Photosensitive resin composition, cured product, and semiconductor element

Abstract

A photosensitive resin composition according to the present disclosure contains a maleimide compound, a crosslinking agent, and a photopolymerization initiator. The maleimide compound is a reaction product of a tetracarboxylic acid dianhydride (a1), a diamine (a2), a triamine (a3), and a maleic anhydride (a4), the tetracarboxylic acid dianhydride (a1) includes a tetracarboxylic acid dianhydride having an aromatic ring, the diamine (a2) includes a dimer diamine and a second diamine other than the dimer diamine, and at least one of the second diamine and the triamine includes an amine having an aromatic ring.

Description

Photosensitive resin composition, cured product, and semiconductor element

[0001] The present disclosure relates to a photosensitive resin composition, a cured product, and a semiconductor device.

[0002] As semiconductor elements become more highly integrated, smaller, and more minute, insulating films used in surface protection layers, interlayer insulating layers, rewiring layers, and the like of semiconductor elements are required to have better electrical properties, heat resistance, mechanical properties, and the like. As materials for forming insulating films having these properties, photosensitive resin compositions containing alkali-soluble resins have been developed (see, for example, Patent Documents 1, 2, and 3). These photosensitive resin compositions are applied to a substrate and dried to form a resin film, which is then exposed to light and developed to obtain a patterned resin film (a patterned resin film). The patterned resin film can then be heat-cured to form a patterned cured film (a patterned cured film), which can be used as an insulating film.

[0003] JP 2008-309885 A JP 2007-057595 A International Publication No. 2010 / 073948

[0004] Photosensitive resin compositions for forming insulating films such as redistribution layers are required to have high glass transition temperatures (Tg) and adhesive properties while maintaining sufficient microfabrication and dielectric properties. Therefore, an object of the present disclosure is to provide a photosensitive resin composition capable of forming insulating films with high Tg and excellent adhesive properties.

[0005] One aspect of the present disclosure relates to the following photosensitive resin composition, a cured product of the photosensitive resin composition, and a semiconductor device: [1] A photosensitive resin composition containing a maleimide compound, a crosslinking agent, and a photopolymerization initiator, wherein the maleimide compound is a reaction product of a tetracarboxylic dianhydride (a1), a diamine (a2), a triamine (a3), and maleic anhydride (a4), the tetracarboxylic dianhydride (a1) includes a tetracarboxylic dianhydride having an aromatic ring, the diamine (a2) includes a dimer diamine and a second diamine other than the dimer diamine, and at least one of the second diamine and the triamine includes an amine having an aromatic ring. [2] The photosensitive resin composition according to [1] above, wherein the tetracarboxylic dianhydride having an aromatic ring comprises at least one of pyromellitic anhydride, 4,4'-oxydiphthalic anhydride, 3,4'-oxydiphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3',3,4'-biphenyltetracarboxylic dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride. [3] The photosensitive resin composition according to the above [1] or [2], wherein the amine having an aromatic ring is a diamine having an aromatic ring, and the diamine having an aromatic ring comprises at least one of 4,4'-diamino-2,2'-dimethylbiphenyl, 4,4'-diamino-2,2'-diethylbiphenyl, 4,4'-diamino-3,3'-dimethylbiphenyl, 4,4'-diamino-3,3'-diethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetramethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetraethylbiphenyl, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-diamino-2,2'-dimethoxybiphenyl, and 4,4'-diamino-3,3'-dimethoxybiphenyl. [4] The photosensitive resin composition according to any one of the above [1] to [3], wherein the dimer diamine contains at least one of a compound represented by the following general formula (1) and a compound represented by the following general formula (2): [In formulas (1) and (2), m, n, p, and q each represent an integer of 1 or greater selected so that m+n=6 to 17 and p+q=8 to 19, and the bond indicated by a dashed line represents a carbon-carbon single bond or a carbon-carbon double bond. However, when the bond indicated by a dashed line represents a carbon-carbon double bond, formulas (1) and (2) have a structure in which the number of hydrogen atoms bonded to each carbon atom constituting the carbon-carbon double bond is subtracted by one from the number indicated in formulas (1) and (2)].] [5] The photosensitive resin composition according to any one of [1] to [4] above, wherein the maleimide compound has a weight-average molecular weight of 3,000 to 40,000. [6] The photosensitive resin composition according to any one of [1] to [5] above, wherein the crosslinking agent comprises a polymerizable crosslinking agent having a (meth)acryloyl group. [7] The photosensitive resin composition according to any one of [1] to [6] above, wherein the crosslinking agent comprises a polymerizable crosslinking agent having an allyl group or a vinyl group. [8] The photosensitive resin composition according to any one of [1] to [7] above, further comprising a thermal polymerization initiator. [9] A cured product of the photosensitive resin composition according to any one of [1] to [8] above.

[10] A semiconductor device having a rewiring layer comprising the cured product of the photosensitive resin composition according to any one of [1] to [8] above.

[0006] According to the present disclosure, it is possible to provide a photosensitive resin composition capable of forming an insulating film having a high Tg and excellent adhesion, a cured product of the photosensitive resin composition, and a semiconductor element having a redistribution layer including the cured product.

[0007] Preferred embodiments of the present disclosure will be described in detail below. However, the present invention is not limited to the following embodiments and can be practiced in various modifications within the scope of the present disclosure.

[0008] In this specification, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In the numerical ranges described in stages in this specification, the upper or lower limit of a numerical range in a certain stage can be arbitrarily combined with the upper or lower limit of a numerical range in another stage. In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with a value shown in the examples. "A or B" may include either A or B, or may include both. Unless otherwise specified, the materials exemplified in this specification can be used alone or in combination of two or more. When multiple substances corresponding to each component are present in the composition, the content of each component in the composition means the total amount of the multiple substances present in the composition, unless otherwise specified.

[0009] In this specification, the terms "layer" and "film" include not only structures with shapes formed over the entire surface when observed in a plan view, but also structures with shapes formed on a portion of the surface. The term "process" includes not only an independent process, but also a process that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved.

[0010] In this specification, "(meth)acryloyl" means at least one of "acryloyl" and its corresponding "methacryloyl," and the same applies to other similar expressions such as (meth)acrylic acid, (meth)acrylate, etc. In this specification, "solid content" refers to the non-volatile content excluding volatile substances (water, solvent, etc.) contained in the photosensitive resin composition, and also includes components that are liquid, syrup-like, or wax-like at room temperature (around 25°C).

[0011] [Photosensitive Resin Composition] The photosensitive resin composition according to this embodiment contains, as essential components, a maleimide compound having a specific structure, a crosslinking agent, and a photopolymerization initiator. The maleimide compound is a reaction product of a tetracarboxylic dianhydride (a1), a diamine (a2), a triamine (a3), and maleic anhydride (a4). The tetracarboxylic dianhydride (a1) contains a tetracarboxylic dianhydride having an aromatic ring, the diamine (a2) contains a dimer diamine and a second diamine other than the dimer diamine, and at least one of the second diamine and the triamine contains an amine having an aromatic ring. The amine having an aromatic ring is a diamine having an aromatic ring or a triamine having an aromatic ring. The aromatic ring may have a lower alkyl (e.g., methyl, ethyl, propyl, etc.) as a substituent.

[0012] The photosensitive resin composition according to this embodiment may further contain a thermal polymerization initiator, a coupling agent, a rust inhibitor, a polymerization inhibitor, etc., as necessary. The photosensitive resin composition according to this embodiment is a negative photosensitive resin composition, and a cured product of the photosensitive resin composition can be suitably used as an insulating film for a rewiring layer. Each component used in the photosensitive resin composition according to this embodiment will be described in more detail below.

[0013] (Maleimide Compound) The maleimide compound according to this embodiment (hereinafter also referred to as "component (A)") can be obtained by reacting a tetracarboxylic dianhydride (a1) (hereinafter also referred to as "component (a1)"), a diamine (a2) (hereinafter also referred to as "component (a2)"), a triamine (a3) ​​(hereinafter also referred to as "component (a3)"), and maleic anhydride (a4) (hereinafter also referred to as "component (a4)"). That is, the component (A) is a maleimide compound obtained by reacting the components (a1), (a2), and (a3). The component (A) is a polyfunctional maleimide compound having two or more maleimide groups, and may have multiple maleimide groups in the molecule. The component (A) can be used alone or in combination of two or more.

[0014] The tetracarboxylic acid dianhydride of the component (a1) includes a tetracarboxylic acid dianhydride having an aromatic ring. Examples of the tetracarboxylic acid dianhydride having an aromatic ring include pyromellitic anhydride, 4,4'-oxydiphthalic anhydride, 3,4'-oxydiphthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 3,3',4,4'-diphenylsulfonetetracarboxylic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 2,3',3,4'-biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride, 4,4'-(4, aromatic tetracarboxylic acid dianhydrides not having a fluorene skeleton, such as 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride, and 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione.

[0015] From the viewpoint of achieving a high Tg of the cured product, the component (a1) preferably contains, as a tetracarboxylic dianhydride having an aromatic ring, at least one of pyromellitic anhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3',3,4'-biphenyltetracarboxylic dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

[0016] From the viewpoints of the solubility of the maleimide compound and a high Tg of the cured product, it is preferable to use a tetracarboxylic acid dianhydride having a fluorene skeleton and an aromatic tetracarboxylic acid dianhydride not having a fluorene skeleton in combination as the tetracarboxylic acid dianhydride having an aromatic ring. Component (a1) may include, for example, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride and at least one of pyromellitic anhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, and 2,3',3,4'-biphenyltetracarboxylic acid dianhydride.

[0017] The component (a1) may further contain a tetracarboxylic acid dianhydride that does not have an aromatic ring. Examples of the tetracarboxylic acid dianhydride that does not have an aromatic ring include 1,2,3,4-butanetetracarboxylic acid dianhydride, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride, bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid)1,4-phenylene 4,4'-(ethyne-1,2-diyl)diphthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, dicyclohexyl-3,4,3',4'-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclopentanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, and 5,5'-bis-2-norbornene-5,5',6,6'-tetracarboxylic-5,5',6,6'-dianhydride.

[0018] The component (a2) contains a dimer diamine (first diamine) and a second diamine (second amine) other than the dimer diamine.

[0019] Dimer diamine is a compound derived from dimer acid, which is a dimer of unsaturated fatty acids such as oleic acid, as described in, for example, JP-A-9-12712. By using dimer diamine as component (a2), the dielectric properties of the cured product can be reduced. In this embodiment, any known dimer diamine can be used without particular limitations. The dimer diamine preferably includes, for example, at least one of a compound represented by the following general formula (1) and a compound represented by the following general formula (2):

[0020]

[0021] In formulas (1) and (2), m, n, p, and q each represent an integer of 1 or greater selected so that m+n=6 to 17 and p+q=8 to 19, and the bond shown by a dashed line represents a carbon-carbon single bond or a carbon-carbon double bond. However, when the bond shown by a dashed line is a carbon-carbon double bond, formulas (1) and (2) have a structure in which the number of hydrogen atoms bonded to each carbon atom constituting the carbon-carbon double bond is reduced by one from the number shown in formulas (1) and (2).

[0022] The dimer diamine may be one represented by the above general formula (2), particularly a compound represented by the following formula (3), from the viewpoints of solubility in organic solvents, heat resistance, heat-resistant adhesion, low viscosity, etc.

[0023] Commercially available dimer diamines include, for example, PRIAMINE 1075 and PRIAMINE 1074 (both manufactured by Croda Japan), etc. These may be used alone or in combination of two or more.

[0024] The second diamine is a diamine that does not fall under the category of the above-mentioned dimer diamine. The second diamine may include a diamine having an aromatic ring as the amine having an aromatic ring.

[0025] Examples of diamines having an aromatic ring include 4,4'-diamino-2,2'-dimethylbiphenyl, 4,4'-diamino-2,2'-diethylbiphenyl, 4,4'-diamino-3,3'-dimethylbiphenyl, 4,4'-diamino-3,3'-diethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetramethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetraethylbiphenyl, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-diamino-2, Diamines having a biphenyl skeleton such as 2'-dimethoxybiphenyl and 4,4'-diamino-3,3'-dimethoxybiphenyl; diamines having a fluorene skeleton such as 2,7-diaminofluorene, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis[3-fluoro-4-aminophenyl]fluorene and 9,9-bis[4-(4-aminophenoxy)phenyl]fluorene; phenylenediamines such as paraphenylenediamine, orthophenylenediamine and metaphenylenediamine; and 4,4-methylenediamine. Aniline, 4,4'-ethylenedianiline, 1,3-bis[2-(4-aminophenyl)-2-propyl]benzene, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 4,4'-(hexafluoroisopropylidene)dianiline, 1,1-bis(4-aminophenyl)cyclohexane, 4,4'-methylenebis(2,6-diethylaniline), 4,4'-methylenebis(2-ethyl-6-methylaniline), 2,2-bis[4-(4-aminophenoxy)phenyl]propane, bis Examples of bisaniline derivatives include [4-(4-aminophenoxy)phenyl]methane, bis[4-(4-aminophenoxy)phenyl]ether, bis[4-(4-aminophenoxy)phenyl]ketone, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, bis[4-(3-aminophenoxy)phenyl]sulfone, and bis[4-(4-aminophenoxy)phenyl]sulfone. These can be used alone or in combination of two or more.

[0026] From the viewpoint of increasing the Tg of the cured product, the diamine having an aromatic ring may contain at least one diamine having a biphenyl skeleton selected from 4,4'-diamino-2,2'-dimethylbiphenyl, 4,4'-diamino-2,2'-diethylbiphenyl, 4,4'-diamino-3,3'-dimethylbiphenyl, 4,4'-diamino-3,3'-diethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetramethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetraethylbiphenyl, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-diamino-2,2'-dimethoxybiphenyl, and 4,4'-diamino-3,3'-dimethoxybiphenyl.

[0027] The content of the diamine having an aromatic ring, based on the total amount of components (a2) and (a3), may be 20 mol% or more, 25 mol% or more, 30 mol% or more, or 35 mol% or more from the viewpoint of increasing the Tg of the cured product, and may be 60 mol% or less, 55 mol% or less, 50 mol% or less, or 45 mol% or less from the viewpoint of decreasing the dielectric properties of the cured product.

[0028] The second diamine may include a diamine having no aromatic ring. Examples of diamines having no aromatic ring include 1,3-diaminopropane, norbornanediamine, norbornenediamine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, isophoronediamine, 4,4′-methylenebis(cyclohexylamine), 1,4-bisaminopropylpiperazine, and 4,4′-methylenebis(2-methylcyclohexylamine).

[0029] Examples of triamines of component (a3) ​​include aliphatic triamines such as tris(2-aminomethyl)amine, tris(2-aminoethyl)amine, tris(2-aminopropyl)amine, 2-(aminomethyl)-2-methyl-1,3-propanediamine, and trimer triamine; triamines having a heterocyclic ring such as 1,3,5-triazine-2,4,6-triamine and 2,4,6-triaminopyrimidine; and triamines having an aromatic ring such as 3,4,4'-triaminodiphenyl ether, 1,2,4-triaminobenzene, 1,3,5-triaminobenzene, 1,2,3-triaminobenzene, 1,3,5-tris(4-aminophenyl)benzene, 1,3,5-tris(4-aminophenoxy)benzene, and tris(4-aminophenyl)methane. These can be used alone or in combination of two or more. Of these, aliphatic triamines are preferred from the viewpoint of the solubility of the synthesized component (A) in organic solvents, and tris(2-aminomethyl)amine and tris(2-aminoethyl)amine, which have a small number of carbon atoms, are more preferred from the viewpoint of achieving a high Tg.

[0030] The content of the component (a3), based on the total amount of the components (a2) and (a3), may be 1 mol % or more, 4 mol % or more, 6 mol % or more, or 8 mol % or more from the viewpoints of the haze (turbidity) of the maleimide compound and the elastic modulus and Tg of the cured product, and may be 30 mol % or less, 25 mol % or less, 20 mol % or less, or 15 mol % or less from the viewpoints of the solubility and haze of the maleimide compound.

[0031] By using dimer diamine as the diamine, a cured product with lower dielectric properties can be formed. On the other hand, when only dimer diamine is used as the diamine, the Tg of the cured product decreases. In contrast, by using dimer diamine, a second diamine, and a triamine, an insulating film with a high Tg and excellent adhesion can be formed while maintaining the dielectric properties of the cured product.

[0032] Component (A) can be produced by various known methods. For example, components (a1), (a2), and (a3) ​​are first subjected to a polyaddition reaction at a temperature of about 60 to 120°C, preferably 70 to 90°C, for typically about 0.1 to 2 hours, preferably 0.1 to 1.0 hour. The resulting polyaddition product is then subjected to an imidization reaction, i.e., a dehydration ring-closing reaction, at a temperature of about 80 to 250°C, preferably 100 to 200°C, for about 0.5 to 30 hours, preferably 0.5 to 10 hours. The product of the dehydration ring-closing reaction is then subjected to a maleimidization reaction, i.e., a dehydration ring-closing reaction, with component (a4) at a temperature of about 60 to 250°C, preferably 80 to 200°C, for about 0.5 to 30 hours, preferably 0.5 to 10 hours, to obtain the desired component (A).

[0033] In the imidization reaction or maleimidization reaction, various known reaction catalysts, dehydrating agents, and solvents can be used.

[0034] Examples of the reaction catalyst include aliphatic tertiary amines such as triethylamine, aromatic tertiary amines such as dimethylaniline, heterocyclic tertiary amines such as pyridine, picoline, isoquinoline, and organic acids such as methanesulfonic acid, paratoluenesulfonic acid monohydrate, etc. Examples of the dehydrating agent include aliphatic acid anhydrides such as acetic anhydride, and aromatic acid anhydrides such as benzoic anhydride.

[0035] Examples of the solvent include aromatic hydrocarbon solvents such as benzene, toluene, xylene, mesitylene, and pseudocumene; alcohol solvents such as methanol, ethanol, isopropyl alcohol, butanol, pentanol, hexanol, propanediol, and phenol; ether solvents such as anisole; ketone solvents such as acetone, methyl isobutyl ketone, methyl ethyl ketone, pentanone, hexanone, cyclopentanone, cyclohexanone, isophorone, and acetophenone; cellosolves such as methyl cellosolve and ethyl cellosolve, ester solvents such as methyl acetate, ethyl acetate, butyl acetate, methyl propionate, butyl formate, and γ-butyrolactone; and ethylene glycol ether-based solvents such as glycol mono-n-butyl ether, ethylene glycol mono-iso-butyl ether, ethylene glycol mono-tert-butyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol mono-iso-butyl ether, triethylene glycol mono-n-butyl ether, and tetraethylene glycol mono-n-butyl ether; and amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide. These solvents can be used alone or in combination of two or more.

[0036] Component (A) can be purified by various known methods to increase its purity. For example, first, component (A) dissolved in a solvent and pure water are placed in a separatory funnel. The separatory funnel is then shaken and allowed to stand. Subsequently, the aqueous layer and organic layer are separated, and only the organic layer is recovered, thereby purifying component (A).

[0037] The component (A) produced by the above method may contain one or more structural units represented by the following general formulas (4) to (6). The range of the number of functional groups (number of maleimide groups) of the component (A) depends on the triamine content, but is expected to be 2 to 6 functional groups per molecule. The component (A) may be a mixture of multiple compounds having different structures or different numbers of functional groups. The component (A) may contain a compound having three or more functional groups per molecule, including one or more structural units represented by the following general formulas (5) to (6).

[0038]

[0039] In general formulas (4) to (6), X each independently represents a tetravalent organic group, Y each independently represents a divalent organic group, and Z each independently represents a trivalent organic group. X, Y, and Z may be an aliphatic group, an organic group having an alicyclic structure, or an aromatic ring, and may contain a heteroatom. Y may be an organic group derived from a dimer diamine, and Z may be an organic group derived from a triamine (a3).

[0040] An example of the structure of component (A) produced by the above method is shown in general formula (7) below.

[0041]

[0042] X, Y, and Z in general formula (7) are synonymous with X, Y, and Z in general formulas (4) to (6). Furthermore, a represents an integer of 0 to 20, b represents an integer of 0 to 30, c represents an integer of 0 to 20, and d represents an integer of 1 to 30. In general formula (7), the positions of the structural unit assigned with the symbol a (structural unit represented by the above general formula (5)), the structural unit assigned with the symbol b (structural unit represented by the above general formula (4)), and the structural unit assigned with the symbol c (structural unit represented by the above general formula (6)) may be interchanged. Component (A) may contain a compound having three or more functional groups per molecule, in which at least one of a and c is an integer of 1 or greater.

[0043] The molecular weight of component (A) can be controlled by the number of moles of component (a1), component (a2), and component (a3), and the smaller the number of moles of component (a1) is compared to the total number of moles of component (a2) and component (a3) ​​combined, the smaller the molecular weight can be. For the purpose of easily achieving the effects of the present disclosure, the number of moles of component (a1) per mole of component (a2) and component (a3), i.e., [number of moles of component (a1)] / [number of moles of component (a2) + number of moles of component (a3)] is usually about 0.30 to 0.98, preferably 0.40 to 0.96, more preferably 0.50 to 0.94, and even more preferably 0.60 to 0.90.

[0044] From the viewpoint of solubility in solvents and heat resistance, the molecular weight of component (A) is preferably a weight average molecular weight (Mw) of 3,000 to 40,000, and may be 4,000 to 30,000, 5,000 to 28,000, 7,000 to 27,000, 10,000 to 25,000, 12,000 to 22,000, or 13,000 to 20,000. When the weight average molecular weight is 40,000 or less, solubility in organic solvents is good, and when it is 3,000 or more, the effect of improving heat resistance tends to be sufficiently obtained. Mw can be measured by gel permeation chromatography (GPC) and converted using a calibration curve of standard polystyrene.

[0045] (Crosslinking Agent) The crosslinking agent (hereinafter also referred to as "component (B)") may be a polymerizable crosslinking agent. The polymerizable group may be a photopolymerizable group or a thermally polymerizable group. Examples of the polymerizable group include a (meth)acryloyl group, an allyl group, and a vinyl group. The component (B) may be a polyfunctional compound having two or more polymerizable groups. Furthermore, the component (B) can crosslink not only with itself but also with the component (A), for example, during exposure of the photosensitive layer. Furthermore, the component (B) can crosslink with itself, for example, during heating of the resin film after pattern formation. The component (B) can be used alone or in combination of two or more.

[0046] From the viewpoint of dielectric properties, the resin composition according to this embodiment may contain a polymerizable crosslinking agent having a (meth)acryloyl group as a crosslinking agent. The polymerizable crosslinking agent having a (meth)acryloyl group can crosslink not only with itself but also with component (A) during exposure of the photosensitive layer. The polymerizable crosslinking agent having a (meth)acryloyl group may be an acrylate compound or a methacrylate compound. From the viewpoint of dielectric properties, component (B) may contain a methacrylate compound.

[0047] Examples of polymerizable crosslinking agents having a (meth)acryloyl group include tricyclodecane dimethanol di(meth)acrylate, tris-(2-(meth)acryloyloxyethyl)isocyanurate, dioxane glycol di(meth)acrylate, alkoxylated glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, alkoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, alkoxylated pentaerythritol tetra(meth)acrylate, and 1,6-hexane. Examples of the diol di(meth)acrylate include diol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, propoxylated ethoxylated bisphenol A (meth)acrylate, dipentaerythritol poly(meth)acrylate, alkoxylated dipentaerythritol poly(meth)acrylate, ethoxylated isocyanuric acid tri(meth)acrylate, polyethylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate.

[0048] The polymerizable crosslinking agent having a (meth)acryloyl group may contain at least one selected from the group consisting of tricyclodecane dimethanol di(meth)acrylate, tris-(2-(meth)acryloyloxyethyl)isocyanurate, and dioxane glycol di(meth)acrylate, from the viewpoints of heat resistance, dielectric properties, and microprocessability, and may contain tris-(2-(meth)acryloyloxyethyl)isocyanurate from the viewpoints of heat resistance and dielectric properties.

[0049] The resin composition according to the present embodiment may contain a polymerizable crosslinking agent having an allyl group or a vinyl group as a crosslinking agent from the viewpoints of dielectric properties and heat resistance. The polymerizable crosslinking agent having an allyl group or a vinyl group can crosslink with itself when the resin film is heated after pattern formation.

[0050] Examples of polymerizable crosslinking agents having an allyl group include 1,3,4,6-tetraallyl glycoluril, triallyl isocyanurate, diallyl monoglycidyl isocyanurate, diallyl monomethyl isocyanurate, diallyl isocyanurate, triallyl trimellitate, and triallyl orthoformate.

[0051] Examples of the polymerizable crosslinking agent having a vinyl group include a polyvinylbenzyl compound and a polyvinylbenzyl ether compound.

[0052] The polymerizable crosslinking agent having an allyl group or a vinyl group may include at least one selected from the group consisting of 1,3,4,6-tetraallyl glycoluril, triallyl isocyanurate, diallyl isocyanurate, and a polyvinyl benzyl ether compound from the viewpoint of dielectric properties and microprocessability, and may include triallyl isocyanurate from the viewpoint of dielectric properties.

[0053] From the viewpoint of further improving the balance between low dielectric properties and micro-processability, the content of component (B) is preferably less than 50 parts by mass, and may be 1 to 45 parts by mass, 5 to 40 parts by mass, 8 to 30 parts by mass, or 10 to 20 parts by mass, when the total amount of component (A) and component (B) is 100 parts by mass.

[0054] (Photopolymerization initiator) The photopolymerization initiator (hereinafter also referred to as "component (C)") is not particularly limited as long as it is a compound that initiates polymerization upon irradiation with actinic rays (ultraviolet rays, etc.), and examples thereof include alkylphenone-based photopolymerization initiators, acylphosphine oxide-based photopolymerization initiators, intramolecular hydrogen abstraction photopolymerization initiators, and oxime ester-based photopolymerization initiators.

[0055] Alkylphenone-based photopolymerization initiators are commercially available, for example, from IGM Resins B.V. as Omnirad 651, Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127, Omnirad 907, Omnirad 369, Omnirad 379EG, etc. Acylphosphine oxide-based photopolymerization initiators are commercially available, for example, from IGM Resins B.V. as Omnirad 819, Omnirad TPO H, etc. Intramolecular hydrogen abstraction photopolymerization initiators are commercially available, for example, from IGM Resins B.V. Omnirad MBF, Omnirad 754, etc. manufactured by BASF Japan Ltd. Oxime ester photopolymerization initiators are commercially available, for example, as Irgacure OXE01, Irgacure OXE02, etc. manufactured by BASF Japan Ltd. In order to promote the photoreaction, a titanocene photopolymerization initiator (for example, Irgacure 784 manufactured by BASF Japan Ltd.) may be used in combination.

[0056] The content of the component (C) may be 0.1 to 10.0 parts by mass, 0.5 to 8.0 parts by mass, 0.8 to 6.0 parts by mass, or 1.0 to 5.0 parts by mass per 100 parts by mass of the total amount of the component (A) and the component (B), because excellent micro-processability is easily obtained.

[0057] (Thermal Polymerization Initiator) The photosensitive resin composition according to this embodiment may further contain a thermal polymerization initiator as component (D) from the viewpoint of promoting the polymerization reaction of the thermally polymerizable group. The component (D) is preferably a compound that decomposes upon heating during curing to generate radicals and promote the polymerization reaction of components (A) and (B). Examples of the component (D) include organic peroxides.

[0058] Examples of organic peroxides include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methylacetoacetate peroxide, acetylacetone peroxide, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2,2-bis(4,4-di-t-butylperoxy)cyclohexane, t-butylperoxycyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, n-butyl-4,4-bis(t-butylperoxy)valerate, 2,2-bis(t-butylperoxy)butane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, t-butyl hydroperoxide, p-menthane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-hexyl hydroperoxide, dicumyl peroxide, 2,5-dimethyl -2,5-bis(t-butylperoxy)hexane, α,α'-bis(t-butylperoxy)diisopropylbenzene, t-butylcumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, cinnamic acid peroxide, m-toluoyl peroxide, benzoyl peroxide, diisopropyl Peroxydicarbonate, bis(4-t-butylcyclohexyl)peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-sec-butyl peroxydicarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate, α,α'-bis(neodecanoylperoxy)diisopropylbenzene, cumyl peroxyneodecanoate, 1,1,3,3,-Tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-hexylperoxypivalate, t-butylperoxypivalate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyrate, t-butylperoxy Examples of peroxybenzoates include tert-butylperoxymethyl ...

[0059] The content of component (D) is not particularly limited, but may be 0.1 to 10.0 parts by mass, 0.3 to 8.0 parts by mass, 0.5 to 5.0 parts by mass, 0.7 to 3.0 parts by mass, or 0.7 to 2.0 parts by mass relative to 100 parts by mass of the total amount of component (A) and component (B).

[0060] (Coupling Agent) The photosensitive resin composition according to this embodiment may further contain a coupling agent from the viewpoint of improving the adhesion of a cured product of the photosensitive resin composition. The coupling agent may be a silane coupling agent. The silane coupling agent may have, for example, a vinyl group, an epoxy group, a styryl group, an acryloyl group, a methacryloyl group, an amino group, a ureido group, an isocyanate group, an isocyanurate group, or a mercapto group.

[0061] Examples of silane coupling agents having a vinyl group include KBM-1003 and KBE-1003 (trade names manufactured by Shin-Etsu Chemical Co., Ltd.; the same applies hereinafter). Examples of silane coupling agents having an epoxy group include KBM-303, 402, 403, KBE-402, 403, X-12-981S, and X-12-984S. Examples of silane coupling agents having a styryl group include KBM-1403. Examples of silane coupling agents having a methacryloyl group include KBM-502, 503, KBE-502, and 503. Examples of silane coupling agents having an acryloyl group include KBM-5103, X-12-1048, and X-12-1050. Examples of silane coupling agents having an amino group include KBM-602, 603, 903, 573, 575, KBE-903, 9103P, and X-12-972F. Examples of silane coupling agents having a ureido group include KBE-585. Examples of silane coupling agents having an isocyanate group include KBE-9007 and X-12-1159L. Examples of silane coupling agents having an isocyanurate group include KBM-9659. Examples of silane coupling agents having a mercapto group include KBM-802, 803, X-12-1154, and X-12-1156. The silane coupling agent may be a silane coupling agent having a methacryloyl group. The silane coupling agents may be used alone or in combination of two or more.

[0062] The content of the silane coupling agent may be 0.01 to 10.0 parts by mass, 0.1 to 8.0 parts by mass, 0.3 to 6.0 parts by mass, 0.5 to 5.0 parts by mass, or 1.0 to 3.0 parts by mass, relative to 100 parts by mass of the total amount of the (A) component and the (B) component.

[0063] (Rust inhibitor) The photosensitive resin composition according to this embodiment may further contain a rust inhibitor in order to suppress corrosion or prevent discoloration of copper wiring. Examples of the rust inhibitor include triazole derivatives such as benzotriazole, and tetrazole derivatives. The rust inhibitor may be used alone or in combination of two or more.

[0064] The content of the rust inhibitor may be 0.01 to 10.0 parts by mass, 0.1 to 5.0 parts by mass, 0.3 to 4.0 parts by mass, 0.5 to 3.0 parts by mass, or 1.0 to 3.0 parts by mass, relative to 100 parts by mass of the total amount of component (A) and component (B).

[0065] (Polymerization Inhibitor) The photosensitive resin composition according to this embodiment may further contain a polymerization inhibitor from the viewpoint of storage stability.

[0066] Examples of polymerization inhibitors include 4-tert-butylcatechol, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy radical, p-methoxyphenol, diphenyl-p-benzoquinone, benzoquinone, hydroquinone, pyrogallol, phenothiazine, resorcinol, ortho-dinitrobenzene, para-dinitrobenzene, meta-dinitrobenzene, phenanthraquinone, N-phenyl-2-naphthylamine, cupferron, 2,5-toluquinone, tannic acid, parabenzylaminophenol, tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanuric acid, and nitrosamines. One type of polymerization inhibitor may be used alone, or two or more types may be used in combination.

[0067] The content of the polymerization inhibitor may be 0.01 to 10.0 parts by mass, 0.05 to 5.0 parts by mass, 0.10 to 2.0 parts by mass, or 0.10 to 1.0 parts by mass, relative to 100 parts by mass of the total amount of the (A) component and the (B) component.

[0068] (Sensitizer) The photosensitive resin composition may further contain a sensitizer from the viewpoint of maintaining both a good film remaining rate over a wide range of exposure doses and good resolution.

[0069] Examples of sensitizers include Michler's ketone, benzoin, 2-methylbenzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, 2-t-butylanthraquinone, 1,2-benzo-9,10-anthraquinone, anthraquinone, methylanthraquinone, 4,4'-bis(diethylamino)benzophenone, acetophenone, benzophenone, thioxanthone, 1,5-acenaphthene, 2,2-dimethoxy-2-phenylacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-[4-(methylthio)phenyl]-2-morpholino-1-propanone, diacetylbenzyl, benzil dimethyl ketal, and benzil. Examples of sensitizers include phenyl diethyl ketal, diphenyl disulfide, anthracene, phenanthrenequinone, riboflavin tetrabutylate, acridine orange, erythrosine, phenanthrenequinone, 2-isopropylthioxanthone, 2,6-bis(p-diethylaminobenzylidene)-4-methyl-4-azacyclohexanone, 6-bis(p-dimethylaminobenzylidene)-cyclopentanone, 2,6-bis(p-diethylaminobenzylidene)-4-phenylcyclohexanone, aminostyryl ketone, 3-ketocoumarin compounds, biscoumarin compounds, N-phenylglycine, N-phenyldiethanolamine, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone.

[0070] When the photosensitive resin composition contains a sensitizer, the content thereof is preferably 0.1 to 2.0 parts by mass, and more preferably 0.2 to 1.5 parts by mass, per 100 parts by mass of the total amount of the components (A) and (B).

[0071] (Solvent) The photosensitive resin composition according to this embodiment contains a solvent for dissolving and dispersing each component, which makes it easy to apply the composition to a substrate and allows a coating film of uniform thickness to be formed. The solvent may be used alone or in combination of two or more.

[0072] Examples of the solvent include ketone-based solvents such as methyl ethyl ketone, cyclohexanone, and cyclopentanone; aromatic hydrocarbon-based solvents such as toluene, xylene, tetramethylbenzene, mesitylene, and pseudocumene; glycol ether-based solvents such as methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether; ester-based solvents such as ethyl acetate, butyl acetate, butyl cellosolve acetate, carbitol acetate, and γ-butyrolactone; and amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide.

[0073] The amount of the solvent to be added is not particularly limited, but may be an amount such that the solid content in the photosensitive resin composition is 5 to 60 mass %, 10 to 50 mass %, or 15 to 40 mass %.

[0074] The preparation method, conditions, etc. of the photosensitive resin composition are not particularly limited. For example, a method may be used in which predetermined amounts of each main component are thoroughly and uniformly stirred and mixed using a mixer or the like, and then kneaded using a mixing roll, an extruder, a kneader, a roll, an extruder, etc. The kneading method is not particularly limited.

[0075] The dielectric constant at 10 GHz of the cured product of the photosensitive resin composition according to this embodiment may be 2.80 or less, 2.75 or less, or 2.70 or less. The dielectric loss tangent at 10 GHz of the cured product of the photosensitive resin composition may be 0.0060 or less, 0.0050 or less, 0.0045 or less, or 0.0040 or less. The dielectric constant and dielectric loss tangent can be measured using a cured film of the photosensitive resin composition by the method described in the examples.

[0076] The photosensitive resin composition according to this embodiment is capable of forming a fine pattern. The photosensitive resin composition according to this embodiment is capable of forming an insulating film that exhibits low dielectric properties and excellent insulating reliability. A semiconductor element having an interlayer insulating layer formed from a cured product of the above-described photosensitive resin composition, and an electronic device including the semiconductor element can be produced. The semiconductor element can have improved high-frequency characteristics by having a rewiring layer including a cured product of the photosensitive resin composition according to this embodiment. The semiconductor element may be, for example, a memory, a package, or the like having a multilayer wiring structure, a rewiring structure, or the like. Examples of electronic devices include mobile phones, smartphones, tablet terminals, personal computers, and hard disk suspensions. By providing a patterned cured film formed from the photosensitive resin composition according to this embodiment, semiconductor elements and electronic devices with excellent reliability can be provided.

[0077] The present disclosure will be specifically described below with reference to examples and comparative examples, but the present disclosure is not limited thereto. In each example, parts and percentages are by mass unless otherwise specified.

[0078] [Synthesis of Maleimide Compound] In order to synthesize a maleimide compound, the following components (a1) to (a4), an acid catalyst, and a solvent were prepared. (Component (a1)) BPAF: 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride (manufactured by JFE Chemical Corporation, trade name "BPAF") PMDA: pyromellitic dianhydride (manufactured by Daicel Corporation) ODPA: 4,4'-oxydiphthalic anhydride (manufactured by Manac Corporation, trade name "ODPA") s-BPDA: 3,3',4,4'-biphenyltetracarboxylic dianhydride (manufactured by JFE Chemical Corporation, trade name "BPDA") a-BPDA: 2,3',3,4'-biphenyltetracarboxylic dianhydride (manufactured by JFE Chemical Corporation, trade name "a-BPDA") (Component (a2)) DDA: dimer diamine (manufactured by Croda Japan Co., Ltd., trade name "PRIAMINE 1075") mTBHG: 4,4'-diamino-2,2'-dimethylbiphenyl (manufactured by Wakayama Seika Kogyo Co., Ltd., trade name "m-TB-HG") NBDA: norbornanediamine (manufactured by Mitsui Fine Chemicals, Inc.) (component (a3)) TAEA: tris(2-aminoethyl)amine (manufactured by Tokyo Chemical Industry Co., Ltd.) (component (a4)) Maleic anhydride (manufactured by Fuso Chemical Co., Ltd.) (acid catalyst) Methanesulfonic acid aqueous solution (manufactured by BASF, trade name "Lutropur MSA") (solvent) Pseudocumene (manufactured by Toyo Gosei Co., Ltd., aromatic high-boiling point solvent) Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd., alcohol-based solvent) γ-butyrolactone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Toluene (manufactured by Yamaichi Chemical Industry Co., Ltd.) N-methyl-2-pyrrolidone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

[0079] Synthesis Example 1 Into a 0.3 L flask equipped with a condenser, a nitrogen inlet tube, a thermocouple, and a stirrer, 18.48 parts by mass of 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride (BPAF), 8.8 parts by mass of pyromellitic dianhydride (PMDA), 123.49 parts by mass of pseudocumene, 33.45 parts by mass of Solmix A-11, and 29.94 parts by mass of γ-butyrolactone were added. After addition, the temperature was raised to 80°C and maintained at that temperature for 0.5 hours. 25.98 parts by mass of dimer diamine (DDA) was added dropwise, followed by the dropwise addition of 1.05 parts by mass of tris(2-aminoethyl)amine (TAEA), and then 10.28 parts by mass of 4,4'-diamino-2,2'-dimethylbiphenyl (mTBHG). After the addition, 2.69 parts by mass of a methanesulfonic acid aqueous solution was added, and the temperature was raised to 160°C. After the temperature was raised, 40.00 parts by mass of toluene was added, and a dehydration ring-closing reaction was carried out at 160°C for 3 hours, and water and alcohol were removed from the reaction solution to obtain an intermediate polyimide. Subsequently, the polyimide was cooled to 130°C, and 7.93 parts by mass of maleic anhydride was added, and the temperature was raised to 160°C, and a dehydration ring-closing reaction was carried out at 160°C for 4 hours, and water was removed from the reaction solution to obtain a maleimide compound.

[0080] The maleimide compound was placed in a separatory funnel, and 500 parts by mass of pure water was added. The separatory funnel was shaken and allowed to stand. After standing, the aqueous layer and the organic layer separated, and only the organic layer was recovered. The recovered organic layer was placed in a 1 L glass vessel equipped with a cooler, a nitrogen inlet tube, a thermocouple, a stirrer, and a vacuum pump, heated to 88 to 93°C, and the water was removed. The vessel was then heated to 100°C and the solvent was partially removed for 0.5 hours under a reduced pressure of 0.1 MPa from atmospheric pressure, yielding a solution of maleimide compound (A-1) as component (A).

[0081] Synthesis Examples 2 to 8 Solutions of maleimide compounds (A-2) to (A-8) were obtained in the same manner as in Synthesis Example 1, except that the amounts of each component were changed as shown in Table 1.

[0082] Synthesis Example 9 A solution of maleimide compound (A-9) was obtained in the same manner as in Synthesis Example 1, except that γ-butyrolactone was changed to N-methyl-2-pyrrolidone (NMP) and the amounts of each component were changed as shown in Table 1.

[0083] (Nonvolatile Content) 0.75 g±0.25 g of the maleimide compound solution was weighed out using a precision balance and placed in a metal Petri dish, and then dried in a hot air dryer at 150°C for 0.5 hours. The nonvolatile content (NV) was calculated using the following formula: NV (mass%)={(W3-W1) / W2}×100, where W1 is the mass (g) of the empty metal Petri dish, W2 is the mass (g) of the maleimide compound solution before drying, and W3 is the mass (g) of the metal Petri dish + maleimide compound after drying.

[0084] (Solubility) The solubility of the maleimide compound was evaluated by placing a solution of the maleimide compound in a 20 mL screw tube and visually checking for the presence of precipitates or turbidity. The solubility was evaluated as "A" when the maleimide compound solution had no precipitates or turbidity, "B" when the maleimide compound solution had turbidity but no precipitates, and "C" when the maleimide compound solution had precipitates.

[0085] (Weight-Average Molecular Weight) The weight-average molecular weight (Mw) of the maleimide compounds of Synthesis Examples 1 to 5, 7, and 8 was measured by gel permeation chromatography (GPC). A sample prepared by dissolving the maleimide compound in tetrahydrofuran (THF) to a concentration of 3% by mass was injected in an amount of 50 μL into a column (one GL-R420, one GL-R430, one GL-R440 (all manufactured by Hitachi High-Tech Fielding Corporation) heated to 30°C, and measurement was carried out using THF as the developing solvent at a flow rate of 1.6 mL / min. An L-3350 RI detector (manufactured by Hitachi, Ltd.) was used as the detector, and Mw was calculated from the elution time using a molecular weight / elution time curve prepared using standard polystyrene (manufactured by Tosoh Corporation).

[0086]

[0087] The following compounds were prepared as component (B): A-9300: Tris-(2-acryloyloxyethyl) isocyanurate (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.) TAIC: Triallyl isocyanurate (trade name, manufactured by Shinryo Corporation) A-DOG: Dioxane glycol diacrylate (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0088] The following compounds were prepared as component (C), coupling agent, polymerization inhibitor, rust inhibitor, and solvent. Component (C): oxime ester photopolymerization initiator (manufactured by BASF Japan Ltd., trade names "Irgacure OXE01" and "Irgacure OXE02") Coupling agent: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name "KBM-503") Polymerization inhibitor: 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy radical (TEMPOL) (manufactured by Tokyo Chemical Industry Co., Ltd.) Rust inhibitor: 1,2,3-benzotriazole (manufactured by Johoku Chemical Industry Co., Ltd., trade name "BT-120") Solvent: mesitylene (manufactured by Toyo Gosei Co., Ltd.)

[0089] [Photosensitive Resin Composition] For the maleimide compounds of Synthesis Examples 1 to 5 and 7 to 9, the components were mixed in the amounts (parts by mass, solid content) shown in Table 2 or Table 3, stirred at 25°C for 30 minutes or more, and then filtered through a filter with a mesh size of 0.5 µm to prepare photosensitive resin compositions of the Examples and Comparative Examples.

[0090] The photosensitive resin composition was spin-coated onto a silicon wafer with a Cu sputtered film, and then heated and dried at 90°C for 5 minutes to form a resin film with a thickness of 14 µm. Then, a mask aligner exposure machine (manufactured by Mikasa Co., Ltd., product name "MA-20") was used to expose the film to an exposure dose of 1000 mJ / cm. ２ The resin film was patterned under these conditions to produce a 10 mm wide resin film, and then heated at 100°C for 1 minute. The exposed resin film was developed using a developer (a mixture of cyclopentanone and propylene glycol monomethyl ether acetate) at 25°C for 30 seconds, then washed with propylene glycol monomethyl ether acetate and cured at 200°C for 2 hours under a nitrogen atmosphere. The silicon wafer on which the patterned cured film had been formed was immersed in an aqueous ammonium persulfate solution, and the cured film was peeled off from the silicon wafer. The cured film was washed with pure water to obtain a 10 mm wide strip-shaped resin film. The resin film was cut into 50 mm lengths, and Tg was measured using a dynamic viscoelasticity measuring device (manufactured by TA Instruments Japan, Inc., product name "RSA G2") at a chuck distance of 20 mm and a measurement temperature range of -50 to 350°C.

[0091] (Adhesion) A photosensitive resin composition was spin-coated onto a silicon wafer with a Cu sputtered film, and then heated and dried at 90°C for 5 minutes to form a resin film. Then, a mask aligner exposure machine (MA-20) was used to expose the film to an exposure dose of 1000 mJ / cm. ２ The entire surface was exposed to light under the conditions of (1) and (2), and then heated at 100°C for 1 minute. The silicon wafer on which the resin film had been formed was heated at 200°C for 2 hours under a nitrogen atmosphere, forming a 5 μm thick cured film on the silicon wafer. Using a cross-cut guide (manufactured by Cortec Co., Ltd., product name "CCJ-1") and a cutter (NT cutter eA-300), 11 incisions were made in the cured film at 1 mm intervals, creating 100 grids. Cellophane tape (manufactured by Nichiban Co., Ltd., product name "CT1535") was firmly pressed onto the grids, and the tape was then peeled off, and the number of grids remaining without peeling was evaluated. The same evaluation was performed three times, and the average evaluation results are shown in Tables 2 and 3.

[0092] (Photosensitive Properties) The photosensitive resin composition of Example 1 was spin-coated on a silicon wafer and dried by heating at 90°C for 5 minutes to form a resin film with a thickness of 7 µm. Then, a mask aligner exposure machine (MA-20) was used to expose the film to an exposure dose of 1000 mJ / cm. ２ The resin film was subjected to pattern exposure under the conditions of (a) and (b) above, and then heated at 100°C for 1 minute. The silicon wafer on which the exposed resin film had been formed was developed using a developer (a mixed liquid of cyclopentanone and propylene glycol monomethyl ether acetate) at 25°C for 15 seconds, and then washed with propylene glycol monomethyl ether acetate. When the resin film after development was examined with a metallurgical microscope, no cracks were found and it had excellent photosensitive properties.

[0093]

[0094]

Claims

1. A photosensitive resin composition containing a maleimide compound, a crosslinking agent, and a photopolymerization initiator, wherein the maleimide compound is a reaction product of a tetracarboxylic dianhydride (a1), a diamine (a2), a triamine (a3), and maleic anhydride (a4), the tetracarboxylic dianhydride (a1) includes a tetracarboxylic dianhydride having an aromatic ring, the diamine (a2) includes a dimer diamine and a second diamine other than the dimer diamine, and at least one of the second diamine and the triamine includes an amine having an aromatic ring.

2. The photosensitive resin composition according to claim 1, wherein the tetracarboxylic dianhydride having an aromatic ring contains at least one of pyromellitic dianhydride, 4,4'-oxydiphthalic anhydride, 3,4'-oxydiphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3',3,4'-biphenyltetracarboxylic dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

3. The photosensitive resin composition according to claim 1, wherein the amine having an aromatic ring is a diamine having an aromatic ring, and the diamine having an aromatic ring includes at least one of 4,4'-diamino-2,2'-dimethylbiphenyl, 4,4'-diamino-2,2'-diethylbiphenyl, 4,4'-diamino-3,3'-dimethylbiphenyl, 4,4'-diamino-3,3'-diethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetramethylbiphenyl, 4,4'-diamino-3,3',5,5'-tetraethylbiphenyl, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-diamino-2,2'-dimethoxybiphenyl, and 4,4'-diamino-3,3'-dimethoxybiphenyl.

4. The photosensitive resin composition according to claim 1, wherein the diamine contains at least one of a compound represented by the following general formula (1) and a compound represented by the following general formula (2). [In formulas (1) and (2), m, n, p, and q each represent an integer of 1 or more selected so that m + n = 6 to 17 and p + q = 8 to 19, and the bond indicated by a broken line means a carbon-carbon single bond or a carbon-carbon double bond. However, when the bond indicated by a broken line is a carbon-carbon double bond, formulas (1) and (2) have a structure in which the number of hydrogen atoms bonded to each carbon atom constituting the carbon-carbon double bond is reduced by one from the numbers shown in formulas (1) and (2).] 5. The photosensitive resin composition according to claim 1, wherein the weight average molecular weight of the maleimide compound is 3000 to 40000.

6. The photosensitive resin composition according to claim 1, wherein the crosslinking agent includes a polymerizable crosslinking agent having a (meth)acryloyl group.

7. The photosensitive resin composition according to claim 1, wherein the crosslinking agent includes a polymerizable crosslinking agent having an allyl group or a vinyl group.

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

9. A cured product of the photosensitive resin composition according to any one of claims 1 to 8.

10. A semiconductor device having a rewiring layer comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 8.

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