JP2019144581A - Photosensitive resin composition, cured film, protective film, insulating film, and electronic device - Google Patents

Abstract

To provide a photosensitive resin composition which suppresses an increase in viscosity as a resin composition and is excellent in development adhesion.SOLUTION: The photosensitive resin composition of the present invention is used for forming a permanent film and contains: (A) a polyamide resin having a structure selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, and a polyimide precursor structure; (B) a photoacid generator; (C) an adhesion aid; and (D) an organic solvent. The organic solvent (D) contains a compound having an ether bond and an amide bond in the molecule.SELECTED DRAWING: None

Description

  The present invention relates to a photosensitive resin composition, a cured film, a protective film, an insulating film, and an electronic device.

  Conventionally, a polyamide resin having a specific structure has been preferably used as a surface protective film or an interlayer insulating film of a semiconductor element because of its high heat resistance, electrical characteristics, and mechanical characteristics. Here, when such a polyamide resin is used as a protective film or an interlayer insulating film of a semiconductor element, it is generally used in a varnish form by dissolving the polyamide resin in an organic solvent from the viewpoint of process efficiency. It was the target.

  In relation to this, the technique disclosed in Patent Document 1 is known. In this document, a photosensitive resin composition in which a polyimide precursor or a polybenzoxazole precursor and a polar solvent having a specific structure are combined is disclosed, and N-methyl- in the photosensitive resin composition is disclosed. It is disclosed that by adjusting the content of 2-pyrrolidone (NMP) to 0.1% by mass or less, a resin composition that does not gel with time change and satisfies the sensitivity and mechanical properties can be obtained. .

International Publication No. 2014/115233 Pamphlet

  Here, as a result of the study by the present inventors, when the solvent disclosed in Example 5 or 6 of Patent Document 1 is used, the resin is used in comparison with N-methyl-2-pyrrolidone (NMP) which is used for general purposes. It has been found that when the composition is developed, the development adhesion decreases.

  As a result of diligent investigation based on such knowledge, by using an organic solvent containing a compound having an ether bond and an amide bond in the molecule and an adhesion aid, a photosensitivity containing a polyamide resin and a photoacid generator is used. It has been found that the resin composition can suppress the increase in viscosity and improve the development adhesiveness while obtaining good patternability. Further, it has been found that when the photosensitive resin composition is used for forming a permanent film, the occurrence of cracks during rewiring can be suppressed. With such a composition, in the photosensitive resin composition, it has been found that the patterning property and the development adhesion are improved, and the suppression of the increase in viscosity and the occurrence of cracks during rewiring is improved, and the present invention has been completed. It was.

According to the present invention,
A photosensitive resin composition used to form a permanent film,
(A) Polyamide resin having a structure selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, and a polyimide precursor structure (B) photoacid generator (C) adhesion aid (D) organic A photosensitive resin composition containing a solvent, wherein the organic solvent (D) contains a compound having an ether bond and an amide bond in the molecule is provided.

  Moreover, according to this invention, the cured film comprised with the hardened | cured material of said photosensitive resin composition is provided.

  Moreover, according to this invention, the protective film comprised with said cured film is provided.

  Moreover, according to this invention, the insulating film comprised with said cured film is provided.

  Moreover, according to this invention, an electronic apparatus provided with said cured film is provided.

  According to the present invention, it is possible to provide a photosensitive resin composition used for forming a permanent film, which is excellent in patterning property and development adhesiveness, and can suppress an increase in viscosity and crack generation during rewiring. .

  The above-described object and other objects, features, and advantages will become more apparent from the preferred embodiments described below and the accompanying drawings.

It is sectional drawing which shows an example of the electronic device which concerns on this embodiment.

  Hereinafter, embodiments will be described with reference to the drawings as appropriate. In all the drawings, the same reference numerals are given to the same components, and the description will be omitted as appropriate. In addition, unless otherwise specified, “to” represents the following.

[Photosensitive resin composition]
The photosensitive resin composition according to this embodiment is a photosensitive resin composition used for forming a permanent film, and includes the following components.
(A) Polyamide resin having a structure selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, and a polyimide precursor structure (B) photoacid generator (C) adhesion aid (D) organic Solvent Here, (D) the organic solvent is characterized by containing a compound having an ether bond and an amide bond in the molecule.

First, the use of the photosensitive resin composition according to the present embodiment will be described.
The photosensitive resin composition of the present embodiment is used for forming a permanent film. By using the photosensitive resin composition as a cured product, a cured film constituting a permanent film can be obtained. In this embodiment, for example, after a coating film composed of a photosensitive resin composition is patterned into a desired shape by exposure and development, a cured film (permanent film) is formed by curing the coating film by heat treatment or the like. Is done.
In this embodiment, the organic solvent (D) containing a compound having an ether bond and an amide bond in the molecule has little damage to the cured film of the photosensitive resin composition and can suppress the occurrence of cracks in the cured film. There is also an accompanying effect that it can be done.

  Examples of the cured film (permanent film) formed using the photosensitive resin composition include a protective film, an interlayer insulating film (insulating film), and a dam material. The use of the permanent film is not limited to this, but in one embodiment, the use as a film having a high light blocking property against visible light, such as a color filter and a black matrix, may not be included.

  The protective film is formed on the surface of an electronic component or an electronic device, refers to a film for protecting the surface of the electronic component or the electronic device, and the type thereof is not particularly limited. Examples of such a protective film include a passivation film or a buffer coat layer provided on a semiconductor element, or a cover coat provided on a flexible substrate.

The interlayer insulating film refers to an insulating film provided in a multilayer structure, and the kind thereof is not particularly limited. Examples of the interlayer insulating film include those used in semiconductor device applications such as an interlayer insulating film constituting a multilayer wiring structure of a semiconductor element and a buildup layer or a core layer constituting a circuit board. Further, as the interlayer insulating film, for example, a flattening film that covers a thin film transistor (TFT) in the display device, a liquid crystal alignment film, and an MVA (Multi Domain Vertical Alignment) liquid crystal display device color filter substrate are provided. The thing used in display apparatus uses, such as a protrusion for forming a protrusion or the cathode of an organic EL element, is also mentioned.
The dam material is a spacer used to form a hollow portion for arranging an optical element or the like on the substrate.

  Next, each component constituting the photosensitive resin composition according to this embodiment will be described.

((A) Polyamide resin)
The (A) polyamide resin (hereinafter also referred to as (A) amide resin) used in the present embodiment has a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, and a polyimide precursor structure. A structure selected from the group is provided in the resin structure.
This (A) polyamide resin has, for example, a hydroxyl group, particularly a phenolic hydroxyl group and / or a carboxyl group, in its main chain or side chain, and has a polybenzoxazole structure, a polybenzoxazole precursor structure, and a polyimide structure. Any of the polyimide precursor structures is included in the resin structure.
In addition, these resin components can be used 1 type or in mixture of 2 or more types.

More specifically, as the (A) polyamide resin, a resin having a benzoxazole precursor structure and / or an imide precursor structure is preferably used.
The (A) polyamide resin may have a benzoxazole structure generated by a ring-closing reaction of a part of the benzoxazole precursor structure or an imide structure generated by a ring-closing reaction of a part of the imide precursor structure. It may also have an amic acid ester structure.

  The specific benzoxazole precursor structure refers to the structure represented by the following general formula (6), the imide precursor structure refers to the structure represented by the following general formula (7), and the benzoxazole structure is , Refers to the structure represented by the following general formula (8), the imide structure refers to the structure represented by the following general formula (9), the amidic acid ester structure is represented by the following general formula (10) Refers to the structure.

  In the above formulas (6) to (10), D represents a divalent or trivalent organic group, and R ′ represents a monovalent organic group. Among these polyamide resins, a polyamide resin having a repeating unit represented by the following general formula (11) is preferable from the viewpoint of heat resistance of the cured product of the photosensitive resin composition of the present embodiment.

（式（１１）中、Ｘ、Ｙは、有機基である。Ｒ_２は、水酸基、−Ｏ−Ｒ_４、アルキル基、アシルオキシ基又はシクロアルキル基であり、複数有する場合、それぞれ同一であっても異なってもよい。Ｒ_３は、水酸基、カルボキシル基、−Ｏ−Ｒ_４又は−ＣＯＯ−Ｒ_４であり、複数有する場合、それぞれ同一であっても異なってもよい。Ｒ_２及びＲ_３におけるＲ_４は、炭素数１〜１５の有機基である。ここで、式（１１）において、Ｒ_２に、水酸基がない場合は、Ｒ_３の少なくとも１つはカルボキシル基である。また、Ｒ_３に、カルボキシル基がない場合は、Ｒ_２の少なくとも１つは水酸基である。ｋは０〜８の整数、ｌは０〜８の整数である。ｅは２〜１００の整数である。）

(In formula (11), X and Y are organic groups. R ₂ is a hydroxyl group, —O—R ₄ , an alkyl group, an acyloxy group, or a cycloalkyl group, good .R ₃ also be different, a hydroxyl group, a carboxyl group, an _{-O-R 4} or _{-COO-R 4,} in the case, good .R ₂ and _{R 3} may each be the same or different plural having R ₄ is an organic group having 1 to 15 carbon atoms. here, in equation (11), the _{R 2,} when there is no hydroxyl group, at least one of _{R 3} is carboxyl group. Further, _{R 3} In the case where no carboxyl group is present, at least one of R ₂ is a hydroxyl group, k is an integer of 0 to 8, l is an integer of 0 to 8, and e is an integer of 2 to 100.)

In the polyamide resin having the structure represented by the general formula (11), as R ₂ and R ₃ , the hydroxyl group and the carboxyl group are protected with a protecting group R ₄ in order to adjust the solubility of the polyamide resin in an alkaline aqueous solution. In particular, —O—R ₄ as R ₂ , —O—R ₄ and —COO—R ₄ as R ₃ can be used. Examples of the organic group having 1 to 15 carbon atoms as R ₄ include formyl group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, tertiary butoxycarbonyl group, phenyl group, benzyl group, Examples include a tetrahydrofuranyl group and a tetrahydropyranyl group.

  The organic group as X of the polyamide resin having the structure represented by the general formula (11) is not particularly limited, but for example, an aromatic group having a structure such as a benzene ring, a naphthalene ring, and a bisphenol structure. A heterocyclic organic group having a structure such as a pyrrole ring or a furan ring; a siloxane group; More specifically, what is represented by following formula (12) is preferable. These may be used alone or in combination of two or more.

（式（１２）中、＊は、一般式（１１）におけるＮＨ基に結合することを示す。Ｚは、アルキレン基、置換アルキレン基、−Ｏ−Ｃ_６Ｈ_４−Ｏ−、−Ｏ−、−Ｓ−、−ＳＯ_２−、−Ｃ（＝Ｏ）−、−ＮＨＣ（＝Ｏ）−または単結合である。Ｒ_５は、アルキル基、アルキルエステル基及びハロゲン原子から選ばれた１つを示し、それぞれ同一であっても異なっていてもよい。Ｒ_６は、水素原子、アルキル基、アルキルエステル基及びハロゲン原子から選ばれた１つを示す。ｕは０〜４の整数である。Ｒ_７〜Ｒ_１０はそれぞれ１価または２価の有機基である。
なお、上記式（１２）において、上記一般式（１１）におけるＸの置換基Ｒ_２は省略している。）

(In formula (12), * represents bonding to the NH group in general formula (11). Z represents an alkylene group, a substituted alkylene group, —O—C ₆ H ₄ —O—, —O—, —S—, —SO ₂ —, —C (═O) —, —NHC (═O) — or a single bond, R ₅ represents one selected from an alkyl group, an alkyl ester group and a halogen atom; R ₆ represents one selected from a hydrogen atom, an alkyl group, an alkyl ester group and a halogen atom, and u is an integer of 0 to 4. _{7 to} R ₁₀ are each a monovalent or divalent organic group.
In the above formula (12), the substituent R ₂ of X in the above general formula (11) is omitted. )

Particularly preferred among the groups represented by the above formula (12) are those represented by the following formula (13) (some of them have R ₂ in the general formula (11)).

（式（１３）中、＊は一般式（１１）におけるＮＨ基に結合することを示す。式中Ｚは、アルキレン基、置換アルキレン基、−Ｏ−、−Ｓ−、−ＳＯ_２−、−Ｃ（＝Ｏ）−、−ＮＨＣ（＝Ｏ）−、−ＣＨ_３−、−Ｃ（ＣＨ_３）Ｈ−、−Ｃ（ＣＨ_３）_２−、−Ｃ（ＣＦ_３）_２−、又は単結合である。Ｒ_１１は、アルキル基、アルコキシ基、アシルオキシ基及びシクロアルキル基から選ばれる１つであり、Ｒ_１１が複数ある場合、それぞれ同じでも異なってもよい。ｖは０以上３以下の整数である。）

(In formula (13), * indicates bonding to the NH group in formula (11). In the formula, Z represents an alkylene group, a substituted alkylene group, —O—, —S—, —SO ₂ —, — _{C (= O) -, -} NHC (= O) -, - CH 3 -, - C (CH 3) H -, - C (CH 3) 2 -, - C (CF 3) 2 -, or a single bond R ₁₁ is one selected from an alkyl group, an alkoxy group, an acyloxy group, and a cycloalkyl group, and when there are a plurality of R _{11 s} , they may be the same or different, and v is an integer of 0 or more and 3 or less. .)

Particularly preferred among the groups represented by the above formula (13) are those represented by the following formula (14) (some of them have R ₂ in the general formula (11)).

（式（１４）中、＊は一般式（１１）におけるＮＨ基に結合することを示す。Ｒ_１２はアルキレン基、置換アルキレン基、−Ｏ−、−Ｓ−、−ＳＯ_２−、−Ｃ（＝Ｏ）−、−ＮＨＣ（＝Ｏ）−、―Ｃ（ＣＦ_３）_２―、単結合から選ばれる有機基である。）

(In formula (14), * represents bonding to the NH group in formula (11). R ₁₂ represents an alkylene group, a substituted alkylene group, —O—, —S—, —SO ₂ —, —C ( ═O) —, —NHC (═O) —, —C (CF ₃ ) ₂ —, an organic group selected from a single bond.

Specific examples of the alkylene group and substituted alkylene group as Z in the above formula (12) and formula (13) and R ₁₂ in the above formula (14) include —CH ₂ —, —CH (CH ₃ ) —, _{-C (CH 3) 2 -,} - CH (CH 2 CH 3) -, - C (CH 3) (CH 2 CH 3) -, - C (CH 2 CH 3) (CH 2 CH 3) -, - _{CH (CH 2 CH 2 CH 3} ) -, - C (CH 3) (CH 2 CH 2 CH 3) -, - CH (CH (CH 3) 2) -, - C (CH 3) (CH (CH 3 _{) 2) -, - CH (} CH 2 CH 2 CH 2 CH 3) -, - C (CH 3) (CH 2 CH 2 CH 2 CH 3) -, - CH (CH 2 CH (CH 3) 2) - _{, -C (CH 3) (CH} 2 CH (CH 3) 2) -, - CH (CH 2 CH 2 C _{2 CH 2 CH 3) -,} - C (CH 3) (CH 2 CH 2 CH 2 CH 2 CH 3) -, - CH (CH 2 CH 2 CH 2 CH 2 CH 2 CH 3) - and -C (CH _{3) (CH 2 CH 2 CH} 2 CH 2 CH 2 CH 3) - , and the like. Among these, —CH ₂ —, —CH (CH ₃ ) —, —C (CH ₃ ) ₂ — has sufficient solubility in not only an alkaline aqueous solution but also a solvent, and a polyamide having a better balance. Since resin can be obtained, it is preferable.

  Y in the polyamide resin having the structure represented by the general formula (11) is an organic group. Examples of such an organic group include the same groups as those described above for X. For example, the organic group includes an aromatic group having a structure such as a benzene ring, a naphthalene ring and a bisphenol structure; a heterocyclic organic group having a structure such as a pyrrole ring, a pyridine ring and a furan ring; a siloxane group, and the like. More specifically, those represented by the following formula (15) can be used. These may be used alone or in combination of two or more.

（式（１５）中、＊は、一般式（１１）におけるＣ＝Ｏ基に結合することを示す。Ｊは、−ＣＨ_２−、−Ｃ（ＣＨ_３）_２−、−Ｏ−、−Ｓ−、−ＳＯ_２−、−Ｃ（＝Ｏ）−、−ＮＨＣ（＝Ｏ）−、−Ｃ（ＣＦ_３）_２−または単結合である。Ｒ_１３は、アルキル基、アルキルエステル基、アルキルエーテル基、ベンジルエーテル基及びハロゲン原子から選ばれた１つを示し、それぞれ同じでも異なってもよい。Ｒ_１４は、水素原子、アルキル基、アルキルエステル基及びハロゲン原子から選ばれた１つを示す。ｗは０以上２以下の整数である。Ｒ_１５〜Ｒ_１８はそれぞれ１価または２価の有機基である。
なお、上記式（１５）において、上記一般式（１１）におけるＹの置換基Ｒ_３は省略している。）

(In the formula (15), * indicates that it is bonded to the C═O group in the general formula (11). J represents —CH ₂ —, —C (CH ₃ ) ₂ —, —O—, —S. —, —SO ₂ —, —C (═O) —, —NHC (═O) —, —C (CF ₃ ) ₂ — or a single bond, R ₁₃ represents an alkyl group, an alkyl ester group, an alkyl ether. R ₁₄ represents one selected from a hydrogen atom, an alkyl group, an alkyl ester group and a halogen atom, each of which may be the same or different. w is an integer of 0 to 2. R _{15 to} R ₁₈ are each a monovalent or divalent organic group.
In the above formula (15), the substituent R ₃ for Y in the above general formula (11) is omitted. )

Among these groups represented by the formula (15), those particularly preferred are those represented by the following formula (16) (some of them have R ₃ in the general formula (11)).
Regarding the structure derived from tetracarboxylic dianhydride in the following formula (16), mention is made of those in which both the positions bonded to the C═O group in the general formula (11) are in the meta position and both are in the para position. However, it may have a structure including a meta position and a para position.

(In the formula (16), * indicates bonding to the C═O group in the general formula (11). R ₁₉ is an alkyl group, an alkyl ester group, an alkyl ether group, a benzyl ether group, and a halogen atom. Each of which may be the same or different, and R ₂₀ represents one selected from a hydrogen atom or an organic group having 1 to 15 carbon atoms, and may be partially substituted. X is an integer from 0 to 2.

In the case of the polyamide resin represented by the general formula (11), the terminal amino group of the polyamide resin is substituted with an alkenyl group to the extent that it does not affect the mechanical properties and heat resistance of the cured product cured at low temperature. The end-capping can also be performed as an amide using an acid anhydride or monocarboxylic acid containing an aliphatic group or a cyclic compound group having at least one organic group selected from an alkynyl group and a hydroxyl group.
Examples of the acid anhydride or monocarboxylic acid containing an aliphatic group or cyclic compound group having at least one organic group selected from the alkenyl group, alkynyl group and hydroxyl group include maleic anhydride, citraconic anhydride, and the like. , 2,3-dimethylmaleic anhydride, 4-cyclohexene-1,2-dicarboxylic anhydride, exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride, 5-norbornene -2,3-dicarboxylic acid anhydride, methyl-5-norbornene-2,3-dicarboxylic acid anhydride, itaconic acid anhydride, het acid anhydride, 5-norbornene-2-carboxylic acid, 4-ethynylphthalic acid anhydride And 4-phenylethynylphthalic anhydride, 4-hydroxyphthalic anhydride, 4-hydroxybenzoic acid, 3-hydroxybenzoic acid, etc. Rukoto can. These may be used alone or in combination of two or more, and a part of the end-capped amide moiety may be dehydrated and closed.

  In addition, the method is not limited to this, and the terminal carboxylic acid residue contained in the polyamide resin is an aliphatic group having at least one organic group selected from an alkenyl group, an alkynyl group, and a hydroxyl group, or An amine derivative containing a cyclic compound group can be used to end-cleave as an amide.

Furthermore, in the case of the polyamide resin represented by the general formula (11), at least one of the terminals is end-capped with a nitrogen-containing cyclic compound to the extent that it does not affect the mechanical properties and heat resistance of the cured product cured at low temperature. It may have a stopped group. Thereby, adhesiveness with a metal wiring (for example, copper wiring) etc. can be improved.
Examples of the nitrogen-containing cyclic compound include 1- (5-1H-triazoyl) methylamino group, 3- (1H-pyrazoyl) amino group, 4- (1H-pyrazoyl) amino group, and 5- (1H-pyrazoyl) amino. Group, 1- (3-1H-pyrazolyl) methylamino group, 1- (4-1H-pyrazoyl) methylamino group, 1- (5-1H-pyrazolyl) methylamino group, (1H-tetrazol-5-yl) An amino group, 1- (1H-tetrazol-5-yl) methyl-amino group, 3- (1H-tetrazol-5-yl) benz-amino group and the like can be mentioned.

The polyamide resin having the structure represented by the general formula (11) is, for example, a compound selected from diamine, bis (aminophenol), 2,4-diaminophenol and the like containing X in the general formula (11) Can be synthesized by reacting Y and a compound selected from tetracarboxylic dianhydride, trimellitic anhydride, dicarboxylic acid, dicarboxylic acid dichloride, dicarboxylic acid derivative, and the like.
In the case of using dicarboxylic acid, an active ester type dicarboxylic acid derivative obtained by reacting 1-hydroxy-1,2,3-benzotriazole or the like with dicarboxylic acid in advance in order to increase the reaction yield of the polyamide resin. May be used.

  The polyamide resin having the structure represented by the general formula (11) is heated and dehydrated and closed to obtain a heat-resistant resin in the form of polyimide resin, polybenzoxazole resin, or copolymerization of both. In addition, as temperature which performs dehydration ring closure, when heating at high temperature, it can process at 280 to 380 degreeC, and when heating at low temperature, it can process at 150 to 280 degreeC.

Regarding the (A) polyamide resin contained in the photosensitive resin composition of the present embodiment, when this photosensitive resin composition is used for a certain application, (A) inclusion of halogen atoms in the structure of the polyamide resin Preferably the amount is limited.
More specifically, the fluorine content measured by elemental analysis of the (A) polyamide resin is preferably 8 wt% or less, more preferably 5 wt% or less.
In addition, the halogen content of the (A) polyamide resin measured by elemental analysis is preferably 8 wt% or less, and more preferably 5 wt% or less.
Here, the halogen content refers to the total content of fluorine, chlorine, bromine and iodine in the (A) polyamide resin.
Here, it is known that the inclusion of halogen atoms as described above in the (A) polyamide resin usually increases the solubility in organic solvents. However, since the (D) organic solvent used in the present embodiment has high solubility in such a polyamide resin, the (A) organic solvent is sufficiently dissolved even if it does not contain a halogen atom as the polyamide resin component. be able to.

((B) Photoacid generator)
The photosensitive resin composition of the present embodiment includes (B) a photoacid generator.
Examples of the photoacid generator (B) include photosensitive diazoquinone compounds, diaryliodonium salts, triarylsulfonium salts, onium salts such as sulfonium borate salts, 2-nitrobenzyl ester compounds, N-iminosulfonate compounds, imidosulfonates. A compound, a 2,6-bis (trichloromethyl) -1,3,5-triazine compound, or a dihydropyridine compound can be used. Among these, it is particularly preferable to use a photosensitive diazoquinone compound having excellent sensitivity and solvent solubility. As the photosensitive diazoquinone compound, for example, those shown below can be used.

（ｎ２は、１以上、５以下の整数である）

(N2 is an integer of 1 or more and 5 or less)

  In each of the above compounds, Q is any one of the structures shown in the following (a) to (c), or a hydrogen atom. However, at least one of Q of each compound has one of the structures shown in the following (a) to (c).

  In the present embodiment, as the photosensitive diazoquinone compound, for example, an ester of a phenol compound and 1,2-naphthoquinone-2-diazide-5-sulfonic acid or 1,2-naphthoquinone-2-diazide-4-sulfonic acid It is more preferable to use When the photosensitive resin composition is a positive type, the photosensitive agent remaining in the relief pattern in the unexposed area is considered to be decomposed by heat at the time of curing to generate an acid, and (B) light as a reaction accelerator. Acid generators play an important role. As the photosensitive diazoquinone compound having such a role, it is particularly preferable to use an ester of 1,2-naphthoquinone-2-diazido-4-sulfonic acid which is easily decomposed by heat.

  Although content of (B) photo-acid generator in the photosensitive resin composition of this embodiment is not specifically limited, It is 5 mass parts or more with respect to 100 mass parts of (A) polyamide resin. Is more preferable, and it is more preferable that it is 8 mass parts or more. In addition, the content of the (B) photoacid generator in the photosensitive resin composition is preferably 40 parts by mass or less, and 30 parts by mass or less with respect to 100 parts by mass of the (A) polyamide resin. More preferred. (B) Good patterning performance can be exhibited because the content of the photoacid generator is within the above range.

((C) Adhesion aid)
In the photosensitive resin composition of this embodiment, (C) adhesion assistant is contained.
The (C) adhesion assistant used here is a component having a function of improving the bond strength between the coating film obtained by curing the photosensitive resin composition and the substrate on which the coating film is formed.
Examples of such (C) adhesion assistant include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and p-styryltrimethoxy. Silane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N- 2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropyltriethoxysilane, 3 -Aminopropyltrime Xysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis (triethoxypropyl) tetrasulfide, 3-isocyanate Examples thereof include, but are not limited to, propyltriethoxysilane, a silicon compound obtained by reacting an amino group-containing silicon compound with an acid dianhydride or an acid anhydride.
Among these compounds, a silicon compound obtained by reacting an amino group-containing silicon compound with an acid dianhydride or an acid anhydride has an intramolecular structure when the acid dianhydride or acid anhydride is ring-opened. To form a carboxyl group.
Thus, as (C) the adhesion aid, by including at least one carboxyl group in the molecule, while exhibiting an appropriate affinity with a compound having an ether bond and an amide bond in the molecule described later. The adhesion of the cured product of the photosensitive resin composition to the substrate can be improved. That is, in the photosensitive resin composition of the present embodiment, by using together (C) an adhesion assistant and (D) an organic solvent containing a compound having an ether bond and an amide bond in the molecule, the viscosity increase rate is also increased. It is low, has excellent patterning and development adhesion, and can suppress the occurrence of cracks in the cured film.

The type of silicon compound having an amino group is not particularly limited as long as adhesion can be improved. For example, 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3 -Aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltriethoxysilane and the like.
The acid dianhydride or acid anhydride is not particularly limited as long as the adhesion can be improved. For example, 3,3 ′, 4,4′-benzophenonetetracarboxylic acid anhydride And cyclohexene dicarboxylic acid anhydride, maleic anhydride, chloromaleic anhydride, cyanomaleic anhydride, cytoconic acid, phthalic anhydride, and the like. Moreover, in using, it can be used individually or in combination of 2 or more types.

The content of (C) the adhesion assistant in the photosensitive resin composition of the present embodiment is not particularly limited, but is 0.01 parts by mass or more with respect to 100 parts by mass of (A) polyamide resin. The amount is preferably 0.1 parts by mass or more.
In addition, the content of the (C) adhesion assistant in the photosensitive resin composition is preferably 20 parts by mass or less and more preferably 10 parts by mass or less with respect to 100 parts by mass of the (A) polyamide resin. preferable. (C) When content of adhesion | attachment adjuvant is in the said range, the adhesiveness with a board | substrate and the preservability of the photosensitive resin composition can be improved with good balance.

((D) Organic solvent)
The photosensitive resin composition of the present embodiment is usually used by dissolving the above-described components in (D) an organic solvent and forming a varnish.
The photosensitive resin composition of the present embodiment is characterized in that the (D) organic solvent includes a compound having an ether bond and an amide bond in the molecule.

As described above, (D) by containing a compound having an ether bond and an amide bond in the molecule as an organic solvent, the increase in the viscosity of the photosensitive resin composition is suppressed, and the occurrence of cracks in the cured film is suppressed. Can do.
The reason for this is not clear, but the polarity brought about by the above-mentioned two types of bonds in the molecule exhibits an appropriate affinity for (B) the photoacid generator, and (B) the photoacid generator due to heat, etc. It is thought that it suppresses the decomposition of.
Further, for example, compared to an organic solvent having only an amide bond such as N-methyl-2-pyrrolidone, (A) the load of damage to the amide resin is reduced, so that the occurrence of cracks in the cured film can be suppressed. it can.

  More specifically, as a compound having an ether bond and an amide bond in the molecule, a compound represented by the following general formula (1) can be preferably used.

（式（１）中、Ｒ_１、Ｒ_２、Ｒ_３はそれぞれ炭素数１から１０のアルキル基である。）

(In formula (1), R ₁ , R ₂ and R ₃ are each an alkyl group having 1 to 10 carbon atoms.)

Here, as the alkyl group of R ₁ , R ₂ and R ₃ in the formula (1), a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a pentyl group, A hexyl group, a heptyl group, an octyl group, or the like can be employed.

In addition, the photosensitive resin composition of this embodiment can use together the compound normally used as a solvent other than the compound which has an ether bond and an amide bond in the above-mentioned molecule | numerator as (D) organic solvent. .
Such compounds include N-methyl-2-pyrrolidone, γ-butyrolactone, N, N-dimethylacetamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether. , Propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate, butyl lactate, methyl-1,3-butylene glycol acetate, 1,3-butylene glycol-3-monomethyl ether, methyl pyruvate, and ethyl pyruvate and methyl-3 -Methoxypropionate etc. are mentioned.
Of these compounds, γ-butyrolaclone, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether are among these compounds from the viewpoint of significantly suppressing the occurrence of cracks in the cured film. In a preferred embodiment, a compound selected from the group consisting of propylene glycol monomethyl ether acetate is used in combination.
In the present embodiment, as the organic solvent (D), a compound having an ether bond and an amide bond in the molecule can be used in combination with another solvent as described above. Thereby, the usable solvent species can be increased. For this reason, the solubility of the (D) organic solvent with respect to various melt | dissolution components can be improved, implement | achieving the effect of the photosensitive resin composition of this embodiment.

Further, (D) the content of the compound having an ether bond and an amide bond in the molecule in the organic solvent is preferably 25% by mass or more, and more preferably 40% by mass or more.
By setting the content of the compound having an ether bond and an amide bond in the molecule in this way, it can contribute more significantly to the suppression of the viscosity increase of the photosensitive resin composition and the generation of cracks in the cured film. it can.
Further, (D) the upper limit of the content of the compound having an ether bond and an amide bond in the molecule in the organic solvent is not particularly limited, and (D) all of the organic solvent is composed of the ether bond and the amide bond. It may be a compound having
Alternatively, in view of the solubility of the (A) amide resin, for example, the content of the compound having an ether bond and an amide bond in the organic solvent (D) can be set to 95% by mass or less.

The content of the organic solvent (D) in the photosensitive resin composition of the present embodiment is not particularly limited, but is preferably 100 parts by mass or more with respect to 100 parts by mass of the (A) polyamide resin. 150 parts by mass or more is more preferable.
The content of the organic solvent (D) in the photosensitive resin composition is preferably 1000 parts by mass or less and more preferably 800 parts by mass or less with respect to 100 parts by mass of the (A) polyamide resin. . (D) When the content of the organic solvent is within the above range, appropriate handling properties can be provided.

(Other ingredients)
The photosensitive resin composition of this embodiment can mix | blend the various components used as a photosensitive resin composition other than the component mentioned above. For example, components other than the above-mentioned (A) polyamide resin can be used in combination as the alkali-soluble resin.
Examples of such alkali-soluble resins include acrylic resins such as phenol resins, phenol aralkyl resins, hydroxystyrene resins, methacrylic acid resins, and methacrylic ester resins, and cyclic olefin resins.
In addition, you may add additives, such as antioxidant, a filler, surfactant, a photoinitiator, terminal blocker, and a sensitizer, as needed.
In addition, the quantity which can add these is arbitrary.

  As described above, the resin film (cured film) obtained by curing the photosensitive resin composition of the present embodiment can constitute a permanent film such as a protective film, an interlayer film, or a dam material. Thereby, durability etc. can be improved about the electronic device provided with the said cured film as a permanent film.

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

A rewiring layer 40 is provided on the passivation film 32. The rewiring layer 40 includes an insulating layer 42 provided on the passivation film 32, a rewiring 46 provided on the insulating layer 42, an insulating layer 44 provided on the insulating layer 42 and the rewiring 46, Have An opening connected to the uppermost layer wiring 34 is formed in the insulating layer 42. The rewiring 46 is formed on the insulating layer 42 and in an opening provided in the insulating layer 42, and is connected to the uppermost layer wiring 34. The insulating layer 44 is provided with an opening connected to the rewiring 46.
In the present embodiment, one or more of the passivation film 32, the insulating layer 42, and the insulating layer 44 can be configured by a cured film formed by curing, for example, the above-described photosensitive resin composition. In this case, for example, the passivation film 32, the insulating layer 42, or the insulating layer 44 is formed by patterning by exposing the coating film formed of the photosensitive resin material to ultraviolet rays and performing development, followed by patterning by heating. It is formed.

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

  It should be noted that the present invention is not limited to the above-described embodiments, and modifications, improvements, and the like within the scope that can achieve the object of the present invention are included in the present invention.

Next, examples of the present invention will be described.
First, each material used in the examples was prepared as shown below.

(Synthesis of amide resin (A-1))
40.87 g (0.083 mol) of a dicarboxylic acid derivative obtained by reacting 1 mol of diphenyl ether-4,4′-dicarboxylic acid with 2 mol of 1-hydroxybenzotriazole and 2,2-bis (3-amino- 4-hydroxyphenyl) propane (25.82 g, 0.1 mol) was placed in a four-necked separable flask equipped with a thermometer, stirrer, raw material inlet, and dry nitrogen gas inlet tube, and N-methyl-2- 3000 g of pyrrolidone was added and dissolved. Thereafter, the mixture was reacted at 75 ° C. for 12 hours using an oil bath. Next, 6.98 g (0.0425 mol) of 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride dissolved in 34.88 g of N-methyl-2-pyrrolidone was added. The reaction was terminated by stirring for 3 hours.
Next, after filtering the reaction mixture, the reaction mixture was put into a solution of water / isopropyl alcohol = 3/1, the precipitate was collected by filtration, washed thoroughly with water, dried under vacuum, and the repetition shown below An amide resin which is an alkali-soluble resin having a unit (resin that is dehydrated and ring-closed when heated at 300 to 400 ° C. to become polybenzoxazole) was obtained.

The obtained amide resin (A-1) had the repeating units shown below, the weight average molecular weight (Mw) was 14300, the number average molecular weight (Mn) was 9730, and Mw / Mn was 1.47. . The fluorine content measured by elemental analysis was 0 wt%.

(Synthesis of amide resin (A-2))
Into a four-necked glass separable flask equipped with a thermometer, a stirrer, a raw material charging port and a dry nitrogen gas inlet tube, 21.2 g (0. 0. 2,2-bis (3-amino-4-hydroxyphenyl) propane was added. 082 mol) was added, and 400 ml of acetone was added and dissolved. Next, 33.4 g (0.18 mol) of para-nitrobenzoyl chloride dissolved in 100 mL of acetone was added dropwise over 30 minutes while cooling so that the temperature was less than 20 ° C. to obtain a mixture. After the addition, the temperature of the mixture was heated to 40 ° C. and stirred for 2 hours, and then 30.0 g (0.218 mol) of potassium carbonate was gradually added and further stirred for 2 hours. Heating was stopped and the mixture was further stirred at room temperature for 18 hours. Thereafter, while vigorously stirring the mixture, an aqueous sodium hydroxide solution was gradually added. After the addition, the mixture was heated to 55 ° C. and further stirred for 30 minutes. After completion of the stirring, the mixture was cooled to room temperature, 37% by weight hydrochloric acid aqueous solution and 500 ml of water were added, and the pH of the solution was adjusted to be in the range of 6.0 to 7.0. Next, the resulting precipitate is filtered off, and the filtrate is washed with water and dried at 60 to 70 ° C. to obtain bis-N, N ′-(para-nitrobenzoyl) -2,2-bis. A solid of (4-hydroxyphenyl) propane was obtained.
To 41.9 g of the obtained solid, 316 g of acetone and 158 g of methanol were added and heated to 50 ° C. to be completely dissolved. Thereto, 300 mL of pure water at 50 ° C. was added over 30 minutes and heated to 65 ° C. Thereafter, the precipitate was slowly cooled to room temperature, and the precipitated crystal was filtered, and the crystal was purified by drying at 70 ° C. to obtain bis-N, N ′-(para-nitrobenzoyl) -2,2-bis (4 -Hydroxyphenyl) propane was obtained.
Into a 1 L flask, 20 g of the bis-N, N ′-(para-nitrobenzoyl) -2,2-bis (4-hydroxyphenyl) propane obtained above was placed and 1.0 g of 5% palladium-carbon catalyst and acetic acid. 180.4 g of ethyl was added to make a suspension. Hydrogen gas was purged there, and the mixture was shaken for 35 minutes while being heated to 50 to 55 ° C. to carry out a reduction reaction. After completion of the reaction, it was cooled to 35 ° C. and the suspension was purged with nitrogen. After removing the catalyst by filtration, the filtrate was subjected to an evaporator to evaporate the solvent. The obtained product was dried at 90 ° C. to obtain bis-N, N ′-(para-aminobenzoyl) -2,2-bis (4-hydroxyphenyl) propane.
To a 300 mL flask, 11.91 g (0.024 mol) of bis-N, N ′-(para-aminobenzoyl) -2,2-bis (4-hydroxyphenyl) propane and 40 g of γ-butyrolactone were added and stirred. Cooled to ° C. Thereto were added 6.82 g (0.022 mol) of 4,4′-oxydiphthalic anhydride and 12.0 g of γ-butyrolactone, and the mixture was stirred at 20 ° C. for 1.5 hours. Thereafter, the mixture was heated to 50 ° C. and stirred for 3 hours, and then 5.24 g (0.044 mol) of N, N-dimethylformamide dimethylacetal and 10.0 g of γ-butyrolactone were added, and the mixture was further stirred at 50 ° C. for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature to obtain an amide resin (resin that dehydrated and ring-closed when heated at 300 to 400 ° C. to be polyimide benzoxazole), which is an alkali-soluble resin having the following repeating units.

  The obtained amide resin (A-2) has the following repeating units, and the weight average molecular weight (Mw) was 15420, the number average molecular weight (Mn) was 10550, and Mw / Mn was 1.46. . The fluorine content measured by elemental analysis was 0 wt%.

Ｒ_２１は、水素原子または−ＣＨ_３を示す。

R ₂₁ represents a hydrogen atom or —CH ₃ .

(Synthesis of photoacid generator (B-1))
In a four-necked separable flask equipped with a thermometer, a stirrer, a raw material inlet, and a dry nitrogen gas inlet tube, 11.04 g (0.026 mol) of phenol represented by the formula (P-1), 2-Naphthoquinone-2-diazide-4-sulfonyl chloride 18.81 g (0.070 mol) and acetone 170 g were added under a dry nitrogen stream condition and stirred to dissolve.
Next, a mixed solution of 7.78 g (0.077 mol) of triethylamine and 5.5 g of acetone was slowly added dropwise while cooling the flask with a water bath so that the temperature of the reaction solution did not exceed 35 ° C. After reacting for 3 hours at room temperature, 1.05 g (0.017 mol) of acetic acid was added, and the reaction was further continued for 30 minutes. Subsequently, after filtering the reaction mixture, the filtrate was put into a mixed solution of water / acetic acid (990 ml / 10 ml). Next, the precipitate was collected by filtration, thoroughly washed with water, and then dried under vacuum. This obtained the photo-acid generator (B-1) represented by the structure of Formula (Q-1).

(Adhesion aid (C-1))
The following adhesion assistant (C-1) was prepared.

(Adhesion aid (C-2))
The following adhesion assistant (C-2) was prepared.

(Organic solvent (D-1))
The following Examide (registered trademark) B-100 manufactured by Idemitsu Kosan Co., Ltd. was prepared as an organic solvent (D-1).

(Organic solvents (D-2, D-3))
Γ-Butyrolactone was prepared as the organic solvent (D-2), and N-methyl-2-pyrrolidone was prepared as the organic solvent (D-3).

[Examples 1-6, Comparative Examples 1-3]
Various materials were blended at a mass ratio shown in Table 1. Then, it filtered with the filter made from a fluororesin with the hole diameter of 0.2 micrometer, and obtained the photosensitive resin composition.
In addition, about the photosensitive resin composition in each Example and each comparative example, evaluation shown below was performed. The results are as shown in Table 1.

(Viscosity increase rate)
About the photosensitive resin composition as described in each Example and each comparative example, the viscosity before standing (E0) using the E-type viscosity meter (the Toki Sangyo make: TVE-22H) was measured. Thereafter, the photosensitive resin composition was allowed to stand for 1 week in a temperature-controlled room maintained at 23 degrees, and the viscosity (E1) after standing was measured. Using the viscosity E0 before standing and the viscosity E1 after standing, the rate of increase in viscosity at room temperature was derived from the following formula.
Viscosity increase rate (%) = (E1-E0) / E0 * 100
A viscosity increase rate of more than 100% was defined as gelation. The unit in Table 1 is%.

(Patterning)
The photosensitive resin composition prepared in each example and each comparative example was applied on a silicon wafer using a spin coater, and then pre-baked at 120 ° C. for 4 minutes on a hot plate to apply a film having a thickness of about 9.4 μm. A membrane was obtained. Through this coating film, a mask made by Toppan Printing Co., Ltd. (test chart No. 1: a remaining pattern and a blanking pattern with a width of 0.88 to 50 μm are drawn), and an i-line stepper (Nikon Corporation 4425i) ) Was used to change the exposure amount and irradiated with ultraviolet rays.
Next, using a 2.38% tetramethylammonium hydroxide aqueous solution, paddle development was performed by adjusting the development time so that the difference in film thickness between the pre-baked and the unexposed areas after development was 1.5 μm. Thereafter, the substrate was rinsed with pure water for 10 seconds and then dried. Thereafter, the 10 μm via pattern was observed with a microscope. When the pattern was formed, it was evaluated as ◯, and when the pattern was not formed, it was evaluated as x.

(Development adhesion)
About the photosensitive resin composition produced by each Example and each comparative example, the adhesiveness at the time of image development was evaluated as follows. First, an 8-inch silicon wafer (Si substrate) was prepared, and the obtained varnish-like photosensitive resin composition was applied using a spin coater, and then heated at 120 ° C. for 240 seconds to remove the solvent. Went. Through this mask, in which a line and space pattern with a width of 1 to 20 μm and a via hole are drawn on this coating film, an i-line stepper (manufactured by Nikon Corporation, NSR-4425i) is used to change the exposure amount and to change the i-line. Next, using a 2.38% tetramethylammonium hydroxide aqueous solution as a developer, the development time is adjusted to 2 so that the difference in film thickness between the pre-baked and the unexposed areas after development is 1.5 μm. The exposed portion was dissolved and removed by performing paddle development twice. Thereafter, the substrate was rinsed with pure water for 10 seconds and then dried. The pattern thus obtained is confirmed with a microscope, and a 10 μm line-and-space pattern is formed on the wafer at an exposure amount at which a 50 μm via hole pattern is formed. The case where the andspace pattern disappeared due to peeling was evaluated as x, and the adhesion during development was evaluated.

(Crack during rewiring)
About the photosensitive resin composition produced by each Example and each comparative example, the crack at the time of rewiring (at the time of 2 layer application | coating) was evaluated as follows. First, an 8-inch silicon wafer (Si substrate) was prepared, and the obtained varnish-like photosensitive resin composition was applied using a spin coater, and then heated at 120 ° C. for 240 seconds to remove the solvent. Went. Through this mask, a line and space pattern and a via pattern with a width of 1 to 20 μm are drawn, and an i-line stepper (Nikon Co., Ltd., NSR-4425i) is used to change the exposure and to change the i-line. Next, using a 2.38% tetramethylammonium hydroxide aqueous solution as a developer, the development time is adjusted to 2 so that the difference in film thickness between the pre-baked and the unexposed areas after development is 1.5 μm. The exposed portion was dissolved and removed by performing paddle development twice. After performing the above treatment, heat treatment was performed at 230 ° C. for 90 minutes under a condition of an oxygen concentration of 100 ppm or less using a high-temperature clean oven (Koyo Thermo System, CLH-21CDH). On the thus prepared patterned photosensitive resin composition, a second coating film is applied using a spin coater so that the coating thickness becomes 12 μm, and is removed by heating at 120 ° C. for 240 seconds. Solvent was used to obtain a two-layer coated wafer. Observe the two-layer coated wafer obtained using a microscope and mark the case where there is no crack in the first layer pattern as x and the case where there is a crack as x. Cracking evaluation was performed.

  As shown in Table 1, in each Example, the rate of increase in viscosity was low, the patterning and development adhesion were excellent, and the occurrence of cracks in the cured film could be suppressed. Accordingly, in the present invention, by combining the components (A) to (D), a photosensitive resin composition that suppresses an increase in viscosity as a resin composition and has excellent development adhesion is provided. You can see that you can.

  This application claims the priority on the basis of Japanese application Japanese Patent Application No. 2015-147160 for which it applied on July 24, 2015, and takes in those the indications of all here.

Claims (12)

A photosensitive resin composition used to form a permanent film,
(A) Polyamide resin having a structure selected from the group consisting of a polybenzoxazole structure, a polybenzoxazole precursor structure, a polyimide structure, and a polyimide precursor structure (B) photoacid generator (C) adhesion aid (D) organic A photosensitive resin composition comprising a solvent, wherein the (D) organic solvent comprises a compound having an ether bond and an amide bond in the molecule. The photosensitive resin composition according to claim 1, wherein the compound having an ether bond and an amide bond in the molecule is a compound represented by the following general formula (1).

(In formula (1), R ₁ , R ₂ and R ₃ are each an alkyl group having 1 to 10 carbon atoms.)   The photosensitive resin composition of Claim 1 or 2 which contains 25 mass% or more of compounds which have an ether bond and an amide bond in the said molecule | numerator in the said (D) organic solvent.   The photosensitive resin composition according to any one of claims 1 to 3, wherein the (A) polyamide resin has a fluorine content of 8 wt% or less as measured by elemental analysis.   The photosensitive resin composition according to claim 1, wherein the (C) adhesion assistant is a compound having at least one or more carboxyl groups in the molecule.   The photosensitive resin composition according to any one of claims 1 to 5, wherein the (B) photoacid generator is contained in an amount of 5 to 40 parts by mass with respect to 100 parts by mass of the (A) polyamide resin. object.   The photosensitive resin according to any one of claims 1 to 6, wherein the (C) adhesion assistant is contained in an amount of 0.01 to 20 parts by mass with respect to 100 parts by mass of the (A) polyamide resin. Composition.   The photosensitive resin composition as described in any one of Claims 1 thru | or 7 with which the said (D) organic solvent is contained 100 mass parts or more and 1000 mass parts or less with respect to 100 mass parts of said (A) polyamide resins.   The cured film comprised with the hardened | cured material of the photosensitive resin composition as described in any one of Claims 1 thru | or 8.   The protective film comprised with the cured film of Claim 9.   The insulating film comprised with the cured film of Claim 9.   An electronic device comprising the cured film according to claim 9.

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