Photosensitive resin composition, method for producing pattern cured product, cured product, interlayer insulating film, coating coating layer, surface

Abstract

The invention provides a photosensitive resin composition, a method for producing a pattern cured product, a cured product, an interlayer insulating film, a cover coat, a surface protective film, and an electronic component. This photosensitive resin composition contains (A) a polyimide precursor having a polymerizable unsaturated bond, (B) a polymerizable monomer, (C) a photopolymerization initiator, (D) a cyclization catalyst, and (E) a solvent.

Description

[0001] This application is a divisional application of application number 201980065227.5 (international application number PCT / JP2019 / 038959), filed on October 2, 2019, entitled “Photosensitive resin composition, method for manufacturing pattern-cured product, cured product, interlayer insulating film, cover coat, surface protective film, and electronic component”. TECHNICAL FIELD

[0002] The present application relates to a photosensitive resin composition, a method for manufacturing a pattern-cured product, a cured product, an interlayer insulating film, a cover coat, a surface protective film, and an electronic component. BACKGROUND

[0003] In the past, a surface protective film and an interlayer insulating film of a semiconductor element have used a polyimide, a polybenzoxazole, or the like that has excellent heat resistance and electrical properties, mechanical properties, and the like. In recent years, a photosensitive resin composition that imparts a photosensitive property to these resins themselves has been used, and if this photosensitive resin composition is used, it is possible to simplify the manufacturing process of a pattern-cured product and shorten a complicated manufacturing process (for example, refer to Patent Literature 1).

[0004] In addition, in recent years, the miniaturization of transistors that support the high performance of computers has approached the limit of the proportional law, and in order to further increase the performance and speed, a stacked device structure in which semiconductor elements are stacked in three dimensions has attracted attention.

[0005] In the stacked device structure, a multi-die fanout wafer level packaging (Multi-die Fanout Wafer Level Packaging) is a packaging in which a plurality of chips are sealed together in one package, and compared to a fanout wafer level packaging (manufactured by sealing one chip in one package) proposed in the past, it is possible to expect cost reduction and performance improvement, and thus is attracting attention.

[0006] In the production of a multi-die fanout wafer level packaging, from the viewpoint of protecting high-performance chips, protecting low-heat-resistant sealing materials, and improving yield, there is a strong demand for low-temperature curability (for example, refer to Patent Literature 2).

[0007] In addition, as a resin composition, a resin composition containing a polyimide precursor has been disclosed (for example, refer to Patent Literature 3).

[0008] PRIOR ART DOCUMENTS

[0009] PATENT LITERATURE

[0010] Patent Literature 1: Japanese Patent Application Publication No. 2009-265520

[0011] Patent Literature 2: International Publication No. 2008 / 111470

[0012] Patent Literature 3: Japanese Patent Application Laid-Open No. 2016-199662 SUMMARY

[0013] An object of the present application is to provide a photosensitive resin composition, a method for producing a patterned cured product, a cured product, an interlayer insulating film, a cover coat, a surface protective film, and an electronic component, which are excellent in storage stability, and which can form a cured product excellent in mechanical properties even when cured at a low temperature of 230°C or lower.

[0014] According to the present application, the following photosensitive resin composition and the like can be provided.

[0015] 1. A photosensitive resin composition comprising:

[0016] (A) a polyimide precursor having a polymerizable unsaturated bond,

[0017] (B) a polymerizable monomer,

[0018] (C) a photopolymerization initiator,

[0019] (D) a cyclization catalyst, and

[0020] (E) a solvent.

[0021] 2. The photosensitive resin composition according to 1, wherein the component (A) is a polyimide precursor having a structural unit represented by the following formula (1).

[0022]

[0023] (In formula (1), X1is a 4-valent group having one or more aromatic groups, the -COOR1group and the -CONH- group are in the ortho position to each other, and the -COOR2group and the -CO- group are in the ortho position to each other. Y1is a 2-valent aromatic group. R1and R2are each independently a hydrogen atom, a group represented by the following formula (2), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R1and R2is the group represented by formula (2).)

[0024]

[0025] (In formula (2), R3to R5are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10.)

[0026] 3. The photosensitive resin composition according to 1 or 2, the component (D) is one or more selected from the group consisting of N-phenyldiethanolamine, N-methylaniline, N-ethylaniline, N,N-dimethylaniline, N-phenylethanolamine, 4-phenylmorpholine, and 2,2'-(4-methylphenylimino)diethanol.

[0027] 4. The photosensitive resin composition according to 1 or 2, the component (D) comprises a compound represented by the following formula (17).

[0028]

[0029] (In formula (17), R 31A ~R 33A each independently is a hydrogen atom, a monovalent aliphatic hydrocarbon group, a monovalent aliphatic hydrocarbon group having a hydroxyl group, or a monovalent aromatic group, R 31A ~R 33A at least one of R 31A ~R 33A may form a ring with each other by adjacent groups.)

[0030] 5. The photosensitive resin composition according to any one of 1 to 4, the component (C) comprises (C1) a compound represented by the following formula (15) and (C2) a compound represented by the following formula (16).

[0031]

[0032] (In formula (15), R 11A is an alkyl group having 1 to 12 carbon atoms, and a1 is an integer of 0 to 5. R 12A is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R 13A and R 14A each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a phenyl group, or a tolyl group. In the case where a1 is an integer of 2 or more, R 11A each can be the same or different.)

[0033]

[0034] (In formula (16), R 21A is an alkyl group having 1 to 12 carbon atoms, R 22A and R 23A each independently is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group, and c1 is an integer of 0 to 5. In the case where c1 is an integer of 2 or more, R 21A each can be the same or different.)

[0035] 6. The photosensitive resin composition according to any one of 1 to 5, the component (B) above contains a polymerizable monomer having an aliphatic cyclic skeleton.

[0036] 7. The photosensitive resin composition according to any one of 1 to 6, the component (B) above has a group containing a polymerizable unsaturated double bond.

[0037] 8. The photosensitive resin composition according to 7, the component (B) above is a polymerizable monomer having a group containing two or more polymerizable unsaturated double bonds.

[0038] 9. The photosensitive resin composition according to any one of 1 to 7, the component (B) above contains a polymerizable monomer represented by the following formula (3).

[0039]

[0040] (In formula (3), R6and R7are each independently an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4). n1is 0 or 1, n2is an integer of 0 to 2, and n1+n2is greater than or equal to 1. At least one of n1R6and n2R7is a group represented by the following formula (4).)

[0041]

[0042] (In formula (4), R9to R 11 are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and 1 is an integer of 0 to 10.)

[0043] 10. The photosensitive resin composition according to 9, n1+n2is 2 or 3.

[0044] 11. The photosensitive resin composition according to any one of 1 to 10, the component (B) above contains a polymerizable monomer represented by the following formula (5).

[0045]

[0046] 12. The photosensitive resin composition according to any one of 1 to 11, further comprising (F) a thermal polymerization initiator.

[0047] 13. The photosensitive resin composition according to any one of 1 to 12, further comprising an antioxidant.

[0048] 14. A method for producing a patterned cured product, comprising the following steps:

[0049] a step of applying the photosensitive resin composition according to any one of 1 to 13 on a substrate, and drying to form a photosensitive resin film;

[0050] The process of pattern-exposing the photosensitive resin film to obtain a resin film;

[0051] A process of developing the pattern-exposed resin film using an organic solvent to obtain a patterned resin film; and

[0052] A step of heat-treating the patterned resin film.

[0053] 15. The method for producing a patterned cured product according to 14, wherein the temperature of the heat treatment is 230° C. or less.

[0054] 16. A cured product obtained by curing the photosensitive resin composition according to any one of 1 to 13.

[0055] 17. The cured product according to 16, which is a patterned cured product.

[0056] 18. An interlayer insulating film, a cover coat or a surface protective film produced using the cured product according to 16 or 17.

[0057] 19. An electronic component comprising the interlayer insulating film, cover coat or surface protection film according to 18.

[0058] According to the present invention, there can be provided a photosensitive resin composition capable of forming a cured product having excellent mechanical properties even when cured at a low temperature of 230°C or less and having excellent storage stability, a method for producing a patterned cured product, a cured product, an interlayer insulating film, a cover coat, a surface protective film, and an electronic component. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] Figure 1 This is a diagram showing a manufacturing process of an electronic component according to one embodiment of the present invention. DETAILED DESCRIPTION

[0060] Hereinafter, embodiments of the photosensitive resin composition of the present invention, a method for producing a patterned cured product using the same, a cured product, an interlayer insulating film, a cover coat, a surface protective film, and an electronic component will be described in detail. However, the present invention is not limited to the following embodiments.

[0061] In this specification, the term "A or B" may include either A or B, or both. Furthermore, the term "process" in this specification encompasses not only independent processes but also processes that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved.

[0062] The numerical range represented by "~" indicates a range including the numerical values written before and after "~" as the minimum value and the maximum value, respectively. In addition, regarding the content of each component in the composition in the present specification, in the case where a plurality of substances corresponding to each component is present in the composition, it means the total amount of the plurality of substances present in the composition, unless otherwise specified. Further, the example material can be used alone, or two or more can be used in combination, unless otherwise specified.

[0063] "(Meth)acryloyl" in the present specification means "acryloyl" and "methacryloyl".

[0064] The photosensitive resin composition of the present application contains: (A) a polyimide precursor having a polymerizable unsaturated bond (hereinafter, also referred to as "(A) component"), (B) a polymerizable monomer (also referred to as "crosslinking agent") (hereinafter, also referred to as "(B) component"), (C) a photopolymerization initiator (hereinafter, also referred to as "(C) component"), (D) a cyclization catalyst (hereinafter, also referred to as "(D) component"), and

[0065] (E) a solvent (hereinafter, also referred to as "(E) component").

[0066] Thereby, even if it is low-temperature curing of less than or equal to 230°C, it is possible to form a cured product excellent in mechanical properties.

[0067] Further, it is possible to improve the storage stability.

[0068] Further, as an arbitrary effect, even if it is low-temperature curing of less than or equal to 230°C, it is possible to form a cured product excellent in cyclization rate.

[0069] As an arbitrary effect, it is possible to improve the sensitivity.

[0070] The photosensitive resin composition of the present application is preferably a negative photosensitive resin composition. The photosensitive resin composition of the present application is preferably a material for electronic parts.

[0071] As the (A) component, there is no particular limitation, and it is preferably a polyimide precursor which has a high transmittance when i-line is used as a light source at the time of patterning, and which exhibits high cured product properties even when low-temperature curing of less than or equal to 230°C is performed.

[0072] As the polymerizable unsaturated bond, a carbon-carbon double bond or the like can be mentioned.

[0073] The (A) component is preferably a polyimide precursor having a structural unit represented by the following formula (1). Thereby, the transmittance of i-line is high, and it is possible to form a good cured product even when low-temperature curing of less than or equal to 230°C is performed.

[0074] The content of the structural unit represented by formula (1) with respect to the total structural units of the (A) component is preferably 50 mol% or more, more preferably 80 mol% or more, and further preferably 90 mol% or more. The upper limit is not particularly limited and can also be 100 mol%.

[0075]

[0076] (In formula (1), X1is a 4-valent group having 1 or more aromatic groups, the -COOR1group and the -CONH- group are in the ortho position to each other, and the -COOR2group and the -CO- group are in the ortho position to each other. Y1is a 2-valent aromatic group. R1and R2are each independently a hydrogen atom, a group represented by the following formula (2), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R1and R2is the group represented by formula (2).)

[0077]

[0078] (In formula (2), R3to R5are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10 (preferably an integer of 2 to 5, and more preferably 2 or 3).)

[0079] In the 4-valent group having 1 or more (preferably 1 to 3, and more preferably 1 or 2) aromatic groups of X1of formula (1), the aromatic group can be an aromatic hydrocarbon group or an aromatic heterocyclic group. The aromatic hydrocarbon group is preferred.

[0080] As the aromatic hydrocarbon group of X1of formula (1), a 2- to 4-valent (2-valent, 3-valent, or 4-valent) group formed of a benzene ring, a 2- to 4-valent group formed of naphthalene, a 2- to 4-valent group formed of perylene, and the like can be given.

[0081] As the 4-valent group having 1 or more aromatic groups of X1of formula (1), for example, the 4-valent groups of the following formula (6) can be given, but are not limited thereto.

[0082]

[0083] (In formula (6), X and Y each independently represent a 2-valent group not conjugated with the benzene ring to which each is bonded or a single bond. Z is an ether group (-O-) or a thioether group (-S-) (preferably -O-).)

[0084] In formula (6), the 2-valent group of X and Y not conjugated with the benzene ring to which each is bonded is preferably -O-, -S-, methylene, bis(trifluoromethyl)methylene, or difluoromethylene, and more preferably -O-.

[0085] The divalent aromatic group of Y1of formula (1) can be a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group. It is preferably a divalent aromatic hydrocarbon group.

[0086] As the divalent aromatic hydrocarbon group of Y1of formula (1), for example, the group of the following formula (7) can be given, but is not limited thereto.

[0087]

[0088] (In formula (7), R 12 ~R 19 each independently is a hydrogen atom, a monovalent aliphatic hydrocarbon group, or a monovalent organic group having a halogen atom.)

[0089] As the monovalent aliphatic hydrocarbon group (preferably a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms) of R 12 ~R 19 of formula (7), for example, a methyl group or the like can be given. 12 R 15 ~R 19 is a hydrogen atom, and R 13 and R 14 are monovalent aliphatic hydrocarbon groups.

[0090] The monovalent organic group having a halogen atom (preferably a fluorine atom) of R 12 ~R 19 of formula (7) is preferably a monovalent aliphatic hydrocarbon group having a halogen atom (preferably a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms), and a trifluoromethyl group or the like can be given.

[0091] As the aliphatic hydrocarbon group having 1 to 4 carbon atoms (preferably 1 or 2) of R1and R2of formula (1), for example, a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, an n-butyl group, or the like can be given.

[0092] At least one of R1and R2of formula (1) is preferably a group represented by formula (2), and both are preferably groups represented by formula (2).

[0093] As the aliphatic hydrocarbon group having 1 to 3 carbon atoms (preferably 1 or 2) of R3to R5of formula (2), for example, a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, or the like can be given. A methyl group is preferred.

[0094] A polyimide precursor having a structural unit represented by formula (1) can be obtained, for example, by reacting a tetracarboxylic dianhydride represented by the following formula (8) with a diamino compound represented by the following formula (9) in an organic solvent such as N-methyl-2-pyrrolidone to obtain a polyamic acid, adding a compound represented by the following formula (10), and reacting in an organic solvent to partially introduce an ester group.

[0095] The tetracarboxylic dianhydride represented by formula (8) and the diamino compound represented by formula (9) can be used singly or in combination of two or more.

[0096]

[0097] (In formula (8), X1is a group corresponding to X1of formula (1).)

[0098] H2N-Y1-NH2…(9)

[0099] (In formula (9), Y1is as defined in formula (1).)

[0100] R-OH…(10)

[0101] (In formula (10), R is a group represented by formula (2) described above.)

[0102] The component (A) can also have a structural unit other than the structural unit represented by formula (1).

[0103] As the structural unit other than the structural unit represented by formula (1), a structural unit represented by formula (11) or the like can be given.

[0104]

[0105] (In formula (11), X2is a 4-valent group having one or more aromatic groups, -COOR 51 groups are in the ortho position to each other, and the -COOR 52 groups are in the ortho position to each other. Y2is a 2-valent aromatic group. R 51 and R 52 each independently are a hydrogen atom or an aliphatic hydrocarbon group having 1 to 4 carbon atoms.)

[0106] The 4-valent group having one or more aromatic groups of X2of formula (11) can be the same group as the 4-valent group having one or more aromatic groups of X1of formula (1).

[0107] The 2-valent aromatic group of Y2of formula (11) can be the same group as the 2-valent aromatic group of Y1of formula (1).

[0108] The aliphatic hydrocarbon group having 1 to 4 carbon atoms of R 51 and R 52 of formula (11) can be the same group as the aliphatic hydrocarbon group having 1 to 4 carbon atoms of R1and R2.

[0109] The structural unit other than the structural unit represented by formula (1) can be used singly or in combination of two or more.

[0110] The content of structural units other than the structural unit represented by formula (1) is preferably less than 50 mol% based on all structural units of the component (A).

[0111] In component (A), the ratio of esterified carboxyl groups in the groups represented by formula (2) relative to all carboxyl groups and all carboxylic acid esters is preferably 50 mol% or more, more preferably 60 to 100 mol%, and even more preferably 70 to 90 mol%.

[0112] The molecular weight of the component (A) is not particularly limited, but is preferably 10,000 to 200,000 in terms of number average molecular weight.

[0113] The number average molecular weight can be determined by, for example, measuring it by gel permeation chromatography and converting it using a standard polystyrene calibration curve.

[0114] Component (B) preferably has (preferably two or more) a group containing a polymerizable unsaturated double bond (preferably a (meth)acryloyl group from the perspective of polymerizability by a photopolymerization initiator). Component (B) is preferably a polymerizable monomer having two or more groups containing a polymerizable unsaturated double bond. To increase crosslinking density and sensitivity and suppress pattern swelling after development, it is preferred that the component contain two to three groups containing a polymerizable unsaturated double bond.

[0115] Furthermore, the component (B) may contain a polymerizable monomer having a functional group other than a group containing a polymerizable unsaturated double bond. Examples of the functional group include cyclic ether groups such as an epoxy group and an oxetane group.

[0116] Component (B) preferably contains a polymerizable monomer having an aliphatic cyclic skeleton (preferably having 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms). This imparts hydrophobicity to the resulting cured product and prevents degradation of adhesion between the cured product and the substrate under high-temperature and high-humidity conditions.

[0117] The component (B) preferably contains a polymerizable monomer represented by the following formula (3).

[0118]

[0119] (In formula (3), R6 and R7 are each independently an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4). n1 is 0 or 1, n2 is an integer from 0 to 2, and n1 + n2 is greater than or equal to 1 (preferably 2 or 3). At least one of the n1 R6s and n2 R7s (preferably 2 or 3) is a group represented by the following formula (4).

[0120] When there are two R7s, the two R7s may be the same or different.

[0121]

[0122] (In formula (4), R9to R 11 each independently is a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and 1 is an integer of 0 to 10 (preferably 0, 1, or 2).

[0123] The component (B) more preferably contains a polymerizable monomer represented by the following formula (5).

[0124]

[0125] Further, as the component (B), for example, the following polymerizable monomer can be used.

[0126]

[0127] In formula (12), R 21 to R 24 each independently is an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the above formula (4). n3 is an integer of 1 to 3 (preferably 2 or 3). n4 is an integer of 1 to 3 (preferably 2 or 3). n5 is 0 or 1, and n6 is 0 or 1. n5 + n6 is greater than or equal to 1 (preferably 2).

[0128] In the case where R 21 two or more, two or more of R 21 may be the same or different.

[0129] In the case where R 22 two or more, two or more of R 22 may be the same or different.

[0130] At least one (preferably two or three) of the n3 R 21 is a group represented by the above formula (4).

[0131] At least one (preferably two or three) of the n4 R 22 is a group represented by the above formula (4).

[0132] At least one (preferably two) of the n5 R 23 and the n6 R 24 is a group represented by the above formula (4).

[0133] As the aliphatic hydrocarbon group having 1 to 4 carbon atoms of R6and R7of formula (3) and R 21 to R 24 of formula (12), the same groups as the aliphatic hydrocarbon group having 1 to 4 carbon atoms of R1and R2of formula (1) can be mentioned.

[0134] As the aliphatic hydrocarbon group of 1 to 3 carbon atoms of R9to R 11 The aliphatic hydrocarbon group of 1 to 3 carbon atoms of R3to R5of formula (2) can be exemplified by the same groups as the aliphatic hydrocarbon group of 1 to 3 carbon atoms of R9to R

[0135] The (B) component can include a polymerizable monomer other than the polymerizable monomer having an aliphatic cyclic skeleton. Thereby, a cured product having good mechanical properties can be obtained.

[0136] As the polymerizable monomer other than the polymerizable monomer having an aliphatic cyclic skeleton, for example, 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 triacrylate, trimethylolpropane dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, tetramethylolmethane tetraacrylate, tetramethylolmethane tetramethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated isocyanuric acid triacrylate, ethoxylated isocyanuric acid trimethacrylate, acryloyloxyethyl isocyanurate, methacryloyloxyethyl isocyanurate, ethylene oxide (EO)-modified bisphenol A diacrylate (for example, FA324A (manufactured by Hitachi Chemical Co., Ltd.) as a commercial product), and the like can be exemplified.

[0137] The (B) component can be used alone or in combination of two or more.

[0138] From the viewpoint of obtaining good mechanical properties and photosensitive properties, the (B) component preferably includes a polymerizable monomer having an aliphatic cyclic skeleton and a polymerizable monomer other than the polymerizable monomer having an aliphatic cyclic skeleton.

[0139] In the case of including a polymerizable monomer having an aliphatic cyclic skeleton and a polymerizable monomer other than the polymerizable monomer having an aliphatic cyclic skeleton, the content of the polymerizable monomer having an aliphatic cyclic skeleton is preferably 1 to 40 parts by mass with respect to 100 parts by mass of the (A) component. From the viewpoint of improving the hydrophobicity of the cured product, it is more preferably 5 to 35 parts by mass. The content of the polymerizable monomer other than the polymerizable monomer having an aliphatic cyclic skeleton is preferably 1 to 20 parts by mass with respect to 100 parts by mass of the (A) component. From the viewpoint of improving the hydrophobicity of the cured product, it is more preferably 5 to 15 parts by mass.

[0140] The content of the (B) component is preferably 1 to 50 parts by mass relative to 100 parts by mass of the (A) component. From the viewpoint of improving the hydrophobicity of the cured product, it is more preferably 3 to 50 parts by mass, and further preferably 5 to 40 parts by mass.

[0141] In the above range, a practical concave-convex pattern is easily obtained, and the post-development residue of the unexposed portions is easily suppressed.

[0142] As the (C) component, for example, the following can be preferably selected: benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4'-methylbenzophenone, dibenzyl ketone, fluorenone, and other benzophenone derivatives;

[0143] 2,2'-diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, and other acetophenone derivatives;

[0144] thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone, and other thioxanthone derivatives;

[0145] benzoin, benzoin dimethyl ketal, benzoin-β-methoxyethyl acetal, and other benzoin derivatives;

[0146] benzoin, benzoin dimethyl ketal, benzoin-β-methoxyethyl acetal, and other benzoin derivatives;

[0147] 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-diphenylpropanetone-2-(O-ethoxycarbonyl) oxime, 1-phenyl-3-ethoxypropanetone-2-(O-benzoyl) oxime, ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), a compound represented by the following formula, and other oxime esters, but are not limited thereto.

[0148]

[0149] In particular, from the viewpoint of sensitivity, oxime esters are preferable.

[0150] The (C) component preferably contains a compound represented by the following formula (15) (hereinafter, also referred to as "(C1) component").

[0151] The (C1) component preferably has a higher sensitivity to active light than the (C2) component described later, and is preferably a high-sensitivity photosensitizer.

[0152]

[0153] In formula (15), R 11A is an alkyl group having 1 to 12 carbon atoms, and a1 is an integer of 0 to 5. R 12A is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R 13A and R 14A each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms), a phenyl group, or a tolyl group. In the case where a1 is an integer of 2 or more, R 11A may be the same or different.

[0154] R 11A is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. a1 is preferably 1. R 12A is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an ethyl group. R 13A and R 14A are each independently preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.

[0155] As the compound represented by formula (15), for example, a compound represented by the following formula (15A) can be given, which is available as "IRGACURE OXE 02" manufactured by BASF Japan Ltd.

[0156]

[0157] Further, the (C) component preferably contains a (C2) compound represented by the following formula (16) (hereinafter, also referred to as a "(C2) component").

[0158] The (C2) component is preferably a photosensitizer having a lower sensitivity to active light than the (C1) component, and is preferably a standard photosensitizer.

[0159]

[0160] In formula (16), R 21A is an alkyl group having 1 to 12 carbon atoms, R 22A and R 23A each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably an alkyl group having 1 to 4 carbon atoms), an alkoxy group having 1 to 12 carbon atoms (preferably an alkoxy group having 1 to 4 carbon atoms), a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group, and c1 is an integer of 0 to 5. In the case where c1 is an integer of 2 or more, R 21A may be the same or different.

[0161] c1 is preferably 0. R 22A is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. R 23AAn alkoxy group having 1 to 12 carbon atoms is preferred, an alkoxy group having 1 to 4 carbon atoms is more preferred, and a methoxy group or an ethoxy group is further preferred.

[0162] As the compound represented by formula (16), for example, a compound represented by the following formula (16A) can be mentioned, which is available as "G-1820 (PDO)" manufactured by Lambson Co.

[0163]

[0164] The (C) component can be used singly or in combination of two or more.

[0165] The (C) component preferably contains one or more selected from the group consisting of a (C1) component and a (C2) component.

[0166] Further, the (C) component preferably contains a (C1) component and a (C2) component.

[0167] The content of the (C) component is preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and further preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the (A) component.

[0168] In the above range, photocrosslinking easily becomes uniform in the film thickness direction, and a practical concavo-convex pattern is easily obtained.

[0169] In the case where the (C1) component is contained, the content of the (C1) component is usually 0.05 to 5.0 parts by mass, preferably 0.07 to 2.5 parts by mass, and more preferably 0.09 to 1.0 parts by mass, relative to 100 parts by mass of the (A) component.

[0170] In the case where the (C2) component is contained, the content of the (C2) component is usually 0.5 to 15.0 parts by mass, preferably 1.0 to 15.0 parts by mass, relative to 100 parts by mass of the (A) component.

[0171] In the case where the (C1) component and the (C2) component are contained, the content of the (C1) component is preferably 0.05 to 5.0 parts by mass, and the content of the (C2) component is preferably 0.5 to 15.0 parts by mass, relative to 100 parts by mass of the (A) component.

[0172] In the case where the (C1) component and the (C2) component are contained, the mass ratio of the content of the (C1) component to the content of the (C2) component is preferably 1:2 to 1:15, and more preferably 1:3 to 1:10.

[0173] The photosensitive resin composition of the present application contains a (D) cyclization catalyst.

[0174] (D) component is preferably one or more selected from the group consisting of 2- (methylphenylamino)ethanol, 2-(ethylanilino)ethanol, N-phenyldiethanolamine, N-methylaniline, N-ethylaniline, N,N-dimethylaniline, N-phenylethanolamine, 4-phenylmorpholine, and 2,2'-(4-methylphenylimino)diethanol, more preferably one or more selected from the group consisting of N-phenyldiethanolamine, N-methylaniline, N-ethylaniline, N,N-dimethylaniline, N-phenylethanolamine, 4-phenylmorpholine, and 2,2'-(4-methylphenylimino)diethanol.

[0175] The (D) component preferably contains a compound represented by the following formula (17).

[0176]

[0177] (In formula (17), R 31A ~R 33A each independently is a hydrogen atom, a monovalent aliphatic hydrocarbon group, a monovalent aliphatic hydrocarbon group having a hydroxyl group, or a monovalent aromatic group, R 31A ~R 33A at least one of (preferably one of) R 31A ~R 33A is a monovalent aromatic group. R 31A ~R 33A may form a ring with each other (for example, a 5-membered ring or a 6-membered ring which can have a substituent (for example, a methyl group, a phenyl group)).

[0178] Preferably, further, at least one of R 31A ~R 33A is a monovalent aliphatic hydrocarbon group, a monovalent aliphatic hydrocarbon group having a hydroxyl group, or a monovalent aromatic group.

[0179] As the monovalent aliphatic hydrocarbon group (preferably a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms) of R 31A ~R 33A of formula (17), there can be mentioned a methyl group, an ethyl group, and the like.

[0180] As the monovalent aliphatic hydrocarbon group having a hydroxyl group of R 31A ~R 33A of formula (17), there can be mentioned a group in which one or more (preferably 1 to 3) hydroxyl groups are bonded to a monovalent aliphatic hydrocarbon group of R 31A ~R 33A , and the like. Specifically, there can be mentioned a hydroxymethyl group, a hydroxyethyl group, and the like. Preferably, it is a hydroxyethyl group.

[0181] As the monovalent aliphatic hydrocarbon group (preferably a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms) of R 31A ~R 33AThe monovalent aromatic group of the formula (17) can be a monovalent aromatic hydrocarbon group (preferably a carbon number of 6 to 12, more preferably a carbon number of 6 to 10), or a monovalent aromatic heterocyclic group. It is preferable to be a monovalent aromatic hydrocarbon group.

[0182] As the monovalent aromatic hydrocarbon group, a phenyl group, a naphthyl group, and the like can be given.

[0183] R of the formula (17) 31A R of the formula (17) 33A The monovalent aromatic group of the formula (17) can also have a substituent. As the substituent, the same group as R 31A R of the formula (17) 33A The monovalent aliphatic hydrocarbon group of the formula (17) can also have a substituent. As the substituent, the same group as R 31A R of the formula (17) 33A The monovalent aliphatic hydrocarbon group of the formula (17) having a hydroxyl group can also have a substituent. As the substituent, the same group as R

[0184] The (D) component can be used alone or in combination of two or more.

[0185] From the viewpoint of improving the imidation rate and sensitivity, the content of the (D) component is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the (A) component. From the viewpoint of storage stability, it is more preferable to be 0.3 to 15 parts by mass, and further preferable to be 0.5 to 10 parts by mass.

[0186] The photosensitive resin composition of the present application contains a (E) solvent.

[0187] As the (E) component, N-methyl-2-pyrrolidone, γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, benzyl acetate, n-butyl acetate, ethyl ethoxypropionate, 3-methoxy methyl propionate, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, sulfolane, cyclohexanone, cyclopentanone, diethyl ketone, diisobutyl ketone, methyl amyl ketone, N-dimethyl morpholine, and the like can be given, and there is no particular limitation as long as it can sufficiently dissolve the other components.

[0188] Among them, from the viewpoint of solubility of each component and excellent coatability at the time of forming a photosensitive resin film, it is preferable to use N-methyl-2-pyrrolidone, γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, N,N-dimethylformamide, N,N-dimethylacetamide.

[0189] Further, as the (E) component, a compound represented by the following formula (21) can be used.

[0190]

[0191] (In the formula, R 41 R of the formula (17) 43each independently is an alkyl group having 1 to 10 carbon atoms.

[0192] R in the formula (21) is preferably a group represented by the formula (22). 41 ~R 43 An alkyl group having 1 to 10 carbon atoms (preferably 1 to 3, more preferably 1 or 3) can be exemplified by methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, and the like.

[0193] The compound represented by the formula (21) is preferably 3-methoxy-N,N-dimethylpropanamide (for example, trade name "KJCMPA-100" (manufactured by KJ Chemical Co., Ltd.).

[0194] The (E) component can be used singly or in combination of two or more.

[0195] The content of the (E) component is not particularly limited, and is generally 50 to 1000 parts by mass per 100 parts by mass of the (A) component.

[0196] From the viewpoint of promoting the polymerization reaction, the photosensitive resin composition of the present application can further contain a (F) thermal polymerization initiator (hereinafter, also referred to as "(F) component").

[0197] As the (F) component, a compound which does not decompose in heating (drying) for removing the solvent used for film formation, but decomposes by heating at the time of curing and generates a radical, thereby promoting the polymerization reaction of the (B) components with each other, or the (A) component and the (B) component, is preferred.

[0198] The (F) component is preferably a compound having a decomposition point of greater than or equal to 110°C and less than or equal to 200°C, and more preferably a compound having a decomposition point of greater than or equal to 110°C and less than or equal to 175°C from the viewpoint of promoting the polymerization reaction at a lower temperature.

[0199] As specific examples, there can be mentioned ketone peroxides such as methyl ethyl ketone peroxide; peroxyketal such as 1,1-di(tert-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(tert-hexylperoxy)cyclohexane, 1,1-di(tert-butylperoxy)cyclohexane; hydroperoxide such as 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, p-menthane hydroperoxide; dialkyl peroxide such as dicumyl peroxide, di-tert-butyl peroxide; diacyl peroxide such as dilauroyl peroxide, dibenzoyl peroxide; peroxydicarbonate such as di(4-tert-butylcyclohexyl) peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate; peroxyester such as tert-butylperoxy-2-ethylhexanoate, tert-hexylperoxy isopropyl monocarbonate, tert-butylperoxy benzoate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate; and the like. As commercially available products, there can be mentioned products under the trade names of "Percumyl D", "Percumyl P", "Percumyl H" (all manufactured by Nippon Oil & Fats Corporation), and the like.

[0200] In the case where the (F) component is contained, the content of the (F) component is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 20 parts by mass, and further preferably 0.3 to 10 parts by mass, relative to 100 parts by mass of the (A) component, in order to ensure good resistance to flux.

[0201] The photosensitive resin composition of the present application can further contain an antioxidant. By containing an antioxidant, oxygen radicals and peroxide radicals generated due to high-temperature storage or reflow processing are replenished, and the reduction in adhesion (cohesion) can be further suppressed. In addition, electrode oxidation at the time of insulation reliability testing can be suppressed, and diffusion from the electrode to the resin film or pattern resin film can be suppressed.

[0202] As the antioxidant, there can be mentioned N,N'-bis[2-[2-(3,5-di-tert-butyl-4- hydroxyphenyl)ethylcarbonyloxy]ethyl]oxamide, N,N'-bis-3-(3,5-di-tert-butyl-4'- hydroxyphenyl)propionylhexamethylenediamide, 1,3,5-tris(3-hydroxy-4-tert-butyl-2,6- dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione,

[0203] 2,6-di-tert-butyl-4-methylphenol, 2,5-di-tert-butylhydroquinone, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-thio-bis(3-methyl-6-tert-butylphenol), 4,4'-butylidene-bis(3-methyl-6-tert-butylphenol), triethyleneglycol bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 2,2-thiodiethyleneglycol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxyhydrocinnamamide), isooctyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-tris[4-triethylmethyl-3-hydroxy-2,6-dimethylbenzyl]-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), 2,2'-methylene-bis(4-ethyl-6-tert-butylphenol),

[0204] tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris(3-hydroxy-2,6-dimethyl-4-isopropylbenzyl)-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 1,3,5-tris(4-sec-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 1,3,5-tris[4-(1 -ethylpropyl)-3-hydroxy-2,6-dimethylbenzyl]-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1 H,3H,5H)-trione,

[0205] Pentaerythritol [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 1,6-hexanediol bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 1,3,5-tris(4-tert-butyl-3-hydroxy-2,5,6-trimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-6-ethyl-3-hydroxy-2,5-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-5,6-diethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(4-tert-butyl-6-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione,

[0206] 1,3,5-tris(4-tert-butyl-5-ethyl-3-hydroxy-2-methylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(3-hydroxy-2,6-dimethyl-4-phenylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, and

[0207] 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanuric acid, and the like.

[0208] The antioxidant can be used singly or in combination of two or more kinds.

[0209] In the case where the antioxidant is contained, the content of the antioxidant is preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and further preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the (A) component.

[0210] The photosensitive resin composition of the present application can further contain a coupling agent (adhesion aid), a surfactant or a leveling agent, a rust preventive, a polymerization inhibitor, and the like.

[0211] Generally, the coupling agent is crosslinked by reacting with the (A) component in the heating treatment after development, or the coupling agent itself is polymerized in the process of the heating treatment. Thereby, the adhesion of the obtained cured product to the substrate can be further improved.

[0212] As the preferred silane coupling agent, a compound having a urea bond (-NH-CO-NH-) can be mentioned. Thereby, the adhesion to the substrate can be further improved even in the case of curing at a low temperature of 230°C or less.

[0213] Since the adhesion at the time of curing at a low temperature is excellent, a compound represented by the following formula (13) is more preferred.

[0214]

[0215] (In formula (13), R 31 and R 32 each independently is an alkyl group having 1 to 5 carbon atoms. a is an integer of 1 to 10, and b is an integer of 1 to 3.)

[0216] As the specific examples of the compound represented by formula (13), ureidomethyltrimethoxysilane, ureidomethyltriethoxysilane, 2-ureidoethyltrimethoxysilane, 2-ureidoethyltriethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 4-ureidobutyltrimethoxysilane, 4-ureidobutyltriethoxysilane, and the like can be mentioned, and 3-ureidopropyltriethoxysilane is preferred.

[0217] As the silane coupling agent, a silane coupling agent having a hydroxyl group or a glycidyl group can also be used. If a silane coupling agent having a hydroxyl group or a glycidyl group and a silane coupling agent having a urea bond in the molecule are used in combination, the adhesion of the cured product to the substrate at the time of low-temperature curing can be further improved.

[0218] As the silane coupling agent having a hydroxyl group or a glycidyl group, there can be mentioned methylphenylsilanediol, ethylphenylsilanediol, n-propylphenylsilanediol, isopropylphenylsilanediol, n-butylphenylsilanediol, isobutylphenylsilanediol, t-butylphenylsilanediol, diphenylsilanediol, ethylmethylphenylsilanol, n-propylmethylphenylsilanol, isopropylmethylphenylsilanol, n-butylmethylphenylsilanol, isobutylmethylphenylsilanol, t-butylmethylphenylsilanol, ethyl n-propylphenylsilanol, ethyl isopropylphenylsilanol, n-butyl ethylphenylsilanol, isobutyl ethylphenylsilanol, t-butyl ethylphenylsilanol, methyldiphenylsilanol, ethyldiphenylsilanol, n-propyldiphenylsilanol, isopropyldiphenylsilanol, n-butyldiphenylsilanol, isobutyldiphenylsilanol, t-butyldiphenylsilanol, phenylsilanetriol, 1,4-bis(trihydroxysilyl)benzene, 1,4-bis(methyldihydroxysilyl)benzene, 1,4-bis(ethyldihydroxysilyl)benzene, 1,4-bis(propyldihydroxysilyl)benzene, 1,4-bis(butyldihydroxysilyl)benzene, 1,4-bis(dimethylhydroxysilyl)benzene, 1,4-bis(diethylhydroxysilyl)benzene, 1,4-bis(dipropylhydroxysilyl)benzene, 1,4-bis(dibutylhydroxysilyl)benzene, and a compound represented by the following formula (14), etc. Among them, in order to further improve the adhesion to the substrate, the compound represented by the formula (14) is particularly preferred.

[0219]

[0220] (In the formula (14), R 33 is a monovalent organic group having a hydroxyl group or a glycidyl group, R 34 and R 35 each independently is an alkyl group having 1 to 5 carbon atoms. c is an integer of 1 to 10, and d is an integer of 1 to 3.)

[0221] As the compound represented by the formula (14), there can be mentioned hydroxymethyltrimethoxysilane, hydroxymethyltriethoxysilane, 2-hydroxyethyltrimethoxysilane, 2-hydroxyethyltriethoxysilane, 3-hydroxypropyltrimethoxysilane, 3-hydroxypropyltriethoxysilane, 4-hydroxybutyltrimethoxysilane, 4-hydroxybutyltriethoxysilane, glycidoxy-methyltrimethoxysilane, glycidoxy-methyltriethoxysilane, 2-glycidoxyethyltrimethoxysilane, 2-glycidoxyethyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 4-glycidoxybutyltrimethoxysilane, 4-glycidoxybutyltriethoxysilane, etc.

[0222] The silane coupling agent having a hydroxyl group or a glycidyl group preferably further contains a group having a nitrogen atom, preferably a silane coupling agent further having an amino group or an amide bond.

[0223] As the silane coupling agent further having an amino group, there can be mentioned bis(2-hydroxymethyl)-3-aminopropyltriethoxysilane, bis(2-hydroxymethyl)-3-aminopropyltrimethoxysilane, bis(2- glycidyloxymethyl)-3-aminopropyltriethoxysilane, bis(2-hydroxymethyl)-3- aminopropyltrimethoxysilane, and the like.

[0224] As the silane coupling agent further having an amide bond, there can be mentioned R 36 -(CH2) e -CO-NH-(CH2) f -Si(OR 37 )3(R 36 is a hydroxyl group or a glycidyl group, e and f each independently are an integer of 1 to 3, R 37 is a methyl group, an ethyl group or a propyl group), and the like.

[0225] The silane coupling agent can be used singly or in combination of two or more.

[0226] In the case of using the silane coupling agent, the content of the silane coupling agent is preferably 0.1 to 20 parts by mass, more preferably 0.3 to 10 parts by mass, and further preferably 1 to 10 parts by mass, relative to 100 parts by mass of the (A) component.

[0227] By containing a surfactant or a leveling agent, it is possible to improve the coatability (for example, to suppress streaks (unevenness in film thickness)) and the developability.

[0228] As the surfactant or the leveling agent, there can be mentioned, for example, polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, and the like, and as commercially available products, there can be mentioned "MEGAFAX F171", "F173", "R-08" (all manufactured by DIC Corporation); "FLUORAD FC430", "FC431" (all manufactured by Sumitomo 3M Company); "Organosiloxane Polymer KP341", "KBM303", "KBM403", "KBM803" (all manufactured by Shin-Etsu Chemical Co., Ltd.), and the like.

[0229] The surfactant and the leveling agent can be used singly or in combination of two or more.

[0230] In the case of containing the surfactant or the leveling agent, the content of the surfactant or the leveling agent is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and further preferably 0.05 to 3 parts by mass, relative to 100 parts by mass of the (A) component.

[0231] By containing the rust preventive, corrosion of copper and copper alloys can be inhibited, and discoloration can be prevented.

[0232] As the rust preventive, for example, triazole derivatives and tetrazole derivatives, and the like can be given.

[0233] The rust preventive can be used alone or in combination of two or more.

[0234] In the case of using the rust preventive, the content of the rust preventive is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and further preferably 0.5 to 3 parts by mass, relative to 100 parts by mass of the (A) component.

[0235] By containing the polymerization inhibitor, it is possible to ensure good storage stability.

[0236] As the polymerization inhibitor, for example, radical polymerization inhibitors, radical polymerization inhibitors, and the like can be given.

[0237] As the polymerization inhibitor, for example, p-methoxyphenol, diphenyl-p-benzoquinone, benzoquinone, hydroquinone, pyrogallol, phenothiazine, resorcinol, o-dinitrobenzene, p-dinitrobenzene, m-dinitrobenzene, phenanthraquinone, N-phenyl-2-naphthylamine, Cupferron, 2,5-toluquinone, tannic acid, p-benzylaminophenol, nitrosamines, and the like can be given.

[0238] The polymerization inhibitor can be used alone or in combination of two or more.

[0239] In the case of containing the polymerization inhibitor, the content of the polymerization inhibitor is preferably 0.01 to 30 parts by mass, more preferably 0.01 to 10 parts by mass, and further preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the (A) component, from the viewpoint of the storage stability of the photosensitive resin composition and the heat resistance of the obtained cured product.

[0240] The photosensitive resin composition of the present application is substantially composed of the (A) to (E) components, and the optional (F) component, the coupling agent, the surfactant, the leveling agent, the rust preventive, and the polymerization inhibitor, and can also contain unavoidable impurities within a range that does not impair the effects of the present application.

[0241] For example, 80% by mass or more, 90% by mass or more, 95% by mass or more, 98% by mass or more, or 100% by mass of the photosensitive resin composition of the present application can be composed of

[0242] (A) to (E) components,

[0243] (A) to (F) components, or

[0244] (A) to (E) components, and, if any, the (F) component, a coupling agent, a surfactant, a leveling agent, an antirust agent, and a polymerization inhibitor.

[0245] The cured product of the present application can be obtained by curing the above-mentioned photosensitive resin composition.

[0246] The cured product of the present application can be used as a patterned cured product, or as a non-patterned cured product.

[0247] The film thickness of the cured product of the present application is preferably 5 to 20 μm.

[0248] The method for producing a patterned cured product of the present application includes the following steps: a step of applying the above-mentioned photosensitive resin composition to a substrate, and drying to form a photosensitive resin film; a step of performing pattern exposure of the photosensitive resin film to obtain a resin film; a step of developing the resin film after the pattern exposure using an organic solvent to obtain a patterned resin film; and a step of performing heat treatment of the patterned resin film.

[0249] Thereby, a patterned cured product can be obtained.

[0250] The method for producing a non-patterned cured product, for example, includes a step of forming the above-mentioned photosensitive resin film, and a step of performing heat treatment. It can further include a step of exposure.

[0251] As the substrate, a glass substrate, a Si substrate (silicon wafer), and the like semiconductor substrates; a TiO2 substrate, a SiO2 substrate, and the like metal oxide insulator substrates; a silicon nitride substrate, a copper substrate, a copper alloy substrate, and the like can be mentioned.

[0252] The coating method is not particularly limited, and a spin coater or the like can be used.

[0253] The drying can be performed using a hot plate, an oven, or the like.

[0254] The drying temperature is preferably 90 to 150°C, and more preferably 90 to 120°C from the viewpoint of ensuring the dissolution contrast.

[0255] The drying time is preferably 30 seconds to 5 minutes.

[0256] The drying can be performed 2 or more times.

[0257] Thereby, a photosensitive resin film in which the above-mentioned photosensitive resin composition is formed into a film can be obtained.

[0258] The thickness of the photosensitive resin film is preferably 5 to 100 μm, more preferably 6 to 50 μm, and further preferably 7 to 30 μm.

[0259] The pattern exposure is, for example, exposure to a predetermined pattern through a photomask.

[0260] The active light to be irradiated can be, for example, ultraviolet light such as i-line and broadband (BB); visible light; and radioactive rays, and is preferably i-line.

[0261] As the exposure device, a parallel exposure machine, a projection exposure machine, a step-and-repeat exposure machine, a step-and- scan exposure machine, and the like can be used.

[0262] By performing development, a resin film formed with a pattern (pattern resin film) can be obtained. In general, in the case of using a negative photosensitive resin composition, the unexposed portions are removed using a developer.

[0263] The organic solvent used as the developer can be used alone as a good solvent for the photosensitive resin film, or a good solvent and a poor solvent can be used in an appropriate mixture as the developer.

[0264] As the good solvent, N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, γ-butyrolactone, α-acetyl-γ-butyrolactone, cyclopentanone, cyclohexanone, and the like can be used.

[0265] As the poor solvent, toluene, xylene, methanol, ethanol, isopropanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, water, and the like can be used.

[0266] A surfactant can be added to the developer. As the amount of addition, 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the developer, is preferable.

[0267] The development time can be, for example, twice the time until the photosensitive resin film is completely dissolved by being immersed.

[0268] The development time differs depending on the component (A) used, and is preferably 10 seconds to 15 minutes, more preferably 10 seconds to 5 minutes, and further preferably 20 seconds to 5 minutes from the viewpoint of productivity.

[0269] After development, washing can be performed using a rinsing liquid.

[0270] As the rinsing liquid, distilled water, methanol, ethanol, isopropanol, toluene, xylene, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and the like can be used alone or in an appropriate mixture, and can also be used in combination in stages.

[0271] By performing a heat treatment on the patterned resin film, a patterned cured product can be obtained.

[0272] The polyimide precursor of the (A) component undergoes a dehydration ring closure reaction by the heat treatment process, and generally forms a corresponding polyimide.

[0273] The temperature of the heat treatment is preferably 250°C or less, more preferably 120 to 250°C, and further preferably 230°C or less or 180 to 230°C.

[0274] By setting within the above range, damage to the substrate and the device can be suppressed to be small, the device can be produced with good yield, and energy saving of the process can be achieved.

[0275] The time of the heat treatment is preferably 5 hours or less, and more preferably 30 minutes to 3 hours.

[0276] By setting within the above range, the cross-linking reaction or the dehydration ring closure reaction can be sufficiently performed.

[0277] The atmosphere of the heat treatment can be in the air or in a non-reactive atmosphere such as nitrogen, and from the viewpoint of preventing oxidation of the patterned resin film, the nitrogen atmosphere is preferred.

[0278] As the device used in the heat treatment, a quartz tube furnace, a hot plate, a rapid annealing furnace, a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, a microwave curing furnace, and the like can be mentioned.

[0279] The cured product of the present application can be used as a passivation film, a buffer coating film, an interlayer insulation film, a cover coat, a surface protection film, and the like.

[0280] By using one or more selected from the group consisting of the passivation film, the buffer coating film, the interlayer insulation film, the cover coat, the surface protection film, and the like, a semiconductor device, a multilayer wiring board, various electronic devices, a stacked device (a multi-chip fan-out wafer level package, and the like), and the like, which have high reliability, can be manufactured.

[0281] An example of a manufacturing process of a semiconductor device as an electronic component of the present application will be described with reference to the drawings.

[0282] Figure 1 is a manufacturing process diagram of a semiconductor device of a multilayer wiring structure as an electronic component according to an embodiment of the present application.

[0283] In Figure 1 , a semiconductor substrate 1 such as a Si substrate having a circuit element is covered with a protective film 2 such as a silicon oxide film except for a predetermined portion of the circuit element, and a first conductor layer 3 is formed on the exposed circuit element. Then, an interlayer insulation film 4 is formed on the above semiconductor substrate 1.

[0284] Next, a photosensitive resin layer 5 of a chlorinated rubber-based, a phenol novolak-based, or the like is formed on the interlayer insulating film 4, and a window 6A is provided by a known photolithography technique so that a predetermined portion of the interlayer insulating film 4 is exposed.

[0285] The interlayer insulating film 4 exposed by the window 6A is selectively etched, and a window 6B is provided.

[0286] Next, the photosensitive resin layer 5 is completely removed using an etching solution that does not etch the first conductor layer 3 exposed by the window 6B but etches only the photosensitive resin layer 5.

[0287] Further, a second conductor layer 7 is formed in electrical connection with the first conductor layer 3 using a known photolithography technique.

[0288] In the case of forming a multilayer wiring structure of three or more layers, the above-described procedures can be repeated to form each layer.

[0289] Next, a surface protective film 8 is formed by pattern exposure using the above-described photosensitive resin composition to provide a window 6C. The surface protective film 8 protects the second conductor layer 7 from stress, α-rays, and the like from the outside, and the resulting semiconductor device is excellent in reliability.

[0290] In the above-described example, the photosensitive resin composition of the present application can also be used to form the interlayer insulating film.

[0291] Example

[0292] Hereinafter, the present application will be further specifically described based on examples and comparative examples. The present application is not limited to the following examples.

[0293] Synthesis Example 1 (Synthesis of A1)

[0294] A solution of 7.07 g of 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride (ODPA) and 4.12 g of 2,2'-dimethyl biphenyl-4,4'-diamine (DMAP) was prepared in 30 g of N-methyl-2-pyrrolidone (NMP) and stirred at 30°C for 4 hours and then stirred at room temperature overnight to obtain a polyamic acid. To this solution, 9.45 g of trifluoroacetic anhydride was added under water cooling and stirred at 45°C for 3 hours, and 7.08 g of 2-hydroxyethyl methacrylate (HEMA) was added. The reaction solution was added dropwise to distilled water, the precipitate was separated by filtration and collected, and dried under reduced pressure to obtain a polyimide precursor A1.

[0295] The number average molecular weight was determined by a gel permeation chromatography (GPC) method by conversion to a standard polystyrene under the following conditions. The number average molecular weight of A1 was 40,000.

[0296] The measurement was performed using a solution of 1 mL of solvent [tetrahydrofuran (THF) / dimethylformamide (DMF) = 1 / 1 (volume ratio)] relative to 0.5 mg of Al.

[0297] Measurement device: L4000 UV manufactured by Shimadzu Corporation

[0298] Pump: L6000 manufactured by Shimadzu Corporation

[0299] C-R4A Chromatopac manufactured by Shimadzu Corporation

[0300] Measurement conditions: Column Gelpack GL-S300MDT-5 x 2

[0301] Eluent: THF / DMF = 1 / 1 (volume ratio)

[0302] LiBr (0.03 mol / L), H3PO4 (0.06 mol / L)

[0303] Flow rate: 1.0 mL / min, Detector: UV 270 nm

[0304] Further, NMR measurement was performed under the following conditions, and the esterification rate (reaction rate of the carboxyl group of ODPA with HEMA) of Al was calculated. The esterification rate was 80 mol% relative to the total carboxyl group of the polyamic acid (20 mol% of the remaining was a carboxyl group).

[0305] Measurement device: AV400M manufactured by Bruker BioSpin Corporation

[0306] Magnetic field strength: 400 MHz

[0307] Reference substance: Tetramethylsilane (TMS)

[0308] Solvent: Dimethyl sulfoxide (DMSO)

[0309] Examples 1 to 3 and Comparative Examples 1 to 5

[0310] (Preparation of the photosensitive resin composition)

[0311] The photosensitive resin compositions of Examples 1 to 3 and Comparative Examples 1 to 5 were prepared in accordance with the components and blending amounts shown in Table 1. The blending amounts of Table 1 are mass parts of each component relative to 100 mass parts of Al.

[0312] Each component used is described below. As the (A) component, Al obtained in Synthesis Example 1 was used.

[0313] (B) component: Polymerizable monomer

[0314] B1: A-DCP (manufactured by Shin-Nakamura Chemical Industries, Ltd., tricyclodecane dimethanol diacrylate, compound represented by the following formula B1)

[0315]

[0316] B2: ATM-4E (manufactured by Shin-Nakamura Chemical Industries, Ltd., ethoxylated pentaerythritol tetraacrylate, compound represented by the following formula (n11 + n12 + n13 + n14 is 4))

[0317]

[0318] B3: FA-324A (manufactured by Hitachi Chemical Co., Ltd., EO-modified bisphenol A diacrylate, compound represented by the following formula B3)

[0319]

[0320] (C) Component: photopolymerization initiator

[0321] C1: IRGACURE OXE 02 (manufactured by BASF Japan Ltd., ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime))

[0322] C2: G-1820 (PDO) (manufactured by Lambson Co., Ltd., 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl) oxime)

[0323] (D) Component: cyclization catalyst

[0324] D1: 2HE (manufactured by Morin Chemical Industries, Ltd., N-phenyldiethanolamine)

[0325] (D') Component

[0326] D2: U-CAT SA810 (manufactured by San-Apro Co., Ltd., compound represented by the following formula D2)

[0327]

[0328] D3: U-CAT SA1 (manufactured by San-Apro Co., Ltd., compound represented by the following formula D3)

[0329]

[0330] D4: 4-hydroxypyridine

[0331] (E) Component: solvent

[0332] E1: KJ CMPA-100 (manufactured by KJ Chemical Co., Ltd., a compound represented by the following formula E1)

[0333]

[0334] (F) Component: thermal polymerization initiator

[0335] F1: Percumyl D (manufactured by Nippon Oil & Fats Corporation, bis (1-phenyl-1-methylethyl) peroxide, a compound represented by the following formula F1)

[0336]

[0337] (Evaluation of sensitivity)

[0338] A coating device Act8 (manufactured by Tokyo Electron Co., Ltd.) was used to spin coat the obtained photosensitive resin composition on a silicon wafer, and after drying at 105°C for 120 seconds, drying at 115°C for 120 seconds, a photosensitive resin film having a dry film thickness of 13 μm was formed.

[0339] The developing time was set to twice the time until the obtained photosensitive resin film was completely dissolved by immersion in cyclopentanone.

[0340] Further, a photosensitive resin film was produced in the same manner as described above, and for the obtained photosensitive resin film, an i-line step-and-exposure machine FPA-3000iW (manufactured by Canon Inc.) was used to perform exposure at 100 to 1100 mJ / cm 2 of i-line at a dose of 100 to 1100 mJ / cm 2 per 100 mJ / cm

[0341] After the exposed resin film was developed in cyclopentanone at the developing time described above using Act8, it was rinsed with propylene glycol monomethyl ether acetate (PGMEA) to obtain a pattern resin film.

[0342] The lower limit of the exposure amount at which the film thickness of the obtained pattern resin film became greater than or equal to 80% of the film thickness of the photosensitive resin film before exposure was set as the sensitivity. The results are shown in Table 1.

[0343] (Production 1 of pattern cured product)

[0344] A pattern resin film obtained in the evaluation of sensitivity was heated at 200°C for 2 hours under a nitrogen atmosphere using a vertical diffusion furnace μ-TF (manufactured by Lightn Thermo System Co., Ltd.) to obtain a pattern cured product (cured film thickness 10 μm).

[0345] (Production 2 of pattern cured product)

[0346] The pattern resin film obtained in the evaluation of sensitivity was heated at 400°C for 1 hour under a nitrogen atmosphere using a vertical diffusion furnace μ-TF to obtain a pattern cured product.

[0347] (Evaluation of cyclization rate)

[0348] For the pattern resin film obtained in the evaluation of sensitivity, the IR (infrared spectroscopic analysis) spectrum was measured using FT-IR IRAffinity-1S (manufactured by Shimadzu Corporation) under the following conditions. This value was set as IR1.

[0349] As to the measurement conditions of the IR spectrum, the measurement range was 400 to 4000 cm -1 , and the cumulative number was 16 times by the transmission method.

[0350] The measurement of the IR spectrum used a silicon wafer as a substrate. First, the measurement was performed on a substrate to which the photosensitive resin composition was not applied, and this was set as a background. Next, the measurement was performed on the resin film portion of the pattern resin film using the above background, and the IR spectrum was obtained.

[0351] Further, for the pattern cured product obtained in the production 1 of pattern cured product, the IR was measured in the same manner as above. This value was set as IR2.

[0352] For the pattern cured product obtained in the production 2 of pattern cured product, the IR was measured in the same manner as above. This value was set as IR3.

[0353] The value obtained by subtracting IR1 from IR2 was divided by the value obtained by subtracting IR1 from IR3, and the percentage was calculated, whereby the cyclization rate was found. Greater than or equal to 65% was set as A, and less than 65% was set as B. The results are shown in Table 1.

[0354] (Evaluation of storage stability)

[0355] For the above photosensitive resin composition, within 24 hours after adjustment, the photosensitive resin film was formed on a Si substrate by spin coating at a rotation number such that the film thickness after drying became 13 μm, drying on a hot plate at 105°C for 120 seconds, and drying at 115°C for 120 seconds. By scratching a part of the film to expose the silicon wafer, the height from the surface of the exposed silicon wafer to the film surface was measured using a probe-type profilometer Dektak 150 (manufactured by Bruker Corporation) (the measurement of the film thickness was the same as above, and also the same below). This was set as film thickness 1.

[0356] The above-mentioned photosensitive resin composition was left to stand at room temperature (25°C) for 14 days after adjustment. After the standing, the photosensitive resin film was formed on a Si substrate by spin coating at the same number of rotations as when the photosensitive resin film for the measurement of film thickness 1 was formed, and was dried on a hot plate at 105°C for 120 seconds and at 115°C for 120 seconds. The film thickness was measured in the same manner as described above. This was taken as film thickness 2.

[0357] The case where the value obtained by dividing the absolute value of the difference between film thickness 2 and film thickness 1 by film thickness 1 and calculating the percentage was 5% or less was taken as A. The case where it exceeded 5% was taken as B. The results are shown in Table 1.

[0358] (Production of patterned cured product 3)

[0359] The above-mentioned photosensitive resin composition was spin coated on a Si substrate, and dried on a hot plate at 105°C for 120 seconds and at 115°C for 120 seconds to form a photosensitive resin film of 12.0 to 13.0 μm.

[0360] The obtained photosensitive resin film was subjected to broadband (BB) exposure using a mask aligner MA-8 (manufactured by Suss MicroTec), and the exposed resin film was developed using cyclopentanone to obtain a patterned resin film in the form of a long strip of 10 mm in width.

[0361] The obtained patterned resin film was cured at 200°C for 2 hours under a nitrogen atmosphere using a vertical diffusion furnace μ-TF to obtain a patterned cured product of 10 μm in film thickness.

[0362] (Evaluation of elongation)

[0363] The patterned cured product obtained in the production of patterned cured product 3 was immersed in a 4.9 mass% aqueous hydrofluoric acid solution, and the cured product of 10 mm in width was peeled from the wafer.

[0364] The 10 mm wide cured product after peeling was subjected to a tensile test using an Autograph AGS-X 100N (manufactured by Shimadzu Corporation). The distance between the grips was set to 20 mm, the tensile speed was set to 5 mm / minute, and the measurement temperature was set to 18 to 25°C, and the elongation was measured 3 times for each of the cured products of the examples and the comparative examples, and the average value was calculated.

[0365] The case where the average value of the elongation exceeded 50% was taken as A, the case where it exceeded 45% and was 50% or less was taken as B, and the case where it was 45% or less was taken as C. The results before the PCT (pressure cooker test) are shown in Table 1.

[0366] Further, the patterned cured product obtained in the above-mentioned production 3 of patterned cured product was treated at 121°C, 100 RH (Relative Humidity) %, 2 atm for 100 hours using a PCT test device HASTEST (manufactured by HAYASHI KAKO CO., LTD., PC-R8D).

[0367] The patterned cured product was taken out from the PCT test device, peeled off in the same manner as described above and subjected to a tensile test, and the average value of elongation was calculated.

[0368] The case where the average value of elongation exceeds 50% was set as A, the case where it exceeds 45% and is less than or equal to 50% was set as B, and the case where it is less than or equal to 45% was set as C. The results after PCT are shown in Table 1. "-" indicates that it was not measured.

[0369] [Table 1]

[0370]

[0371] Industrial Applicability

[0372] The photosensitive resin composition of the present application can be used for an interlayer insulating film, a cover coat or a surface protective film, etc., and the interlayer insulating film, the cover coat or the surface protective film of the present application can be used for electronic parts, etc.

[0373] The above detailed several embodiments and / or examples of the present application, but those skilled in the art will readily make various changes in the embodiments and / or examples as exemplified without departing from the new teachings and effects of the present application in substance. Therefore, these various changes are also included in the scope of the present application.

[0374] The documents described in this specification and all the contents of the application based on Paris priority convention of the present application are incorporated herein by reference.

Claims

1. A photosensitive resin composition comprising: (A) a polyimide precursor having a polymerizable unsaturated bond, (B) polymerizable monomers, (C) photopolymerization initiator, (D) a cyclization catalyst, and (E) Solvent.

2. The photosensitive resin composition according to claim 1, wherein the component (A) is a polyimide precursor having a structural unit represented by the following formula (1): In formula (1), X1 is a tetravalent group having one or more aromatic groups, the -COOR1 group and the -CONH- group are ortho-positioned to each other, the -COOR2 group and the -CO- group are ortho-positioned to each other, Y1 is a divalent aromatic group, R1 and R2 are each independently a hydrogen atom, a group represented by the following formula (2), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R1 and R2 is a group represented by the above formula (2). In formula (2), R3 to R5 are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and m is an integer of 1 to 10. 3 . The photosensitive resin composition according to claim 1 , wherein the component (D) is at least one selected from the group consisting of N-phenyldiethanolamine, N-methylaniline, N-ethylaniline, N,N-dimethylaniline, N-phenylethanolamine, 4-phenylmorpholine, and 2,2′-(4-methylphenylimino)diethanol.

4. The photosensitive resin composition according to claim 1 or 2, wherein the component (D) comprises a compound represented by the following formula (17): In formula (17), R 31A ~R 33A are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group, a monovalent aliphatic hydrocarbon group having a hydroxyl group, or a monovalent aromatic group, and R 31A ~R 33A At least one of is a monovalent aromatic group, R 31A ~R 33A Adjacent groups may form a ring with each other.

5. The photosensitive resin composition according to any one of claims 1 to 4, wherein the component (C) comprises (C1) a compound represented by the following formula (15) and (C2) a compound represented by the following formula (16). In formula (15), R 11A is an alkyl group having 1 to 12 carbon atoms, a1 is an integer from 0 to 5, R 12A is a hydrogen atom or an alkyl group with 1 to 12 carbon atoms, R 13A and R 14A Each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a phenyl group or a tolyl group, and when a1 is an integer greater than or equal to 2, R 11A They can be the same or different. In formula (16), R 21A is an alkyl group with 1 to 12 carbon atoms, R 22A and R 23A are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group, wherein c1 is an integer of 0 to 5. When c1 is an integer greater than or equal to 2, R 21A They can be the same or different. 6 . The photosensitive resin composition according to claim 1 , wherein the component (B) comprises a polymerizable monomer having an aliphatic cyclic skeleton. 7 . The photosensitive resin composition according to claim 1 , wherein the component (B) has a group containing a polymerizable unsaturated double bond. 8 . The photosensitive resin composition according to claim 7 , wherein the component (B) is a polymerizable monomer having a group containing two or more polymerizable unsaturated double bonds.

9. The photosensitive resin composition according to any one of claims 1 to 7, wherein the component (B) comprises a polymerizable monomer represented by the following formula (3): In formula (3), R6 and R7 are each independently an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a group represented by the following formula (4), n1 is 0 or 1, n2 is an integer from 0 to 2, n1+n2 is greater than or equal to 1, and at least one of n1 R6 and n2 R7 is a group represented by the following formula (4), In formula (4), R9~R 11 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and l represents an integer of 0 to 10. 10 . The photosensitive resin composition according to claim 9 , wherein n1+n2 is 2 or 3.

11. The photosensitive resin composition according to any one of claims 1 to 10, wherein the component (B) comprises a polymerizable monomer represented by the following formula (5): 12 . The photosensitive resin composition according to claim 1 , further comprising (F) a thermal polymerization initiator. 13 . The photosensitive resin composition according to claim 1 , further comprising an antioxidant.

14. A method for producing a patterned cured product, comprising the following steps: A step of applying the photosensitive resin composition according to any one of claims 1 to 13 on a substrate and drying the resulting film to form a photosensitive resin film; The process of pattern-exposing the photosensitive resin film to obtain a resin film; The process of developing the resin film after the pattern exposure using an organic solvent to obtain a patterned resin film; as well as a step of heating the patterned resin film. 15 . The method for producing a patterned cured product according to claim 14 , wherein the temperature of the heat treatment is less than or equal to 230° C. 16 . A cured product obtained by curing the photosensitive resin composition according to claim 1 . The cured product according to claim 16 , which is a patterned cured product.

18. An interlayer insulating film, a cover coat or a surface protective film produced using the cured product according to claim 16 or 17. 19 . An electronic component comprising the interlayer insulating film, cover coat or surface protection film according to claim 18 .

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