TW202309150A - Photosensitive resin composition, method for producing electronic device and electronic device - Google Patents

Abstract

A photosensitive resin composition contains: a polyimide (A), which has an imide ring structure; a polyfunctional (meth)acrylate compound (B); a photosensitive agent (C), and a solvent (J). In the photosensitive resin composition, at least the polyimide (A) having an imide ring structure and the polyfunctional (meth)acrylate compound (B) are preferably dissolved in the solvent (J).

Description

Photosensitive resin composition, manufacturing method of electronic device, and electronic device

The invention relates to a photosensitive resin composition and a manufacturing method of an electronic device.

In the electric/electronic field, in order to form a cured film such as an insulating layer, a photosensitive resin composition containing a polyamide resin and/or a polyimide resin may be used. Therefore, studies have been made on photosensitive resin compositions containing polyamide resins and/or polyimide resins.

As an example, Patent Document 1 describes a photosensitive composition containing at least one fully imidized polyimide polymer and having a weight average molecular weight in the range of about 20,000 Daltons to about 70,000 Daltons ; at least one solubility switching compound; at least one photoinitiator; and at least one solvent capable of forming a solution exhibiting a dissolution rate in excess of about 0.15 μm/sec in the case of cyclopentanone as the developer film.

Patent Documents 2 and 3 also describe a photosensitive resin composition containing a polyamide resin and/or a polyimide resin. prior art literature patent documents

[Patent Document 1] International Publication No. 2016/172092 [Patent Document 2] International Publication No. 2007/047384 [Patent Document 3] Japanese Patent Laid-Open No. 2018-070829

[Problem to be Solved by the Invention]

When forming a cured film in an electronic device using a photosensitive resin composition, curing treatment by heat is generally performed. Specifically, first, a photosensitive resin composition is applied on a substrate to form a film, and the film is patterned by exposure or development. Thereafter, a cured film is formed by heat-treating the patterned film. When the cured film is formed by heating as described above, it is preferable to suppress shrinkage of the film by heating. In particular, in recent years, it has been required to form a flat cured film on a substrate having a level difference. However, when the film shrinks significantly, problems such as impairing the flatness of the film may occur.

The present invention has been accomplished in view of such circumstances. One of the objects of the present invention is to provide a photosensitive resin composition capable of forming a cured film with little shrinkage due to heating and good flatness. [Technical means to solve the problem]

The inventors of the present invention have accomplished the inventions provided below, thereby solving the above-mentioned problems.

According to the present invention, a kind of photosensitive resin composition is provided, and it contains: Polyimide (A), having an imide ring structure; Multifunctional (meth)acrylate compound (B); Photosensitizer (C); and solvent (J).

Furthermore, according to the present invention, a method of manufacturing an electronic device is provided, which includes: a film forming step of forming a photosensitive resin film on a substrate using the above photosensitive resin composition; an exposing step of exposing the photosensitive resin film; and In the development step, the exposed photosensitive resin film is developed.

Moreover, according to this invention, the electronic device provided with the cured film of the said photosensitive resin composition is provided. [Effect of Invention]

According to the present invention, there is provided a photosensitive resin composition capable of forming a cured film with little shrinkage due to heating and good flatness.

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. In all the drawings, the same symbols are assigned to the same components, and explanations thereof are appropriately omitted. In order to avoid complications, (i) when there are multiple identical constituent elements in the same drawing, sometimes only one of them is marked with a symbol and not all constituent elements are marked with a symbol, or (ii) especially after Fig. 2 In the figure of , symbols that are the same as those in FIG. 1 may not be relabeled. All drawings are for illustrative purposes only. The shapes, dimensional ratios, and the like of each member in the drawings do not necessarily correspond to actual items.

In this specification, unless otherwise specified, the term "approximately" means a range that includes consideration of manufacturing tolerances, assembly deviations, and the like. In this specification, unless otherwise specified, the expression "X to Y" in the description of the numerical range means X or more and Y or less. For example, "1 to 5% by mass" means "1 to 5% by mass".

In the expression of a group (atomic group) in the present specification, the expression not describing substitution or unsubstituted includes both those having no substituent and those having a substituent. For example, "alkyl" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group). The expression "(meth)acrylic acid" in this specification shows the concept including both acrylic acid and methacrylic acid. The same applies to similar expressions such as "(meth)acrylate". Unless otherwise specified, the term "organic group" in this specification means an atomic group obtained by removing one or more hydrogen atoms from an organic compound. For example, "monovalent organic group" means an atomic group obtained by removing one hydrogen atom from an arbitrary organic compound. The term "electronic device" in this specification is intended to include semiconductor wafers, semiconductor elements, printed wiring boards, circuit display devices, information communication terminals, light-emitting diodes, physical batteries, chemical batteries and other components, devices, The meaning of the final product, etc. to use.

＜Photosensitive resin composition＞ The photosensitive resin composition of this embodiment contains: polyimide (A), which has an imide ring structure; multifunctional (meth)acrylate compound (B); photosensitizer (C); and solvent (J) .

Most conventional polyamide/polyimide-based photosensitive resin compositions contain polyamide before use (before forming a cured film), but do not contain polyimide. That is, conventionally, a film is often formed on a substrate using a photosensitive resin composition containing polyamide, and the film is typically heated to close the rings of polyamide to form polyimide. However, in this case, the film shrinks due to the ring-closing reaction or dehydration accompanying the ring-closing reaction, and it may be difficult to obtain a cured film with good flatness.

On the other hand, the photosensitive resin composition of this embodiment already contains the polyimide (A) which has an imide ring structure before use (before formation of a cured film). Moreover, in this embodiment, the polymerization reaction of a polyfunctional (meth)acrylate compound (B) is used as a hardening mechanism (this polymerization reaction does not involve dehydration in principle). Under these circumstances, by forming a cured film using the photosensitive resin composition of this embodiment, shrinkage|contraction by heating is small and the cured film with favorable flatness can be formed. In particular, a cured film having good flatness can be formed even on a substrate having a level difference.

Moreover, by using the photosensitive resin composition of this embodiment, it becomes easy to form the cured film favorable in heat resistance and mechanical characteristics (for example, tensile elongation). Hardened films in electronic devices often require high heat resistance or good mechanical properties. However, conventionally, if the resin is designed to be rigid to improve heat resistance, the resin may lose its flexibility, resulting in a decrease in mechanical properties. Although the details are unclear, it is considered that in the photosensitive resin composition of this embodiment, the polyfunctional (meth)acrylate compound (B) reacts with the polyimide having an imide ring structure when hardened (polymerized). (A) As a result of complex entanglement, a cured film different from conventional cured films is formed. This "entangled structure of polyimide having a ring structure and polyfunctional (meth)acrylate" is considered to be related to good heat resistance and good mechanical properties.

From the above circumstances, the photosensitive resin composition of this embodiment is preferably used to form an insulating layer in an electronic device.

Components that may be contained in the photosensitive resin composition of the present embodiment, properties, physical properties, and the like of the photosensitive resin composition of the present embodiment will be continuously described.

(Polyimide (A) having an imide ring structure) The photosensitive resin composition of this embodiment contains the polyimide (A) which has an imide ring structure. Hereinafter, the polyimide (A) which has an imide ring structure is also abbreviated as "polyimide (A)". As mentioned above, since the photosensitive resin composition of this embodiment contains the polyimide which has an imide ring structure before hardening, shrinkage by hardening (heating) tends to be small.

When the molar number of the amide group contained in the polyimide (A) is set as IM, and the molar number of the amide group contained in the polyimide (A) is set as AM, by { The imidization rate represented by IM/(IM+AM)}×100 (%) is preferably at least 90%, more preferably at least 95%, and still more preferably at least 98%. In short, the polyimide (A) is preferably a resin having no or a small amount of ring-opened amide structures and a large amount of ring-closed amide structures. By using such a polyimide, shrinkage|contraction by heating can be suppressed further, and the cured film with more favorable flatness can be formed. As an example, the imidization rate can be known from the area of a peak corresponding to an amide group, the area of a peak corresponding to an amide group, or the like in an NMR spectrum. As another example, the imidization rate can be known from the area of the peak corresponding to the amide group or the area of the peak corresponding to the amide group in the infrared absorption spectrum.

The polyimide (A) is preferably a polyimide containing a fluorine atom. According to the knowledge of the present inventors, polyimides containing fluorine atoms tend to have better solubility in organic solvents than polyimides not containing fluorine atoms. Therefore, by using the polyimide containing a fluorine atom, it becomes easy to make the property of a photosensitive resin composition into a varnish shape. The amount (mass ratio) of fluorine atoms in the fluorine atom-containing polyimide is, for example, 1 to 30 mass%, preferably 3 to 28 mass%, more preferably 5 to 25 mass%. Sufficient solubility in an organic solvent is easily obtained by containing a certain amount of fluorine atoms in the polyimide. On the other hand, from the viewpoint of balance with other performances, the amount of fluorine atoms is preferably not too large.

By variously designing the terminal of the polyimide (A), for example, the mechanical properties (tensile elongation, etc.) of the cured product can be further improved.

As an example, it is preferable that the polyimide (A) has a group capable of reacting with an epoxy group at its terminal to form a bond. As such a group, an acid anhydride group, a hydroxyl group, an amino group, a carboxyl group etc. are mentioned.

Preferably, the polyimide (A) has an acid anhydride group at its terminal. In the photosensitive resin composition of this embodiment, an acid anhydride group and an epoxy group are sufficiently easy to form a bond. The acid anhydride group is preferably a group of an acid anhydride skeleton having a ring structure. The "ring structure" here is preferably a 5-membered ring or a 6-membered ring, more preferably a 5-membered ring.

As a supplementary description of the terminal structure, it is preferable that the polyimide (A) does not have a maleimide structure at its terminal.

The polyimide (A) preferably contains a structural unit represented by the following general formula (a).

In general formula (a), X is a divalent organic group, Y is a tetravalent organic group, At least one of X and Y is a group containing a fluorine atom.

The divalent organic group of X and/or the tetravalent organic group of Y preferably have an aromatic ring structure, and more preferably have a benzene ring structure. Thereby, the heat resistance tends to be further improved. From the viewpoint of solubility in organic solvents, both X and Y are preferably groups containing fluorine atoms. The divalent organic group of X and/or the tetravalent organic group of Y preferably have a structure in which 2 to 6 benzene rings are bonded via a single bond or a divalent linking group. Examples of the divalent linking group here include an alkylene group, a fluorinated alkylene group, an ether group, and the like. The alkylene group and the fluorinated alkylene group may be linear or branched. The carbon number of the divalent organic group of X is 6-30, for example. The carbon number of the tetravalent organic group of Y is 6-20, for example. The two imide rings in the general formula (a) are preferably 5-membered rings respectively.

It is further preferable that the polyimide (A) contains a structural unit represented by the following general formula (aa).

In general formula (aa), Y' represents a single bond or an alkylene group, X has the same meaning as X in the general formula (a). The alkylene group of Y' may be linear or branched. Part or all of the hydrogen atoms in the alkylene group of Y' are preferably substituted by fluorine atoms. The carbon number of the alkylene group of Y' is, for example, 1-6, preferably 1-4, more preferably 1-3.

Polyimide (A) can typically be obtained by: (i) first, reacting (polycondensation) diamine and acid dianhydride to synthesize polyamide, (ii) thereafter, making the polyamide Imination (carrying out a ring closure reaction), (iii) introducing a desired functional group into a polymer terminal if necessary. For specific reaction conditions, reference can be made to the Examples described later or the description in Patent Document 1 above.

In the finally obtained polyimide (A), diamine is incorporated into the polymer as the divalent organic group X in the general formula (a). Moreover, the acid dianhydride is incorporated into the polymer as the tetravalent organic group Y in the general formula (a). In the synthesis of the polyimide (A), one or two or more diamines can be used, and one or two or more acid dianhydrides can be used.

Examples of raw material diamines include 3,4'-diaminodiphenyl ether (3,4'-ODA), 4,4'-diamino-2,2'-bis(trifluoromethyl ) biphenyl (TFMB), 3,3',5,5'-tetramethylbenzidine, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 3,3'-diamine 3,3'-dimethylbenzidine, 3,3'-bis(trifluoromethyl)benzidine, 2,2'-bis(p-aminophenyl)hexafluoropropane, bis( Trifluoromethoxy)benzidine (TFMOB), 2,2'-bis(pentafluoroethoxy)benzidine (TFEOB), 2,2'-trifluoromethyl-4,4'-oxydiphenylamine (OBABTF), 2-phenyl-2-trifluoromethyl-bis(p-aminophenyl)methane, 2-phenyl-2-trifluoromethyl-bis(m-aminophenyl)methane, 2, 2'-bis(2-heptafluoroisopropoxy-tetrafluoroethoxy)benzidine (DFPOB), 2,2-bis(m-aminophenyl)hexafluoropropane (6-FmDA), 2,2 -Bis(3-amino-4-methylphenyl)hexafluoropropane, 3,6-bis(trifluoromethyl)-1,4-diaminobenzene (2TFMPDA), 1-(3,5- Diaminophenyl)-2,2-bis(trifluoromethyl)-3,3,4,4,5,5,5-heptafluoropentane, 3,5-diaminotrifluorotoluene (3 ,5-DABTF), 3,5-diamino-5-(pentafluoroethyl)benzene, 3,5-diamino-5-(heptafluoropropyl)benzene, 2,2'-dimethyl Benzidine (DMBZ), 2,2',6,6'-tetramethylbenzidine (TMBZ), 3,6-diamino-9,9-bis(trifluoromethyl)dibenzopyran ( 6FCDAM), 3,6-diamino-9-trifluoromethyl-9-phenyldibenzopyran (3FCDAM), 3,6-diamino-9,9-diphenyldibenzopyran Nam and so on.

Examples of raw acid dianhydrides include pyromeldar acid dianhydride (PMDA), diphenylether-3,3',4,4'-tetracarboxylic dianhydride (ODPA), benzophenone-3 ,3',4,4'-tetracarboxylic dianhydride (BTDA), biphenyl-3,3',4,4'-tetracarboxylic dianhydride (BPDA), diphenylsulfone-3,3', 4,4'-tetracarboxylic dianhydride (DSDA), diphenylmethane-3,3',4,4'-tetracarboxylic dianhydride, 2,2-bis(3,4-phthalic anhydride)propane, 2,2-bis(3,4-phthalic anhydride)-1,1,1,3,3,3-hexafluoropropane (6FDA), etc. Of course, usable acid dianhydrides are not limited thereto. One kind or two or more kinds of acid dianhydrides can be used.

In terms of molar ratio, the usage ratio of diamine and acid dianhydride is basically 1:1. However, in order to obtain a desired terminal structure, one of them may be used too much. Specifically, by using too much diamine, the terminals (both terminals) of the polyimide (A) tend to become amine groups. On the other hand, the terminal (both terminal) of a polyimide (A) becomes an acid anhydride group easily by using acid dianhydride too much. As mentioned above, in this embodiment, it is preferable that polyimide (A) has an acid anhydride group at the terminal. Therefore, in this embodiment, when synthesizing polyimide (A), it is preferable to use acid dianhydride too much.

It is also possible to react a certain reagent with the amine group and/or acid anhydride group at the terminal of the polyimide obtained by polycondensation, so that the polyimide terminal has a desired functional group.

The weight average molecular weight of polyimide (A) is 5000-100000, for example, Preferably it is 7000-75000, More preferably, it is 10000-50000. When the weight average molecular weight of polyimide (A) is large to some extent, sufficient heat resistance of a cured film can be acquired, for example. Moreover, since the weight average molecular weight of polyimide (A) is not too high, it becomes easy to dissolve polyimide (A) in an organic solvent. The weight average molecular weight can usually be determined by the gel permeation chromatography (GPC) method using polystyrene as a standard substance.

(Polyfunctional (meth)acrylate compound (B)) The photosensitive resin composition of this embodiment contains a polyfunctional (meth)acrylate compound (B). Examples of the polyfunctional (meth)acrylate compound (B) include, without particular limitation, those having two or more (meth)acryl groups in one molecule.

From the viewpoint of realizing the above-mentioned "entangled structure of polyimide having a ring structure and polyfunctional (meth)acrylate" or obtaining a hardened and chemically resistant cured film, multifunctional (meth)acrylate ) The acrylate compound (B) is preferably trifunctional or more. There is no upper limit to the number of functional groups of the polyfunctional (meth)acrylate compound (B), and the upper limit of the number of functional groups is, for example, 11 functional groups from the viewpoint of easy availability of raw materials. As a general tendency, when the polyfunctional (meth)acrylate compound (B) with many functional groups ((meth)acryl groups) is used, the chemical resistance of a cured film tends to improve. On the other hand, in the case of using a polyfunctional (meth)acrylate compound (B) with a small number of functional groups ((meth)acryl groups), mechanical properties such as tensile elongation of the cured film tend to be become good.

As an example, it is preferable that the polyfunctional (meth)acrylate compound (B) contains the (meth)acrylate compound (B1) more than seven functional.

As an example, it is preferable that a polyfunctional (meth)acrylate compound (B) contains a 5-6 functional (meth)acrylate compound (B2).

As an example, it is preferable that a polyfunctional (meth)acrylate compound (B) contains a 3-4 functional (meth)acrylate compound (B3).

As an example, the polyfunctional (meth)acrylate compound (B) may contain the compound represented by the following general formula. In the general formula below, R' is a hydrogen atom or a methyl group, n is 0 to 3, and R is a hydrogen atom or a (meth)acryloyl group.

Specific examples of the polyfunctional (meth)acrylate compound (B) include the following. Of course, the polyfunctional (meth)acrylate compound (B) is not limited to this.

Ethylene Glycol Di(meth)acrylate, Trimethylolpropane Tri(meth)acrylate, Ditrimethylolpropane Tetra(meth)acrylate, Neopentylthritol Tri(meth)acrylate, Polyol polyacrylates such as neopentylthritol tetra(meth)acrylate, diperythritol penta(meth)acrylate, dipenteoerythritol hexa(meth)acrylate, bisphenol A di Di(meth)acrylate of glycidyl ether, epoxy acrylates such as di(meth)acrylate of hexanediol diglycidyl ether, etc., by polyisocyanate and (meth)acrylic hydroxyl Amino ester (meth)acrylate obtained from the reaction of hydroxyl-containing (meth)acrylate such as ethyl ester, etc.

ARONIX M-400, ARONIX M-460, ARONIX M-402, ARONIX M-510, ARONIX M-520 (manufactured by TOAGOSEI CO., LTD.), KAYARAD T-1420, KAYARAD DPHA, KAYARAD DPCA20, KAYARAD DPCA30, KAYARAD DPCA60 , KAYARAD DPCA120 (manufactured by Nippon Kayaku Co., Ltd.), Viscoat #230, Viscoat #300, Viscoat #802, Viscoat #2500, Viscoat #1000, Viscoat #1080 (manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.), NK ESTETRA A - Commercially available products such as BPE-10, NK ESTETRA A-GLY-9E, NK ESTETRA A-9550, NK ESTETRA A-DPH (manufactured by SHIN-NAKAMURA CHEMICAL CO, LTD.).

The photosensitive resin composition may contain only one kind of polyfunctional (meth)acrylate compound (B), and may contain two or more kinds of polyfunctional (meth)acrylate compounds (B). In the latter case, it is preferable to use polyfunctional (meth)acrylate compounds (B) having different functional groups in combination. It is considered that by using polyfunctional (meth)acrylate compounds (B) with different numbers of functional groups in combination, a more complex "entangled structure of polyimide having a ring structure and polyfunctional (meth)acrylate" can be formed. , so that better heat resistance or mechanical properties can be obtained. Incidentally, a mixture of (meth)acrylates having different numbers of functional groups also exists in the commercially available polyfunctional (meth)acrylate compound (B).

The amount of the polyfunctional (meth)acrylate compound (B) is, for example, 50 to 200 parts by mass, preferably 60 to 150 parts by mass, more preferably 50 to 150 parts by mass relative to 100 parts by mass of the polyimide (A). parts, more preferably 70 to 120 parts by mass. The usage-amount of a polyfunctional (meth)acrylate compound (B) is not specifically limited, However, One or two or more of each performance can be further improved by suitably adjusting the usage-amount as mentioned above. As described above, in the photosensitive resin composition of this embodiment, it is considered that "an entanglement structure of polyimide having a ring structure and polyfunctional (meth)acrylate" can be formed by curing, and it is considered that by By properly adjusting the amount of multifunctional (meth)acrylate compound (B) relative to polyimide (A), polyimide (A) and multifunctional (meth)acrylate compound (B) will Entanglement is sufficient, and additional components not related to entanglement are reduced, and as a result, the performance is further improved.

(Photosensitizer (C)) The photosensitive resin composition of this embodiment contains a photosensitizer (C). The photosensitizer (C) is not particularly limited as long as it can harden the photosensitive resin composition by generating an active species by light.

The photosensitizer (C) preferably contains a photoradical generator. A photoradical generator is effective especially when polymerizing a polyfunctional (meth)acrylate compound (B).

啉基丙-1-酮、2-苄基-2-二甲基胺基-1-（4-

啉基苯基）-丁酮-1、2-（二甲基胺基）-2-〔（4-甲基苯基）甲基〕-1-〔4-（4-

啉基）苯基〕-1-丁酮等的烷基苯酮系化合物；二苯甲酮、4,4’-雙（二甲基胺基）二苯甲酮、2-羧基二苯甲酮等的二苯甲酮系化合物；安息香甲基醚、安息香乙基醚、安息香異丙基醚、安息香異丁基醚等的安息香系化合物；9-氧硫

、2-乙基-9-氧硫

、2-異丙基-9-氧硫

、2-氯-9-氧硫

、2,4-二甲基-9-氧硫

、2,4-二乙基-9-氧硫

等的9-氧硫

系化合物；2-（4-甲氧基苯基）-4,6-雙（三氯甲基）-對稱三

、2-（4-甲氧基萘基）-4,6-雙（三氯甲基）-對稱三

、2-（4-乙氧基萘基）-4,6-雙（三氯甲基）-對稱三

、2-（4-乙氧基羰基萘基）-4,6-雙（三氯甲基）-對稱三

等的鹵甲基化三

系化合物；2-三氯甲基-5-（2’-苯并呋喃基）-1,3,4-

二唑、2-三氯甲基-5-〔β-（2’-苯并呋喃基）乙烯基〕-1,3,4-

二唑、4-

二唑、2-三氯甲基-5-呋喃基-1,3,4-

二唑等的鹵甲基化

二唑系化合物；2,2’-雙（2-氯苯基）-4,4’,5,5’-四苯基-1,2’-聯咪唑、2,2’-雙（2,4-二氯苯基）-4,4’,5,5’-四苯基-1,2’-聯咪唑、2,2’-雙（2,4,6-三氯苯基）-4,4’,5,5’-四苯基-1,2’-聯咪唑等的聯咪唑系化合物；1,2-辛二酮,1-〔4-（苯基硫基）苯基〕-2-（鄰苯甲醯基肟）、乙酮,1-〔9-乙基-6-（2-甲基苯甲醯基）-9H-咔唑-3-基〕-,1-（鄰乙醯基肟）等的肟酯系化合物；雙（η5-2,4-環戊二烯-1-基）-雙（2,6-二氟-3-（1H-吡咯-1-基）-苯基）鈦等的環戊二烯鈦系化合物；p-二甲基胺基安息香酸、p-二乙基胺基安息香酸等的安息香酸酯系化合物；9-苯基吖啶等的吖啶系化合物；等。其中，尤其可以較佳地使用肟酯系化合物。 The usable photoradical generator is not particularly limited, and known ones can be used appropriately. Examples include: 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexylphenone, 2-hydroxy-2-methyl -1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4-[4-(2-Hydroxy-2-methylpropionyl)benzyl]phenyl}-2-methylpropan-1-one, 2-methyl-1-(4-methylthio Phenyl)-2-

Linyl propan-1-one, 2-benzyl-2-dimethylamino-1-(4-

Linylphenyl)-butanone-1,2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-

Alkyl phenone compounds such as phenyl)phenyl]-1-butanone; benzophenone, 4,4'-bis(dimethylamino)benzophenone, 2-carboxybenzophenone Benzoin-based compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and other benzoin-based compounds; 9-oxysulfur

, 2-Ethyl-9-oxosulfur

, 2-isopropyl-9-oxosulfur

, 2-Chloro-9-oxosulfur

, 2,4-Dimethyl-9-oxosulfur

, 2,4-Diethyl-9-oxosulfur

9-oxosulfur

Department of compounds; 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-symmetric three

, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-symmetric tri

, 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-symmetric tri

, 2-(4-ethoxycarbonylnaphthyl)-4,6-bis(trichloromethyl)-symmetric tri

halomethylation tri

series compounds; 2-trichloromethyl-5-(2'-benzofuryl)-1,3,4-

Oxadiazole, 2-trichloromethyl-5-[β-(2'-benzofuryl)ethenyl]-1,3,4-

Oxadiazole, 4-

Oxadiazole, 2-trichloromethyl-5-furyl-1,3,4-

Halomethylation of oxadiazoles, etc.

Oxadiazole compounds; 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2, 4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl)-4 ,4',5,5'-tetraphenyl-1,2'-biimidazole and other biimidazole compounds; 1,2-octanedione, 1-[4-(phenylthio)phenyl]- 2-(o-benzoyl oxime), ethyl ketone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(o- Acetyl oxime) and other oxime ester compounds; bis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl) Cyclopentadiene titanium-based compounds such as -phenyl)titanium; benzoate-based compounds such as p-dimethylaminobenzoic acid and p-diethylaminobenzoic acid; 9-phenylacridine, etc. Acridine compounds; etc. Among these, oxime ester-based compounds can be used particularly preferably.

The photosensitive resin composition may contain one kind of photosensitizer (C), or may contain two or more kinds of photosensitizers (C). The usage-amount of a photosensitizer (C) is 1-30 mass parts, for example with respect to 100 mass parts of polyfunctional (meth)acrylate compounds (B), Preferably it is 5-20 mass parts.

(Thermal radical initiator (D)) It is preferable that the photosensitive resin composition of this embodiment contains a thermal radical initiator (D). By using the thermal radical initiator (D), for example, the heat resistance of a cured film and/or the chemical resistance (resistance with respect to an organic solvent etc.) of a cured film can be improved further. This is considered to be because the polymerization reaction of the polyfunctional (meth)acrylate compound (B) can be further accelerated by using a thermal radical initiator (D).

The thermal radical initiator (D) preferably contains an organic peroxide. Examples of organic peroxides include octyl peroxide, lauryl peroxide, stearyl peroxide, 1,1,3,3-tetramethylbutylperoxy 2-ethylhexanoic acid ester, oxalate peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexylperoxy)hexane, 1-cyclohexyl-1-methylethylperoxy 2-ethyl Ethylhexanoate, tertiary hexyl peroxy 2-ethylhexanoate, tertiary butyl peroxy 2-ethylhexanoate, m-toluyl peroxide, benzoyl peroxide, formazan Ethyl ethyl ketone peroxide, acetyl peroxide, tertiary butyl hydroperoxide, di-tertiary butyl peroxide, cumene hydroperoxide, dicumyl peroxide , Tertiary butyl perbenzoate, p-chlorobenzoyl peroxide, cyclohexanone peroxide, etc.

In the case of using a thermal radical initiator (D), only one kind of thermal radical initiator (D) may be used, or two or more thermal radical initiators (D) may be used. When using a thermal radical initiator (D), the amount is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the polyfunctional (meth)acrylate compound (B). share.

(Epoxy resin (E)) It is preferable that the photosensitive resin composition of this embodiment contains an epoxy resin (E). Although the details are unclear, it is considered that the epoxy resin (E) reacts (forms a bond) with the polyimide (A), for example. Also, it may be that the mechanical properties (tensile elongation, etc.) of the cured film tend to be further improved by the flexibility of the ether structure formed by the reaction.

As the epoxy resin (E), any compound having one or more (preferably two or more) epoxy groups in one molecule can be suitably used. Specific examples of the epoxy resin (E) include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol M type epoxy resin (4,4'-(1,3-phenylenediisopropylidene) bisphenol type epoxy resin), bisphenol P type epoxy resin (4 ,4'-(1,4-phenylene diisopropylidene) bisphenol type epoxy resin), bisphenol Z type epoxy resin (4,4'-cyclohexylene bisphenol type epoxy resin), Bisphenol-type epoxy resins such as tetramethylbisphenol F-type epoxy resins; phenol novolak-type epoxy resins, brominated phenol novolak-type epoxy resins, cresol novolak-type epoxy resins, Novolac epoxy resins such as alkane novolac epoxy resins, novolac epoxy resins with condensed ring aromatic hydrocarbon structures, biphenyl epoxy resins, xylylene epoxy resins, Aralkyl type epoxy resins such as biphenyl aralkyl type epoxy resins; naphthyl ether type epoxy resins, naphthol type epoxy resins, naphthalene type epoxy resins, naphthalene diol type epoxy resins Epoxy resins with a naphthalene skeleton such as epoxy resins, 2-4 functional epoxy naphthalene resins, binaphthyl epoxy resins, naphthalene aralkyl epoxy resins; anthracene epoxy resins; phenoxy epoxy resins Resin; dicyclopentadiene type epoxy resin; norcamphene type epoxy resin; adamantane type epoxy resin; Epoxy resin, bisphenol A novolak type epoxy resin, xylenol type epoxy resin, trishydroxyphenylmethane type epoxy resin, stilbene type epoxy resin, tetraphenylol ethane type epoxy resin Resin, heterocyclic epoxy resin such as triglycidyl isocyanate; Glycidylamines or glycidyl (meth)acrylates such as '-tetraglycidylbisaminomethylcyclohexane, N,N-diglycidylaniline, etc. Copolymers of compounds with saturated double bonds; Epoxy resins with butadiene structure; Diglycidyl ethers of bisphenols; Diglycidyl ethers of naphthalene diol; Glycidyl ethers of phenols compounds etc. In addition, as epoxy resins, n-butyl glycidyl ether, 2-ethoxyhexyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, ethyl glycidyl ether, Diol Diglycidyl Ether, Propylene Glycol Diglycidyl Ether, Neopentyl Glycol Diglycidyl Ether, Glycerol Polyglycidyl Ether, Sorbitol Polyglycidyl Ether, Bisphenol Glycidyl ethers such as glycidyl ethers of A (or F), glycidyl ethers such as glycidyl ethers of adipate, glycidyl esters of glycidyl phthalates, etc., 3,4-cyclo Oxycyclohexylmethyl (3,4-epoxycyclohexane) carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl (3,4-epoxy-6-methylcyclohexane ) carboxylate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, dicyclopentadiene oxide, bis(2,3-epoxycyclopentyl)ether or Cycloaliphatic epoxy resins such as CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, CELLOXIDE 8000, EPOLEAD GT401 manufactured by Daicel Corporation, 2,2'-(((((1-(4-(2-(4 -(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenyl)ethan-1,1-diyl)bis(4,1-phenylene))bis(oxylylene )) Bis(methylene)) Bis(oxirane)) (for example, Techmore VG3101L manufactured by Printec Corporation), EPOLIGHT 100MF (manufactured by Kyoeisha Chemical Co., Ltd.), EPIOL TMP (manufactured by NOF CORPORATION), etc. Aliphatic polyglycidyl ether, 1,1,3,3,5,5-hexamethyl-1,5-bis(3-(oxiran-2-ylmethoxy)propyl)trisil Oxane (for example, DMS-E09 (manufactured by GELEST, INC.)) and the like.

As an epoxy resin, what has 2-4 epoxy groups in 1 molecule is preferable, and what has 2-3 epoxy groups in 1 molecule is more preferable. By adjusting the functional groups of the epoxy resin, for example, it is easy to improve the heat resistance of the cured film or the mechanical properties of the cured film in a balanced manner. From another viewpoint, as an epoxy resin, what has an aromatic ring structure and/or an alicyclic structure is preferable. In particular, it is preferable to use such an epoxy resin from the viewpoint of heat resistance.

When using an epoxy resin (E), only 1 type of epoxy resin may be used, and 2 or more types of epoxy resins may be used together. When using the epoxy resin (E), the amount thereof is, for example, 0.5 to 30 parts by mass, preferably 1 to 20 parts by mass, more preferably 3 to 15 parts by mass, based on 100 parts by mass of the polyimide (A). parts by mass.

(hardening catalyst (F)) It is preferable that the photosensitive resin composition of this embodiment contains a hardening catalyst (F). This curing catalyst (F) has the effect of accelerating the reaction of the epoxy resin (E). By using the curing catalyst (F), the reaction in which the epoxy resin (E) participates can be sufficiently advanced to further increase, for example, the tensile elongation of the cured film.

Examples of the curing catalyst (F) include compounds known as curing catalysts for epoxy resins (generally, also referred to as curing accelerators). For example, diacricycloalkene such as 1,8-diacribicyclo[5,4,0]undecene-7 and its derivatives; amine compounds such as tributylamine and benzyldimethylamine ; imidazole compounds such as 2-methylimidazole; organic phosphines such as triphenylphosphine and methyldiphenylphosphine; tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetrabenzoate borate, tetraphenylphosphonium tetranaphthoate borate Four-substituted phosphonium salts such as tetraphenylphosphonium tetranaphthyloxy borate, tetraphenylphosphonium tetranaphthyloxy borate, tetraphenylphosphonium 4,4'-sulfonyl diphenolate, etc.; Triphenylphosphine with benzoquinone added. Among them, organic phosphines are preferably used.

When using a hardening catalyst (F), the amount is 1-80 mass parts with respect to 100 mass parts of epoxy resins (E), for example, Preferably it is 5-50 mass parts, More preferably, it is 5-30 mass parts .

(Silane coupling agent (G)) It is preferable that the photosensitive resin composition of this embodiment contains a silane coupling agent (G). By using the silane coupling agent (G), for example, the adhesiveness between a board|substrate and a cured film can be improved further.

As the silane coupling agent (G), for example, an amino group-containing silane coupling agent, an epoxy group-containing silane coupling agent, a (meth)acryl group-containing silane coupling agent, a mercapto group-containing silane coupling agent, a vinyl silane coupling agents containing urea groups, silane coupling agents containing thioether groups, silane coupling agents with cyclic anhydride structures, etc.

Examples of amino group-containing silane coupling agents include bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, Propyltrimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropyl Trimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, N -β(aminoethyl)γ-aminopropylmethyldiethoxysilane, N-phenyl-γ-amino-propyltrimethoxysilane, etc. As epoxy group-containing silane coupling agents, for example, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β-(3, 4-Epoxycyclohexyl)ethyltrimethoxysilane, γ-epoxypropylpropyltrimethoxysilane, etc. Examples of (meth)acrylyl group-containing silane coupling agents include γ-((meth)acryloxypropyl)trimethoxysilane, γ-((meth)acryloxypropyl) ) Methyldimethoxysilane, γ-((meth)acryloxypropyl)methyldiethoxysilane, etc. As a mercapto group-containing silane coupling agent, 3-mercaptopropyltrimethoxysilane etc. are mentioned, for example. Examples of the vinyl group-containing silane coupling agent include vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, and vinyltrimethoxysilane. As a ureido group containing silane coupling agent, 3-ureidopropyltriethoxysilane etc. are mentioned, for example. Examples of thioether group-containing silane coupling agents include bis(3-(triethoxysilyl)propyl)disulfide, bis(3-(triethoxysilyl)propyl)tetrasulfide things etc. Examples of silane coupling agents having a cyclic anhydride structure include 3-trimethoxysilylpropyl succinic anhydride, 3-triethoxysilylpropyl succinic anhydride, 3-dimethylmethoxysilyl Propyl succinic anhydride, etc.

In this embodiment, it is particularly preferable to use a silane coupling agent having a cyclic acid anhydride structure. Although the details are unclear, it is presumed that the cyclic acid anhydride structure easily reacts with the main chain, side chain, and/or terminal of the polyimide (A), so that a particularly good adhesion-improving effect can be obtained.

In the case of using the silane coupling agent (G), it may be used alone, or two or more types of adhesion aids may be used in combination. In the case of using a silane coupling agent (G), when the amount of polyimide (A) used is 100 parts by mass, the amount used is, for example, 0.1 to 20 parts by mass, preferably 0.3 to 15 parts by mass , more preferably 0.4 to 12 parts by mass, further preferably 0.5 to 10 parts by mass.

(Surfactant (H)) It is preferable that the photosensitive resin composition of this embodiment contains a surfactant (H). Thereby, the applicability of a photosensitive resin composition and the flatness of a film can be further improved. Examples of the surfactant (H) include fluorine-based surfactants, silicone-based surfactants, alkyl-based surfactants, acrylic-based surfactants, and the like. From another viewpoint, it is preferable that the surfactant is nonionic. It is preferable to use a nonionic surfactant, for example, from the viewpoint of suppressing unexpected reactions with other components in the composition and improving the storage stability of the composition.

The surfactant (H) preferably contains a surfactant containing at least any one of a fluorine atom and a silicon atom. This contributes not only to obtaining a uniform resin film (improving coatability) or improving developability, but also to improving adhesive strength. As such a surfactant, for example, a nonionic surfactant containing at least any one of a fluorine atom and a silicon atom is preferable. Examples of commercially available products that can be used as the surfactant (H) include F-251, F-253, F-281, F-430, F-477, and F-551 of the "Megafac" series manufactured by DIC Corporation. , F-552, F-553, F-554, F-555, F-556, F-557, F-558, F-559, F-560, F-561, F-562, F-563, F -565, F-568, F-569, F-570, F-572, F-574, F-575, F-576, R-40, R-40-LM, R-41, R-94, etc. Fluorine-containing oligomer structure surfactants, fluorine-containing nonionic surfactants such as Ftergent 250 and Ftergent 251 manufactured by NEOS COMPANY LIMITED, SILFOAM (registered trademark) series manufactured by Wacker Chemie AG (for example, SD 100 TS, SD 670 , SD 850, SD 860, SD 882) and other polysiloxane surfactants. Moreover, FC4430 or FC4432 etc. by 3M company are mentioned as a preferable surfactant.

When the photosensitive resin composition of this embodiment contains a surfactant (H), it may contain 1 type, or 2 or more types of surfactants. When the photosensitive resin composition of this embodiment contains a surfactant (H), when the content of the polyimide (A) is 100 parts by mass, the amount is, for example, 0.001 to 1 part by mass, which is relatively Preferably, it is 0.005-0.5 mass part.

(Water (I)) The photosensitive resin composition of this embodiment may contain water. Due to the presence of water, for example, the hydrolysis reaction of the silane coupling agent (G) is likely to proceed, and the adhesiveness between the substrate and the cured film tends to be further improved.

When the photosensitive resin composition of the present embodiment contains water, the amount thereof is preferably 0.1 to 5 parts by mass, more preferably 0.2 -3 parts by mass, more preferably 0.5-2 parts by mass.

The water content of the photosensitive resin composition can be quantified by the Carl Fischer method.

(Solvent (J)/property of composition) It is preferable that the photosensitive resin composition of this embodiment contains a solvent (J). Thereby, a photosensitive resin film can be easily formed on a board|substrate (particularly, a board|substrate with a level difference) by a coating method. Solvent (J) usually contains an organic solvent. The organic solvent is not particularly limited as long as it can dissolve or disperse the above-mentioned components and does not substantially chemically react with the components.

Examples of organic solvents include acetone, methyl ethyl ketone, toluene, propylene glycol cresyl ethyl ether, propylene glycol dimethyl ether, propylene glycol 1-monomethyl ether 2-acetate, diethylene glycol ethyl methyl ether, Diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, benzyl alcohol, propylene carbonate, ethylene glycol diacetate, propylene glycol diacetate, propylene glycol mono Methyl ether acetate, dipropylene glycol methyl n-propyl ether, butyl acetate, γ-butyrolactone, methyl lactate, ethyl lactate, butyl lactate, etc. These may be used alone or in combination of plural kinds.

When the photosensitive resin composition of this embodiment contains a solvent (J), the photosensitive resin composition of this embodiment is normally a varnish shape. More specifically, the photosensitive resin composition of this embodiment is preferably a varnish-like composition in which at least a polyimide (A) and a polyfunctional (meth)acrylate compound (B) are dissolved in a solvent (J). thing. Since the photosensitive resin composition of the present embodiment is in the form of a varnish, a uniform film can be formed by coating. Moreover, a homogeneous cured film can be obtained by "dissolving" a polyimide (A) and a polyfunctional (meth)acrylate compound (B) in a solvent (J).

When using the solvent (J), it is used so that the concentration of the total solid content (non-volatile content) in the photosensitive resin composition is preferably 10 to 50% by mass, more preferably 20 to 45% by mass. . By setting it as this range, each component can be fully dissolved or disperse|distributed. In addition, good applicability can be ensured, and the flatness at the time of spin coating can also be made good. Furthermore, the viscosity of the photosensitive resin composition can be appropriately controlled by adjusting the content of the non-volatile components. As another viewpoint, the ratio of the polyimide (A) and the polyfunctional (meth)acrylate compound (B) in the entire composition is preferably 20 to 50% by mass. By using the polyimide (A) and the polyfunctional (meth)acrylate compound (B) in a certain amount, it is easy to form a film with an appropriate thickness.

(other ingredients) In addition to the above-mentioned components, the photosensitive resin composition of this embodiment may contain components other than the above-mentioned components as needed. Examples of such components include antioxidants, fillers such as silica, sensitizers, and film-forming agents.

<Manufacturing method of electronic device, electronic device> The manufacturing method of the electronic device of this embodiment includes: a film forming step of forming a photosensitive resin film on a substrate using the above photosensitive resin composition; an exposing step of exposing the photosensitive resin film; and In the developing step, the exposed photosensitive resin film is developed. Furthermore, the method of manufacturing an electronic device according to this embodiment preferably includes a thermosetting step of heating and curing the exposed photosensitive resin film after the above-mentioned developing step. Thereby, the cured film which has sufficient heat resistance can be obtained. Thus, the electronic device provided with the cured film of the photosensitive resin composition of this embodiment can be manufactured.

Hereinafter, a method of manufacturing an electronic device according to this embodiment, a structure of an electronic device including a cured product of the photosensitive resin composition according to this embodiment, and the like will be described in more detail with reference to the drawings.

FIG. 1 is a longitudinal sectional view showing an example of an electronic device according to this embodiment. In addition, FIG. 2 is a partially enlarged view of the area surrounded by chain lines in FIG. 1 . In the following description, the upper side in FIG. 1 is referred to as "upper" and the lower side is referred to as "lower".

The electronic device 1 shown in FIG. 1 has a so-called package-on-package structure, which includes a through-electrode substrate 2 and a semiconductor package 3 mounted thereon.

The penetrating electrode substrate 2 includes an insulating layer 21 , a plurality of penetrating wirings 221 penetrating from the upper surface to the lower surface of the insulating layer 21 , a semiconductor chip 23 embedded in the insulating layer 21 , and a layer provided under the lower surface of the insulating layer 21 . The wiring layer 24 , the upper wiring layer 25 provided on the upper surface of the insulating layer 21 , and the solder bumps 26 provided on the lower surface of the lower wiring layer 24 .

The semiconductor package 3 has a package substrate 31, a semiconductor chip 32 mounted on the package substrate 31, a bonding wire 33 electrically connecting the semiconductor chip 32 and the package substrate 31, a sealing layer 34 embedded with the semiconductor chip 32 and the bonding wire 33, and a Solder bumps 35 on the lower surface of the package substrate 31 .

Furthermore, a semiconductor package 3 is stacked on the through-electrode substrate 2 . Thereby, the solder bump 35 of the semiconductor package 3 is electrically connected to the upper wiring layer 25 penetrating the electrode substrate 2 .

In such an electronic device 1 , there is no need to use a thick substrate such as an organic substrate including a core layer for the through-electrode substrate 2 , and thus the thickness can be easily reduced. Therefore, it is also possible to contribute to miniaturization of electronic equipment incorporating the electronic device 1 .

In addition, since the through-electrode substrate 2 and the semiconductor package 3 having mutually different semiconductor chips are laminated, the mounting density per unit area can be increased. Therefore, both miniaturization and high performance can be achieved.

Hereinafter, the through-electrode substrate 2 and the semiconductor package 3 will be described in further detail. The lower wiring layer 24 and the upper wiring layer 25 included in the through-electrode substrate 2 shown in FIG. 2 include an insulating layer, a wiring layer, a through wiring, and the like, respectively. Thereby, the lower wiring layer 24 and the upper wiring layer 25 include wiring inside and on the surface, and are electrically connected to each other through the penetrating wiring 221 penetrating the insulating layer 21 .

The wiring layer included in the lower wiring layer 24 is connected to the semiconductor chip 23 and the solder bump 26 . Therefore, the lower wiring layer 24 functions as a rewiring layer of the semiconductor chip 23 , and the solder bump 26 functions as an external terminal of the semiconductor chip 23 .

As described above, the penetrating wiring 221 shown in FIG. 2 is provided to penetrate the insulating layer 21 . Thereby, the lower wiring layer 24 and the upper wiring layer 25 are electrically connected, and the electrode substrate 2 and the semiconductor package 3 can be stacked through, so that the electronic device 1 can be enhanced in functionality.

The wiring layer 253 included in the upper wiring layer 25 shown in FIG. 2 is connected to the through wiring 221 and the solder bump 35 . Therefore, the upper wiring layer 25 will be electrically connected to the semiconductor chip 23 , thereby functioning as a redistribution layer of the semiconductor chip 23 , and also functioning as an interposer between the semiconductor chip 23 and the packaging substrate 31 . The cured film of the photosensitive resin composition of this embodiment can be used for the insulating layer which comprises a rewiring layer.

According to this embodiment, a semiconductor wafer 23 and a rewiring layer (upper wiring layer 25) provided on the surface of the semiconductor wafer 23 can be realized, and the insulating layer in the rewiring layer is cured by the photosensitive resin composition of this embodiment. Electronic devices composed of objects.

The effect of reinforcing the insulating layer 21 can be obtained by the penetrating wiring 221 penetrating the insulating layer 21 . Therefore, even when the mechanical strength of the lower wiring layer 24 or the upper wiring layer 25 is low, it is possible to prevent the mechanical strength of the penetrating electrode substrate 2 from decreasing. As a result, the lower wiring layer 24 or the upper wiring layer 25 can be further thinned, and the thickness of the electronic device 1 can be reduced.

In addition, the electronic device 1 shown in FIG. 1 includes a through-wiring 222 located on the upper surface of the semiconductor wafer 23 and provided so as to penetrate the insulating layer 21 in addition to the through-wiring 221 . This enables electrical connection between the upper surface of the semiconductor wafer 23 and the upper wiring layer 25 .

The insulating layer 21 is provided to cover the semiconductor wafer 23 . Thereby, the effect of protecting the semiconductor wafer 23 can be improved. As a result, the reliability of the electronic device 1 can be improved. In addition, an electronic device 1 that can be easily applied to a mounting method such as the package-on-package structure of this embodiment can be obtained.

The diameter W (see FIG. 2 ) of the penetrating wiring 221 is not particularly limited, but is preferably about 1 to 100 μm, more preferably about 2 to 80 μm. Thereby, the electrical conductivity of the penetrating wiring 221 can be ensured without impairing the mechanical properties of the insulating layer 21 .

The semiconductor package 3 shown in FIG. 1 can be any form of package. Examples include QFP (Quad Flat Package), SOP (Small Outline Package), BGA (Ball Grid Array), CSP (Chip Size Package), QFN (Quad Flat Non-leaded Package, Quad Flat Non-leaded Package), SON (Small Outline Non-leaded Package, Small Outline Non-leaded Package), LF-BGA (Lead Flame BGA, lead frame ball grid array) and other forms.

The arrangement of the semiconductor wafers 32 is not particularly limited, and as an example, a plurality of semiconductor wafers 32 are stacked in FIG. 1 . Thereby, high density of mounting density is realized. Furthermore, the plurality of semiconductor wafers 32 may be arranged side by side along the planar direction, or may be arranged side by side along the planar direction while being stacked along the thickness direction.

The packaging substrate 31 may be any substrate, for example, a substrate including an insulating layer, a wiring layer, and through wiring not shown in the figure. Among them, the solder bump 35 and the bonding wire 33 can be electrically connected via a through-wire.

The sealing layer 34 is made of, for example, a known sealing resin material. By providing such a sealing layer 34 , it is possible to protect the semiconductor wafer 32 or the bonding wire 33 from external force or external environment.

The semiconductor chip 23 included in the through-electrode substrate 2 and the semiconductor chip 32 included in the semiconductor package 3 are arranged close to each other. Thereby, advantages such as high-speed mutual communication and low loss can be enjoyed. From this point of view, for example, if one of the semiconductor chip 23 and the semiconductor chip 32 is used as a CPU (Central Processing Unit, central processing unit) or GPU (Graphics Processing Unit, graphics processing unit), AP (Application Processor, application program Processor) and other computing components, and the other as a DRAM (Dynamic Random Access Memory, dynamic random access memory) or flash memory and other memory components, etc., these components can be placed close to each other in the same device configuration. Thereby, it is possible to realize the electronic device 1 that achieves both high functionality and miniaturization.

Next, a method of manufacturing the electronic device 1 shown in FIG. 1 will be described.

FIG. 3 is a step diagram showing a method of manufacturing the electronic device 1 shown in FIG. 1 . 4 to 6 are views for explaining a method of manufacturing the electronic device 1 shown in FIG. 1 , respectively.

The manufacturing method of the electronic device 1 includes: a chip configuration step S1, obtaining an insulating layer 21 to embed the semiconductor chip 23 and the through-wires 221 and 222 disposed on the substrate 202; an upper wiring layer forming step S2, obtaining an insulating layer 21 on the insulating layer 21 and The upper wiring layer 25 is formed on the semiconductor wafer 23; the substrate peeling step S3 is to peel off the substrate 202; the lower wiring layer forming step S4 is to form the lower wiring layer 24; the solder bump forming step S5 is to form solder bumps 26 to obtain a through-electrode substrate 2; and a build-up step S6 of building up the semiconductor package 3 on the through-electrode substrate 2 .

Wherein, the upper wiring layer forming step S2 includes: a first resin film disposing step S20, disposing a photosensitive resin varnish 5 (varnish-like photosensitive resin composition) on the insulating layer 21 and the semiconductor wafer 23, thereby obtaining a photosensitive resin layer 2510; the first exposure step S21, performing exposure treatment on the photosensitive resin layer 2510; the first developing step S22, performing developing treatment on the photosensitive resin layer 2510; the first hardening step S23, performing hardening treatment on the photosensitive resin layer 2510; Wiring layer forming step S24, forming wiring layer 253; second resin film disposing step S25, disposing photosensitive resin varnish 5 on photosensitive resin layer 2510 and wiring layer 253, thereby obtaining photosensitive resin layer 2520; second exposing step S26 , performing exposure treatment on the photosensitive resin layer 2520; second developing step S27, implementing developing treatment on the photosensitive resin layer 2520; second hardening step S28, implementing hardening treatment on the photosensitive resin layer 2520; and through wiring forming step S29, Penetrating wiring 254 is formed in opening 424 (through hole).

Hereinafter, each step will be described in order. The following manufacturing methods are examples and are not limited thereto.

[1] Wafer configuration step S1 First, as shown in FIG. 4( a ), prepare an embedding mold that includes a substrate 202 , a semiconductor chip 23 disposed on the substrate 202 , through-wires 221 , 222 , and an insulating layer 21 provided to embed them. Chip structure 27 .

The constituent material of the substrate 202 is not particularly limited, and examples thereof include metal materials, glass materials, ceramic materials, semiconductor materials, and organic materials. In addition, semiconductor wafers such as silicon wafers, glass wafers, and the like can also be used as the substrate 202 .

The semiconductor chip 23 is then mounted on the substrate 202 . In this manufacturing method, as an example, a plurality of semiconductor wafers 23 are separated from each other, and these are simultaneously provided on the same substrate 202 . The plurality of semiconductor wafers 23 may be of the same kind or of different kinds. In addition, the substrate 202 and the semiconductor wafer 23 may be fixed via an adhesive layer (not shown) such as a die attach film.

An interposer (not shown) may also be provided between the substrate 202 and the semiconductor wafer 23 as required. The interposer functions, for example, as a redistribution layer of the semiconductor wafer 23 . Therefore, the interposer may include pads (not shown) for electrically connecting to electrodes of the semiconductor wafer 23 to be described later. Thereby, the pad spacing and arrangement pattern of the semiconductor wafer 23 can be changed, and the degree of freedom in designing the electronic device 1 can be further improved. For the interposer, for example, inorganic substrates such as silicon substrates, ceramic substrates, and glass substrates, organic substrates such as resin substrates, and the like are used.

The insulating layer 21 may be, for example, a resin film (organic insulating layer) containing a thermosetting resin or a thermoplastic resin as a component of the photosensitive resin composition, or may be a general sealing material used in the technical field of semiconductors.

Examples of the constituent material of the through wirings 221 and 222 include copper or copper alloys, aluminum or aluminum alloys, gold or gold alloys, silver or silver alloys, nickel or nickel alloys, and the like.

Furthermore, it is also possible to prepare the chip-embedded structure 27 produced by a method different from the above.

[2] Upper layer wiring layer formation step S2 Next, an upper wiring layer 25 is formed on the insulating layer 21 and on the semiconductor wafer 23 .

[2-1] First resin film arrangement step S20 First, as shown in FIG. 4( b ), a photosensitive resin varnish 5 is applied (arranged) on the insulating layer 21 and the semiconductor wafer 23 . Thereby, as shown in FIG.4(c), the liquid coating film of the photosensitive resin varnish 5 is obtained. The photosensitive resin varnish 5 is the photosensitive resin composition of this embodiment.

Coating of the photosensitive resin varnish 5 is performed using, for example, a spin coater, a bar coater, a spray device, an inkjet device, or the like.

The viscosity of the photosensitive resin varnish 5 is not particularly limited, but is 10 cP to 6000 cP, preferably 20 cP to 5000 cP, more preferably 30 cP to 4000 cP. When the viscosity of the photosensitive resin varnish 5 is within the above range, a thinner photosensitive resin layer 2510 can be formed (see FIG. 4( d )). As a result, the upper wiring layer 25 can be made thinner, and the electronic device 1 can be easily reduced in thickness. The viscosity of the photosensitive resin varnish 5 is, for example, a value measured at a rotational speed of 100 rpm using a cone-plate viscometer (TV-25, manufactured by TOKI SANGYO CO., LTD.).

Next, the liquid coating of the photosensitive resin varnish 5 is dried. Thereby, the photosensitive resin layer 2510 shown in FIG. 4( d ) is obtained.

The drying conditions of the photosensitive resin varnish 5 are not particularly limited, and examples thereof include heating at a temperature of 80 to 150° C. for 1 to 60 minutes.

In this step, instead of the procedure of applying the photosensitive resin varnish 5 , a procedure of arranging a photosensitive resin film obtained by forming the photosensitive resin varnish 5 into a film may be employed. The photosensitive resin film is the photosensitive resin composition of the present embodiment and is a photosensitive resin film.

The photosensitive resin film is produced, for example, by coating the photosensitive resin varnish 5 on a base such as a carrier film with various coating devices, and then drying the obtained coating film.

After forming the photosensitive resin layer 2510 in this way, the photosensitive resin layer 2510 is subjected to a pre-exposure heat treatment as necessary. By performing heat treatment before exposure, the molecules contained in the photosensitive resin layer 2510 can be stabilized, thereby stabilizing the reaction in the first exposure step S21 described later. On the other hand, by heating under heating conditions as described later, the adverse effect of heating on the photoacid generator can be minimized.

The temperature of the heat treatment before exposure is preferably from 70 to 130°C, more preferably from 75 to 120°C, further preferably from 80 to 110°C. If the temperature of the pre-exposure heat treatment is lower than the above-mentioned lower limit, the purpose of stabilizing molecules by the pre-exposure heat treatment may not be achieved. On the other hand, if the temperature of the heat treatment before exposure is higher than the above upper limit, the activity of the photoacid generator becomes too active, resulting in the expansion of the influence that it is difficult to generate acid even when irradiated with light in the first exposure step S21 described later. , so that the processing accuracy of patterning may decrease.

The time of the pre-exposure heat treatment is appropriately set according to the temperature of the pre-exposure heat treatment, but at the above temperature, it is preferably 1 to 10 minutes, more preferably 2 to 8 minutes, further preferably 3 to 6 minutes. If the time of the pre-exposure heat treatment is less than the above lower limit, the heating time is insufficient, and therefore, the purpose of stabilizing molecules by the pre-exposure heat treatment may not be achieved. On the other hand, if the time of the heat treatment before exposure exceeds the above upper limit, the heating time will be too long, so even if the temperature of the heat treatment before exposure falls within the above range, the effect of the photoacid generator may be inhibited.

The environment of the heat treatment is not particularly limited. An inert gas atmosphere, a reducing gas atmosphere, etc. may be used, but in consideration of work efficiency, etc., it is under the atmosphere.

The environmental pressure is not particularly limited. It may be under reduced pressure or under increased pressure, but in consideration of work efficiency, etc., it is normal pressure. In addition, normal pressure refers to a pressure of about 30 to 150 kPa, preferably atmospheric pressure.

[2-2] First exposure step S21 Next, exposure processing is performed on the photosensitive resin layer 2510 .

First, as shown in FIG. 4( d ), a mask 412 is disposed on a specific region on the photosensitive resin layer 2510 . Thereafter, light (actinic radiation) is irradiated through the mask 412 . Thereby, exposure processing is performed on the photosensitive resin layer 2510 according to the pattern of the mask 412 .

In FIG. 4( d ), a case where the photosensitive resin layer 2510 has so-called negative photosensitivity is shown. In this example, the region of the photosensitive resin layer 2510 corresponding to the light-shielding portion of the mask 412 is dissolved in the developer.

On the other hand, in a region corresponding to the transmissive portion of the mask 412, active chemical species are generated from the photocationic polymerization initiator. The active chemical species acts as a catalyst for the hardening reaction.

The exposure amount in the exposure processing is not particularly limited. 100-2000mJ/cm ² is preferable, and 200-1000mJ/cm ² is more preferable. Thereby, underexposure and overexposure in the photosensitive resin layer 2510 can be suppressed. As a result, high patterning accuracy can finally be realized. Thereafter, a post-exposure heat treatment is performed on the photosensitive resin layer 2510 as necessary.

The temperature of the post-exposure heat treatment is not particularly limited. Preferably it is 50-150 degreeC, More preferably, it is 50-130 degreeC, More preferably, it is 55-120 degreeC, Most preferably, it is 60-110 degreeC. By performing post-exposure heat treatment at such a temperature, the catalytic effect of the generated acid is sufficiently enhanced, and the thermosetting resin can be fully reacted in a shorter time. By setting the temperature within the above-mentioned range, it is possible to suppress a decrease in processing accuracy of patterning due to acceleration of acid diffusion. By making the temperature of post-exposure heat processing more than the said lower limit, the reaction rate of a thermosetting resin can be improved, and productivity can be improved. On the other hand, by making the temperature of post-exposure heat processing below the said upper limit, the fall of the processing precision of patterning by the acceleration|stimulation of acid diffusion can be suppressed.

The time for the post-exposure heat treatment is appropriately set according to the temperature of the post-exposure heat treatment. At the above temperature, it is preferably 1 to 30 minutes, more preferably 2 to 20 minutes, further preferably 3 to 15 minutes. By performing post-exposure heat treatment for such a period of time, the thermosetting resin can be sufficiently reacted, and the diffusion of acid can be suppressed, thereby suppressing a reduction in the processing accuracy of patterning.

The environment of post-exposure heat treatment is not particularly limited. An inert gas atmosphere, a reducing gas atmosphere, etc. may be used, but in consideration of work efficiency, etc., it is under the atmosphere.

The ambient pressure of post-exposure heat treatment is not particularly limited. It may be under reduced pressure or under increased pressure, but in consideration of work efficiency, etc., it is normal pressure. Thereby, pre-exposure heat treatment can be performed relatively easily. In addition, normal pressure refers to a pressure of about 30 to 150 kPa, preferably atmospheric pressure.

[2-3] First developing step S22 Next, a development process is performed on the photosensitive resin layer 2510 . Thereby, an opening 423 penetrating through the photosensitive resin layer 2510 is formed in a region corresponding to the light shielding portion of the mask 412 (see FIG. 5( e )).

As a developer, an organic developer, a water-soluble developer, etc. are mentioned, for example. In this embodiment, it is preferable that the developing solution contains an organic solvent. More specifically, the developing solution is preferably a developing solution mainly composed of an organic solvent (a developing solution in which 95% by mass or more of the components are organic solvents). By performing development with a developing solution containing an organic solvent, it is possible to suppress swelling of the pattern due to the developing solution, etc., compared to the case of performing development with an alkaline developing solution (aqueous system). That is, it is easier to obtain a clear pattern.

Specific examples of organic solvents that can be used in the developer include ketone-based solvents such as cyclopentanone, ester-based solvents such as propylene glycol monomethyl ether acetate (PGMEA) and butyl acetate, propylene glycol monomethyl ether acetate, etc. Ether-based solvents such as ether, etc. As the developer, an organic solvent developer consisting only of an organic solvent and containing only unavoidable impurities can be used. Examples of unavoidable impurities include metal elements and moisture, but from the viewpoint of preventing contamination of electronic devices, the less unavoidable impurities are better.

The method of bringing the developer into contact with the photosensitive resin layer 2510 is not particularly limited. A generally known dipping method, a puddle method, a spray method, and the like can be appropriately applied.

The time of the developing step is usually about 5 to 300 seconds, preferably about 10 to 120 seconds, and is appropriately adjusted according to the film thickness of the resin film or the shape of the pattern to be formed.

[2-4] First hardening step S23 After the development treatment, curing treatment (post-development heat treatment) is performed on the photosensitive resin layer 2510 . The conditions of the hardening treatment are not particularly limited, and may be a heating temperature of about 160 to 250° C. and a heating time of about 30 to 240 minutes. Thereby, it is possible to cure the photosensitive resin layer 2510 while suppressing the influence of heat on the semiconductor wafer 23 , thereby obtaining the organic insulating layer 251 .

[2-5] Wiring layer formation step S24 Next, a wiring layer 253 is formed on the organic insulating layer 251 (see FIG. 5( f )). The wiring layer 253 is formed, for example, by forming a metal layer using a vapor phase film-forming method such as a sputtering method or a vacuum evaporation method, and then patterning it by a photolithography method and an etching method. Surface modification treatment such as plasma treatment may be performed before forming the wiring layer 253 .

[2-6] Second resin film arrangement step S25 Next, as shown in FIG. 5( g ), a photosensitive resin layer 2520 is obtained in the same manner as in the first resin film disposing step S20 . The photosensitive resin layer 2520 is arranged to cover the wiring layer 253 . Thereafter, a pre-exposure heat treatment is performed on the photosensitive resin layer 2520 as necessary. The processing conditions are, for example, the conditions described in the first resin film arranging step S20.

[2-7] Second exposure step S26 Next, exposure processing is performed on the photosensitive resin layer 2520 . The processing conditions are, for example, the conditions described in the first exposure step S21. Thereafter, a post-exposure heat treatment is performed on the photosensitive resin layer 2520 as necessary. The processing conditions are, for example, the conditions described in the first exposure step S21.

[2-8] Second developing step S27 Next, a development process is performed on the photosensitive resin layer 2520 . The processing conditions are, for example, the conditions described in the first developing step S22. Thereby, the opening part 424 which penetrates the photosensitive resin layer 2510,2520 is formed (refer FIG.5(h)).

[2-9] Second hardening step S28 After the development treatment, curing treatment (post-development heat treatment) is performed on the photosensitive resin layer 2520 . The hardening conditions are, for example, the conditions described in the first hardening step S23. Thereby, the photosensitive resin layer 2520 is hardened, and the organic insulating layer 252 is obtained (see FIG. 6( i )).

In the present embodiment, the upper wiring layer 25 has two layers, the organic insulating layer 251 and the organic insulating layer 252 , but may have three or more layers. In this case, a series of steps from the additional wiring layer forming step S24 to the second curing step S28 may be repeated after the second curing step S28.

[2-10] Through wiring formation step S29 Next, the penetrating wiring 254 shown in FIG. 6( i ) is formed in the opening 424 .

Penetrating wiring 254 is formed using a known method, for example, the following method.

First, a seed layer (not shown) is formed on the organic insulating layer 252 . The seed layer is formed on the inner surface (side surface and bottom surface) of the opening 424 and the upper surface of the organic insulating layer 252 . As the seed layer, for example, a copper seed layer is used. Also, the seed layer is formed by, for example, sputtering. The seed layer may be made of the same kind of metal as that of the penetrating wiring 254 to be formed, or may be made of a different kind of metal.

Next, a not-shown resist layer is formed on a region other than the opening 424 in the not-shown seed layer. Thereafter, the opening 424 is filled with metal using the resist layer as a mask. For this filling, for example, an electroplating method is used. Examples of the metal to be filled include copper or copper alloys, aluminum or aluminum alloys, gold or gold alloys, silver or silver alloys, nickel or nickel alloys, and the like. By embedding the conductive material in the opening 424 in this way, the penetrating wiring 254 is formed.

Next, the resist layer (not shown) is removed. Furthermore, the unillustrated seed layer on the organic insulating layer 252 is removed. For this purpose, a flash etching method can be used, for example. The formation position of the penetrating wiring 254 is not limited to the illustrated position.

[3] Substrate peeling step S3 Next, as shown in FIG. 6( j ), the substrate 202 is peeled off. Thereby, the lower surface of the insulating layer 21 is exposed.

[4] Lower layer wiring layer formation step S4 Next, as shown in FIG. 6( k ), the lower wiring layer 24 is formed on the lower surface side of the insulating layer 21 . The lower wiring layer 24 may be formed by any method, for example, may be formed in the same manner as the upper wiring layer forming step S2 described above. The lower wiring layer 24 thus formed is electrically connected to the upper wiring layer 25 via the through wiring 221 .

[5] Solder bump formation step S5 Next, as shown in FIG. 6(L), solder bumps 26 are formed on the lower wiring layer 24 . In addition, a protective film such as a solder resist layer may be formed on the upper wiring layer 25 or the lower wiring layer 24 as needed. In this way, through-electrode substrate 2 is obtained.

The through-electrode substrate 2 shown in FIG. 6(L) may be divided into a plurality of regions. Therefore, a plurality of through-electrode substrates 2 can be manufactured efficiently by, for example, singulating the through-electrode substrates 2 along the dot-chain line shown in FIG. 6(L) . In addition, for singulation, for example, a diamond cutter or the like can be used.

[6] Lamination step S6 Next, the semiconductor package 3 is disposed on the singulated through-electrode substrate 2 . Thereby, the electronic device 1 shown in FIG. 1 is obtained.

Such a manufacturing method of the electronic device 1 can be applied to a wafer-level process or a panel-level process using a large-area substrate. Thereby, the manufacturing efficiency of the electronic device 1 can be improved, thereby achieving cost reduction.

As mentioned above, although embodiment of this invention was described, these are only the example of this invention, and various structures other than the above-mentioned can also be employ|adopted. In addition, the present invention is not limited to the above-described embodiments, and modifications, improvements, and the like within the scope of achieving the object of the present invention are included in the present invention. [Example]

Embodiments of the present invention will be described in detail based on Examples and Comparative Examples. Just in case, it is reminded that the present invention is not limited only to the examples. Hereinafter, "DMAc" is an abbreviation for dimethylacetamide. For other abbreviations, they will be properly explained in the text.

＜Synthesis of Polymer＞ (Synthesis of Polymer (A-1)) TFMB<2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl>64.1g (0.20 mole ), 6FDA<4,4'-(hexafluoroisopropylidene) diphthalic dianhydride>97.7g (0.22 moles) and 500g of DMAc were stirred, and TFMB and 6FDA were dissolved in DMAc. Furthermore, stirring was continued at room temperature for 12 hours under a nitrogen stream to carry out a polymerization reaction to obtain a polyamic acid solution.

16 g of pyridine was added to the obtained polyamic acid solution. Thereafter, 82 g of acetic anhydride was added dropwise at room temperature. Furthermore, thereafter, the liquid temperature was kept at 20 to 100° C., stirring was continued for 24 hours, and imidization reaction was performed. Thus a polyimide solution was obtained.

The obtained polyimide solution was poured into 1,000 g of methanol with stirring in a 5 L container to precipitate a polyimide resin. Thereafter, the solid polyimide resin was filtered using a suction filter, and further washed with 1,000 g of methanol. Then, it dried at 100 degreeC for 24 hours using the vacuum dryer, and dried at 200 degreeC for 3 hours further. The polymer (A-1), which is a polyimide powder having an acid anhydride group at the terminal, was obtained through the above steps. The weight average molecular weight (Mw) of the polymer (A-1) measured by GPC was 25,000. Further, polymer (A-1) was measured by ¹ H-NMR, and the imidization ratio (as defined above) was calculated from the quantitative value of the amide peak of the polyimide relative to the peak of the aromatic ring. The imidization rate is above 99%.

(Synthesis of Polymer (A-2)) Instead of TFMB64.1g (0.20 mol), TFMB56.4g (0.176 mol) and BAPP-F<2,2,-bis[4-(4-aminophenoxy)phenyl]-1,1 were used , 1,3,3,3-Hexafluoropropane> 12.4 g (0.024 mol), Polymer synthesis was performed in the same manner as in Example 1 except that. Thereafter, a polymer (A-2) which is a polyimide powder having an acid anhydride group at the terminal was obtained. The weight average molecular weight (Mw) of the polymer (A-2) measured by GPC was 26,000. Also, the imidization rate of the polymer (A-2) measured by NMR measurement was 99% or more.

(Synthesis of Polymer (A-3)) Instead of 6FDA97.7g (0.22 moles), 6FDA78.2g (0.176 moles) and ODPA<4,4'-diphenyl ether tetracarboxylic dianhydride>13.7g (0.044 moles) were used. Polymer synthesis was performed in the same manner as in Example 1. Thereafter, a polymer (A-3) which is a polyimide powder having an acid anhydride group at the terminal was obtained. The weight average molecular weight (Mw) of the polymer (A-3) measured by GPC was 24,000. Also, the imidization rate of the polymer (A-3) measured by NMR measurement was 99% or more.

(Synthesis of Polymer (A-4)) Instead of 6FDA97.7g (0.22 mol), 6FDA83.1g (0.187 mol) and BPDA<3,3',4,4'-biphenyltetracarboxylic dianhydride>9.71g (0.033 mol) were used, except Otherwise, polymer synthesis was performed in the same manner as in Example 1. Thereafter, a polyimide resin (A-4) having an acid anhydride group at the terminal was obtained. The weight average molecular weight (Mw) of the polymer (A-4) measured by GPC was 24,000. Also, the imidization rate of the polymer (A-4) measured by NMR measurement was 99% or more.

(Synthesis of polymer (A-5) (for comparison)) Put 428g of γ-butyrolactone, 155.11g of 4,4'-oxydiphthalic dianhydride (4,4'-oxydiphthalic dianhydride) and 130.14g of 2-hydroxyethyl methacrylate in a 2L separable flask , stir the contents of the flask at room temperature to dissolve completely. Next, while stirring at room temperature, 79.1 g of pyridine was added, and further stirred at room temperature for 16 hours.

While cooling and stirring the thus obtained solution under ice cooling, 206.3 g of dicyclohexyl carbodiimide (dicyclohexyl carbodiimide) was dissolved in 206 g of γ-butyrolactone to the solution over 30 minutes. solution. Next, 120.1 g of 4,4'-diaminodiphenyl ether and 240 g of γ-butyrolactone were added, and stirring was continued at room temperature for 2 hours. After completion of the reaction, 30 g of ethanol was added and stirred for 1 hour. Thereafter, 400 g of γ-butyrolactone was added and stirred, and the generated precipitate was removed by filtration. Thereby, the reaction liquid of polyamide ester was obtained. The obtained reaction solution was added dropwise to a large amount of 30% by mass aqueous methanol solution with stirring at room temperature to precipitate a polymer. The obtained precipitate was collected by filtration and vacuum-dried to obtain a polymer (A-5). The weight average molecular weight (Mw) of the polymer (A-5) measured by GPC was 18,000. In addition, the imidization rate of the polymer (A-5) measured by NMR measurement was 1% or less.

＜Preparation of photosensitive resin composition＞ Each raw material blended according to the following Table 1 was stirred at room temperature until the raw materials were completely dissolved to obtain a solution. Thereafter, the solution was filtered with a nylon filter having a pore size of 0.2 μm. In this way, a varnish-like photosensitive resin composition was obtained.

The details of the raw materials of each component in Table 1 are as follows.

＜(A) Polyimide＞ (A-1) Polymer synthesized above (polyimide resin containing imide ring structure) (A-2) Polymer synthesized above (polyimide resin containing imide ring structure) (A-3) Polymer synthesized above (polyimide resin containing imide ring structure) (A-4) Polymer synthesized above (polyimide resin containing imide ring structure) (A-5) Polymer synthesized above (polyamide ester resin (for comparative example))

The structure of each of the above-mentioned polymers is shown below.

＜(B) Multifunctional (meth)acrylate compound＞ (B-1) Viscoat #802 (manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.) (a mixture of compounds having 5 to 10 acryl groups) (B-2) A-9550 (manufactured by SHIN-NAKAMURA CHEMICAL CO, LTD.) (mixture of compounds having 5 to 6 acryl groups) (B-3) Viscoat #300 (manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.) (a mixture of compounds having 3 to 4 acryl groups) (B-4) Viscoat #230 (manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.) (a compound having two acryl groups)

The configurations of the aforementioned (B-1) to (B-4) are shown below.

＜(C) Photosensitizer＞ (C-1) Irgacure OXE01 (manufactured by BASF Corporation, oxime ester type photoradical generator) (C-2) ADEKA ARKLS NCI-730 (manufactured by ADEKA CORPORATION, oxime ester type photoradical generator)

＜(D) Thermal radical generator＞ (D-1) PERKADOX BC (manufactured by KAYAKU NOURYON CORPORATION, organic peroxide, cumyl peroxide)

＜(E) Epoxy resin＞ (E-1) TECHMORE VG3101L (manufactured by Printec Corporation) (E-2) CELLOXIDE 2021P (manufactured by Daicel Corporation)

＜(F) Hardening catalyst＞ (F-1) 4,4'-sulfonyl diphenol tetraphenylphosphonium The synthesis method of the said hardening catalyst (F-1) is as follows. Solution 1 was prepared by putting 37.5 g (0.15 mol) of 4,4'-bisphenol S and 100 mL of methanol into a separable flask equipped with a stirring device, and stirring and dissolving at room temperature. A solution obtained by dissolving 4.0 g (0.1 mol) of sodium hydroxide in 50 mL of methanol in advance was added to the solution 1 while stirring, and the solution 2 was obtained. Next, a solution obtained by dissolving 41.9 g (0.1 mol) of tetraphenylphosphine bromide in 150 mL of methanol in advance was added to Solution 2 to obtain Solution 3 . Solution 3 was continuously stirred for a while, and 300 mL of methanol was added to solution 3 as solution 4. Thereafter, the solution 4 in the flask was added dropwise to a large amount of water with stirring to obtain a white precipitate. The precipitate was filtered and dried. Through the above steps, the target product in white crystals was obtained.

＜(G) Silane coupling agent＞ (G-1) KBM-503 (manufactured by Shin-Etsu Chemical Co., Ltd.) (G-2) X-12-967C (manufactured by Shin-Etsu Chemical Co., Ltd.)

＜(H) Surfactant＞ (H-1) FC4432 (manufactured by 3M Company, fluorine-based)

＜(J) (Solvent)＞ (J-1) Ethyl Lactate (EL) (J-2) Gamma-butyrolactone (GBL)

<Evaluation of curing shrinkage> The photosensitive resin composition was spin-coated on an 8-inch silicon wafer so that the film thickness after drying became 10 μm. Next, it heated at 120 degreeC for 3 minutes, and obtained the photosensitive resin film. The obtained photosensitive resin film was exposed to 300 mJ/cm ² using a high-pressure mercury lamp. Next, it was immersed in cyclopentanone for 30 seconds. Then, it dried by spin drying, and obtained the film after image development of the photosensitive resin composition. The film thickness of the film after this development was measured, and it was set as film thickness A. Furthermore, thereafter, heat treatment was performed at 170° C. for 90 minutes in a nitrogen atmosphere to harden the film after development. Through the above steps, a cured film of the photosensitive resin composition is obtained. The film thickness of this cured film was measured, and it was set as film thickness B. The film thickness A and the film thickness B were substituted into the following formula, and the curing shrinkage rate was calculated. In order to maintain the flatness after coating on wiring, it is preferable that the curing shrinkage rate is small. Hardening shrinkage [%]={(film thickness A-film thickness B)/film thickness A}×100

<Evaluation of flatness during coating (step embedding flatness)> A Cu wiring board in which Cu wiring with a width of 5 μm/pitch of 5 μm and a height of 5 μm was formed on a silicon wafer with an oxide film was fabricated. The photosensitive resin composition was applied on the Cu wiring board by spin coating so that the film thickness after drying would be 10 μm, and dried at 120° C. for 3 minutes to form a photosensitive resin film. The obtained photosensitive resin film was exposed to 300 mJ/cm ² using a high-pressure mercury lamp. Thereafter, it was immersed in cyclopentanone for 30 seconds. Furthermore, thereafter, heat treatment was performed at 170° C. for 90 minutes in a nitrogen atmosphere to form a cured film on the substrate. The obtained substrate with a cured film was cut out, and its cross section was polished. The unevenness|corrugation of the surface of the photosensitive resin film was evaluated by cross-sectional SEM observation. Those with surface irregularities of 1 μm or less were rated as ○ (good), those with surface irregularities of 1 to 3 μm were rated as Δ (usable level), and those exceeding 3 μm were rated as × (poor).

<Heat Resistance: Evaluation of Glass Transition Temperature (Tg)> (Preparation of Test Specimen for Measurement of Glass Transition Temperature (Tg)) The photosensitive resin composition was spin-coated on an 8-inch silicon wafer so that the film thickness after drying was 10 μm, followed by heating at 120° C. for 3 minutes to obtain a photosensitive resin film. The obtained photosensitive resin film was exposed to 300 mJ/cm ² using a high-pressure mercury lamp. Thereafter, the exposed resin film and the silicon wafer were dipped in cyclopentanone for 30 seconds. Furthermore, thereafter, heat treatment was performed at 170° C. for 90 minutes in a nitrogen atmosphere. Through the above steps, a cured product of the photosensitive resin composition is obtained. The obtained cured product and the silicon wafer were cut into single pieces with a width of 5 mm using a dicing saw. Thereafter, the cured product was peeled off from the substrate by immersing the single piece in a 2% by mass hydrofluoric acid aqueous solution. The peeled film-like cured product was dried at 60° C. for 10 hours to obtain a test piece (30 mm×5 mm×10 μm thick).

(Measurement of glass transition temperature (Tg)) The obtained test piece was heated to 300° C. using a thermomechanical analyzer (manufactured by Seiko Instruments Inc., TMA/SS6000) at a temperature increase rate of 10° C./minute, and the thermal expansion coefficient of the obtained test piece was measured. Next, based on the obtained measurement results, the glass transition temperature (Tg) of the cured product was calculated from the inflection point of the thermal expansion coefficient. The unit of Tg is °C. When no inflection point was observed in the coefficient of thermal expansion, it was evaluated as Tg > 300°C.

＜Measurement of tensile elongation＞ First, a test piece was produced in the same manner as in the above-mentioned "production of a test piece for measuring the glass transition temperature (Tg)". Using a tensile tester (manufactured by Orientec Corporation, Tensilon RTC-1210A), a tensile test was performed on the obtained test piece by a method based on JIS K 7161 in an environment of 23° C., and the tensile elongation of the test piece was measured. The tensile speed in the tensile test was set at 5 mm/min. The unit of tensile elongation is %.

＜Evaluation of Patternability＞ The photosensitive resin composition was coated on an 8-inch silicon wafer using a spin coater so that the film thickness after drying was 5 μm. Then, it dried at 100 degreeC for 3 minutes with the hot plate, and obtained the photosensitive resin film (photosensitive resin film A). Using an i-ray stepper (manufactured by Nikon Corporation, NSR-4425i) while changing the exposure amount, the mask (test pattern No. 1: a residual pattern and a punched hole pattern with a width of 0.5 to 50 μm) made by TOPPAN INC. This photosensitive resin film was irradiated with i-rays. Thereafter, development was performed for 30 seconds using cyclopentanone as a developer, followed by drying at 2,500 rotations for 10 seconds to obtain a developed film (negative pattern). Those with a via hole of 7 μmΦ were rated as ◎ (excellent), those with a via hole of 10 μmΦ were rated as ○ (good), and those without a via hole of 10 μm were rated as × (poor).

＜Evaluation of rate of change of viscosity at room temperature＞ The viscosity of the photosensitive resin composition immediately after blending was measured with the E-type viscometer (TVE-25L). Let the viscosity at this time be A. Thereafter, the varnish of the photosensitive resin composition was stored at 23° C. for 7 days, and the viscosity was measured again. Let the viscosity at this time be B. The viscosity change rate was calculated by substituting the viscosity A and the viscosity B into the following formula. A viscosity change rate of 5% or less was evaluated as ⊚ (excellent), 5 to 10% was evaluated as ◯ (good), and a viscosity change rate of more than 10% was evaluated as × (poor). In order to obtain a stable film thickness, a low viscosity change rate is preferable. Viscosity change rate [%]={(viscosity A-viscosity B)/viscosity A}×100

<Evaluation of Chemical Resistance> The photosensitive resin composition was spin-coated on an 8-inch silicon wafer so that the film thickness after drying became 10 μm, and then heated at 120° C. for 3 minutes to obtain a photosensitive resin film. The obtained photosensitive resin film was exposed to 300 mJ/cm ² using a high-pressure mercury lamp. Thereafter, it was immersed in cyclopentanone for 30 seconds. Furthermore, after that, it heat-processed at 170 degreeC for 90 minutes in nitrogen atmosphere, it hardened|cured, and the hardened|cured material of the photosensitive resin composition was obtained. The film thickness of the obtained cured film was measured. Let the film thickness at this time be film thickness A. Next, the obtained cured film was immersed in 50 degreeC dimethyl sulfone for 30 minutes. Thereafter, it was washed with isopropanol and dried by blowing air. Next, heat processing was performed on a 170° C. hot plate for 5 minutes. In this way, a film after the chemical resistance test was obtained. The film thickness of the obtained cured film was measured. Let the film thickness at this time be film thickness B. The film thickness change rate was calculated by substituting film thickness A and film thickness B into the following formula. A film thickness variation rate of 5% or less was evaluated as ⊚ (excellent), 5 to 10% was evaluated as ◯ (good), and that exceeding 10% was evaluated as × (poor). From the standpoint of tolerance to drugs in the process, it is preferable that the film thickness change rate be small. Film thickness change rate [%]={(film thickness A-film thickness B)/film thickness A}×100

<Evaluation of Insulation Reliability> (Preparation of Samples for Insulation Reliability) A Cu wiring board in which comb-shaped Cu wiring with a width of 5 μm/pitch of 5 μm and a height of 5 μm was formed on a silicon wafer with an oxide film was produced. The photosensitive resin composition was applied on the Cu wiring board by spin coating so that the film thickness after drying (the thickness of the non-wiring portion) was 10 μm, and dried at 120° C. for 3 minutes to form a photosensitive resin film. The obtained photosensitive resin film was exposed to 300 mJ/cm ² using a high-pressure mercury lamp. Thereafter, it was immersed in cyclopentanone for 30 seconds. Then, it heat-processed at 170 degreeC for 90 minutes in nitrogen atmosphere, and obtained the cured film. This was used as a sample for insulation reliability evaluation.

(Evaluation of Insulation Reliability) A dummy electronic device for evaluation was prepared by soldering the end of the Cu wiring (Cu electrode) and the electrode wiring of the substrate produced in the above (Sample Preparation for Insulation Reliability). A bias voltage of 3.5 V was applied to it using a B-HAST device, and at the same time it was placed in an environment of 130°C/85%RH. The insulation resistance value between the Cu wirings of the Cu wiring board was automatically measured every 6 minutes, and when the insulation resistance value became 1.0×10 ⁴ Ω or less, it was regarded as insulation breakdown. Thereafter, the time (h) from the start of the test to the breakdown of the insulation was measured. In the following table, the case where the time is 210 hours or more is described as ◎ (excellent), the case of 50 hours to 210 hours is described as ○ (good), and the case of less than 50 hours is described as × (poor).

Table 1 summarizes the blending of raw materials for each composition and the above-mentioned evaluation results.

the Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 Example 17 Comparative example 1 Blend composition [parts by mass] polyimide (A-1) 100 --- --- --- 100 100 100 100 100 100 100 100 100 100 100 100 100 --- (A-2) --- 100 --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- (A-3) --- --- 100 --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- (A-4) --- --- --- 100 --- --- --- --- --- --- --- --- --- --- --- --- --- --- (A-5) --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- --- 100 Multifunctional (methyl) Acrylate (B-1) 60 60 60 60 40 20 80 --- --- 60 60 60 60 60 60 60 --- --- (B-2) 20 20 20 20 20 60 --- 80 --- 20 20 20 20 20 20 20 --- --- (B-3) 20 20 20 20 10 60 --- --- 80 20 20 20 20 20 20 20 --- --- (B-4) --- --- --- --- --- --- --- --- --- 20 --- --- --- --- --- --- 100 40 Photosensitizer: photoradical generator (C-1) 3 3 3 3 3 3 3 3 3 3 6 3 3 3 3 3 3 5 (C-2) 7 7 7 7 7 7 7 7 7 7 6 7 7 7 7 7 7 --- thermal free radical generator (D-1) 10 10 10 10 10 10 10 10 10 10 10 3 20 --- 10 10 10 --- epoxy resin (E-1) 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 --- (E-2) 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 --- hardening catalyst (F-1) 3 3 3 3 3 3 3 3 3 3 3 3 3 3 --- 3 3 --- Silane coupling agent (G-1) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 (G-2) 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 Surfactant (H-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 water (I-1) 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 --- 2 2 Organic solvents (J-1) 282 282 282 282 247 329 259 259 259 306 285 274 294 271 279 280 282 180 (J-2) 282 282 282 282 247 329 259 259 259 306 285 274 294 271 279 280 282 180 Hardening shrinkage [%] <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 <3 10 30 Level difference embedded flatness --- ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ △ x Heat Resistance: Glass Transition Temperature [℃] 230 230 230 240 230 220 230 220 210 220 230 220 230 210 230 230 190 200 Tensile elongation [%] 50 60 60 50 50 60 40 50 60 70 40 40 40 40 30 50 60 40 patterning --- ◎ ◎ ◎ ◎ ◎ ◎ ○ ◎ ◎ ◎ ○ ◎ ◎ ◎ ◎ ◎ ◎ ◎ Normal temperature viscosity change rate --- ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ Chemical Resistance --- ◎ ◎ ◎ ◎ ○ ◎ ◎ ○ △ ◎ ◎ ◎ ◎ ○ ◎ ◎ △ ○ Insulation reliability --- ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ △ ○ ○

As shown in Table 1, in the evaluation of the photosensitive resin compositions of Examples 1 to 17, the curing shrinkage rate was small. Moreover, by using the photosensitive resin composition of Examples 1-17, the cured film with favorable flatness was successfully formed on the board|substrate which has a level difference. Moreover, the other various performances of the photosensitive resin composition of Examples 1-17 also showed favorable result. On the other hand, the photosensitive resin composition of Comparative Example 1 had a very large curing shrinkage rate, and could not form a cured film having good flatness. This is presumed to be because the curing mechanism of the photosensitive resin composition of Comparative Example 1 is that polyamide resin is cured by closing the ring, and dehydration occurs during curing.

If the examples are viewed more closely, the following will be understood. · From the comparison between Example 15 and other examples, it is considered that the use of a curing catalyst is preferable from the viewpoint of improving the tensile elongation. The hardening catalyst is effective to fully react the epoxy resin to improve the tensile elongation. · From the comparison between Example 16 and other examples, it is considered that the existence of water may make the adhesion assistant play a good role, thereby improving the adhesion. - From the comparison between Example 17 and other examples, it is thought that as a multifunctional (meth)acrylate, a trifunctional or more is preferable than a difunctional one. · From Examples 7 to 9, it can be understood that chemical resistance can be improved by using a multifunctional (meth)acrylate with a large number of functional groups, and that it can be improved by using a multifunctional (meth)acrylate with a small number of functional groups. Tensile elongation.

1, 1A, 1B: electronic devices 2: Through the electrode substrate 3: Semiconductor packaging 5: Photosensitive resin varnish 21: Insulation layer 23: Semiconductor wafer 24, 24A, 24B: lower wiring layer 25: Upper wiring layer 26: Solder bumps 27: Structure with chip embedded 31: Package substrate 32: Semiconductor wafer 33: Bonding wire 34: sealing layer 35: Solder bumps 202: Substrate 221: Through wiring 222: Through wiring 251: organic insulating layer 252: Organic insulating layer 253: wiring layer 254: Through wiring 412: mask 423: Opening 424: Opening 2510: photosensitive resin layer 2520: photosensitive resin layer S1: chip configuration steps S2: Upper wiring layer forming step S20: The first resin film configuration step S21: 1st exposure step S22: the first developing step S23: 1st hardening step S24: Wiring layer forming step S25: The second resin film configuration step S26: The second exposure step S27: the second developing step S28: 2nd hardening step S29: Through wiring forming step S3: Substrate peeling step S4: Step of forming the lower wiring layer S5: Solder bump formation step S6: layering step W: diameter

[FIG. 1] It is a longitudinal cross-sectional view which shows an example of the structure of an electronic device. [ Fig. 2 ] is a partially enlarged view of the area surrounded by chain lines in Fig. 1 . [ Fig. 3 ] is a step diagram showing a method of manufacturing the electronic device shown in Fig. 1 . [ FIG. 4 ] is a diagram for explaining a method of manufacturing the electronic device shown in FIG. 1 . [ Fig. 5 ] is a diagram for explaining a method of manufacturing the electronic device shown in Fig. 1 . [ FIG. 6 ] is a diagram for explaining a method of manufacturing the electronic device shown in FIG. 1 .

1: Electronic device

2: Through the electrode substrate

3: Semiconductor packaging

21: Insulation layer

23: Semiconductor wafer

24: Lower wiring layer

25: Upper wiring layer

26: Solder bumps

31: Package substrate

32: Semiconductor wafer

33: Bonding wire

34: sealing layer

35: Solder bumps

221: Through wiring

222: Through wiring

253: wiring layer

Claims (27)

A photosensitive resin composition, which contains: Polyimide (A), having an imide ring structure; Multifunctional (meth)acrylate compound (B); Photosensitizer (C); and solvent (J). Such as the photosensitive resin composition of claim 1, wherein, The number of moles of imide groups contained in the aforementioned polyimide (A) is set as IM, When the number of moles of amide groups contained in the aforementioned polyimide (A) is AM, The imidization rate represented by {IM/(IM+AM)}×100 (%) is 90% or more. The photosensitive resin composition according to claim 1 or 2, wherein the aforementioned polyimide (A) has a structure represented by the following general formula (a),

In general formula (a), X is a divalent organic group, Y is a tetravalent organic group, and at least one of X and Y is a group containing a fluorine atom. The photosensitive resin composition according to claim 1 or 2, wherein, The aforementioned polyimide (A) includes a polyimide containing a fluorine atom. The photosensitive resin composition according to claim 1 or 2, wherein, The aforementioned polyimide (A) has a group capable of reacting with an epoxy group to form a bond at its terminal. The photosensitive resin composition according to claim 1 or 2, wherein, The aforementioned polyimide (A) has an acid anhydride group at its terminal. The photosensitive resin composition according to claim 1 or 2, wherein, The aforementioned polyimide (A) does not have a maleimide structure at its terminal. The photosensitive resin composition according to claim 1 or 2, wherein, The said polyfunctional (meth)acrylate compound (B) contains the (meth)acrylate compound (B1) more than seven functional. The photosensitive resin composition according to claim 1 or 2, wherein, The said polyfunctional (meth)acrylate compound (B) contains the 5-6 functional (meth)acrylate compound (B2). The photosensitive resin composition according to claim 1 or 2, wherein, The said polyfunctional (meth)acrylate compound (B) contains a 3-4 functional (meth)acrylate compound (B3). The photosensitive resin composition according to claim 1 or 2, wherein, The quantity of the said polyfunctional (meth)acrylate compound (B) is 50-150 mass parts with respect to 100 mass parts of said polyimides (A). The photosensitive resin composition according to claim 1 or 2, wherein, The quantity of the said polyfunctional (meth)acrylate compound (B) is 70-120 mass parts with respect to 100 mass parts of said polyimides (A). The photosensitive resin composition according to claim 1 or 2, wherein, The said photosensitizer (C) contains a photoradical generator. The photosensitive resin composition according to claim 1 or 2, which further contains a thermal radical initiator (D). The photosensitive resin composition as claimed in item 14, wherein, The aforementioned thermal radical initiator (D) contains an organic peroxide. The photosensitive resin composition as claimed in item 14, wherein, The quantity of the said thermal radical initiator (D) is 0.1-20 mass parts with respect to 100 mass parts of said polyfunctional (meth)acrylate compounds (B). The photosensitive resin composition according to claim 1 or 2, which further contains epoxy resin (E). The photosensitive resin composition according to claim 17, further comprising a hardening catalyst (F) for the aforementioned epoxy resin (E). The photosensitive resin composition according to claim 1 or 2, which further contains a silane coupling agent (G). The photosensitive resin composition as claimed in item 19, wherein, The aforementioned silane coupling agent (G) includes a silane coupling agent having a cyclic acid anhydride structure. The photosensitive resin composition according to claim 1 or 2, which further contains a surfactant (H). The photosensitive resin composition according to claim 1 or 2, wherein, The ratio of the said polyimide (A) and the said polyfunctional (meth)acrylate compound (B) in the whole composition is 20-50 mass %. The photosensitive resin composition according to claim 1 or 2, which is in the form of a varnish in which at least the polyimide (A) and the polyfunctional (meth)acrylate compound (B) are dissolved in the solvent (J) . The photosensitive resin composition according to claim 1 or 2, which is used to form an insulating layer in an electronic device. A method of manufacturing an electronic device, comprising: A film forming step, using the photosensitive resin composition according to any one of Claims 1 to 24 to form a photosensitive resin film on the substrate; an exposing step of exposing the aforementioned photosensitive resin film; and In the development step, the exposed photosensitive resin film is developed. The method of manufacturing an electronic device according to claim 25, which includes a thermosetting step of heating and curing the exposed photosensitive resin film after the developing step. An electronic device comprising a cured film of the photosensitive resin composition according to any one of claims 1 to 24.

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