Photosensitive resin composition, cured product, method for producing cured product, and electronic component

Abstract

The present invention addresses the problem of providing a photosensitive resin composition which has high micromachining properties and can yield a cured product having a low dielectric loss tangent. The main purpose of the present invention is to obtain a photosensitive resin composition which contains a polyimide resin, a cationic polymerizable compound and a cationic polymerization initiator and which is characterized in that the polyimide resin has a structure represented by formula (1) as a tetracarboxylic acid residue in all or some tetracarboxylic acid residues. (X moieties are each independently a single bond or a divalent linking group (in which the total number of carbon atoms is 10 or fewer). Y is a phenylene group, a naphthylene group, a group represented by formula (2) or a group represented by formula (4). ＊ denotes a bond to an amide group or a carbonyl group in an imide ring) (In formula (2) and formula (4), R1 and R2 each independently denote a monovalent hydrocarbon group having 1-10 carbon atoms, in which some hydrogen atoms may be substituted by halogen atoms, Z denotes a single bond or a divalent organic group having 1-20 carbon atoms, p and q each independently denote an integer between 0 and 4, and s denotes an integer that is 0 or 1. ＊ denotes a bond to X.)

Description

Photosensitive resin composition, cured product, method for producing the cured product, and electronic component

[0001] The present invention relates to a photosensitive resin composition, a cured product, a method for producing the cured product, and an electronic component. More specifically, the present invention relates to a photosensitive resin composition suitable for use as a surface protective film or interlayer insulating film for electronic components such as semiconductor elements, an insulating layer for organic electroluminescent elements, and the like.

[0002] Conventionally, polyimide-based materials and polybenzoxazole-based materials, which have excellent heat resistance, electrical insulation, and mechanical properties, have been widely used for surface protection films and interlayer insulating films of semiconductor elements. However, with the recent demand for higher density and performance of semiconductor elements, photosensitive materials are required for surface protection films and interlayer insulating films from the viewpoint of production efficiency.

[0003] In response to the recent demand for higher performance in electronic components, surface protection films and interlayer insulating films are required to be processed with fine patterns and high aspect ratios. Furthermore, in high-frequency communication device applications for high-speed wireless communication, a reduction in the dielectric loss tangent of insulating films is required to reduce transmission loss.

[0004] Regarding the formation of fine patterns, cationically curable photosensitive resins have been disclosed (for example, Patent Document 1). Furthermore, methods for reducing the dielectric loss tangent include radically curable photosensitive resins containing polyimides with specific structures (Patent Document 2) and soluble polyimides using dimer diamines with low polarity structures (Patent Document 3).

[0005] International Publication No. 2021 / 059843 Japanese Patent Application Laid-Open No. 2022-73127 Japanese Patent Application Laid-Open No. 2018-203959

[0006] In recent years, with the miniaturization of patterns that contribute to improving semiconductor performance and the increasing frequency of communication signals, including 5G communications, semiconductor materials are required to have high resolution and low dielectric loss tangent. However, cationic curing materials with good resolution have high polarity of crosslinking agents, making it difficult to reduce the dielectric loss tangent. Furthermore, when using radical polymerization-based materials, which have traditionally been used in photosensitive materials with low dielectric loss tangent, it has been difficult to obtain fine patterns in the cured product, i.e., to improve microfabrication, due to dark reactions after exposure.

[0007] An object of the present invention is to provide a photosensitive resin composition that is highly microfabricable and that can give a cured product with a low dielectric loss tangent.

[0008] The present invention and its preferred embodiments for solving the above problems comprise the following: [1] A photosensitive resin composition containing a polyimide resin (component (A)), a cationically polymerizable compound (component (B)), and a cationic polymerization initiator, wherein component (A) has a structure represented by formula (1) as a tetracarboxylic acid residue in all or part of the tetracarboxylic acid residue.

[0009]

[0010] (Each X independently represents a single bond or a divalent linking group (having a total carbon number of 10 or less). Y represents a phenylene group, a naphthylene group, a group represented by formula (2), or a group represented by formula (4). * indicates the point of attachment to the amide group, carboxyl group, or carbonyl group of the imide ring.)

[0011]

[0012] (In formula (2) and formula (4), R １ and R ２ each independently represent a monovalent hydrocarbon group having 1 to 10 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms, Z represents a single bond or a divalent organic group having 1 to 20 carbon atoms, p and q each independently represent an integer from 0 to 4, and s represents an integer of 0 or 1. * represents the point of attachment to X.) [2] The photosensitive resin composition according to [1] above, wherein the imide group equivalent of component (A) is 300 g / eq. or more. [3] The photosensitive resin composition according to [1] above, wherein Z in formula (2) represents a single bond, a structure represented by formula (5), a structure represented by formula (6), or a structure represented by formula (7).

[0013]

[0014] (In formulas (5) to (7), R ３ and R ４each independently represent a monovalent hydrocarbon group having 1 to 9 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms, and t is an integer of 1 to 15. * represents the point of attachment to the benzene ring.) [4] The photosensitive resin composition according to any one of [1] to [3] above, wherein X in formula (1) is -O-. [5] The photosensitive resin composition according to any one of [1] to [4] above, wherein component (A) has a structure represented by formula (8) as a diamine residue in all or part of the diamine residue.

[0015]

[0016] (u represents an integer of 1 to 40. R ５ and R １０ R each independently represents an alkylene group having 1 to 15 carbon atoms. ６ ~R ９ each independently represent an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 10 carbon atoms. * represents a bonding point with the nitrogen atom.) [6] The photosensitive resin composition according to [5] above, wherein in component (A), when the total amount of structures represented by formula (1) as tetracarboxylic acid residues is A (moles) and the total amount of structures represented by formula (8) as diamine residues is B (moles), the ratio (B / A) is 0.30 or more and 1.40 or less. [7] The photosensitive resin composition according to any one of [1] to [6] above, wherein component (A) contains multiple types of tetracarboxylic acid residues corresponding to formula (1), and in the multiple types of tetracarboxylic acid residues corresponding to formula (1), the group represented by Y corresponds to any one of the following structures A to F, and at least two groups corresponding to any one of structures A to F are included. Structure A: A group represented by formula (2), in which Z is a single bond. Structure B: A group represented by formula (2), wherein Z has the structure shown in formula (5) below. Structure C: A group represented by formula (2), wherein Z has the structure shown in formula (6) below. Structure D: A group represented by formula (2), wherein Z has the structure shown in formula (7) below. Structure E: A phenylene group or a naphthylene group. Structure F: A group represented by formula (4).

[0017]

[0018] (In formulas (5) to (7), R ３and R ４ each independently represent a monovalent hydrocarbon group having 1 to 9 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms, t is an integer from 1 to 15, and * represents the point of attachment to the benzene ring.) [8] The photosensitive resin composition according to any one of [1] to [7] above, wherein all or part of component (B) is either an epoxy compound or an oxetane compound, or both. [9] The photosensitive resin composition according to any one of [1] to [7] above, comprising an epoxy compound and an oxetane compound as component (B), and the mass ratio thereof (epoxy compound content / oxetane compound content) is greater than zero and equal to or less than 1.

[10] The photosensitive resin composition according to any one of [1] to [7] and [9] above, comprising an oxetane compound as component (B), and the content of the oxetane compound is 70 to 200 parts by mass per 100 parts by mass of component (A).

[11] The photosensitive resin composition according to any one of [1] to

[10] above, wherein all or part of the component (B) is a compound represented by formula (12):

[0019]

[0020] (A １ represents an alkylene group having 1 to 20 carbon atoms or a divalent hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring; B １ and B ２each independently represents an ether bond or an ester bond.)

[12] A cured product obtained by curing the photosensitive resin composition according to any one of [1] to

[11] above.

[13] A method for producing a cured product using the photosensitive resin composition according to any one of [1] to

[11] above, the method comprising the steps of: applying the photosensitive resin composition on a substrate and drying it to form a photosensitive resin composition film; exposing the photosensitive resin composition film; developing the exposed photosensitive resin composition film; and curing the developed photosensitive resin composition film.

[14] An electronic component comprising the cured product according to

[12] above or a cured product obtained by the method for producing a cured product according to

[13] above.

[15] An electronic component in which the cured product according to

[12] above or a cured product obtained by the method for producing a cured product according to

[13] above is disposed as an insulating film between wirings.

[16] An electronic component including a semiconductor package having a semiconductor element, a rewiring layer, a ground terminal, an antenna wiring, and a sealing resin disposed between the ground terminal and the antenna wiring, wherein the insulating layer of the rewiring layer or the sealing resin comprises the cured product according to

[12] above or a cured product obtained by the method for producing a cured product according to

[13] above.

[0021] According to the present invention, it is possible to provide a photosensitive resin composition with high micro-processability that can give a cured product with a low dielectric loss tangent.

[0022] 1 is a schematic cross-sectional view illustrating a semiconductor package including an IC chip (semiconductor element), a rewiring layer, a sealing resin, and an antenna element.

[0023] The photosensitive resin composition of the present invention contains a polyimide resin (hereinafter referred to as "component (A)"), a cationically polymerizable compound (hereinafter referred to as "component (B)"), and a cationic polymerization initiator (hereinafter referred to as "component (C)"), and component (A) has a structure represented by formula (1) as a tetracarboxylic acid residue in all or part of the tetracarboxylic acid residue. That is, all or part of the tetracarboxylic acid residues of the polyimide resin have a structure represented by formula (1).

[0024]

[0025] (Each X independently represents a single bond or a divalent linking group (having a total carbon number of 10 or less). Y represents a phenylene group, a naphthylene group, a group represented by formula (2), or a group represented by formula (4). * indicates the point of attachment to the amide group, carboxyl group, or carbonyl group of the imide ring.)

[0026]

[0027] (In formula (2) and formula (4), R １ and R ２ each independently represent a monovalent hydrocarbon group having 1 to 10 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms; Z represents a single bond or a divalent organic group having 1 to 20 carbon atoms; p and q each independently represent an integer from 0 to 4; and s represents an integer of 0 or 1. * represents the point of attachment of the amide group or the imide ring to the carbonyl group.) Note that the * in formula (1) refers to the point of attachment of the amide group or the carboxyl group to the carbonyl group, assuming that the structure contains an amic acid structure or a polybenzoxazole precursor structure, which will be described later.

[0028] In the present invention, the terms "diamine residue" and "carboxylic acid residue" refer to partial structures other than the chemical bond portion (imide group in polyimide, amide acid structure in polyimide precursor) in the structure of a polymer compound, where a diamine residue is a partial structure obtained by removing the amino group portion of a diamine monomer (including derivatives that function equivalently as a monomer), and a carboxylic acid residue is a partial structure obtained by removing the carboxyl group portion of a carboxylic acid monomer (including derivatives that function equivalently as a monomer). Thus, in a polymer compound, a diamine residue is bonded to the nitrogen atom of the amino group provided for the chemical bond portion, and a carboxylic acid residue is bonded to the carbonyl carbon of the carboxyl group provided for the chemical bond.

[0029] First, the component (A) will be described. The component (A) has a structure represented by formula (1) as a tetracarboxylic acid residue.

[0030] When component (A) contains a structure represented by formula (1) as a tetracarboxylic acid residue, the imide group equivalent of component (A) is reduced, and the polarity of component (A) can be reduced, enabling high-resolution processing by photolithography and reducing the dielectric tangent of the cured product.

[0031] Component (A) refers to a repeating unit having an imide bond, but may also contain a repeating unit not having an imide bond, provided that the object of the present invention is not impaired. Examples of such repeating units include a repeating unit having an amide acid structure, a repeating unit having an amide structure, and a polybenzoxazole precursor structure.

[0032] In formula (1), each X independently represents a single bond or a divalent linking group. This divalent linking group is a divalent group that links Y in formula (1) to the benzene ring, and is, for example, —O—, —SO ２ Examples of such groups include -, -S-, -COO-, -CO-, -CONH-, -NHCOO-, -NHCONH-, alkylene groups having 1 to 10 carbon atoms, and alkenylene groups having 1 to 10 carbon atoms, and also include combinations of these. However, the total number of carbon atoms in the divalent linking group is 10 or less. X is preferably -O-, that is, an ether bond, because this does not inhibit the initiation reaction of cationic polymerization by acid generated during exposure and results in good cationic curability.

[0033] In formula (1), Y is a phenylene group, a naphthylene group, a group represented by formula (2), or a group represented by formula (4), and when Y is such a group, the imide group equivalent of component (A) can be increased. From this perspective, Y is preferably a group represented by formula (2).

[0034] In formula (2), Z is a single bond or a divalent organic group having 1 to 20 carbon atoms. Examples of divalent organic groups having 1 to 20 carbon atoms include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, ketone groups, and ester groups. In terms of reducing the polarity of component (A) and reducing the dielectric loss tangent, Z is preferably a single bond, a structure represented by formula (5), a structure represented by formula (6), or a structure represented by formula (7). Of these, a structure represented by formula (5), a structure represented by formula (6), or a structure represented by formula (7) is more preferred.

[0035]

[0036] In formula (5), R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 10 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms. Examples of such groups include an alkyl group, an alkenyl group, an aryl group, a fluoroalkyl group, a chloroalkyl group, a fluoroalkenyl group, a chloroalkenyl group, a fluoroaryl group, and a chloroaryl group.

[0037] In formula (7), t is an integer of 1 to 15, preferably an integer of 3 to 13, and more preferably an integer of 7 to 13.

[0038] Specific examples of the group represented by formula (5) include an isopropylidene group, a hexafluoroisopropylidene group, and a 1-phenylethylidene group.

[0039] An example of the group represented by formula (6) is a fluorene-9,9-diyl group.

[0040] Examples of the group represented by formula (7) include cycloalkane-1,1-diyl groups having 4 to 16 carbon atoms.

[0041] In formula (2), R １ and R ２ each independently represent a monovalent hydrocarbon group having 1 to 10 carbon atoms, some of the hydrogen atoms in the monovalent hydrocarbon group having 1 to 10 carbon atoms may be substituted with halogen atoms, and p and q each independently represent an integer of 0 to 4.

[0042] Examples of the monovalent hydrocarbon group having 1 to 10 carbon atoms and the monovalent hydrocarbon group having 1 to 10 carbon atoms in which some of the hydrogen atoms have been substituted with halogen atoms include the above-mentioned R ３ and R ４ It is similar to that explained in.

[0043] In formula (4), s is an integer of 0 or 1, and more preferably s is 1. In formulas (1), (2) and (4), * indicates a point of attachment.

[0044] Examples of tetracarboxylic acids that give the tetracarboxylic acid residue represented by formula (1) containing the structure represented by formula (2) include 4,4'-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))diphthalic acid, 4,4'-(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-(((propane- 2,2-diylbis(4,1-phenylene))bis(azanediyl)bis(carbonyl))diphthalic acid, 4,4'-((perfluoropropane-2,2-diylbis(4,1-phenylene))bis(oxy))diphthalic acid, 4,4'-(((perfluoropropane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-([1,1'-biphenyl]-4,4'-diylbis(oxy))diphthalic acid, 4,4'-(([1,1'-biphenyl]-4,4'-diylbis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-(([1,1' -biphenyl]-4,4'-diylbis(oxy))bis(carbonyl))diphthalic acid, 4,4'-(((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))diphthalic acid, 4,4'-((((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-((((9H-fluorene-9,9-diyl)bis(2-methyl- 4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((((9H-fluorene-9,9-diyl)bis(2-methyl-4,1-phenylene))bis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-((cyclodecane-1,1-diylbis(2-methyl-4,1-phenylene))bis(oxy))diphthalic acid, 4,4'-((cyclodecane-1,1-diylbis(2-methyl-4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((cyclodecane-1,1-diylbis(2-methyl-4,Examples of such phthalic acid include 4,4'-((cyclohexane-1,1-diylbis(4,1-phenylene))bis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-((cyclodecane-1,1-diylbis(4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((cyclohexane-1,1-diylbis(4,1-phenylene))bis(oxy))bis(carbonyl))diphthalic acid, and 4,4'-(((cyclohexane-1,1-diylbis(4,1-phenylene))bis(azanediyl))bis(carbonyl))diphthalic acid.

[0045] Examples of tetracarboxylic acids that give the tetracarboxylic acid residue represented by formula (1) containing a phenylene group or a naphthylene group as Y in formula (1) include 4,4'-(1,4'-phenylenebis(oxy))diphthalic acid, 4,4'-((1,4'-phenylenebis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((1,4'-phenylenebis(azanediyl))bis(carbonyl))diphthalic acid, diphthalic acid, 4,4'-(naphthalene-2,6-diylbis(oxy))diphthalic acid, 4,4'-((naphthalene-2,6-diylbis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((naphthalene-2,6-diylbis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-((naphthalene-2,7-diylbis(oxy))bis(carbonyl))diphthalic acid, and the like.

[0046] Examples of the tetracarboxylic acid residue represented by formula (1) containing the structure represented by formula (4) include 4,4'-(cyclohexane-1,4-diylbis(oxy))diphthalic acid, 4,4'-((cyclohexane-1,4-diylbis(oxy))bis(carbonyl))diphthalic acid, 4,4'-((cyclohexane-1,4-diylbis(azanediyl))bis(carbonyl))diphthalic acid, 4,4'-([1,1'-bi(cyclohexane)]-4,4'-diylbis(oxy))diphthalic acid, 4,4'-(([1,1'-bi(cyclohexane)]-4,4'-diylbis(oxy))bis(carbonyl))diphthalic acid, and 4,4'-(([1,1'-bi(cyclohexane)]-4,4'-diylbis(azanediyl))bis(carbonyl))diphthalic acid.

[0047] The component (A) may contain one or more types of structures represented by formula (1) as the tetracarboxylic acid residue.

[0048] Furthermore, component (A) may contain a structure other than the structure represented by formula (1) as the tetracarboxylic acid residue, but the structure represented by formula (1) preferably accounts for 50 mol % or more, and more preferably 80 mol % or more, when the total amount of tetracarboxylic acid residues in component (A) is taken as 100 mol %. By ensuring that the amount falls within this range, good developability and a low dielectric loss tangent can be obtained.

[0049] Examples of tetracarboxylic acids that give a structure other than the structure represented by formula (1) as the tetracarboxylic acid residue include 1,2,4,5-benzenetetracarboxylic acid (pyromellitic acid), 3,3',4,4'-biphenyltetracarboxylic acid, 2,3,3',4'-biphenyltetracarboxylic acid, 2,2',3,3'-biphenyltetracarboxylic acid, 1,2,5,6-naphthalenetetracarboxylic acid, 1,4,5,8-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 3,3',4,4'-benzophenonetetracarboxylic acid, 2,2',3,3'-benzophenonetetracarboxylic acid, bis(3,4-dicarboxyphenyl)methane, bis(2,3-dicarboxyphenyl)methane, 1,1-bis(3,4-dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, phenyl)ethane, 2,2-bis(3,4-dicarboxyphenyl)propane, 2,2-bis(2,3-dicarboxyphenyl)propane, 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, bis(3,4-dicarboxyphenyl)sulfone, bis(3,4-dicarboxyphenyl)ether, 2,3,5,6-pyridinetetracarboxylic acid, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene, 3,4,9,10-perylenetetracarboxylic acid, and aromatic rings or hydrocarbons thereof in which a portion of the hydrogen atoms has been substituted with an alkyl group or haloalkyl group having 1 to 10 carbon atoms, a halogen atom, or the like.

[0050] In the component (A), the diamine residue is not particularly limited, and known diamine residues can be used.

[0051] Examples of diamines that provide the diamine residue include aromatic diamines, aromatic diisocyanates, alicyclic diamines, alicyclic diisocyanates, aliphatic diamines, aliphatic diisocyanates, siloxane-modified diamines, siloxane-modified diisocyanates, polyether diamines, polyether diisocyanates, and bisaminophenol compounds. More specifically, 2,2'-bis(trifluoromethyl)benzidine, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 3,3'- Diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, m-phenylenediamine, p-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, 2,5-dimethylbenzene-1,4-diamine, benzidine, 3,3'-dimethylbenzidine, 2,2'-dimethylbenzidine, 3,3'-dimethoxybenzidine, 3,3'-dichlorobenzidine, 3,3'- Difluorobenzidine, o-tolidine, 4,4'-diaminoterphenyl, 1,5-diaminonaphthalene, 2,5-diaminopyridine, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 1,2-cyclohexanediamine, 1,4-cyclohexanediamine, bis(4-aminocyclohexyl)methane, 3,6-dihydroxy-1,2-cyclohexanediamine, 2,5-dihydroxy-1,4-cyclohexanediamine, bis(3-hydroxy-4-aminocyclohexyl)methane, 4,4'-bis(p-aminophenoxy)biphenyl, 2, 2'-bis[4-(p-aminophenoxy)phenyl]propane, hexahydro-4,7-methanoindanylenediamine, 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, bis(3-amino-4-hydroxyphenyl)propane, bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 3,3'-diaminodiphenyl ether, 1,3'-bis(3-aminophenoxy)benzene, bis[4-(3-aminophenoxy)phenyl]sulfone, 1,4-bis(4-aminobenzoyloxy)benzene, 4,4'-(hexafluoroisopropylidene)dianiline, 3,3'-diaminobenzophenone, 4,4'-Diaminobenzophenone, 4,4'-(hexafluoroisopropylidene)bis(2-aminophenol), 4,4'-diaminodicyclohexylmethane, 4,4'-diaminobiphenyl, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 1,3-phenylenediamine, 2,3-diaminobiphenyl, 2,2'-dimethoxy-4,4'-diaminobiphenyl, 3,3'-dimethyl-biphenyl-4,4'-diamine, 2,7-diaminofluoro ...diphenyl, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 1,3-phenylenediamine, 2, fluorene, 9,9'-bis(4-aminophenyl)fluorene, 1,4-bis(4-aminophenoxy)benzene, bis(4-aminophenoxy)biphenyl, bis(3-amino-4-hydroxyphenyl)methane, 1,1-bis(3-amino-4-hydroxyphenyl)ethane, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2-bis(3-aminophenyl)hexafluoropropane propane, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis(3-amino-4-hydroxyphenyl)ether, 1,6-hexamethylenediamine, 2,5-dihydroxy-1,6-hexamethylenediamine, 4,4'-(1,4-phenylenebisoxy)dianiline, and 4-aminophenyl 4-aminobenzoate.

[0052] The diamine residue contained in the component (A) may be one type or two or more types.

[0053] Component (A) preferably has a structure represented by formula (8) as a diamine residue in all or part of the diamine residue. That is, it is preferable that all or part of the diamine residue in component (A) has a structure represented by formula (8). By including a diamine residue represented by formula (8) in component (A), the polarity of component (A) can be reduced, and the dielectric loss tangent can also be reduced.

[0054]

[0055] (u represents an integer of 1 to 40. R ５ and R １０ R each independently represents an alkylene group having 1 to 15 carbon atoms. ６ ~R ９ each independently represents an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 10 carbon atoms. * represents a bonding site.) In formula (8), u is preferably an integer of 1 to 10. When u is 10 or less, compatibility with other monomers and solvents in the polyimide resin is increased, which is preferable in that the compound is randomly incorporated into the polyimide resin.

[0056] Examples of the structure represented by formula (8) include, but are not limited to, a dialkyltetramethyldisiloxane group and a biphenyloctamethylpentasiloxane group.

[0057] From the viewpoint of being able to further reduce the dielectric dissipation factor, when the total amount of diamine residues in the component (A) is taken as 100 mol %, the structure represented by formula (8) as the diamine residue preferably accounts for 30 mol % or more, and more preferably 40 mol % or more; and from the viewpoint of obtaining good developability, it is preferably 70 mol % or less, and more preferably 60 mol % or less.

[0058] In component (A), when the total amount of structures represented by formula (1) as tetracarboxylic acid residues is A (moles) and the total amount of structures represented by formula (8) as diamine residues is B (moles), the ratio (B / A) is preferably 0.30 or more and 1.40 or less. The value of B / A is calculated by dividing B by A and rounding off the digit to two decimal places.

[0059] Furthermore, component (A) contains multiple types of tetracarboxylic acid residues corresponding to formula (1), and in the multiple types of tetracarboxylic acid residues corresponding to formula (1), it is preferable that the group represented by Y corresponds to any one of the following structures A to F, and that at least two groups corresponding to any one of structures A to F are included. Such component (A) can increase the free volume of the molecule, thereby achieving a greater reduction in dielectric constant. Structure A: A group represented by formula (2), in which Z is a single bond. Structure B: A group represented by formula (2), in which Z has a structure represented by formula (5). Structure C: A group represented by formula (2), in which Z has a structure represented by formula (6). Structure D: A group represented by formula (2), in which Z has a structure represented by formula (7). Structure E: A phenylene group or a naphthylene group. Structure F: A group represented by formula (4).

[0060] The terminals of component (A) may be blocked with a known terminal blocking agent such as a monocarboxylic acid, an acid anhydride, a monoacid chloride, a monoamine, or a monoisocyanate. These terminal blocking agents may be used alone or in combination of two or more.

[0061] The photosensitive resin composition of the present invention may contain a resin other than component (A) as long as the object of the present invention is not impaired. Needless to say, this does not exclude cases in which the photosensitive resin composition contains a polyimide resin that does not have the structure represented by formula (1) as a tetracarboxylic acid residue.

[0062] The component (A) preferably has an imide group equivalent of 300 g / eq. or more.

[0063] The imide group equivalent refers to the mass of component (A) per mole of imide bond, and is calculated by the following formula (I).

[0064] Imido group equivalent weight=mass (g) of component (A) / number (moles) of imido groups in component (A) (I).

[0065] For example, in the case of a completely ring-closed polyimide made of two kinds of acid dianhydrides (one of which has a molecular weight Ma1 and the other has a molecular weight Ma2, and the molar fraction of the former is 70 mol % and the latter is 30 mol % relative to 100 mol of the acid dianhydride) and a diamine (whose molecular weight is Mb), the imide group equivalent can be calculated by ((0.7 × Ma1 + 0.3 × Ma2) + Mb) / 2.

[0066] By ensuring that the imide group equivalent is 300 g / eq. or more, the concentration of imide groups in component (A), which inhibit cationic polymerization, can be reduced, and the low polarity allows for a low dielectric loss tangent. There is no particular upper limit, but it is preferably 1000 g / eq. or less.

[0067] From the viewpoint of the viscosity and pattern processability of the resulting resin composition, the weight-average molecular weight of component (A) used in the photosensitive resin composition of the present invention is preferably from 1,000 to 200,000, more preferably from 3,000 to 100,000, and even more preferably from 5,000 to 50,000. The weight-average molecular weight of component (A) is measured by gel permeation chromatography (GPC) using N-methylpyrrolidone as a developing solvent, and calculated in terms of polystyrene.

[0068] The amounts of the structures and partial structures of the constituent elements, such as tetracarboxylic acid residues and diamine residues, contained in component (A) can be determined, for example, by the following method. Specifically, component (A) is dissolved in an acidic solution and analyzed using gas chromatography (GC) or nuclear magnetic resonance (NMR) to detect the structures and partial structures of the constituent elements, such as tetracarboxylic acid residues and diamine residues, and their ratios can be determined. Alternatively, the amounts can be determined by directly analyzing the photosensitive resin composition or component (A) using NMR or the like. Furthermore, when a photosensitive resin composition is prepared using a polymerization solution of component (A) without purification, the ratios of the structures and partial structures of the constituent elements, such as tetracarboxylic acid residues and diamine residues, contained in component (A) correspond to the monomer feed ratios used during polymerization of component (A), and therefore can also be calculated from the monomer feed ratios used during polymerization of component (A).

[0069] In the present invention, the component (A) can be synthesized, for example, by the following method, but is not limited to this: The polyimide resin can be obtained by heating a tetracarboxylic acid or its derivative with a diamine or its derivative, or by reacting them using an acid or a base.

[0070] In the present invention, after polymerizing component (A) by the above method, it is preferable to add it to a large amount of water or a mixture of methanol and water, precipitate it, filter it, dry it, and isolate it. The drying temperature is preferably 40 to 100°C, more preferably 50 to 80°C. This operation is preferable because it removes unreacted monomers and oligomer components such as dimers and trimers, improving the heat resistance and chemical resistance of the cured product.

[0071] Specifically, the imidization rate of the component (A) can be easily determined by the following method. Specifically, first, the infrared absorption spectrum of the component (A) or a resin composition containing the component (A) is measured, and the absorption peak of the imide structure resulting from the polyimide (1780 cm －１ Near 1377 cm －１ Next, the polymer was heat-treated at 300°C for 1 hour to obtain a sample with an imidization rate of 100%, and the infrared absorption spectrum was measured to determine the presence of a peak at 1377cm of the resin before and after the heat treatment. －１ The imidization ratio of component (A) is preferably 50% or more, and more preferably 80% or more, to obtain a polyimide having a low dielectric tangent and good mechanical properties.

[0072] Next, component (B) will be described. The cationically polymerizable compound refers to a compound containing a functional group that crosslinks by cationic polymerization, and specific examples thereof include cyclic ether compounds such as epoxy compounds and oxetane compounds, ethylenically unsaturated compounds such as vinyl ethers and styrenes, episulfide compounds, bicycloorthoesters, spiroorthocarbonates, and spiroorthoesters.

[0073] The content of component (B) in the photosensitive resin composition of the present invention is preferably 50 to 350 parts by mass, and more preferably 70 to 200 parts by mass, based on 100 parts by mass of component (A). A content of component (B) of 50 parts by mass or more based on 100 parts by mass of component (A) is preferred in that cationic polymerization properties are improved and distortion and peeling during pattern processing can be suppressed, while a content of 350 parts by mass or less is preferred in that resolution during pattern processing is improved.

[0074] As the epoxy compound as component (B), known compounds can be used, including aromatic epoxy compounds, alicyclic epoxy compounds and aliphatic epoxy compounds.

[0075] Examples of aromatic epoxy compounds include glycidyl ethers of mono- or polyhydric phenols having at least one aromatic ring (phenol, bisphenol A, phenol novolak, and alkylene oxide adducts thereof).

[0076] Examples of alicyclic epoxy compounds include compounds obtained by epoxidizing a compound having at least one cyclohexene or cyclopentene ring with an oxidizing agent (e.g., 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate).

[0077] Examples of the aliphatic epoxy compounds include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts (1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, etc.), polyglycidyl esters of aliphatic polybasic acids (diglycidyl tetrahydrophthalate, etc.), and epoxidized products of long-chain unsaturated compounds (epoxidized soybean oil, epoxidized polybutadiene, etc.).

[0078] Among these, polyfunctional epoxy compounds that are liquid at room temperature (20°C) are preferred, and the polyfunctional epoxy compounds preferably have an epoxy equivalent of 80 g / eq. or more and 500 g / eq. or less. The polyfunctional epoxy compound being liquid at room temperature is preferred in that it improves compatibility with component (A) and enables fine pattern processability to be obtained. On the other hand, the polyfunctional epoxy compound having an epoxy equivalent of 80 g / eq. or more and 500 g / eq. or less is preferred in that it improves the heat resistance and chemical resistance of the cured film.

[0079] As the oxetane compound for component (B), known compounds can be used, and specific examples thereof include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyl(3-ethyl-3-oxetanylmethyl)ether, 2-hydroxyethyl(3-ethyl-3-oxetanylmethyl)ether, 2-hydroxypropyl(3-ethyl-3-oxetanylmethyl)ether, 3-ethyl-3-{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 4,4'-bis[(3-ethyloxetan-3-yl)methoxy]biphenyl, oxetanylsilsesquioxetane, and phenol novolac oxetane. Here, an epoxy compound having an oxetanyl group corresponds to the oxetane compound. Among these, an oxetane compound containing two or more oxetanyl groups in the molecule is preferred, and the number of oxetanyl groups in one molecule is more preferably from 2 to 6. The oxetane compound containing two or more oxetanyl groups is preferred in terms of improving curability, and the oxetane compound containing six or less oxetanyl groups is preferred in terms of suppressing cracks that occur during pattern processing.

[0080] As the ethylenically unsaturated compound as component (B), known cationically polymerizable monomers can be used, including aliphatic monovinyl ethers, aromatic monovinyl ethers, polyfunctional vinyl ethers, styrenes, and cationically polymerizable nitrogen-containing monomers.

[0081] Aliphatic monovinyl ethers include methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, and cyclohexyl vinyl ether.

[0082] Examples of aromatic monovinyl ethers include 2-phenoxyethyl vinyl ether, phenyl vinyl ether, and p-methoxyphenyl vinyl ether.

[0083] Examples of polyfunctional vinyl ethers include butanediol-1,4-divinyl ether and triethylene glycol divinyl ether.

[0084] Examples of styrenes include styrene, α-methylstyrene, p-methoxystyrene, and p-tert-butoxystyrene.

[0085] Examples of the cationically polymerizable nitrogen-containing monomer include N-vinylcarbazole and N-vinylpyrrolidone.

[0086] As the episulfide compound as component (B), known compounds can be used, and specific examples include 2,2-bis[4-(2,3-epithiopropoxy)phenyl]propane and 2,2-bis[4-(2,3-epithiopropoxy)cyclohexyl]propane.

[0087] Bicyclo orthoesters include 1-phenyl-4-ethyl-2,6,7-trioxabicyclo[2.2.2]octane and 1-ethyl-4-hydroxymethyl-2,6,7-trioxabicyclo-[2.2.2]octane.

[0088] Examples of spiro orthocarbonates include 1,5,7,11-tetraoxaspiro[5.5]undecane and 3,9-dibenzyl-1,5,7,11-tetraoxaspiro[5.5]undecane.

[0089] Spiro orthoesters include 1,4,6-trioxaspiro[4.4]nonane, 2-methyl-1,4,6-trioxaspiro[4.4]nonane, and 1,4,6-trioxaspiro[4.5]decane.

[0090] From the viewpoints of improving developability and achieving a low dielectric loss tangent, it is preferred that all or part of the component (B) be either an epoxy compound or an oxetane compound, or both.

[0091] Furthermore, the epoxy compound promotes the initiation reaction of cationic polymerization, and the oxetane compound promotes the propagation reaction of cationic polymerization, thereby exhibiting good sensitivity and resolution, and also suppressing the generation of hydroxyl terminal groups due to side reactions, thereby enabling a low dielectric loss tangent. From this viewpoint, the photosensitive resin composition of the present invention preferably contains an epoxy compound and an oxetane compound as component (B), and the mass ratio R (epoxy compound content / oxetane compound content) is greater than zero and less than or equal to 1.0. From the viewpoint of more effectively achieving a low dielectric loss tangent, the mass ratio R is preferably 0.10 or greater, and more preferably 0.70 or less. The value of c / d is calculated by dividing c by d and rounding off the third decimal place to the nearest tenth.

[0092] In addition, the photosensitive resin composition of the present invention more preferably uses an oxetane compound represented by formula (9) as component (B).

[0093]

[0094] (g and h each independently represent an integer of 0 to 6, R １１ and R １２ each independently represents a monovalent organic group having 1 to 5 carbon atoms.) Examples of the oxetane compound represented by formula (9) include OXT-121 (trade names, manufactured by Toagosei Co., Ltd.) and OXBP (trade names, manufactured by UBE Co., Ltd.).

[0095] In addition, the photosensitive resin composition of the present invention more preferably uses an epoxy compound represented by formula (11) as component (B).

[0096]

[0097] (j, k, and l each independently represent an integer of 1 to 10.) The epoxy compound represented by formula (11) has high compatibility with component (A), and can therefore reduce residue after development. Specific examples of the epoxy compound represented by formula (11) include TEPIC-FL and TEPIC-VL (both trade names, manufactured by Nissan Chemical Industries, Ltd.). In TEPIC-FL, j = k = l = 4, and in TEPIC-VL, j = k = l = 1. TEPIC-FL has lower polarity than TEPIC-VL, and therefore can achieve a lower dielectric tangent.

[0098] From the viewpoint of improving sensitivity, the photosensitive resin composition of the present invention contains an oxetane compound as component (B). When the total amount of component (A) contained in the photosensitive resin composition of the present invention is taken as 100 parts by mass, the content of the oxetane compound is preferably 70 parts by mass or more, and more preferably 100 parts by mass or more. From the viewpoint of resolution, the content is preferably 200 parts by mass or less, and more preferably 150 parts by mass or less.

[0099] The photosensitive resin composition of the present invention preferably uses a compound represented by formula (12) as component (B). Use of the compound represented by formula (12) makes it possible to obtain a cured product having excellent dielectric properties without impairing pattern processability.

[0100]

[0101] (A １ represents an alkylene group having 1 to 20 carbon atoms or a divalent hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring; B １ , B ２each independently represents an ether bond or an ester bond.) In formula (12), examples of the alkylene group having 1 to 20 carbon atoms include a methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, a sec-butylene group, a tert-butylene group, an isobutylene group, a pentylene group, an isopentylene group, a tert-pentylene group, a hexylene group, a 2-hexylene group, a 3-hexylene group, a heptylene group, a 2-heptylene group, a 3-heptylene group, an isoheptylene group, a tert-heptylene group, an octylene group, an isooctylene group, a tert-octylene group, a 2-ethylhexylene group, a nonylene group, an isononylene group, a decylene group, an n-undecylene group, a 1-methyldecylene group, Examples of the alkyl group include a 4-dodecylene group, a 4-ethyloctylene group, a 1,3,5,7-tetramethyloctylene group, a tridecylene group, a 1-hexylheptylene group, an n-tetradecylene group, an n-pentadecylene group, and an n-hexadecylene group.

[0102] Examples of the divalent hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring include a cycloalkylene group and a group formed by combining a cycloalkylene group with an alkylene group. Examples of the cycloalkylene group include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, and a cyclohexylene group.

[0103] Examples of the compound represented by formula (12) include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, diglycidyl-1,2-cyclohexanedicarboxylate, and 1,2-cyclohexanedicarboxylate diglycidyl.

[0104] In formula (12), from the viewpoint of excellent resolution, B １ , B ２ is more preferably an ether bond.

[0105] In the photosensitive resin composition of the present invention, the content of the compound represented by formula (12) is preferably 10 parts by mass or more per 100 parts by mass of component (A) from the viewpoint of obtaining excellent dielectric properties, and preferably 70 parts by mass or less per 100 parts by mass of component (A) from the viewpoint of excellent pattern processability.

[0106] Next, the component (C) will be described.

[0107] The cationic polymerization initiator generates an acid when exposed to light, and causes cationic polymerization of the component (B).

[0108] Although known compounds can be used as component (C), from the viewpoints of facilitating cationic curing and preventing copper corrosion, component (C) preferably contains a sulfonium salt containing at least one counter anion selected from the group consisting of borate ions, phosphate ions, and gallate ions. Here, borate ions are complex ions having boron as the central atom, phosphate ions are complex ions having phosphorus as the central atom, and gallate ions are complex ions having gallium as the central atom.

[0109] Examples of the cation that forms the sulfonium salt include triphenylsulfonium cation, tri-p-tolyl sulfonium cation, tris(4-methoxyphenyl)sulfonium cation, 1-naphthyldiphenylsulfonium cation, 2-naphthyldiphenylsulfonium cation, tris(4-fluorophenyl)sulfonium cation, tri-1-naphthylsulfonium cation, tri-2-naphthylsulfonium cation, tris(4-hydroxyphenyl)sulfonium cation, 4-(phenylthio)phenyldiphenylsulfonium cation, 4-(p-tolylthio)phenyldi-p-tolyl sulfonium cation, 4-(4-methoxyphenylthio)phenylbis(4-methoxyphenyl)sulfonium cation, 4-(phenylthio)phenylbis(4-fluorophenyl)sulfonium cation, 4-(phenylthio)phenylbis(4-methoxyphenyl)sulfonium cation, 4-(phenylthio)phenyldi-p-tolyl sulfonium cation, [4-(4-biphenylylthio)phenyl]-4-biphenylylphenyl sulfonium cation, [4-(2-thiphenyl) oxanthonylthio)phenyl]diphenylsulfonium cation, bis[4-(diphenylsulfonio)phenyl]sulfide cation, bis[4-{bis[4-(2-hydroxyethoxy)phenyl]sulfonio}phenyl]sulfide cation, bis{4-[bis(4-fluorophenyl)sulfonio]phenyl}sulfide cation, bis{4-[bis(4-methylphenyl)sulfonio]phenyl}sulfide cation, bis{4-[bis(4-methoxyphenyl)sulfonio]phenyl}sulfide cation, 4-(4-benzoyl-2 4-(4-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium cation, 4-(4-benzoyl-2-chlorophenylthio)phenyldiphenylsulfonium cation, 4-(4-benzoylphenylthio)phenylbis(4-fluorophenyl)sulfonium cation, 4-(4-benzoylphenylthio)phenyldiphenylsulfonium cation, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium cation, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium cation,10-dihydroanthracen-2-yldiphenylsulfonium cation, 2-[(di-p-tolyl)sulfonio]thioxanthone cation, 2-[(diphenyl)sulfonio]thioxanthone cation, 4-(9-oxo-9H-thioxanthen-2-yl)thiophenyl-9-oxo-9H-thioxanthen-2-ylphenylsulfonium cation, 4-[4-(4-tert-butylbenzoyl)phenylthio]phenyldi-p-tolylsulfonium cation, 4-[4-(4-te 4-[4-(benzoylphenylthio)]phenyldiphenylsulfonium cation, 4-[4-(benzoylphenylthio)]phenyldi-p-tolylsulfonium cation, 4-[4-(benzoylphenylthio)]phenyldiphenylsulfonium cation, 5-(4-methoxyphenyl)thiaanthrenenium cation, 5-phenylthiaanthrenenium cation, 5-tolylthiaanthrenenium cation, 5-(4-ethoxyphenyl)thiaanthrenenium cation, 5-(2,4,triarylsulfonium such as (6-trimethylphenyl)thiaanthrenenium, diarylsulfonium cations such as diphenylphenacylsulfonium, diphenyl 4-nitrophenacylsulfonium cation, diphenylbenzylsulfonium cation and diphenylmethylsulfonium cation, phenylmethylbenzylsulfonium cation, 4-hydroxyphenylmethylbenzylsulfonium cation, 4-methoxyphenylmethylbenzylsulfonium cation, 4-acetocarbonyloxyphenylmethylbenzylsulfonium cation, 4-hydroxyphenyl(2-naphthylmethyl)methylsulfonium cation, 2-naphthylmethylbenzylsulfonium cation, 2-naphthylmethyl(1-ethoxycarbonyl)ethylsulfonium Examples of the sulfonium cation include, but are not limited to, monoaryl sulfonium cations such as phenacyl thiophenium, phenylmethylphenacylsulfonium, 4-hydroxyphenylmethylphenacylsulfonium cation, 4-methoxyphenylmethylphenacylsulfonium cation, 4-acetocarbonyloxyphenylmethylphenacylsulfonium cation, 2-naphthylmethylphenacylsulfonium, 2-naphthyloctadecylphenacylsulfonium cation, and 9-anthracenylmethylphenacylsulfonium, dimethylphenacylsulfonium cation, phenacyltetrahydrothiophenium cation, dimethylbenzylsulfonium cation, benzyltetrahydrothiophenium cation, and octadecylmethylphenacylsulfonium cation.

[0110] Examples of borate ions include, but are not limited to, pentafluorophenylborate ions, trifluorophenylborate ions, tetrafluorophenylborate ions, trifluoromethylphenylborate ions, bis(trifluoromethyl)phenylborate ions, pentafluoroethylphenylborate ions, bis(pentafluoroethyl)phenylborate ions, fluoro-bis(trifluoromethyl)phenylborate ions, fluoro-pentafluoroethylphenylborate ions, and fluoro-bis(pentafluoroethyl)phenylborate ions.

[0111] Examples of phosphate ions include, but are not limited to, hexafluorophosphate ion and tris(pentafluoroethyl)trifluorophosphate ion.

[0112] Examples of gallate ions include, but are not limited to, tetrakis(pentafluorophenyl)gallate ion and tetrakis[3,5-bis(trifluoromethyl)phenyl]gallate ion.

[0113] In the photosensitive resin composition of the present invention, the content of the component (C) is preferably 0.3 parts by mass or more and 10 parts by mass or less, and more preferably 0.5 parts by mass or more and 8 parts by mass or less, per 100 parts by mass of the component (B), from the viewpoint of sufficiently cationic polymerization of the component (B) and obtaining a good pattern shape.

[0114] The photosensitive resin composition of the present invention may contain a known sensitizer. The sensitizer is a compound that absorbs light, provides the absorbed light energy to component (C), and assists the action of component (C). Furthermore, the sensitizer absorbs light at the wavelength of irradiation used in pattern processing, and can therefore reduce the transmittance of a photosensitive resin composition film formed from the photosensitive resin composition. Therefore, the transmittance of the photosensitive resin composition film can be controlled as desired by adjusting the content of the sensitizer in the photosensitive resin composition.

[0115] The photosensitive resin composition of the present invention may contain a silane compound. By including a silane compound, the adhesion between the cured product and the substrate is improved. The content of the silane compound is preferably 0.01 to 10 parts by mass, where the total amount of component (A) is 100 parts by mass. Here, a silane compound having a cationically polymerizable group is considered to be a compound corresponding to component (B). Specific examples of silane compounds containing a cationically polymerizable group include KBM-303 and KBM-403 (both product names, manufactured by Shin-Etsu Chemical Co., Ltd.). Among silane compounds, adhesion improvers having a triazine ring are also preferred in terms of improving the adhesion between the cured product and the substrate, and examples thereof include KBM-9659 (product name, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0116] The photosensitive resin composition of the present invention may contain a thermal crosslinking agent that crosslinks by heat. By including a thermal crosslinking agent, the heat resistance of the cured film can be further improved. There are no limitations on the thermal crosslinking agent as long as it crosslinks by heat. In the present invention, component (B) is not considered to be a thermal crosslinking agent.

[0117] The photosensitive resin composition of the present invention may further contain an antioxidant or a surfactant, and may also contain inorganic particles such as silicon dioxide or titanium dioxide, or polyimide powder for the purposes of suppressing the thermal expansion coefficient or lowering the dielectric constant.

[0118] The cured product of the present invention is a cured product obtained by curing the photosensitive resin composition of the present invention. The cured product of the present invention may be a cured product in any manner as long as the photosensitive resin composition is cured by light or heat.

[0119] The method of curing with light or heat is specifically 50 mJ / cm using the 365 nm i-line, 405 nm h-line, and 436 nm g-line of a high-pressure mercury lamp. ２ More than 3000mJ / cm ２ Examples of known methods include a method of curing by exposure to light and a method of curing by heat treatment at 150° C. or higher and 500° C. or lower for 5 minutes or longer and 5 hours or shorter.

[0120] A method for producing a cured product of the present invention will be described. The method for producing a cured product of the present invention includes the steps of applying the photosensitive resin composition of the present invention onto a substrate and drying it to form a photosensitive resin composition film, exposing the photosensitive resin composition film to light, developing the exposed photosensitive resin composition film, and curing the developed photosensitive resin composition film.

[0121] The process of applying the photosensitive resin composition of the present invention to a substrate and drying to form a photosensitive resin composition film includes, but is not limited to, first applying the photosensitive resin composition of the present invention to a substrate using a spin coater, spray coater, screen coater, blade coater, die coater, calendar coater, meniscus coater, bar coater, roll coater, comma roll coater, gravure coater, slit die coater, etc., and then drying at a temperature in the range of 50° C. to 150° C. for 1 minute to several hours to form a photosensitive resin composition film. Examples of the substrate include, but are not limited to, silicon wafers, ceramics, gallium arsenide, organic circuit boards, inorganic circuit boards, and these substrates on which circuit components are arranged.

[0122] The step of exposing the photosensitive resin composition film may be carried out, for example, by exposing the film to 365 nm i-line, 405 nm h-line, and 436 nm g-line of a high-pressure mercury lamp at 50 mJ / cm through a mask having a desired pattern. ２ Above, 3000mJ / cm ２ Examples of suitable exposure temperatures include, but are not limited to, the following: The photosensitive resin film exposed in the above step may be subjected to post-exposure baking. The post-exposure baking is preferably performed at 50° C. or higher from the viewpoints of curability and adhesion to the substrate, and preferably at 150° C. or lower from the viewpoint of resolution.

[0123] Examples of processes for developing the photosensitive resin film after exposure include, but are not limited to, spraying a developer onto the photosensitive resin film surface, puddling the developer on the film surface, immersing the film in the developer, or immersing the film in the developer and applying ultrasonic waves. The development conditions, such as the development time and the temperature of the developer in the development step, may be any conditions that allow the exposed area to be removed and a pattern to be formed. The developer used for development is preferably a good solvent for the photosensitive resin composition, or a combination of the good solvent and a poor solvent. Specifically, preferred good solvents include N-methylpyrrolidone, N,N-dimethylacetamide, cyclopentanone, cyclohexanone, γ-butyrolactone, and propylene glycol methyl ether acetate. Preferred poor solvents include toluene, xylene, ethanol, isopropyl alcohol, ethyl lactate, propylene glycol methyl ether acetate, and water. When using a mixture of a good solvent and a poor solvent, it is preferable to adjust the ratio of the poor solvent to the good solvent depending on the solubility of the polymer in the photosensitive resin composition. Furthermore, two or more kinds of each solvent can be used in combination.

[0124] Furthermore, when the photosensitive resin composition is soluble in an alkaline aqueous solution, alkaline aqueous development may be performed. The developer used for development dissolves and removes the alkaline aqueous solution-soluble polymer, and is typically an alkaline aqueous solution containing an alkaline compound dissolved therein. Examples of alkaline compounds include tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate. Furthermore, these alkaline aqueous solutions may be used alone or in combination with water-soluble organic solvents such as polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and γ-butyrolactone; alcohols such as methanol, ethanol, and isopropanol; esters such as ethyl lactate and propylene glycol monomethyl ether acetate; and ketones such as cyclopentanone, cyclohexanone, and isobutyl ketone.

[0125] After development, it is preferable to perform a rinse treatment with an organic solvent or water. When an organic solvent is used, in addition to the organic solvents described above in the description of the developer, for example, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and isopropyl alcohol can be used. When water is used as a rinse solution, a water-soluble organic solvent such as alcohols such as ethanol and isopropyl alcohol, or esters such as ethyl lactate and propylene glycol monomethyl ether acetate can be added to water to perform the rinse treatment.

[0126] The process of curing the photosensitive resin composition film after development includes, but is not limited to, a process of heating the film at a temperature in the range of 150°C to 500°C for 5 minutes to 5 hours to allow a thermal crosslinking reaction to proceed, thereby forming a cured product. The heating process can be performed by selecting a temperature and gradually increasing the temperature, or by selecting a temperature range and continuously increasing the temperature. Specific examples of the former include, but are not limited to, a method of performing heat treatment at 130°C and 200°C for 30 minutes each. Examples of the latter include, but are not limited to, a method of linearly increasing the temperature from room temperature to 400°C over 2 hours.

[0127] The cured product formed from the photosensitive resin composition of the present invention can be used as an insulating film or a protective film that constitutes an electronic component.

[0128] The electronic component of the present invention is an electronic component comprising the cured product of the present invention.

[0129] Here, examples of electronic components include active components having semiconductors such as transistors and diodes, and passive components such as resistors, capacitors, inductors, etc. Furthermore, a device made up of electronic components using semiconductors is called a semiconductor device.

[0130] Specific examples of the cured product used in electronic components include, but are not limited to, semiconductor passivation films, surface protective films for semiconductor elements, TFTs (Thin Film Transistors), and other interlayer insulating films such as interlayer insulating films between rewirings in multilayer wiring for high-density packaging of 2 to 10 layers, insulating films and protective films for touch panel displays, and insulating layers for organic electroluminescent devices. The semiconductor element is an element containing a semiconductor, and examples thereof include integrated circuits (ICs), memories, and the like.

[0131] Among the electronic components of the present invention, specific examples of semiconductor devices include chip-first fan-out wafer-level packages and chip-first fan-out panel-level packages. A chip-first fan-out wafer-level package or chip-first fan-out panel-level package is a semiconductor package in which an extension section is provided around a semiconductor chip using an encapsulating resin such as epoxy resin, rewiring is performed from electrodes on the semiconductor chip to the extension section, and solder balls are also mounted on the extension section to ensure the required number of terminals. In a chip-first fan-out wafer-level package or chip-first fan-out panel-level package, wiring is installed so as to straddle the boundary formed by the main surface of the semiconductor chip and the main surface of the encapsulating resin, and a cured product is arranged as an insulating film between the wiring.

[0132] The electronic component of the present invention preferably comprises the cured product of the present invention disposed as an insulating film between wirings, i.e., the electronic component of the present invention preferably takes the form of a chip-first fan-out wafer-level package or a chip-first fan-out panel-level package.

[0133] As an example of the method for manufacturing electronic components of the present invention, a method for manufacturing a semiconductor device using a redistribution layer (RDL) first process is shown. A barrier metal such as titanium is formed on a support substrate such as a glass substrate or a silicon wafer by sputtering, and a copper seed (seed layer) is then formed on top of that by sputtering. After that, copper electrode pads are formed by a process that includes resist processing, electrolytic plating, resist stripping, and seed layer etching (the process from seed layer formation to etching is called the semi-additive process (SAP)). Next, the photosensitive resin composition of the present invention is applied to the entire surface of the support substrate on which the electrode pads have been formed, and dried to form a photosensitive resin film. Lines and spaces, square, or hole patterns are formed in the resulting photosensitive resin film as needed. A heat treatment is then performed to form a cured layer. This layer becomes an insulating film. Next, copper metal wiring (redistribution) is formed again by the SAP process. Subsequently, the insulating film and SAP processes are repeated to form a multilayer wiring structure. Next, the photosensitive resin composition of the present invention is again applied and patterned, followed by heat treatment and curing to form an insulating film. Then, copper posts (Cu posts) are formed on the metal wiring in the openings of the insulating film using the SAP method. The pitch of the Cu posts and the pitch of the conductive portions of the semiconductor chip are made equal. That is, the pitch of the conductive portions of the semiconductor chip is finer than the pitch of the electrode pads, and each rewiring layer constituting the multilayer wiring structure gradually becomes finer from the electrode pads to the Cu posts, thereby multiplying the wiring. In the multilayer wiring structure, the thickness of adjacent insulating films also becomes the same or thinner as they approach the semiconductor chip. Next, the semiconductor chip is connected to the Cu posts via solder bumps. This electrically connects the electrode pads and the semiconductor chip via the metal wiring and solder bumps. The semiconductor chip is then encapsulated with an encapsulating resin to form a semiconductor package, and the support substrate and the rewiring layer are peeled off to separate the semiconductor package. In this way, a semiconductor device having a multilayer wiring structure using the RDL first process can be obtained.

[0134] The cured product of the present invention has a low dielectric constant and dielectric dissipation factor, and therefore can suppress transmission loss and improve antenna characteristics. Therefore, the electronic component of the present invention is an electronic component including a semiconductor package having at least a semiconductor element, a rewiring layer, a sealing resin, a ground terminal, and an antenna wiring, and it is preferable that the insulating layer of the rewiring layer or the sealing resin includes the cured product of the present invention, and that the sealing resin is located between the ground terminal and the antenna wiring.

[0135] As an example of such an electronic component, a semiconductor package including an IC chip (semiconductor element), a rewiring layer, a sealing resin, and an antenna wiring will be described with reference to FIG. 1 . FIG. 1 is a schematic cross-sectional view of a semiconductor package including an IC chip (semiconductor element), a rewiring layer, a sealing resin, and an antenna element. A rewiring layer (two copper layers, three insulating layers) made of copper wiring 109 and an insulating film 110 formed using the cured product of the present invention is formed on an electrode pad 102 of an IC chip 101. A barrier metal 112 and a solder bump 113 are formed on the pad of the rewiring layer 111 (copper wiring 109 and insulating film 110). To seal the IC chip, a first sealing resin 108 made of the cured product of the present invention is formed, and a copper wiring 109 serving as a ground for the antenna is further formed thereon. A first via wiring 107 is formed through a via hole formed in the first sealing resin 108, connecting a ground terminal 106 to the rewiring layer 111 (copper wiring 109 and insulating film 110). A second sealing resin 105 made of the cured product of the present invention is formed on the first sealing resin 108 and the ground terminal 106, and a planar antenna wiring 104 is formed thereon. A second via wiring 103 is formed through a via hole formed in the first sealing resin 108 and the second sealing resin 105, connecting the planar antenna wiring 104 to the rewiring layer 111 (copper wiring 109 and insulating film 110). The thickness of each insulating film 110 is preferably 10 to 20 μm, and the thicknesses of the first sealing resin and the second sealing resin are preferably 50 to 200 μm and 100 to 400 μm, respectively. Because the cured product of the present invention shows little deterioration after a reliability test, a semiconductor package including the resulting antenna element can be obtained that is highly reliable and free from cracks.

[0136] The present invention will be described below with reference to examples, but the present invention should not be construed as being limited to these examples.

[0137] [Evaluation Methods] (1) Weight-Average Molecular Weight and Dispersity The weight-average molecular weight (Mw) of the resin was confirmed using a GPC (gel permeation chromatography) device, Waters 2690-996 (manufactured by Nippon Waters Co., Ltd.). Measurement was performed using N-methyl-2-pyrrolidone (hereinafter referred to as NMP) as the developing solvent, and the weight-average molecular weight (Mw) and dispersity (PDI = Mw / Mn) were calculated in terms of polystyrene.

[0138] (2) Pattern Processability (2)-1 Developability and Sensitivity The varnish was spin-coated onto a silicon wafer using a spin coater (1H-360S manufactured by Mikasa Co., Ltd.), and then pre-baked for 3 minutes at 120°C using a hot plate (SCW-636 manufactured by Dainippon Screen Mfg. Co., Ltd.) to produce a pre-baked film with a film thickness of 10 μm. The obtained pre-baked film was exposed to light using a parallel light mask aligner (hereinafter referred to as PLA) (PLA-501F manufactured by Canon Inc.) and an ultra-high pressure mercury lamp as a light source (a mixed line of g-line, h-line, and i-line) through a mask having a line width of 50 μm, a line width of 40 μm, a line width of 30 μm, a line width of 20 μm, a line width of 15 μm, a line width of 10 μm, and a line width of 5 μm. The exposure dose for each sample was 300 mJ / cm. ２ , 500 mJ / cm ２ , 700 mJ / cm ２ , 1000mJ / cm ２ , 1500mJ / cm ２ and 2000 mJ / cm ２ The exposure amount was calculated by measuring the illuminance of i-line (365 nm).

[0139] The exposed prebaked film was then post-exposure baked at 120°C for 3 minutes, developed by immersion in propylene glycol monomethyl ether acetate (PGMEA) as a developer, and then rinsed in isopropyl alcohol (IPA) for 40 seconds. The immersion time in the developer was determined in advance as (BP) seconds, the time until the unexposed areas dissolved and the substrate was exposed, and was set to (BP x 1.5) seconds. However, the development time was limited to 200 seconds. If the unexposed areas did not expose the substrate even after immersion in the developer for 200 seconds, or if the line-and-space pattern disappeared due to dissolution when developed for (BP x 1.5) seconds, it was determined that pattern processing was not possible.

[0140] The evaluation was based on the minimum exposure dose at which a pattern with a line width of 50 μm was opened after development and rinsing. The minimum exposure dose at which a pattern with a line width of 50 μm was opened was taken as the sensitivity and rated on a scale of A to E as shown in Table 1 below.

[0141] The film thickness was measured using a Lambda Ace STM-602 manufactured by Dai-Nippon Screen Mfg. Co., Ltd., with the refractive index of the object being measured set to 1.629. Film thicknesses described below were also determined in the same manner.

[0142]

[0143] (2)-2 Resolution In the evaluation of (2)-1 above, at the exposure dose used as the sensitivity, a pattern with the smallest opening line width was determined as designed, i.e., according to the mask dimensions. The resolution (the line width of the pattern with the smallest opening line width) was evaluated on a five-level scale, A to E, as shown in Table 2 below.

[0144]

[0145] (3) Measurement of Dielectric Constant and Dielectric Loss Tangent The varnish was applied to a 6-inch silicon wafer by spin coating using a coating and developing apparatus Mark-7 manufactured by Tokyo Electron Ltd., and prebaked at 120°C for 3 minutes so that the film thickness after prebaking was 11 μm. Then, PLA was applied to the entire surface at 1500 mJ / cm ２The sample was exposed to an exposure dose of 1000 ppm, and then heated at 200°C for 1 hour using an inert oven CLH-21CD-S (manufactured by Koyo Thermo Systems Co., Ltd.) at an oxygen concentration of 20 ppm by volume or less, with the temperature increased from 50°C to 200°C at a rate of 3.5°C / min. After the treatment, the sample was cooled, and when the temperature reached 50°C or less, the silicon wafer was removed and immersed in 45% by mass hydrofluoric acid for 1 minute to peel the cured resin film from the silicon wafer. This film was cut into strips measuring 3 cm wide and 10 cm long, and the dielectric constant and dielectric loss tangent of the cured resin film at a frequency of 1 GHz were measured using a perturbation cavity resonator method in accordance with ASTM D2520 at room temperature of 23.0°C and humidity of 45.0% RH. The dielectric properties were evaluated on a five-point scale (A to E) as shown in Table 3 below.

[0146]

[0147] Abbreviations of compounds used in the synthesis examples and examples are listed below. BSAA: 4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic)dianhydride TBIS-DMPN: cyclodecane-1,3-diylbis(2-methyl-4,1-phenylene)bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylate) BPF-PA: 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride 26DHN-TME: naphthalene-2,6-diyl bis(1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylate) 6HBP-TME: 1,1'-bicyclohexane-4,4'-diyl bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylate) BP-TME: biphenyl-4,4'-diyl bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylate) TMBPA: 1,3-dihydro-1,3-dioxo-5,5'-isobenzofurancarboxylic acid (1-methylethylidene)di-4,1-phenylene ester TBIS-MPN: 5,5'-[(9H-fluoren-9-ylidenebis(2-methyl-4,1-phenylene)]bis(1,3-dioxo-1,3-dihydro-5-isobenzofurancarboxylate) 6F-BPADA: 1,1,1,3,3,3-hexafluoro-2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propanoic dianhydride ODPA: 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride TDA-100: 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic dianhydride PDA: Phenylenediamine TFMB: 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl SiDA: 1,3-Bis(3-aminopropyl)tetramethyldisiloxane TEPIC-VL: isocyanuric acid-modified epoxy compound (manufactured by Nissan Chemical Industries, Ltd.) TEPIC-FL: isocyanuric acid-modified epoxy compound (manufactured by Nissan Chemical Industries, Ltd.) YL-980: bisphenol A-type epoxy resin (trade name "YL-980", manufactured by Mitsubishi Chemical Corporation) PETG: epoxy compound containing a quaternary carbon (trade name "PETG", manufactured by Resonac Inc.) OXBP: oxetane compound corresponding to the structure of formula (9) (trade name "OXBP", manufactured by Ube Industries, Ltd.) OXT-221: oxetane compound corresponding to the structure of formula (9) (trade name "OXT-221", manufactured by Toagosei Co., Ltd.) OXT-121: oxetane compound corresponding to the structure of formula (9) (trade name "OXT-121", manufactured by Toagosei Co., Ltd.) OXT-191: oxetanyl silicate (trade name "OXT-191", manufactured by Toagosei Co., Ltd.) EPOX MK R540: compound corresponding to the structure of formula (12) (trade name, manufactured by Blintec Co., Ltd.) EX-212L: compound corresponding to the structure of formula (12) (trade name, manufactured by Nagase ChemteX Corporation) CPI-310FG: sulfonium salt containing gallate ions (trade name "CPI-310FG", manufactured by San-Apro Co., Ltd.) GBL: γ-butyrolactone The compounds used in each example and comparative example were synthesized by the following methods.

[0148] Synthesis Example 1 Synthesis of Polyimide Resin (A-1) Under a dry nitrogen stream, 50.84 g (0.100 mol) of 26DHN-TME and 100 g of GBL were added to a three-necked flask and dissolved with stirring at 60° C. Subsequently, 10.81 g (0.100 mol) of PDA was added and stirred at 60° C. for 1 hour, and then the temperature was raised to 200° C. and stirred for 4 hours. The reaction solution was allowed to cool, yielding a GBL solution of polyimide resin (A-1).

[0149] Synthesis Example 2 Synthesis of Polyimide Resin (A-2) Under a dry nitrogen stream, 50.84 g (0.100 mol) of 26DHN-TME and 100 g of GBL were added to a three-necked flask and dissolved with stirring at 60°C. Subsequently, 32.02 g (0.100 mol) of TFMB was added, and the mixture was stirred at 60°C for 1 hour, and then heated to 200°C and stirred for 4 hours. The reaction solution was allowed to cool, yielding a GBL solution of polyimide resin (A-2).

[0150] Synthesis Examples 3 to 10 Synthesis of Polyimide Resin (A-3) to Polyimide Resin (A-10) Using the raw materials shown in Table 4 below and in the compositions shown in Table 4, reactions were carried out in the same manner as in Synthesis Example 2 to obtain GBL solutions of polyimide resin (A-3) to polyimide resin (A-10).

[0151] Synthesis Example 11 Synthesis of Polyimide Resin (A-11) Under a dry nitrogen stream, 52.05 g (0.100 mol) of BSAA and 100 g of GBL were added to a three-necked flask and stirred to dissolve at 60°C. Subsequently, 24.02 g (0.075 mol) of TFMB and 6.21 g (0.025 mol) of SiDA were added and stirred at 60°C for 1 hour, and then the temperature was raised to 200°C and stirred for 4 hours. The reaction solution was allowed to cool, yielding a GBL solution of polyimide resin (A-11).

[0152] Synthesis Example 12 Synthesis of Polyimide Resin (A-12) Under a dry nitrogen stream, 26.02 g (0.050 mol) of BSAA, 15.5 g (0.050 mol) of ODPA, and 100 g of GBL were added to a three-necked flask and stirred to dissolve at 60°C. Subsequently, 8.0 g (0.025 mol) of TFMB and 18.63 g (0.075 mol) of SiDA were added and stirred at 60°C for 1 hour, and then the temperature was raised to 200°C and stirred for 4 hours. The reaction solution was allowed to cool, yielding a GBL solution of polyimide resin (A-12). The raw material composition of polyimide resin (A-12) is shown in Table 4.

[0153] Synthesis Examples 13 to 16 Synthesis of Polyimide Resin (A-13) to Polyimide Resin (A-16) Polyimide resin (A-13) to polyimide resin (A-16) were synthesized using the raw materials shown in Table 4 below and in the compositions shown in Table 4, in the same manner as in Synthesis Example 11, by reacting.

[0154] Synthesis Examples 17 to 19 Synthesis of Polyimide Resin (A-17) to Polyimide Resin (A-19) Using the raw materials shown in Table 4 below and in the compositions shown in Table 4, a reaction was carried out in the same manner as in Synthesis Example 12 to obtain GBL solutions of polyimide resin (A-17) to polyimide resin (A-19).

[0155] Synthesis Example 20 Synthesis of Polyimide Resin (A-22) Under a dry nitrogen stream, 26.02 g (0.050 mol) of BSAA, 32.13 g (0.050 mol) of BPF-PA, and 100 g of GBL were added to a three-necked flask and stirred to dissolve at 60°C. Subsequently, 16.01 g (0.050 mol) of TFMB and 12.43 g (0.050 mol) of SiDA were added and stirred at 60°C for 1 hour, and then the temperature was raised to 200°C and stirred for 4 hours. The reaction solution was allowed to cool, yielding a GBL solution of polyimide resin (A-22). The raw material composition of polyimide resin (A-22) is shown in Table 4.

[0156] Synthesis Examples 21 and 22 Synthesis of Polyimide Resin (A-20) to Polyimide Resin (A-21) Using the raw materials shown in Table 4 below and in the compositions shown in Table 4, a reaction was carried out in the same manner as in Synthesis Example 2 to obtain GBL solutions of polyimide resin (A-20) to polyimide resin (A-21).

[0157] The raw material compositions of the polyimide resins obtained in Synthesis Examples 1 to 22 and various properties of the resins such as weight average molecular weight and PDI are shown in Table 4.

[0158]

[0159] *1: A: Total amount (moles) of the structure represented by formula (1) as tetracarboxylic acid residues contained in the polyimide. B: Total amount (moles) of the structure represented by formula (8) as diamine residues contained in the polyimide.

[0160] Example 1 A small amount of a GBL solution of polyimide resin (A-1) was taken as a polyimide resin and placed in an aluminum cup of known mass. The total mass was measured, and the value obtained by subtracting the mass of the aluminum cup was designated W1 (g). Subsequently, the solution was heated at 250°C for 1 hour to remove the solvent, and the total mass was measured. The value obtained by subtracting the mass of the aluminum cup was designated W2 (g). Using the solid content concentration (mass%) calculated by (W2 / W1 x 100), GBL was added to the GBL solution of polyimide resin (A-1) so that the concentration of polyimide resin (A-1) was adjusted to 40 mass%, thereby obtaining a 40 mass% GBL solution of polyimide resin (A-1) (this solution is referred to as "solution (A)").

[0161] Next, under yellow light, 50.0 g of solution (A), 20.0 g of TEPIC-VL as component (B), and 1.0 g of CPI-310FG and 20.0 g of GBL as component (C) were mixed, and the mixture was pressure-filtered using a filter with a retention particle size of 1 μm to obtain a photosensitive resin composition. The sensitivity, resolution, dielectric constant, and dielectric loss tangent of the photosensitive resin composition were evaluated according to the evaluation methods (2) and (3) above. The evaluation results are shown in Table 6.

[0162] Examples 2 to 44, Comparative Examples 1 and 2 A 40% by mass GBL solution of a polyimide resin was prepared in the same manner as in Example 1, except that the polyimide resins shown in Table 5 were used.

[0163] Photosensitive resin compositions were prepared in the same manner as in Example 1, except that the 40% by mass GBL solution of the polyimide resin, component (B), component (C), and other components were mixed in the compositions shown in Table 5. The sensitivity, resolution, dielectric constant, and dielectric loss tangent of the photosensitive resin compositions were evaluated according to the evaluation methods (2) and (3) above. The evaluation results are shown in Table 6.

[0164]

[0165] *2: 40 mass% GBL solution of component (A). *3: Mass ratio of epoxy compound to oxetane compound in component (B) (epoxy compound content / oxetane compound content). *4: Mass ratio of oxetane compound in component (B) to component (A) (oxetane compound content / component (A) content).

[0166]

[0167] REFERENCE SIGNS LIST 101 IC chip 102 Electrode pad 103 Second via wiring 104 Planar antenna wiring 105 Second sealing resin 106 Ground 107 First via wiring 108 First sealing resin 109 Copper wiring 110 Insulating film 111 Rewiring layer 112 Barrier metal 113 Solder bump

Claims

1. A photosensitive resin composition containing a polyimide resin (hereinafter referred to as "component (A)"), a cationically polymerizable compound (hereinafter referred to as "component (B)"), and a cationic polymerization initiator, characterized in that component (A) has a structure represented by formula (1) as a tetracarboxylic acid residue in all or part of the tetracarboxylic acid residue. (Each X independently represents a single bond or a divalent linking group (having a total carbon number of 10 or less). Y represents a phenylene group, a naphthylene group, a group represented by formula (2), or a group represented by formula (4). * indicates the point of attachment to the amide group, carboxyl group, or carbonyl group of the imide ring.) (In formula (2) and formula (4), R １ and R ２ each independently represents a monovalent hydrocarbon group having 1 to 10 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms; Z represents a single bond or a divalent organic group having 1 to 20 carbon atoms; p and q each independently represent an integer of 0 to 4; and s represents an integer of 0 or 1. * indicates the point of attachment to X.

2. The photosensitive resin composition according to claim 1, wherein the imide group equivalent of component (A) is 300 g / eq. or more.

3. The photosensitive resin composition according to claim 1 or 2, wherein Z in formula (2) is a single bond, a structure represented by formula (5), a structure represented by formula (6), or a structure represented by formula (7). (In formulas (5) to (7), R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 9 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms, and t is an integer of 1 to 15. * indicates the point of attachment to the benzene ring.

4. The photosensitive resin composition according to claim 1 or 2, wherein X in formula (1) is —O—.

5. The photosensitive resin composition according to claim 1 or 2, wherein component (A) has a structure represented by formula (8) as a diamine residue in all or part of the diamine residue. (u represents an integer of 1 to 40. R ５ and R １０ R each independently represents an alkylene group having 1 to 15 carbon atoms. ６ ~R ９ each independently represents an alkyl group having 1 to 15 carbon atoms or an aryl group having 6 to 10 carbon atoms. * represents the point of attachment to the nitrogen atom.

6. The photosensitive resin composition according to claim 5, wherein in component (A), when the total amount of structures represented by formula (1) as tetracarboxylic acid residues is A (moles) and the total amount of structures represented by formula (8) as diamine residues is B (moles), the ratio (B / A) is 0.3 or more and 1.4 or less.

7. The photosensitive resin composition according to claim 1 or 2, wherein component (A) contains multiple types of tetracarboxylic acid residues corresponding to formula (1), and in the multiple types of tetracarboxylic acid residues corresponding to formula (1), the group represented by Y corresponds to any one of the following structures A to F, and at least two groups corresponding to any one of structures A to F are contained. Structure A: A group represented by formula (2), in which Z is a single bond. Structure B: A group represented by formula (2), in which Z is a group having a structure represented by the following formula (5). Structure C: A group represented by formula (2), in which Z is a group having a structure represented by the following formula (6). Structure D: A group represented by formula (2), in which Z is a group having a structure represented by the following formula (7). Structure E: a phenylene group or a naphthylene group. Structure F: a group represented by formula (4). (In formulas (5) to (7), R ３ and R ４ each independently represents a monovalent hydrocarbon group having 1 to 9 carbon atoms in which some of the hydrogen atoms may be substituted with halogen atoms, t is an integer of 1 to 15, and * represents the point of attachment to the benzene ring.

8. The photosensitive resin composition according to claim 1 or 2, wherein all or part of component (B) is either an epoxy compound or an oxetane compound, or both.

9. A photosensitive resin composition according to claim 1 or 2, comprising an epoxy compound and an oxetane compound as component (B), the mass ratio of which (epoxy compound content / oxetane compound content) is greater than zero and less than or equal to 1.

10. The photosensitive resin composition according to claim 1 or 2, which contains an oxetane compound as component (B), and the content of the oxetane compound is 70 to 200 parts by mass per 100 parts by mass of component (A).

11. The photosensitive resin composition according to claim 1 or 2, wherein all or part of component (B) is a compound represented by formula (12). (A １ represents an alkylene group having 1 to 20 carbon atoms or a divalent hydrocarbon group having 3 to 20 carbon atoms and an aliphatic hydrocarbon ring; B １ and B ２ each independently represents an ether bond or an ester bond.

12. A cured product obtained by curing the photosensitive resin composition according to claim 1 or 2.

13. A method for producing a cured product using the photosensitive resin composition according to claim 1 or 2, comprising the steps of: applying the photosensitive resin composition onto a substrate and drying it to form a photosensitive resin composition film; exposing the photosensitive resin composition film to light; developing the photosensitive resin composition film after exposure; and curing the photosensitive resin composition film after development.

14. An electronic component comprising the cured product according to claim 12.

15. An electronic component in which the cured product according to claim 12 is disposed as an insulating film between wirings.

16. An electronic component including a semiconductor package having a semiconductor element, a rewiring layer, a ground terminal, an antenna wiring, and a sealing resin disposed between the ground terminal and the antenna wiring, wherein the insulating layer of the rewiring layer or the sealing resin contains the cured product described in claim 12.

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