Method for producing a modified maleimide resin solution

Abstract

The present invention provides a method for producing a modified maleimide resin solution in which turbidity and precipitate formation are suppressed, a method for producing a resin composition using the modified maleimide resin solution produced by the said method, a method for producing a prepreg, a method for producing a laminate, a method for producing a resin film, a method for producing a printed circuit board, and a method for producing a semiconductor package. [Solution] A method for producing a modified maleimide resin solution, comprising reacting (A) a maleimide resin, (B) an amine compound having two or more primary amino groups, and (C) a monoamine compound having an acidic substituent in an organic solvent, wherein (A) the maleimide resin contains a maleimide resin having two or more N-substituted maleimide groups (excluding the maleimide resins (a3) ​​and (a4) below) (a1), and one or more selected from the group consisting of a maleimide resin represented by the following general formula (A-1-1) (a2), a maleimide resin represented by the following general formula (A-1-2) (a3), and a maleimide resin represented by the following general formula (A-1-3) (a4), a method for producing a modified maleimide resin solution, a method for producing a resin composition using the modified maleimide resin solution produced by the method, a method for producing a prepreg, a method for producing a laminate, a method for producing a resin film, a method for producing a printed circuit board, and a method for producing a semiconductor package.

Description

[Technical Field]

[0001] This embodiment relates to a method for producing a modified maleimide resin solution, a method for producing a resin composition, a method for producing a prepreg, a method for producing a laminate, a method for producing a resin film, a method for producing a printed circuit board, and a method for producing a semiconductor package. [Background technology]

[0002] Mobile communication devices such as mobile phones, their base station equipment, network infrastructure equipment such as servers and routers, and electronic devices such as large computers are all experiencing increasing speeds and capacities of signals used year after year.

[0003] For printed circuit boards, resin compositions primarily composed of thermosetting resins are commonly used as substrate materials. Maleimide resins are known to exhibit excellent heat resistance and low thermal expansion properties as thermosetting resins. Patent Document 1 describes a thermosetting resin composition comprising (A) a copolymer resin having structural units derived from an aromatic vinyl compound and structural units derived from maleic anhydride, (B) an epoxy-modified polybutadiene having hydroxyl groups, and (C) a maleimide compound. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2017-115020 [Overview of the project] [Problems that the invention aims to solve]

[0005] Patent Document 1 describes (C) maleimide compounds, as preferred examples, as maleimide compounds modified with monoamine compounds and diamine compounds having acidic substituents. A specific example described is a modified maleimide resin solution obtained by pre-reacting 4,4'-diphenylmethanebismaleimide with p-aminophenol and 4,4'-diaminodiphenylmethane in an organic solvent. As described above, modifying the maleimide compound introduces an acidic substituent, which is expected to improve the mechanical strength of the cured resin composition and enhance the solubility of the maleimide compound in solvents. On the other hand, studies by the present inventors have shown that the modified maleimide resin solution obtained by the above reaction is turbid and precipitates occur. From the viewpoint of reducing the steps required to remove turbidity and precipitates from the modified maleimide resin solution and improving the quality of the modified maleimide resin solution, a method for producing a modified maleimide resin solution that suppresses the occurrence of turbidity and precipitates is desired.

[0006] In view of the current situation, this embodiment relates to a method for producing a modified maleimide resin solution in which turbidity and precipitate generation are suppressed, a method for producing a resin composition using the modified maleimide resin solution produced by the method, a method for producing a prepreg, a method for producing a laminate, a method for producing a resin film, a method for producing a printed circuit board, and a method for producing a semiconductor package. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems and have found that the above problems can be solved by the following embodiment. [1](A) Maleimide resin and (B) An amine compound having two or more primary amino groups, (C) A monoamine compound having an acidic substituent, This is a method for producing a modified maleimide resin solution by reacting it in an organic solvent. The (A) maleimide resin is A maleimide resin having two or more N-substituted maleimide groups (excluding the maleimide resins (a3) ​​and (a4) below) (a1), A method for producing a modified maleimide resin solution, comprising: one or more maleimide resins selected from the group consisting of a2 represented by the following general formula (A-1-1), a3 represented by the following general formula (A-1-2), and a4 represented by the following general formula (A-1-3). [ka] (In the formula, X A1 (This is a divalent organic group.) [2] A method for producing the modified maleimide resin solution according to [1] above, wherein the component (a1) is an aromatic bismaleimide resin. [3] X in the above general formula (A-1-1), the above general formula (A-1-2), and the above general formula (A-1-3) A1 A method for producing a modified maleimide resin solution according to [1] or [2] above, wherein the modified maleimide resin is a divalent residue obtained by removing two N-substituted maleimide groups from an aromatic bismaleimide resin. [4] A method for producing a modified maleimide resin solution according to any one of [1] to [3] above, wherein component (B) is one or more selected from the group consisting of aromatic diamine compounds and silicone compounds having two primary amino groups. [5] A method for producing a modified maleimide resin solution according to any one of [1] to [4] above, wherein the reaction is carried out at 50 to 160°C. [6] A method for producing a resin composition using a modified maleimide resin solution produced by any of the methods for producing a modified maleimide resin solution described in [1] to [5] above. [7] A method for producing a prepreg using a resin composition produced by the method for producing a resin composition described in [6] above. [8] A method for producing a resin film using a resin composition produced by the method for producing a resin composition described in [6] above. [9] A method for manufacturing a laminate using a resin composition manufactured by the method for manufacturing a resin composition described in [6] above.

[10] A method for manufacturing a printed circuit board, using a resin composition manufactured by the method for manufacturing a resin composition described in [6] above.

[11] A method for manufacturing a semiconductor package, using a printed circuit board manufactured by the method for manufacturing a printed circuit board described in

[10] above. [Effects of the Invention]

[0008] According to this embodiment, it is possible to provide a method for producing a modified maleimide resin solution in which turbidity and precipitate formation are suppressed, a method for producing a resin composition using the modified maleimide resin solution produced by the method, a method for producing a prepreg, a method for producing a laminate, a method for producing a resin film, a method for producing a printed circuit board, and a method for producing a semiconductor package. [Modes for carrying out the invention]

[0009] In this specification, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. For example, the notation "X~Y" (where X and Y are real numbers) means a range of numbers that are greater than or equal to X and less than or equal to Y. In this specification, the phrase "greater than or equal to X" means X and numbers greater than X. In this specification, the phrase "less than or equal to Y" means Y and numbers less than Y. The lower and upper limits of the numerical ranges described herein may be arbitrarily combined with the lower or upper limits of other numerical ranges. In the numerical ranges described herein, the lower or upper limits of those ranges may be replaced with the values ​​shown in the examples.

[0010] Unless otherwise specified, each component and material exemplified herein may be used alone or in combination of two or more. In this specification, the content of each component in a resin composition means the total amount of multiple substances present in the resin composition, unless otherwise specified, if multiple substances corresponding to each component are present in the resin composition.

[0011] The expression "contains XX" as used herein includes both the meaning of containing XX in a reacted state if XX is capable of reacting, and simply the meaning of containing XX.

[0012] In this specification, "solids" refers to components other than the solvent, and components that are liquid at 25°C are also considered to be solids.

[0013] In this specification, "semi-cured product" is synonymous with a resin composition in the B-stage state as defined in JIS K 6800 (2006), and "cured product" is synonymous with a resin composition in the C-stage state as defined in JIS K 6800 (2006).

[0014] The mechanism of action described herein is speculative and does not limit the mechanism by which the effects of this embodiment are achieved.

[0015] Embodiments that combine any combination of the information described herein are also included.

[0016] [Method for producing modified maleimide resin solution] The method for producing the modified maleimide resin solution of this embodiment is: (A) Maleimide resin and (B) An amine compound having two or more primary amino groups, (C) A monoamine compound having an acidic substituent, A method for producing a modified maleimide resin solution, which involves reacting in an organic solvent, The (A) maleimide resin is A maleimide resin having two or more N-substituted maleimide groups (excluding the maleimide resins (a3) ​​and (a4) below) (a1), One or more selected from the group consisting of maleimide resin (a2) represented by the following general formula (A-1-1), maleimide resin (a3) ​​represented by the following general formula (A-1-2), and maleimide resin (a4) represented by the following general formula (A-1-3), This is a method for producing a modified maleimide resin solution containing [the specified ingredient].

[0017] [ka] (In the formula, X A1 (This is a divalent organic group.)

[0018] In this specification, each component may be abbreviated as component (A), component (B), etc., and other components may also be abbreviated in the same way. Furthermore, the reactions of components (A) to (C) above are sometimes referred to as "pre-reactions."

[0019] The reason why the modified maleimide resin solution obtained by the method for producing the modified maleimide resin solution of this embodiment suppresses turbidity and precipitate formation is not clear, but it is presumed that one reason is that the component (A) used in the method for producing the modified maleimide resin solution of this embodiment contains one or more selected from the group consisting of components (a2), (a3), and (a4), thereby suppressing the formation of solvent-insoluble polymer components.

[0020] <(A) component> Component (A) contains a maleimide resin having two or more N-substituted maleimide groups (excluding the maleimide resins (a3) ​​and (a4) below) (a1), and one or more selected from the group consisting of the maleimide resin represented by the above general formula (A-1-1) (a2), the maleimide resin represented by the above general formula (A-1-2) (a3), and the maleimide resin represented by the above general formula (A-1-3) (a4). Each of the components (a1) to (a4) may be used individually or in combination of two or more.

[0021] Component (a1) is not particularly limited as long as it is a maleimide resin having two or more N-substituted maleimide groups, but it is preferably a maleimide resin represented by the following general formula (A-2).

[0022]

Chem.

[0023] In the following description, the preferred embodiments of X A1 in the general formula (A-1-1), the general formula (A-1-2), the general formula (A-1-3) and the general formula (A-2) are described in the same manner, but X A1 in each of the above formulas may be the same or different. From the viewpoint of ease of production of the component (A), X A1 in the general formula (A-1-1), the general formula (A-1-2), the general formula (A-1-3) and the general formula (A-2) is preferably the same.

[0024] X A1 Examples of the divalent organic group represented by X

[0025]

Chem.

[0026] Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R A1 in the general formula (A-3) include alkyl groups having 1 to 5 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group; alkenyl groups having 2 to 5 carbon atoms; alkynyl groups having 2 to 5 carbon atoms and the like. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be linear or branched. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. In this specification, the halogen atoms represented by the general formulas refer to fluorine, chlorine, bromine, and iodine atoms, and examples are omitted. n in the above general formula (A-3) A1 x is an integer between 0 and 4, preferably between 0 and 2, more preferably 0 or 1, and even more preferably 0. n A1 If is an integer greater than or equal to 2, then multiple R A1 They may be the same or they may be different.

[0027] [ka] (In the formula, R A2 and R A3 Each of these is independently an aliphatic hydrocarbon group or halogen atom having 1 to 5 carbon atoms. A2 n is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond, or a divalent group represented by the following general formula (A-4-1). A2 and n A3 Each of these is an independent integer between 0 and 4. * represents a connection point.

[0028] In the above general formula (A-4), R A2 and R A3 Examples of C1-C5 aliphatic hydrocarbon groups represented by include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; C2-C5 alkenyl groups; and C2-C5 alkynyl groups. The C1-C5 aliphatic hydrocarbon group may be linear or branched.

[0029] X in the above general formula (A-4) A2Examples of alkylene groups with 1 to 5 carbon atoms represented by include the methylene group, 1,2-dimethylene group, 1,3-trimethylene group, 1,4-tetramethylene group, and 1,5-pentamethylene group.

[0030] X in the above general formula (A-4) A2 Examples of alkylidene groups with 2 to 5 carbon atoms represented by include ethylidene, propyridene, isopropylidene, butylidene, isobutylidene, pentylidene, and isopentylidene.

[0031] n in the above general formula (A-4) A2 and n A3 Each of these is an integer between 0 and 4, independently of the others. n A2 or n A3 If is an integer greater than or equal to 2, then multiple R A2 Each or multiple R A3 They may be the same or they may be different.

[0032] X in the above general formula (A-4) A2 The divalent group represented by the general formula (A-4-1) is as follows:

[0033] [ka] (In the formula, R A4 and R A5 Each of these is independently an aliphatic hydrocarbon group or halogen atom having 1 to 5 carbon atoms. A3 This is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. A4 and n A5 Each of these is an independent integer between 0 and 4. * represents a connection point.

[0034] In the above general formula (A-4-1), R A4 and R A5Examples of C1-C5 aliphatic hydrocarbon groups represented by include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; C2-C5 alkenyl groups; and C2-C5 alkynyl groups. The C1-C5 aliphatic hydrocarbon group may be linear or branched.

[0035] X in the above general formula (A-4-1) A3 Examples of alkylene groups with 1 to 5 carbon atoms represented by include the methylene group, 1,2-dimethylene group, 1,3-trimethylene group, 1,4-tetramethylene group, and 1,5-pentamethylene group.

[0036] X in the above general formula (A-4-1) A3 Examples of alkylidene groups with 2 to 5 carbon atoms represented by include ethylidene, propyridene, isopropylidene, butylidene, isobutylidene, pentylidene, and isopentylidene.

[0037] n in the above general formula (A-4-1) A4 and n A5 Each of these is an integer between 0 and 4, preferably between 0 and 2, more preferably 0 or 1, and even more preferably 0. n A4 or n A5 If is an integer greater than or equal to 2, then multiple R A4 Each or multiple R A5 They may be the same or they may be different.

[0038] [ka] (In the formula, n A6 (This is an integer between 0 and 10. * represents a connection point.)

[0039] n in the above general formula (A-5) A6This is preferably an integer between 0 and 5, more preferably an integer between 0 and 4, and even more preferably an integer between 0 and 3.

[0040] [ka] (In the formula, n A7 (The numbers are 0-5. * represents a connection site.)

[0041] [ka] (In the formula, R A6 and R A7 Each of these is independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. A8 (This is an integer between 1 and 8. * represents a connection point.)

[0042] In the above general formula (A-7), R A6 and R A7 Examples of C1-C5 aliphatic hydrocarbon groups represented by include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; C2-C5 alkenyl groups; and C2-C5 alkynyl groups. The C1-C5 aliphatic hydrocarbon group may be linear or branched. n in the above general formula (A-7) A8 n is an integer between 1 and 8, preferably between 1 and 5, more preferably between 1 and 3, and even more preferably 1. A8 If is an integer greater than or equal to 2, then multiple R A6 Each or multiple R A7 They may be the same or they may be different.

[0043] (a1) Examples of component include aromatic bismaleimide resin, aromatic polymaleimide resin, and aliphatic maleimide resin. Among these, aromatic bismaleimide resin is preferred from the viewpoint of conductive adhesion and heat resistance. In this specification, "aromatic maleimide resin" means a compound having an N-substituted maleimide group directly bonded to an aromatic ring. In this specification, "aromatic bismaleimide resin" means a compound having two N-substituted maleimide groups directly bonded to an aromatic ring. Furthermore, in this specification, "aromatic polymaleimide resin" means a compound having three or more N-substituted maleimide groups directly bonded to an aromatic ring. Furthermore, in this specification, "aliphatic maleimide resin" means a compound having an N-substituted maleimide group directly bonded to an aliphatic hydrocarbon.

[0044] Preferred aromatic bismaleimide resins include bis(4-maleimidophenyl)methane, m-phenylenebismaleimide, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 4-methyl-1,3-phenylenebismaleimide, and 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, with bis(4-maleimidophenyl)methane being more preferred.

[0045] One or more maleimide resins selected from the group consisting of the maleimide resin (a2) represented by the above general formula (A-1-1), the maleimide resin (a3) ​​represented by the above general formula (A-1-2), and the maleimide resin (a4) represented by the above general formula (A-1-3) are each X in the formula. A1 However, a compound that is a divalent residue obtained by removing two N-substituted maleimide groups from an aromatic bismaleimide resin is preferred, and X in the formula A1 However, compounds that are divalent residues obtained by removing two N-substituted maleimide groups from bis(4-maleimidophenyl)methane, m-phenylenebismaleimide, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 4-methyl-1,3-phenylenebismaleimide, or 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide are more preferred, and X in the formula A1 However, a compound that is a divalent residue obtained by removing two N-substituted maleimide groups from bis(4-maleimidophenyl)methane is even more preferred. In other words, component (a2) is more preferably a compound represented by the following formula (1), component (a3) ​​is more preferably a compound represented by the following formula (2), and component (a4) is more preferably a compound represented by the following formula (3).

[0046] [ka]

[0047] Components (a2), (a3), and (a4) can be produced by known methods, but may also be included as by-products of component (a1) depending on the production conditions of component (a1).

[0048] (Acid value of component (A)) The acid value of component (A) is preferably 0.1 to 6 mg KOH / g, more preferably 0.2 to 4 mg KOH / g, even more preferably 0.3 to 2 mg KOH / g, and even more preferably 0.5 to 0.8 mg KOH / g. The acid value of component (A) can be measured by the method described in the examples.

[0049] The content of component (a1) in component (A) is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 93% by mass or more, from the viewpoint of heat resistance and mechanical strength of the cured product, and from the viewpoint of further suppressing turbidity and precipitate formation in the modified maleimide resin solution, it is preferably 99.5% by mass or less, more preferably 99.0% by mass or less, and even more preferably 98.0% by mass or less.

[0050] The content of component (a2) in component (A) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, from the viewpoint of further suppressing turbidity and precipitate formation in the modified maleimide resin solution, and preferably 1.0% by mass or less, more preferably 0.6% by mass or less, from the viewpoint of heat resistance and mechanical strength of the cured product.

[0051] The content of component (a3) ​​in component (A) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, from the viewpoint of further suppressing turbidity and precipitate formation in the modified maleimide resin solution, and preferably 1.0% by mass or less, more preferably 0.6% by mass or less, from the viewpoint of heat resistance and mechanical strength of the cured product.

[0052] The content of component (a4) in component (A) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and even more preferably 0.4% by mass or more, from the viewpoint of further suppressing turbidity and precipitate formation in the modified maleimide resin solution, and from the viewpoint of heat resistance and mechanical strength of the cured product, it is preferably 2.0% by mass or less, and more preferably 1.2% by mass or less.

[0053] The total content of one or more components selected from the group consisting of components (a2), (a3), and (a4) in component (A) is preferably 0.3% by mass or more, more preferably 0.6% by mass or more, and even more preferably 0.8% by mass or more, from the viewpoint of further suppressing turbidity and precipitate formation in the modified maleimide resin solution, and preferably 4.0% by mass or less, and more preferably 2.5% by mass or less, from the viewpoint of heat resistance and mechanical strength of the cured product.

[0054] Furthermore, the qualitative determination of the compound species contained in component (A) and the quantitative determination of their content can be performed by reversed-phase liquid chromatography, liquid chromatography-mass spectrometry, and liquid chromatography-tandem mass spectrometry, etc. Specifically, this can be done by the method described in the examples.

[0055] <(B) component> Component (B) is not particularly limited as long as it is an amine compound having two or more primary amino groups. Component (B) may be used alone or in combination of two or more. Component (B) is preferably a compound represented by the following general formula (B-1).

[0056] [ka] (In the formula, X B1 (where * represents a divalent organic group, and * represents a bonding site.)

[0057] X in the above general formula (B-1) B1 It is preferable that the group is a divalent group represented by the following general formula (B-2).

[0058] [ka] (In the formula, R B1 and R B2 Each of these is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a hydroxyl group, or a halogen atom. B2 This refers to an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a fluorenylene group, a single bond, or a divalent group represented by the following general formula (B-2-1) or (B-2-2). B1 and n B2 Each of these is an independent integer between 0 and 4. * represents a connection point.

[0059] [ka] (In the formula, R B3 and R B4 Each of these is independently an aliphatic hydrocarbon group or halogen atom having 1 to 5 carbon atoms. B3 This is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an m-phenylenediisopropylidene group, a p-phenylenediisopropylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. B3 and n B4 Each of these is an independent integer between 0 and 4. * represents a connection point.

[0060] [ka] (In the formula, R B5 X is an aliphatic hydrocarbon group or halogen atom having 1 to 5 carbon atoms. B4 and X B5 Each of these is independently an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond. B5 (This is an integer between 0 and 4. * represents a connection site.)

[0061] In the above general formula (B-2), the above general formula (B-2-1), and the above general formula (B-2-2), R B1 , R B2 , R B3 , R B4 and R B5 Examples of C1-C5 aliphatic hydrocarbon groups represented by include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; C2-C5 alkenyl groups; and C2-C5 alkynyl groups. The C1-C5 aliphatic hydrocarbon group may be linear or branched. The C1-C5 aliphatic hydrocarbon group is preferably a C1-C3 aliphatic hydrocarbon group, more preferably a C1-C3 alkyl group, and even more preferably a methyl or ethyl group.

[0062] X in the above general formula (B-2) B2 , X in the above general formula (B-2-1) B3 Furthermore, X in the above general formula (B-2-2) B4 and X B5 Examples of alkylene groups having 1 to 5 carbon atoms include methylene groups, 1,2-dimethylene groups, 1,3-trimethylene groups, 1,4-tetramethylene groups, and 1,5-pentamethylene groups. Among the alkylene groups having 1 to 5 carbon atoms, alkylene groups having 1 to 3 carbon atoms are preferred, alkylene groups having 1 or 2 carbon atoms are more preferred, and methylene groups are even more preferred.

[0063] X in the above general formula (B-2) B2, X in the general formula (B-2-1) above B3 , and X in the general formula (B-2-2) above B4 and X B5 Examples of the alkylidene group having 2 to 5 carbon atoms represented by include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, an isopentylidene group, and the like. As the alkylidene group having 2 to 5 carbon atoms, an alkylidene group having 2 to 4 carbon atoms is preferable, an alkylidene group having 2 or 3 carbon atoms is more preferable, and an isopropylidene group is even more preferable.

[0064] n in the general formula (B-2) above B1 and n B2 are each independently an integer from 0 to 4, and in each case, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and even more preferably 0 or 2. n B1 or n B2 When is an integer of 2 or more, a plurality of R B1 among themselves or a plurality of R B2 among themselves may each be the same or different. 68> n in the general formula (B-2-1) above B3 and n B4 are each independently an integer from 0 to 4, and in each case, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0. n B3 or n B4 When is an integer of 2 or more, a plurality of R B3 among themselves or a plurality of R B4 among themselves may each be the same or different.

[0066] n in the general formula (B-2-2) above B5 is an integer from 0 to 4, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0. n B5 When is an integer of 2 or more, a plurality of R B5 among themselves may be the same or different.

[0067] X in the above general formula (B-1) B1 This may be a divalent group containing the structure represented by the following general formula (B-3), or it may be a divalent group represented by the following general formula (B-4).

[0068] [ka] (In the formula, R B6 and R B7 Each of these is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, a phenyl group, or a substituted phenyl group. (* indicates a bonding site.)

[0069] [ka] (In the formula, R B6 and R B7 This is the same as the one in the general formula (B-3) above, and R B8 and R B9 Each of these is independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms, a phenyl group, or a substituted phenyl group. B6 and X B7 Each of these is independently a divalent organic group, and n B6 (The integer is between 2 and 100. * represents a connection point.)

[0070] In the above general formulas (B-3) and (B-4), R B6 ~R B9 Examples of C1-C5 aliphatic hydrocarbon groups represented by include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups; C2-C5 alkenyl groups; and C2-C5 alkynyl groups. The C1-C5 aliphatic hydrocarbon group may be linear or branched. C1-C3 aliphatic hydrocarbon groups are preferred, C1-C3 alkyl groups are more preferred, and methyl groups are even more preferred. R B6 ~RB9 Examples of substituents on the phenyl group in the substituted phenyl group represented by include the aliphatic hydrocarbon groups having 1 to 5 carbon atoms as described above.

[0071] X B6 and X B7 Examples of divalent organic groups represented by include alkylene groups, alkenylene groups, alkynylene groups, arylene groups, -O- groups, or divalent linking groups formed by combinations of these. Examples of the alkylene groups mentioned above include alkylene groups having 1 to 10 carbon atoms, such as methylene groups, ethylene groups, and propylene groups. Examples of the above-mentioned alkenylene group include alkenylene groups having 2 to 10 carbon atoms. Examples of the alkynylene group mentioned above include alkynylene groups having 2 to 10 carbon atoms. Examples of the above-mentioned arylene groups include phenylene groups, naphthylene groups, and other arylene groups having 6 to 20 carbon atoms. Among these, X B6 and X B7 Of these, alkylene groups and arylene groups are preferred, with alkylene groups being more preferred.

[0072] n B6 n is an integer between 2 and 100, preferably between 2 and 50, more preferably between 3 and 40, and even more preferably between 5 and 30. B6 If is an integer greater than or equal to 2, then multiple R B6 Each or multiple R B7 They may be the same or they may be different.

[0073] Examples of diamine compounds include 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ketone, 4,4'-diaminobiphenyl, and 3,3'-dimethyl-4,4'- Diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)propane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 1,3-bis(3-aminophenoxy)benzene , 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, 1,3-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 1,4-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisanili Examples include aromatic diamine compounds such as 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline, 3,3'-[1,3-phenylenebis(1-methylethylidene)]bisaniline, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, and 9,9-bis(4-aminophenyl)fluorene; and silicone compounds having two primary amino groups. Among these, aromatic diamine compounds and silicone compounds having two primary amino groups are preferred, and 3,3'-diethyl-4,4'-diaminodiphenylmethane and silicone compounds having two primary amino groups are more preferred. In this specification, "aromatic diamine compound" means a compound having two primary amino groups directly bonded to an aromatic ring.

[0074] The primary amino group equivalent of a silicone compound having two primary amino groups is preferably 300 to 2,000 g / mol, more preferably 400 to 1,500 g / mol, and even more preferably 500 to 1,000 g / mol. A silicone compound having two primary amino groups is preferably a silicone compound having primary amino groups at both ends.

[0075] (B) The mass ratio of the aromatic diamine compound to the silicone compound having two primary amino groups in component (aromatic diamine compound: silicone compound having two primary amino groups) is preferably 10:90 to 80:20, more preferably 20:80 to 60:40, and even more preferably 30:60 to 50:50.

[0076] <(C) component> Component (C) is not particularly limited as long as it is a monoamine compound having an acidic substituent. Component (C) may be used alone or in combination of two or more. (C) The amino group contained in component C is preferably a primary amino group. (C) Examples of acidic substituents on component (C) include hydroxyl groups, carboxyl groups, and sulfonic acid groups. Among these, hydroxyl groups and carboxyl groups are preferred from the viewpoint of solubility and reactivity, and hydroxyl groups are more preferred.

[0077] Component (C) is preferably a compound represented by the following general formula (C-1).

[0078] [ka] (In the formula, R C1 R is an acidic substituent selected from the group consisting of hydroxyl groups, carboxyl groups, and sulfonic acid groups. C2 (where is an alkyl group or halogen atom having 1 to 5 carbon atoms, t is an integer from 1 to 5, u is an integer from 0 to 4, and satisfies 1 ≤ t + u ≤ 5.)

[0079] RC1 From the viewpoint of solubility and reactivity, hydroxyl groups and carboxyl groups are preferred as the acidic substituents, with hydroxyl groups being more preferred. t is an integer from 1 to 5, and is preferably an integer from 1 to 3, more preferably 1 or 2, and even more preferably 1, from the viewpoint of adhesion to copper foil, heat resistance, dielectric properties, glass transition temperature, coefficient of thermal expansion and moldability. When t is an integer of 2 or more, multiple R C1 They may be the same or different. R C2 Examples of C1-C5 alkyl groups represented by include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups. The number of carbon atoms in the alkyl group is preferably 1-3. R C2 Examples of halogen atoms represented include fluorine, chlorine, bromine, and iodine atoms. u is an integer from 0 to 4, and from the viewpoint of adhesion to copper foil, heat resistance, dielectric properties, glass transition temperature, coefficient of thermal expansion and moldability, it is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and particularly preferably 0. When u is an integer of 2 or more, multiple R C2 They may be the same or different. Component (C) is more preferably a monoamine compound represented by the following general formula (C-1') or (C-1'') from the viewpoint of adhesion to copper foil, heat resistance, dielectric properties, glass transition temperature, coefficient of thermal expansion and moldability, and even more preferably a monoamine compound represented by the following general formula (C-1'). However, R in the following general formula (C-1') or (C-1'') C1 , R C2 And u are the same as those in general formula (C-1), and the preferred ones are also the same.

[0080] [ka]

[0081] Examples of component (C) include o-aminophenol, m-aminophenol, p-aminophenol, o-aminobenzoic acid, m-aminobenzoic acid, p-aminobenzoic acid, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 3,5-dihydroxyaniline, and 3,5-dicarboxyaniline. Among these, aminophenols such as o-aminophenol, m-aminophenol, and p-aminophenol are preferred from the viewpoint of solubility and reactivity, and p-aminophenol is more preferred.

[0082] <organic solvents> In the manufacturing method of this embodiment, components (A) to (C) are reacted in an organic solvent. Organic solvents may be used individually or in combination of two or more. Examples of organic solvents include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether-based solvents such as tetrahydrofuran; aromatic hydrocarbon-based solvents such as toluene, xylene, and mesitylene; nitrogen-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents such as dimethyl sulfoxide; and ester-based solvents such as γ-butyrolactone. Among these, alcohol-based solvents are preferred from the viewpoint of solubility of each component, and propylene glycol monomethyl ether is more preferred.

[0083] <Reaction conditions> For the pre-reaction, the above components (A), (B), and (C) and the organic solvent are mixed. The amount of component (B) added when carrying out the pre-reaction is preferably 2 to 60 parts by mass, more preferably 5 to 40 parts by mass, and even more preferably 10 to 20 parts by mass, per 100 parts by mass of component (A), from the viewpoint of the solubility of the modified maleimide resin in the solvent and the heat resistance of the cured product. The amount of component (C) added when carrying out the pre-reaction is preferably 1 to 20 parts by mass, more preferably 2 to 10 parts by mass, and even more preferably 3 to 5 parts by mass, per 100 parts by mass of component (A), from the viewpoint of the heat resistance and mechanical strength of the cured product.

[0084] The equivalent ratio (N-substituted maleimide group / -NH2 group) of the total equivalent of -NH2 groups in components (B) and (C) to the total equivalent of N-substituted maleimide groups (Ta1) in component (A) is preferably 0.05 to 10, more preferably 0.5 to 8, even more preferably 1 to 7, and particularly preferably 3 to 6, from the viewpoint of dielectric properties, heat resistance, flame retardancy, and glass transition temperature.

[0085] The solid content concentration of the reaction solution is preferably 20-80% by mass, more preferably 30-70% by mass, even more preferably 40-65% by mass, and particularly preferably 45-60% by mass. When the solid content concentration of the reaction solution is above the lower limit, a good reaction rate is obtained, and productivity tends to be better. Conversely, when the solid content concentration of the reaction solution is below the upper limit, better solubility is obtained, stirring efficiency is improved, and gelation of the product during the reaction tends to be more suppressed.

[0086] The reaction temperature for the pre-reaction is preferably 50 to 160°C, more preferably 60 to 150°C, and even more preferably 70 to 140°C, from the viewpoint of workability such as reaction rate and suppression of product gelation during the reaction. The reaction time for the pre-reaction is preferably 0.5 to 10 hours, more preferably 1 to 8 hours, and even more preferably 2 to 6 hours, from the viewpoint of productivity and allowing the reaction to proceed sufficiently. However, these reaction conditions can be adjusted as appropriate depending on the type of raw materials used, and are not particularly limited.

[0087] The manufacturing method of this embodiment yields a modified maleimide resin having a structure derived from component (A), a structure derived from component (B), and a structure derived from component (C). Here, the structure derived from component (A), the structure derived from component (B), and the structure derived from component (C) are structures formed by a Michael addition reaction between the N-substituted maleimide group of component (A) and the primary amino group of component (B) or component (C), respectively.

[0088] [Method for producing resin compositions] The method for producing the resin composition of this embodiment is a method for producing a resin composition that uses a modified maleimide resin solution produced by the method for producing the modified maleimide resin solution of this embodiment. Other components used in the method for producing the resin composition of this embodiment, besides the modified maleimide resin solution, include, for example, thermosetting resins other than the modified maleimide resin, curing agents, thermoplastic resins, curing accelerators, inorganic fillers, flame retardants, antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, colorants, lubricants, silane coupling agents, and other optional components such as additives. Each of these components may be used individually or in combination of two or more. The content of each component should be determined appropriately within a range that does not hinder the effects of this embodiment. The resin composition can be manufactured by mixing a modified maleimide resin solution with other components as needed. During this process, each component may be dissolved or dispersed while stirring. The mixing order, temperature, time, and other conditions are not particularly limited and can be arbitrarily set according to the type of raw materials, etc.

[0089] [Prepreg manufacturing method] The method for manufacturing a prepreg according to this embodiment is a method for manufacturing a prepreg that uses a resin composition manufactured by the method for manufacturing a resin composition according to this embodiment. One example of a method for manufacturing the prepreg according to this embodiment is to impregnate or coat a sheet-like fibrous substrate with the resin composition produced by the manufacturing method of this embodiment, and then heat-dry it to create a B-stage.

[0090] As the sheet-like fiber substrate, for example, known sheet-like fiber substrates used in laminates for various electrical insulating materials can be used. Examples of materials for sheet-like fiber substrates include inorganic fibers such as E-glass, D-glass, S-glass, and Q-glass; organic fibers such as polyimide, polyester, and tetrafluoroethylene; and mixtures thereof. These sheet-like fiber substrates can take the form of woven fabrics, nonwoven fabrics, rawhide, chopped strand mats, and surfacing mats, for example.

[0091] The temperature and time for heating and drying after impregnating the sheet-like fibrous substrate with the resin composition are not particularly limited, but from the viewpoint of productivity and appropriately B-stage the resin composition, they can be, for example, 50 to 200°C and 1 to 30 minutes.

[0092] The content of the resin composition in the prepreg obtained by the prepreg manufacturing method of this embodiment is not particularly limited, but from the viewpoint of obtaining better moldability when it is made into a laminate, it is preferably 20 to 90% by mass, more preferably 40 to 85% by mass, and even more preferably 50 to 80% by mass.

[0093] [Method for manufacturing resin film] The resin film manufacturing method of this embodiment is a method for manufacturing a resin film that uses a resin composition manufactured by the resin composition manufacturing method of this embodiment. One example of a method for producing the resin film according to this embodiment is to apply a resin composition produced by the production method of this embodiment, which contains an organic solvent, to a support, and then heat-dry it. Examples of support materials include plastic film, metal foil, and release paper. The temperature and time for heating and drying are not particularly limited, but from the viewpoint of productivity and moderately B-staging the resin composition, they can be set to 50-200°C and 1-30 minutes. The resin film obtained by the resin film manufacturing method of this embodiment is preferably used to form an insulating layer when manufacturing a printed circuit board.

[0094] [Manufacturing method for laminated boards] The method for manufacturing a laminate according to this embodiment is a method for manufacturing a laminate using a resin composition manufactured by the method for manufacturing a resin composition according to this embodiment. Laminates containing metal foil are sometimes referred to as metal-clad laminates.

[0095] One example of a method for manufacturing the laminate according to this embodiment is to place metal foil on one or both sides of the prepreg manufactured by the manufacturing method of this embodiment, and then heat-pressure mold it. Typically, this heat-pressure molding hardens the B-staged prepreg to obtain a laminate. When performing heat and pressure molding, one prepreg sheet may be used, or two or more prepreg sheets may be laminated together. For heat and pressure molding, for example, multi-stage presses, multi-stage vacuum presses, continuous molding machines, autoclave molding machines, etc., can be used. The conditions for heat-pressure molding are not particularly limited, but for example, the temperature can be 100-300°C, the time 10-300 minutes, and the pressure 1.5-5 MPa.

[0096] Examples of metals used in metal foils include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing one or more of these metallic elements.

[0097] [Manufacturing method for printed circuit boards] The method for manufacturing a printed circuit board according to this embodiment is a method for manufacturing a printed circuit board that uses a resin composition manufactured by the method for manufacturing a resin composition according to this embodiment. The method for manufacturing a printed circuit board in this embodiment includes, for example, a method of forming conductor circuits on one or more materials selected from the group consisting of cured prepregs, cured resin films, and laminates manufactured by the manufacturing method of this embodiment, using a known method. Furthermore, a multilayer printed circuit board can also be manufactured by performing a multilayer bonding process as needed. Conductor circuits can be formed by, for example, drilling holes, metal plating, etching metal foil, etc., as appropriate.

[0098] [Manufacturing method for semiconductor package] The semiconductor package manufacturing method of this embodiment is a semiconductor package manufacturing method that uses a printed circuit board manufactured by the printed circuit board manufacturing method of this embodiment. One example of a semiconductor package manufacturing method according to this embodiment is a method of mounting semiconductor chips, memory, etc., on a printed circuit board manufactured by the manufacturing method of this embodiment using a known method. [Examples]

[0099] The embodiment will be described in detail below with reference to examples. However, this embodiment is not limited to the following examples.

[0100] [Method for measuring acid value] The acid value of the maleimide resin used in each example was measured by potentiometric titration using the COM-1750S automatic titrator manufactured by Hiranuma Sangyo Co., Ltd. Specifically, 1.0 g of the maleimide resin to be measured was weighed into a Mighty Vial, 20 mL of N,N-dimethylformamide was added, and the mixture was stirred to dissolve it. Next, 25 mL of a mixed solution of ethanol and toluene in a 1:2 (volume ratio) was added to prepare the solution to be titrated. The acid value was determined by potentiometric titration of this solution using a 0.05 mol / L ethanolic potassium hydroxide solution.

[0101] [Method for producing modified maleimide resin solution] Examples 1-2, Comparative Examples 1-3 In a 1-liter reaction vessel, equipped with a thermometer, stirrer, and moisture meter with reflux condenser, 229.9 g of the maleimide resin shown in Table 1, 24.7 g of 3,3'-diethyl-4,4'-diaminodiphenylmethane, 8.8 g of p-aminophenol, 36.6 g of amino-modified siloxane (manufactured by Momentive Performance Materials Japan LLC, trade name: XF42-C5379, a silicone compound having primary amino groups at both ends, functional group equivalent of primary amino groups: 740 g / mol), and 449.9 g of propylene glycol monomethyl ether were added. The mixture was reacted under reflux at 120°C under a nitrogen atmosphere for 5 hours, after which 100 g of cyclohexane was added to obtain a modified maleimide resin solution.

[0102] The details of maleimide resins 1-5 shown in Table 1 are as follows; all are products sold as bis(4-maleimidephenyl)methane. Maleimide resin 1: Manufactured by Yama▲East▼▲Sei▼Izumi Shin Material Co., Ltd., Acid value: 0.71mgKOH / g Maleimide resin 2: Manufactured by Sichuan Dong Material Technology Collection Group Co., Ltd., acid value: 0.77 mgKOH / g Maleimide resin 3: Manufactured by K.I. Chemicals Co., Ltd., Acid value: 2.15 mg KOH / g Maleimide resin 4: Manufactured by UFC Corporation, acid value: 3.08 mg KOH / g Maleimide resin 5: Manufactured by Yamato Chemical Industries, Ltd., Acid value: 5.18 mg KOH / g

[0103] [Analysis of maleimide resin] For the maleimide resins 1-5 used in each example, reversed-phase liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and liquid chromatography-tandem mass spectrometry (LC-MS / MS) were performed to qualitatively and quantitatively determine the contents. The measurement conditions for each analysis are as follows.

[0104] (HPLC measurement conditions) • Measurement device: High-performance liquid chromatograph "Chromaster" (manufactured by Hitachi High-Tech Corporation) Autosampler: 5280 Pump: 5160 Column oven: 5310 Detector: 5430 (DAD) • Column: "Inertsil ODS-3" (particle size 5 μm, inner diameter 4.6 mm x length 150 mm) (manufactured by GL Sciences Co., Ltd.) Eluent: Acetonitrile / H2O = 30 vol% / 70 vol% (0 min) → Acetonitrile = 100 vol% (30 min) (linear gradient) ·Flow rate: 1.0mL / min Column temperature: 40°C • Sample volume: 1.0 mg / mL

[0105] (Measurement conditions for LC-MS and LC-MS / MS) • LC device: "ACQUITY UPLC" (manufactured by Waters) ·MS device: “SYNAPT G2-S” (manufactured by Waters) • Column: "Unison UK-C18 UP", inner diameter 2mm, length 100mm (manufactured by Imtakt) Column temperature: 40°C Mobile phase A: 5 mM ammonium acetate aqueous solution Mobile phase B: Acetonitrile • %B:30 (0 min) → 100 (10-15 min) ·Flow rate: 0.4mL / min • Detectors: PDA, MS • Detection wavelength: 210nm • Ionization method, polarity: Electrospray ionization (ESI), Pos • Sample injection volume: 0.5 μL

[0106] Next, the compounds detected in maleimide resins 1 and 2 were compared with the compounds detected in maleimide resins 3 to 5, and the compounds detected only in maleimide resins 1 and 2 were identified. As a result, the compounds detected only in maleimide resins 1 and 2 were the compound represented by formula (1) below (corresponding to component (a2)), the compound represented by formula (2) below (corresponding to component (a3)), and the compound represented by formula (3) below (corresponding to component (a4)). In maleimide resin 1, the content of the compound represented by formula (1) below was 0.13% by mass or less, the content of the compound represented by formula (2) below was 0.16% by mass or less, the content of the compound represented by formula (3) below was 0.37% by mass or less, and the content of bis(4-maleimidephenyl)methane was 93.8% by mass. In maleimide resin 2, the content of the compound represented by formula (1) below was 0.5% by mass or less, the content of the compound represented by formula (2) below was 0.5% by mass or less, the content of the compound represented by formula (3) below was 1.0% by mass or less, and the content of bis(4-maleimidephenyl)methane was 94.1% by mass. On the other hand, in maleimide resins 3-5, compounds corresponding to component (a2), component (a3), and component (a4) were not detected.

[0107] [ka]

[0108] [Visual evaluation of modified maleimide resin solution] The modified maleimide resin solutions obtained in each example were placed in glass bottles (capacity 9 ml, outer diameter 2 cm). The turbidity and precipitates of the modified maleimide resin solutions were then evaluated using the following method. The results are shown in Table 1. (1) Turbidity evaluation A piece of copy paper (manufactured by ASKUL Corporation, product name "ASKUL Multi Paper Super White+") with the letters "ABCDEFG" (font: Meiryo UI, size: 6mm vertically) printed in black was attached to a portion of the side of a glass bottle containing a modified maleimide resin solution, with the printed side facing the glass bottle. Nothing was attached to the side of the glass bottle opposite the letters (hereinafter also referred to as the "observation surface"), so that the letters could be observed from the observation surface side through the glass bottle. Next, the glass bottle was placed between the observer and a light source, with the observation surface facing the observer. Then, with the light source shining on, the letters on the paper attached to the glass bottle were visually observed from the observation surface side through the glass bottle containing the modified maleimide resin solution and evaluated according to the following criteria. (Criteria for evaluating turbidity) A: The characters were clearly legible. B: The letters were legible, but not clearly legible. C: The characters could not be deciphered. (2) Evaluation of precipitates The glass bottle containing the above-mentioned modified maleimide resin solution was placed on a flat surface, and a light was shone from the opposite side of the glass bottle from the observation side. The modified maleimide resin solution inside the glass bottle was visually observed, and the amount of suspended precipitate in the modified maleimide resin solution was evaluated according to the following criteria. [Evaluation criteria for precipitates] A: No precipitates were observed, or the amount of precipitates was extremely small. B: The amount of precipitate was small. C: A large amount of precipitate was observed.

[0109] [Table 1]

[0110] The results shown in Table 1 indicate that the modified maleimide resin solutions produced in Examples 1 and 2 of this embodiment showed suppressed turbidity and precipitate formation.

Claims

1. (A) Maleimide resin and (B) An amine compound having two or more primary amino groups, (C) A monoamine compound having an acidic substituent, This is a method for producing a modified maleimide resin solution by reacting it in an organic solvent. The (A) maleimide resin is A maleimide resin having two or more N-substituted maleimide groups (excluding the maleimide resin (a3) ​​and the maleimide resin (a4) described below) (a1), A method for producing a modified maleimide resin solution, comprising one or more maleimide resins selected from the group consisting of a2 represented by the following general formula (A-1-1), a3 represented by the following general formula (A-1-2), and a4 represented by the following general formula (A-1-3). 【Chemistry 1】 (In the formula, X Ａ１ (It is a divalent organic group.)

2. A method for producing a modified maleimide resin solution according to claim 1, wherein the component (a1) is an aromatic bismaleimide resin.

3. X in the above general formula (A-1-1), the above general formula (A-1-2), and the above general formula (A-1-3) Ａ１ The method for producing a modified maleimide resin solution according to claim 1 or 2, wherein the residue is a divalent residue obtained by removing two N-substituted maleimide groups from an aromatic bismaleimide resin.

4. A method for producing a modified maleimide resin solution according to claim 1 or 2, wherein the component (B) is one or more selected from the group consisting of aromatic diamine compounds and silicone compounds having two primary amino groups.

5. A method for producing a modified maleimide resin solution according to claim 1 or 2, wherein the reaction is carried out at 50 to 160°C.

6. A method for producing a resin composition, using a modified maleimide resin solution produced by the method for producing a modified maleimide resin solution described in claim 1 or 2.

7. A method for producing a prepreg, using a resin composition produced by the method for producing a resin composition described in claim 6.

8. A method for producing a resin film, using a resin composition produced by the method for producing a resin composition described in claim 6.

9. A method for manufacturing a laminate, using a resin composition produced by the method for manufacturing a resin composition described in claim 6.

10. A method for manufacturing a printed circuit board, using a resin composition manufactured by the method for manufacturing a resin composition described in claim 6.

11. A method for manufacturing a semiconductor package, using a printed circuit board manufactured by the method for manufacturing a printed circuit board described in claim 10.

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