Photosensitive resin composition, cured object, and semiconductor element

Abstract

A photosensitive resin composition according to the present disclosure comprises a maleimide compound, a crosslinking agent, and a photopolymerization initiator, wherein the maleimide compound is a product of reaction among a tetracarboxylic dianhydride (a1), amines (a2), and maleic anhydride (a3). The amines (a2) comprise a dimer diamine and a second amine which is not a dimer diamine. The tetracarboxylic dianhydride (a1) and / or the amines (a2) include a compound having a biphenyl skeleton.

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 a high glass transition temperature (Tg) while maintaining sufficient microfabrication and dielectric properties. However, increasing the proportion of bulky structures in the polymer to increase the Tg can result in a decrease in photosensitivity (cracks occurring in the patterned resin film after development). Therefore, an object of the present disclosure is to provide a photosensitive resin composition capable of forming an insulating film with excellent photosensitivity.

[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), an amine (a2), and maleic anhydride (a3), the amine (a2) contains a dimer diamine and a second amine other than the dimer diamine, and at least one of the tetracarboxylic dianhydride (a1) and the amine (a2) contains a compound having a biphenyl skeleton. [2] The photosensitive resin composition according to [1] above, wherein the second amine 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. [3] The photosensitive resin composition according to [1] or [2] above, wherein the tetracarboxylic dianhydride (a1) comprises at least one of 3,3',4,4'-biphenyltetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride. [4] The photosensitive resin composition according to any one of [1] to [3] above, wherein the dimer diamine comprises 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 with excellent photosensitivity characteristics, 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), an amine (a2), and maleic anhydride (a3), in which the amine (a2) contains a dimer diamine and a second amine other than the dimer diamine, and at least one of the tetracarboxylic dianhydride (a1) and the amine (a2) contains a compound having a biphenyl skeleton. The biphenyl skeleton 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)"), an amine (a2) (hereinafter also referred to as "component (a2)"), and maleic anhydride (a3) ​​(hereinafter also referred to as "component (a3)"). That is, the component (A) is a maleimide compound obtained by reacting the components (a1), (a2), and (a3). Here, the component (a2) contains a dimer diamine and a second amine other than the dimer diamine. At least one of the component (a1) and the component (a2) contains a compound having a biphenyl skeleton. The component (A) may have multiple maleimide groups in the molecule. The component (A) may be a bismaleimide compound. The component (A) may be used alone or in combination of two or more types.

[0014] Examples of compounds having a biphenyl skeleton include tetracarboxylic dianhydrides such as 3,3',4,4'-biphenyltetracarboxylic dianhydride, and diamines such as 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. The compound having a biphenyl skeleton may be an amine having a biphenyl skeleton.

[0015] The tetracarboxylic dianhydride of component (a1) can be any known polyimide raw material. Examples of component (a1) include pyromellitic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 4,4'-oxydiphthalic anhydride, 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, and 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride. ',4,4'-Benzophenonetetracarboxylic dianhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 1,2,3,4-butanetetracarboxylic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2 ,3,5,6-tetracarboxylic dianhydride, bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid) 1,4-phenylene, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 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 acid acid dianhydride, 3,4'-oxydiphthalic anhydride, 3,4'-biphthalic anhydride, norbornane-2-spiro-α-cyclopentanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, 5,5'-bis-2-norbornene-5,5',6,6'-tetracarboxylic-5,5',6,6'-dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

[0016] From the viewpoint of low dielectric properties or high Tg, the component (a1) is preferably selected from the group consisting of 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-2,3-dione, 2,3-dioxo ... and (iii)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, dicyclohexyl-3,4,3',4'-tetracarboxylic dianhydride, bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid 2,3:5,6-dianhydride, 5,5'-bis-2-norbornene-5,5',6,6'-tetracarboxylic acid-5,5',6,6'-dianhydride, 3,4'-biphthalic anhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride. and 3,3',4,4'-biphenyltetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl] It is more preferable that the compound contains at least one selected from the group consisting of fluorene dianhydrides, and it is even more preferable that the compound contains at least one selected from the group consisting of 3,3',4,4'-biphenyltetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

[0017] The component (a2) contains a dimer diamine (first amine) and a second amine other than the dimer diamine.

[0018] 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):

[0019]

[0020] 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).

[0021] 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.

[0022] Commercially available dimer diamine products include, for example, PRIAMINE 1075 and PRIAMINE 1074 (both manufactured by Croda Japan Co., Ltd.).

[0023] The second amine is an amine that does not fall under the category of the above-mentioned dimer diamine. The second amine may be a diamine or triamine, or may be a diamine. By using an alicyclic diamine as the second amine, the dielectric constant can be further reduced. By using an aromatic diamine as the second amine, the elastic modulus and Tg of the cured product can be improved.

[0024] Examples of the second amine include 1,3-diaminopropane, norbornanediamine, 4,4-methylenedianiline, 1,3-bis[2-(4-aminophenyl)-2-propyl]benzene, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis[4-(4-aminophenoxy)phenyl]fluorene, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, 4,4'-(hexafluoroisopropylidene)dianiline, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0 ２，６]decane, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, isophoronediamine, 4,4'-methylenebis(cyclohexylamine), 4,4'-methylenebis(2-methylcyclohexylamine), 1,1-bis(4-aminophenyl)cyclohexane, 2,7-diaminofluorene, 4,4'-ethylenedianiline, 4,4'-methylenebis(2,6-diethylaniline), 4,4'-methylene Benzenebis(2-ethyl-6-methylaniline), 2,2-bis[4-(4-aminophenoxy)phenyl]propane, bis[4-(4-aminophenoxy)phenyl]methane, 4,4'-bis(4-aminophenoxy)biphenyl, 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'-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'-dimethoxybiphenyl, and 4,4'-diamino-3,3'-dimethoxybiphenyl, (4,4'-diamino)diphenyl ether, (3,3'-diamino)diphenyl ether, paraphenylenediamine, orthophenylenediamine, metaphenylenediamine, bis[4-(3-aminophenoxy)phenyl]sulfone, and bis[4-(4-aminophenoxy)phenyl]sulfone.

[0025] From the viewpoint of photosensitive characteristics and adhesion, the second amine preferably contains 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.

[0026] In component (a2), the molar ratio of the second amine to the total amount of diamine (moles of second amine / (moles of dimer diamine+moles of second amine)) may be 70 mol% or less, or may be 50 mol% or less. When this ratio is 70 mol% or less, the dielectric properties of the cured product can be further reduced.

[0027] By using dimer diamine as the amine, the dielectric properties of the cured product can be reduced. On the other hand, when dimer diamine is used alone as the amine, the elastic modulus and Tg of the cured product decrease. In contrast, by using a second amine in combination with dimer diamine, the elastic modulus and Tg of the cured product can be improved while maintaining the dielectric properties.

[0028] Component (a2) may contain a triamine. Examples of triamines include tris(2-aminomethyl)amine, tris(2-aminoethyl)amine, tris(2-aminopropyl)amine, 2-(aminomethyl)-2-methyl-1,3-propanediamine, trimer triamine, 3,4,4'-triaminodiphenyl ether, 1,2,4-triaminobenzene, 1,3,5-triaminobenzene, 1,2,3-triaminobenzene, 1,3,5-triazine-2,4,6-triamine, 2,4,6-triaminopyrimidine, 1,3,5-tris(4-aminophenyl)benzene, and 1,3,5-tris(4-aminophenoxy)benzene. 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 fewer carbon atoms, are more preferred from the viewpoint of achieving a high Tg.

[0029] At least one of the above-mentioned components (a1) and (a2) contains a compound having a biphenyl skeleton. When at least one of the components (a1) and (a2) constituting the maleimide compound contains a compound having a biphenyl skeleton, a cured product obtained using the maleimide compound has excellent photosensitive properties while sufficiently maintaining a low dielectric constant and a low dielectric loss tangent. From the viewpoint of achieving a high Tg, it is preferable that the component (a2) contains a diamine having a biphenyl skeleton.

[0030] Component (A) can be produced by various known methods. For example, components (a1) and (a2) 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 (a3) ​​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).

[0031] In the imidization reaction or maleimidization reaction, various known reaction catalysts, dehydrating agents, and solvents can be used.

[0032] 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.

[0033] Examples of organic solvents 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; 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 mononitrate. Examples of the organic solvent include glycol ether solvents such as ethylene 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 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 organic solvents can be used alone or in combination of two or more.

[0034] 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).

[0035] The assumed structure of component (A) produced by the above method is shown in the following general formula (4): General formula (4) assumes that the second amine is a diamine.

[0036] In general formula (4), X's each independently represent a tetravalent organic group, Y's each independently represent a divalent organic group, and a represents an integer of 1 or more. However, at least one of the multiple Y's represents a divalent organic group derived from the dimer diamine, and at least one of the multiple Y's represents a divalent organic group derived from the second amine. Furthermore, X and Y may be an organic group having an aliphatic group, an alicyclic structure, or an aromatic ring, and may contain a heteroatom. However, at least one of X and Y represents a tetravalent organic group having a biphenyl skeleton.

[0037] The molecular weight of the (A) component can be controlled by the number of moles of the (a1) component and the (a2) component, and the smaller the number of moles of the (a1) component is relative to the number of moles of the (a2) component, the smaller the molecular weight can be. For the purpose of easily achieving the effects of the present disclosure, the number of moles of the (a1) component per mole of the (a2) component, i.e., [number of moles of the (a1) component] / [number of moles of the (a2) component], is usually in the range of 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.

[0038] 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, 7,500 to 25,000, 8,000 to 23,000, or 8,500 to 20,000. A weight average molecular weight of 40,000 or less results in good solubility in organic solvents, while a weight average molecular weight of 3,000 or more tends to provide a sufficient effect of improving heat resistance. Mw can be measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.

[0039] (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.

[0040] 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.

[0041] Examples of the polymerizable crosslinking agent having a (meth)acryloyl group include di(meth)acrylate compounds having two (meth)acryloyl groups, such as tricyclodecane dimethanol di(meth)acrylate, dioxane glycol di(meth)acrylate, 1,6-hexanediol 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 di(meth)acrylate, polyethylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate; and (meth)acrylate compounds having three or more (meth)acryloyl groups, such as tris-(2-(meth)acryloyloxyethyl)isocyanurate, ethoxylated isocyanuric acid tri(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, dipentaerythritol poly(meth)acrylate, and alkoxylated dipentaerythritol poly(meth)acrylate.

[0042] 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.

[0043] The polymerizable crosslinking agent having a (meth)acryloyl group may contain a di(meth)acrylate compound from the viewpoint of photosensitive properties and dielectric properties. The di(meth)acrylate compound may be 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, or 1,10-decanediol di(meth)acrylate from the viewpoint of photosensitive properties and dielectric properties. The polymerizable crosslinking agent having a (meth)acryloyl group may contain dioxane glycol di(meth)acrylate or dioxane glycol dimethacrylate from the viewpoint of photosensitive properties and dielectric properties.

[0044] 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.

[0045] 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.

[0046] Examples of the polymerizable crosslinking agent having a vinyl group include a polyvinylbenzyl compound and a polyvinylbenzyl ether compound.

[0047] The polymerizable crosslinking agent having an allyl group or a vinyl group may contain 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 contain triallyl isocyanurate from the viewpoint of dielectric properties.

[0048] 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, 6 to 35 parts by mass, 8 to 30 parts by mass, 9 to 25 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.

[0049] (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.

[0050] 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.

[0051] The content of the component (C) may be 0.1 to 10 parts by mass, 0.3 to 9.0 parts by mass, 0.5 to 8.0 parts by mass, 0.8 to 7.0 parts by mass, or 1.0 to 5.0 parts by mass relative to 100 parts by mass of the total amount of the component (A) and the component (B), because excellent micro-processability is easily obtained.

[0052] (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 crosslinking agent. 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.

[0053] 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 ...

[0054] The content of the (D) component is not particularly limited, but may be 0.1 to 10.0 parts by mass, 0.5 to 5.0 parts by mass, 0.6 to 4.0 parts by mass, or 0.7 to 3.0 parts by mass relative to 100 parts by mass of the total amount of the (A) component and the (B) component.

[0055] (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.

[0056] 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.

[0057] The content of the silane coupling agent may be 0.01 to 10 parts by mass, 0.1 to 8.0 parts by mass, 0.2 to 7.0 parts by mass, 0.3 to 6.0 parts by mass, or 0.5 to 5.0 parts by mass, relative to 100 parts by mass of the total amount of the (A) component and the (B) component.

[0058] (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.

[0059] The content of the rust inhibitor may be 0.01 to 10 parts by mass, 0.1 to 5.0 parts by mass, 0.3 to 4.0 parts by mass, or 0.5 to 3.0 parts by mass, relative to 100 parts by mass of the total amount of the components (A) and (B).

[0060] (Polymerization Inhibitor) The photosensitive resin composition according to this embodiment may further contain a polymerization inhibitor from the viewpoint of storage stability.

[0061] 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.

[0062] The content of the polymerization inhibitor may be 0.01 to 10 parts by mass, 0.05 to 5.0 parts by mass, 0.10 to 2.0 parts by mass, or 0.15 to 1.0 parts by mass, relative to 100 parts by mass of the total amount of the components (A) and (B).

[0063] (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.

[0064] 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, and benzyl dimethyl ketone. ethanol, benzyl diethyl ketal, diphenyl disulfide, anthracene, phenanthrenequinone, riboflavin tetrabutylate, acridine orange, erythrosine, 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. One type of sensitizer may be used alone, or two or more types may be used in combination.

[0065] 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 component (A).

[0066] (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.

[0067] 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, and carbitol acetate; and amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide.

[0068] 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 %.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] The present disclosure will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0073] [Synthesis of Maleimide Compound] In order to synthesize a maleimide compound, the following components (a1) to (a3), 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 anhydride (manufactured by Daicel Corporation) BPDA: 3,3',4,4'-biphenyltetracarboxylic dianhydride (manufactured by JFE Chemical Corporation, trade name "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") TAEA: tris(2-aminoethyl)amine (manufactured by Tokyo Chemical Industry Co., Ltd.) (Component (a3)) 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) Toluene (manufactured by Yamaichi Chemical Industry Co., Ltd.) γ-butyrolactone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

[0074] Synthesis Example 1 29.22 parts by mass of 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride (BPAF), 125.71 parts by mass of pseudocumene, 26.95 parts by mass of Solmix A-11, and 29.00 parts by mass of γ-butyrolactone were added to a 0.3 L flask equipped with a condenser, a nitrogen inlet tube, a thermocouple, and a stirrer. After addition, the temperature was raised to 80°C and maintained at that temperature for 0.5 hours. 31.95 parts by mass of dimer diamine (DDA) was added dropwise, and then 5.41 parts by mass of 4,4'-diamino-2,2'-dimethylbiphenyl (mTBHG) was added. After addition, 1.63 parts by mass of an aqueous methanesulfonic acid 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 1 hour. Water and alcohol were removed from the reaction solution, yielding an intermediate polyimide resin. Subsequently, the polyimide resin was cooled to 130°C, and 6.25 parts by mass of maleic anhydride was added. The temperature was raised to 160°C, and a dehydration ring-closing reaction was carried out at 160°C for 4 hours. Water was removed from the reaction solution, yielding a maleimide compound.

[0075] 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).

[0076] Synthesis Examples 2 to 7 Solutions of maleimide compounds (A-2) to (A-7) 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.

[0077] (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.

[0078] (Weight-Average Molecular Weight) The weight-average molecular weight (Mw) of the maleimide compound 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 (GL-R420 x 1, GL-R430 x 1, GL-R440 x 1 (all manufactured by Hitachi High-Tech Fielding Corporation)) heated to 30°C, and measurement was performed using THF as the developing solvent at a flow rate of 1.6 mL / min. The detector used was an L-3350 RI detector (manufactured by Hitachi, Ltd.), and Mw was calculated from the elution time using a molecular weight / elution time curve prepared using standard polystyrene (manufactured by Tosoh Corporation).

[0079]

[0080] 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 "TAIC", manufactured by Mitsubishi Chemical Corporation, number of allyl groups: 3) A-DOD-N: 1,10-decanediol diacrylate (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.) DOD-N: 1,10-decanediol dimethacrylate (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.) A-DOG: Dioxane glycol diacrylate (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0081] 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.)

[0082] [Photosensitive Resin Composition] Each component in the formulation amount (parts by mass, solid content) shown in Table 2 was mixed with 210 parts by mass of a solvent, stirred at 25°C for 30 minutes or more, and then filtered through a filter with a 0.5 μm mesh size to prepare the photosensitive resin compositions of Examples 1 to 6. Each component in the formulation amount (parts by mass, solid content) shown in Table 3 was mixed with 210 parts by mass of a solvent, stirred at 25°C for 30 minutes or more, and then filtered through a filter with a 0.5 μm mesh size to prepare the photosensitive resin compositions of Examples 7 to 9.

[0083] 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 (MA-20, manufactured by Mikasa Co., Ltd.) was used to expose the film to an exposure dose of 1000 mJ / cm. ２The pattern was exposed to light under these conditions to form a 10 mm wide resin film, and then heated at 100°C for 1 minute. The exposed resin film was developed (immersed) in 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 to a length of 50 mm, 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.

[0084] (Photosensitive Properties) A ​​photosensitive resin composition was spin-coated onto 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) and then heated at 100°C for 1 minute. The silicon wafer on which the exposed resin film had been formed was developed (immersed) in a developer (a mixed solution of cyclopentanone and propylene glycol monomethyl ether acetate) at 25°C for 15 seconds, and then washed with propylene glycol monomethyl ether acetate. The resin film after development was checked for the presence or absence of cracks using a metallurgical microscope. Cases in which no defects were found were evaluated as "A," and cases in which defects were found were evaluated as "B."

[0085] (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. ２The 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 was formed was heated at 200°C for 2 hours in a nitrogen atmosphere, forming a 5 μm thick cured film on the silicon wafer. The silicon wafer on which the cured film was formed was placed in an environment of 121°C and 100% humidity for 100 hours, and a pressure cooker test (PCT test) was performed. After the test, a cross-cut guide (manufactured by Cortec Co., Ltd., product name "CCJ-1") and a cutter (NT cutter eA-300) were used to make 11 incisions vertically and horizontally at 1 mm intervals in the cured film, creating 100 grids. Cellophane tape (manufactured by Nichiban Co., Ltd., product name "CT1535") was firmly pressed onto the grid portions, 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 Table 2.

[0086]

[0087]

Claims

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

2. The photosensitive resin composition according to claim 1, wherein the second amine 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.

3. The photosensitive resin composition according to claim 1, wherein the tetracarboxylic dianhydride (a1) contains at least one of 3,3',4,4'-biphenyltetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-C]furan-1,3-dione, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride.

4. The photosensitive resin composition according to claim 1, 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 more selected such 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)] 5. The photosensitive resin composition according to claim 1, wherein the maleimide compound has a weight average molecular weight of 3,000 to 40,000.

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

7. The photosensitive resin composition according to claim 1, wherein the crosslinking agent comprises 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.