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

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

[0001] The present disclosure relates to a photosensitive resin composition, a method for producing a patterned cured product, and the cured product.

[0002] Conventionally, polyimides, polybenzoxazoles, and the like, which have excellent heat resistance, electrical properties, mechanical properties, and the like, have been used for surface protection films and interlayer insulating films of semiconductor elements. In recent years, photosensitive resin compositions in which these resins themselves are given photosensitivity have been used. The use of such photosensitive resin compositions can simplify the manufacturing process of patterned cured products and shorten complicated manufacturing processes (see, for example, Patent Document 1).

[0003] In recent years, 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 further performance and speed have been attracting attention.

[0004] Among stacked device structures, multi-die fanout wafer level packaging is a package manufactured by collectively sealing multiple dies in one package, and is attracting a great deal of attention because it is expected to achieve lower costs and higher performance than the conventional fanout wafer level package (manufactured by sealing one die in one package).

[0005] In the production of multi-die fan-out wafer-level packages, low-temperature curing is highly required from the viewpoint of protecting high-performance dies, protecting encapsulating materials with low heat resistance, and improving yields (see, for example, Patent Document 2).

[0006] Furthermore, a resin composition containing a polyimide precursor has been disclosed (see, for example, Patent Document 3).

[0007] JP 2009-265520 A International Publication No. 2008 / 111470 JP 2016-199662 A

[0008] Photosensitive resin compositions containing polyimide precursors and the like are required to have improved reactivity upon exposure to light, and 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 to be able to suppress the occurrence of warpage after curing.

[0009] The present disclosure aims to provide a photosensitive resin composition that is excellent in reactivity and capable of suppressing warpage 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.

[0010] Specific means for achieving the above object are as follows. <1> A photosensitive resin composition comprising: (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, wherein 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. <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 (B) polymerizable monomer contains a (meth)acrylic compound containing two (meth)acrylic groups. <4> The photosensitive resin composition according to any one of <1> to <3>, wherein the (B) polymerizable monomer contains a (meth)acrylic compound containing 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):

[0011]

[0012] In general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, and R ６ and R ７ each independently represents a hydrogen atom or a monovalent organic group; R ６ and R ７ <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):

[0013]

[0014] In general formula (D), R ｘ are each independently 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 is an integer of 0 to 10. <7> The photosensitive resin composition according to any one of <1> to <6>, wherein the (D) compound 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 including (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 method for producing a patterned cured product, comprising the steps of: applying the photosensitive resin composition according to any one of <1> to <9> onto a substrate and drying to form a photosensitive resin film; exposing the photosensitive resin film to light in a pattern to obtain a resin film; developing the resin film after pattern exposure using 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>.

[0015] According to the present disclosure, it is possible to provide a photosensitive resin composition that has excellent reactivity and is capable of suppressing warpage 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.

[0016] 1A to 1C are diagrams illustrating a manufacturing process for an electronic component according to an embodiment of the present disclosure.

[0017] Modes for carrying out the present disclosure are described in detail below. However, the present disclosure is not limited to the following embodiments. In the present disclosure, components (including elementary 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 "process" includes not only processes that are independent of other processes, but also processes that cannot be clearly distinguished from other processes as long as the purpose of the process is achieved. In the present disclosure, 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 stages in the present disclosure, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit of that numerical range may be replaced with a value shown in the examples. In the present disclosure, each component may contain multiple corresponding substances. When a composition contains multiple substances corresponding to each component, the content or amount of each component refers to the total content or amount of the multiple substances present in the composition, unless otherwise specified. In this disclosure, the terms "layer" and "film" include cases where the layer or film is formed over the entire area when the layer or film is observed, as well as cases where the layer or film is formed only in a portion of the area. In this disclosure, the thickness of a layer or film is determined by measuring the thickness at five points on the layer or film in question and calculating the arithmetic mean value. The thickness of a layer or film can be measured using a micrometer or the like. In this disclosure, if the thickness of a layer or film can be measured directly, it is measured using a micrometer. On the other hand, when measuring the thickness of a single layer or the total thickness of multiple layers, it may be measured by observing the cross-section of the target object using an electron microscope.

[0018] In the present disclosure, the term "(meth)acrylic group" refers to an "acrylic group" and a "methacrylic group," "(meth)acrylate" refers to an "acrylate" and a "methacrylate," and "(meth)acryloyl" refers to an "acryloyl" and a "methacryloyl." In the present disclosure, when a functional group has a substituent, the number of carbon atoms in the functional group refers to the total number of carbon atoms including the number of carbon atoms in the substituent. When embodiments in the present disclosure are described with reference to drawings, the configuration of the embodiment is not limited to the configuration shown in the drawings. Furthermore, the sizes of components in each drawing are conceptual, and the relative size relationships between components are not limited thereto.

[0019] <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.

[0020] The photosensitive resin composition of the present disclosure has excellent reactivity and can suppress warping after curing. The reason for this is presumed to be as follows. However, the present disclosure is not limited to the following presumption.

[0021] The photosensitive resin composition contains (A) a polyimide precursor and (D) a compound having an anthracene structure, and thus exhibits excellent reactivity upon exposure to light. For example, the composition tends to produce a cured product having excellent photosensitivity upon exposure to h-rays and a high film retention rate.

[0022] Furthermore, the photosensitive resin composition contains (B) a polymerizable monomer that does not contain a cyclic skeleton, and the content of the polymerizable monomer that contains a cyclic skeleton is 20% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total amount of (A) the polyimide precursor. This makes it possible to suppress warping after curing. The lower limit of the content of the polymerizable monomer that contains a cyclic skeleton is not particularly limited, and may be 0% by mass.

[0023] Furthermore, by using a polymerizable monomer having a cyclic skeleton and a compound having an anthracene structure (D), peeling (undercut) tends to occur at the bottom of the side surface of the opening of the cured product during production. In the present disclosure, by reducing the content of the polymerizable monomer having a cyclic skeleton, it is possible to suppress the undercut described above.

[0024] The photosensitive resin composition of the present disclosure is preferably a negative photosensitive resin composition. Furthermore, from the viewpoint of photosensitivity characteristics upon 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, but instead a structure in which wiring is drawn from chip terminals and connected to external terminals 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.

[0025] Hereinafter, each component contained in the photosensitive resin composition of the present disclosure will be described in detail.

[0026] ((A) Polyimide Precursor) The photosensitive resin composition of the present disclosure contains (A) a polyimide precursor (hereinafter also referred to as "component (A)").

[0027] 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. Polyamic acid ester and polyamic acid amide are compounds in which the hydrogen atoms of at least some of the carboxy groups in a polyamic acid are substituted with monovalent organic groups, and polyamic acid salt is a compound in which at least some of the carboxy groups in a polyamic acid form a salt structure with a basic compound having a pH of greater than 7. Component (A) may have a polymerizable unsaturated bond.

[0028] The component (A) preferably contains a compound having a structural unit represented by the following general formula (1): This tends to provide an electronic component having a cured product that exhibits high reliability.

[0029]

[0030] In general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, and R ６ and R ７ each independently represents a hydrogen atom or a monovalent organic group; R ６ and R ７ The polyimide precursor may have a plurality of structural units represented by the general formula (1), and X, Y, and R in the plurality of structural units may be ６ and R ７ may be the same or different. ６ and R ７ are each independently a hydrogen atom or a monovalent organic group, the combination of which is not particularly limited. For example, R ６ and R ７ At least one of R may be a hydrogen atom and the rest may be a monovalent organic group described later, or they may be the same or different monovalent organic groups. ６ and R ７ The combinations may be the same or different.

[0031] In general 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 on 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 one to three benzene rings, and even more preferably one or two benzene rings. When the tetravalent organic group represented by X contains two or more benzene rings, the benzene rings may be connected by a single bond, or may be connected by 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 -; Two R's Ａ each independently represents a hydrogen atom, an alkyl group, or a phenyl group; a siloxane bond (—O—(Si(R Ｂ ) ２ -O-) ｎ ;Two R's Ｂ each independently represent a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or greater.) or a composite linking group comprising at least two of these linking groups. Furthermore, two benzene rings may be linked at two positions by at least one of a single bond and a linking group to form a 5- or 6-membered ring containing a linking group between the two benzene rings.

[0032] In the general formula (1), -COOR ６The —COOR group and the —CONH— group are preferably in the ortho position relative to each other. ７ The group and the —CO— group are preferably in the ortho position relative to each other.

[0033] Specific examples of the tetravalent organic group represented by X include groups represented by the following formulas (A) to (F). Among them, from the viewpoint of obtaining a cured product excellent in flexibility, a group represented by the following formula (E) is preferred, and in the formula (E) below, C is more preferably a group containing an ether bond, and even more 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.

[0034]

[0035] In formula (D), A and B are each independently a single bond or a divalent group that is not conjugated with a benzene ring. However, both A and B cannot be single bonds. Examples of divalent groups that are 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 -; Two R's Ａ each independently represent a hydrogen atom, an alkyl group, or a phenyl group. Among these, A and B each independently preferably represent 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.

[0036] 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's Ａ each independently represents a hydrogen atom, an alkyl group, or a phenyl group; a siloxane bond (—O—(Si(R Ｂ ) ２ -O-) ｎ;Two R's Ｂ each 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 divalent group combining at least two of these. C preferably contains an ether bond, and is preferably an ether bond. C may also contain a structure represented by the following formula (C1):

[0037]

[0038] 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-dimethylethylene group, a branched-chain alkylene groups such as 1,2-dimethyltrimethylene, 2,2-dimethyltrimethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1-ethyltetramethylene, 2-ethyltetramethylene, 1,1-dimethyltetramethylene, 1,2-dimethyltetramethylene, 2,2-dimethyltetramethylene, 1,3-dimethyltetramethylene, 2,3-dimethyltetramethylene, and 1,4-dimethyltetramethylene; and the like. Among these, a methylene group is preferred.

[0039] 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) above has been 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.

[0040] R contained in the silylene bond or siloxane bond Ａ or R Ｂ The alkyl group represented by R 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. Ａ or R Ｂ Specific examples of the alkyl group represented by the formula (I) 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.

[0041] In general 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 the 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 (for example, an aromatic ring having 6 to 20 carbon atoms) and a divalent aromatic heterocyclic group (for example, a heterocyclic ring having 5 to 20 atoms), and the like, with a divalent aromatic hydrocarbon group being preferred.

[0042] Specific examples of the divalent aromatic group represented by Y include groups represented by the following formula (G) and formula (H). Among these, from the viewpoint of obtaining a cured product excellent in 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, further 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.

[0043]

[0044] In formulas (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(R Ａ ) ２ -; Two R's Ａeach independently represents a hydrogen atom, an alkyl group, or a phenyl group; a siloxane bond (—O—(Si(R Ｂ ) ２ -O-) ｎ ;Two R's Ｂ each 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 divalent group combining at least two of them. D may also be a structure represented by the above formula (C1). Specific examples of D in formula (H) are the same as the specific examples of C in formula (E). As D in formula (H), each independently is preferably 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.

[0045] 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 formulas (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.

[0046] 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 formulas (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.

[0047] The halogenated alkyl group represented by R in formulas (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.

[0048] In formulae (G) to (H), n is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0049] Specific examples of the divalent aliphatic group represented by Y include a linear or branched alkylene group, a cycloalkylene group, and a divalent group having a polyalkylene oxide structure.

[0050] 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.

[0051] 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 and a cyclohexylene group.

[0052] 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.

[0053] 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 the 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 the 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, and an n-dodecyl group. Among these, a methyl group is preferred. 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 in the aryl group 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.

[0054] 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.

[0055]

[0056] 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.

[0057] In 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).

[0058] R ６ and R ７ each independently represents a hydrogen atom or a monovalent organic group, provided 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 a group represented by the following general formula (2), an ethyl group, an isobutyl group, or a t-butyl group, and even more 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, R ６ and R ７ 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 a base or the like.

[0059] Specific examples of the aliphatic hydrocarbon group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a t-butyl group, and among these, an ethyl group, an isobutyl group, and a t-butyl group are preferred.

[0060]

[0061] In general formula (2), R ８ ~R １０ each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms; R ｘ represents a divalent linking group.

[0062] R in general formula (2) ８ ~R １０ The aliphatic hydrocarbon group represented by R has 1 to 3 carbon atoms, preferably 1 or 2. ８ ~R １０ Specific examples of the aliphatic hydrocarbon group represented by the formula include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, etc., with a methyl group being preferred.

[0063] R in general formula (2) ８ ~R １０ As a combination of ８ and R ９ is a hydrogen atom, and R １０ is preferably a hydrogen atom or a methyl group.

[0064] R in general formula (2) 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. ｘ The number of carbon atoms in is preferably 1 to 10, more preferably 2 to 5, and even more preferably 2 or 3.

[0065] In general formula (1), R ６ and R ７ At least one of R is preferably a group represented by the general formula (2), ６ and R ７ It is more preferable that both of the above are groups represented by the general formula (2).

[0066] (A) When the polyimide precursor contains a compound having a structural unit represented by the above-mentioned general formula (1), R of all structural units contained in the compound ６ and R ７The ratio of the group R represented by general formula (2) to the total ６ and R ７ The proportion 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 proportion may be 0 mol% or more and less than 60 mol%.

[0067] The group represented by formula (2) is preferably a group represented by the following formula (2').

[0068]

[0069] In general formula (2'), R ８ ~R １０ each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms; and q represents an integer of 1 to 10.

[0070] In formula (2'), q is an integer of 1 to 10, preferably an integer of 2 to 5, and more preferably 2 or 3.

[0071] 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 content is not particularly limited, and may be 100 mol%.

[0072] The polyimide precursor (A) may be synthesized using a tetracarboxylic dianhydride and a diamine compound. In this case, in 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.

[0073] Specific examples of tetracarboxylic dianhydrides include pyromellitic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-biphenylethertetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, and 1,4,5,8-naphthalenetetracarboxylic 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 tetracarboxylic dianhydrides include 4,4'-oxydiphthalic dianhydride, 4,4'-sulfonyldiphthalic dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, cyclopentanone bisspironorbornane tetracarboxylic dianhydride, and 2,2-bis{4-(4'-phenoxy)phenyl}propane tetracarboxylic dianhydride. Among these, 3,3',4,4'-biphenyl ether tetracarboxylic dianhydride and 3,3',4,4'-biphenyl tetracarboxylic dianhydride are preferred. These tetracarboxylic dianhydrides may be used alone or in combination of two or more.

[0074] 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, 2,4'-diaminodiphenyl ether, and 2,4'-diaminodiphenyl ether. , 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-amino (aminophenyl)propane, 9,9-bis(4-aminophenyl)fluorene, 1,3-bis(3-aminophenoxy)benzene, 1,4-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,Examples of the diamine compound include 9-diaminononane, 2-methyl-1,10-diaminodecane, 1,4-cyclohexanediamine, 1,3-cyclohexanediamine, and diaminopolysiloxane. Preferred diamine compounds include 2,2'-dimethylbiphenyl-4,4'-diamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, and 1,3-bis(3-aminophenoxy)benzene. 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.

[0075] Having a structural unit represented by general formula (1), and R in general formula (1) ６ and R ７ The compound in which at least one of the above 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 and H ２ N-Y-NH ２ (b) A condensation reaction is carried out between a tetracarboxylic acid dianhydride and a diamine compound represented by the formula: ２ N-Y-NH ２ In an organic solvent, a polyamic acid solution is obtained by reacting a diamine compound represented by R—OH with the polyamic acid solution, and the compound represented by R—OH is added to the polyamic acid solution and reacted in an organic solvent to introduce an ester group. ２ N-Y-NH ２ In the diamine compound represented by the formula (1), Y is the same as Y in the general formula (1), and specific examples and preferred examples are also the same. In addition, in the compound represented by R—OH, R represents a monovalent organic group, and specific examples and preferred examples are the same as R in the general formula (1). ６ and R ７ The same applies to the case of the tetracarboxylic acid dianhydride represented by the general formula (8), H ２ N-Y-NH ２The diamine compound represented by the formula (I) 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, with 3-methoxy-N,N-dimethylpropanamide being preferred. A polyimide precursor may be synthesized by allowing a dehydration condensation agent to act on a polyamic acid solution together with the compound represented by R—OH. The dehydration condensation agent preferably includes at least one selected from the group consisting of trifluoroacetic anhydride, N,N'-dicyclohexylcarbodiimide (DCC), and 1,3-diisopropylcarbodiimide (DIC).

[0076] The compound contained in the polyimide precursor (A) is prepared by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R—OH to form a diester derivative, which is then converted into an acid chloride by reacting with a chlorinating agent such as thionyl chloride, and then reacting with a chlorinating agent such as thionyl chloride to form an acid chloride. ２ N-Y-NH ２ The compound contained in the polyimide precursor (A) can be obtained by reacting a diamine compound 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 with an acid chloride in the presence of a carbodiimide compound. ２ N-Y-NH ２ The compound contained in the polyimide precursor (A) can be obtained by reacting a diamine compound represented by the following general formula (8) with a diester derivative. ２ N-Y-NH ２ The polyamic acid is then isoimidized in the presence of a dehydration condensation agent such as trifluoroacetic anhydride, and then reacted with a compound represented by R—OH to obtain a polyamic acid. Alternatively, a compound represented by R—OH may be reacted in advance with a part of a tetracarboxylic dianhydride to obtain a partially esterified tetracarboxylic dianhydride and H ２ N-Y-NH ２Alternatively, the compound may be reacted with a diamine compound represented by the following formula:

[0077]

[0078] In the general formula (8), X is the same as X in the general formula (1), and specific examples and preferred examples are also the same.

[0079] (A) The compound represented by R—OH used in the synthesis of the above-mentioned compound contained in the polyimide precursor is R of the group represented by general formula (2). ｘ The compound represented by R-OH may be a compound having a hydroxy group bonded to the terminal methylene group of a group represented by general formula (2'), or a compound having a hydroxy group bonded to the terminal methylene group of a group represented by general formula (2'). 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, and 4-hydroxybutyl methacrylate, and among these, 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate are preferred.

[0080] The molecular weight of the (A) polyimide precursor is not particularly limited, and 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.

[0081] The photosensitive resin composition of the present disclosure may contain a resin other than the polyimide precursor (A). Examples of the other resin include, from the viewpoint of heat resistance, polyimide resin, novolac resin, acrylic resin, polyethernitrile resin, polyethersulfone resin, epoxy resin, polyethylene terephthalate resin, polyethylene naphthalate resin, and polyvinyl chloride resin. The other resin may be used alone or in combination of two or more.

[0082] In the photosensitive resin composition of the present disclosure, the content of the polyimide precursor (A) relative to the total amount of 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.

[0083] ((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 being able to polymerize favorably when used in combination with the photopolymerization initiator (C). From the viewpoint of improving crosslink density and improving 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. One type of polymerizable monomer may be used alone, or two or more types may be used in combination.

[0084] The polymerizable monomer (B) may contain a (meth)acrylic compound containing two (meth)acrylic groups (bifunctional (meth)acrylic compound), or may contain a (meth)acrylic compound containing three or more (meth)acrylic groups (polyfunctional (meth)acrylic compound), or may contain the above-mentioned bifunctional (meth)acrylic compound and polyfunctional (meth)acrylic compound.

[0085] 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; (meth)acrylic compounds containing two (meth)acrylic groups, such as 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, and 1,3-bis((meth)acryloyloxy)-2-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, and ethoxylated pentaerythritol tetraacrylate.

[0086] Component (B) may be tetraethylene glycol dimethacrylate, ethoxylated pentaerythritol tetraacrylate, or a mixture thereof.

[0087] The component (B) may be a polymerizable monomer containing a (meth)acrylic group, a polymerizable monomer other than a polymerizable monomer containing a (meth)acrylic group, or a combination thereof.

[0088] The polymerizable monomer other than the polymerizable monomer containing a (meth)acrylic group is not particularly limited, and examples thereof include styrene, divinylbenzene, 4-vinyltoluene, 4-vinylpyridine, N-vinylpyrrolidone, methylenebisacrylamide, N,N-dimethylacrylamide, and N-methylolacrylamide.

[0089] The component (B) is not limited to a compound 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 (for example, an oxirane ring).

[0090] When the photosensitive resin composition of the present disclosure contains the component (B), the content of the component (B) is not particularly limited, and is preferably 1 to 100 parts by mass, more preferably 5 to 75 parts by mass, even more preferably 10 to 50 parts by mass, and particularly preferably 25 to 45 parts by mass, relative to 100 parts by mass of the component (A).

[0091] When the 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.

[0092] (Photopolymerization Initiator (C)) 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 examples thereof include 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-ethoxypropanetrione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-3-ethoxypropanetrione-2-(O-benzoyl)oxime, 1-phenyl-3-ethoxypropanetrione-2-(O-ethoxycarbon ... 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 derivatives such as thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, and diethylthioxanthone; benzyl derivatives such as benzil, benzil dimethyl ketal, and benzyl-β-methoxyethyl acetal; benzoin derivatives such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin phenyl ether, methylbenzoin, ethylbenzoin, and propylbenzoin; N-arylglycines such as N-phenylglycine; peroxides such as benzoyl peroxide;Examples of suitable compounds include 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; 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, it is preferable that the component (C) contains an oxime-based compound. The component (C) may be used alone or in combination of two or more types.

[0093] 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.

[0094] The content of the component (C) is preferably 0.1 to 20 parts by mass, more preferably 1 to 20 parts by mass, even more preferably 2 to 10 parts by mass, and particularly preferably 3 to 6 parts by mass, per 100 parts by mass of the component (A).

[0095] (D) Compound Having an Anthracene Structure The photosensitive resin composition of the present disclosure preferably further contains (D) a compound having an anthracene structure (hereinafter also referred to as "component (D)").

[0096] From the viewpoint of achieving both sensitivity and resolution, the component (D) preferably contains a compound represented by general formula (D).

[0097]

[0098] In general formula (D), R ｘ are each independently 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 is an integer from 0 to 10.

[0099] 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.

[0100] 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 (for example, an n-butoxy group).

[0101] 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.

[0102] 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.

[0103] From the viewpoint of achieving both solubility in the photosensitive resin composition and photosensitive properties, component (D) preferably contains a dialkoxyanthracene (e.g., 9,10 dialkoxyanthracene) that 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). Examples of the substituent include a methyl group, an ethyl group, a t-butyl group, and an n-butyl group. Component (D) may be used alone or in combination of two or more types.

[0104] From the viewpoint of improving solubility in the photosensitive resin composition and photosensitive properties, the amount of the component (D) relative to 100 parts by mass of the component (A) 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.

[0105] (E) Solvent) The photosensitive resin composition of the present disclosure preferably further contains (E) a solvent (hereinafter also referred to as "component (E)").

[0106] The component (E) is not particularly limited, and examples thereof include ester solvents, ketone solvents, carbonate solvents, heterocyclic compound solvents, and amide solvents. The ester solvents, ketone solvents, carbonate solvents, and amide 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.

[0107] 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 compounds.

[0108]

[0109]

[0110] 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 ~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.

[0111] In formula (3), s is preferably 0. In formula (4), R ２ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. t is preferably 0, 1 or 2, more preferably 1. In formula (5), R ３ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group, an ethyl group, a propyl group, or a butyl group. ４ and R ５ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. ６ ~R ８ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. r is preferably 0 or 1, more preferably 0. In formula (7), R ９ and R １０ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. u is preferably 0 or 1, more preferably 0. In formula (8), R １１ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. u is preferably 0 or 1, more preferably 0. In formula (9), R １２ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. １３ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. w is preferably 0 or 1, more preferably 0. In formula (10), R １４ The alkyl group having 1 to 4 carbon atoms is preferably a methyl group or an ethyl group. x is preferably 0 or 1, and more preferably 0.

[0112] Specific examples of the component (E) include the following compounds:

[0113]

[0114] 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 relative to the total amount of the photosensitive resin composition, and may be 3 mass% or less relative to the total amount of the component (A).

[0115] In the photosensitive resin composition of the present disclosure, the content of the 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 the component (A).

[0116] The photosensitive resin composition of the present disclosure may contain, as necessary, at least one of a sensitizer (F) (excluding the component (D)), a coupling agent (G), 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, and the like.

[0117] (Sensitizer (F)) 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, diacetylbenzyl, benzil dimethyl ketal, and benzil diethyl ketone. Examples of the component (F) 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: Component (F) may be used singly or in combination of two or more.

[0118]

[0119] When the photosensitive resin composition of the present disclosure contains the component (F), the content of the component (F) is not particularly limited, but is preferably 0.1 to 3 parts by mass, and more preferably 0.1 to 2 parts by mass, per 100 parts by mass of the component (A).

[0120] (G) Coupling Agent) The photosensitive resin composition of the present disclosure may contain a (G) coupling agent (hereinafter also referred to as "component (G)").

[0121] 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, and benzene-1,4-bis(N-[3-triethoxysilyl]propylamide). )-2,5-dicarboxylic acid, 3-(triethoxysilyl)propyl succinic anhydride, N-phenylaminopropyltrimethoxysilane, N,N'-bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, ureidomethyltrimethoxysilane, ureidomethyltriethoxysilane, 2-ureidoethyltrimethoxysilane, 2-ureidoethyltriethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 4-ureidobutyltrimethoxysilane, 4-ureidobutyltriethoxysilane, and other silane coupling agents; aluminum-based adhesion promoters such as aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate; and the like. Component (G) may be used singly or in combination of two or more.

[0122] 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 parts by mass to 20 parts by mass, more preferably 0.3 parts by mass to 10 parts by mass, and even more preferably 1 part by mass to 10 parts by mass, per 100 parts by mass of the component (A).

[0123] (Thermal Polymerization Initiator) The photosensitive resin composition of the present disclosure may contain a thermal polymerization initiator.

[0124] 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 component (B) itself or between component (A) and component (B). The thermal polymerization initiator is preferably a compound whose decomposition point is 110°C or higher and 200°C or lower, and more preferably a compound whose decomposition point is 110°C or higher and 175°C or lower, from the viewpoint of promoting a polymerization reaction at a lower temperature.

[0125] The thermal polymerization initiator is not particularly limited, and examples thereof 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).

[0126] 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, more preferably 0.2 parts by mass to 20 parts by mass in order to ensure good flux resistance, and even more preferably 0.3 parts by mass to 10 parts by mass in order to suppress a decrease in solubility due to decomposition during drying, relative to 100 parts by mass of the component (A).

[0127] The method for preparing the photosensitive resin composition of the present disclosure is not particularly limited, and it is sufficient to mix the above-mentioned components.

[0128] <Cured Product> The cured product of the present disclosure can be obtained by curing the above-described 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.

[0129] <Method for producing patterned cured product> The method for producing a patterned cured product according to the present disclosure includes the steps of applying the above-described photosensitive resin composition onto a substrate and drying to form a photosensitive resin film, patternwise exposing the photosensitive resin film to light to obtain a resin film, developing the patterned exposed resin film using an organic solvent to obtain a patterned resin film, and heat-treating the patterned resin film. This allows the production of a patterned cured product.

[0130] The method for producing a patternless cured product includes, for example, the steps of forming the above-described photosensitive resin film and performing a heat treatment. It may further include a step of exposing the film to light.

[0131] The substrate may be a glass substrate, a semiconductor substrate such as a Si substrate (silicon wafer), or a TiO ２ Substrate, SiO ２ Examples of the substrate include a metal oxide insulator substrate, a silicon nitride substrate, a copper substrate, and a copper alloy substrate.

[0132] The coating method is not particularly limited, and can be carried out using, for example, a spinner. Drying can be carried out using a hot plate, oven, or the like. The drying temperature is preferably 90°C to 150°C, and more preferably 90°C to 120°C from the viewpoint of ensuring dissolution contrast. The drying time is preferably 30 seconds to 5 minutes. Drying may be carried out two or more times. This makes it possible to obtain a photosensitive resin film in which the above-mentioned photosensitive resin composition is formed into a film.

[0133] 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.

[0134] The pattern exposure is carried out by exposing the film to a predetermined pattern through a photomask, for example. The actinic ray to be irradiated may be ultraviolet rays such as i-rays and h-rays, visible light, or radiation, but h-rays are preferred. The exposure device may be a parallel exposure device, a projection exposure device, a stepper, a scanner exposure device, or the like.

[0135] By developing, a patterned resin film (patterned resin film) can be obtained. Generally, when a negative photosensitive resin composition is used, unexposed areas are removed with a developer. The organic solvent used as the developer can be a good solvent for the photosensitive resin film, either alone or in combination with a poor solvent. Examples of good solvents include N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, γ-butyrolactone, α-acetyl-γ-butyrolactone, cyclopentanone, and cyclohexanone. Examples of poor solvents include toluene, xylene, methanol, ethanol, isopropanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and water.

[0136] A surfactant may be added to the developer in an amount of preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the developer.

[0137] The development time can be, 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 10 seconds to 15 minutes, more preferably 10 seconds to 5 minutes, and from the viewpoint of productivity, even more preferably 20 seconds to 5 minutes.

[0138] After development, the resist may be washed with a rinse solution, such as distilled water, methanol, ethanol, isopropanol, toluene, xylene, propylene glycol monomethyl ether acetate, or propylene glycol monomethyl ether, which may be used alone or in appropriate mixtures, or in stepwise combinations.

[0139] A patterned cured product can be obtained by heat-treating the patterned resin film. The polyimide precursor of component (A) undergoes a dehydration ring-closing reaction during the heat treatment step, usually to form the corresponding polyimide.

[0140] The temperature of the heat treatment is preferably 250° C. or less, more preferably 120° C. to 250° C., and even more preferably 200° C. or less or 160° C. to 200° C. By keeping the temperature within the above range, damage to the substrate, device, etc. can be minimized, devices can be produced with a high yield, and energy savings can be achieved in the process.

[0141] The heat treatment time is preferably 5 hours or less, more preferably 30 minutes to 3 hours. By keeping the time within the above range, the crosslinking reaction or the dehydration ring-closing reaction can be sufficiently progressed. The heat treatment atmosphere may be air or an inert atmosphere such as nitrogen, but a nitrogen atmosphere is preferred from the viewpoint of preventing oxidation of the patterned resin film.

[0142] Examples of equipment used for the heat treatment include a quartz tube furnace, a hot plate, a rapid thermal annealer, a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, and a microwave curing furnace.

[0143] 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. Highly reliable electronic components such as semiconductor devices, multilayer wiring boards, various electronic devices, and stacked devices (such as multi-die fan-out wafer-level packages) can be manufactured using one or more selected from the group consisting of the passivation film, buffer coat film, interlayer insulating film, cover coat layer, and surface protective film.

[0144] 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. Figure 1 is a diagram illustrating a manufacturing process for a semiconductor device with a multilayer wiring structure, which is an electronic component according to an embodiment of the present disclosure. In Figure 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 predetermined portions of the circuit elements, and a first conductor layer 3 is formed on the exposed circuit elements. An interlayer insulating film 4 is then formed on the semiconductor substrate 1.

[0145] Next, a photosensitive resin layer 5 such as a chlorinated rubber or phenol novolac resin is formed on the interlayer insulating film 4, and windows 6A are formed by known photoetching techniques so that predetermined portions of the interlayer insulating film 4 are exposed.

[0146] The interlayer insulating film 4 where the window 6 A is exposed is selectively etched to provide a window 6 B. 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 6 B.

[0147] Furthermore, a second conductor layer 7 is formed using a known photolithography technique, and electrically connected to the first conductor layer 3. When forming a multilayer wiring structure having three or more layers, the above steps can be repeated to form each layer.

[0148] Next, the above-described photosensitive resin composition is used to open windows 6C by pattern exposure, and a surface protective film 8 is formed. The surface protective film 8 protects the second conductor layer 7 from external stress, alpha 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.

[0149] The present disclosure will be described in more detail below based on examples and comparative examples, but the present disclosure is not limited to the following examples.

[0150] Synthesis Example 1 (Synthesis of Polyimide Precursor A1) 7.07 g of 3,3',4,4'-biphenyl ether tetracarboxylic 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, followed by the addition of 7.08 g of 2-hydroxyethyl methacrylate (HEMA). This reaction solution was added dropwise to 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 polyimide precursor A1 was determined using gel permeation chromatography (GPC) in terms of standard polystyrene. The weight-average molecular weight of polyimide precursor A1 was 40,000. Specifically, a solution prepared by dissolving 0.5 mg of polyimide precursor A1 in 1 mL of a solvent [tetrahydrofuran (THF) / dimethylformamide (DMF) = 1 / 1 (volume ratio)] was used, and the measurement was carried out under the following conditions. (Measurement conditions) Measurement device: Detector: Hitachi, Ltd. L4000UV Pump: Hitachi, Ltd. L6000 Pump: 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 P.O. ４ (0.06 mol / L) Flow rate: 1.0 mL / min, Detector: UV 270 nm

[0151] The esterification rate of 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 % of the total carboxyl groups of the polyamic acid (the remaining 20 mol % were carboxyl groups). Measuring equipment: AV400M manufactured by Bruker Biospin; Magnetic field strength: 400 MHz; Reference material: Tetramethylsilane (TMS); Solvent: Dimethyl sulfoxide (DMSO).

[0152] (Preparation of Photosensitive Resin Compositions) Photosensitive resin compositions of Examples 1 to 5 and Comparative Examples 1 and 2 were prepared using the components and blending amounts shown in Tables 1 and 2. The blending amount of each component in Tables 1 and 2 is in parts by mass, and blank spaces in Tables 1 and 2 indicate that the component was not blended. The components used are as follows:

[0153] Component (A) A1: Polyimide precursor synthesized in Synthesis Example 1 Component (B) (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) Component (C) 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)) Component (D) D1: 9,10-diethoxyanthracene D2: 9,10-dibutoxyanthracene Component (E): E1: N-methyl-2-pyrrolidone; E2: 3-methoxy-N,N-dimethylpropionamide; Component (F): F1: 4,4'-bis(diethylamino)benzophenone; Component (G): thermal polymerization initiator; G1: bis(1-phenyl-1-methylethyl)peroxide; Component (H): H1: 3-ureidopropyltriethoxysilane; H2: benzotriazole; H3: 5-amino-1H-tetrazole.

[0154]

[0155]

[0156] (Measurement 1 of the remaining film rate after development) The obtained photosensitive resin composition was spin-coated on a silicon wafer using a coating device Act8 (manufactured by Tokyo Electron Limited), 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 film thickness of approximately 13 μm. The resulting photosensitive resin film was immersed in cyclopentanone and the development time was set to twice the time until it was completely dissolved. In addition, a photosensitive resin film was prepared in the same manner as above, and the resulting photosensitive resin film was irradiated with h-rays (wavelength 405 nm, irradiation intensity 2.3 mW / cm) using an h-ray bandpass filter on a mask aligner MA-8 (manufactured by SUSS MicroTec). ２ In Example 1 and Comparative Example 2, the curing reaction proceeded at a relatively low cumulative dose of irradiation, and the exposure was 100, 150, 200, or 300 mJ / cm. ２ The resin film was irradiated with h-rays. The exposed resin film was paddle-developed in cyclopentanone using Act8 for the above-mentioned development time, and then rinsed with propylene glycol monomethyl ether acetate (PGMEA) to obtain a resin film. Regarding the film thickness after heating on a hot plate at 120 ° C for 2 minutes and the film thickness after development, a portion 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 same applies below for film thickness measurements). The film thickness of 10 μm after development was divided by the film thickness after heating on a hot plate at 120 ° C for 2 minutes, and then converted into a percentage to determine the remaining film ratio after development. The results are shown in Tables 3 and 4.

[0157] (Undercut Evaluation) The above-mentioned photosensitive resin composition was spin-coated onto a silicon wafer using a coating device Act8, and then dried at 110°C for 2 minutes, followed by drying at 120°C for 2 minutes to form a photosensitive resin film with a dry film thickness of approximately 13 μm. The resulting photosensitive resin film was immersed in cyclopentanone and the development time was set to twice the time required for complete dissolution. Further, a photosensitive resin film was prepared in the same manner as above, and the resulting photosensitive resin film was irradiated with h-rays (wavelength 405 nm, irradiation intensity 2.3 mW / cm) using a mask aligner MA-8 (manufactured by SUSS MicroTec) with an h-ray bandpass filter. ２In Example 1 and Comparative Example 2, the curing reaction proceeded at a relatively low cumulative dose of irradiation, and the exposure was 100, 150, 200, or 300 mJ / cm. ２ The exposed resin film was puddle-developed in cyclopentanone using Act8 for the above-mentioned development 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 using an optical microscope and an SEM. A was assigned to the case where no undercut was observed, and a B was assigned to the case where undercut was confirmed. The results are shown in Tables 3 and 4.

[0158] (Evaluation of Warpage) The above-mentioned photosensitive resin composition was spin-coated onto a 6-inch silicon wafer using a coating device Act8, and dried at 110°C for 2 minutes, and then at 120°C for 2 minutes to form a photosensitive resin film with a dry thickness of approximately 13 μm. Thereafter, a mask aligner MA-8 (manufactured by SUSS MicroTec) was used to spin-coat the wafer with a 400 mJ / cm ２ The wafers were then irradiated with UV light of 1000 nm and heat-treated in a nitrogen atmosphere at 200°C for 2 hours. The amount of warpage of the 6-inch silicon wafers with the cured photosensitive resin film was measured using a laser displacement meter LK-G5000 (manufactured by Keyence Corporation). Of the warpage amounts obtained, those that were 20 μm or less were rated A, and those that were greater than 20 μm were rated B. The results are shown in Tables 3 and 4.

[0159]

[0160]

[0161] As shown in Tables 3 and 4, Examples 1 to 5 had a better residual film rate after development and suppressed the amount of warpage than Comparative Examples 1 and 2. Furthermore, Examples 1 to 5 had a residual film rate after development similar to that of Comparative Example 2, while suppressing the occurrence of undercut more than Comparative Example 1.

[0162] The disclosure of Japanese Patent Application No. 2023-188829, filed on November 2, 2023, is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A photosensitive resin composition comprising: (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, wherein the content of the polymerizable monomer containing 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 claim 1, further comprising (E) a solvent.

3. The photosensitive resin composition according to claim 1, wherein the polymerizable monomer (B) comprises a (meth)acrylic compound containing two (meth)acrylic groups.

4. 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.

5. 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 the general formula (1), X represents a tetravalent organic group, Y represents a divalent organic group, R ６ and R ７ each independently represents a hydrogen atom or a monovalent organic group; R ６ and R ７ At least one of them has a polymerizable unsaturated bond.

6. 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 each independently represents 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 is an integer from 0 to 10.

7. The photosensitive resin composition according to claim 1, wherein the compound (D) comprises at least one member selected from the group consisting of dibutoxyanthracene, dimethoxyanthracene, diethoxyanthracene and diethoxyethylanthracene.

8. The photosensitive resin composition according to claim 1, further comprising (F) a thermal polymerization initiator.

9. The photosensitive resin composition according to claim 1, which is used for panel level packaging.

10. A method for producing a patterned cured product, comprising the steps of: applying the photosensitive resin composition according to any one of claims 1 to 9 onto a substrate and drying to form a photosensitive resin film; exposing the photosensitive resin film to a pattern to obtain a resin film; developing the resin film after the pattern exposure using 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 claims 1 to 9.