WO2025095080A1 - Photosensitive resin composition, method for producing cured pattern product, and cured product - Google Patents

Abstract

This photosensitive resin composition comprises (A) a polyimide precursor, (B) a polymerizable monomer including no cyclic skeleton, (C) a photopolymerization initiator, and (D) a compound including an anthracene structure. The content of the polymerizable monomer including a cyclic skeleton is 20% by mass or less with respect to the total amount of the polyimide precursor (A).

Description

Photosensitive resin composition, method for producing patterned cured product, and cured product

This disclosure relates to a photosensitive resin composition, a method for producing a patterned cured product, and the cured product.

Conventionally, polyimide, polybenzoxazole, and the like, which have excellent heat resistance, electrical properties, mechanical properties, etc., have been used for the surface protective films and interlayer insulating films of semiconductor elements. In recent years, photosensitive resin compositions in which these resins themselves have been given photosensitivity have been used. The use of such photosensitive resin compositions can simplify the manufacturing process of the patterned cured product, shortening the complicated manufacturing process (see, for example, Patent Document 1).

In recent years, the miniaturization of transistors, which has supported the high performance of computers, has reached the limits of scaling laws, and stacked device structures in which semiconductor elements are stacked three-dimensionally to achieve even higher performance and speed have been attracting attention.

Among stacked device structures, multi-die fanout wafer level packaging is a package manufactured by sealing multiple dies together in one package, and is attracting a great deal of attention because it is expected to achieve lower costs and higher performance than the previously proposed fan-out wafer level packaging (manufactured by sealing one die in one package).

In the manufacture of multi-die fan-out wafer-level packages, low-temperature curing is highly required from the standpoint of protecting high-performance dies, protecting sealing materials with low heat resistance, and improving yields (see, for example, Patent Document 2).

Furthermore, a resin composition containing a polyimide precursor has been disclosed (see, for example, Patent Document 3).

JP 2009-265520 A WO 2008/111470 JP 2016-199662 A

In photosensitive resin compositions containing polyimide precursors, etc., there is a demand for improved reactivity upon exposure to light; for example, it is desirable to increase the residual film rate of the cured film. Furthermore, when a cured film of the photosensitive resin composition is formed on a substrate such as a silicon wafer, it is required that the occurrence of warping after curing can be suppressed.

The present disclosure aims to provide a photosensitive resin composition that has excellent reactivity and is capable of suppressing warping after curing, a method for producing a patterned cured product using this photosensitive resin composition, and a cured product obtained by curing this photosensitive resin composition.

Specific means for achieving the above object are as follows.
<1> (A) a polyimide precursor;
(B) a polymerizable monomer not containing a cyclic skeleton;
(C) a photopolymerization initiator; and
(D) a compound containing an anthracene structure;
Including,
The content of the polymerizable monomer having a cyclic skeleton is 20 mass % or less based on the total amount of the polyimide precursor (A).
<2> The photosensitive resin composition according to <1>, further comprising (E) a solvent.
<3> The photosensitive resin composition according to <1> or <2>, wherein the polymerizable monomer (B) includes a (meth)acrylic compound including two (meth)acrylic groups.
<4> The photosensitive resin composition according to any one of <1> to <3>, wherein the polymerizable monomer (B) includes a (meth)acrylic compound having three or more (meth)acrylic groups.
<5> The photosensitive resin composition according to any one of <1> to <4>, wherein the polyimide precursor contains a compound having a structural unit represented by the following general formula (1):

In general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, ^R6 and ^R7 each independently represent a hydrogen atom or a monovalent organic group, and at least one of ^R6 and ^R7 has a polymerizable unsaturated bond.
<6> The photosensitive resin composition according to any one of <1> to <5>, wherein the compound (D) includes a compound represented by the following general formula (D):

In general formula (D), R _x 's each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 atoms, or a halogen atom, and n represents an integer of 0 to 10.
<7> The photosensitive resin composition according to any one of <1> to <6>, wherein the compound (D) includes at least one selected from the group consisting of dibutoxyanthracene, dimethoxyanthracene, diethoxyanthracene, and diethoxyethylanthracene.
<8> The photosensitive resin composition according to any one of <1> to <7>, further comprising (F) a thermal polymerization initiator.
<9> The photosensitive resin composition according to any one of <1> to <8>, which is for use in a panel level package.
<10> A step of applying the photosensitive resin composition according to any one of <1> to <9> onto a substrate and drying the composition to form a photosensitive resin film;
a step of exposing the photosensitive resin film to a pattern to obtain a resin film;
developing the resin film after the patterned exposure with an organic solvent to obtain a patterned resin film;
and heat-treating the patterned resin film.
<11> A cured product obtained by curing the photosensitive resin composition according to any one of <1> to <9>.

The present disclosure provides a photosensitive resin composition that has excellent reactivity and can suppress warping after curing, a method for producing a patterned cured product using this photosensitive resin composition, and a cured product obtained by curing this photosensitive resin composition.

1A to 1C are diagrams illustrating a manufacturing process for an electronic component according to an embodiment of the present disclosure.

Hereinafter, embodiments of the present disclosure will be described in detail. However, the present disclosure is not limited to the following embodiments.
In the present disclosure, constituent elements (including element steps, etc.) are not essential unless otherwise specified. The same applies to numerical values and their ranges, and do not limit the present disclosure.
In the present disclosure, the term "step" includes not only a step that is independent of other steps, but also a step that cannot be clearly distinguished from other steps as long as the purpose of the step is achieved.
In the present disclosure, the numerical ranges indicated using "to" include the numerical values before and after "to" as the minimum and maximum values, respectively.
In the numerical ranges described in the present disclosure in stages, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. In addition, in the numerical ranges described in the present disclosure, the upper or lower limit value of the numerical range may be replaced with a value shown in the examples.
In the present disclosure, each component may contain multiple types of corresponding substances. When multiple types of substances corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple substances present in the composition, unless otherwise specified.
In the present disclosure, the terms "layer" and "film" include cases where the layer or film is formed over the entire area when the area in which the layer or film is present is observed, as well as cases where the layer or film is formed over only a portion of the area.
In the present disclosure, the thickness of a layer or film is determined as the arithmetic mean value of thicknesses measured at five points on the layer or film of interest.
The thickness of the layer or film can be measured using a micrometer or the like. In the present disclosure, when the thickness of the layer or film can be measured directly, it is measured using a micrometer. On the other hand, when the thickness of one layer or the total thickness of multiple layers is measured, it may be measured by observing the cross section of the measurement target using an electron microscope.

In the present disclosure, the term "(meth)acrylic group" means "acrylic group" and "methacrylic group", the term "(meth)acrylate" means "acrylate" and "methacrylate", and the term "(meth)acryloyl" means "acryloyl" and "methacryloyl".
In the present disclosure, when a functional group has a substituent, the number of carbon atoms in the functional group means the total number of carbon atoms including the number of carbon atoms in the substituent.
When an embodiment of the present disclosure is described with reference to the drawings, the configuration of the embodiment is not limited to the configuration shown in the drawings. In addition, the size of the members in each drawing is conceptual, and the relative relationship between the sizes of the members is not limited to this.

<Photosensitive resin composition>
The photosensitive resin composition of the present disclosure includes (A) a polyimide precursor, (B) a polymerizable monomer not containing a cyclic skeleton, (C) a photopolymerization initiator, and (D) a compound containing an anthracene structure, and the content of the polymerizable monomer containing a cyclic skeleton is 20 mass% or less based on the total amount of the (A) polyimide precursor.

The photosensitive resin composition disclosed herein has excellent reactivity and is capable of suppressing warping after curing. The reason for this is believed to be as follows. Note that the disclosure is not limited to the following belief.

The photosensitive resin composition contains (A) a polyimide precursor and (D) a compound containing an anthracene structure, and therefore has excellent reactivity upon exposure to light. For example, it has excellent photosensitivity characteristics when exposed to h-rays, and tends to produce a cured product with a high residual film rate.

Furthermore, the photosensitive resin composition contains (B) a polymerizable monomer not containing a cyclic skeleton, and the content of the polymerizable monomer containing a cyclic skeleton is 20 mass % or less, preferably 10 mass % or less, and more preferably 5 mass % or less, based on the total amount of (A) the polyimide precursor, thereby making it possible to suppress warping after curing.
The lower limit of the content of the polymerizable monomer having a cyclic skeleton is not particularly limited, and may be 0 mass %.

In addition, by using a polymerizable monomer containing a cyclic skeleton and a compound containing an anthracene structure (D), peeling (undercut) is likely to occur at the bottom of the side of the opening of the cured product when the cured product is produced. In the present disclosure, by reducing the content of the polymerizable monomer containing a cyclic skeleton, it is possible to suppress the above-mentioned undercut.

The photosensitive resin composition of the present disclosure is preferably a negative photosensitive resin composition.
In addition, from the viewpoint of photosensitive properties during h-ray exposure, the photosensitive resin composition of the present disclosure is preferably used for a panel level package (for example, a package having no package substrate, and instead a structure in which wiring is drawn from a chip terminal and connected to an external terminal via a rewiring layer). The photosensitive resin composition of the present disclosure is preferably a material for a panel level package or a material for electronic components.

The following provides a detailed explanation of each component contained in the photosensitive resin composition disclosed herein.

((A) Polyimide Precursor)
The photosensitive resin composition of the present disclosure contains (A) a polyimide precursor (hereinafter also referred to as “component (A)”).

The component (A) is preferably at least one resin selected from the group consisting of polyamic acid, polyamic acid ester, polyamic acid salt, and polyamic acid amide. The polyamic acid ester and polyamic acid amide are compounds in which hydrogen atoms of at least some of the carboxyl groups in a polyamic acid are substituted with monovalent organic groups, and the polyamic acid salt is a compound in which at least some of the carboxyl groups in a polyamic acid form a salt structure with a basic compound having a pH of over 7.
The component (A) may have a polymerizable unsaturated bond.

The (A) component preferably contains a compound having a structural unit represented by the following general formula (1). This tends to result in electronic components having a cured product that exhibits high reliability.

In general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, ^R6 and ^R7 each independently represent a hydrogen atom or a monovalent organic group, and at least one of ^R6 and ^R7 has a polymerizable unsaturated bond.
The polyimide precursor may have a plurality of structural units represented by the above general formula (1), and X, Y, ^R6 and ^R7 in the plurality of structural units may be the same or different.
In addition, as long as R ⁶ and R ⁷ are each independently a hydrogen atom or a monovalent organic group, the combination is not particularly limited. For example, at least one of R ⁶ and R ⁷ may be a hydrogen atom and the remaining may be a monovalent organic group described below, or they may be the same or different monovalent organic groups. As described above, when the polyimide precursor has a plurality of structural units represented by the above general formula (1), the combinations of R ⁶ and R ⁷ of each structural unit may be the same or different.

In formula (1), the tetravalent organic group represented by X preferably has 4 to 25 carbon atoms, more preferably 5 to 13 carbon atoms, and even more preferably 6 to 12 carbon atoms.
The tetravalent organic group represented by X may contain an aromatic ring. Examples of the aromatic ring include aromatic hydrocarbon groups (e.g., aromatic rings having 6 to 20 carbon atoms) and aromatic heterocyclic groups (e.g., heterocyclic rings having 5 to 20 atoms). The tetravalent organic group represented by X is preferably an aromatic hydrocarbon group. Examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, and a phenanthrene ring.
When the tetravalent organic group represented by X contains an aromatic ring, each aromatic ring may have a substituent or may be unsubstituted. Examples of the substituent of the aromatic ring include an alkyl group, a fluorine atom, a halogenated alkyl group, a hydroxyl group, and an amino group.
When the tetravalent organic group represented by X contains a benzene ring, the tetravalent organic group represented by X preferably contains one to four benzene rings, more preferably contains one to three benzene rings, and even more preferably contains one or two benzene rings.
When the tetravalent organic group represented by X contains two or more benzene rings, the benzene rings may be linked by a single bond, or may be linked by a linking group such as an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R ^A ) ₂ -; each of the two R ^A 's independently represents a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si(R ^B ) ₂ -O-) _n ; each of the two R ^B 's independently represents a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or 2 or more), or a composite linking group formed by combining at least two of these linking groups. In addition, the two benzene rings may be linked at two points by at least one of a single bond and a linking group to form a five- or six-membered ring containing a linking group between the two benzene rings.

In formula (1), the --COOR ⁶ group and the --CONH-- group are preferably located at the ortho position relative to each other, and the --COOR ⁷ group and the --CO-- group are preferably located at the ortho position relative to each other.

Specific examples of the tetravalent organic group represented by X include groups represented by the following formulae (A) to (F). Among them, from the viewpoint of obtaining a cured product having excellent flexibility, a group represented by the following formula (E) is preferred, and in the following formula (E), C is more preferably a group containing an ether bond, and further preferably an ether bond. The following formula (F) is a structure in which C in the following formula (E) is a single bond.
It should be noted that the present disclosure is not limited to the following specific examples.

In formula (D), A and B are each independently a single bond or a divalent group not conjugated with a benzene ring. However, A and B cannot both be single bonds. Examples of the divalent group not conjugated with a benzene ring include a methylene group, a halogenated methylene group, a halogenated methylmethylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R ^A ) ₂ -; each of the two R ^A 's independently represents a hydrogen atom, an alkyl group, or a phenyl group). Among these, A and B are each independently preferably a methylene group, a bis(trifluoromethyl)methylene group, a difluoromethylene group, an ether bond, a sulfide bond, or the like, and more preferably an ether bond.

In formula (E), C represents a single bond, an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a phenylene group, an ester bond (-O-C(=O)-), a silylene bond (-Si(R ^A ) ₂ -; two R ^A 's each independently represent a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si(R ^B ) ₂ -O-) _n ; two R ^B 's each independently represent a hydrogen atom, an alkyl group, or a phenyl group, and n is an integer of 1 or 2 or more), or a divalent group comprising at least two of these. C preferably contains an ether bond, and is preferably an ether bond.
In addition, C may include a structure represented by the following formula (C1).

The alkylene group represented by C in formula (E) is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably an alkylene group having 1 or 2 carbon atoms.
Specific examples of the alkylene group represented by C in formula (E) include linear alkylene groups such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group; a methylmethylene group, a methylethylene group, an ethylmethylene group, a dimethylmethylene group, a 1,1-dimethylethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, an ethylethylene group, a 1-methyltetramethylene group, a 2-methyltetramethylene group, a 1-ethyltrimethylene group, a 2-ethyltrimethylene group, a 1,1-dimethyl branched alkylene groups such as ethyltrimethylene group, 1,2-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethyltetramethylene group, 2-ethyltetramethylene group, 1,1-dimethyltetramethylene group, 1,2-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, and 1,4-dimethyltetramethylene group. Among these, a methylene group is preferred.

The halogenated alkylene group represented by C in formula (E) is preferably a halogenated alkylene group having 1 to 10 carbon atoms, more preferably a halogenated alkylene group having 1 to 5 carbon atoms, and even more preferably a halogenated alkylene group having 1 to 3 carbon atoms.
Specific examples of the halogenated alkylene group represented by C in formula (E) include alkylene groups in which at least one hydrogen atom contained in the alkylene group represented by C in formula (E) is substituted with a halogen atom such as a fluorine atom or a chlorine atom. Among these, a fluoromethylene group, a difluoromethylene group, a hexafluorodimethylmethylene group, etc. are preferred.

The alkyl group represented by R ^A or R ^B contained in the silylene bond or siloxane bond is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably an alkyl group having 1 or 2 carbon atoms. Specific examples of the alkyl group represented by R ^A or R ^B include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, and the like.

In formula (1), the divalent organic group represented by Y preferably has 4 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 12 to 18 carbon atoms.
The skeleton of the divalent organic group represented by Y may be the same as the skeleton of the tetravalent organic group represented by X, and a preferred skeleton of the divalent organic group represented by Y may be the same as the preferred skeleton of the tetravalent organic group represented by X. The skeleton of the divalent organic group represented by Y may be a structure in which two bonding positions of the tetravalent organic group represented by X are substituted with atoms (e.g., hydrogen atoms) or functional groups (e.g., alkyl groups).
The divalent organic group represented by Y may be a divalent aliphatic group or a divalent aromatic group. From the viewpoint of heat resistance, the divalent organic group represented by Y is preferably a divalent aromatic group. Examples of the divalent aromatic group include a divalent aromatic hydrocarbon group (e.g., an aromatic ring having 6 to 20 carbon atoms) and a divalent aromatic heterocyclic group (e.g., a heterocyclic ring having 5 to 20 atoms), and the like, with a divalent aromatic hydrocarbon group being preferred.

Specific examples of the divalent aromatic group represented by Y include groups represented by the following formulae (G) and (H). Among these, from the viewpoint of obtaining a cured product with excellent flexibility, the group represented by the following formula (H) is preferred, and among these, in the following formula (H), D is more preferably a group containing a single bond or an ether bond, even more preferably a group containing a single bond or an ether bond, particularly preferably a group containing an ether bond, and extremely preferably an ether bond.

In formulae (G) to (H), R each independently represents an alkyl group, an alkoxy group, a halogenated alkyl group, a phenyl group, or a halogen atom, and n each independently represents an integer of 0 to 4.
In formula (H), D represents a single bond, an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a phenylene group, an ester bond (-O-C(=O)-), a silylene bond (-Si( ^RA ) _2- ; two ^RA 's each independently represent a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si( ^RB ) ₂ -O-) _n ; two ^RB 's each independently represent a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or 2 or more), or a divalent group combining at least two of these. D may also be a structure represented by formula (C1) above. Specific examples of D in formula (H) are the same as the specific examples of C in formula (E).
It is preferable that each D in formula (H) independently represents a single bond, an ether bond, a group containing an ether bond and a phenylene group, a group containing an ether bond, a phenylene group and an alkylene group, or the like.

The alkyl group represented by R in formulas (G) to (H) is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and even more preferably an alkyl group having 1 or 2 carbon atoms.
Specific examples of the alkyl group represented by R in formulae (G) to (H) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

The alkoxy group represented by R in formulas (G) to (H) is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 5 carbon atoms, and even more preferably an alkoxy group having 1 or 2 carbon atoms.
Specific examples of the alkoxy group represented by R in formulae (G) to (H) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, and a t-butoxy group.

The halogenated alkyl group represented by R in Formulae (G) to (H) is preferably a halogenated alkyl group having 1 to 5 carbon atoms, more preferably a halogenated alkyl group having 1 to 3 carbon atoms, and even more preferably a halogenated alkyl group having 1 or 2 carbon atoms.
Specific examples of the halogenated alkyl group represented by R in formulas (G) to (H) include alkyl groups in which at least one hydrogen atom contained in the alkyl group represented by R in formulas (G) to (H) is substituted with a halogen atom such as a fluorine atom or a chlorine atom. Among these, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, etc. are preferred.

In formulas (G) to (H), n is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.

Specific examples of the divalent aliphatic group represented by Y include linear or branched alkylene groups, cycloalkylene groups, and divalent groups having a polyalkylene oxide structure.

The linear or branched alkylene group represented by Y is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 1 to 15 carbon atoms, and even more preferably an alkylene group having 1 to 10 carbon atoms.
Specific examples of the alkylene group represented by Y include a tetramethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a nonamethylene group, a decamethylene group, an undecamethylene group, a dodecamethylene group, a 2-methylpentamethylene group, a 2-methylhexamethylene group, a 2-methylheptamethylene group, a 2-methyloctamethylene group, a 2-methylnonamethylene group, and a 2-methyldecamethylene group.

The cycloalkylene group represented by Y is preferably a cycloalkylene group having 3 to 10 carbon atoms, and more preferably a cycloalkylene group having 3 to 6 carbon atoms.
Specific examples of the cycloalkylene group represented by Y include a cyclopropylene group, a cyclohexylene group, and the like.

The unit structure contained in the divalent group having a polyalkylene oxide structure represented by Y is preferably an alkylene oxide structure having 1 to 10 carbon atoms, more preferably an alkylene oxide structure having 1 to 8 carbon atoms, and even more preferably an alkylene oxide structure having 1 to 4 carbon atoms. Of these, the polyalkylene oxide structure is preferably a polyethylene oxide structure or a polypropylene oxide structure. The alkylene group in the alkylene oxide structure may be linear or branched. The unit structure in the polyalkylene oxide structure may be of one type or two or more types.

The divalent organic group represented by Y may be a divalent group having a polysiloxane structure. Examples of the divalent group having a polysiloxane structure represented by Y include divalent groups having a polysiloxane structure in which a silicon atom in the polysiloxane structure is bonded to a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
Specific examples of the alkyl group having 1 to 20 carbon atoms bonded to a silicon atom in the polysiloxane structure include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-octyl group, a 2-ethylhexyl group, an n-dodecyl group, etc. Among these, a methyl group is preferable.
The aryl group having 6 to 18 carbon atoms bonded to the silicon atom in the polysiloxane structure may be unsubstituted or substituted with a substituent. Specific examples of the substituent when the aryl group has a substituent include a halogen atom, an alkoxy group, and a hydroxy group. Specific examples of the aryl group having 6 to 18 carbon atoms include a phenyl group, a naphthyl group, and a benzyl group. Of these, a phenyl group is preferred.
The alkyl group having 1 to 20 carbon atoms or the aryl group having 6 to 18 carbon atoms in the polysiloxane structure may be of one type or of two or more types.
The silicon atom constituting the divalent group having a polysiloxane structure represented by Y may be bonded to the NH group in general formula (1) via an alkylene group such as a methylene group or an ethylene group, or an arylene group such as a phenylene group.

The group represented by formula (G) is preferably a group represented by the following formula (G'), and the group represented by formula (H) is preferably a group represented by the following formula (H'), formula (H'') or formula (H'''), and from the viewpoint of having a flexible skeleton, a group represented by the following formula (H') or formula (H'') is more preferable.

In formula (H'"), each R independently represents an alkyl group, an alkoxy group, a halogenated alkyl group, a phenyl group, or a halogen atom. R is preferably an alkyl group, and more preferably a methyl group.

In the general formula (1), the combination of the tetravalent organic group represented by X and the divalent organic group represented by Y is not particularly limited. Examples of the combination of the tetravalent organic group represented by X and the divalent organic group represented by Y include a combination in which X is a group represented by formula (E) and Y is a group represented by formula (H).

R ⁶ and R ⁷ each independently represent a hydrogen atom or a monovalent organic group, with the proviso that at least one of them has a polymerizable unsaturated bond. The monovalent organic group is preferably an aliphatic hydrocarbon group having 1 to 4 carbon atoms or an organic group having an unsaturated double bond, more preferably any one of a group represented by the following general formula (2), an ethyl group, an isobutyl group, or a t-butyl group, and further preferably contains an aliphatic hydrocarbon group having 1 or 2 carbon atoms or a group represented by the following general formula (2). In this case, at least one of R ⁶ and R ⁷ is a group represented by general formula (2).
When the monovalent organic group contains an organic group having an unsaturated double bond, preferably a group represented by the following general formula (2), at least a part of the unsaturated double bond moiety is eliminated by the action of a base or the like.

Specific examples of aliphatic hydrocarbon groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, and t-butyl groups, with ethyl, isobutyl, and t-butyl groups being preferred.

In formula (2), R ⁸ to R ¹⁰ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and R ^x represents a divalent linking group.

The carbon number of the aliphatic hydrocarbon group represented by R ⁸ to R ¹⁰ in general formula (2) is 1 to 3, and preferably 1 or 2. Specific examples of the aliphatic hydrocarbon group represented by R ⁸ to R ¹⁰ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, etc., and a methyl group is preferred.

As a combination of R ⁸ to R ¹⁰ in the general formula (2), a combination in which R ⁸ and R ⁹ are hydrogen atoms and R ¹⁰ is a hydrogen atom or a methyl group is preferred.

In general formula (2), R ^x is a divalent linking group, and is preferably a hydrocarbon group having 1 to 10 carbon atoms. Examples of the hydrocarbon group having 1 to 10 carbon atoms include linear or branched alkylene groups.
The number of carbon atoms in R ^x is preferably 1 to 10, more preferably 2 to 5, and further preferably 2 or 3.

In general formula (1), it is preferable that at least one of ^R6 and ^R7 is a group represented by general formula (2), and it is more preferable that both of ^R6 and ^R7 are groups represented by general formula (2).

When the polyimide precursor (A) contains a compound having a structural unit represented by the above-mentioned general formula (1), the ratio of ^R6 and ^R7 , which are groups represented by the general formula (2), to the sum of ^R6 and ^R7 of all structural units contained in the compound is preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more. The upper limit is not particularly limited, and may be 100 mol%.
The above ratio may be 0 mol % or more and less than 60 mol %.

The group represented by general formula (2) is preferably a group represented by the following general formula (2'):

In formula (2′), R ⁸ to R ¹⁰ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms; q represents an integer of 1 to 10.

In general formula (2'), q is an integer from 1 to 10, preferably an integer from 2 to 5, and more preferably 2 or 3.

The content of the structural unit represented by general formula (1) contained in the compound having the structural unit represented by general formula (1) is preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more, based on the total structural units. The upper limit of the aforementioned content is not particularly limited, and may be 100 mol%.

The polyimide precursor (A) may be synthesized using a tetracarboxylic dianhydride and a diamine compound. In this case, in the general formula (1), X corresponds to a residue derived from the tetracarboxylic dianhydride, and Y corresponds to a residue derived from the diamine compound. The polyimide precursor (A) may be synthesized using a tetracarboxylic acid instead of the tetracarboxylic dianhydride.

Specific examples of tetracarboxylic dianhydrides include pyromellitic dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 2,3,5,6-pyridine tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, carboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, m-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, p-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, 1,1,4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 1,3,3,3-hexafluoro-2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1,1,3,3,3-hexafluoro-2,2-bis(3,4-di 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis{4'-(2,3-dicarboxyphenoxy)phenyl}propane dianhydride, 2,2-bis{4'-(3,4-dicarboxyphenoxy)phenyl}propane dianhydride, 1,1,1,3,3,3-hexafluoro-2,2-bis{4'-(2,3-dicarboxyphenoxy)phenyl}propane dianhydride Examples of suitable dianhydrides include 1,1,1,3,3,3-hexafluoro-2,2-bis{4'-(3,4-dicarboxyphenoxy)phenyl}propane dianhydride, 4,4'-oxydiphthalic dianhydride, 4,4'-sulfonyldiphthalic dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, cyclopentanone bisspironorbornane tetracarboxylic dianhydride, 2,2-bis{4-(4'-phenoxy)phenyl}propane tetracarboxylic dianhydride, etc. Among these, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride and 3,3',4,4'-biphenyl tetracarboxylic dianhydride are preferred.
The tetracarboxylic dianhydrides may be used alone or in combination of two or more kinds.

Specific examples of the diamine compound include 2,2'-dimethylbiphenyl-4,4'-diamine, 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 2,2'-difluoro-4,4'-diaminobiphenyl, p-phenylenediamine, m-phenylenediamine, p-xylylenediamine, m-xylylenediamine, 1,5-diaminonaphthalene, benzidine, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 2,4'-diaminodiphenyl ether, 2,2'-diaminodiphenyl ether, 4, 4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 2,4'-diaminodiphenyl sulfone, 2,2'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 2,4'-diaminodiphenyl sulfide, 2,2'-diaminodiphenyl sulfide, o-tolidine, o-tolidine sulfone, 4,4'-methylenebis(2,6-diethylaniline), 4,4'-methylenebis(2,6-diisopropylaniline), 2 ,4-diaminomesitylene, 1,5-diaminonaphthalene, 4,4'-benzophenonediamine, bis-{4-(4'-aminophenoxy)phenyl}sulfone, 2,2-bis{4-(4'-aminophenoxy)phenyl}propane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3',5,5'-tetramethyl-4,4'-diaminodiphenylmethane, bis{4-(3'-aminophenoxy)phenyl}sulfone, 2,2-bis(4-aminophenyl)propane, 9,9-bis(4-aminophenyl)fluorene, 1,3-bis(3-aminophenoxy)benzene, 1, Examples of the diamine compound include 4-diaminobutane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 2-methyl-1,5-diaminopentane, 2-methyl-1,6-diaminohexane, 2-methyl-1,7-diaminoheptane, 2-methyl-1,8-diaminooctane, 2-methyl-1,9-diaminononane, 2-methyl-1,10-diaminodecane, 1,4-cyclohexanediamine, 1,3-cyclohexanediamine, and diaminopolysiloxane. As the diamine compound, 2,2'-dimethylbiphenyl-4,4'-diamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, and 1,3-bis(3-aminophenoxy)benzene are preferred. Among these, 4,4'-diaminodiphenyl ether, 1,3-bis(3-aminophenoxy)benzene, and 2,2-bis{4-(4'-aminophenoxy)phenyl}propane are more preferred from the viewpoint of having a flexible skeleton and excellent adhesiveness.
The diamine compounds may be used alone or in combination of two or more kinds.

A compound having a structural unit represented by general formula (1) in which at least one of ^R6 and ^R7 in general formula (1) is a monovalent organic group can be obtained, for example, by the following method (a) or (b).
(a) A tetracarboxylic dianhydride (preferably a tetracarboxylic dianhydride represented by the following general formula (8)) is reacted with a compound represented by R-OH in an organic solvent to form a diester derivative, and then the diester derivative is subjected to a condensation reaction with a diamine compound represented by H ₂ N-Y-NH ₂ .
(b) A tetracarboxylic dianhydride is reacted with a diamine compound represented by H ₂ N-Y-NH ₂ in an organic solvent to obtain a polyamic acid solution, and a compound represented by R-OH is added to the polyamic acid solution and reacted in an organic solvent to introduce an ester group.
Here, Y in the diamine compound represented by H ₂ N-Y-NH ₂ is the same as Y in general formula (1), and specific examples and preferred examples are also the same. Furthermore, R in the compound represented by R-OH represents a monovalent organic group, and specific examples and preferred examples are the same as R ⁶ and R ⁷ in general formula (1).
The tetracarboxylic dianhydride represented by the general formula (8), the diamine compound represented by H ₂ N-Y-NH ₂ , and the compound represented by R-OH may each be used alone or in combination of two or more.
Examples of the organic solvent include N-methyl-2-pyrrolidone, γ-butyrolactone, dimethoxyimidazolidinone, and 3-methoxy-N,N-dimethylpropanamide, and among these, 3-methoxy-N,N-dimethylpropanamide is preferred.
A polyimide precursor may be synthesized by reacting a dehydration condensation agent with a polyamic acid solution together with the compound represented by R-OH. The dehydration condensation agent preferably contains at least one selected from the group consisting of trifluoroacetic anhydride, N,N'-dicyclohexylcarbodiimide (DCC), and 1,3-diisopropylcarbodiimide (DIC).

The above-mentioned compound contained in the polyimide precursor (A) can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH to form a diester derivative, then reacting the diester with a chlorinating agent such as thionyl chloride to convert it into an acid chloride, and then reacting a diamine compound represented by H ₂ N-Y-NH ₂ with the acid chloride.
The above-mentioned compound contained in the polyimide precursor (A) can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH to form a diester derivative, and then reacting the diamine compound represented by H ₂ N-Y-NH ₂ with the diester derivative in the presence of a carbodiimide compound.
The above-mentioned compound contained in the polyimide precursor (A) can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a diamine compound represented by H ₂ N-Y-NH ₂ to form a polyamic acid, then isoimidizing the polyamic acid in the presence of a dehydrating condensing agent such as trifluoroacetic anhydride, and then reacting the polyamic acid with a compound represented by R-OH. Alternatively, a compound represented by R-OH may be reacted in advance with a part of the tetracarboxylic dianhydride to react the partially esterified tetracarboxylic dianhydride with the diamine compound represented by H ₂ N-Y-NH ₂ .

In general formula (8), X is the same as X in general formula (1), and specific examples and preferred examples are also the same.

The compound represented by R-OH used in the synthesis of the above-mentioned compound contained in the polyimide precursor (A) may be a compound in which a hydroxy group is bonded to R ^x of the group represented by the general formula (2), a compound in which a hydroxy group is bonded to the terminal methylene group of the group represented by the general formula (2'), etc. Specific examples of the compound represented by R-OH include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, etc., among which 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate are preferred.

There are no particular limitations on the molecular weight of the polyimide precursor (A). For example, the weight average molecular weight is preferably 10,000 to 200,000, and more preferably 10,000 to 100,000.
The weight average molecular weight can be measured, for example, by gel permeation chromatography, and can be calculated using a standard polystyrene calibration curve.

The photosensitive resin composition of the present disclosure may contain other resins in addition to the polyimide precursor (A). From the viewpoint of heat resistance, examples of the other resins include polyimide resins, novolac resins, acrylic resins, polyether nitrile resins, polyether sulfone resins, epoxy resins, polyethylene terephthalate resins, polyethylene naphthalate resins, polyvinyl chloride resins, etc. The other resins may be used alone or in combination of two or more.

In the photosensitive resin composition of the present disclosure, the content of the polyimide precursor (A) relative to the total amount of the polymer components is preferably 50% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass.

((B) Polymerizable Monomer Not Containing a Cyclic Skeleton)
The photosensitive resin composition of the present disclosure contains (B) a polymerizable monomer not containing a cyclic skeleton (hereinafter also referred to as "component (B)"). The component (B) preferably contains at least one group containing a polymerizable unsaturated double bond, and more preferably contains at least one (meth)acrylic group from the viewpoint of favorable polymerization when used in combination with the photopolymerization initiator (C). From the viewpoint of improving the crosslink density and improving the photosensitivity, the component (B) preferably contains 2 to 6 groups containing a polymerizable unsaturated double bond, and more preferably contains 2 to 4 groups containing a polymerizable unsaturated double bond.
The polymerizable monomers may be used alone or in combination of two or more.

(B) The polymerizable monomer may contain a (meth)acrylic compound containing two (meth)acrylic groups (bifunctional (meth)acrylic compound), may contain a (meth)acrylic compound containing three or more (meth)acrylic groups (polyfunctional (meth)acrylic compound), or may contain the aforementioned bifunctional (meth)acrylic compound and polyfunctional (meth)acrylic compound.

The polymerizable monomer containing a (meth)acrylic group is not particularly limited, and examples thereof include
(meth)acrylic compounds containing one (meth)acrylic group, such as 2-hydroxyethyl (meth)acrylate;
Diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, 1,3-bis((meth)acryloyloxy)-2 - (meth)acrylic compounds containing two (meth)acrylic groups, such as hydroxypropane; and (meth)acrylic compounds containing three or more (meth)acrylic groups, such as trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, ethoxylated pentaerythritol tetraacrylate;
Examples include:

Component (B) may be tetraethylene glycol dimethacrylate, ethoxylated pentaerythritol tetraacrylate, or a mixture thereof.

Component (B) may be a polymerizable monomer containing a (meth)acrylic group, or may be a polymerizable monomer other than a polymerizable monomer containing a (meth)acrylic group, or may be a combination of these.

Polymerizable monomers other than those containing a (meth)acrylic group are not particularly limited, and examples include styrene, divinylbenzene, 4-vinyltoluene, 4-vinylpyridine, N-vinylpyrrolidone, methylenebisacrylamide, N,N-dimethylacrylamide, and N-methylolacrylamide.

Component (B) is not limited to compounds having a group containing a polymerizable unsaturated double bond, but may also be a compound having a polymerizable group other than an unsaturated double bond group (e.g., an oxirane ring).

When the photosensitive resin composition of the present disclosure contains component (B), the content of component (B) is not particularly limited, and is preferably 1 part by mass to 100 parts by mass, more preferably 5 parts by mass to 75 parts by mass, even more preferably 10 parts by mass to 50 parts by mass, and particularly preferably 25 parts by mass to 45 parts by mass, relative to 100 parts by mass of component (A).

When component (B) is a mixture of tetraethylene glycol dimethacrylate (B1) and ethoxylated pentaerythritol tetraacrylate (B2), the mass ratio of B2 to B1 (B2/B1) may be 30/100 to 100/100, or 40/100 to 70/100.

((C) Photopolymerization initiator)
The photosensitive resin composition of the present disclosure may contain a photopolymerization initiator (C) (hereinafter also referred to as “component (C)”).
The component (C) is not particularly limited and may be, for example,
1-phenyl-1,2-butanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-benzoyl)oxime, 1,3-diphenylpropanetrione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-3-ethoxyp Oxime compounds such as propanetrione-2-(O-benzoyl)oxime, 1-[4-(phenylthio)phenyl]octane-1,2-dione=2-(O-benzoyloxime), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime), 1-[4-(4-hydroxyethyloxy-phenylthio)phenyl]-1,2-propanedione-2-(O-acetyloxime);
Acetophenone derivatives such as acetophenone, 2,2-diethoxyacetophenone, 3'-methylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methylpropiophenone, 4'-(methylthio)-α-morpholino-α-methylpropiophenone, and 1-hydroxycyclohexyl phenyl ketone;
Thioxanthone, thioxanthone derivatives such as 2-methylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, and diethylthioxanthone;
benzil, benzil dimethyl ketal, benzil-β-methoxyethyl acetal and other benzil derivatives;
Benzoin derivatives such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin phenyl ether, methyl benzoin, ethyl benzoin, and propyl benzoin;
N-arylglycines such as N-phenylglycine;
Peroxides such as benzoyl peroxide;
Aromatic biimidazoles such as 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, and 2-(o- or p-methoxyphenyl)-4,5-diphenylimidazole dimer;
Examples of the phosphine oxide derivatives include acylphosphine oxide derivatives such as 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Irgacure OXE03 (manufactured by BASF), and Irgacure OXE04 (manufactured by BASF).
From the viewpoint of achieving excellent exposure sensitivity, the component (C) preferably contains an oxime compound.
The component (C) may be used alone or in combination of two or more types.

The content of the oxime compound relative to the total amount of component (C) is preferably 60% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more.

The content of component (C) is preferably 0.1 parts by mass to 20 parts by mass, more preferably 1 part by mass to 20 parts by mass, even more preferably 2 parts by mass to 10 parts by mass, and particularly preferably 3 parts by mass to 6 parts by mass, relative to 100 parts by mass of component (A).

((D) Compound containing an anthracene structure)
The photosensitive resin composition of the present disclosure preferably further contains (D) a compound containing an anthracene structure (hereinafter also referred to as “component (D)”).

From the viewpoint of achieving both sensitivity and resolution, it is preferable that component (D) contains a compound represented by general formula (D).

In general formula (D), R _x 's each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 atoms, or a halogen atom, and n represents an integer of 0 to 10.

The alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 2 to 5 carbon atoms.
Specific examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a t-butyl group, and an n-butyl group.

The alkoxy group having 1 to 10 carbon atoms is preferably an alkoxy group having 1 to 6 carbon atoms, and more preferably an alkoxy group having 2 to 5 carbon atoms.
Specific examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, and a butoxy group (eg, an n-butoxy group).

The aryl group having 6 to 18 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms.
Specific examples of the aryl group having 6 to 18 carbon atoms include a phenyl group and a naphthyl group.

The heteroaryl group having 5 to 18 atoms is preferably a heteroaryl group having 5 to 12 atoms, and more preferably a heteroaryl group having 5 to 10 atoms.
Specific examples of the heteroaryl group having 5 to 18 atoms include a pyridyl group, a quinolinyl group, and a carbazolyl group.

From the viewpoint of achieving both solubility in the photosensitive resin composition and photosensitive properties, the component (D) preferably contains a dialkoxyanthracene (e.g., 9,10 dialkoxyanthracene) which may have a substituent, and more preferably contains at least one selected from the group consisting of dibutoxyanthracene (e.g., 9,10 dibutoxyanthracene), dimethoxyanthracene (e.g., 9,10 dimethoxyanthracene), diethoxyanthracene (e.g., 9,10 diethoxyanthracene), and diethoxyethylanthracene (e.g., 9,10 diethoxy-2 ethylanthracene).
Substituents include methyl, ethyl, t-butyl and n-butyl groups.
The component (D) may be used alone or in combination of two or more types.

From the viewpoint of improving solubility in the photosensitive resin composition and photosensitive properties, the content of component (D) is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, even more preferably 0.3 to 5 parts by mass, and particularly preferably 0.4 to 2 parts by mass, per 100 parts by mass of component (A).

(E) Solvent)
The photosensitive resin composition of the present disclosure preferably further contains a solvent (E) (hereinafter also referred to as “component (E)”).

The component (E) is not particularly limited, and examples thereof include ester-based solvents, ketone-based solvents, carbonate-based solvents, heterocyclic compound-based solvents, and amide-based solvents.
The ester-based solvents, ketone-based solvents, carbonate-based solvents, and amide-based solvents may each independently have a cyclic structure or may not have a cyclic structure.
The component (E) may be used alone or in combination of two or more types.

The component (E) may contain, for example, at least one compound selected from the group consisting of compounds represented by the following formulas (3) to (10).
The component (E) may be used alone or in combination of two or more types.

In formulas (3) to (10), R ¹ , R ² , R ⁸ , R ¹⁰ , R ¹¹ , R ¹³ , and R ¹⁴ are each independently an alkyl group having 1 to 4 carbon atoms, and R ³ to R ⁷ , R ⁹ , and R ¹² are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. s is an integer of 0 to 8, t is an integer of 0 to 4, r is an integer of 0 to 4, u is an integer of 0 to 3, v is an integer of 0 to 3, w is an integer of 0 to 4, and x is an integer of 0 to 5.

In formula (3), s is preferably 0.
In formula (4), the alkyl group having 1 to 4 carbon atoms represented by ^R2 is preferably a methyl group or an ethyl group. t is preferably 0, 1 or 2, and more preferably 1.
In formula (5), the alkyl group having 1 to 4 carbon atoms for ^R3 is preferably a methyl group, an ethyl group, a propyl group, or a butyl group. The alkyl group having 1 to 4 carbon atoms for ^R4 and ^R5 is preferably a methyl group or an ethyl group.
In formula (6), the alkyl group having 1 to 4 carbon atoms for R ⁶ to R ⁸ is preferably a methyl group or an ethyl group. r is preferably 0 or 1, and more preferably 0.
In formula (7), the alkyl group having 1 to 4 carbon atoms for R ⁹ and R ¹⁰ is preferably a methyl group or an ethyl group. u is preferably 0 or 1, and more preferably 0.
In formula (8), the alkyl group having 1 to 4 carbon atoms represented by R ¹¹ is preferably a methyl group or an ethyl group. u is preferably 0 or 1, and more preferably 0.
In formula (9), the alkyl group having 1 to 4 carbon atoms for R ¹² is preferably a methyl group or an ethyl group. The alkyl group having 1 to 4 carbon atoms for R ¹³ is preferably a methyl group or an ethyl group. w is preferably 0 or 1, and more preferably 0.
In formula (10), the alkyl group having 1 to 4 carbon atoms represented by R ¹⁴ is preferably a methyl group or an ethyl group. x is preferably 0 or 1, and more preferably 0.

Specific examples of component (E) include the following compounds:

 

In the photosensitive resin composition of the present disclosure, from the viewpoint of reducing toxicity such as reproductive toxicity, the content of N-methyl-2-pyrrolidone (NMP) may be 1 mass% or less based on the total amount of the photosensitive resin composition, and may be 3 mass% or less based on the total amount of component (A).

In the photosensitive resin composition of the present disclosure, the content of component (E) is preferably 1 part by mass to 10,000 parts by mass, and more preferably 50 parts by mass to 10,000 parts by mass, per 100 parts by mass of component (A).

The photosensitive resin composition of the present disclosure may contain at least one of the following, as necessary: (F) a sensitizer (excluding component (D)); (G) a coupling agent, a thermal polymerization initiator, a polymerization inhibitor, an antioxidant, a surfactant, a leveling agent, a rust inhibitor, a nitrogen-containing compound, a dicarboxylic acid, a filler, etc.

((F) Sensitizer)
The photosensitive resin composition of the present disclosure may contain a sensitizer (F) (hereinafter also referred to as "component (F)"). Examples of the sensitizer (F) include Michler's ketone, benzoin, 2-methylbenzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, 2-t-butylanthraquinone, 1,2-benzo-9,10-anthraquinone, anthraquinone, methylanthraquinone, 4,4'-bis-(diethylamino)benzophenone, acetophenone, benzophenone, thioxanthone, 1,5-acenaphthene, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-[4-(methylthio)phenyl]-2-morpholino-1-propanone, diacetyl benzyl, benzyl dimethyl ketal, benzyl diethyl ketal, and the like. Examples of the suitable amines include tar, diphenyl disulfide, anthracene, phenanthrenequinone, riboflavin tetrabutylate, acridine orange, erythrosine, phenanthrenequinone, 2-isopropylthioxanthone, 2,6-bis(p-diethylaminobenzylidene)-4-methyl-4-azacyclohexanone, 6-bis(p-dimethylaminobenzylidene)-cyclopentanone, 2,6-bis(p-diethylaminobenzylidene)-4-phenylcyclohexanone, aminostyryl ketone, 3-ketocoumarin compounds, biscoumarin compounds, N-phenylglycine, N-phenyldiethanolamine, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, and compounds represented by the following formula:
The component (F) may be used alone or in combination of two or more types.

When the photosensitive resin composition of the present disclosure contains component (F), the content of component (F) is not particularly limited, but is preferably 0.1 parts by mass to 3 parts by mass, and more preferably 0.1 parts by mass to 2 parts by mass, per 100 parts by mass of component (A).

((G) Coupling Agent)
The photosensitive resin composition of the present disclosure may contain a coupling agent (G) (hereinafter also referred to as “component (G)”).

The coupling agent (G) is not particularly limited, and examples thereof include 3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinopropylsilane, diethoxy-3-glycidoxypropylmethylsilane, N-(3-diethoxymethylsilylpropyl)succinimide, N-[3-(triethoxysilyl)propyl]phthalamic acid, benzophenone-3,3'-bis(N-[3-triethoxysilyl]propylamide)-4,4'-dicarboxylic acid, benzene-1,4-bis(N-[3-triethoxysilyl]propylamide) )-2,5-dicarboxylic acid, 3-(triethoxysilyl)propyl succinic anhydride, N-phenylaminopropyl trimethoxysilane, N,N'-bis(2-hydroxyethyl)-3-aminopropyl triethoxysilane, ureidomethyl trimethoxysilane, ureidomethyl triethoxysilane, 2-ureidoethyl trimethoxysilane, 2-ureidoethyl triethoxysilane, 3-ureidopropyl trimethoxysilane, 3-ureidopropyl triethoxysilane, 4-ureidobutyl trimethoxysilane, 4-ureidobutyl triethoxysilane and other silane coupling agents; aluminum-based adhesion aids such as aluminum tris(ethyl acetoacetate), aluminum tris(acetylacetonate), and ethyl acetoacetate aluminum diisopropylate; and the like.
The component (G) may use one type alone, or two or more types in combination.

When the photosensitive resin composition of the present disclosure contains a coupling agent (G), the content of the coupling agent is not particularly limited, and is preferably 0.1 to 20 parts by mass, more preferably 0.3 to 10 parts by mass, and even more preferably 1 to 10 parts by mass, per 100 parts by mass of component (A).

(Thermal Polymerization Initiator)
The photosensitive resin composition of the present disclosure may contain a thermal polymerization initiator.

The thermal polymerization initiator is not particularly limited, and is preferably a compound that does not decompose when heated (dried) to remove the solvent during film formation, but decomposes when heated during curing to generate radicals, and promotes a polymerization reaction between the (B) components, or between the (A) and (B) components.
The thermal polymerization initiator is preferably a compound having a decomposition point of 110° C. or higher and 200° C. or lower, and from the viewpoint of promoting the polymerization reaction at a lower temperature, a compound having a decomposition point of 110° C. or higher and 175° C. or lower is more preferable.

Thermal polymerization initiators are not particularly limited and include ketone peroxides such as methyl ethyl ketone peroxide, peroxyketals such as 1,1-di(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(t-hexylperoxy)cyclohexane, and 1,1-di(t-butylperoxy)cyclohexane, hydroperoxides such as 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, and p-menthane hydroperoxide, dialkyl peroxides such as dicumyl peroxide and di-t-butyl peroxide, Examples of such peroxides include diacyl peroxides such as dilauroyl peroxide and dibenzoyl peroxide, peroxydicarbonates such as di(4-t-butylcyclohexyl)peroxydicarbonate and di(2-ethylhexyl)peroxydicarbonate, peroxyesters such as t-butylperoxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxybenzoate and 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, and bis(1-phenyl-1-methylethyl)peroxide. Commercially available products include those under the trade names "Percumyl D", "Percumyl P", and "Percumyl H" (all manufactured by NOF Corporation).

When the photosensitive resin composition of the present disclosure contains a thermal polymerization initiator, the content of the thermal polymerization initiator is preferably 0.1 parts by mass to 20 parts by mass relative to 100 parts by mass of component (A), more preferably 0.2 parts by mass to 20 parts by mass to ensure good flux resistance, and even more preferably 0.3 parts by mass to 10 parts by mass from the viewpoint of suppressing a decrease in solubility due to decomposition during drying.

The method for preparing the photosensitive resin composition of the present disclosure is not particularly limited, and it is sufficient to mix the aforementioned components.

<Cured Product>
The cured product of the present disclosure can be obtained by curing the above-mentioned photosensitive resin composition.
The cured product of the present disclosure may be used as a patterned cured product or as a non-patterned cured product.
The film thickness of the cured product of the present disclosure is preferably 5 μm to 20 μm.

<Method of producing a patterned cured product>
The method for producing a patterned cured product of the present disclosure includes a step of applying the above-mentioned photosensitive resin composition onto a substrate and drying to form a photosensitive resin film, a step of exposing the photosensitive resin film to a pattern to obtain a resin film, a step of developing the resin film after the pattern exposure using an organic solvent to obtain a patterned resin film, and a step of heat-treating the patterned resin film.
In this way, a patterned cured product can be obtained.

The method for producing a patternless cured product includes, for example, the steps of forming the above-mentioned photosensitive resin film and performing a heat treatment. It may further include a step of exposing the material to light.

Examples of the substrate include semiconductor substrates such as glass substrates and Si substrates (silicon wafers), metal oxide insulator substrates such as _TiO2 substrates and _SiO2 substrates, silicon nitride substrates, copper substrates, and copper alloy substrates.

The coating method is not particularly limited, and can be carried out using, for example, a spinner.
The drying can be carried out using a hot plate, an oven, or the like.
The drying temperature is preferably from 90° C. to 150° C., and from the viewpoint of ensuring the dissolution contrast, it is more preferably from 90° C. to 120° C.
The drying time is preferably from 30 seconds to 5 minutes.
The drying may be carried out two or more times.
In this way, a photosensitive resin film can be obtained in which the above-mentioned photosensitive resin composition is formed into a film shape.

The thickness of the photosensitive resin film is preferably 5 μm to 100 μm, more preferably 6 μm to 50 μm, and even more preferably 7 μm to 30 μm.

The pattern exposure is performed by exposing a predetermined pattern through a photomask, for example.
The actinic rays to be irradiated include ultraviolet rays such as i-rays and h-rays, visible light, and radiation, and are preferably h-rays.
As the exposure device, a parallel exposure device, a projection exposure device, a stepper, a scanner exposure device, or the like can be used.

By developing, a resin film having a pattern formed thereon (patterned resin film) can be obtained. In general, when a negative type photosensitive resin composition is used, the unexposed areas are removed with a developer.
The organic solvent used as the developer may be a good solvent for the photosensitive resin film, or a suitable mixture of a good solvent and a poor solvent.
Examples of the good solvent include N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, γ-butyrolactone, α-acetyl-γ-butyrolactone, cyclopentanone, and cyclohexanone.
Examples of the poor solvent include toluene, xylene, methanol, ethanol, isopropanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and water.

A surfactant may be added to the developer. The amount added is preferably 0.01 to 10 parts by weight, and more preferably 0.1 to 5 parts by weight, per 100 parts by weight of the developer.

The development time can be set to, for example, twice the time required for the photosensitive resin film to be immersed and completely dissolved.
The development time varies depending on the component (A) used, but is preferably from 10 seconds to 15 minutes, more preferably from 10 seconds to 5 minutes, and from the viewpoint of productivity, further preferably from 20 seconds to 5 minutes.

After development, washing may be carried out with a rinsing solution.
As the rinse liquid, distilled water, methanol, ethanol, isopropanol, toluene, xylene, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, etc. may be used alone or in appropriate mixture, or in stepwise combination.

By subjecting the patterned resin film to a heat treatment, a patterned cured product can be obtained.
The polyimide precursor of component (A) undergoes a dehydration ring-closing reaction during the heat treatment step, usually resulting in the corresponding polyimide.

The temperature of the heat treatment is preferably 250°C or lower, more preferably 120°C to 250°C, and even more preferably 200°C or lower or 160°C to 200°C.
By keeping the amount within the above range, damage to substrates, devices, etc. can be kept small, devices can be produced with a high yield, and energy savings can be achieved in the process.

The heat treatment time is preferably 5 hours or less, and more preferably 30 minutes to 3 hours.
Within the above range, the crosslinking reaction or the dehydration ring-closing reaction can proceed sufficiently.
The heat treatment may be performed in air or in an inert atmosphere such as nitrogen, but is preferably performed in a nitrogen atmosphere from the viewpoint of preventing oxidation of the patterned resin film.

Equipment used for heat treatment includes quartz tube furnaces, hot plates, rapid thermal annealing, vertical diffusion furnaces, infrared curing furnaces, electron beam curing furnaces, microwave curing furnaces, etc.

The cured product of the present disclosure can be used as a passivation film, a buffer coat film, an interlayer insulating film, a cover coat layer, a surface protective film, etc.
Using one or more selected from the group consisting of the above passivation film, buffer coat film, interlayer insulating film, cover coat layer, and surface protection film, highly reliable electronic components such as semiconductor devices, multilayer wiring boards, various electronic devices, and stacked devices (multi-die fan-out wafer level packages, etc.) can be manufactured.

An example of a manufacturing process for a semiconductor device, which is an electronic component according to the present disclosure, will be described with reference to the drawings.
FIG. 1 is a manufacturing process diagram of a semiconductor device having a multilayer wiring structure, which is an electronic component according to an embodiment of the present disclosure.
1, a semiconductor substrate 1 such as a Si substrate having circuit elements is covered with a protective film 2 such as a silicon oxide film except for a predetermined portion of the circuit elements, and a first conductor layer 3 is formed on the exposed circuit elements. Then, an interlayer insulating film 4 is formed on the semiconductor substrate 1.

Next, a photosensitive resin layer 5, such as a chlorinated rubber or phenol novolac type, is formed on the interlayer insulating film 4, and windows 6A are provided using known photoetching techniques to expose predetermined portions of the interlayer insulating film 4.

The interlayer insulating film 4 from which the window 6A is exposed is selectively etched to provide a window 6B.
Next, the photosensitive resin layer 5 is completely removed using an etching solution that corrodes only the photosensitive resin layer 5 without corroding the first conductor layer 3 exposed from the window 6B.

Further, a second conductor layer 7 is formed by using a known photolithography technique, and is electrically connected to the first conductor layer 3 .
When forming a multi-layer wiring structure having three or more layers, the above-mentioned steps can be repeated to form each layer.

Next, the above-mentioned photosensitive resin composition is used to open windows 6C by pattern exposure to form a surface protective film 8. The surface protective film 8 protects the second conductor layer 7 from external stress, α-rays, etc., and the resulting semiconductor device has excellent reliability.
In the above example, the interlayer insulating film can also be formed using the photosensitive resin composition of the present disclosure.

The present disclosure will be explained in more detail below based on examples and comparative examples. Note that the present disclosure is not limited to the following examples.

(Synthesis Example 1 (Synthesis of Polyimide Precursor A1))
7.07 g of 3,3',4,4'-biphenylethertetracarboxylic dianhydride (ODPA) and 4.12 g of 2,2'-dimethylbiphenyl-4,4'-diamine (DMAP) were dissolved in 30 g of N-methyl-2-pyrrolidone (NMP), and the mixture was stirred at 30°C for 4 hours and then at room temperature overnight to obtain polyamic acid. 9.45 g of trifluoroacetic anhydride was added thereto under water cooling, and the mixture was stirred at 45°C for 3 hours, and 7.08 g of 2-hydroxyethyl methacrylate (HEMA) was added. This reaction solution was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyimide precursor A1.
The weight average molecular weight of the polyimide precursor A1 was determined by gel permeation chromatography (GPC) in terms of standard polystyrene. The weight average molecular weight of the polyimide precursor A1 was 40000. Specifically, a solution in which 0.5 mg of the polyimide precursor A1 was dissolved in 1 mL of a solvent [tetrahydrofuran (THF)/dimethylformamide (DMF)=1/1 (volume ratio)] was used, and the measurement was performed under the following conditions.
(Measurement conditions)
Measurement equipment: Detector: Hitachi L4000UV
Pump: Hitachi L6000
Shimadzu Corporation C-R4A Chromatopac
Measurement conditions: Column Gelpack GL-S300MDT-5 x 2 Eluent: THF/DMF = 1/1 (volume ratio)
LiBr (0.03 mol/L), H ₃ PO ₄ (0.06 mol/L)
Flow rate: 1.0 mL/min, detector: UV 270 nm

The esterification rate of the polyimide precursor A1 (the reaction rate of the carboxyl groups of ODPA with HEMA) was calculated by NMR measurement under the following conditions: The esterification rate was 80 mol % based on the total carboxyl groups of the polyamic acid (the remaining 20 mol % was carboxyl groups).
Measuring equipment: Bruker Biospin AV400M
Magnetic field strength: 400MHz
Reference material: tetramethylsilane (TMS)
Solvent: dimethyl sulfoxide (DMSO)

(Preparation of Photosensitive Resin Composition)
Photosensitive resin compositions of Examples 1 to 5 and Comparative Examples 1 and 2 were prepared using the components and amounts shown in Tables 1 and 2. The units of the amounts of each component in Tables 1 and 2 are parts by mass, and blanks in Tables 1 and 2 indicate that the component was not used. The components used are as follows.

(A) Component A1: Polyimide precursor synthesized in Synthesis Example 1 (B) Component (polymerizable monomer not containing a cyclic skeleton)
B1: Tetraethylene glycol dimethacrylate (TEGDMA)
B2: Ethoxylated pentaerythritol tetraacrylate (ATM-4E, total number of ethoxy groups: 4)
Component (B)′ (polymerizable monomer containing a cyclic skeleton)
B'1: A-DCP (tricyclodecane dimethanol diacrylate)
(C) Component C1: PDO (1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime)
C2: Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime)
(D) Component D1: 9,10-diethoxyanthracene D2: 9,10-dibutoxyanthracene (E) Component E1: N-methyl-2-pyrrolidone E2: 3-methoxy-N,N-dimethylpropionamide (F) Component F1: 4,4'-bis(diethylamino)benzophenone (G) Component Thermal Polymerization Initiator G1: Bis(1-phenyl-1-methylethyl)peroxide (H) Component H1: 3-ureidopropyltriethoxysilane H2: Benzotriazole H3: 5-amino-1H-tetrazole

(Measurement of remaining film rate after development 1)
The obtained photosensitive resin composition was spin-coated on a silicon wafer using a coating device Act8 (manufactured by Tokyo Electron Limited), and dried at 110°C for 2 minutes, and then dried at 120°C for 2 minutes to form a photosensitive resin film having a dry thickness of about 13 µm.
The resulting photosensitive resin film was immersed in cyclopentanone and the developing time was set to twice the time required for the film to be completely dissolved.
In addition, a photosensitive resin film was prepared in the same manner as above, and the obtained photosensitive resin film was exposed to h-rays (wavelength 405 nm, irradiation intensity 2.3 mW/ ^cm2 ) using a mask aligner MA-8 (manufactured by SUSS MicroTec) with an h-ray bandpass filter. Note that in Example 1 and Comparative Example 2, the curing reaction proceeded with a relatively low cumulative irradiation dose, and 100, 150, 200, or 300 mJ/ ^cm2 of h-rays were irradiated.
The exposed resin film was paddle-developed in cyclopentanone using Act8 for the above-mentioned developing time, and then rinsed with propylene glycol monomethyl ether acetate (PGMEA) to obtain a resin film.
Regarding the film thickness after heating for 2 minutes on a hot plate at 120° C. and the film thickness after development, a part of the film was scribed to expose the silicon wafer, and the height from the exposed silicon wafer surface to the film surface was measured using a needle-type profiler Dektak 150 (manufactured by Bruker) (the film thickness was measured in the same manner below).
The film thickness after development (10 μm) was divided by the film thickness after heating on a hot plate at 120° C. for 2 minutes, and then expressed as a percentage to determine the remaining film rate after development.
The results are shown in Tables 3 and 4.

(Undercut evaluation)
The above-mentioned photosensitive resin composition was spin-coated on a silicon wafer using a coating device Act8, and then dried at 110° C. for 2 minutes, and then dried at 120° C. for 2 minutes to form a photosensitive resin film having a dry thickness of about 13 μm.
The resulting photosensitive resin film was immersed in cyclopentanone and the developing time was set to twice the time required for the film to be completely dissolved.
In addition, a photosensitive resin film was prepared in the same manner as above, and the obtained photosensitive resin film was exposed to h-rays (wavelength 405 nm, irradiation intensity 2.3 mW/ ^cm2 ) using a mask aligner MA-8 (manufactured by SUSS MicroTec) with an h-ray bandpass filter. Note that in Example 1 and Comparative Example 2, the curing reaction proceeded with a relatively low cumulative irradiation dose, and 100, 150, 200, or 300 mJ/ ^cm2 of h-rays were irradiated.
The exposed resin film was paddle-developed in cyclopentanone using Act8 for the above-mentioned developing time, and then rinsed with propylene glycol monomethyl ether acetate (PGMEA) to obtain a resin film.
The cross section of the 20 μm via opening of the obtained patterned resin film was observed by an optical microscope and an SEM, and the case where no undercut was found was rated A, and the case where an undercut was found was rated B. The results are shown in Tables 3 and 4.

(Evaluation of Warpage Amount)
The above-mentioned photosensitive resin composition was spin-coated on a 6-inch silicon wafer using a coating device Act8, and then dried at 110°C for 2 minutes, and then dried at 120°C for 2 minutes to form a photosensitive resin film with a dry thickness of about 13 μm. After that, using a mask aligner MA-8 (manufactured by SUSS MicroTec), the wafer was irradiated with UV light at 400 mJ/ ^cm2 and heat-treated in a nitrogen atmosphere at 200°C for 2 hours.
The amount of warping of the 6-inch silicon wafer with the cured photosensitive resin film was measured using a laser displacement meter LK-G5000 (manufactured by Keyence Corporation).
Of the obtained warpage amounts, those that were 20 μm or less were rated A, and those that were more than 20 μm were rated B. The results are shown in Tables 3 and 4.

As shown in Tables 3 and 4, in Examples 1 to 5, the residual film rate after development was superior to that in Comparative Examples 1 and 2, and the amount of warping was also suppressed.
Furthermore, in Examples 1 to 5, while having the same level of residual film rate after development as in Comparative Example 2, the occurrence of undercut was suppressed more than in Comparative Example 1.

The disclosure of Japanese Patent Application No. 2023-188829, filed on November 2, 2023, is incorporated herein by reference in its entirety.
All publications, patent applications, and standards mentioned in this specification are herein incorporated by reference to the same extent as if each individual publication, patent application, or standard was specifically and individually indicated to be incorporated by reference.

Claims (11)

(A) a polyimide precursor;
(B) a polymerizable monomer not containing a cyclic skeleton;
(C) a photopolymerization initiator; and
(D) a compound containing an anthracene structure;
Including,
The content of the polymerizable monomer having a cyclic skeleton is 20 mass % or less based on the total amount of the polyimide precursor (A). The photosensitive resin composition according to claim 1, further comprising (E) a solvent. The photosensitive resin composition according to claim 1, wherein the polymerizable monomer (B) includes a (meth)acrylic compound containing two (meth)acrylic groups. The photosensitive resin composition according to claim 3, wherein the polymerizable monomer (B) includes a (meth)acrylic compound containing three or more (meth)acrylic groups. The photosensitive resin composition according to claim 1 , wherein the polyimide precursor contains a compound having a structural unit represented by the following general formula (1):


In general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, ^R6 and ^R7 each independently represent a hydrogen atom or a monovalent organic group, and at least one of ^R6 and ^R7 has a polymerizable unsaturated bond. The photosensitive resin composition according to claim 1 , wherein the compound (D) comprises a compound represented by the following general formula (D):


In general formula (D), R _x 's each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 atoms, or a halogen atom, and n represents an integer of 0 to 10. The photosensitive resin composition according to claim 1, wherein the compound (D) includes at least one selected from the group consisting of dibutoxyanthracene, dimethoxyanthracene, diethoxyanthracene, and diethoxyethylanthracene. The photosensitive resin composition according to claim 1, further comprising (F) a thermal polymerization initiator. The photosensitive resin composition according to claim 1, which is for use in panel level packaging. A step of applying the photosensitive resin composition according to any one of claims 1 to 9 onto a substrate and drying the composition to form a photosensitive resin film;
a step of exposing the photosensitive resin film to a pattern to obtain a resin film;
developing the resin film after the patterned exposure with an organic solvent to obtain a patterned resin film;
and heat-treating the patterned resin film. A cured product obtained by curing the photosensitive resin composition according to any one of claims 1 to 9.