Photosensitive resin composition, resin film, and semiconductor device

Abstract

To provide a photosensitive resin composition that can form a coating film with excellent adhesion to a semiconductor substrate and has good storage stability, a resin film with high reliability and patterning accuracy, and a semiconductor device containing such a resin film. [Solution] The photosensitive resin composition according to the present invention is a photosensitive resin composition used in the manufacture of a resin film for a semiconductor device, and comprises a phenol resin (A), a crosslinking agent (B), an acid generator (C), and an adhesion aid (D), wherein the adhesion aid (D) comprises a heterocyclic aromatic compound containing an amino group and a nitrogen atom as a heteroatom constituting the ring, and a coupling agent containing an amino group.

Description

[Technical Field]

[0001] The present invention relates to a photosensitive resin composition, a resin film, and a semiconductor device. [Background technology]

[0002] The redistribution layer of a semiconductor device comprises an insulating layer and a wiring layer. Of these, the insulating layer is formed using a photosensitive resin composition and patterned into a desired shape.

[0003] For example, Patent Document 1 discloses a photosensitive resin composition containing an alkaline aqueous solution-soluble resin, a crosslinking agent, a photopolymerization initiator, and an epoxy resin (thermosetting resin). It is disclosed that by using this photosensitive resin composition, a cured product with excellent flexibility, adhesion, pencil hardness, solvent resistance, acid resistance, heat resistance, and gold plating resistance can be obtained. It is also disclosed that this cured product can be used as an interlayer insulating material for electronic components. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2016-80871 [Overview of the project] [Problems that the invention aims to solve]

[0005] With the increasing sophistication of electronic devices, there is a growing demand for higher reliability and higher density of redistribution layers. Achieving high reliability requires suppressing unintended peeling of the coating film made from a photosensitive resin composition when exposed to light and developed. Furthermore, achieving higher density necessitates improving the photosensitivity of the photosensitive resin composition, but this sensitivity can deteriorate depending on the storage conditions. Therefore, improving the storage stability of the photosensitive resin composition is a key challenge.

[0006] The object of the present invention is to provide a photosensitive resin composition that can form a coating film with excellent adhesion to a semiconductor substrate and has good storage stability, a resin film with high reliability and patterning accuracy, and a semiconductor device containing such a resin film. [Means for solving the problem]

[0007] These objectives are achieved by the present invention as described in (1) to (13) below. (1) A photosensitive resin composition used in the manufacture of a resin film for a semiconductor device, Phenolic resin (A) and, Crosslinking agent (B), Acid generator (C), Adhesion aid (D), Includes, The aforementioned adhesion aid (D) is A heterocyclic aromatic compound containing an amino group and a nitrogen atom as a heteroatom constituting the ring, A coupling agent containing an amino group, A photosensitive resin composition characterized by containing the following.

[0008] (2) The photosensitive resin composition according to (1) above, wherein the adhesion aid (D) further comprises a coupling agent containing an epoxy group.

[0009] (3) The acid generator (C) is the photosensitive resin composition according to (1) or (2) above, comprising a thermal acid generator and a photoacid generator.

[0010] (4) The photosensitive resin composition according to any one of (1) to (3) above, wherein the crosslinking agent (B) comprises a first component that is solid at room temperature and a second component that is liquid at room temperature.

[0011] (5) The photosensitive resin composition according to (4) above, wherein the first component comprises a urea-based compound and an epoxy-based compound.

[0012] (6) The photosensitive resin composition according to (5) above, wherein the epoxy compound contained in the first component contains an aromatic ring.

[0013] (7) The photosensitive resin composition according to (5) or (6) above, wherein the number of functional groups of the epoxy compound contained in the first component is 3 or more.

[0014] (8) The photosensitive resin composition according to any one of (4) to (7) above, wherein the second component contains a bifunctional phenoxy type epoxy resin.

[0015] (9) The photosensitive resin composition according to any one of (1) to (8) above, wherein the average number of functional groups of the crosslinking agent (B) is 2.4 or more and 3.6 or less.

[0016] (10) The photosensitive resin composition according to any one of (1) to (9) above, wherein the mixing ratio D1 / D2 of the heterocyclic aromatic compound to the coupling agent is 0.01 or more and 0.70 or less by mass ratio.

[0017] (11) The photosensitive resin composition according to any one of (1) to (10) above, wherein the phenol resin (A) is a biphenyl type phenol resin.

[0018] (12) A resin film characterized by being composed of a cured product of the photosensitive resin composition according to any one of (1) to (11) above.

[0019] (13) A semiconductor device, comprising: the resin film according to (12) above provided on the surface of the semiconductor element; and characterized by comprising the same.

Advantages of the Invention

[0020] According to the present invention, a photosensitive resin composition capable of forming a coating film excellent in adhesion to a semiconductor substrate and having good storage stability can be obtained.

[0021] Furthermore, according to the present invention, a resin film with high reliability and patterning accuracy can be obtained. Furthermore, according to the present invention, a semiconductor device containing the above-mentioned resin film can be obtained. [Brief explanation of the drawing]

[0022] [Figure 1] This is a cross-sectional view showing an example of a trench pattern formed using a photosensitive resin composition. [Figure 2] This is a cross-sectional view showing a semiconductor device (semiconductor device according to the embodiment) equipped with a resin film according to the embodiment. [Modes for carrying out the invention]

[0023] The photosensitive resin composition, resin film, and semiconductor device according to the present invention will be described in detail below based on preferred embodiments shown in the accompanying drawings.

[0024] 1. Photosensitive resin composition The photosensitive resin composition according to this embodiment is a resin material used to manufacture a resin film for a semiconductor device. This photosensitive resin composition comprises a phenolic resin (A), a crosslinking agent (B), an acid generator (C), and an adhesion aid (D). The adhesion aid (D) comprises a heterocyclic aromatic compound (D1) and an amino group-containing coupling agent (D2). The heterocyclic aromatic compound (D1) contains an amino group and a nitrogen atom as a heteroatom constituting the ring.

[0025] This configuration enables the formation of a coating film with excellent adhesion to a semiconductor substrate and realizes a photosensitive resin composition with good storage stability. Therefore, this photosensitive resin composition exhibits excellent photosensitivity even after storage, and the resin film produced using this photosensitive resin composition is less likely to peel off from the semiconductor substrate. Thus, by using the photosensitive resin composition according to this embodiment, a resin film with high reliability and patterning accuracy can be manufactured. As a result, for example, a redistribution layer with improved reliability and high resolution can be realized, improving resistance to temperature cycle tests and improving the wiring density of the redistribution layer.

[0026] 1.1. Phenolic resin (A) Examples of phenolic resin (A) include phenol novolac resin, naphthalene ring-containing phenolic resin, aralkyl-type phenolic resin, triphenolalkane-type phenolic resin, biphenyl-type phenolic resin, alicyclic phenolic resin, heterocyclic phenolic resin, naphthalene ring-containing phenolic resin, bisphenol-type phenolic resin, etc., and one or a mixture of two or more of these is used.

[0027] Of these, biphenyl-type phenolic resin (A1) is preferably used as the phenolic resin (A). Biphenyl-type phenolic resin (A1) is a phenolic resin having a biphenyl structure. As the biphenyl-type phenolic resin, a phenolic resin having a structural unit represented by the following formula (1) is preferably used. This makes it possible to improve the low-temperature curability of the photosensitive resin composition, the reliability of the resin film, and the storage stability of the photosensitive resin composition. Furthermore, with the improvement in low-temperature curability, the taper angle of the end face in the trench pattern can be increased. This makes it possible to increase the resolution of the trench pattern, and for example, it becomes possible to improve the wiring density of the redistribution layer.

[0028] [ka]

[0029] In the above equation (1), R41 and R 42 Each of these is independently a monovalent substituent selected from the group consisting of a hydroxyl group, a halogen atom, a carboxyl group, a saturated or unsaturated alkyl group having 1 to 20 carbon atoms, an alkyl ether group having 1 to 20 carbon atoms, a saturated or unsaturated alicyclic group having 3 to 20 carbon atoms, or an organic group having an aromatic structure having 6 to 20 carbon atoms, and these may be linked via ester, ether, amide, or carbonyl bonds. Furthermore, r and s are independently integers from 0 to 3. In addition, Y4 and Z4 are independently selected from the group consisting of an aliphatic group having 1 to 10 carbon atoms, a alicyclic group having 3 to 20 carbon atoms, and an organic group having an aromatic structure having 6 to 20 carbon atoms, which may have single or unsaturated bonds. Note that Z4 is bonded to one of the two benzene rings.

[0030] Furthermore, in the structural unit represented by formula (1) above, a hydroxyl group is bonded to the biphenyl structure. Although the detailed mechanism of action is unknown, it is thought that this hydroxyl group contributes to improving the adhesion of the coating film to the semiconductor substrate, as well as increasing the taper angle of the end face in the trench pattern.

[0031] A biphenyl-type phenolic resin (A1) having the structural unit represented by the above formula (1) can be obtained, for example, by the method described in Japanese Patent Application Publication No. 2018-155938.

[0032] The weight-average molecular weight of the biphenyl-type phenolic resin (A1) is preferably 12,000 or more, more preferably 15,000 or more, and even more preferably 20,000 or more. This enhances the curability of the photosensitive resin composition and improves the elongation and storage stability of the resin film. Furthermore, the weight-average molecular weight of the biphenyl-type phenolic resin (A1) is preferably 500,000 or less, more preferably 400,000 or less, and even more preferably 200,000 or less. This ensures appropriate solubility of the photosensitive resin composition in the solvent.

[0033] The content of biphenyl-type phenolic resin (A1) in the photosensitive resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, based on the total solids of the photosensitive resin composition. This enhances the curability of the photosensitive resin composition. Furthermore, the content of biphenyl-type phenolic resin (A1) in the photosensitive resin composition is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less, based on the total solids of the photosensitive resin composition. This suppresses a decrease in the elongation of the resin film.

[0034] Furthermore, from the viewpoint of obtaining a photosensitive resin composition with excellent low-temperature curing properties, it is preferable to include a biphenyl-type phenolic resin (A2) having a structure represented by the following formula (2). By including such a biphenyl-type phenolic resin (A2), the curability of the photosensitive resin composition, the elongation of the resin film, and the storage stability can be further improved. In addition, the improved low-temperature curability allows for a further increase in the taper angle of the end faces in the trench pattern.

[0035] [ka]

[0036] In formula (2) above, n is preferably 6 or more, more preferably 10 or more, and even more preferably 14 or more. This further improves the curability of the photosensitive resin composition, the elongation of the resin film, and the storage stability. In addition, the improved curability at low temperatures allows for a further increase in the taper angle of the end faces in the trench pattern.

[0037] Furthermore, from the viewpoint of solvent solubility, n is preferably 72 or less, more preferably 54 or less, and even more preferably 36 or less.

[0038] The weight-average molecular weight of the biphenyl-type phenolic resin (A2) is preferably 500 or more, more preferably 2,000 or more, and even more preferably 4,000 or more. This enhances curability, elongation of the resin film, and storage stability. Furthermore, the weight-average molecular weight of the biphenyl-type phenolic resin (A2) is preferably 50,000 or less, more preferably 20,000 or less, and even more preferably 10,000 or less. This ensures appropriate solubility in the solvent.

[0039] When the photosensitive resin composition contains biphenyl-type phenolic resin (A2), the content of biphenyl-type phenolic resin (A2) is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, of the total solids of the photosensitive resin composition. This ensures good curability. Furthermore, the content of biphenyl-type phenolic resin (A2) in the photosensitive resin composition is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less, of the total solids of the photosensitive resin composition. This suppresses a decrease in the elongation of the resin film.

[0040] In the photosensitive resin composition, the above-mentioned biphenyl-type phenolic resin (A1) and biphenyl-type phenolic resin (A2) may be used in combination. In this case, the total content of biphenyl-type phenolic resin (A1) and biphenyl-type phenolic resin (A2) is preferably 30% by mass or more, more preferably 45% by mass or more, and even more preferably 55% by mass or more, of the total solid content of the photosensitive resin composition, particularly from the viewpoint of improving curability at low temperatures, reliability of the resin film, storage stability, and the taper angle of the end face in the trench pattern. Furthermore, the total content of biphenyl-type phenolic resin (A1) and biphenyl-type phenolic resin (A2) in the photosensitive resin composition is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less, of the total solid content of the photosensitive resin composition, from the viewpoint of improving photosensitivity, storage stability, and chemical resistance of the resin film.

[0041] The photosensitive resin composition may also contain thermosetting resins other than biphenyl-type phenolic resin (A1) and biphenyl-type phenolic resin (A2). Examples of such thermosetting resins include hydroxystyrene resin, polyamide resin, polybenzoxazole resin, polyimide resin, and cyclic olefin resin.

[0042] 1.2. Crosslinking agent (B) The crosslinking agent (B) can impart deformation resistance to the resin film through a crosslinking reaction, contributing to improved patterning accuracy.

[0043] The crosslinking agent (B) is not particularly limited, but preferably comprises a first component (B1) that is solid at room temperature and a second component (B2) that is liquid at room temperature. By including both a first component (B1) and a second component (B2) in the crosslinking agent (B), it is possible to achieve both deformation resistance and crosslinking reactivity in the photosensitive coating formed using the photosensitive resin composition. This makes it possible to realize a photosensitive resin composition that can produce a resin film with a sufficiently large tensile elongation of the cured product and a sufficiently large taper angle of the end face when a trench pattern is formed. Therefore, by using such a photosensitive resin composition, it becomes possible to manufacture a resin film that has excellent resistance to brittle fracture and high patterning accuracy. In this specification, "room temperature" refers to 23°C.

[0044] The first component (B1) primarily contributes to improving the deformation resistance of the photosensitive film formed using the photosensitive resin composition by suppressing its fluidity. By improving the deformation resistance of the photosensitive film, for example, when patterning the photosensitive film into a shape including a trench pattern, deformation of the photosensitive film can be suppressed, making it possible to realize a photosensitive resin composition that can produce a resin film with a sufficiently large taper angle on the end face facing the trench.

[0045] Examples of the first component (B1) include urea compounds, epoxy compounds, melamine compounds, cyano compounds, isocyanate compounds, maleimide compounds, benzoguanamine compounds, and metal chelating agents. Furthermore, the first component (B1) may be a mixture of two or more compounds.

[0046] Of these, the first component (B1) preferably contains a urea-based compound or an epoxy-based compound. This particularly enhances the deformation resistance of the photosensitive coating.

[0047] The second component (B2) primarily contributes to improving the crosslinking reactivity of the photosensitive film formed using the photosensitive resin composition. By improving the crosslinking reactivity of the photosensitive film, for example, when patterning the photosensitive film into a shape including a trench pattern, crosslinking within the photosensitive film is promoted. This makes it easier to maintain the shape immediately after patterning. As a result, a photosensitive resin composition can be realized that can produce a resin film with a sufficiently large taper angle on the end face facing the trench. Furthermore, the improved crosslinking reactivity can contribute to improving the tensile elongation of the resin film. Moreover, a photosensitive resin composition can be realized that can produce a resin film with excellent mechanical properties even when subjected to low-temperature curing at, for example, around 200°C.

[0048] Examples of the second component (B2) include urea compounds, epoxy compounds, melamine compounds, cyano compounds, isocyanate compounds, maleimide compounds, benzoguanamine compounds, and metal chelating agents. Furthermore, the second component (B2) may be a mixture of two or more compounds.

[0049] Of these, the second component (B2) preferably contains a urea-based compound or an epoxy-based compound, and more preferably both. This particularly enhances the crosslinking reactivity of the photosensitive coating.

[0050] 1.2.1.Urea compounds The urea-based compound used as the crosslinking agent (B) is a urea compound that has an average of two or more functional groups contributing to crosslinking in one molecule. The urea compound is a compound containing a urea structure (-NC(=O)N-). Examples of functional groups include methylol groups and alkoxyalkyl groups.

[0051] Specific examples of urea compounds include difunctional urea compounds having an average of two functional groups, and polyfunctional urea compounds having an average of three or more functional groups.

[0052] Examples of bifunctional urea compounds include glycoluryl compounds such as dihydroxymethylated glycoluryl, dimethoxymethylated glycoluryl, diethoxymethylated glycoluryl, dipropoxymethylated glycoluryl, and dibutoxymethylated glycoluryl; urea compounds such as bismethoxymethylurea, bisethoxymethylurea, bispropoxymethylurea, and bisbutoxymethylurea; dihydroxymethylated ethyleneurea, dimethoxymethylated ethyleneurea, diethoxymethylated ethyleneurea, and dipropoxy Examples include ethyleneurea compounds such as dimethylated ethyleneurea and dibutoxymethylated ethyleneurea, propyleneurea compounds such as dihydroxymethylated propyleneurea, dimethoxymethylated propyleneurea, diethoxymethylated propyleneurea, dipropoxymethylated propyleneurea, and dibutoxymethylated propyleneurea, and imidazolidinone compounds such as 1,3-di(methoxymethyl)-4,5-dihydroxy-2-imidazolidinone and 1,3-di(methoxymethyl)-4,5-dimethoxy-2-imidazolidinone.

[0053] Examples of polyfunctional urea compounds include trifunctional urea compounds such as trihydroxymethylated glycoluryl, trimethoxymethylated glycoluryl, triethoxymethylated glycoluryl, trippropoxymethylated glycoluryl, and tripbutoxymethylated glycoluryl, and tetrafunctional urea compounds such as tetrahydroxymethylated glycoluryl, tetramethoxymethylated glycoluryl, tetraethoxymethylated glycoluryl, tetrapropoxymethylated glycoluryl, and tetrabutoxymethylated glycoluryl.

[0054] The urea-based compound contained in the first component (B1) is preferably a polyfunctional urea compound, and more preferably a tetrafunctional urea compound. Polyfunctional urea compounds have a relatively large number of crosslinking points. Therefore, it is possible to produce a cured product with good mechanical properties. As a result, a resin film with good resistance to brittle fracture due to temperature changes and the like can be obtained.

[0055] In particular, a bifunctional urea compound is preferably used as the urea-based compound contained in the second component (B2). Bifunctional urea compounds have a relatively small number of crosslinking points. Therefore, it is possible to realize a photosensitive resin composition that can produce a resin film with high elongation.

[0056] Furthermore, the crosslinking agent (B) may contain both a bifunctional urea compound and a polyfunctional urea compound. This makes it possible to create a photosensitive resin composition that can produce a resin film that has both excellent resistance to, for example, temperature cycling tests and high elongation.

[0057] 1.2.2. Epoxy Compounds The epoxy compound used as a crosslinking agent (B) is an epoxy compound (epoxy resin) that has an average of two or more epoxy groups contributing to crosslinking in one molecule.

[0058] Specific examples of epoxy compounds include bifunctional epoxy compounds having an average of two epoxy groups, and polyfunctional epoxy compounds having an average of three or more epoxy groups.

[0059] While the bifunctional epoxy compound is not particularly limited as long as it is a bifunctional epoxy compound, it is preferable to use a bifunctional phenoxy-type epoxy resin. This makes it easier to create longer molecular chains, which imparts high flexibility to the resin film. As a result, a resin film with particularly high elongation can be obtained. In addition, because it contains aromatic rings, the mechanical properties (such as tensile strength) of the resin film can be enhanced.

[0060] Examples of bifunctional phenoxy epoxy resins include bisphenol A type phenoxy resin, bisphenol F type phenoxy resin, bisphenol S type phenoxy resin, bisphenolacetophenone type phenoxy resin, novolac type phenoxy resin, biphenyl type phenoxy resin, fluorene type phenoxy resin, dicyclopentadiene type phenoxy resin, norbornene type phenoxy resin, naphthalene type phenoxy resin, anthracene type phenoxy resin, adamantane type phenoxy resin, terpene type phenoxy resin, and trimethylcyclohexane type phenoxy resin.

[0061] Specific examples of bifunctional epoxy compounds include EXA-4850-150, EXA-4816, EXA-4822 from DIC Corporation; EP-4000S, EP-4000SS, EP-4003S, EP-4010S, EP-4011S from ADEKA Corporation; BEO-60E, BPO-20E from Shin Nippon Rika Co., Ltd.; YX-7105, YX-7110, YX-7400, YX-7180 ​​from Mitsubishi Chemical Corporation; and LX-01 from Osaka Soda Co., Ltd.

[0062] The polyfunctional epoxy compound is not particularly limited as long as it is a polyfunctional epoxy compound (having three or more functional groups).

[0063] Specific examples of polyfunctional epoxy compounds include Epicote 180 and Epicote 157 from Mitsubishi Chemical Corporation; UVR-6610, UVR-6620, and UVR-6650 from Union Carbide Corporation; TACT1X742 from Dow Chemical Corporation; and Techmore VG3101L from Printec Corporation.

[0064] The epoxy compound included in the first component (B1) may be a polyfunctional epoxy compound, and a trifunctional epoxy compound is particularly preferred. Polyfunctional epoxy compounds have a relatively large number of crosslinking points. Therefore, it is possible to produce a cured product with good mechanical properties. In particular, trifunctional epoxy compounds possess both a large number of crosslinking points and flexibility of molecular chains. Therefore, a resin film that balances good mechanical properties and high elongation can be obtained. As a result, a resin film with particularly good resistance to brittle fracture due to temperature changes and the like can be obtained.

[0065] The epoxy compound included in the second component (B2) is preferably a bifunctional epoxy compound. Bifunctional epoxy compounds have a relatively small number of crosslinking points. Therefore, it is possible to realize a photosensitive resin composition that can produce a resin film with high elongation.

[0066] Furthermore, the crosslinking agent (B) may contain both a bifunctional epoxy compound and a polyfunctional epoxy compound. This results in a resin film that combines a flexible structure derived from the bifunctional epoxy compound with a rigid structure derived from the polyfunctional epoxy compound. As a result, even when subjected to temperature cycling tests, for example, a resin film is obtained that achieves a particularly high degree of balance between good mechanical properties (breaking strength) and high elongation. Examples of flexible structures include structures dominated by aliphatic hydrocarbons, such as alkylene groups with 1 to 8 carbon atoms, ethylene glycol groups, propylene glycol groups, and butylene glycol groups. On the other hand, examples of rigid structures include structures containing aromatic rings, such as condensed aromatic ring structures like benzene rings, naphthalene rings, anthracene rings, and pyrene rings; aromatic ring structures like biphenyl rings, cardo structures, and fluorene rings; and heterocyclic structures like pyrrole rings and thiophene rings.

[0067] Based on the above, it is preferable that the epoxy compound included in the first component (B1) contains an aromatic ring. With such a configuration, a rigid structure with stable properties derived from the aromatic ring is formed in the resin film, while a flexible structure is easily formed between the aromatic ring and the epoxy group. As a result, a resin film that achieves both good mechanical properties and high elongation can be obtained.

[0068] 1.2.3.Containing amount The content of the first component (B1) is preferably 5 parts by mass or more, more preferably 15 parts by mass or more, and even more preferably 25 parts by mass or more, when the content of the phenol resin (A) is 100 parts by mass. This makes it possible to sufficiently increase the deformation resistance of the photosensitive coating and to produce a resin film with a sufficiently large taper angle at the end face. Furthermore, the content of the first component (B1) is preferably 60 parts by mass or less, more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less, when the content of the phenol resin (A) is 100 parts by mass. This makes it possible to suppress a decrease in the shape-following ability of the photosensitive coating.

[0069] The content of the second component (B2) is preferably 3 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more, when the content of phenol resin (A) is 100 parts by mass. This sufficiently increases the crosslinking reactivity of the photosensitive coating and makes it possible to produce a resin film with a sufficiently large taper angle at the end face. Furthermore, the content of the second component (B2) is preferably 60 parts by mass or less, more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less, when the content of phenol resin (A) is 100 parts by mass. This suppresses a decrease in the patterning accuracy of the photosensitive coating.

[0070] The content of the first component (B1) may be less than or equal to the content of the second component (B2), but it is preferably set to be greater than the content of the second component (B2). In other words, the ratio of the content of the first component (B1) to the content of the second component (B2) (mixing ratio B1 / B2) is preferably greater than 1.0 by mass. Furthermore, the mixing ratio B1 / B2 is more preferably between 1.5 and 8.0, and even more preferably between 2.0 and 4.0. If the mixing ratio B1 / B2 is within the above range, the balance between the content of the first component (B1) and the second component (B2) is optimized. This makes it possible to achieve a good balance between the deformation resistance and crosslinking reactivity of the photosensitive coating. As a result, it is possible to manufacture a resin film in which the tensile elongation of the cured product is sufficiently large, and the taper angle of the end face when a trench pattern is formed is also sufficiently large.

[0071] The total content of urea-based compounds and epoxy-based compounds in the photosensitive resin composition is preferably 30 parts by mass or more and 90 parts by mass or less, more preferably 40 parts by mass or more and 80 parts by mass or less, and even more preferably 50 parts by mass or more and 70 parts by mass or less, when the content of phenol resin (A) is 100 parts by mass. This ensures a more reliable balance between the deformation resistance and crosslinking reactivity of the photosensitive coating.

[0072] Furthermore, while the mixing ratio of the urea-based compound and the epoxy-based compound in the first component (B1) is not particularly limited, it is preferable that the mass ratio of the urea-based compound to the epoxy-based compound be 1.0 or higher, more preferably 1.5 to 6.0, and even more preferably 2.0 to 5.0. This optimizes the balance of each compound in the first component (B1), making it possible to produce a resin film with a particularly large taper angle at the end face when a trench pattern is formed.

[0073] 1.2.4.Number of functional groups The average number of functional groups per molecule of the crosslinking agent (B) is preferably 2.4 to 3.6, more preferably 2.8 to 3.5, and even more preferably 3.0 to 3.4. This makes it possible to achieve both high elongation, high tensile strength, and a high glass transition temperature in the cured product of the photosensitive resin composition.

[0074] Furthermore, if the average number of functional groups falls below the lower limit, the mechanical strength, such as fracture strength, of the cured product may decrease, or the heat resistance corresponding to the glass transition temperature may decrease. On the other hand, if the average number of functional groups exceeds the upper limit, the elongation of the cured product may decrease.

[0075] The average number of functional groups per molecule can be calculated based on the number of functional groups and their respective proportions in the crosslinking agent (B). For example, if a bifunctional compound and a tetrafunctional compound are blended in equal amounts, the average number of functional groups will be 3.

[0076] 1.3. Acid Generator (C) The acid generator (C) generates acid by absorbing thermal or light energy. By including the acid generator, a photosensitive resin composition capable of stably forming cured products can be obtained. Examples of this acid generator include a thermal acid generator (C1) that generates acid with thermal energy, and a photoacid generator (C2) that generates acid with light energy, and one or both of these can be used.

[0077] A sulfonium compound or a salt thereof is preferably used as the thermal acid generator (C1).

[0078] The sulfonium compound or its salt is specifically a sulfonium salt having a sulfonium ion as the cation. The anionic portion of the sulfonium compound or its salt is specifically a sulfonic acid ion such as a boride ion, antimony ion, phosphorus ion, or trifluoromethanesulfonate ion, and is preferably a boride ion or antimony ion, and more preferably a boride ion, from the viewpoint of improving the reaction rate at low temperatures. These anions may have substituents.

[0079] The sulfonium compound or its salt preferably includes a sulfonium salt represented by the following formula (4).

[0080] [ka]

[0081] In the above equation (4), R 1 is a hydrogen atom or a monovalent organic group, preferably a hydrogen atom or an acyl group, more preferably an acyl group, and even more preferably a CH3C(=O)- group.

[0082] R 2 The compound is a monovalent organic group, preferably a hydrocarbon group having a chain or branched chain, or a benzyl group which may have substituents, more preferably a benzyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, and even more preferably a benzyl group in which a methyl group or an aromatic ring portion which may be substituted with a methyl group.

[0083] R 3 The group is a monovalent organic group, and from the viewpoint of improving reactivity at low temperatures, it is preferably a hydrocarbon group having a chain or branched chain, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0084] Examples of the thermal acid generator (C1) include triphenylsulfonium salts such as triphenylsulfonium trifluoromethanesulfonate.

[0085] Examples of photoacid generators (C2) include naphthoquinone diazide compounds, diarylsulfonium salts, triarylsulfonium salts, dialkylphenacylsulfonium salts, diaryliodonium salts, aryldiazonium salts, aromatic tetracarboxylic acid esters, aromatic sulfonic acid esters, nitrobenzyl esters, aromatic N-oxyimide sulfonates, aromatic sulfamides, and benzoquinone diazosulfonic acid esters. Among these, naphthoquinone diazide compounds are preferred.

[0086] Examples of naphthoquinone diazide compounds that can be used include naphthoquinone diazide adducts of tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene and naphthoquinone diazide adducts of tetrahydroxybenzophenone. Here, the addition of naphthoquinone diazide can be produced, for example, by reacting o-quinone diazide sulfonyl chlorides with hydroxy compounds or amino compounds.

[0087] Furthermore, the photosensitive resin composition can be made positive or negative by selecting the photoacid generator (C2). Specifically, when a photoacid generator (C2) that generates acid in the exposed area is used, the solubility of the exposed area in a developer solution such as an alkaline aqueous solution increases. As a result, a positive-type photosensitive resin composition is obtained. On the other hand, when a photoacid generator (C2) that causes insolubilization upon exposure is used, the solubility of the exposed area in a developer solution decreases. As a result, a negative-type photosensitive resin composition is obtained.

[0088] From the viewpoint of improving curability, the content of the acid generator (C) in the photosensitive resin composition is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more, when the content of the phenolic resin (A) is 100 parts by mass. Furthermore, from the viewpoint of ensuring storage stability and suppressing a decrease in the reliability of the resin film, the content of the acid generator (C) in the photosensitive resin composition is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less, when the content of the phenolic resin (A) is 100 parts by mass.

[0089] The acid generator (C) is preferably composed of both a thermal acid generator (C1) and a photoacid generator (C2). This improves storage stability and increases the mechanical strength of the cured product of the photosensitive resin composition. When the acid generator (C) is composed of both a thermal acid generator (C1) and a photoacid generator (C2), the total content of these two components is the content of the acid generator (C) as described above.

[0090] The ratio of the photoacid generator (C2) to the thermal acid generator (C1) (combination ratio C2 / C1) is preferably 1 / 9 to 9 / 1 by mass, and more preferably 5 / 5 to 9 / 1. This allows for increased elongation without impairing the mechanical strength of the cured product. Furthermore, it particularly enhances the storage stability of the photosensitive resin composition.

[0091] 1.4. Adhesion enhancer (D) The photosensitive resin composition contains an adhesion enhancer (D). This further improves the adhesion between the cured product of the photosensitive resin composition and the semiconductor substrate.

[0092] As mentioned above, the adhesion aid (D) includes a heterocyclic aromatic compound (D1) and an amino group-containing coupling agent (D2).

[0093] 1.4.1. Heterocyclic aromatic compounds (D1) Heterocyclic aromatic compounds (D1) contain an amino group and a nitrogen atom as a heteroatom constituting the ring.

[0094] Examples of heterocyclic aromatic compounds (D1) include the compound represented by the following formula (7).

[0095] [ka]

[0096] In equation (7) above, R 51 R represents a hydrogen atom or a hydrocarbon group. 52 represents an amino group. A and B independently represent a nitrogen atom or a carbon atom and a hydrogen atom bonded to it (CH).

[0097] The compound represented by formula (7) above is selected from the viewpoint of improving adhesion to the semiconductor substrate, and R in formula (7) above 51 Preferably, it is a hydrogen atom.

[0098] Examples of such heterocyclic aromatic compounds (D1) include compounds having one or more functional groups selected from the group consisting of 1-(5-1H-triazol-5-yl)methylamino group, 3-(1H-pyrazoyl)amino group, 4-(1H-pyrazoyl)amino group, 5-(1H-pyrazoyl)amino group, 1-(3-1H-pyrazoyl)methylamino group, 1-(4-1H-pyrazoyl)methylamino group, 1-(5-1H-pyrazoyl)methylamino group, (1H-tetrazol-5-yl)amino group, 1-(1H-tetrazol-5-yl)methylamino group, and 3-(1H-tetrazol-5-yl)benzamino group. By including such heterocyclic aromatic compounds (D1), the number of lone pairs in the photosensitive resin composition can be increased. This improves the wettability between the photosensitive resin composition after pre-baking and post-baking and metals such as Cu and Al.

[0099] Specific examples of heterocyclic aromatic compounds (D1) include 1H-tetrazole, 5-aminotetrazole, 5-phenyltetrazole, and 5-methyltetrazole. Of these, 5-aminotetrazole is preferred from the viewpoint of improving the adhesion between the resin film formed using the photosensitive resin composition and the semiconductor substrate, and from the viewpoint of improving the storage stability of the photosensitive resin composition.

[0100] 1.4.2. Amino group-containing coupling agent (D2) The amino group-containing coupling agent (D2) is a coupling agent that contains an amino group and a hydrolyzable group as functional groups.

[0101] Examples of amino group-containing coupling agents (D2) include bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, and N-phenyl-γ-aminopropyltrimethoxysilane. Of these, γ-aminopropyltriethoxysilane (3-aminopropyltriethoxysilane) is preferred from the viewpoint of improving adhesion to the semiconductor substrate and enhancing the storage stability of the photosensitive resin composition.

[0102] In addition to the silane coupling agent described above, the amino group-containing coupling agent (D2) may also be an amino group-containing titanium coupling agent, an amino group-containing zirconium coupling agent, or the like.

[0103] Furthermore, examples of hydrolyzable groups contained in the amino group-containing coupling agent (D2) include alkoxy groups, acyloxy groups, aryloxy groups, aminooxy groups, amide groups, ketoxime groups, isocyanate groups, halogen atoms, and the like. Of these, alkoxy groups are preferably used as the hydrolyzable groups. Moreover, ethoxy groups are more preferably used as alkoxy groups. Ethoxy groups have a slower hydrolysis reaction rate compared to, for example, methoxy groups, while their reaction rate is faster than that of propoxy groups. For this reason, ethoxy groups are preferably used from the viewpoint of achieving both improved adhesion to semiconductor substrates and storage stability.

[0104] 1.4.3.Mixing ratio The mixing ratio of the heterocyclic aromatic compound (D1) to the amino group-containing coupling agent (D2) is not particularly limited, but the mixing ratio D1 / D2 of the heterocyclic aromatic compound (D1) to the amino group-containing coupling agent (D2) is preferably 0.01 to 0.70 by mass ratio, more preferably 0.05 to 0.60, and even more preferably 0.07 to 0.50. This optimizes the balance between the heterocyclic aromatic compound (D1) and the amino group-containing coupling agent (D2), improving the adhesion between the resin film formed using the photosensitive resin composition and the semiconductor substrate, and enhancing the storage stability of the photosensitive resin composition.

[0105] Furthermore, if the mixing ratio D1 / D2 falls below the lower limit, the adhesion between the resin film and the semiconductor substrate may decrease. On the other hand, if the mixing ratio D1 / D2 exceeds the upper limit, the adhesion between the resin film and the semiconductor substrate may decrease, or the storage stability of the photosensitive resin composition may decrease.

[0106] In the adhesion aid (D), the proportion of the heterocyclic aromatic compound (D1) and the amino group-containing coupling agent (D2) is preferably 20% by mass or more, and more preferably 30% by mass or more. This makes it possible to more reliably enjoy the above effects, namely, improved adhesion between the resin film and the semiconductor substrate, and improved storage stability of the photosensitive resin composition.

[0107] 1.4.4. Other coupling agents (D3) The adhesion aid (D) may also contain other coupling agents (D3).

[0108] Other coupling agents (D3) include, for example, epoxy group-containing coupling agents, (meth)acryloyl group-containing coupling agents, mercapto group-containing coupling agents, vinyl group-containing coupling agents, ureido group-containing coupling agents, sulfide group-containing coupling agents, and acid anhydride-containing coupling agents. In addition to silane coupling agents, other coupling agents (D3) may also include titanium coupling agents and zirconium coupling agents. When using these coupling agents, one type may be used alone, or two or more types may be used in combination.

[0109] Of these, the other coupling agent (D3) is preferably an epoxy group-containing coupling agent (a coupling agent containing epoxy groups). This further improves the adhesion between the resin film formed using the photosensitive resin composition and the semiconductor substrate, as well as the storage stability of the photosensitive resin composition. Furthermore, it is possible to obtain a photosensitive resin composition that has excellent resistance to brittle fracture and can produce a resin film with high patterning accuracy.

[0110] Examples of epoxy group-containing silane coupling agents include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and γ-glycidylpropyltrimethoxysilane.

[0111] Examples of silane coupling agents containing a (meth)acryloyl group include γ-((meth)acryloyloxypropyl)trimethoxysilane, γ-((meth)acryloyloxypropyl)methyldimethoxysilane, and γ-((meth)acryloyloxypropyl)methyldiethoxysilane.

[0112] Examples of mercapto group-containing silane coupling agents include 3-mercaptopropyltrimethoxysilane.

[0113] Examples of vinyl group-containing silane coupling agents include vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, and vinyltrimethoxysilane.

[0114] Examples of ureido group-containing silane coupling agents include 3-ureidopropyltriethoxysilane.

[0115] Examples of sulfide group-containing silane coupling agents include bis(3-(triethoxysilyl)propyl) disulfide and bis(3-(triethoxysilyl)propyl) tetrasulfide.

[0116] Examples of acid anhydride-containing silane coupling agents include 3-trimethoxysilylpropyl succinic anhydride, 3-triethoxysilylpropyl succinic anhydride, and 3-dimethylmethoxysilylpropyl succinic anhydride.

[0117] Adhesion aid (D) may contain ingredients other than those listed above. The content of the adhesion aid (D) in the photosensitive resin composition is preferably 0.3 parts by mass or more and 15 parts by mass or less, more preferably 0.4 parts by mass or more and 12 parts by mass or less, and even more preferably 0.5 parts by mass or more and 10 parts by mass or less, when the content of the phenol resin (A) is 100 parts by mass.

[0118] 1.5. Surfactants (E) The photosensitive resin composition may contain a surfactant (E). The inclusion of a surfactant (E) improves wettability during coating, resulting in a uniform coating film and resin film. Examples of surfactants (E) include fluorine-based surfactants, silicone-based surfactants, alkyl-based surfactants, and acrylic-based surfactants.

[0119] The surfactant (E) preferably contains a surfactant that includes at least one of a fluorine atom and a silicon atom. This contributes to obtaining a uniform coating film (improved coatability), improved developability, and improved adhesive strength. Such a surfactant is preferably a nonionic surfactant that includes at least one of a fluorine atom and a silicon atom. Examples of commercially available surfactants that can be used are the "MegaFac®" series from DIC Corporation, such as F-251, F-253, F-281, F-430, F-477, F-551, F-552, F-553, F-554, F-555, F-556, F-557, F-558, F-559, F-560, F-561, F-562, F-563, F-565, F-568, F-569, F-570, F-572, F- Examples include fluorine-containing oligomeric surfactants such as 574, F-575, F-576, R-40, R-40-LM, R-41, and R-94; fluorine-containing nonionic surfactants such as F-Tergent 250 and F-Tergent 251 from Neos Corporation; and silicone-based surfactants such as the SILFOAM® series (e.g., SD100TS, SD670, SD850, SD860, SD882) from Wacker Chemie. The photosensitive resin composition may use a mixture of two or more of these surfactants.

[0120] The amount of surfactant (E) in the photosensitive resin composition is preferably 0.001 parts by mass or more and 1 part by mass or less, and more preferably 0.005 parts by mass or more and 0.5 parts by mass or less, when the amount of phenol resin (A) is 100 parts by mass.

[0121] 1.6. Solvent The photosensitive resin composition preferably contains a solvent. This yields a photosensitive resin composition that has a varnish-like appearance.

[0122] The solvent is, for example, an organic solvent. The organic solvent is not particularly limited as long as it can dissolve or disperse the above-mentioned components and does not substantially react chemically with each component.

[0123] Examples of organic solvents include acetone, methyl ethyl ketone, toluene, propylene glycol methyl ethyl ether, propylene glycol dimethyl ether, propylene glycol 1-monomethyl ether 2-acetate, diethylene glycol ethyl methyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, benzyl alcohol, propylene carbonate, ethylene glycol diacetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl-n-propyl ether, butyl acetate, and γ-butyrolactone. These may be used individually or in combination.

[0124] When a solvent is used, the concentration of the non-volatile component in the photosensitive resin composition is preferably 30 to 75% by mass, more preferably 35 to 70% by mass. This range allows for sufficient dissolution or dispersion of each component. It also ensures good coatability, leading to improved flatness during spin coating, for example. Furthermore, the viscosity of the photosensitive resin composition can be appropriately controlled by adjusting the content of the non-volatile component.

[0125] 1.7. Other ingredients In addition to the components mentioned above, the photosensitive resin composition may optionally contain other components. Examples of other components include antioxidants, fillers such as silica, sensitizers, and film-forming agents.

[0126] 1.8. Physical properties of photosensitive resin compositions Next, the physical properties of the photosensitive resin composition according to this embodiment will be described.

[0127] 1.8.1. Tensile elongation The photosensitive resin composition preferably has a tensile elongation rate of the cured product of 25% or more, more preferably 35% or more, and still more preferably 45% or more. By having such a tensile elongation rate, the resistance to brittle fracture of the resin film can be enhanced. Thereby, when the resin film is used in a semiconductor device, the resistance to the temperature cycle test of the semiconductor device can be enhanced, and a highly reliable semiconductor device can be realized. From the viewpoint of obtaining the resin film more stably, the tensile elongation rate of the cured product is preferably 90% or less, and more preferably 70% or less.

[0128] The tensile elongation rate of the cured product is determined by the following method. First, the photosensitive resin composition is applied onto the upper surface of a silicon wafer using a spin coater. The thickness of the coating film is set such that the film thickness after drying becomes 10 μm. Next, the obtained coating film is pre-baked on a hot plate at 100 °C for 4 minutes to obtain a photosensitive film. Next, the obtained photosensitive film is exposed with a high-pressure mercury lamp so that the exposure amount becomes 600 mJ / cm 2 . Next, the silicon wafer having the photosensitive film is placed in a clean oven and post-baked under a nitrogen atmosphere at 220 °C for 240 minutes. Thereby, the photosensitive film is cured to obtain a resin film.

[0129] Next, a sample of 6.5 mm × 60 mm is cut out from the obtained resin film. Next, a tensile test is performed on the sample, and the tensile elongation rate is calculated from the broken distance and the initial distance. The tensile test is performed by a method conforming to JIS K 7161:2014, and the test conditions are 23 °C and a stretching speed of 5 mm / min. For the tensile testing machine, for example, a tensile testing machine Tensilon RTC-1210A manufactured by Orientec Co., Ltd. is used. Then, the test is performed on 5 samples, and the average value of the calculated tensile elongation rates is adopted as the tensile elongation rate of the cured product described above.

[0130] 1.8.2. Taper Angle of End Face FIG. 1 is a cross-sectional view showing an example of a trench pattern 22 formed using the photosensitive resin composition.

[0131] The specimen 2 shown in Figure 1 comprises a silicon wafer 21 and a trench pattern 22 formed on the upper surface 212 of the silicon wafer 21. The trench pattern 22 has a resin film 24 with a thickness of 5 μm and trenches 26 with a width of 10 μm formed in a part of the resin film 24. The angle between the upper surface 212 of the silicon wafer 21 and the end face 252 of the resin film 24 facing the trench 26 is defined as the taper angle θ of the end face 252. The taper angle θ of the end face 252 in the trench pattern 22 formed using the photosensitive resin composition is preferably 50° or more, more preferably 55° or more, and even more preferably 60° or more. By satisfying this range of taper angle θ, the photosensitive coating formed using the photosensitive resin composition has high patterning accuracy. Therefore, by using such a photosensitive coating, for example, a redistribution layer with high wiring density can be easily manufactured.

[0132] On the other hand, the upper limit of the taper angle θ is 90° or less, preferably 80° or less, and more preferably 75° or less. This allows for the stable formation of the trench pattern 22. As a result, for example, a redistribution layer with a high wiring density can be stably manufactured.

[0133] The method for forming subject 2 is as follows: First, a photosensitive resin composition is applied to the upper surface 212 of the silicon wafer 21 using a spin coater. The thickness of the applied film is set so that the film thickness after curing is 5 μm. Next, the obtained applied film is pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Next, the obtained photosensitive film is exposed to a predetermined exposure dose using a stepper equipped with a mask. The mask is provided with a pattern set so that trenches 26 with a width of 10 μm after curing are formed. If the photosensitive resin composition is positive type, light containing i-rays is used, and the exposure dose is 1000 mJ / cm². 2 If the photosensitive resin composition is negative type, use light containing the g-line and set the exposure dose to 10,000 mJ / cm². 2 Then, bake it on a hot plate at 100°C for 1 minute.

[0134] Next, a 2.38% aqueous tetramethylammonium hydroxide solution is used as the developer, and paddle development is performed twice to dissolve and remove the exposed or unexposed areas. Then, the wafer is rinsed with pure water for 10 seconds and then shaken dry. This yields a silicon wafer 21 with a patterned photosensitive coating.

[0135] Next, the silicon wafer 21 with the patterned photosensitive coating is placed in a clean oven and post-baked under a nitrogen atmosphere at 230°C for 120 minutes. This hardens the patterned photosensitive coating and obtains the trench pattern 22.

[0136] Furthermore, the method for measuring the taper angle θ is as follows: First, the obtained trench pattern 22 is cut in the thickness direction of the silicon wafer 21 and in a direction perpendicular to the extension direction of the trench 26. After polishing the cross-section, the polished surface is observed with a scanning electron microscope. The angle between the top surface 212 and the end surface 252 is measured in the observed image, and the measured value is defined as the taper angle θ. If the line of the end surface 252 is curved in the observed image, a straight line L is drawn connecting the lower end of the end surface 252 and the upper end of the end surface 252, and the angle between the top surface 212 and the straight line L is defined as the taper angle θ.

[0137] 1.8.3. Tensile breaking strength The tensile breaking strength of the cured photosensitive resin composition is preferably 100 MPa or more, more preferably 105 MPa or more, and even more preferably 110 MPa or more. Having such a tensile breaking strength can further enhance the resistance of the resin film to brittle fracture. However, from the viewpoint of obtaining a more stable resin film, the tensile breaking strength of the cured product is preferably 200 MPa or less, and more preferably 150 MPa or less.

[0138] The tensile breaking strength of a cured photosensitive resin composition can be determined by the following method. First, a photosensitive resin composition is applied to the upper surface of a silicon wafer using a spin coater. The thickness of the coated film is set so that the film thickness after drying is 10 μm. Next, the obtained coated film is pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Then, the obtained photosensitive film is exposed to a high-pressure mercury lamp at an exposure dose of 600 mJ / cm². 2 Exposure is performed to achieve the desired result. Next, the silicon wafer with the photosensitive coating is placed in a clean oven and post-baked under a nitrogen atmosphere at 220°C for 240 minutes. This hardens the photosensitive coating and yields a resin film.

[0139] Next, a 6.5 mm x 60 mm sample is cut from the obtained resin film. Then, a tensile test is performed on the sample, and the tensile elongation is calculated from the fracture distance and the initial distance. The tensile test is performed according to the method in accordance with JIS K 7161:2014, with test conditions of 23°C and a stretching speed of 5 mm / min. For the tensile testing machine, for example, the Orientec Tensilon RTC-1210A tensile testing machine is used. The test is then performed on five samples, and the average value of the stress at the fracture point is adopted as the tensile fracture strength of the cured product as described above.

[0140] 1.8.4. Glass transition temperature (Tg) The glass transition temperature (Tg) of the cured product of the photosensitive resin composition is preferably 230°C or higher, and more preferably 240°C or higher. Having such a glass transition temperature improves the deformation resistance of the resin film to temperature changes. However, from the viewpoint of obtaining a more stable resin film, the glass transition temperature of the cured product is preferably 300°C or lower, and more preferably 280°C or lower.

[0141] The glass transition temperature of the cured product of a photosensitive resin composition can be determined by the following method. First, a photosensitive resin composition is applied to the upper surface of a silicon wafer using a spin coater. The thickness of the coated film is set so that the film thickness after drying is 10 μm. Next, the obtained coated film is pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Then, the obtained photosensitive film is exposed to a high-pressure mercury lamp at an exposure dose of 600 mJ / cm². 2 Exposure is performed to achieve the desired result. Next, the silicon wafer with the photosensitive coating is placed in a clean oven and post-baked under nitrogen atmosphere at 220°C for 240 minutes. This hardens the photosensitive coating and yields a resin film. Next, an 8mm x 40mm sample is prepared from the obtained resin film. Then, dynamic viscoelasticity measurements are performed using a dynamic viscoelasticity analyzer (DMA device, TA Instruments, Q800) at a heating rate of 5°C / min and a frequency of 1Hz. The temperature at which the loss tangent tanδ, obtained from the measurement results, shows its maximum value is defined as the glass transition temperature.

[0142] 1.8.5. Coefficient of linear thermal expansion (CTE) The linear thermal expansion coefficient (CTE) of the cured photosensitive resin composition is preferably 65 ppm / K or less, and more preferably 60 ppm / K or less. Having such a linear thermal expansion coefficient ensures good adhesion of the resin film to a substrate or the like. From the viewpoint of obtaining a more stable resin film, the linear thermal expansion coefficient of the cured product is preferably 20 ppm / K or more, and more preferably 25 ppm / K or more.

[0143] The coefficient of linear thermal expansion of the cured product of a photosensitive resin composition can be determined by the following method. First, a photosensitive resin composition is applied to the upper surface of a silicon wafer using a spin coater. The thickness of the coated film is set so that the film thickness after drying is 10 μm. Next, the obtained coated film is pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Then, the obtained photosensitive film is exposed to a high-pressure mercury lamp at an exposure dose of 600 mJ / cm². 2Exposure is performed to achieve the desired result. Next, the silicon wafer with the photosensitive coating is placed in a clean oven and post-baked under nitrogen atmosphere at 220°C for 240 minutes. This hardens the photosensitive coating and yields a resin film. Next, a 5mm x 13mm sample is prepared from the obtained resin film. Then, a thermomechanical analysis (TMA) is performed in tensile mode under the conditions of a starting temperature of 30°C, a measurement temperature range of 30-440°C, and a heating rate of 10°C / min. The linear thermal expansion coefficient in the temperature range of 50-100°C is then determined from the measurement results.

[0144] 1.8.6.5% weight loss temperature (Td5) The 5% weight loss temperature (Td5) of the cured photosensitive resin composition is preferably 300°C to 400°C, and more preferably 320°C to 370°C. Having such a 5% weight loss temperature ensures the heat resistance of the resin film. This makes it possible to achieve a resin film with good resistance to, for example, temperature cycling tests.

[0145] The 5% weight loss temperature of the cured product of a photosensitive resin composition can be determined by the following method. First, a photosensitive resin composition is applied to the upper surface of a silicon wafer using a spin coater. The thickness of the coated film is set so that the film thickness after drying is 10 μm. Next, the obtained coated film is pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Then, the obtained photosensitive film is exposed to a high-pressure mercury lamp at an exposure dose of 600 mJ / cm². 2 Exposure is performed to achieve the desired result. Next, the silicon wafer with the photosensitive coating is placed in a clean oven and post-baked under nitrogen atmosphere at 220°C for 240 minutes. This hardens the photosensitive coating and yields a resin film for use as a sample. Next, the obtained sample is subjected to simultaneous thermogravimetric differential thermal analysis, and the temperature at which the weight decreases by 5% from the initial weight is determined as the 5% weight loss temperature. The measurement conditions are a nitrogen flow of 30 mL / min and a heating rate of 10°C / min.

[0146] 2. Resin film Next, the resin film according to the embodiment will be described.

[0147] A cured product is obtained by curing the photosensitive resin composition according to this embodiment. The resin film according to this embodiment is composed of this cured product. Such a resin film is used as a resin film in a semiconductor device. The resin film is used, for example, as a permanent film or a resist. Of these, it is preferably used as a permanent film from the viewpoint of reliability, such as having excellent adhesion to the semiconductor substrate, high elongation, resistance to brittle fracture, and the ability to achieve high patterning accuracy. Examples of permanent films include protective films such as buffer coat films, interlayer films such as redistribution insulating films, and dam materials.

[0148] 3. Semiconductor equipment Next, a semiconductor device according to an embodiment will be described.

[0149] Figure 2 is a cross-sectional view showing a semiconductor device (semiconductor device according to the embodiment) equipped with a resin film according to the embodiment.

[0150] The semiconductor device 100 shown in Figure 2 comprises a semiconductor element (not shown), a multilayer wiring layer including an interlayer insulating film 30 and an uppermost wiring layer 34 provided on the semiconductor element, a passivation film 32, a rewiring layer 40, a UBM layer 50, and bumps 52.

[0151] The interlayer insulating film 30 and the uppermost wiring layer 34 are located at the top of the multilayer wiring layer. The uppermost wiring layer 34 is made of a metallic material, such as Al or Cu.

[0152] The passivation film 32 is provided on the multilayer wiring layer. An opening is provided in a part of the passivation film 32, exposing the uppermost layer wiring 34.

[0153] A rewiring layer 40 is provided on the passivation film 32. The rewiring layer 40 includes an insulating layer 42 provided on the passivation film 32, rewiring 46 provided on the insulating layer 42, and an insulating layer 44 provided on the insulating layer 42 and the rewiring 46. The insulating layer 42 has an opening formed therein to connect the rewiring 46 to the uppermost wiring layer 34. The insulating layer 44 has an opening formed therein to connect the UBM layer 50 to the rewiring 46.

[0154] The bump 52 is electrically connected to the rewiring 46 via the UBM layer 50 (Under Bump Metallurgy). The semiconductor device 100 is connected to a wiring board (not shown) or the like via the bump 52.

[0155] Such a semiconductor device 100 includes the resin film described above. Specifically, in the semiconductor device 100, one or more of the resin films selected from the group consisting of a passivation film 32, an insulating layer 42, and an insulating layer 44 are used. The resin film has excellent resistance to brittle fracture and high patterning accuracy, thus enabling the realization of a semiconductor device 100 with high reliability and wiring density of the redistribution layer 40.

[0156] 4. Effects achieved by the above embodiment As described above, the photosensitive resin composition according to the embodiment is a photosensitive resin composition used in the manufacture of a resin film for a semiconductor device, and comprises a phenolic resin (A), a crosslinking agent (B), an acid generator (C), and an adhesion aid (D). The adhesion aid (D) comprises a heterocyclic aromatic compound (D1) containing an amino group and a nitrogen atom as a heteroatom constituting the ring, and a coupling agent containing an amino group (amino group-containing coupling agent (D2)).

[0157] This configuration enables the formation of a coating film with excellent adhesion to semiconductor substrates and realizes a photosensitive resin composition with good storage stability. This photosensitive resin composition exhibits excellent photosensitivity even after storage, and the resin film produced using this photosensitive resin composition exhibits suppressed peeling from semiconductor substrates. Therefore, by using the photosensitive resin composition according to this embodiment, a resin film with high reliability and patterning accuracy can be manufactured.

[0158] In the photosensitive resin composition according to the above embodiment, the adhesion aid (D) may further contain a coupling agent containing an epoxy group.

[0159] This configuration improves the adhesion between the resin film formed using the photosensitive resin composition and the semiconductor substrate, as well as the storage stability of the photosensitive resin composition. Furthermore, it provides a photosensitive resin composition that exhibits excellent resistance to brittle fracture and enables the production of resin films with high patterning accuracy.

[0160] In the photosensitive resin composition according to the above embodiment, the acid generator (C) preferably includes a thermal acid generator (C1) and a photoacid generator (C2).

[0161] This configuration enhances storage stability and increases the mechanical strength of the cured photosensitive resin composition.

[0162] In the photosensitive resin composition according to the above embodiment, the crosslinking agent (B) may include a first component (B1) that is solid at room temperature and a second component (B2) that is liquid at room temperature.

[0163] This configuration makes it possible to achieve both deformation resistance and crosslinking reactivity in the photosensitive coating formed using the photosensitive resin composition. As a result, it is possible to realize a photosensitive resin composition that can produce a resin film with a sufficiently large tensile elongation of the cured product and a sufficiently large taper angle at the end face when a trench pattern is formed.

[0164] In the photosensitive resin composition according to the above embodiment, the first component (B1) may include a urea-based compound and an epoxy-based compound. This configuration significantly enhances the deformation resistance of the photosensitive coating.

[0165] In the photosensitive resin composition according to the above embodiment, the epoxy compound contained in the first component (B1) may contain an aromatic ring.

[0166] With this configuration, a rigid structure with stable properties derived from the aromatic ring is formed in the resin film, while a flexible structure is easily formed between the aromatic ring and the epoxy group. As a result, a resin film that achieves both good mechanical properties and high elongation can be obtained.

[0167] In the photosensitive resin composition according to the above embodiment, the number of functional groups of the epoxy compound contained in the first component (B1) may be 3 or more.

[0168] This configuration results in a relatively large number of crosslinking points in the first component (B1). Therefore, a cured product with excellent mechanical properties can be produced. Furthermore, trifunctional epoxy compounds, in particular, possess both a high number of crosslinking points and the flexibility of their molecular chains. This allows for the creation of a resin film that achieves a good balance between excellent mechanical properties and high elongation. As a result, a resin film with particularly good resistance to brittle fracture due to temperature changes and other factors can be obtained.

[0169] In the photosensitive resin composition according to the above embodiment, the second component (B2) may include a bifunctional phenoxy-type epoxy resin.

[0170] This configuration allows for longer molecular chains, imparting high flexibility to the resin film. As a result, a resin film with particularly high elongation can be obtained. Furthermore, the inclusion of aromatic rings enhances the mechanical properties (such as tensile strength) of the resin film.

[0171] In the photosensitive resin composition according to the above embodiment, the average number of functional groups of the crosslinking agent (B) may be 2.4 or more and 3.6 or less.

[0172] With this configuration, it is possible to achieve both high elongation, high fracture strength, and a high glass transition temperature in the cured product.

[0173] In the photosensitive resin composition according to the above embodiment, the blending ratio D1 / D2 of the heterocyclic aromatic compound (D1) to the amino group-containing coupling agent (D2) may be 0.01 or more and 0.70 or less by mass ratio.

[0174] With this configuration, the balance between the heterocyclic aromatic compound (D1) and the amino group-containing coupling agent (D2) is optimized, improving the adhesion between the resin film formed using the photosensitive resin composition and the semiconductor substrate, and also enhancing the storage stability of the photosensitive resin composition.

[0175] In the photosensitive resin composition according to the above embodiment, the phenolic resin (A) is preferably a biphenyl-type phenolic resin.

[0176] This configuration makes it possible to improve the low-temperature curability of the photosensitive resin composition, the reliability of the resin film, and the storage stability of the photosensitive resin composition.

[0177] The resin film according to the above embodiment is composed of a cured product of the photosensitive resin composition according to the above embodiment.

[0178] With this configuration, a resin film can be obtained that is highly reliable, i.e., has excellent adhesion to the semiconductor substrate and resistance to brittle fracture, as well as high patterning accuracy.

[0179] The semiconductor device 100 according to the above embodiment comprises a semiconductor element and a resin film provided on the surface of the semiconductor element. The resin film includes the resin film according to the above embodiment.

[0180] With this configuration, the resin film exhibits excellent adhesion to the semiconductor substrate and resistance to brittle fracture, resulting in a highly reliable semiconductor device 100.

[0181] Although the photosensitive resin composition, resin film, and semiconductor device according to the present invention have been described above based on the embodiments, the present invention is not limited to the embodiments. For example, the photosensitive resin composition, resin film, and semiconductor device according to the present invention may be in which each part of the embodiments is replaced with any configuration having a similar function, or any configuration may be added to the embodiments. [Examples]

[0182] Next, specific embodiments of the present invention will be described. 5. Preparation of photosensitive resin composition A varnish-like photosensitive resin composition was prepared by stirring and mixing each component shown in Tables 1 to 3 under a nitrogen atmosphere, and then filtering it through a polyethylene filter with a pore size of 0.2 μm. Details of each component listed in Tables 1 to 3 are as follows. In Tables 1 to 3, those corresponding to the present invention are labeled as "Examples," and those not corresponding to the present invention are labeled as "Comparative Examples."

[0183] • Phenolic resin (A) • Biphenyl-type phenolic resin (a1-1): A biphenyl-type phenolic resin having the structure represented by the following formula (a1), manufactured by Sumitomo Bakelite Co., Ltd., PR-X21024, Mw=45,000

[0184] [ka]

[0185] Method for producing biphenyl-type phenolic resin (a1-1) In a four-necked glass round-bottom flask equipped with a thermometer, stirrer, raw material inlet, and dry nitrogen gas inlet tube, 186.2 g (1.00 mol) of 4,4'-biphenol, 86.5 g (0.8 mol) of p-cresol, 28.5 g (0.94 mol) of formaldehyde, 15.5 g (0.09 mol) of p-toluenesulfonic acid, and 308 g of γ-butyrolactone were charged. A polycondensation reaction was then carried out at 100°C for 5.5 hours while flowing nitrogen through the flask and refluxing the reaction mixture in an oil bath. Next, the resulting reaction mixture was cooled to room temperature, and 411 g of acetone was added and stirred until homogeneous. Subsequently, the resin component was precipitated by adding the reaction mixture in the round-bottom flask dropwise to 10 L of water and mixing. Next, the precipitated resin components were filtered and recovered, and then vacuum-dried at 60°C to obtain a biphenyl-type phenolic resin (a1-1) having the structure represented by the above formula (a1).

[0186] • Biphenyl-type phenolic resin (a1-2): A biphenyl-type phenolic resin having the structure represented by the above formula (a1), manufactured by Sumitomo Bakelite Co., Ltd., PR-X21024, Mw=11,000

[0187] Method for producing biphenyl-type phenolic resin (a1-2) In a four-necked glass round-bottom flask equipped with a thermometer, stirrer, raw material inlet, and dry nitrogen gas inlet tube, 186.2 g (1.00 mol) of 4,4'-biphenol, 86.5 g (0.8 mol) of p-cresol, 24.0 g (0.8 mol) of formaldehyde, 11.3 g (0.09 mol) of oxalic acid dihydrate, and 308 g of γ-butyrolactone were charged. A polycondensation reaction was then carried out at 100°C for 6 hours while flowing nitrogen and refluxing the reaction mixture in an oil bath. Next, the resulting reaction mixture was cooled to room temperature, and 411 g of acetone was added and stirred until homogeneous. Subsequently, the resin component was precipitated by dropping the reaction mixture in the round-bottom flask into 10 L of water. Next, the precipitated resin components were filtered and recovered, and then vacuum-dried at 60°C to obtain a biphenyl-type phenolic resin (a1-2) having the structure represented by the above formula (a1).

[0188] • Aalkyl-type phenolic resin (a2): Manufactured by Nippon Kayaku Co., Ltd., KAYAHARD, GPH-103

[0189] • Crosslinking agent (B) • The first component (B1) is solid at room temperature. • Urea-based compounds (b1-1, tetrafunctional compounds): Crolin-318, manufactured by Daito Chemix Co., Ltd. • Urea-based compounds (b1-b2, trifunctional compounds): Nikalac MX-270, manufactured by Sanwa Chemical Co., Ltd. • Epoxy compounds (b1-3, trifunctional compounds): Techmore VG3101L, manufactured by Printec Co., Ltd. • The second component (B2) is a liquid at room temperature. • Urea-based compounds (b2-1, bifunctional compounds): Nikalac MX-280, manufactured by Sanwa Chemical Co., Ltd. • Urea-based compounds (b2-2, tetrafunctional compounds): Nikalac MX-279, manufactured by Sanwa Chemical Co., Ltd. • Epoxy compounds (b2-3, bifunctional compounds): Manufactured by Mitsubishi Chemical Corporation, YX-7105

[0190] • Acid generator (C) • Thermal acid generator (C1) • Thermal acid generator c1-1: Compound represented by the following formula (c1-1) (manufactured by Sanshin Chemical Industry Co., Ltd., San-Aid SI-B3A)

[0191] [ka]

[0192] • Thermal acid generator c1-2: Compound represented by the following formula (c1-2) (manufactured by Sanshin Chemical Industry Co., Ltd., San-Aid SI-150)

[0193] [ka]

[0194] • Photoacid generator (C2) • Photoacid generator c2-1:: Naphthoquinone diazide compound having the structure represented by the following formula (NQD-5)

[0195] [ka]

[0196] • Photoacid generator c2-2: Naphthoquinone diazide compound having the structure represented by the following formula (NQD-4)

[0197] [ka]

[0198] • Adhesion enhancer (D) • Heterocyclic aromatic compounds (D1) • Adhesion enhancer (d1): 5-aminotetrazole (5ATZ) • Amino group-containing coupling agent (D2) • Adhesion enhancer (d2-1): γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBE-903) • Adhesion enhancer (d2-2): γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-903) • Other coupling agents (D3) • Adhesion enhancer (d3): γ-Glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-403E)

[0199] • Surfactants (E) • Silicone-based surfactant: Polyether-modified polydimethylsiloxane (manufactured by BIC Chemie Japan, BYK-349)

[0200] ·solvent • γ-butyrolactone (GBL): Manufactured by Sanwa Oil & Chemical Industry Co., Ltd.

[0201] Tables 1 through 3 show the average number of functional groups per molecule of the crosslinking agent (B), the blending ratio B1 / B2, and the blending ratio D1 / D2.

[0202] 6. Characteristics of the photosensitive resin composition The following properties were obtained for the photosensitive resin composition and its cured product.

[0203] 6.1. Delamination of the resin film during development First, the photosensitive resin compositions of each example and comparative example were applied to the upper surface of a silicon wafer using a spin coater. The thickness of the coated film was set to 10 μm after drying. Next, the obtained coated film was pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. Then, the obtained photosensitive film was exposed to a predetermined exposure dose using a stepper equipped with a mask. The mask used was patterned to form trenches with a width of 10 μm after curing. Light including i-lines was used for exposure, and the exposure dose was 500 mJ / cm². 2 That's what I decided.

[0204] Next, a 2.38% aqueous solution of tetramethylammonium hydroxide was used as the developer, and paddle development was performed twice. Then, the wafers were rinsed with pure water for 10 seconds and then dried by shaking. This resulted in silicon wafers with patterned photosensitive coatings.

[0205] Next, the entire surface of the silicon wafer with the patterned photosensitive coating was observed using an optical microscope. The observation results were then evaluated against the following criteria to determine whether or not the trench pattern peeled off (peeling of the resin film during development).

[0206] ○: There are 0 instances of trench pattern delamination. ×: There is one or more instances of trench pattern delamination.

[0207] 6.2 Storage Stability of Photosensitive Resin Compositions For each example and comparative example of the photosensitive resin composition, the viscosity change rate after 1 week at 35°C, the viscosity change rate after 1 month at 23°C, and the viscosity change rate after 1 month at -20°C were measured and evaluated using the following methods.

[0208] First, the initial viscosity of the photosensitive resin composition was measured using an E-type viscometer (TVE-25L). This viscosity was denoted as 'a'.

[0209] Next, the photosensitive resin composition was stored under nitrogen pressure (2 atmospheres) at 35°C for one week, and its viscosity was measured again. This viscosity was denoted as b.

[0210] Next, viscosity a and viscosity b were substituted into the following formula to calculate the viscosity change rate after one week at 35°C. Viscosity change rate [%] = {(viscosity a - viscosity b) / viscosity a} × 100

[0211] Furthermore, the viscosity change rate after one month at 23°C and after one month at -20°C were calculated in the same manner as described above. The calculation results are shown in Tables 1 to 3. It should be noted that a lower viscosity change rate is preferable to obtain a resin film with a stable thickness.

[0212] 6.3. Changes in photosensitivity The photosensitive resin compositions of each example and comparative example were applied to the upper surface of a silicon wafer using a spin coater. Next, the resulting coating was pre-baked on a hot plate at 100°C for 4 minutes to obtain a photosensitive film. The thickness of the obtained photosensitive film was measured and this was defined as the post-PB film thickness.

[0213] This photosensitive film was exposed using a Toppan Printing Co., Ltd. mask (with a 1mm square pattern remaining) and a SUSS MA8 mask aligner. The exposure time was 40 seconds. Next, the exposed areas were dissolved and removed by immersion in a 2.38% tetramethylammonium hydroxide aqueous solution, and then rinsed with pure water for 30 seconds. The film thickness of the unexposed areas was then measured and defined as the film thickness after development.

[0214] Next, the initial film loss was calculated using the following formula. Initial film thickness loss [μm] = Film thickness after PB [μm] - Film thickness after development [μm]

[0215] Next, the photosensitive resin compositions of each example and comparative example were left at 35°C for 7 days. After that, the film loss was calculated again in the same manner as above. The calculated result was taken as the film loss after 7 days.

[0216] Next, the change in film loss after 7 days was calculated using the following formula. The calculation results are shown in Tables 1 to 3. Change in film loss after 7 days [μm] = Initial film loss [μm] - Film loss after 7 days [μm]

[0217] 6.4. Tensile elongation Samples were prepared to calculate the tensile elongation of the cured material using the tensile elongation measurement method described above. Tensile tests were performed on the prepared samples, and the tensile elongation was calculated. The calculation results are shown in Tables 1 to 3.

[0218] 6.5. Patterning Accuracy Using the method described above, a sample was prepared for measuring the taper angle of the end face of the trench pattern. The taper angle θ of the prepared sample was measured. The patterning accuracy of the resin film was then evaluated by comparing the measured taper angle θ of the end face with the following evaluation criteria. The evaluation results are shown in Tables 1 to 3.

[0219] A: The patterning accuracy is particularly good (the taper angle of the end face is 60° or more). B: Good patterning accuracy (end face taper angle is 50° or more and less than 60°) C: Poor patterning accuracy (end face taper angle is less than 50°)

[0220] [Table 1]

[0221] [Table 2]

[0222] [Table 3]

[0223] Based on the evaluation results shown in Tables 1 to 3, the following was observed. • The photosensitive resin compositions of each example were found to exhibit minimal peeling of the resin film during development. • The photosensitive resin compositions of each example were found to have a small rate of viscosity change after storage. The photosensitive resin compositions of each example showed little change in film loss after 7 days, indicating that they exhibited minimal change in photosensitivity after storage. The photosensitive resin compositions of each example were found to have good tensile elongation and patterning accuracy in the cured products. [Explanation of Symbols]

[0224] 2 Subjects 21 Silicon wafers 22 Trench Patterns 24 Resin film 26 Trench 30 Interlayer insulating film 32 Passivation membrane 34 Top layer wiring 40 Redistribution layer 42 Insulating layer 44 Insulating layer 46 Rewiring 50 UBM layers 52 Bump 100 Semiconductor Equipment 212 Top surface 252 End face L straight line θ Taper angle

Claims

1. A photosensitive resin composition used in the manufacture of a resin film for semiconductor devices, Phenolic resin (A) and Crosslinking agent (B), Acid generator (C), Adhesion aid (D), Includes, The aforementioned adhesion aid (D) is A heterocyclic aromatic compound containing an amino group and a nitrogen atom as a heteroatom constituting the ring, A coupling agent containing an amino group, A photosensitive resin composition characterized by containing the following.

2. The photosensitive resin composition according to claim 1, wherein the adhesion aid (D) further comprises a coupling agent containing an epoxy group.

3. The photosensitive resin composition according to claim 1, wherein the acid generating agent (C) comprises a thermal acid generating agent and a photoacid generating agent.

4. The photosensitive resin composition according to claim 1, wherein the crosslinking agent (B) comprises a first component that is solid at room temperature and a second component that is liquid at room temperature.

5. The photosensitive resin composition according to claim 4, wherein the first component comprises a urea-based compound and an epoxy-based compound.

6. The photosensitive resin composition according to claim 5, wherein the epoxy compound contained in the first component contains an aromatic ring.

7. The photosensitive resin composition according to claim 5, wherein the number of functional groups of the epoxy compound contained in the first component is 3 or more.

8. The photosensitive resin composition according to claim 4, wherein the second component comprises a bifunctional phenoxy-type epoxy resin.

9. The photosensitive resin composition according to claim 1, wherein the average number of functional groups of the crosslinking agent (B) is 2.4 or more and 3.6 or less.

10. The photosensitive resin composition according to claim 1, wherein the blending ratio D1 / D2 of the heterocyclic aromatic compound to the coupling agent is 0.01 or more and 0.70 or less by mass ratio.

11. The photosensitive resin composition according to claim 1, wherein the phenolic resin (A) is a biphenyl-type phenolic resin.

12. A resin film characterized by being composed of a cured product of a photosensitive resin composition according to any one of claims 1 to 11.

13. Semiconductor elements and The resin film according to claim 12 is provided on the surface of the semiconductor element, A semiconductor device characterized by comprising the following features.

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