Resin composition, and insulating adhesive film, multilayer substrate, electronic component, and semiconductor device each using same

Abstract

Provided is a resin composition having excellent embeddability with respect to an electronic substrate and the periphery of an electronic element and excellent slittability for a B-stage film.　The resin composition contains (A) a thermosetting resin, (B) a compound that has a butadiene skeleton having a 1,2 vinyl group, and (C) a compound that has an isocyanuric ring structure and has one or two double bonds at a molecular terminal. The number average molecular weight of the component (B) is 1,000-10,000. Preferably, the minimum melt viscosity is 500-5,000. Preferably, the component (B) is a compound that has a styrene skeleton.

Description

Resin composition, and insulating adhesive film, laminated substrate, electronic component, and semiconductor device using the same

[0001] The present invention relates to a resin composition, and to an insulating adhesive film, a laminated substrate, an electronic component, and a semiconductor device using the same.

[0002] In recent years, communication speeds and capacity have been increasing for electronic communication devices such as mobile terminals such as smartphones and tablets, communication base stations, and advanced driving assistance systems (ADAS), and the construction of 5G communication networks using high-frequency signals is progressing. Furthermore, the use of even higher-frequency signals, such as 6G communication, is also being actively considered. Electronic circuit boards, which are made up of multiple stacked boards, are essential components for these high-frequency communications.

[0003] An electronic substrate is formed by laminating multiple substrates with an adhesive film for interlayer insulation therebetween. The adhesive film for interlayer insulation is required to have the ability to embed into a wiring pattern when laminating and adhering the substrates. Hereinafter, the "adhesive film for interlayer insulation" may be referred to as the "adhesive film." The adhesive film may also be used for the purpose of sealing electronic elements, and similarly, the adhesive film is required to have the ability to embed around the electronic elements.

[0004] Conventionally, a method has been known in which a block copolymer containing a butadiene structure is blended into an adhesive film to improve molding flowability and embeddability (see, for example, Patent Document 1).

[0005] Furthermore, adhesive films are shipped in a rolled state or cut into pieces, and then processed, such as by cutting. When cutting adhesive films, they are required to have excellent slitting properties, i.e., to be less likely to develop chips or cracks when cut. If chips or cracks develop in the adhesive film, the affected areas cannot be used as adhesive film, and the yield decreases.

[0006] Japanese Patent Application Laid-Open No. 2006-104276

[0007] The inventors have found that when an adhesive film contains a block copolymer having a butadiene structure, the adhesive film is prone to chipping and cracking. The adhesive film is a film formed by drying a varnish formed by dissolving a resin composition in a solvent, and this film is in a state known as a B-stage state. In other words, a film in a B-stage state containing a resin composition containing a block copolymer having a butadiene structure has poor slitting properties.

[0008] The present invention has been made in view of the above problems and circumstances, and aims to provide a resin composition that has excellent embeddability in the periphery of an electronic substrate or electronic element and has excellent slitting properties when formed into a film in a B-stage state, as well as an insulating adhesive film, a laminated substrate, an electronic component, and a semiconductor device that use the resin composition.

[0009] In order to solve the above-mentioned problems, the present inventors have investigated the causes of the above-mentioned problems. As a result of intensive research, the inventors have found that by incorporating a combination of a low-molecular-weight compound having a butadiene skeleton with 1,2-vinyl groups and a specific compound into an adhesive film, an adhesive film can be obtained that has excellent slitting properties in a B-stage state while maintaining excellent embeddability. Specifically, the above-mentioned problems according to the present invention are solved by the following means.

[0010] [1] A resin composition comprising: (A) a thermosetting resin; (B) a compound having a butadiene skeleton with a 1,2-vinyl group; and (C) a compound having an isocyanuric ring structure and one or two double bonds at a molecular terminal, wherein the number average molecular weight of the component (B) is 1,000 to 10,000.

[0011] [2] The resin composition according to [1] above, having a minimum melt viscosity of 500 to 5000.

[0012] [3] The resin composition according to the above [1] or [2], wherein the component (B) is a compound having a styrene skeleton.

[0013] [4] The resin composition according to any one of [1] to [3] above, wherein the component (B) is a styrene-butadiene block copolymer.

[0014] [5] The resin composition according to any one of [1] to [4] above, wherein the component (B) is a styrene-butadiene-styrene block copolymer represented by the following structural formula (1), or a hydrogenated product thereof:

[0015]

[0016] (In the structural formula (1), m, o, p, and q each independently represent a positive integer, n represents 0 or a positive integer, and the relationship of o:p:q = 1-20:60-98:1-20 is satisfied, and the relationship of m:n = 100:0-80:20 is satisfied.)

[0017] [6] The resin composition according to any one of [1] to [5] above, wherein the 1,2-vinyl structure in the butadiene skeleton of the component (B) is 5 to 95 mass %.

[0018] [7] The resin composition according to any one of [1] to [6] above, wherein the component (C) is liquid.

[0019] [8] The resin composition according to any one of the above [1] to [7], wherein the component (C) has two allyl groups at the molecular terminals.

[0020] [9] The resin composition according to any one of the above [1] to [8], wherein the component (C) is a compound represented by the following structural formula (2):

[0021]

[0022] (In the structural formula (2), R is an alkyl group having 4 to 14 carbon atoms.)

[0023]

[10] The resin composition according to any one of [1] to [9] above, wherein the component (A) comprises at least one selected from the group consisting of a polyphenylene ether resin, a maleimide compound, and an epoxy resin.

[0024]

[11] The resin composition according to any one of [1] to

[10] above, wherein the mass ratio of the (B) component to the (C) component is 10:90 to 90:10.

[0025]

[12] The resin composition according to any one of [1] to

[11] , which is used to form a rewiring layer.

[0026]

[13] An insulating adhesive film made of the resin composition according to any one of [1] to

[12] above.

[0027]

[14] The insulating adhesive film according to

[13] , which is used to form an interlayer insulating layer.

[0028]

[15] The insulating adhesive film according to

[13] , which is used for sealing electronic elements.

[0029]

[16] A laminated substrate comprising the resin composition according to any one of the above [1] to

[12] or the cured insulating adhesive film according to any one of the above

[13] to

[15] .

[0030]

[17] An electronic component comprising the laminated substrate according to

[16] above.

[0031]

[18] A semiconductor device comprising the laminated substrate according to

[16] above or the electronic component according to

[17] above.

[0032] The resin composition of the present invention exhibits the effects of excellent embeddability around electronic substrates and electronic elements and excellent slitting properties of the film in a B-stage state. In particular, the resin composition of the present invention has excellent molding flowability and embeddability because it contains "(B) a compound having a butadiene skeleton with 1,2 vinyl groups." Furthermore, the resin composition of the present invention has excellent slitting properties in a B-stage state because it contains "(C) a compound having an isocyanuric ring structure and one or two double bonds at the molecular terminal."

[0033] Furthermore, since the insulating adhesive film of the present invention is made from the resin composition of the present invention, it exhibits the effects of being excellent in embedding properties around electronic substrates and electronic elements and in slitting properties. Furthermore, the laminated substrate, electronic component, and semiconductor device of the present invention contain a cured product of the resin composition or insulating adhesive film of the present invention, and enjoy the effects of the present invention described above.

[0034] 1 is a schematic diagram illustrating a method for evaluating the slittability of a resin film. FIG. 2 is a plan view schematically illustrating a film after cutting when evaluating the slittability of a resin film.

[0035] While the present invention will be described below with reference to exemplary embodiments, it should be understood that the present invention is not limited to the following exemplary embodiments. Therefore, it should be understood that modifications and improvements to the following exemplary embodiments, based on the ordinary knowledge of those skilled in the art, are also within the scope of the present invention, provided that they do not deviate from the spirit of the present invention.

[0036] In the present specification, numerical ranges indicated using "to" include the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In numerical ranges described in stages in the present specification, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another staged numerical range. Furthermore, in numerical ranges described in the present specification, the upper or lower limit value of that numerical range may be replaced with a value shown in the examples. In the present specification, each component may contain multiple corresponding substances. When multiple substances corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple substances present in the composition, unless otherwise specified. In the present specification, each component may contain multiple types of particles. When multiple types of particles corresponding to each component are present in the composition, the particle size of each component means the value for a mixture of the multiple types of particles present in the composition, unless otherwise specified.

[0037] In this specification, the term "B stage" (state) is synonymous with the term "B stage" among the three stages defined in JIS K6900:1994: A stage refers to the initial stage in the preparation of certain thermosetting resins, where the material is still soluble and fusible in certain liquids. The term "B stage" refers to the intermediate stage in the reaction of certain thermosetting resins, where the material swells when in contact with certain liquids and softens when heated, but does not completely dissolve or melt. The term "C stage" refers to the final stage in the reaction of certain thermosetting resins, where the material is virtually insoluble and infusible.

[0038] [Resin Composition] One embodiment of the resin composition of the present invention is a resin composition comprising (A) a thermosetting resin, (B) a compound having a butadiene skeleton with 1,2-vinyl groups, and (C) a compound having an isocyanuric ring structure and one or two double bonds at the molecular terminal, wherein the number average molecular weight of the component (B) is 1,000 to 10,000. Hereinafter, the thermosetting resin (A) may be referred to as component (A). Similarly, the compound (B) having a butadiene skeleton with 1,2-vinyl groups may be referred to as component (B). Similarly, the compound (C) having an isocyanuric ring structure and one or two double bonds at the molecular terminal may be referred to as component (C).

[0039] The resin composition of this embodiment exhibits the effects of excellent embeddability around electronic substrates and electronic elements and excellent slitting properties of the film in a B-stage state. In particular, the resin composition of the present invention contains "(B) a compound having a butadiene skeleton with 1,2 vinyl groups," and therefore has excellent molding flowability and embeddability. Furthermore, the resin composition of the present invention contains "(C) a compound having an isocyanuric ring structure and one or two double bonds at the molecular terminal," and therefore has excellent slitting properties in a B-stage state. Furthermore, the compound having a butadiene skeleton with 1,2 vinyl groups as component (B) has a number average molecular weight of 1,000 to 10,000, and therefore has excellent flowability.

[0040] [Component (A)] Component (A) is a thermosetting resin. The thermosetting resin of component (A) is not particularly limited, but examples include resins having reactive functional groups, such as polyphenylene ether compounds, compounds having maleimide groups, epoxy resins, polyimide compounds, siloxane compounds, and (meth)acrylate compounds. Furthermore, component (A) may have one or more reactive functional groups, such as maleimide groups, allyl groups, vinyl groups, vinylbenzyl groups, and (meth)acryloyl groups. From the viewpoint of improving curability, component (A) preferably contains a compound having two or more reactive functional groups. Among these, component (A) preferably includes (A1) a polyphenylene ether compound having an unsaturated bond at its terminal, (A2) a compound having a maleimide group, and (A3) an epoxy resin. Hereinafter, "(A1) a polyphenylene ether compound having an unsaturated bond at its terminal" may be referred to as component (A1). Furthermore, "(A2) a compound having a maleimide group" may be referred to as component (A2). Furthermore, (A3) an epoxy resin may be referred to as component (A3). Furthermore, as component (A1), (A11) a polyphenylene ether resin having a group represented by the following formula (3) at its terminal, and (A12) a polyphenylene ether resin having a vinylbenzyl group at its terminal, are preferred. Hereinafter, "a polyphenylene ether resin having a group represented by the following formula (3) at its terminal" may be referred to as component (A11). Furthermore, "a polyphenylene ether resin having a vinylbenzyl group at its terminal" may be referred to as component (A12). Component (A11) may also be referred to as a terminally (meth)acrylic-modified polyphenylene ether resin. Component (A12) may also be referred to as a terminally styrene-modified polyphenylene ether resin. From the viewpoint of improving fluidity, the number average molecular weight of component (A) is preferably at least 100 but less than 25,000, more preferably 150 to 22,000, even more preferably 200 to 20,000, particularly preferably 250 to 18,000, and most preferably 300 to 15,000. The number average molecular weight of component (A) is, for example, preferably at least 100, more preferably at least 150, even more preferably at least 200, particularly preferably at least 250, and most preferably at least 300.The number average molecular weight of component (A) is, for example, preferably less than 25,000, more preferably not more than 22,000, even more preferably not more than 20,000, particularly preferably not more than 18,000, and most preferably not more than 15,000. In this specification, the number average molecular weight may be measured by a general molecular weight measurement method, and specific examples include values ​​measured using gel permeation chromatography (GPC).

[0041]

[0042] (However, in the above formula (3), R １ represents a hydrogen atom or an alkyl group.

[0043] [Component (A1)] Component (A1) is a polyphenylene ether compound having an unsaturated bond at its terminal. As described above, the component (A1) is preferably a polyphenylene ether resin (A11) having a group represented by the following formula (3) at its terminal, or a polyphenylene ether resin (A12) having a vinylbenzyl group at its terminal. Components (A11) and (A12) are described below.

[0044] [Component (A11)] As described above, component (A11) is a polyphenylene ether resin having a group represented by formula (3) at its terminal. There are no particular limitations on component (A11) as long as it has a group represented by formula (3) at its terminal and a polyphenylene ether in its skeleton. By including component (A11), heat resistance and heat resistance reliability can be extremely effectively improved. Hereinafter, a polyphenylene ether resin having a group represented by formula (3) as component (A11) may be referred to as a modified polyphenylene ether having a group represented by formula (3).

[0045] In the above formula (3), R １ represents a hydrogen atom or an alkyl group. １ The alkyl group is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 carbon atom. Specific examples include a methyl group, an ethyl group, and a propyl group.

[0046] Examples of the group represented by formula (3) include an acryloyl group and a methacryloyl group.

[0047] Furthermore, the modified polyphenylene ether having a group represented by formula (3) has a polyphenylene ether chain in the molecule, and preferably has, for example, a repeating unit represented by the following structural formula (4) in the molecule.

[0048]

[0049] In the structural formula (4), m represents 1 to 50. ２２ ~R ２５ are each independently and may be the same as or different from one another. ２２ ~R ２５ represents a hydrogen atom or an alkyl group.

[0050] R ２２ ~R ２５ The alkyl group in is not particularly limited, but is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a hexyl group, and an octyl group.

[0051] Examples of modified polyphenylene ethers having a group represented by formula (3) include those having a group represented by formula (3) at the terminal of a polyphenylene ether represented by formula (5) or (6) below. Specific examples of modified polyphenylene ethers having a group represented by formula (3) include modified polyphenylene ethers represented by formula (7) or (8) below.

[0052]

[0053]

[0054]

[0055]

[0056] In formulas (5) to (8), s and t are preferably such that the sum of s and t is, for example, 1 to 30. Furthermore, s is preferably 0 to 20, and t is preferably 0 to 20. That is, it is preferable that s represents 0 to 20, t represents 0 to 20, and the sum of s and t represents 1 to 30. Furthermore, in formulas (5) to (8), Y represents an alkylene group having 1 to 3 carbon atoms or a direct bond, and examples of this alkylene group include a dimethylmethylene group. Furthermore, in formulas (7) and (8), R １ is R in the above formula (3). １ and represents a hydrogen atom or an alkyl group. The alkyl group is not particularly limited, and is preferably, for example, an alkyl group having 1 to 3 carbon atoms, and more preferably an alkyl group having 1 carbon atom. Specific examples include a methyl group, an ethyl group, and a propyl group.

[0057] The number-average molecular weight (Mn) of the modified polyphenylene ether having a group represented by formula (3) is not particularly limited. Specifically, it is preferably 500 to 5,000, more preferably 800 to 4,000, and even more preferably 1,000 to 3,000. Here, the number-average molecular weight may be measured by a general molecular weight measurement method, and specifically, a value measured using gel permeation chromatography (GPC) may be used. Furthermore, when the modified polyphenylene ether having a group represented by formula (3) has a repeating unit represented by formula (4) in the molecule, m is preferably a value such that the weight-average molecular weight of the modified polyphenylene ether falls within this range. Specifically, m is preferably 1 to 50.

[0058] When the number-average molecular weight of the modified polyphenylene ether having a group represented by formula (3) is within the above-mentioned range, it has excellent dielectric properties derived from the polyphenylene ether and also has excellent embeddability in the periphery of a substrate or an electronic element. For example, when the number-average molecular weight of a conventional polyphenylene ether is within the above-mentioned range, it has a relatively low molecular weight and tends to have excellent embeddability in the periphery of a substrate or an electronic element. On the other hand, since the modified polyphenylene ether having the group represented by formula (3) has the group represented by formula (3) at its terminal, it can improve the heat resistance and heat resistance reliability of the cured product.

[0059] Furthermore, in the modified polyphenylene ether used as component (A11), the average number of groups represented by the above formula (3) at the molecular terminals per molecule of the modified polyphenylene ether (number of terminal functional groups) is not particularly limited. Specifically, it is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.5 to 3. Within this numerical range, the curing properties are excellent, and the strength, adhesiveness, and heat resistance of the cured product are sufficient. Furthermore, the shelf life of the resin composition can be ensured and the flowability of the resin composition can be improved. In other words, the use of such modified polyphenylene ether reduces molding defects such as the generation of voids during multilayer substrate molding, making it possible to obtain highly reliable printed wiring boards free from cracks and delamination in the substrate.

[0060] The number of terminal functional groups in the modified polyphenylene ether described above can be, for example, a numerical value representing the average number of groups represented by the above formula (3) per molecule of all modified polyphenylene ethers present in 1 mole of the modified polyphenylene ether. This number of terminal functional groups can be measured, for example, by measuring the number of hydroxyl groups remaining in the obtained modified polyphenylene ether and calculating the difference from the number of hydroxyl groups in the polyphenylene ether before modification. This difference from the number of hydroxyl groups in the polyphenylene ether before modification is the number of terminal functional groups. The number of hydroxyl groups remaining in the modified polyphenylene ether can be measured by adding a quaternary ammonium salt (tetraethylammonium hydroxide) that associates with hydroxyl groups to a solution of the modified polyphenylene ether and measuring the UV absorbance of the resulting mixed solution.

[0061] Furthermore, the method for synthesizing the modified polyphenylene ether used as component (A11) is not particularly limited as long as it is possible to synthesize a modified polyphenylene ether having a group represented by the above formula (3) at its terminal.

[0062] The component (A11) may be a modified polyphenylene ether having a group represented by the above formula (3) at its terminal, which may be used alone, or two or more modified polyphenylene ethers having a group represented by the above formula (3) at their terminal may be used in combination.

[0063] An example of the modified polyphenylene ether having a group represented by the above formula (3) at its terminal, which is the component (A11), is Noryl SA9000, a product name manufactured by SABIC Innovative Plastics.

[0064] [Component (A12)] Examples of the vinylbenzyl group-terminated polyphenylene ether resin of component (A12) include compounds having a structure represented by the following general formula (9).

[0065]

[0066]

[0067]

[0068]

[0069] In the general formula (9), —(OXO)— is represented by the structural formula (10) or (11).

[0070] In structural formula (10), R ２ , R ３ , R ４ , R ８ , and R ９ R is an alkyl group having 6 or less carbon atoms or a phenyl group, and may be the same as or different from each other. ５ , R ６ , and R ７ are hydrogen atoms, alkyl groups having 6 or less carbon atoms, or phenyl groups, and may be the same as or different from each other.

[0071] In structural formula (11), R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , and R １７ represents a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and may be the same as or different from each other. -A- represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0072] In addition, in the general formula (9), -(Y-O)- is represented by the above structural formula (12). In -(Y-O)-, one type of structure or two or more types of structures are randomly arranged. In the structural formula (12), R １８ and R １９ R is an alkyl group having 6 or less carbon atoms or a phenyl group, and may be the same as or different from each other. ２０ and R ２１ are hydrogen atoms, alkyl groups having 6 or less carbon atoms, or phenyl groups, and may be the same as or different from each other.

[0073] In the general formula (9), a and b are integers of 0 to 100. At least one of a and b is not 0.

[0074] Examples of -A- in structural formula (11) include divalent organic groups such as methylene, ethylidene, 1-methylethylidene, 1,1-propylidene, 1,4-phenylenebis(1-methylethylidene), 1,3-phenylenebis(1-methylethylidene), cyclohexylidene, phenylmethylene, naphthylmethylene, and 1-phenylethylidene, however, -A- in structural formula (4) is not limited to these.

[0075] The compound represented by the general formula (9) includes R ２ , R ３ , R ４ , R ８ , R ９ , R １８ , and R １９ is an alkyl group having 3 or less carbon atoms, and R ５ , R ６ , R ７ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , R ２０ , and R ２１ is preferably a hydrogen atom or an alkyl group having 3 or less carbon atoms. In particular, it is more preferable that -(O-X-O)- represented by structural formula (10) or structural formula (11) is a compound represented by the following structural formula (13), structural formula (14), or structural formula (15). Similarly, it is more preferable that -(Y-O)- represented by structural formula (12) is a compound represented by the following structural formula (16) or structural formula (17), or a structure in which compounds represented by structural formula (16) and compounds represented by structural formula (17) are randomly arranged.

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] The method for producing the compound represented by general formula (9) is not particularly limited. For example, the compound represented by general formula (9) can be produced by the following method. First, a bifunctional phenylene ether oligomer is obtained by oxidative coupling of a bifunctional phenol compound and a monofunctional phenol compound. Next, the terminal phenolic hydroxyl groups of the obtained bifunctional phenylene ether oligomer are converted to vinylbenzyl ether. In this manner, the compound represented by general formula (9) can be produced.

[0082] Furthermore, in the modified polyphenylene ether used as component (A12), the average number of vinylbenzyl groups (number of terminal functional groups) having the structure represented by the above formula (9) at the molecular terminals per molecule of the modified polyphenylene ether is not particularly limited. Specifically, it is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.5 to 3. Within this numerical range, the curing properties are excellent, and the strength, adhesiveness, and heat resistance of the cured product are sufficient. Furthermore, the shelf life of the resin composition can be ensured and the flowability of the resin composition can be improved. In other words, the use of such modified polyphenylene ether reduces molding defects such as the generation of voids during multilayer substrate molding, and enables the production of highly reliable printed wiring boards free from cracks and delamination of the substrate.

[0083] The number-average molecular weight of the compound represented by general formula (9) is preferably 500 to 5,000, more preferably 1,000 to 4,000, and particularly preferably 1,000 to 3,000. By setting the number-average molecular weight of the compound represented by general formula (9) within the above numerical range, the compound exhibits excellent solubility, low dielectric constant, fluidity, and heat resistance. For example, a number-average molecular weight of 1,000 or more reduces stickiness when the resin composition is formed into a coating film. Furthermore, a number-average molecular weight of 3,000 or less effectively prevents a decrease in the solubility of the resin composition in solvents. Furthermore, by using a compound having a number-average molecular weight within the above numerical range as component (A12), the electrical properties and curability of the resin composition at high frequencies are improved. Here, the above-mentioned number-average molecular weight is a value determined by gel permeation chromatography (GPC) using a calibration curve based on standard polystyrene.

[0084] As the component (A12), a compound represented by general formula (9) may be used alone, or two or more compounds represented by general formula (9) may be used in combination.

[0085] Examples of the polyphenylene ether resin having a vinylbenzyl group at the end of the component (A12) include the trade names "OPE2St-2200" and "OPE2St-1200" manufactured by Mitsubishi Gas Chemical Company, Inc.

[0086] The components (A11) and (A12) may be used in combination.

[0087] [Component (A2)] Component (A2) is a compound having a maleimide group as described above. By including component (A2), the minimum melt viscosity can be lowered. That is, since thermosetting resins having maleimide groups have high bond energy, the reaction proceeds slowly, which is thought to result in a lower minimum melt viscosity. A lower minimum melt viscosity improves embeddability.

[0088] Furthermore, the compound having a maleimide group of component (A2) can be, for example, a thermosetting resin having a maleimide group at its terminal.

[0089] The thermosetting resin having a maleimide group at its terminal, used as component (A2), can be, for example, a compound containing one or more maleimide groups in the molecule, as represented by the following general formula (13): Monomaleimide compounds and polymaleimide compounds are preferably used, and are represented by the following general formulas (18), (19), (20), (21), or (22):

[0090]

[0091] However, in the above general formula (18), R ３１ is an r-valent aliphatic, alicyclic, aromatic, or heterocyclic monovalent or polyvalent organic group. Xa and Xb are the same or different monovalent atoms or organic groups selected from hydrogen atoms, halogen atoms, and aliphatic organic groups. r is an integer of 1 or greater.

[0092] In the above general formula (18), R ３１ is preferably phenyl, alkylphenyl, dialkylphenyl, alkoxyphenyl, benzyl, dodecyl, alkyl, or cycloalkyl. Xa and Xb are preferably hydrogen atoms.

[0093]

[0094] However, in the above general formula (19), R ３２ is a monovalent or divalent organic group which is aliphatic, alicyclic, aromatic, or heterocyclic, and s is 0 or 1.

[0095] In the above general formula (19), s is 0, and R ３２ When R is a monovalent group, it is preferably phenyl, alkylphenyl, dialkylphenyl, alkoxyphenyl, benzyl, dodecyl, alkyl, or cycloalkyl. ３２ When is a divalent group, it is preferably alkylene, fluorene, cyclohexylene-alkylene-cyclohexylene.

[0096]

[0097] However, in the above general formula (20), R３３ is -C(Xc) ２ -, -CO-, -O-, -S-, -SO ２ Xc is an alkyl group having 1 to 4 carbon atoms, -CF ３ , -OCH ３ , -NH ２ , a halogen atom, or a hydrogen atom, which may be the same or different. In the general formula (20), the substitution positions of the benzene rings are independent of each other. Furthermore, t and u represent 0 or an integer of 1 to 10.

[0098] Specific examples of the monomaleimide compound represented by general formula (18) or (19) (when s is 0) include N-phenylmaleimide, N-(2-methylphenyl)maleimide, N-(4-methylphenyl)maleimide, N-(2,6-dimethylphenyl)maleimide, N-(2,6-diethylphenyl)maleimide, N-(2-methoxyphenyl)maleimide, N-benzylmaleimide, N-dodecylmaleimide, N-isopropylmaleimide, and N-cyclohexylmaleimide.

[0099] Specific examples of the polymaleimide compound represented by the general formula (20) or (19) (when s is 1) include 1,2-dimaleimidoethane, 1,3-dimaleimidopropane, bis(4-maleimidophenyl)methane, bis(3-ethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,7-dimaleimidofluorene, N,N'-(1,3-phenylene)bismaleimide, N,N'-(1,3-(4-methylphenylene))bismaleimide, bis(4-maleimidophenyl)sulfone, bis(4-maleimidophenyl)sulfide, bis(4-maleimidophenyl)ether, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(3-(3-maleimidophenoxy)phenoxy)benzene, and bis(4-maleimidophenyl)ketone. , 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, bis(4-(4-maleimidophenoxy)phenyl)sulfone, bis[4-(4-maleimidophenoxy)phenyl]sulfoxide, 4,4'-bis(3-maleimidophenoxy)biphenyl, 1,3-bis(2-(3-maleimidophenyl)propyl)benzene, 1,3-bis(1-(4-(3-maleimidophenoxy)phenyl)-1-propyl)benzene, bis(maleimidocyclohexyl)methane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, bis(maleimidophenyl)thiophene, aliphatic, alicyclic, aromatic and heterocyclic polymaleimides such as those represented by the following general formulas (21) and (22) (however, each includes isomers).

[0100]

[0101] In the general formula (21), v is an average value of 0 to 10.

[0102]

[0103] In the general formula (22), w is an average value of 0 to 10.

[0104] Aromatic polymaleimides are preferred from the viewpoints of moisture resistance, heat resistance, breaking strength, metal foil peel strength, and low thermal expansion characteristics when formed into a printed wiring board. Among them, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane is more preferred in terms of further reducing the thermal expansion coefficient, and 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane is more preferred in terms of further increasing breaking strength and metal foil peel strength.

[0105] Furthermore, monomaleimides, which undergo a slow curing reaction, are preferred in terms of improving formability when formed into an adhesive film. Among them, N-phenylmaleimide is more preferred in terms of cost. The above maleimide compounds may be used alone or in combination of two or more, or at least one of these maleimide compounds may be used in combination with one or more crosslinking agents.

[0106] When a maleimide compound is used in combination with another crosslinking agent, the proportion of the maleimide compound in component (A2) is preferably 50% by mass or more, and more preferably 80% by mass or more. However, it is more preferable to use the maleimide compound alone rather than in combination with another crosslinking agent.

[0107] The thermosetting resin having a maleimide group at its terminal, used as component (A2), may be, for example, a maleimide compound represented by the following general formula (23):

[0108]

[0109] In the above general formula (23), y is the number of repetitions, and 1<y<5.

[0110] The content of N,N'-(phenylene-di-(2,2-propylidene)-di-p-phenylene)bismaleimide in the maleimide compound represented by general formula (23), as determined by GPC analysis (RI), is usually 90 area % or less, preferably 10 to 80 area %, more preferably 20 to 80 area %, and even more preferably 30 to 70 area %. When the content of N,N'-(phenylene-di-(2,2-propylidene)-di-p-phenylene)bismaleimide is 90 area % or less, crystallinity decreases, thereby improving solvent solubility. On the other hand, the lower limit of N,N'-(phenylene-di-(2,2-propylidene)-di-p-phenylene)bismaleimide may be 0 area %, but when it is 10 area % or more, a decrease in reactivity can be suppressed.

[0111] The content of y=1 in the maleimide compound represented by general formula (23) as determined by GPC analysis (RI) is preferably 98 area% or less, more preferably 20 to 98 area%, even more preferably 30 to 90 area%, and particularly preferably 40 to 80 area%. When the content of y=1 is 98 area% or less, heat resistance is improved. On the other hand, although the lower limit of y=1 may be 0 area%, when it is 20 area% or more, the viscosity of the resin solution is reduced and impregnation properties are improved.

[0112] The softening point of the maleimide compound represented by general formula (23) is preferably 50 to 150° C., more preferably 80 to 120° C., even more preferably 90 to 110° C., and particularly preferably 95 to 100° C. The melt viscosity at 150° C. is 0.05 to 100 Pa s, preferably 0.1 to 40 Pa s.

[0113] The maleimide compound represented by general formula (23) more preferably has a structure represented by the following general formula (24), because the crystallinity is lower than when the substitution position of the propyl group relative to the benzene ring to which the maleimide group is not bonded in general formula (23) is para-positioned.

[0114]

[0115] In the general formula (24), y is the number of repeats, and 1<y<5.

[0116] The number-average molecular weight of the maleimide compound as component (A2) described above is preferably 400 to 3,000, and more preferably 700 to 2,500. By setting the number-average molecular weight of the maleimide compound within this range, the maleimide compound will have better solubility, low dielectric constant, fluidity, and heat resistance. Here, the number-average molecular weight of the maleimide compound described above is a value obtained by gel permeation chromatography (GPC) using a calibration curve with standard polystyrene.

[0117] As the maleimide compound as component (A2), the maleimide compounds explained above may be used alone or in combination of two or more compounds.

[0118] Examples of the thermosetting resin having a maleimide group of component (A2) include a maleimide resin manufactured by K.I. Chemical Industry Co., Ltd. (trade name "BMI70") and a maleimide resin manufactured by Nippon Kayaku Co., Ltd. (trade name "MIR-5000-60T").

[0119] [Component (A3)] Component (A3) is an epoxy resin. There are no particular limitations on the epoxy resin, and any known epoxy resin can be used. For example, the following epoxy resins can be used:

[0120] Examples of the epoxy resin (A3) include bisphenol-type epoxy resins such as bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, and bisphenol AF-type epoxy resins, bixylenol-type epoxy resins, cyclohexane-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol novolac-type epoxy resins, phenol novolac-type epoxy resins, tert-butyl-catechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins (glycidylamine-type epoxy resins having no aromatic structure or glycidylamine-type epoxy resins having an aromatic structure), glycidyl ester-type epoxy resins (glycidyl ester-type epoxy resins having no aromatic structure or glycidyl ester-type epoxy resins having an aromatic structure), cresol novolac-type epoxy resins, biphenyl-type epoxy resins, and linear aliphatic epoxy resins (linear aliphatic epoxy resins having no aromatic structure). Examples of the epoxy resin include aromatic or aliphatic epoxy resins such as epoxy resins or linear aliphatic epoxy resins having an aromatic structure), epoxy resins having a butadiene structure (epoxy resins having a butadiene structure but not an aromatic structure or epoxy resins having a butadiene structure but not an aromatic structure), alicyclic epoxy resins (alicyclic epoxy resins having an aromatic structure but not an aromatic structure or alicyclic epoxy resins having an aromatic structure), heterocyclic epoxy resins, spiro ring-containing epoxy resins (spiro ring-containing epoxy resins having an aromatic structure or spiro ring-containing epoxy resins having an aromatic structure), cyclohexanedimethanol-type epoxy resins (cyclohexanedimethanol-type epoxy resins having an aromatic structure but not an aromatic structure or cyclohexanedimethanol-type epoxy resins having an aromatic structure), naphthylene ether-type epoxy resins, trimethylol-type epoxy resins (trimethylol-type epoxy resins having an aromatic structure but not an aromatic structure or trimethylol-type epoxy resins having an aromatic structure), tetraphenylmethane-type epoxy resins, aminophenol-type epoxy resins, and silicone-modified epoxy resins. The epoxy resin (A3) may be solid or liquid, but is preferably liquid from the viewpoint of improving slittability.The epoxy resin (A3) preferably has two or more epoxy groups.

[0121] The content of component (A) in the resin composition is not particularly limited, but preferably contains 50 to 90 parts by mass of component (A) per 100 parts by mass of the total resin components, more preferably 60 to 80 parts by mass, and particularly preferably 65 to 75 parts by mass. Furthermore, the content of component (A) is preferably 50 parts by mass or more, more preferably 60 parts by mass or more, and even more preferably 65 parts by mass or more per 100 parts by mass of the total resin components. Furthermore, the content of component (A) is, for example, preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less per 100 parts by mass of the total resin components. When the content of component (A) per 100 parts by mass of the total resin components is within this range, the curability is good, and the flexibility of the resin composition, the heat resistance of the cured product, and processability such as film formation are improved, and the toughness of the cured product is not lost, and adhesion properties are not reduced. The content of component (A) in the resin components can be measured, for example, by infrared spectroscopy (FTIR) or gas chromatography mass spectrometry. Examples of resin components in the resin composition include component (A), component (B), and component (C). Therefore, the content of component (A) per 100 parts by mass of the resin components in the resin composition can be determined, for example, as the content of component (A) per 100 parts by mass of the resin components (A), component (B), and component (C). The content of component (B) per 100 parts by mass of the resin components, which will be described later, can also be calculated in the same manner as above.

[0122] The resin composition of this embodiment preferably contains at least one of the components (A1), (A2), and (A3) as the component (A). The component (A1) is preferably contained in an amount of 70 to 100 mass%, more preferably 80 to 100 mass%, based on the total amount of the component (A). The component (A2) is preferably contained in an amount of 0 to 30 mass%, more preferably 0 to 20 mass%, based on the total amount of the component (A). The component (A3) is preferably contained in an amount of 0 to 40 mass%, more preferably 0 to 30 mass%, based on the total amount of the component (A). By configuring the component (A1) as described above, it is possible to obtain a resin composition having low dielectric properties, a low CTE, and a low melt viscosity. By configuring the component (A2) as described above, it is possible to obtain a resin composition having low dielectric properties, high heat resistance, and high adhesive strength. By configuring the component (A3) as described above, it is possible to obtain a resin composition having low CTE and high adhesive strength. Two or more of the components (A1) to (A3) may be used in combination.

[0123] [Component (B)] Component (B) is a compound having a butadiene skeleton with 1,2 vinyl groups. The inclusion of component (B) can improve molding flowability and embeddability. In particular, by forming a butadiene-containing resin having 1,2 vinyl groups into a copolymer or block copolymer structure with styrene, a resin composition with excellent molding flowability and embeddability around electronic substrates and electronic elements can be obtained. Thus, component (B) is preferably a compound having a styrene skeleton. Furthermore, the compound having a butadiene skeleton with 1,2 vinyl groups as component (B) has a number-average molecular weight of 1,000 to 10,000. By achieving such a number-average molecular weight, good flowability and a good thermal expansion coefficient can be achieved. Here, the number-average molecular weight of the compound serving as component (B) is determined by gel permeation chromatography (GPC) using a calibration curve based on standard polystyrene.

[0124] Examples of the compound as component (B) include the following components (B1), (B2), and (B3).

[0125] The (B1) component is a butadiene copolymer having a 1,2-vinyl group. For example, the use of such a (B1) component can improve molding flowability and embeddability around electronic substrates and electronic elements. Furthermore, the use of such a (B1) component can reduce the amount of monomer used, making it possible to obtain a suitable cured product without using a monomer. On the other hand, butadiene copolymers having a 1,2-vinyl group do not have a styrene skeleton, and therefore tend to have weaker adhesion (particularly peel strength of the roughened surface (M surface)). Such butadiene copolymers are not particularly limited as long as they have a 1,2-vinyl group and a number-average molecular weight of 1,000 to 10,000.

[0126] Examples of the component (B1) include 1,2-polybutadiene homopolymers (trade names "B-3000" and "B-1000") manufactured by Nippon Soda Co., Ltd., and partially hydrogenated products (trade name "BI-3015").

[0127] Component (B2) is a styrene-butadiene block copolymer having a 1,2-vinyl structure. For example, the use of such component (B2) can improve molding flowability and embeddability around electronic substrates and electronic elements. Furthermore, the use of component (B2) can improve peel strength and reduce the thermal expansion coefficient.

[0128] Component (B2) is a block copolymer containing a butadiene block and a styrene block. The styrene block is a block obtained by polymerizing styrene, and the butadiene block is a block obtained by polymerizing butadiene. Such a styrene-butadiene block copolymer is not particularly limited as long as it has 1,2 vinyl groups and a number average molecular weight of 1,000 to 10,000. The butadiene block consists solely of a 1,2 bond structure represented by the following formula (25), or consists of a 1,2 bond structure represented by formula (25) and a 1,4 bond structure represented by formula (26).

[0129]

[0130]

[0131] The molar ratio of the 1,2-bond structure represented by formula (25) to the 1,4-bond structure represented by formula (26) contained in the styrene-butadiene block copolymer having a 1,2-vinyl structure of component (B2) is preferably 80:20 to 100:0.

[0132] The mass ratio of the styrene block to the butadiene block in component (B2) is not particularly limited, but examples include 10:90 to 80:20, 10:90 to 70:30, 10:90 to 60:40, 10:90 to 50:50, 20:80 to 80:20, 30:70 to 80:20, and 40:60 to 80:20. Of these, 10:90 to 80:20, 10:90 to 70:30, 10:90 to 60:40, and 10:90 to 50:50 are preferred, with 10:90 to 50:50 being more preferred.

[0133] The component (B2) is preferably a styrene-butadiene-styrene block copolymer represented by the following structural formula (1), or a hydrogenated product thereof.

[0134]

[0135] In the structural formula (1), m, o, p, and q each independently represent a positive integer, n represents 0 or a positive integer, and the relationship of o:p:q = 1-20:60-98:1-20 is satisfied, and the relationship of m:n = 100:0-80:20 is satisfied.

[0136] By using a styrene-butadiene-styrene block copolymer as represented by the above structural formula (1) as component (B), it is possible to further improve the peel strength and reduce the thermal expansion coefficient.

[0137] The method for producing component (B2) is not particularly limited. For example, a styrene-butadiene-styrene block copolymer can be produced by the methods described in JP-A-6-192502, JP-A-2000-514122, JP-A-2007-302901, or similar methods.

[0138] Examples of the component (B2) include the trade names "1,2-SBS-L42" and "1,2-H-SBS-L" manufactured by Nippon Soda Co., Ltd.

[0139] Component (B3) is a styrene-butadiene copolymer having a 1,2-vinyl group. Such a styrene-butadiene copolymer is not particularly limited as long as it has a 1,2-vinyl group and a number-average molecular weight of 1,000 to 10,000. Such a styrene-butadiene copolymer is hydrophobic and has few polar groups. Therefore, adding it to a resin composition can further improve low dielectric properties. Furthermore, due to its relatively small molecular weight, it exhibits high solubility not only in nonpolar organic solvents such as toluene but also in polar organic solvents such as methyl ethyl ketone, despite its hydrophobic backbone. Therefore, it is easily dissolved in various solvents when made into a resin composition, and when dissolved in a solvent to form a resin varnish, it has the advantage of excellent varnish stability. The use of such a component (B3) can improve molding flowability and embeddability around electronic substrates and electronic elements. On the other hand, because component (B3) is a random copolymer rather than a block copolymer, it tends to have weak adhesion (peel strength of the glossy surface (S surface)). In other words, it is presumed that if the phenyl groups are not aligned, it will be difficult to achieve strength on a flat surface.

[0140] In addition, since the styrene-butadiene copolymer is liquid, the flexibility of the resin composition is improved, and there is also the advantage that the handling properties (such as powder falling) of the resin composition are improved when it is brought into a B-stage state.

[0141] Component (B3) is preferably a styrene-butadiene copolymer having crosslinkable 1,2-vinyl groups in the molecule, which makes it more reactive than typical styrene-butadiene polymers having many 1,4-bonds in the main chain. Furthermore, because the number-average molecular weight is low, at 10,000 or less, the reactivity of the 1,2-vinyl groups in the styrene-butadiene copolymer is also thought to be higher. These factors contribute to the curing reaction, preventing bleeding of the resin and resulting in an excellent appearance after molding.

[0142] More specifically, the component (B3) may be, for example, a styrene-butadiene copolymer having the structure shown in the following formula (27).

[0143]

[0144] The above formula (27) is an example of a styrene-butadiene copolymer, and in the above formula (27), d represents a 1,2 vinyl group, e represents a styrene group, and f represents a 1,4-bond.

[0145] Examples of structural units having a 1,2-vinyl group include a structural unit of the following formula (28): Furthermore, examples of structural units having a 1,4-bond include a structural unit of the following formula (29): Furthermore, examples of styrene groups include a structural unit of the following formula (30):

[0146]

[0147]

[0148]

[0149] The styrene-butadiene copolymer having a 1,2-vinyl group preferably has a repeating structure of the structural unit of formula (28) and a repeating structure of the structural unit of formula (30). It may further contain a repeating structure of the structural unit of formula (29).

[0150] In the styrene-butadiene copolymer of component (B3), the styrene content in the molecule is preferably 50% by mass or less and the butadiene content is preferably 50% by mass or more. Furthermore, it is even more preferable that the styrene content be 20 to 50% by mass and the butadiene content be 50 to 80% by mass. That is, the relationships between d, e, and f shown in the above formula (27) are preferably: e / (d + e + f) = 20 to 50% and (d + f) / (d + e + f) = 50 to 80%, respectively. It is believed that a styrene content within the above range can produce a resin composition with a well-balanced and excellent high Tg and adhesion. Furthermore, it is believed that a butadiene content within the above range can reliably reduce the elastic modulus of the resin composition, thereby reducing the in-plane thermal expansion coefficient when the resin composition is formed into a laminate. Reducing the in-plane thermal expansion coefficient can reduce warpage of substrates, such as package substrates. The styrene and butadiene content in styrene-butadiene copolymers can be measured, for example, by nuclear magnetic resonance spectroscopy (NMR).

[0151] Examples of styrene-butadiene copolymers of component (B3) include those available under the trade names "Ricon 181" and "Ricon 100" from CRAY VALLEY.

[0152] The compound as component (B) is preferably a compound having a styrene skeleton. For example, among the components (B1), (B2), and (B3) described above, a styrene-butadiene block copolymer having a 1,2-vinyl structure as component (B2) is more preferred from the viewpoints of flowability, embeddability, thermal expansion coefficient, adhesion strength, and heat resistance reliability.

[0153] The number average molecular weight of component (B) is not particularly limited as long as it is 1,000 to 10,000, but is, for example, preferably 1,000 to 8,000, more preferably 1,000 to 5,000, and particularly preferably 3,500 to 5,000. When measuring the number average molecular weight of a film made of the resin composition, for example, the film may be dissolved in a solvent and the number average molecular weight of the component dissolved in the solvent may be measured.

[0154] Furthermore, the compound serving as component (B) preferably has 5 to 95% by mass, more preferably 10 to 95% by mass, and particularly preferably 20 to 95% by mass of 1,2-vinyl structures in its butadiene skeleton. Setting the content of 1,2-vinyl structures in the butadiene skeleton within the above range is advantageous in terms of lowering the minimum melt viscosity. For example, such a compound may be a butadiene resin containing 5 to 95% by mass of 1,2-vinyl structures. The content of 1,2-vinyl structures can be measured by FT-IR, NMR, or the like.

[0155] The content of component (B) is preferably 5 to 100 parts by mass per 100 parts by mass of component (A). This configuration provides advantages in terms of heat resistance and chemical resistance due to the reaction with component (A). While not particularly limited, the content of component (B) is more preferably 5 to 80 parts by mass, even more preferably 7 to 60 parts by mass, particularly preferably 9 to 50 parts by mass, and most preferably 12 to 45 parts by mass per 100 parts by mass of component (A).

[0156] [Component (C)] Component (C) is a compound having an isocyanuric ring structure and one or two double bonds at the molecular terminal. By including component (C), the resin composition of this embodiment has excellent slitting properties in a B-stage state. Furthermore, by including component (C), the melt viscosity of the resin composition can be reduced, improving the embeddability around substrates and electronic elements. Furthermore, by including one or two double bonds at the molecular terminal, the compound as component (C) can achieve extremely good low dielectric properties. Component (C) is preferably a compound having an isocyanuric ring structure and two double bonds at the molecular terminal, and more preferably a compound having an isocyanuric ring structure and two allyl groups at the molecular terminal.

[0157] For example, if a compound having an isocyanuric ring structure and three allyl groups in one molecule is used instead of component (C), sufficiently low dielectric properties cannot be obtained. A compound having an isocyanuric ring structure and three allyl groups in one molecule has an isocyanuric ring structure and three double bonds at the molecular terminals. Using a compound having three allyl groups results in a three-dimensional crosslinked structure, which is presumed to result in insufficient dielectric properties. On the other hand, a compound having a bifunctional allyl group, such as component (C) of the resin composition of this embodiment, results in a linear crosslinked structure, which reduces the dipole moment, a measure of molecular polarization, and is presumed to result in low dielectric properties. It is presumed that the heat resistance and heat resistance reliability of the resin composition are improved by the isocyanuric ring structure of component (C). It is preferable that component (C) of the resin composition of this embodiment is a liquid compound, as this improves embeddability. It is preferable that component (C) is liquid at 25°C.

[0158] As described above, the resin composition of this embodiment, by including component (C), exhibits excellent slitting properties in a B-stage state. This is because component (C) is a low-viscosity liquid compound, which moistens the film and improves film-forming properties and slitting processability. When a compound having an isocyanuric ring structure and three allyl groups in one molecule is used, film-forming properties and slitting processability deteriorate. For example, when triallyl isocyanurate is used as a compound having an isocyanuric ring structure and three allyl groups in one molecule, triallyl isocyanurate is easily volatilized, so some of it volatilizes during drying, leaving a small amount of liquid material (triallyl isocyanurate) remaining in the film after drying, thereby weakening the moistening effect. This is presumably one of the causes of the deterioration. In addition, when triallyl isocyanurate is compared with the compound of formula (2) described later as component (C), it is presumed that the difference in structure (the difference between the functional group being three allyl groups or two allyl groups and one alkyl group) is that triallyl isocyanurate having three allyl groups is poor in film-forming property and slit processability, while the compound represented by formula (2) having two allyl groups and one alkyl group is excellent in film-forming property and slit processability.In addition, it is also presumed that compared with the allyl group, the long-chain alkyl group is excellent in film-forming property and slit processability.

[0159] The molecular weight of component (C) is preferably 300 to 400, and more preferably 320 to 400. When the molecular weight of component (C) is within the above range, the dielectric properties, fluidity, and slitting properties are excellent.

[0160] The component (C) is preferably a compound represented by the following structural formula (2).

[0161]

[0162] In the structural formula (2), R is an alkyl group having 4 to 14 carbon atoms, preferably an alkyl group having 8 to 14 carbon atoms, and particularly preferably an alkyl group having 10 to 12 carbon atoms.

[0163] The mass ratio of component (B) to component (C) is preferably 10:90 to 90:10, more preferably 15:85 to 85:15, even more preferably 20:80 to 80:20, and particularly preferably 25:75 to 75:25. By configuring in this manner, the resin composition of this embodiment exhibits superior molding flowability and embeddability. Furthermore, this also results in excellent slitting properties in the B-stage state.

[0164] The resin composition preferably contains 3 to 40 parts by mass of component (C) per 100 parts by mass of the resin components (component (A), component (B), and component (C)) combined, more preferably 5 to 30 parts by mass, and particularly preferably 10 to 25 parts by mass. The content of component (C) is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the resin components combined. The content of component (C) is preferably, for example, 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less, per 100 parts by mass of the resin components combined. When the content of component (C) per 100 parts by mass of the resin components combined is within this range, the melt viscosity of the resin composition is reduced, improving embeddability around electronic substrates and electronic elements, while preventing a decrease in the heat resistance and heat resistance reliability of the cured product and a deterioration in dielectric properties. Furthermore, when the content of component (C) is within the above range, the resin composition exhibits excellent slittability in the B-stage state. The content ratio of component (C) and the content in the resin component can be measured, for example, by a method such as infrared spectroscopy (FTIR) or gas chromatography mass spectrometry.

[0165] An example of the compound (C) having an isocyanuric ring structure and one or two double bonds at the molecular terminal is "L-DAIC," a trade name manufactured by Shikoku Chemicals Corporation. "L-DAIC" has an isocyanuric ring structure and two allyl groups in one molecule and is a liquid compound at 25°C. "L-DAIC" is a compound having the structure of formula (2) above.

[0166] The resin composition of this embodiment may further include a (D) thermoplastic elastomer, a (E) reaction accelerator, and a (F) inorganic filler. Hereinafter, the (D) thermoplastic elastomer may be referred to as the (D) component. The (E) reaction accelerator may be referred to as the (E) component. The (F) inorganic filler may be referred to as the (F) component.

[0167] [Component (D)] Component (D) is a thermoplastic elastomer. Examples of the thermoplastic elastomer component include styrene-based thermoplastic elastomers and hydrogenated styrene-based thermoplastic elastomers. Examples of styrene-based thermoplastic elastomers include styrene / butadiene / styrene block copolymers (SBS). Here, hydrogenated styrene-based thermoplastic elastomers refer to hydrogenated styrene-based thermoplastic elastomers. Examples of hydrogenated styrene-based thermoplastic elastomers include styrene / butadiene / butylene / styrene block copolymers (partially hydrogenated, SBBS) and styrene / ethylene / butylene / styrene block copolymers (fully hydrogenated, SEBS). The use of hydrogenated styrene-based thermoplastic elastomers can improve dielectric properties. When component (D) is a styrene-based thermoplastic elastomer, the styrene ratio of component (D) is preferably 10 to 50%, more preferably 15 to 40%, and even more preferably 20 to 35%. By setting the styrene ratio of component (D) within the above range, excellent film-forming properties and workability are achieved.

[0168] The thermoplastic elastomer component (D) is not particularly limited, but preferably contains at least one selected from the group consisting of styrene / butadiene / styrene block copolymer (SBS), styrene / butadiene / butylene / styrene block copolymer (SBBS), and styrene / ethylene / butylene / styrene block copolymer (SEBS). By including styrene / butadiene / styrene block copolymer (SBS) as component (D), excellent heat resistance is achieved. By including styrene / butadiene / butylene / styrene block copolymer (SBBS) as component (D), excellent heat resistance and dielectric properties are achieved. By including styrene / ethylene / butylene / styrene block copolymer (SEBS) as component (D), excellent dielectric properties and heat aging resistance are achieved. Furthermore, in some embodiments, it is preferable that component (D) contains a hydrogenated styrene-based thermoplastic elastomer.

[0169] The number average molecular weight of the thermoplastic elastomer component of component (D) is not particularly limited, but is preferably 10,000 to 1,000,000, more preferably 20,000 to 500,000, and particularly preferably 20,000 to 200,000. When component (D) is a compound having a butadiene skeleton with 1,2 vinyl groups, the number average molecular weight of component (D) exceeds 10,000.

[0170] The content of component (D) is not particularly limited, but for example, it is preferably 5 to 100 parts by mass, more preferably 8 to 60 parts by mass, and even more preferably 10 to 30 parts by mass, of component (D) relative to 100 parts by mass of the total of components (A), (B), and (C). By having the content of component (D) within this range, the effects of containing component (D) can be improved in heat resistance, fluidity, and film-forming properties. Furthermore, the linear expansion coefficient can be effectively reduced.

[0171] [Component (E)] Component (E) is a reaction accelerator. The reaction accelerator as component (E) is an additive for accelerating the reaction of components (A), (B), and (C). By including such component (E), the reaction initiation temperature is shifted to a lower temperature, and curing of the resin composition is accelerated.

[0172] The reaction accelerator for component (E) may be any accelerator that accelerates the reaction between components (A), (B), and (C), and any conventionally known accelerator may be used. Examples of the accelerator include organic peroxides, inorganic peroxides, and azo compounds. Organic peroxides are preferred as the accelerator for component (E).

[0173] Examples of organic peroxides include diacyl peroxides such as benzoyl peroxide, isobutyryl peroxide, isononanoyl peroxide, decanoyl peroxide, lauroyl peroxide, parachlorobenzoyl peroxide, and di(3,5,5-trimethylhexanoyl)peroxide; peroxyketals such as 2,2-di(4,4-di-(di-tert-butylperoxy)cyclohexyl)propane; isopropyl percarbonate; Peroxydicarbonates such as sec-butyl purge carbonate, di-2-ethylhexyl purge carbonate, di-1-methylheptyl purge carbonate, di-3-methoxybutyl purge carbonate, and dicyclohexyl purge carbonate; tert-butyl perbenzoate, tert-butyl peracetate, tert-butyl per-2-ethylhexanoate, tert-butyl perisobutyrate, tert-butyl perpivalate, and tert-butyl Peroxy esters such as diperadipate, cumyl perneodecanoate, tert-butyl peroxybenzoate, and 2,5-dimethyl-2,5-di(benzoylperoxy)hexane; ketone peroxides such as methyl ethyl ketone peroxide and cyclohexanone peroxide; dialkyl peroxides such as di-tert-butyl peroxide, dicumyl peroxide, tert-butylcumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3,1,1-di(t-hexylperoxy)-3,3,5-trimethylcyclohexane, di-tert-hexyl peroxide, and di(2-tert-butylperoxyisopropyl)benzene; and hydroperoxides such as cumene hydroxyperoxide, tert-butyl hydroperoxide, and p-menthahydroperoxide can be used. There are no particular restrictions on the organic peroxide used, but since a drying step at, for example, about 60 to 80° C. is often required when curing the resin composition, it is preferable to use one whose 10-hour half-life temperature is 100 to 140° C. Furthermore, one whose 10-hour half-life temperature is 110 to 130° C. is more preferable.

[0174] Examples of the organic peroxide of component (E) include organic peroxides manufactured by NOF Corporation under the trade names "Percumyl D," "Perbutyl C," and "Perbutyl P." Component (E) may be used alone or in combination of two or more types.

[0175] Furthermore, when component (E) is contained, the content of component (E) is preferably 0.1 to 5.0 parts by mass, and more preferably 0.5 to 3.0 parts by mass, per 100 parts by mass of the resin components (components (A), (B), and (C)) in the composition. By configuring in this manner, it is possible to satisfactorily improve heat resistance and adhesiveness.

[0176] [Component (F)] Component (F) is an inorganic filler. The inorganic filler is required to have insulating properties and a low thermal expansion coefficient. A typical inorganic filler can be used as the inorganic filler. Examples of inorganic fillers include silica, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. The inorganic filler may be used alone or in combination of two or more. In particular, silica filler and alumina filler are preferred from the viewpoint of insulating properties. Furthermore, silica filler is preferred from the viewpoint of dielectric properties and thermal expansion coefficient. The inorganic filler may be surface-treated with a silane coupling agent having one or more functional groups selected from acrylic, methacrylic, styryl, amino, epoxy, and vinyl. For example, the heat resistance, moisture resistance, and dispersibility of the inorganic filler can be improved by surface treating it with a surface treatment agent such as an aminosilane coupling agent, a ureidosilane coupling agent, an epoxysilane coupling agent, a mercaptosilane coupling agent, a silane coupling agent, a vinylsilane coupling agent, a styrylsilane coupling agent, an acrylate silane coupling agent, an isocyanate silane coupling agent, a sulfide silane coupling agent, an organosilazane compound, or a titanate coupling agent. These may be used alone or in combination of two or more.

[0177] The shape of the inorganic filler is not particularly limited, and examples include spherical, scaly, needle-like, and amorphous shapes. From the viewpoint of fluidity, spherical shapes are preferred. The average particle diameter is preferably 0.1 to 10 μm, and more preferably 0.1 to 4 μm. When the average particle diameter of the inorganic filler is within this range, excellent embedding properties between fine structures are achieved. The average particle diameter is the particle diameter at 50% of the cumulative value in the particle size distribution on a volume basis, measured by a laser diffraction / scattering method. The average particle diameter can be measured, for example, using a laser scattering diffraction particle size distribution measuring device: LS13320 (manufactured by Beckman Coulter, Inc., wet type).

[0178] When the resin composition contains the (F) component, the (F) component is preferably contained in an amount of 50% by mass or more, more preferably 50 to 90% by mass, and even more preferably 50 to 85% by mass, per 100% by mass of the nonvolatile components in the resin composition. Furthermore, when the content of the (F) component is defined as a ratio to the total amount of the (A), (B), and (C) components, the (F) component is preferably contained in an amount of 200 parts by mass or more, more preferably 200 to 600 parts by mass, and even more preferably 300 to 600 parts by mass, per 100 parts by mass of the total of the (A), (B), and (C) components. This configuration can improve the thermal expansion coefficient.

[0179] [Other Components] The resin composition of this embodiment may further contain components other than the components (A) to (F) described above. Examples of other components include solvents, silane coupling agents, photopolymerization initiators, sensitizers, ion trapping agents, stabilizers, leveling agents, antifoaming agents, foaming agents, flame retardants, colorants (pigments or dyes), reactive diluents, dispersants, surfactants, wetting agents, thixotropic agents, thickeners, plasticizers, mildew inhibitors, rust inhibitors, cationic polymerization initiators, anionic polymerization initiators, conductive particles, and various additives such as organic fillers. Furthermore, in addition to components (A) to (D), the resin composition may further contain other compounds (e.g., other resin components). The content of these other components is not particularly limited as long as it does not impair the effects of the present invention. For example, it is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, even more preferably 1% by mass or less, and particularly preferably 0.1% by mass or less. It is also preferably 0.01% by mass or more. The content is preferably 0.01 to 10 mass %, more preferably 0.01 to 5 mass %, even more preferably 0.01 to 3 mass %, particularly preferably 0.01 to 1 mass %, and most preferably 0.01 to 0.1 mass %.

[0180] [Characteristics of Resin Composition] The resin composition of this embodiment preferably has the following characteristics, for example. The minimum melt viscosity of the resin composition is preferably 500 to 5000 Pa·s. By configuring in this way, the resin composition has extremely good embeddability around substrates and electronic elements.

[0181] When the resin composition does not contain an inorganic filler as component (F), the minimum melt viscosity of the resin composition is more preferably 600 to 4000 Pa s, even more preferably 600 to 3500 Pa s, and particularly preferably 700 to 3000 Pa s. Even when the content of component (F) in 100% by mass of nonvolatile components in the resin composition is less than 50% by mass, the minimum melt viscosity of the resin composition is more preferably 600 to 4000 Pa s, even more preferably 600 to 3500 Pa s, as in the case described above.

[0182] On the other hand, when the content of component (F) in 100% by mass of nonvolatile components in the resin composition is 50% by mass or more, the minimum melt viscosity of the resin composition is more preferably 800 to 4000 Pa s, even more preferably 900 to 3500 Pa s, and particularly preferably 1000 to 3000 Pa s.

[0183] The minimum melting temperature of the resin composition is preferably less than 200°C, more preferably 60°C or higher and lower than 200°C, and even more preferably 80°C or higher and lower than 180°C.

[0184] The minimum melt viscosity (Pa s) and minimum melt temperature (°C) of a resin composition can be measured by the following method. First, a solution containing the resin composition is applied to a release-treated PET film using a knife. The solution on the PET film is then dried at a temperature of 80 to 130°C to produce a resin film with a thickness of 50 to 100 μm. The resin film thus prepared is laminated to a thickness of 300 μm, and the melt viscosity is measured using a rheometer. The minimum melt viscosity and minimum melt temperature at this time are read, and the read values ​​are used as the minimum melt viscosity (Pa s) and minimum melt temperature (°C) of the resin composition. The measurement conditions are as follows: using parallel plates with a diameter of 5 mm, a load of 50 gf, a strain of 1%, a frequency of 1 Hz, and a rate of 5°C / min, and measuring from 50 to 200°C. The solution to be applied to the PET film (solution containing the resin composition) can be prepared by dissolving each component constituting the resin composition in toluene as a solvent. In this case, when the resin composition does not contain an inorganic filler as component (F), the solution is prepared so that the solid content concentration in the solution becomes 30 mass %. On the other hand, when the resin composition contains an inorganic filler as component (F), the solution is prepared by dissolving and dispersing each component so that the solid content concentration in the solution becomes 60 mass %.

[0185] The resin composition of this embodiment preferably has a glass transition temperature (Tg) of 180° C. or higher, more preferably 190 to 250° C., and particularly preferably 200 to 250° C. When the resin composition of this embodiment has a glass transition temperature in the above range, it has the effect of improving heat resistance.

[0186] The resin composition of this embodiment preferably has a coefficient of thermal expansion (CTE) of 10 to 120 ppm / K, more preferably 10 to 100 ppm / K, and particularly preferably 10 to 60 ppm / K. Because the resin composition of this embodiment has a coefficient of thermal expansion within the above range, when the resin composition of this embodiment is applied to a laminate as an interlayer adhesive film, the resin composition expands only slightly, and therefore can maintain adhesion to the adherend.

[0187] [Method for Producing Resin Composition] The resin composition of this embodiment can be produced by a conventional method, for example, by mixing the components described above using a Raikai mixer, a pot mill, a three-roll mill, a rotary mixer, a twin-screw mixer, or the like.

[0188] [Uses of Resin Composition] The resin composition of this embodiment can be suitably used as a resin composition for adhesives or adhesive films used in electronic components. The resin composition of this embodiment can also be suitably used as an insulating adhesive film. Furthermore, an insulating adhesive film using the resin composition of this embodiment can also be suitably used as an interlayer bonding sheet or interlayer adhesive for multilayer wiring boards. In particular, an insulating adhesive film using the resin composition of this embodiment can be suitably used for forming an interlayer insulating layer. Furthermore, an insulating adhesive film using the resin composition of this embodiment can be suitably used for sealing electronic elements. When the resin composition of this embodiment is used for various applications for electronic components, there are no particular restrictions on the electronic components to be bonded, and examples include various printed wiring boards such as ceramic substrates and organic substrates, semiconductor chips, and semiconductor devices.

[0189] The insulating adhesive film using the resin composition of this embodiment is included as a cured product of the resin composition in laminate substrates and semiconductor devices that constitute electronic components, etc. More specifically, adhesive films for interlayer insulation (films used to form interlayer insulating layers), interlayer adhesives, films for sealing electronic elements, etc. that use this insulating adhesive film are included as a cured product of the resin composition in laminate substrates and semiconductor devices that constitute electronic components, etc. For this reason, it is preferable that the laminate substrates and semiconductor devices that constitute electronic components, etc. contain a cured product of the resin composition of this embodiment.

[0190] An insulating adhesive film using the resin composition of this embodiment can be produced, for example, by preparing a resin composition varnish by dissolving or dispersing the resin composition of this embodiment in a solvent, applying the resulting resin composition varnish to a support, removing the solvent by drying or the like to obtain a coating film, and separating the coating film from the support. The support in this case may be the support used to produce the film, or may be a substrate such as a board, metal foil, or prepreg. If the support is a substrate, the film-laminated member can be used as is in the bonding process without separating the coating film from the support.

[0191] Examples of substrates used to produce films include polyester, polytetrafluoroethylene, polyethylene (PE), polypropylene, polymethylpentene, polyvinyl chloride (PVC), polyethylene terephthalate (PET), and polyolefin (PO). The surface of the substrate may or may not be release-treated. When the surface of the substrate is release-treated, the release treatment may be performed with a silicone-based release agent, or with a non-silicone-based release agent. The thickness of the substrate is not particularly limited, but is, for example, 1 μm to 40 μm.

[0192] The contact angle of the support surface with pure water is not particularly limited, but is, for example, 70 to 120°. The 31B tape peel strength of the release-treated surface of the support is not particularly limited, but is, for example, preferably 100 mN / 25 mm or more, more preferably 300 mN / 25 mm or more, even more preferably 500 mN / 25 mm or more, even more preferably 1000 mN / 25 mm or more, even more preferably 1500 mN / 25 mm or more, and particularly preferably 2000 mN / 25 mm or more. The upper limit is 4500 mN / 25 mm (i.e., 4500 mN / 25 mm or less).

[0193] In one embodiment, the film of the present invention can be provided with a protective film on the surface not bonded to the support (i.e., the surface opposite the support). Examples of the protective film include the same protective film as the support used to produce the film. The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to prevent the adhesion of dust and the like to the film surface and scratches.

[0194] The resin composition varnish can be dried by heating, blowing hot air, etc. The drying temperature conditions are not particularly limited, but can be set preferably to 50°C to 150°C, more preferably 60°C to 130°C, and particularly preferably 70°C to 120°C. The drying time varies depending on the thickness of the film and the components contained in the resin composition, but can be, for example, 1 minute to 20 minutes.

[0195] The present film preferably has a thickness of 50 to 200 μm from the viewpoints of solvent drying property during film formation and ease of lamination.

[0196] The film can be cured using a vacuum press or the like. The pressure of the vacuum press may be, for example, preferably 0.05 to 5.0 MPa, more preferably 0.1 to 4.0 MPa. The pressing time is not particularly limited, but may be preferably 30 to 600 minutes, more preferably 45 to 300 minutes, and even more preferably 60 to 240 minutes. The heating temperature may be preferably 80 to 280°C, more preferably 100 to 240°C, and even more preferably 120 to 220°C. In addition, from the viewpoint of suppressing a decrease in radical polymerization efficiency due to oxygen inhibition, the above process is preferably carried out under vacuum or in an oxygen-free atmosphere.

[0197] The resin composition of the present embodiment can also be used as a prepreg using a cured product of the resin composition, or as a high-frequency electronic component having a cured product of the resin composition.

[0198] Furthermore, the resin composition of this embodiment can be dissolved in a solvent and suitably used as a varnish for forming a rewiring layer (a varnish for forming a rewiring layer). In this case, the resin composition of this embodiment can be referred to as a resin composition used to form a rewiring layer (a resin composition for forming a rewiring layer). The rewiring layer is composed of wiring and an insulating material, and the resin composition of this embodiment is used as the insulating material. The rewiring layer will be described below. In recent years, the wiring in wiring structures constituting electronic components such as integrated circuits has become significantly finer. Accordingly, the spacing between external terminals for connecting semiconductor chips including such wiring structures to external wiring has also become extremely narrow. Such electronic components are mounted on printed circuit boards and used. Due to various constraints, the spacing between positions for connecting the external terminals set on the printed circuit board cannot be narrowed below a certain level. For this reason, a rewiring layer is formed on the surface of a semiconductor chip, and external terminals, typically referred to as bumps, are formed on the rewiring layer. The spacing between the bumps is adjusted to match the spacing between connection positions on the printed circuit board, and the bumps and the semiconductor chip are connected by wiring provided in the rewiring layer.

[0199] When forming a rewiring layer, there have been problems with low CTE, chemical resistance, and high adhesion. Furthermore, dielectric properties have been an issue. When a rewiring layer is formed using the resin composition of this embodiment as a varnish for forming a rewiring layer, the above-mentioned problems with dielectric properties can be resolved while maintaining a low CTE, excellent chemical resistance, and high adhesion. The solvent is not particularly limited, but toluene, for example, can be used. Furthermore, when the resin composition of this embodiment is used as a resin composition for forming a rewiring layer, the resin composition does not need to contain a filler.

[0200] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the following examples, parts and % represent parts by mass and % by mass unless otherwise specified.

[0201] (Examples 1 to 5, Comparative Examples 1 to 5) [Sample Preparation] The components were weighed and mixed to the blending ratios (parts by mass) shown in Table 1 below, and then dissolved in toluene as a solvent to prepare solutions containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5. When the resin composition did not contain an inorganic filler as an optional component, the solution was prepared so that the solids concentration in the solution was 30% by mass. On the other hand, when the resin composition contained an inorganic filler as an optional component, the solution was prepared by dissolving and dispersing the components so that the solids concentration in the solution was 60% by mass.

[0202] The raw materials used in preparing the solutions containing the resin compositions in Examples 1 to 5 and Comparative Examples 1 to 5 are as follows.

[0203] [Component (A)] "OPE-2ST-1200" (trade name): manufactured by Mitsubishi Gas Chemical Company, Inc., modified polyphenylene ether resin having a number average molecular weight (Mn) of 1,200 and terminal vinylbenzyl groups (component (A12)). "SA-9000" (trade name): manufactured by SABIC Innovative Plastics, modified polyphenylene ether resin having a number average molecular weight (Mn) of 1,700 and terminal methacrylic groups (component (A11)). "jER828EL" (trade name): manufactured by Mitsubishi Chemical Corporation, liquid bisphenol A epoxy resin (component (A3)).

[0204] [Component (B)] "1,2-SBS-L" (trade name): manufactured by Nippon Soda Co., Ltd., number average molecular weight (Mn) = 4500, styrene-butadiene block copolymer (20% styrene, 30% 1,2 vinyl structure).

[0205] [Component (C)] "L-DAIC" (trade name): diallyl monoalkyl isocyanurate, manufactured by Shikoku Chemicals Corporation.

[0206] [Component (C')] "TAIC" (trade name): triallyl isocyanurate, manufactured by Mitsubishi Chemical Corporation.

[0207] [Optional Components] "Tuftec P1083" (trade name): SBBS (partially hydrogenated styrene-based elastomer), manufactured by Asahi Kasei Corporation. Shown as P1083 in Table 1. "FB-300MDX" (trade name): Silica filler (average particle size 3 μm, vinylsilane treatment), manufactured by Denka Company Limited.

[0208] [Other Components] 0.1 parts by mass of a curing accelerator (trade name: ADEKA Hardener EH-2021, manufactured by ADEKA Corporation) was blended into the solutions other than those of Example 2 and Example 5. 1 part by mass of a silane coupling agent (trade name: KBM-1083, manufactured by Shin-Etsu Chemical Co., Ltd.) was blended into the solutions. 0.5 parts by mass of a peroxide (trade name: Percumyl D, manufactured by NOF Corporation) was blended into the solutions. Note that other components are not listed in Table 1.

[0209] Components (A), (B), (C) and (C') in Table 1 are resin components.

[0210] [Preparation of Resin Film] First, a solution containing the resin composition of Examples 1 to 5 and Comparative Examples 1 to 5 was applied by a knife onto a release-treated PET film. Then, the solution on the PET film was dried at a temperature of 80 to 130°C to prepare a resin film with a substrate having a thickness of 50 to 100 μm.

[0211] The glass transition points (Tg) (°C) of the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5 obtained as described above were measured. The results are shown in Table 1.

[0212] Furthermore, the coefficient of thermal expansion (CTE) (ppm / K) was measured for the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5. The results are shown in Table 1.

[0213] Furthermore, the dielectric constant (Dk) and dielectric loss tangent (Df) were measured for the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5. The results are shown in Table 1.

[0214] Furthermore, the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5 were measured for "minimum melt viscosity (Pa·s)" by the method described below. The results are shown in Table 1.

[0215] Furthermore, the slitting properties were measured for the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5. The results are shown in Table 1.

[0216] Furthermore, the volatility (%) was measured for the resin films containing the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 5. The results are shown in Table 1.

[0217] [Glass transition temperature (Tg) (°C)] The prepared films were laminated to a thickness of 50 to 100 μm and cured at a temperature of 170 to 200°C for 30 to 60 minutes under a pressure of 1 MPa to obtain a cured film. After peeling the cured film from the support, test pieces (10±0.5 mm × 40±1 mm) were cut from the cured film and measured using a DMA7100 manufactured by Hitachi High-Tech Science Corporation (heating rate: 10°C / min, measurement range: 25 to 300°C). The peak temperature of tan δ was read and used as Tg.

[0218] [Coefficient of Thermal Expansion (CTE) (ppm / K)] The prepared resin films were laminated to a thickness of 50 to 100 μm and cured at a temperature of 170 to 200°C for 30 to 60 minutes under a pressure of 1 MPa to prepare a sample for measuring the coefficient of thermal expansion. The prepared sample was measured using a tensile method with a TMA (thermomechanical analyzer), and the average coefficient of thermal expansion from 30 to 80°C was read (i.e., the measured value of the coefficient of thermal expansion). The measurement conditions were a tensile load of 2 gf, annealing at 20°C / min to 230°C, then returning to room temperature, and then measurement at 5°C / min up to 230°C. The measured coefficient of thermal expansion was the coefficient of thermal expansion in the planar direction (i.e., the XY direction).

[0219] [Dielectric constant (Dk) and dielectric loss tangent (Df)] The prepared resin film was cured at 170 to 200°C for 30 to 60 minutes under a pressure of 1 MPa to prepare an evaluation sample. The dielectric constant (Dk) and dielectric loss tangent (Df) of the prepared sample were measured using a dielectric resonator method (SPDR method). In Table 1, when Df is displayed as 1.7, it means that Df is 1.7 × 10 －３ This means that

[0220] [Minimum Melt Viscosity (Pa s)] The prepared resin film was laminated to a thickness of 300 μm, and the melt viscosity was measured using a rheometer. The minimum melt viscosity at that time was read, and the read value was taken as the minimum melt viscosity (Pa s) of the resin composition. The measurement conditions were as follows: parallel plates with a diameter of 10 mm were used, and measurements were made from 50 to 200°C under a load of 50 gf, a strain of 1%, a frequency of 1 Hz, and a rate of 5°C / min. The lower the minimum melt viscosity, the better the embeddability. A minimum melt viscosity of 5000 Pa s or less is acceptable.

[0221] [Slittability] A method for evaluating the slittability of a prepared resin film in a B-stage state will be described using Figures 1 and 2. Figure 1 is a schematic diagram illustrating a method for evaluating the slittability of a resin film, showing the side of the resin film fixed to a fixture and with a blade inserted. Figure 2 is a plan view schematically illustrating the film after cutting when evaluating the slittability of the resin film. Furthermore, Figure 2 is a schematic diagram illustrating the state of the film after cutting as viewed from above, and is a schematic diagram showing an enlarged view of the chipping of the cut portion. The prepared resin film 1 was placed with the substrate 2 side facing up, and both ends of the resin film 1 were fixed with fixtures 3, with the middle portion floating in the air. From the fixed, floating state, a blade 4 was inserted into the resin film 1 from the substrate 2 side, and a cutting speed of 2.5 cm / sec was used to form a 10 cm long cut, and the chipping 5 of the sheet was evaluated. As the blade 4, an "MBB50K (blade thickness: 0.25 mm)" manufactured by Olfa Corporation was used. Observe the cut part of the processed film and check that the area of ​​the film chipping around the cut surface (the area of ​​the part that has been lost due to chipping) is 5 mm ２ A is less than 5mm. ２ More than 50 mm ２ A: Less than 50mm ２ More than 100 mm ２ C: Less than 100mm ２ Those having the above grade were evaluated as D. Regarding the slitting property, A and B are acceptable, and C and D are unacceptable.

[0222] [Volatility (%)] The substrate was peeled from the prepared film, and the masses before and after heating were compared. The heating conditions were 150°C and 60 minutes. Volatility (%) = (mass after heating - mass before heating) / mass before heating x 100, and evaluation was based on the following criteria: A: -0.8% or more, B: -1.0% or more, less than -0.8%, C: -1.5% or more, less than -1.0%, D: less than -1.5%. A and B are acceptable volatility, while C and D are unacceptable volatility.

[0223]

[0224] [Results] As shown in Table 1, the resin compositions of Examples 1 to 5 were superior in slittability in the B-stage state compared to the resin compositions of Comparative Examples 1 and 3. The resin compositions of Examples 1 to 5 contained L-DAIC, whereas the resin composition of Comparative Example 1 did not contain L-DAIC, and the resin composition of Comparative Example 3 contained TAIC instead of L-DAIC.

[0225] Furthermore, Examples 1 to 5 demonstrate that when components (B) and (C) are used in combination, reducing the amount of component (C) can increase the Tg. Furthermore, Examples 1 to 5 and Comparative Examples 2 and 5 demonstrate that the inclusion of component (B) or component (C) reduces the thermal expansion coefficient. Furthermore, the resin composition of Comparative Example 2, due to the absence of component (B), exhibits a high minimum melt viscosity and poor molding fluidity, resulting in poor embeddability. Furthermore, the resin composition of Comparative Example 4 does not contain components (B) or (C) and contains too much component (A12), making it unsuitable for film formation. Furthermore, the resin composition of Comparative Example 5 does not contain components (B) or (C), and contains a high amount of a high-molecular-weight hydrogenated styrene-based elastomer (Tuftec P1083) (molecular weight 50,000 or more), resulting in a high melt viscosity, with the minimum melt viscosity exceeding the upper limit of measurement and making it unmeasurable.

[0226] The resin composition of the present invention can be used as an adhesive for electronic components or as a resin composition for insulating adhesive films. The insulating adhesive film of the present invention can be used for bonding between layers in multilayer wiring boards. The insulating adhesive film of the present invention can be used to seal electronic elements. The laminated substrate of the present invention can be used for electronic components, etc. The electronic components of the present invention can be used for semiconductor devices, etc. The semiconductor device of the present invention can be used for communication electronic devices, etc.

[0227] REFERENCE SIGNS LIST 1 Resin film 2 Base material 3 Fixture 4 Blade 5 Chip

Claims

1. A resin composition comprising: (A) a thermosetting resin; (B) a compound having a butadiene skeleton with 1,2-vinyl groups; and (C) a compound having an isocyanuric ring structure and one or two double bonds at the molecular terminal, wherein the number average molecular weight of component (B) is 1,000 to 10,000.

2. The resin composition according to claim 1, having a minimum melt viscosity of 500 to 5,000.

3. The resin composition according to claim 1 or 2, wherein the component (B) is a compound having a styrene skeleton.

4. The resin composition according to any one of claims 1 to 3, wherein the component (B) is a styrene-butadiene block copolymer.

5. The resin composition according to any one of claims 1 to 4, wherein component (B) is a styrene-butadiene-styrene block copolymer represented by the following structural formula (1), or a hydrogenated product thereof: (In the structural formula (1), m, o, p, and q each independently represent a positive integer, n represents 0 or a positive integer, and the relationship of o:p:q = 1-20:60-98:1-20 is satisfied, and the relationship of m:n = 100:0-80:20 is satisfied.) 6. The resin composition according to any one of claims 1 to 5, wherein the 1,2-vinyl structure in the butadiene skeleton of component (B) is 5 to 95% by mass.

7. The resin composition according to any one of claims 1 to 6, wherein the component (C) is liquid.

8. The resin composition according to any one of claims 1 to 7, wherein component (C) has two allyl groups at the molecular terminals.

9. The resin composition according to any one of claims 1 to 8, wherein the component (C) is a compound represented by the following structural formula (2): (In the structural formula (2), R is an alkyl group having 4 to 14 carbon atoms.) 10. The resin composition according to any one of claims 1 to 9, wherein the component (A) comprises at least one member selected from the group consisting of polyphenylene ether resins, maleimide compounds, and epoxy resins.

11. The resin composition according to any one of claims 1 to 10, wherein the mass ratio of the component (B) to the component (C) is 10:90 to 90:

10.

12. The resin composition according to any one of claims 1 to 11, which is used to form a rewiring layer.

13. An insulating adhesive film made from the resin composition according to any one of claims 1 to 12.

14. The insulating adhesive film according to claim 13, which is used to form an interlayer insulating layer.

15. The insulating adhesive film according to claim 13, which is used to seal electronic elements.

16. A laminated substrate comprising a cured product of the resin composition according to any one of claims 1 to 12 or the insulating adhesive film according to any one of claims 13 to 15.

17. An electronic component comprising the laminate substrate according to claim 16.

18. A semiconductor device comprising the laminated substrate according to claim 16 or the electronic component according to claim 17.

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