Method for producing a photosensitive resin composition

Abstract

Provided is a method for stably producing a photosensitive resin composition that reduces the burden on the environment. [Solution] A method for producing a photosensitive resin composition containing a precursor having formula (1), comprising the steps of activating a carboxylic acid compound represented by formula (2) to obtain an activated carboxylic acid product, and reacting a specific amine compound to obtain a precursor, wherein at least one of the steps of obtaining the activated carboxylic acid product and obtaining a precursor having an amide bond is carried out in a solvent containing a heterocyclic compound having a carbonyl group. TIFF2023022061000022.tif33153 TIFF2023022061000023.tif47153

Description

[Technical Field]

[0001] This invention relates to a method for producing a photosensitive resin composition. [Background technology]

[0002] Conventionally, polyamide resins with specific structures have been preferred as surface protective films and interlayer insulating films for semiconductor devices due to their high heat resistance, electrical properties, and mechanical properties. However, when using such polyamide resins as protective films and interlayer insulating films for semiconductor devices, it has been common practice to dissolve the polyamide resin in an organic solvent and use it in a varnish-like form, from the viewpoint of process efficiency.

[0003] In this regard, the technology disclosed in Patent Document 1 is known. This document discloses a photosensitive resin composition in which a polyimide precursor or polybenzoxazole precursor is combined with a polar solvent having a specific structure. It also discloses that by adjusting the N-methyl-2-pyrrolidone content in the photosensitive resin composition to 0.1% by mass or less, a resin composition that does not gel over time and satisfies the requirements for sensitivity and mechanical properties can be obtained. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Public Gazette No. 2014 / 115233 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] In Patent Document 1, appropriate solvents and other components are selected to reduce the N-methyl-2-pyrrolidone content in the resin composition, from the viewpoint of reducing the burden on the environment. However, in the stage of producing the resin described as Synthesis Example 1 in Patent Document 1, etc., N-methyl-2-pyrrolidone is used as a so-called synthesis solvent. Furthermore, due to these circumstances, an operation to wash the organic layer is performed after the reaction in order to reduce the amount of N-methyl-2-pyrrolidone. Such operations complicate the process, and there are concerns that N-methyl-2-pyrrolidone may remain after scaling up.

[0006] In light of these circumstances, the present invention provides a method for stably obtaining a photosensitive resin composition that reduces the burden on the environment. [Means for solving the problem]

[0007] According to the present invention, A method for producing a photosensitive resin composition comprising a precursor having an amide bond having a repeating unit represented by the following general formula (1), This method is A step of activating a carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activated product, The step of reacting the carboxylic acid activator with an amine compound represented by the following general formula (3) to obtain a precursor having the amide bond, A method for producing a photosensitive resin composition is provided, characterized in that at least one of the steps of obtaining a carboxylic acid activator and obtaining a precursor having an amide bond is carried out in a solvent containing a heterocyclic compound having a carbonyl group.

[0008] [ka] (In general formula (1), X and Y are organic groups. R1 is a hydroxyl group, -O-R3, an alkyl group, an acyloxy group, or a cycloalkyl group, and when there are a plurality of them, they may be the same or different from each other. R2 is a hydroxyl group, a carboxyl group, -O-R3, or -COO-R3, and when there are a plurality of them, they may be the same or different from each other. R3 in R1 and R2 is an organic group having 1 to 15 carbon atoms. When R1 does not have a hydroxyl group, at least one of R2 is a carboxyl group. When R2 does not have a carboxyl group, at least one of R1 is a hydroxyl group. m is an integer from 0 to 8, and n is an integer from 0 to 8.)

[0009] [Chemical formula] (Y, R2, and n in general formula (2) have the same meanings as those shown in general formula (1).)

[0010] [Chemical formula] (X, R, and m in general formula (3) have the same meanings as those shown in general formula (1).) [Advantages of the Invention]

[0011] According to the present invention, a photosensitive resin composition with reduced environmental load can be stably obtained. [Brief Description of the Drawings]

[0012] [Figure 1] It is a cross-sectional view showing an example of an electronic device according to the present embodiment. [Embodiments for Carrying Out the Invention]

[0013] Hereinafter, embodiments will be described with reference to the drawings as appropriate. In all the drawings, the same components are denoted by the same reference numerals, and the description thereof will be omitted as appropriate. Also, "~" represents from above to below unless otherwise specified.

[0014] [Method for Producing Photosensitive Resin Composition] The method for producing the photosensitive resin composition according to this embodiment is as follows. A method for producing a photosensitive resin composition containing a precursor having an amide bond having a repeating unit represented by the following general formula (1), the method includes activating a carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activator; reacting an amine compound represented by the following general formula (3) with the carboxylic acid activator to obtain the precursor having an amide bond, at least one of the step of obtaining a carboxylic acid activator and the step of obtaining a precursor having an amide bond is performed in a solvent containing a heterocyclic compound having a carbonyl group, and is characterized by a method for producing a photosensitive resin composition.

[0015] [Chemical formula] (In general formula (1), X and Y are organic groups. R1 is a hydroxyl group, -O-R3, an alkyl group, an acyloxy group, or a cycloalkyl group, and when there are a plurality of them, they may be the same or different from each other. R2 is a hydroxyl group, a carboxyl group, -O-R3, or -COO-R3, and when there are a plurality of them, they may be the same or different from each other. R3 in R1 and R2 is an organic group having 1 to 15 carbon atoms. When R1 does not have a hydroxyl group, at least one of R2 is a carboxyl group. When R2 does not have a carboxyl group, at least one of R1 is a hydroxyl group. m is an integer from 0 to 8, and n is an integer from 0 to 8.)

[0016] [Chemical formula] (Y, R2, and n in general formula (2) have the same meanings as those shown in general formula (1).)

[0017] [Chemical formula] (In general formula (3), X, R1, and m are equivalent to those shown in general formula (1).)

[0018] (Precursor having an amide bond) First, we will describe the precursor having an amide bond contained in the photosensitive resin composition produced by the manufacturing method of this embodiment.

[0019] The precursor having an amide bond in this embodiment has a structure represented by the general formula (1) above (hereinafter, this precursor is also referred to as "polyamide resin"). In general formula (1), for R1 and R2, groups in which the hydroxyl group and carboxyl group are protected by a protecting group R3 can be used to adjust the solubility of the polyamide resin in an alkaline aqueous solution. Specifically, -O-R3 can be used as R1, and -O-R3 and -COO-R3 can be used as R2. Examples of such organic groups having 1 to 15 carbon atoms as R3 include formyl group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, tertiary butoxycarbonyl group, phenyl group, benzyl group, tetrahydrofuranyl group, and tetrahydropyranyl group.

[0020] The organic group X in the above general formula (1) is not particularly limited, but examples include aromatic groups consisting of structures such as benzene rings, naphthalene rings, and bisphenol structures; heterocyclic organic groups consisting of structures such as pyrrole rings and furan rings; and siloxane groups. More specifically, those represented by the following formula (12) are preferred. These may be used individually or in combination of two or more types as needed.

[0021] [ka] (In formula (12), * indicates bonding to the NH group in general formula (1). Z is an alkylene group, a substituted alkylene group, -O-C6H4-O-, -O-, -S-, -SO2-, -C(=O)-, -NHC(=O)-, or a single bond. R5 represents one selected from alkyl groups, alkyl ester groups, and halogen atoms, which may be the same or different. R6 represents one selected from hydrogen atoms, alkyl groups, alkyl ester groups, and halogen atoms. u is an integer from 0 to 4. R7~R 10 These are either monovalent or divalent organic groups. Note that in formula (12) above, substituent R1 of X in general formula (1) above is omitted.

[0022] Among the groups represented by the above formula (12), those represented by the following formula (13) (which may also have R1 in general formula (1)) are particularly preferred.

[0023] [ka] (In formula (13), * indicates bonding to the NH group in general formula (1). In the formula, Z is an alkylene group, a substituted alkylene group, -O-, -S-, -SO2-, -C(=O)-, -NHC(=O)-, -CH3-, -C(CH3)H-, -C(CH3)2-, -C(CF3)2-, or a single bond. 11 R is one selected from alkyl groups, alkoxy groups, acyloxy groups, and cycloalkyl groups. 11 If there are multiple values, they may be the same or different. v is an integer between 0 and 3 (inclusive).

[0024] Among the groups represented by the above formula (13), those represented by the following formula (14) (which may also have R1 in general formula (1)) are particularly preferred.

[0025] [ka] (In formula (14), * indicates bonding to the NH group in general formula (1). 12 (These are organic groups selected from alkylene groups, substituted alkylene groups, -O-, -S-, -SO2-, -C(=O)-, -NHC(=O)-, -C(CF3)2-, and single bonds.)

[0026] Z in equations (12) and (13) above, and R in equation (14) above. 12 Specific examples of alkylene groups and substituted alkylene groups include -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CH2CH3)-, -C(CH3)(CH2CH3)-, -C(CH2CH3)(CH2CH3)-, -CH(CH2CH2CH3)-, -C(CH3)(CH2CH2CH3)-, -CH(CH(CH3)2)-, -C(CH3)(CH(CH3)2)-, and -CH(CH2C Examples include H2CH2CH3)-, -C(CH3)(CH2CH2CH2CH3)-, -CH(CH2CH(CH3)2)-, -C(CH3)(CH2CH(CH3)2)-, -CH(CH2CH2CH2CH2CH3)-, -C(CH3)(CH2CH2CH2CH2CH3)-, -CH(CH2CH2CH2CH2CH2CH3)-, and -C(CH3)(CH2CH2CH2CH2CH2CH3)-. Among these, -CH2-, -CH(CH3)-, and -C(CH3)2- are preferred because they have sufficient solubility not only in alkaline aqueous solutions but also in solvents, resulting in a more balanced resin film.

[0027] Furthermore, Y in the above general formula (1) is an organic group, and examples of such organic groups are the same as those for X above. For example, aromatic groups consisting of structures such as benzene rings, naphthalene rings, and bisphenol structures; heterocyclic organic groups consisting of structures such as pyrrole rings, pyridine rings, and furan rings; and siloxane groups. More specifically, those represented by the following formula (15) are preferred. These may be used individually or in combination of two or more types.

[0028] [ka] (In formula (15), * indicates bonding to the C=O group in general formula (1). J is -CH2-, -C(CH3)2-, -O-, -S-, -SO2-, -C(=O)-, -NHC(=O)-, -C(CF3)2- or a single bond. R 13 represents one selected from an alkyl group, an alkyl ester group, an alkyl ether group, a benzyl ether group and a halogen atom, and they may be the same or different from each other. R 14 represents one selected from a hydrogen atom, an alkyl group, an alkyl ester group and a halogen atom. w is an integer of 0 or more and 2 or less. R 15 ~R 18 are each a monovalent or divalent organic group. In the above formula (15), the substituent R2 of Y in the above general formula (1) is omitted.)

[0029] Among the groups represented by these formula (15), particularly preferred ones include those represented by the following formula (16) (some having R2 in general formula (1)). [[ID=十七]]Regarding the structure derived from the tetracarboxylic dianhydride in the following formula (16), those in which the positions bonding to the C=O group in general formula (1) are both meta positions and those in which they are both para positions are listed, but a structure containing both a meta position and a para position may also be used.

[0030]

Chemical formula

[0031] [[ID=2十九]]

Chemical formula

[0032]

Chemical formula

[0033] (In formula (16), * indicates bonding to the C=O group in general formula (1). R 19 It should be noted that in the above translation, for the part of "

化

Chemical formula

[0034] In this embodiment, the precursor having the above-mentioned amide bond is produced through the following steps. (Step 1) A step of activating a carboxylic acid compound represented by general formula (2) to obtain a carboxylic acid activated product. (Step 2) A step in which an amine compound represented by general formula (3) is reacted with a carboxylic acid activator to obtain a precursor having an amide bond. In other words, in this embodiment, a carboxylic acid compound represented by general formula (2) is appropriately molecularly transformed and then condensed with an amine compound represented by general formula (3) to obtain a precursor having a desired amide bond.

[0035] [ka] (In general formula (2), Y, R2, and n are equivalent to those shown in general formula (1).)

[0036] [ka] (In general formula (3), X, R1, and m are equivalent to those shown in general formula (1).)

[0037] The following describes each step.

[0038] (Process 1) In this process, a carboxylic acid compound represented by general formula (2) is activated to obtain a carboxylic acid activated product. In other words, in this process, the reactivity of the carboxylic acid compound represented by general formula (2) with the amine compound is improved by activating the carboxyl group present in it.

[0039] One embodiment of this process involves halogenating a carboxylic acid compound represented by general formula (2) to obtain an acid halide. In other words, by subjecting a carboxylic acid compound represented by general formula (2) to one of the following treatments, it is converted into an acid fluoride, acid chloride, acid bromide, or acid iodide. Of these, considering the availability of the reagents used, chlorination treatment can be cited as a preferred embodiment.

[0040] Known reagents can be used when performing the fluorination treatment, such as alkali metal fluorides like fluorine, potassium fluoride, and lithium fluoride, alkaline earth metal fluorides like calcium fluoride, and quaternary ammonium fluorides like tetrabutylammonium fluoride. Known reagents can be used when performing chlorination treatment, such as chlorine, thionyl chloride, oxalyl chloride, and phosphorus trichloride. Known reagents can be used in the bromination treatment, such as bromine and aluminum tribromide. Known reagents can be used when performing the iodination treatment, such as iodine, alkali metal iodides such as potassium iodide, and [bis(trifluoroacetoxy)iodo]benzene. The conditions under which these reagents are used are arbitrary depending on the reagent adopted, but it is preferable to adopt conditions that can convert 90% or more of the carboxylic acid compound represented by general formula (2) into an acid halide.

[0041] Another aspect of step 1 is the reaction of a carboxylic acid compound represented by general formula (2) with a compound having a hydroxyl group to obtain an ester compound.

[0042] As the compound having a hydroxyl group, known alcohol compounds can be used, such as methanol, ethanol, isopropanol, n-butanol, t-butyl alcohol, and n-pentanol. Furthermore, as the compound having this hydroxyl group, for example, 1-hydroxybenzotriazole or a derivative of 1-hydroxybenzotriazole can also be used.

[0043] Furthermore, when obtaining this ester compound, a condensing agent commonly used in ester synthesis, such as dicyclohexylcarbodiimide, can be used. In addition, by adding an acid catalyst such as hydrochloric acid, sulfuric acid, benzenesulfonic acid, or toluenesulfonic acid, and then heating the mixture, the reaction can proceed while removing the water generated from the alcohol compound and carboxylic acid compound, thereby promoting esterification and obtaining the above-mentioned ester compound. The esterification conditions are arbitrary depending on the reagents used, but it is preferable to use conditions that can convert 90% or more of the carboxylic acid compound represented by general formula (2) into an ester compound.

[0044] (Process 2) Next, the carboxylic acid activated product (acid halide or ester compound) obtained in step 1 is reacted with an amine compound represented by general formula (3) to obtain a precursor having an amide bond.

[0045] The temperature and time conditions for conversion to this precursor containing an amide bond can be appropriately set depending on the type of carboxylic acid activator or amine compound. Furthermore, known catalysts can be added as appropriate to accelerate the reaction.

[0046] (solvent) In the method for producing the photosensitive resin composition of this embodiment, at least one of the above steps 1 and 2 is carried out in a solvent containing a heterocyclic compound having a carbonyl group.

[0047] It is presumed that the reactivity of monomer molecules differs between solvents containing heterocyclic compounds with carbonyl groups and solvents consisting of conventional acyclic compounds. Although the details are not yet clear, in the synthesis process of photosensitive resins, an end cap compound of acid anhydride is usually reacted with the terminal amide group to terminate the reaction. In contrast, by using the solvent containing the heterocyclic compound with carbonyl groups of this embodiment, the reaction of the end cap compound of acid anhydride with the terminal amide group can be appropriately controlled, improving the reaction rate at the terminals. Furthermore, when a solvent containing a five-membered heterocycle with a carbonyl group is used, the reactivity between monomer molecules of the photosensitive resin can be similarly controlled appropriately, making it easier to increase the molecular weight. In particular, when a five-membered heterocyclic ring is selected as the heterocyclic compound containing a carbonyl group, these effects are remarkably pronounced.

[0048] Heterocyclic compounds having a carbonyl group have high solubility in precursors having amide bonds and other resin components, and also possess appropriate polarity, which allows the reaction to proceed smoothly in step 1 or step 2 described above. Furthermore, in steps 1 and 2, the same solvent may be used, or different solvents may be used, but from the viewpoint of improving productivity and reaction efficiency, it is preferable to use the same solvent.

[0049] Examples of heterocyclic compounds having a carbonyl group include four-membered rings, five-membered rings, six-membered rings, and seven-membered rings, but five-membered rings are preferred. These heterocyclic compounds having a carbonyl group may be partially substituted with hydrocarbon groups such as methyl, ethyl, and propyl groups. Furthermore, examples of heterocyclic compounds having a carbonyl group include compounds that also contain a nitrogen atom in addition to the heterocyclic compound (hereinafter referred to as "carbonyl group-containing heterocyclic compound (i) having a nitrogen atom"). By using the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom in the photosensitive resin composition of this embodiment, better reactivity can be obtained, and the appropriate solubility can reduce the amount of residue at the opening.

[0050] Furthermore, the heterocycle in the five-membered heterocycle having a carbonyl group described above is preferably one or more selected from furan, pyrrole, imidazole, oxazole, thiazole, and pyrazole, and more preferably one or more selected from pyrrole, imidazole, oxazole, thiazole, and pyrazole from the viewpoint of improving reaction efficiency. In addition, different types of heterocycles may be combined.

[0051] Specifically, examples of furan having a carbonyl group include γ-butyrolactone, examples of pyrrole having a carbonyl group include N-ethyl-2-pyrrolidone, examples of imidazole having a carbonyl group include 1,3-dimethyl-2-imidazolidinone, and examples of oxazole having a carbonyl group include 3-methyl-2-oxazolidone. In particular, N-ethyl-2-pyrrolidone and 3-methyl-2-oxazolidone are examples of the above-mentioned heterocyclic compounds (i) containing a carbonyl group with a nitrogen atom. Furthermore, from the viewpoint of increasing the molecular weight of the photosensitive resin and promoting the reactivity of the photosensitive resin with the end cap, it is preferable to select at least one of γ-butyrolactone or 3-methyl-2-oxazolidone.

[0052] Furthermore, the solvent in this embodiment may be a combination of different types of solvents. For example, heterocyclic compounds having different types of carbonyl groups may be used in combination, or heterocyclic compounds (i) containing different types of nitrogen atoms may be used in combination, or a solvent other than a heterocyclic compound having a carbonyl group may be used.

[0053] In other words, in addition to the heterocyclic compounds having a carbonyl group as described above, compounds commonly used as solvents can also be used in either step 1 or step 2. While known solvents can be used as the solvents in combination, it is preferable to use a heterocyclic compound (ii) that does not have a carbonyl group but contains a nitrogen atom in addition to the heterocyclic ring, and a compound (iii) that has a nitrogen atom and a carbonyl group, from the viewpoint of promoting reactivity and obtaining good solubility. Furthermore, from the viewpoint of maintaining good solubility, for example, the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom may be used in combination with the above-mentioned heterocyclic compound (ii) which does not have a carbonyl group but contains a nitrogen atom in addition to the heterocyclic ring, or the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom may be used in combination with the compound (iii) having both a nitrogen atom and a carbonyl group.

[0054] When mixing solvents, the mixing ratio is preferably 1 to 40 parts by weight, and more preferably 1 to 30 parts by weight, of compounds other than the heterocyclic compound having a carbonyl group in this embodiment, per 100 parts by weight of the heterocyclic compound having a carbonyl group in this embodiment.

[0055] Examples of such compounds include 2,6-lutidine, N,N-dimethylacetamide pyruvate, 3-methoxy-N,N-dimethylpropionamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, methyl pyruvate, and ethyl pyruvate and methyl-3-methoxypropionate.

[0056] Furthermore, in this embodiment, the heterocyclic compound having the carbonyl group described above is used as a solvent in step 1 or step 2, but N-methyl-2-pyrrolidone can be added to this solvent as long as it does not impair the purpose of the invention. The content of N-methyl-2-pyrrolidone is preferably 80% by mass or less, more preferably 60% by mass or less, even more preferably 40% by mass or less, especially preferably 20% by mass or less, and particularly preferably 5% by mass or less, relative to the total solvent. Furthermore, it is particularly preferable that N-methyl-2-pyrrolidone is substantially absent from the solvent. Furthermore, the phrase "substantially absent" is used to exclude instances where N-methyl-2-pyrrolidone is intentionally added to this solvent, but it is permissible in cases where it is unavoidable to avoid contamination with N-methyl-2-pyrrolidone during the manufacturing process.

[0057] In this embodiment, it is preferable to carry out both Step 1 and Step 2 described above in a solvent containing a heterocyclic compound having a carbonyl group. This simplifies the process, and in some cases, it may even be possible to perform both steps 1 and 2 in a single pot.

[0058] In this embodiment, a precursor having an amide bond is obtained after completing step 2 described above. In contrast, a photosensitive resin composition can be obtained by replacing the solvent used in step 2 with another solvent, using the solvent used in step 2 as is, or diluting it separately.

[0059] (Other ingredients) In this embodiment, in addition to the components described above, various other components used as photosensitive resin compositions can be incorporated. For example, components other than the aforementioned precursor having an amide bond can be used in combination as the alkali-soluble resin. Examples of such alkali-soluble resins include phenolic resins, phenolic aralkyl resins, hydroxystyrene resins, methacrylic acid resins, methacrylic acid ester resins, and other acrylic resins, as well as cyclic olefin resins. Furthermore, when the photosensitive resin composition is used as a so-called positive type, it can be formulated with photoacid generators such as photosensitive diazoquinone compounds, diaryliodonium salts, triarylsulfonium salts or sulfonium borate salts, 2-nitrobenzyl ester compounds, N-iminosulfonate compounds, imidosulfonate compounds, 2,6-bis(trichloromethyl)-1,3,5-triazine compounds, or dihydropyridine compounds. In addition, additives such as antioxidants, fillers, surfactants, photopolymerization initiators, end-capturing agents, and sensitizers may be added as needed. The amount of these added is at the discretion of the user.

[0060] (Application) The photosensitive resin composition obtained by this embodiment can form a resin film upon curing. The resulting resin film can constitute a permanent film, such as a protective film, an interlayer film, or a dam material. This makes it possible to improve the durability and other properties of electronic devices that incorporate this resin film as a permanent film.

[0061] Next, an example of an electronic device 100 to which the photosensitive resin composition of this embodiment is applied will be described. The electronic device 100 shown in Figure 1 is, for example, a semiconductor chip. In this case, a semiconductor package can be obtained by mounting the electronic device 100 on a wiring substrate via bumps 52. The electronic device 100 comprises a semiconductor substrate on which semiconductor elements such as transistors are provided, and a multilayer wiring layer provided on the semiconductor substrate (not shown). The uppermost layer of the multilayer wiring layer is provided with an interlayer insulating film 30 and an uppermost wiring 34 provided on the interlayer insulating film 30. The uppermost wiring 34 is made of, for example, Al. A passivation film 32 is also provided on the interlayer insulating film 30 and the uppermost wiring 34. An opening is provided in a part of the passivation film 32 through which the uppermost wiring 34 is exposed.

[0062] A rewiring layer 40 is provided on the passivation film 32. The rewiring layer 40 includes an insulating layer 42 provided on the passivation film 32, rewiring 46 provided on the insulating layer 42, and an insulating layer 44 provided on the insulating layer 42 and the rewiring 46. The insulating layer 42 has openings formed therein that connect to the uppermost wiring 34. The rewiring 46 is formed on the insulating layer 42 and within the openings provided in the insulating layer 42 and is connected to the uppermost wiring 34. The insulating layer 44 has openings that connect to the rewiring 46. In this embodiment, one or more of the passivation film 32, insulating layer 42, and insulating layer 44 can be made of a resin film formed by curing the above-mentioned photosensitive resin composition, for example. In this case, for example, the passivation film 32, insulating layer 42, or insulating layer 44 is formed by exposing a coating film made of a photosensitive resin material to ultraviolet light and developing it, and then heating and curing it.

[0063] Bumps 52 are formed within the openings provided in the insulating layer 44, for example, via a UBM (Under Bump Metallurgy) layer 50. The electronic device 100 is connected to a wiring board or the like via the bumps 52.

[0064] It should be noted that the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention. Examples of reference formats are provided below. 1. A method for producing a photosensitive resin composition comprising a precursor having an amide bond having repeating units represented by the following general formula (1), This method is A step of activating a carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activated product, The step of reacting the carboxylic acid activator with an amine compound represented by the following general formula (3) to obtain a precursor having the amide bond, A method for producing a photosensitive resin composition, characterized in that at least one of the steps of obtaining a carboxylic acid activator and obtaining a precursor having an amide bond is carried out in a solvent containing a heterocyclic compound having a carbonyl group. [ka] / (In general formula (1), X and Y are organic groups. 1 is a hydroxyl group, -OR 3 , alkyl group, acyloxy group, or cycloalkyl group, and if there are multiple, they may be the same or different. 2 These are hydroxyl groups, carboxyl groups, and -OR groups. 3 , or -COO-R 3 And if there are multiple, they may be the same or different. 1 and R 2 In R 3 R is an organic group with 1 to 15 carbon atoms. 1 If there is no hydroxyl group, R 2 At least one of them is a carboxyl group. 2 If there is no carboxyl group, then R 1 At least one of them is a hydroxyl group. m is an integer between 0 and 8, and n is an integer between 0 and 8. [ka] / (Y and R in general formula (2) 2 (where n is equivalent to the value shown in general formula (1).) [ka] / (X and R in general formula (3) 1 , m is equivalent to the one shown in general formula (1). 2. A method for producing the photosensitive resin composition described in 1., The method for producing a photosensitive resin composition, wherein the step of obtaining a carboxylic acid activated product involves halogenating the carboxylic acid compound represented by general formula (2) to obtain an acid halide. 3. A method for producing the photosensitive resin composition described in 2. A method for producing a photosensitive resin composition, wherein the halogenation treatment is a chlorination treatment. 4. A method for producing the photosensitive resin composition described in 1., The method for producing a photosensitive resin composition is to perform the step of obtaining a carboxylic acid activated product by reacting a carboxylic acid compound represented by general formula (2) with a compound having a hydroxyl group to obtain an ester compound. A method for producing the photosensitive resin composition described in 5.4., A method for producing a photosensitive resin composition, wherein the compound having a hydroxyl group is 1-hydroxybenzotriazole or a 1-hydroxybenzotriazole derivative. 6. A method for producing a photosensitive resin composition as described in any one of items 1 to 5, A method for producing a photosensitive resin composition, characterized in that both the step of obtaining a carboxylic acid activator and the step of obtaining a precursor having an amide bond are carried out in a solvent containing the heterocyclic compound having the carbonyl group. 7. A method for producing a photosensitive resin composition as described in any one of 1 to 6, A method for producing a photosensitive resin composition, wherein the heterocycle having a carbonyl group is one or more selected from furan, pyrrole, imidazole, oxazole, thiazole, and pyrazole. [Examples]

[0065] Next, the present invention will be described based on examples, but the present invention is not limited to these examples.

[0066] (Example 1) A precursor containing an amide bond was obtained using solvent 1 in the proportions shown in Table 1, following the procedure described below. Specifically, the procedure is as follows. The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the obtained precursor containing an amide bond were also measured, and the results are shown in Table 1. 258.2 g (1 mole) of diphenyl ether-4,4'-dicarboxylic acid and 270.3 g (2 moles) of 1-hydroxybenzotriazole were dissolved in solvent 1 (1500 g). Then, 412.7 g (2 moles) of dicyclohexylcarbodiimide dissolved in solvent 1 (412 g) was added dropwise over 2 hours while maintaining the internal temperature at 0-5°C. After the addition was complete, the internal temperature was returned to room temperature and the mixture was stirred for a further 12 hours to allow the reaction to proceed. After the reaction was complete, the precipitated dicyclohexylcarbodiurea was removed by filtration, and 4000 g of pure water was added dropwise to the resulting filtrate to precipitate crystals. These crystals were collected by filtration, washed with 8000 ml of isopropyl alcohol, and then vacuum dried to obtain 467 g of the dicarboxylic acid derivative. 40.87 g (0.083 mol) of the obtained dicarboxylic acid derivative and 36.63 g (0.1 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane were placed in a four-necked separable flask equipped with a thermometer, stirrer, raw material inlet, and dry nitrogen gas inlet tube, and solvent 1 (180.8 g) was added to dissolve them. Then, while flowing nitrogen, the temperature was raised to 75°C using an oil bath and the reaction was carried out at 75°C for 12 hours. Next, 5.58 g (0.034 mol) of 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride dissolved in solvent 1 (13.0 g) was added, and after stirring for a further 3 hours, the reaction was cooled to room temperature to terminate. Next, the reaction mixture was filtered, then added to a water / isopropyl alcohol = 1 / 3 solution. The precipitate was filtered and thoroughly washed with water, then dried under vacuum to obtain a precursor having an amide bond with repeating units of general formula (A-1) (a resin that dehydrates and cyclizes when heated at 300-400°C to form a polybenzoxazole).

[0067] The obtained precursor having an amide bond had the following repeating unit (A-1).

[0068] [ka]

[0069] The precursor having an amide bond obtained above was dissolved again in solvent 1, and a photoacid generator was added to obtain a photosensitive resin composition. The amount of photoacid generator was adjusted to 15 parts by mass per 100 parts by mass of the precursor having an amide bond, and the amount of solvent 1 was adjusted to 120 parts by mass per 100 parts by mass of the precursor having an amide bond (A-1).

[0070] (Examples 2-12) A precursor having an amide bond was obtained in the same manner as in Example 1, except that solvent 1 used in Example 1 was replaced with solvents 1 to 6 in the proportions shown in Table 1, and its Mn and Mw were determined, respectively. Furthermore, the same procedure as in Example 1 was performed to obtain a photosensitive resin composition.

[0071] [Table 1]

[0072] Solvents 1-6 are as follows: Solvent 1: N-ethyl-2-pyrrolidone Solvent 2: 3-methyl-2-oxazolidone Solvent 3: 3-Methoxy-N,N-dimethylpropionamide Solvent 4: γ-butyrolactone Solvent 5: 2,6-Lutidine Solvent 6: Dimethyl sulfoxide

[0073] The patternability of each photosensitive resin composition in Examples 1 to 12 was confirmed, and in all cases, good patternability was observed, similar to that of conventionally existing photosensitive resin compositions.

[0074] As shown in this example, a precursor having the desired amide bond was obtained by using a specific solvent. Furthermore, by preparing a photosensitive resin composition using this precursor, it was possible to stably obtain a photosensitive resin composition with reduced environmental impact.

[0075] This application claims priority based on Japanese Patent Application No. 2020-026930, filed on 20 February 2020, and incorporates all of its disclosures herein. [Explanation of Symbols]

[0076] 100 Electronic equipment 30 Interlayer insulating film 32 Passivation membrane 34 Top layer wiring 40 Redistribution layer 42 Insulating layer 44 Insulating layer 46 Rewiring 50 UBM layers 52 Bump

Claims

1. A method for producing a photosensitive resin composition comprising a precursor having an amide bond having a repeating unit represented by the following general formula (1), The precursor having the amide bond is formed by reacting an end cap compound of an acid anhydride with the terminal. This method is A step of activating a carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activated product, The steps include: reacting the carboxylic acid activator with an amine compound represented by the following general formula (3) to obtain a precursor having the amide bond; Includes, A method for producing a photosensitive resin composition, characterized in that the step of obtaining a precursor having an amide bond is carried out in a solvent comprising one or two selected from 3-methyl-2-oxazolidone and γ-butyrolactone, and any dimethyl sulfoxide. 【Chemistry 1】 (In general formula (1), X and Y are organic groups. R １ is a hydroxyl group, -O-R ３ , an alkyl group, an acyloxy group, or a cycloalkyl group, and when there are a plurality of them, they may be the same or different from each other. R ２ is a hydroxyl group, a carboxyl group, -O-R ３ , or -COO-R ３ , and when there are a plurality of them, they may be the same or different from each other. R １ and R ２ in R ３ is an organic group having 1 to 15 carbon atoms. When there is no hydroxyl group as R １ , at least one of R ２ is a carboxyl group. When there is no carboxyl group as R ２ , at least one of R １ is a hydroxyl group. m is an integer of 0 to 8, and n is an integer of 0 to 8.) 【Chemistry 2】 (Y and R in general formula (2)) ２ (where n is equivalent to the value shown in general formula (1).) 【Transformation 3】 (X and R in general formula (3)) １ (where m is equivalent to the one shown in general formula (1).)

2. A method for producing the photosensitive resin composition according to claim 1, The method for producing a photosensitive resin composition involves the step of obtaining a carboxylic acid activated product by subjecting the carboxylic acid compound represented by general formula (2) to a halogenation treatment to obtain an acid halide.

3. A method for producing the photosensitive resin composition according to claim 2, A method for producing a photosensitive resin composition, wherein the halogenation treatment is a chlorination treatment.

4. A method for producing the photosensitive resin composition according to claim 1, The method for producing a photosensitive resin composition is to perform the step of obtaining a carboxylic acid activated product by reacting a carboxylic acid compound represented by general formula (2) with a compound having a hydroxyl group to obtain an ester compound.

5. A method for producing the photosensitive resin composition according to claim 4, A method for producing a photosensitive resin composition, wherein the compound having a hydroxyl group is 1-hydroxybenzotriazole or a 1-hydroxybenzotriazole derivative.

6. A method for producing a photosensitive resin composition according to any one of claims 1 to 5, A method for producing a photosensitive resin composition, characterized in that both the step of obtaining a carboxylic acid activator and the step of obtaining a precursor having an amide bond are carried out in a solvent containing the heterocyclic compound having the carbonyl group.

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