is the heat generation amount [J / g] due to the curing reaction in the resin film before heat treatment, and Q １ is the amount of heat generated by the curing reaction in the resin film after heat treatment [J / g]. ０ and Q １ can be determined from the area of ​​the exothermic peak in a DSC thermogram obtained by differential scanning calorimetry at a heating rate of 10° C. / min and the mass of the measurement sample. The cure rate of the resin film semi-cured by heat treatment may be 90% or less, 85% or less, or 80% or less, or may be 10% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 55% or more, or 60% or more.

[0016] The abrasive for CMP contains silica particles as abrasive grains. The silica particles may be colloidal silica. Other CMP conditions can be adjusted within the range of normal conditions. For example, the resin film can be polished by pressing the resin film against a rotating polishing pad while supplying the abrasive onto the pad. By polishing the semi-cured resin film, a portion of the resin film is removed from the surface at a sufficiently high polishing rate, forming a surface with low surface roughness. The polishing time may be, for example, 10 seconds or more and 600 seconds or less.

[0017] A resin film may be provided so as to cover the electrodes. In this case, the resin film may be polished by chemical mechanical polishing to remove a portion of the resin film so as to expose the electrodes. By polishing the resin film, a flat surface including the resin film and the electrodes may be formed. However, a step may be formed between the resin film and the electrodes.

[0018] The polished resin film may be further hardened by heating. After the resin film is bonded to another member or subjected to other processing, it may be heated again to further harden. The heating temperature for the second heating may be, for example, 220°C or higher and 350°C or lower. The hardening rate of the resin film after the second heating may be, for example, 90% or higher and 100% or lower.

[0019] The above-exemplified methods for polishing a resin film can be applied, for example, to the manufacture of a circuit connection body having a resin film as an insulating film, or to the formation of a rewiring layer having a resin film as an insulating film.

[0020] 1, 2, and 3 are process diagrams illustrating an example of a method for manufacturing a circuit connection body. The method illustrated in FIGS. 1 to 3 includes 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 20 having a second substrate 21, a second electrode 22, and a second insulating film 23; and joining the first circuit member 10 and the second circuit member 20 by hybrid bonding so that the first electrode 12 and the second electrode 22 are electrically connected. This method forms a circuit connection body 1, which is a bonded assembly of the first circuit member 10 and the second circuit member 20. In hybrid bonding, for example, the first circuit member 10 and the second circuit member 20 are heated and pressurized, thereby bonding the first circuit member 10 and the second circuit member 20 so that the first insulating film 13 and the second insulating film 23 are bonded and the first electrode 12 and the second electrode 22 are bonded.

[0021] At least one of the first substrate 11 or the second substrate 21 may be a semiconductor substrate having a circuit surface. In this case, a semiconductor device is obtained as the circuit-connected body 1. Typically, an integrated circuit is provided on the circuit surface side of the semiconductor substrate. For example, the first substrate 11 may be a semiconductor wafer, and the second substrate 21 may be a semiconductor chip. A plurality of second circuit members 20 having semiconductor chips may be bonded to a single first circuit member 10 having a semiconductor wafer. In this case, the semiconductor wafer (first substrate 11) of the obtained circuit-connected body may be singulated into a plurality of semiconductor chips. The semiconductor substrate may be, for example, a silicon substrate. When the first circuit member 10 or the second circuit member 20 is not a semiconductor substrate, they may be various types of wiring substrates (e.g., interposers).

[0022] The first circuit member 10 has a plurality of first electrodes 12, and a first insulating film 13 is provided around the first electrodes 12 and includes a portion filling the gaps between the plurality of first electrodes 12. The first electrodes 12 and the first insulating film 13 are provided on a first substrate 11. When the first substrate 11 is a semiconductor substrate having a circuit surface, the first electrodes 12 and the first insulating film 13 are provided on the circuit surface. The first insulating film 13 forms a plurality of openings 13a which are through holes exposing the first substrate 11, and the first electrodes 12 are provided in the openings 13a.

[0023] The second circuit member 20 has a plurality of second electrodes 22, and the second insulating film 23 is provided around the second electrodes 22 and includes a portion that fills the gaps between the plurality of second electrodes 22. The second electrodes 22 and the second insulating film 23 are provided on a second substrate 21. When the second substrate 21 is a semiconductor substrate, the second electrodes 22 and the second insulating film 23 are provided on the circuit surface. The second insulating film 23 forms a plurality of openings 23a that are through holes that expose the second substrate 21, and the second electrodes 22 are provided in the openings 23a.

[0024] The first circuit member 10 is prepared by a method including providing a first electrode 12 on a main surface 11S of a first substrate as shown in FIG. 1(a), forming a thermosetting first resin film 13A on the main surface 11S of the first substrate 11 on the side of the first electrode 12 as shown in FIG. 1(b), semi-curing the first resin film 13A by heat treatment as shown in FIG. 1(c), and exposing the first electrode 12 by polishing the first insulating film 13, which is the semi-cured first resin film 13A, as shown in FIG. 2(a).

[0025] The first electrode 12 is made 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 plating.

[0026] The first resin film 13A covering the first electrode 12, including the portion surrounding the first electrode 12, can be formed by applying a curable resin composition containing a maleimide compound. When a solvent-containing curable resin composition is used, the first 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 first resin film 13A may be formed to cover the entire first electrode 12 while filling the gaps between the multiple first electrodes 12. By heat treating the formed first resin film 13A, the first resin film 13A is semi-cured to form the first insulating film 13. The first insulating film 13 before polishing contains a semi-cured curable resin composition. The curing rate of the first insulating film 13 containing the semi-cured curable resin composition may be within the same range as the curing rate of the semi-cured resin film.

[0027] The curing reaction of the first resin film 13A formed from the curable resin composition containing a maleimide compound is primarily an addition reaction such as radical polymerization and Diels-Alder reaction, and therefore is unlikely to generate volatiles due to elimination components. Furthermore, the surface of the first insulating film 13 formed from the curable resin composition containing a maleimide compound may contain many functional groups derived from maleimide groups, etc. Therefore, the first insulating film 13 may exhibit good adhesion without necessarily requiring an activation treatment such as plasma treatment. Additionally, the polishing rate of the first insulating film 13 may be adjustable based on the crosslink density, etc., of the first insulating film 13.

[0028] The conditions for the heat treatment of the first resin film 13A to form the first insulating film 13 are adjusted so that the first resin film 13A is semi-cured. For example, the heat treatment temperature may be 100° C. or higher and 220° C. or lower, or 120° C. or higher and 180° C. or lower. The heat treatment time may be, for example, 10 minutes or higher and 120 minutes or lower.

[0029] The first insulating film 13 (semi-cured first resin film) is polished by CMP using an abrasive containing silica particles. By polishing, a portion of the first insulating film 13 is removed from the side opposite the first substrate 11, forming an opening 13a through which the first electrode 12 is exposed. The surface of the tip of the first electrode 12 (the surface opposite the first substrate 11) may be flattened by polishing. Depending on the polishing rate, the height of the first electrode 12 may be greater than the thickness of the first insulating film 13 in the polished first circuit member 10. The difference between the height of the first electrode 12 and the thickness of the first insulating film 13 may be adjusted taking into account the difference in the linear thermal expansion coefficients of the first electrode 12 and the first insulating film 13, for example. The difference between the height of the first electrode 12 and the thickness of the first insulating film 13 may be, for example, 10 nm or more and 200 nm or less. The thickness of the first insulating film 13 may be, for example, 1 μm or more and 100 μm or less.

[0030] The second insulating film 23 of the second circuit member 20 can be an organic insulating film or an inorganic insulating film. When the second insulating film 23 is an organic insulating film, the second circuit member can be prepared in the same manner as the first circuit member 10, including heat treating the second resin film containing a curable resin composition and polishing the second insulating film. When both the first insulating film 13 and the second insulating film 23 are organic insulating films formed from a curable resin composition containing a maleimide compound, particularly good bonding properties are likely to be exhibited. The first insulating film 13 and the second insulating film 23 can be formed from the second resin film using the same or different curable resin compositions.

[0031] 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 21. 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.

[0032] From the viewpoint of bonding between electrodes, 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 a similar surface roughness Ra. The surface roughness Ra here is the arithmetic mean roughness (Ra) defined in JIS B 0601-2001.

[0033] 2(e), the prepared first circuit member 10 and second circuit member 20 are aligned so that the first electrode 12 and second electrode 22 to be bonded face each other. Then, as shown in FIG. 3, the first circuit member 10 and second circuit member 20 are heated and pressurized to bond the first electrode 12 and second electrode 22 and to bond the first insulating film 13 and second insulating film 23 together by hybrid bonding.

[0034] 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 proceed simultaneously or sequentially. For example, after heating and pressurizing mainly for bonding the first insulating film 13 and the second insulating film 23, the first circuit member 10 and the second circuit member 20 may be further heated and pressurized to bond the first electrode 12 and the second electrode 22. The first insulating film 13 and / or the second insulating film 23 may be further cured during the heating and pressurizing for bonding the first circuit member 10 and the second circuit member 20. The first insulating film 13 and / or the second insulating film 23 may be further cured by heating after bonding.

[0035] The conditions for heating and pressing for bonding are adjusted so that the insulating film and the electrode are properly bonded. For example, the heating temperature for bonding may be 150° C. or higher and 350° C. or lower, and the pressure for bonding may be 1.0 MPa or higher and 5.0 MPa or lower. The heating and pressing time may be, for example, 10 seconds or higher and 2 hours or lower.

[0036] In the above-exemplified methods, the curable resin composition used to form the resin film (first insulating film 13 and / or second insulating film 23) contains one or more maleimide compounds. 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 insulating film, the curable resin composition may contain a maleimide compound having two or more maleimide groups.

[0037] The maleimide compound may have a maleimide group containing a nitrogen atom directly bonded to a cyclic group (e.g., an aromatic group). For example, the maleimide compound may include a compound represented by the following formula (Ia), (Ib), or (Ic):

[0038] In formula (Ia), Q １ and Q ２ each independently represents a cyclic group which may have a substituent, and L ５ is a divalent organic group or a single bond. １ and Q ２ may each independently be an aromatic group (e.g., a phenylene group) which may have a substituent (e.g., an alkyl group having 1 to 3 carbon atoms). ５ 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, an alkylene group having 1 to 5 carbon atoms which may have a substituent (for example, a methylene group, a propane-1,3-diyl group, or a propane-2,2-diyl group), or a single bond. ５ 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. ５ is a cyclic group and Q １ or Q ２ and may further have a methylene group connecting L ５ However, L in formula (11) may have a cyclic group formed by removing one or more hydrogen atoms from benzene, 2,3-dihydro-1H-indene, or succinimide. Examples of the maleimide compound represented by formula (Ia) include a compound represented by formula (11) below. ５ is L in formula (Ia) ５ is defined in the same way as R ３１ is an alkyl group having 1 to 3 carbon atoms, and p and q are each independently an integer of 0 to 4. ３１ may be the same or different.

[0039] In formula (Ib), Q ３represents 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 have a substituent such as an alkyl group having 1 to 3 carbon atoms.

[0040] In formula (Ic), Q ４ , Q ５ and Q ６ are each independently a cyclic group which may have a substituent, and L ６ and L ７ are each independently a divalent organic group or a single bond, and n is an integer of 1 or more. ４ , Q ５ and Q ６ An example of this is Q １ and Q ２ This is similar to the example shown in L. ６ and L ７ An example of ５ Examples of the maleimide compound represented by formula (Ic) include a compound represented by formula (12): ６ and L ７ represents L in formula (Ia). ６ and L ７ where n is an integer of 1 or greater.

[0041] Specific examples of the maleimide compound include compounds represented by the following formulas 101, 102, 103, 104, and 105. In these formulas, n represents an integer of 1 or more.

[0042] Examples of commercially available maleimide compounds include NE-X-9470S (trade name, DIC), MIR-3000-70MT (trade name, Nippon Kayaku), BMI-1000 (trade name, Yamato Chemical Industries), 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).

[0043] The maleimide group of the maleimide compound may be blocked with a blocking agent that dissociates upon heating. In other words, the curable resin composition may contain a block maleimide compound having a blocked maleimide group. When the curable resin composition contains a block maleimide compound, the term "maleimide compound" in the following description can be read as "block maleimide compound."

[0044] The reactive component may include at least one compound selected from the group consisting of a styrene-based compound, an allyl compound, a phenolic compound, and a benzoxazine compound. The reactive component may include a styrene-based compound and an allyl compound.

[0045] The styrene-based compound is a compound having, as a reactive group, a group obtained by removing one or more hydrogen atoms bonded to a benzene ring from a compound represented by the following formula (IV): ２２ and R ２３ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms (for example, a methyl group). ２２ is a hydrogen atom, and R ２３ may be a hydrogen atom or an alkyl group having 1 to 3 carbon atoms (e.g., a methyl group). Styrenic compounds tend to react with maleimide compounds at relatively low temperatures. Styrenic compounds and maleimide compounds can react via a Diels-Alder reaction.

[0046] The styrene-based compound may have a plurality of reactive groups. The reactive group of the styrene-based compound is represented, for example, by the following formula (IVa) or (IVb). R in formulas (IVa) and (IVb) ２２ and R ２３ is R in formula (IV). ２２ and R ２ is defined in the same way as R １１ and R １２ is an alkyl group having 1 to 3 carbon atoms, p is an integer of 0 to 3, and q is an integer of 0 to 4. １１ and R １２ may be the same or different.

[0047] The styrene-based compound may be a polymer containing a structural unit represented by the following formula (41) or (42): ２２ and R ２３ is R in formula (I) ２２ and R ２３ In formula (41), L １ is a single bond or a divalent organic group, and R １１ is an alkyl group having 1 to 3 carbon atoms (for example, a methyl group), and p is an integer of 0 to 3. ２ is a single bond or a divalent organic group, and R １２ is an alkyl group having 1 to 3 carbon atoms (for example, a methyl group), and q is an integer of 0 to 4.

[0048] L １ or L ２ Examples of the divalent organic group as the aryl group include an oxy group (—O—), a —C(R １６ ) (R １７ )-, carbonyl group (-C(=O)-), carbonyloxy group (-C(=O)O-), amide group (-C(=O)NH-), carbonate group (-OC(=O)O-), sulfonyl group (-S(=O) ２ -), and thio groups (-S-). １６ and R １７ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0049] The polymer as the styrene-based compound may further contain a structural unit represented by the following formula (43): ３ is a single bond or a divalent organic group, and R １３ is an alkyl group having 1 to 3 carbon atoms, and r is an integer of 0 to 4. ３ Examples of divalent organic groups as L １ and L ２ The examples of the divalent organic group are the same as those of the above.

[0050] The styrene-based compound may be a polymer containing a structural unit represented by the following formula (401) or a polymer represented by the following formula (402). ２２ , R ２３ , L １ , L ２ , L ３ , R １１ , R １２ , R １３ , p, q and r are in formula (41), (42) or (43). ２２ , R ２３ , L １ , L ２ , L ３ , R １１ , R １２ , R １３ , p, q and r are defined in the same manner. １１ , L １２ and L １３ are each independently a single bond or a divalent organic group, and R １４ is an alkyl group having 1 to 3 carbon atoms (for example, a methyl group), s is an integer of 0 to 4, and m and n are each independently an integer of 1 or more. １１ , L １２ or L １３ Examples of divalent organic groups as L １ or L ２ The examples of divalent organic groups are the same as those of the above. １４ may be the same or different.

[0051] The molecular weight of the styrene-based compound may be 200 or more and 100,000 or less. The weight average molecular weight and / or number average molecular weight of the styrene-based compound may be 500 or more and 100,000 or less. In this specification, the weight average molecular weight and number average molecular weight may be values ​​calculated as standard polystyrene measured by gel permeation chromatography.

[0052] The reactive component may include an allyl compound having an allyl group as a reactive group. The allyl compound may have one or more allyl groups (2-propenyl group, —CH ２ CH=CH ２From the viewpoints of improving the heat resistance and reducing the thermal expansion coefficient of the cured resin, the curable resin composition may contain an allyl compound having two or more allyl groups.

[0053] 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 (Va), (Vb), (Vc), or (Vd):

[0054] In formulas (Va) and (Vb), Q ７ and Q ８ each independently represents a cyclic group which may have a substituent, L ８ represents a divalent organic group or a single bond. ７ and Q ８ may each independently be a group in which one or more hydrogen atoms have been removed from benzene, isocyanuric acid, or nadimide. ８ 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. ８ 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. ８ is a cyclic group and Q ７ or Q ８ and may further have a methylene group connecting L ８ 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. ８ may have a phenylene group which may have a substituent.

[0055] In formulas (Vc) and (Vd), Q ９ represents a cyclic group which may have a substituent. ９may 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. ９ The cyclic groups therein may be substituted, for example, with methyl or allyl groups.

[0056] Specific examples of the allyl compound include compounds represented by the following formulae 501, 502, 503, 504, 505, 506, 507, 508 and 509. In these formulae, n represents an integer of 1 or more.

[0057] 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).

[0058] The curable resin composition may contain an allyl compound (hereinafter sometimes referred to as an "allylamino compound") having a reactive group represented by the following formula (5). The allylamino compound may have a plurality of reactive groups represented by formula (5). The allylamino compound tends to react with the bismaleimide compound at a relatively low temperature.

[0059] The allylamino compound may be a compound represented by the following formula (50): ２４ and R ２５ are each independently a hydrogen atom or a monovalent organic group, and R ２４ and R ２５ may be bonded to each other to form a cyclic group.

[0060] R ２４ or R２５ The monovalent organic group represented by R may be a hydrocarbon group (for example, an alkyl group having 1 to 6 carbon atoms) which may have a substituent. ２４ and R ２５ may be bonded to each other to form a cyclic group having 4 to 8 members. Specific examples of the allylamino compound include compounds represented by the following formula 510:

[0061] The phenol compound is a compound having a phenolic hydroxyl group as a reactive group. The benzoxazine compound is a compound having a benzoxazine group. The benzoxazine compound can generate the phenolic hydroxyl group as a reactive group by heating.

[0062] The content of the reactive component may be 10% by mass or more and 80% by mass or less, based on the total amount of the maleimide compound and the reactive component. The content of the reactive component 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 reactive component, and may be 75% by mass or less, 70% by mass or less, 65% by mass or less, or 60% by mass or less. The total content of the maleimide compound and the reactive component may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more, or may be 100% by mass or less, based on the total amount of components in the curable resin composition excluding the solvent.

[0063] The curable resin composition may further contain a solvent that dissolves or disperses the maleimide compound and the reactive component. Examples of the solvent include γ-butyrolactone, cyclohexanone, cyclopentanone, mesitylene, N,N-dimethylformamide, propylene glycol monomethyl ether acetate, and ethyl lactate. The content of the solvent may be, for example, 10% by mass or more and 300% by mass or less based on the total amount of the maleimide compound and the reactive component.

[0064] The curable resin composition may further include a component that initiates or accelerates the reaction of the maleimide compound and the reactive component.

[0065] The curable resin composition may further contain a component that reduces the dielectric loss tangent of the cured resin (insulating film) (hereinafter referred to as a "dielectric loss tangent adjuster"). The dielectric loss tangent adjuster includes, for example, an aromatic compound represented by the following formula (VIa), (VIb), or (VIc):

[0066] In formula (VIa), R ４１ , R ４４ and R ４５ each independently represents a hydrogen atom, a methyl group, or a t-butyl group; R ４２ and R ４３ 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.

[0067] In formula (VIb), R ４６ , R ４９ , R ５０ , R ５１ , R ５２ and R ５５ each independently represents a hydrogen atom, a methyl group, or a t-butyl group; R ４７ , R ４８ , R ５３ and R ５４ 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.

[0068] In formula (VIc), R ５６ , R ５９ , R ６０ , R ６１ , R ６４ , R ６５ , R ６６ , R ６７ and R ７０ each independently represents a hydrogen atom, a methyl group, or a t-butyl group; R ５７ , R ５８ , R ６２ , R６３ , R ６８ and R ６９ 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.

[0069] 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 reactive component. 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 reactive component, and may be 50% by mass or less or 40% by mass or less.

[0070] The curable resin composition may further include an adhesion promoter, such as a silane coupling agent, an aluminum-based adhesion promoter, or a combination thereof.

[0071] 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.

[0072] Examples of aluminum-based adhesion promoters include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0073] 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 reactive component.

[0074] The curable 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.

[0075] 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 reactive component.

[0076] The curable 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-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.

[0077] 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 reactive component.

[0078] The curable 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.

[0079] 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 reactive component.

[0080] The curable resin composition may contain an organic titanium 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.

[0081] 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).

[0082] 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}].

[0083] 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.

[0084] Examples of monoalkoxytitanium compounds include titanium tris(dioctylphosphate) isopropoxide and titanium tris(dodecylbenzenesulfonate) isopropoxide.

[0085] Examples of titanium oxide compounds include titanium oxide bis(pentanedionate), titanium oxide bis(tetramethylheptanedionate), and phthalocyanine titanium oxide.

[0086] An example of a titanium tetraacetylacetonate compound is titanium tetraacetylacetonate.

[0087] An example of a titanate coupling agent is isopropyl tridodecylbenzenesulfonyl titanate.

[0088] 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 reactive component.

[0089] [Examples] The present invention is not limited to the following examples. 1. Curable resin composition (varnish) The following components were mixed in the blending ratios (parts by mass) shown in Table 1 to prepare curable resin compositions A and B. (A) Maleimide compound A1: Phenylmethanemaleimide (BMI-2300, Daiwa Chemical Industry Co., Ltd.)

[0090] (B) Reactive component allyl compound B1: aryl phenol resin (LVA01, Gun-ei Chemical Industry Co., Ltd.)

[0091] Allyl compound B2: 1,3,4,6-tetraallylglycoluril (TA-G, Shikoku Chemicals Corporation)

[0092] Styrene-based compound B3 2,2'-diallylbisphenol A (Tokyo Chemical Industry Co., Ltd., 6.00 mmol, 1.85 g), 4,4'-difluorobenzophenone (Tokyo Chemical Industry Co., Ltd., 5.00 mmol, 1.09 g), and potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd., 30.0 mmol, 4.15 g) were placed in a three-necked flask. N-methylpyrrolidone (30 mL) and toluene (15 mL) were then added. The three-necked flask was equipped with a reflux condenser and a Dean-Stark receiver, and the system was conditioned with a nitrogen atmosphere. The reaction solution in the three-necked flask was heated while stirring. After the internal temperature reached 155°C, stirring was continued for an additional 30 minutes to allow the reaction to proceed. The reaction solution in the three-necked flask was then cooled to room temperature, and N-methylpyrrolidone (30 mL) was added thereto. The reaction solution was washed several times with water and ethanol, and then filtered to obtain a styrene-based compound B3 (white solid) (yield: 85%, weight average molecular weight: 28,000). １ The H-NMR spectrum confirmed that a 1-propenyl group was formed. (C) Silane coupling agent C1: 3-aminopropyltriethoxysilane (D) Azole compound D1: 1,2,3-benzotriazole (E) Solvent γ-butyrolactone (γ-BL)

[0093]

[0094] 2. Heat Treatment of Resin Film Curable resin composition A or B was dropped onto a silicon wafer (diameter: 12 inches) and a film was formed by spin coating. The solvent was removed from the coating by heating at 110°C for 3 minutes to form a resin film. Subsequently, the resin film was heat treated under the conditions shown in Table 2 in a nitrogen atmosphere.

[0095] 3. Cure Rate The cure rate of the resin film after heat treatment was measured using a differential scanning calorimeter (DSC8500, manufactured by PerkinElmer). The solvent was removed from the coating film of curable resin composition A or B by heating at 110°C for 3 minutes. Approximately 10 mg of a sample of curable resin composition A or B from which the solvent had been removed was sealed in an aluminum pan. The sample pan containing the sample was placed in the holder of the differential scanning calorimeter together with an empty sample pan. After holding at 0°C for 15 minutes, the temperature was raised to 300°C at a heating rate of 10°C / min to obtain a DSC thermogram of the curable resin composition. The amount of heat Q generated by the curing reaction was calculated from the integrated value of the area of ​​the exothermic peak associated with the curing reaction in the DSC thermogram and the weight of the sample. ０ [J / g] was obtained. ０ is substantially equivalent to the amount of heat generated in the curing reaction of the resin film before the heat treatment. Subsequently, about 10 mg of the resin film after the heat treatment was sampled and sealed in an aluminum pan, and a DSC thermogram was obtained under the same conditions as for the sample of the curable resin composition. From the obtained DSC thermogram, the amount of heat generated by the curing reaction of the resin film after the heat treatment, Q １ The curing rate was calculated using the following formula: Curing rate [%] = 100 - (Q １ / Q ０ ) x 100

[0096] 4. Polishing Test The heat-treated resin film was polished by CMP under the following conditions: Polishing device: CMP polishing machine FREX300X (manufactured by Ebara Corporation) Polishing pad: porous urethane pad IC-1010 (manufactured by Rohm and Haas Japan Co., Ltd.) Polishing pressure: 3.0 psi Platen rotation speed: 87 rpm Head rotation speed: 93 rpm Abrasive (slurry): slurry containing colloidal silica or slurry containing alumina particles Amount of abrasive supplied: 300 mL / min Polishing time: 60 seconds

[0097] 5. Polishing Rate The thickness of the resin film before and after polishing was measured using an optical interference film thickness measuring device (device name: F40) manufactured by Filmetrics. The film thickness was measured at 79 equally spaced points on a line passing through the center of the silicon wafer surface, and the average value was calculated. The average film thickness before polishing, t ０ [μm], average film thickness after polishing t１ The polishing rate was calculated by substituting the polishing time T [min] and the polishing surface roughness [μm] into the following formula: ０ -t １ ) / T

[0098] 6. Surface Roughness After polishing, the surface roughness Ra (arithmetic mean roughness) of an area of ​​10 μm×10 μm located 75 mm from the center of the resin film was measured using an atomic force microscope (manufactured by BRUKER, model number: InSight CAP).

[0099]

[0100] The evaluation results are shown in Table 2. In each example, it was confirmed that a surface having small surface roughness can be formed at a sufficiently high polishing rate by polishing the semi-cured resin film by CMP using an abrasive containing silica particles. In the case of the resin films of Comparative Examples 2 and 3, which had a curing rate of 100%, polishing did not substantially progress by CMP using an abrasive containing silica particles.

[0101] 1...circuit connector, 10...first circuit member, 11...first substrate, 12...first electrode, 13...first insulating film, 13a, 23a...opening, 13A...first resin film, 20...second circuit member, 21...second substrate, 22...second electrode, 23...second insulating film.

Claims

1. A method for polishing a resin film, comprising: semi-curing a thermosetting resin film containing a maleimide compound having a maleimide group by heat treatment; and polishing the semi-cured resin film by chemical mechanical polishing while supplying an abrasive containing silica particles.

2. The curing rate of the resin film semi-cured by the heat treatment is 90% or less, and the curing rate is expressed by the formula: Curing rate [%] = 100 - (Q １ / Q ０ ) × 100, and Q ０ is the heat generation amount [J / g] due to the curing reaction in the resin film before the heat treatment, and Q １ The method according to claim 1 , wherein the heat generation amount [J / g] due to the curing reaction in the resin film after the heat treatment is 3. The method according to claim 1, wherein the resin film before the heat treatment further contains a reactive component that reacts with the maleimide compound.

4. The reactive component includes one or more compounds selected from the group consisting of a styrene-based compound, an allyl compound having an allyl group, a phenolic compound having a phenolic hydroxyl group, and a benzoxazine compound having a benzoxazine group, and the styrene-based compound is represented by the following formula (IV): and R ２２ and R ２３ and each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

5. The method according to claim 1, wherein the resin film is provided so as to cover the electrodes, and the resin film is polished by the chemical mechanical polishing, thereby removing a portion of the resin film so as to expose the electrodes.

6. The method of claim 1, further comprising: further curing the resin film by heating the polished resin film.

7. A method for manufacturing a circuit connection body comprising a first circuit member having a first electrode and a second circuit member having a second electrode, the method comprising: preparing the first circuit member having the first electrode and a first insulating film, the first insulating film forming an opening and the first electrode being provided in the opening; joining the first circuit member having the first electrode and the first insulating film to the second circuit member having the second electrode and a second insulating film, the second insulating film forming an opening and the second electrode being provided in the opening, by hybrid bonding so that the first electrode and the second electrode are electrically connected; preparing the first circuit member comprises: forming a thermosetting first resin film containing a maleimide compound having a maleimide group, the first resin film including a portion provided around the first electrode and covering the first electrode; and polishing the first resin film by the method defined in any one of claims 1 to 5; by polishing the first resin film, a portion of the first resin film is removed to expose the first electrode, and the polished first resin film is the first insulating film.

8. A method for manufacturing a circuit connection body comprising a first circuit member having a first electrode and a second circuit member having a second electrode, the method comprising: preparing the first circuit member having the first electrode and a first insulating film, the first insulating film forming an opening and the first electrode being provided in the opening; preparing the second circuit member having the second electrode and a second insulating film, the second insulating film forming an opening and the second electrode being provided in the opening; joining the first circuit member having the first electrode and the first insulating film and the second circuit member having the second electrode and the second insulating film by hybrid bonding so that the first electrode and the second electrode are electrically connected; preparing the first circuit member comprises: forming a thermosetting first resin film containing a maleimide compound having a maleimide group, the first resin film including a portion provided around the first electrode and covering the first electrode; and polishing the first resin film by the method according to any one of claims 1 to 5. a second resin film that is a thermosetting resin film containing a maleimide compound having a maleimide group, the second resin film including a portion provided around the second electrode and covering the second electrode; and ...

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