Resin composition, cured film, and semiconductor device

Abstract

A resin composition containing at least a resin (A) and a compound (B), the compound (B) being a compound represented by formula (1) and / or a compound represented by formula (2). Provided is a resin composition having little change in viscosity (In formula (1) and formula (2), R1 to R8 each independently represent a group selected from the group consisting of a hydrogen atom, an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group, and an organic group having 1 to 20 carbon atoms. ). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a resin composition, a cured film using the same, and a semiconductor device. Background Art

[0002] Heat-resistant resins such as polyimide, polybenzoxazole, polyamide-imide have excellent heat resistance and electrical insulation. Therefore, the resin composition containing these heat-resistant resins can be used for the surface protection layer of semiconductor elements such as LSI, interlayer insulating layer, insulating layer of organic electroluminescence and organic EL display element, flattening layer of TFT substrate for display device, etc. In recent years, along with the light and short miniaturization of electronic equipment, the high refinement of display element, the miniaturization and high integration of semiconductor device are constantly developed. Therefore, in the materials used in these insulating films or protective films, various technical problems are generated. Among these, the viscosity change caused by long-term storage is particularly problematic. When the resin composition with a long storage time and a change in viscosity is applied, the problem of being unable to be applied according to the target film thickness often occurs.

[0003] Therefore, as a method for suppressing the change in viscosity, a method of using a specific type of solvent in a resin composition has been proposed (for example, see Patent Document 1). However, this method is still insufficient in view of the importance of dimensional accuracy accompanying the miniaturization of semiconductor devices.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2011 / 001493 Summary of the invention

[0007] Problems to be solved by the invention

[0008] Therefore, an object of the present invention is to provide a resin composition having a small viscosity change.

[0009] Means for solving problems

[0010] The inventors of the present application have conducted intensive studies and, as a result, have found that the change in viscosity during long-term storage can be suppressed by using a compound having a specific chemical structure, thereby completing the present invention.

[0011] That is, in order to achieve the above-mentioned object, the present invention mainly adopts the following configurations.

[0012] [1] A resin composition comprising at least a resin (A) and a compound (B), wherein the compound (B) is a compound represented by formula (1) and / or a compound represented by formula (2).

[0013] [Chemical formula 1]

[0014]

[0015] (In formula (1) and formula (2), R 1 ~R 8 Each independently represents a group selected from the group consisting of a hydrogen atom, an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group, and an organic group having 1 to 20 carbon atoms.

[0016] [2] The resin composition according to [1], wherein the resin (A) contains at least one selected from the group consisting of polyimide, polybenzoxazole, polyamideimide, and precursors thereof.

[0017] [3] The resin composition according to [1] or [2], wherein the compound represented by the formula (1) and the compound represented by the formula (2) are respectively the compound represented by the formula (3) and the compound represented by the formula (4).

[0018] [Chemical formula 2]

[0019]

[0020] [4] The resin composition according to any one of [1] to [3], wherein the content of the compound (B) is 0.01 to 0.25% by weight relative to 100% by weight of the resin composition.

[0021] [5] The resin composition according to any one of [1] to [4], wherein the compound (B) is a compound represented by formula (1) and a compound represented by formula (2).

[0022] [6] The resin composition according to [5], wherein the content ratio of the compound represented by the above formula (1) to the compound represented by the formula (2) is 100 to 2,000 parts by weight of the compound represented by the formula (2) per 100 parts by weight of the compound represented by the formula (1).

[0023] [7] The resin composition according to any one of [1] to [6], further comprising at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone.

[0024] [8] The resin composition according to [7], wherein the content of the additive (C) is 0.01 to 0.25% by weight relative to 100% by weight of the resin composition.

[0025] [9] The resin composition according to any one of [1] to [8], comprising morpholine.

[0026]

[10] The resin composition according to [9], wherein the content of morpholine is 0.01 to 0.05% by weight relative to 100% by weight of the resin composition.

[0027]

[11] The resin composition according to [9] or

[10] , wherein the content ratio of the compound (B) to morpholine is 5 to 20 parts by weight of morpholine per 100 parts by weight of the compound (B).

[0028]

[12] A cured film of the resin composition according to any one of [1] to

[11] .

[0029]

[13] A semiconductor device comprising the cured film according to

[12] .

[0030] Effects of the Invention

[0031] According to the present invention, a resin composition having a small change in viscosity after long-term storage can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] [ Figure 1 ] is a diagram showing an enlarged cross-section of a pad portion of a semiconductor device having a bump.

[0033] [ Figure 2 ] is a diagram showing a detailed method for manufacturing a semiconductor device having bumps.

[0034] [ Figure 3 ] is a cross-sectional view of a manufacturing process of an example of a semiconductor device having a cured film of the present invention.

[0035] [ Figure 4 ] is a diagram showing a method for manufacturing a semiconductor device in RDL-first.

[0036] [ Figure 5 ] is a cross-sectional view of a coil component of an inductor device as an example of a semiconductor device of the present invention.

[0037] [ Figure 6 ] is a cross-sectional view of an example of a TFT substrate. DETAILED DESCRIPTION

[0038] Embodiments of the present invention will be described in detail.

[0039] <Resin (A)>

[0040] The resin composition of the present invention contains a resin (A). Examples of the resin (A) include, but are not limited to, polymers of free radical polymerizable monomers, polyurethanes, polyureas, polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, polyamide-imides, polyamide-imide precursors, polyamides, phenolic resins, epoxy resins, and the like. The resin composition may contain two or more of these resins.

[0041] The resin (A) of the present invention may be alkali-soluble. The alkali-soluble in the present invention means that: a solution obtained by dissolving the resin in γ-butyrolactone is applied to a silicon wafer, and pre-baked at 120° C. for 4 minutes to form a pre-baked film with a film thickness of 10 μm±0.5 μm, and the pre-baked film is immersed in a 2.38 wt% tetramethylammonium hydroxide aqueous solution at 23±1° C. for 1 minute, and then rinsed with pure water, and the dissolution rate obtained based on the reduction in film thickness at this time is 50 nm / minute or more.

[0042] In order to impart alkali solubility to the resin (A), a group such as a carboxyl group, a sulfonic acid group or a hydroxyl group may be introduced into the resin (A).

[0043] From the viewpoint of heat resistance, the resin (A) of the present invention is preferably polyimide, polybenzoxazole, polyamide-imide, any of their precursors or a copolymer selected from two or more thereof, more preferably polyimide, polyimide precursor, polybenzoxazole precursor or a copolymer selected from two or more thereof. In addition, from the viewpoint of the ease of synthesis, it is particularly preferably a polyimide precursor. Herein, a polyimide precursor refers to a resin converted to polyimide by heat treatment, chemical treatment, for example, polyamic acid, polyamic acid esters, etc. can be cited. A polybenzoxazole precursor refers to a resin converted to polybenzoxazole by heat treatment, chemical treatment, for example, polyhydroxyamides, etc. can be cited.

[0044] The polyimide precursor and polybenzoxazole precursor have a structural unit represented by the following formula (5), and the polyimide has a structural unit represented by the following formula (6). Two or more of these may be contained, and a resin obtained by copolymerizing the structural unit represented by formula (5) and the structural unit represented by formula (6) may be contained.

[0045] [Chemical formula 3]

[0046]

[0047] (In formula (5), X represents a 2- to 8-valent organic group, and Y represents a 2- to 11-valent organic group. R 9 and R 11 represents a hydroxyl group or a sulfonic acid group, each of which may be a single group or different groups may be present in mixture. 10 and R 12represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. r, s and u represent integers of 0 to 3, and t represents an integer of 0 to 6. However, r+s+t+u>0.

[0048] [Chemical formula 4]

[0049]

[0050] (In formula (6), E represents a 4- to 10-valent organic group, and G represents a 2- to 8-valent organic group. R 13 and R 14 represents a carboxyl group, a sulfonic acid group or a hydroxyl group. 13 and R 14 They may be the same or different. p and q each independently represent an integer of 0 to 6.

[0051] The polyimide, polyimide precursor, polybenzoxazole precursor or a copolymer of two or more thereof preferably has 5 to 100,000 structural units represented by formula (5) or (6). In addition to the structural units represented by formula (5) or (6), other structural units may be present. In this case, it is preferred that the structural units represented by formula (5) or (6) account for 50 mol% or more of all the structural units.

[0052] In the above formula (5), X(R 9 )r(COOR 10 )s represents an acid residue. X is a divalent to octavalent organic group, and preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cyclic aliphatic group.

[0053] Examples of the acid residue include residues of dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid; residues of tricarboxylic acids such as trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid; pyromellitic acid, 3,3',4,4'-biphenyl tetracarboxylic acid, 2,3,3',4'-biphenyl tetracarboxylic acid, 2,2',3,3'-biphenyl tetracarboxylic acid, 3,3',4,4'-benzophenone tetracarboxylic acid, 2,2',3,3'-benzophenone tetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3- The polyimide precursor and the polybenzoxazole precursor may have two or more of these residues.

[0054] [Chemical formula 5]

[0055]

[0056] (R 15 represents an oxygen atom, C(CF3)2 or C(CH3)2. 16 and R 17 Each independently represents a hydrogen atom or a hydroxyl group. )

[0057] In the case of a tricarboxylic acid residue or a tetracarboxylic acid residue among the above acid residues, one or two carboxyl groups correspond to (COOR 10 ).

[0058] In the above formula (6), E(R 13 )p represents a residue of an acid dianhydride. E is a tetravalent to devalent organic group, and among them, an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cyclic aliphatic group is preferred.

[0059] Specific examples of the acid dianhydride residue include pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, and bis(2,3-dicarboxyphenyl)methane dianhydride. , bis(3,4-dicarboxyphenyl)ether dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis{4-(3,4-dicarboxyphenoxy)phenyl}fluorene dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, and the acid dianhydride of the structure shown below, the residue of aliphatic tetracarboxylic dianhydride such as butanetetracarboxylic dianhydride, the residue of aliphatic tetracarboxylic dianhydride containing a cyclic aliphatic group such as 1,2,3,4-cyclopentanetetracarboxylic dianhydride, etc. The polyimide precursor and the polybenzoxazole precursor may have two or more of them.

[0060] [Chemical formula 6]

[0061]

[0062] (R 15 represents an oxygen atom, C(CF3)2 or C(CH3)2. 16 and R 17 Each independently represents a hydrogen atom or a hydroxyl group. )

[0063] In the above formula (5), Y(R 11 )t(COOR 12 )u and G(R 14 )q represents a diamine residue. Y is a 2- to 11-valent organic group, and G is a 2- to 8-valent organic group, preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cyclic aliphatic group.

[0064] Specific examples of the diamine residue include the following aromatic diamines, aliphatic diamines containing a cyclic aliphatic group such as cyclohexyl diamine and methylenebiscyclohexylamine, and residues of diamines having the following structures. These aromatic diamines include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1,4-bis(4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl}ether, 1,4-bis(4-aminophenoxy)benzene, 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-diethyl-4, 4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-diethyl-4,4'-diaminobiphenyl, 2,2',3,3'-tetramethyl-4,4'-diaminobiphenyl, 3,3',4,4'-tetramethyl-4,4'-diaminobiphenyl, 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 2,2'-bis(trifluoromethyl)-5,5'-dihydroxybenzidine, 3,3'-diaminodiphenyl sulfone, 4,4'diaminodiphenyl sulfone, 3,5-diaminobenzoic acid, 3,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, compounds in which at least a part of hydrogen atoms of the aromatic rings are substituted with alkyl groups or halogen atoms, etc. The polyimide precursor and the polybenzoxazole precursor may have two or more of these.

[0065] [Chemical formula 7]

[0066]

[0067] (R 15 represents an oxygen atom, C(CF3)2 or C(CH3)2. 16 ~R 19 Each independently represents a hydrogen atom or a hydroxyl group. )

[0068] Furthermore, by capping the ends of these resins with monoamines, acid anhydrides, acid chlorides, monocarboxylic acids, or active ester compounds having an acidic group, a resin having an acidic group at the main chain terminal can be obtained.

[0069] Preferred examples of the monoamine having an acidic group include 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminothiophenol, 3-aminothiophenol, and 4-aminothiophenol. The polyimide precursor and the polybenzoxazole precursor may be terminated by using two or more of them.

[0070] Preferred examples of the acid anhydride include phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride, 3-hydroxyphthalic anhydride, etc. The polyimide precursor and the polybenzoxazole precursor may be terminated using two or more of these.

[0071] Preferred examples of monocarboxylic acids include 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, etc. The polyimide precursor and the polybenzoxazole precursor may be end-capped using two or more of these.

[0072] Preferred examples of the acid chloride include monoacyl chloride compounds obtained by chlorinating the carboxyl group of the monocarboxylic acid, monoacyl chloride compounds obtained by chlorinating only one carboxyl group of dicarboxylic acids such as terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, and 2,6-dicarboxynaphthalene, etc. The polyimide precursor and the polybenzoxazole precursor may be end-capped using two or more of these.

[0073] Preferred examples of the active ester compound include products of the above-mentioned monoacyl chloride compound with N-hydroxybenzotriazole, N-hydroxy-5-norbornene-2,3-dicarboxylic imide, etc. Two or more of these may be used.

[0074] The end-capping agent introduced into the resin can be easily detected by the following method. For example, the resin into which the end-capping agent is introduced is dissolved in an acidic solution and decomposed into amine components and acid components which are structural units of the resin. The end-capping agent can be easily detected by subjecting the resin to gas chromatography (GC) and NMR measurement. In addition, the end-capping agent can also be detected by subjecting the resin into which the end-capping agent is introduced to pyrolysis gas chromatography (PGC), infrared spectroscopy and 13 C-NMR spectroscopy was used for detection.

[0075] <Method for producing resin (A)>

[0076] The resin (A) in the present invention is synthesized by a known method.

[0077] As a method for producing a polyamic acid as a polyimide precursor, there is exemplified a method of reacting a tetracarboxylic dianhydride and a diamine compound in a solvent at low temperature.

[0078] Regarding the method for producing polyamic acid esters which are also polyimide precursors, in addition to the method of reacting the polyamic acid with an esterifying agent described above, there can be cited: a method of obtaining a diester by tetracarboxylic dianhydride and an alcohol, and then reacting with an amine in a solvent in the presence of a condensing agent; a method of obtaining a diester by tetracarboxylic dianhydride and an alcohol, and then chlorinating the remaining dicarboxylic acid and reacting with an amine in a solvent, and the like. From the viewpoint of ease of synthesis, it is preferred to include a step of reacting the polyamic acid with an esterifying agent. As an esterifying agent, there is no particular limitation, and a known method can be applied. From the perspective of ease of purification of the obtained resin, N,N-dimethylformamide dialkyl acetal is preferred.

[0079] Regarding the method for producing polyhydroxyamide as a precursor of polybenzoxazole, for example, there can be mentioned a method of condensing a bisaminophenol compound with a dicarboxylic acid in a solvent. Specifically, for example, there can be mentioned a method of reacting a dehydration condensation agent such as dicyclohexylcarbodiimide (DCC) with an acid and adding a bisaminophenol compound thereto; a method of dripping a dicarboxylic acid dichloride solution into a solution of a bisaminophenol compound to which a tertiary amine such as pyridine has been added, etc.

[0080] Examples of the method for producing polyimide include a method of subjecting the polyamic acid or polyamic acid ester obtained by the above method to dehydration ring closure in a solvent, etc. Examples of the dehydration ring closure method include chemical treatment with an acid, an alkali, etc., and heat treatment.

[0081] Examples of the method for producing polybenzoxazole include a method of subjecting the polyhydroxyamide obtained by the above method to dehydration ring closure in a solvent, etc. Examples of the method for dehydration ring closure include chemical treatment with an acid, an alkali, etc., and heat treatment.

[0082] Examples of the polyamideimide precursor include polymers of tricarboxylic acid, corresponding tricarboxylic anhydride, tricarboxylic anhydride halide and diamine compounds, preferably polymers of trimellitic anhydride chloride and aromatic diamine compounds. Examples of the method for producing the polyamideimide precursor include a method of reacting tricarboxylic acid, corresponding tricarboxylic anhydride, tricarboxylic anhydride halide and diamine compounds in a solvent at low temperature.

[0083] Examples of the method for producing polyamide-imide include a method of reacting trimellitic anhydride with an aromatic diisocyanate in a solvent, a method of subjecting a polyamide-imide precursor obtained by the aforementioned method to dehydration ring closure in a solvent, etc. Examples of the dehydration ring closure method include chemical treatment with an acid, an alkali, etc., and heat treatment.

[0084] The method for producing the resin (A) in the present invention may include a polymerization solvent. Examples of the solvent include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether and propylene glycol monomethyl ether, alkyl acetates such as propyl acetate, butyl acetate, and isobutyl acetate, ketones such as methyl isobutyl ketone and methyl propyl ketone, alcohols such as butanol and isobutyl alcohol, ethyl lactate, butyl lactate, dipropylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol diethyl ether, 3-methoxybutyl acetate, ethylene glycol monoethyl ether acetate, γ-butyrolactone, N-methyl-2-pyrrolidone, diacetone alcohol, N-cyclohexyl-2-pyrrolidone, Pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, propylene glycol monomethyl ether acetate, N,N-dimethyl isobutyric acid amide, 1,3-dimethyl-2-imidazolidinone, N,N-dimethylpropylene urea, δ-valerolactone, 2-phenoxyethanol, 2-pyrrolidone, 2-methyl-1,3-propanediol, triacetin, butyl benzoate, cyclohexylbenzene, dicyclohexane, o-nitroanisole, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, N-(2-hydroxyethyl)-2-pyrrolidone, etc.

[0085] As the polymerization solvent, it is preferable to contain at least one of γ-butyrolactone and N-methyl-2-pyrrolidone. By containing these solvents, the solubility of the resin in the solvent can be improved.

[0086] <Compound (B)>

[0087] The resin composition of the present invention contains a compound (B) represented by the following formula (1) and / or the following formula (2). By containing the compound (B), the viscosity change of the resin composition of the present invention during long-term storage can be suppressed.

[0088] [Chemical formula 8]

[0089]

[0090] (In formula (1) and formula (2), R 1 ~R 8 Each independently represents a hydrogen atom or a group selected from the group consisting of an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group and an organic group having 1 to 20 carbon atoms.

[0091] Examples of the compound represented by formula (1) include 4-pyrroline-2-one, 1-methyl-4-pyrroline-2-one, 1-ethyl-4-pyrroline-2-one, 1-propyl-4-pyrroline-2-one, 1-butyl-4-pyrroline-2-one, 1-vinyl-4-pyrroline-2-one, 5-methyl-4-pyrroline-2-one, 5-ethyl-4-pyrroline-2-one, 5-propyl-4-pyrroline-2-one, 5-butyl-4-pyrroline-2-one, 5- Vinyl-4-pyrroline-2-one, 4-methyl-4-pyrroline-2-one, 4-ethyl-4-pyrroline-2-one, 4-propyl-4-pyrroline-2-one, 4-butyl-4-pyrroline-2-one, 4-vinyl-4-pyrroline-2-one, 3-methyl-4-pyrroline-2-one, 3-ethyl-4-pyrroline-2-one, 3-propyl-4-pyrroline-2-one, 3-butyl-4-pyrroline-2-one, 3-vinyl-4-pyrroline-2-one, 1 ,5-dimethyl-4-pyrroline-2-one, 1-methyl-5-ethyl-4-pyrroline-2-one, 1-methyl-5-propyl-4-pyrroline-2-one, 1-methyl-5-butyl-4-pyrroline-2-one, 1-methyl-5-vinyl-4-pyrroline-2-one, 1,4-dimethyl-4-pyrroline-2-one, 1-methyl-4-ethyl-4-pyrroline-2-one, 1-methyl-4-propyl-4-pyrroline-2-one, 1-methyl-4-butyl-4 -pyrroline-2-one, 1-methyl-4-vinyl-4-pyrroline-2-one, 1,3-dimethyl-4-pyrroline-2-one, 1-methyl-3-ethyl-4-pyrroline-2-one, 1-methyl-4-propyl-4-pyrroline-2-one, 1-methyl-4-butyl-4-pyrroline-2-one, 1-methyl-4-vinyl-4-pyrroline-2-one, 3,5-dimethyl-4-acetyl-4-pyrroline-2-one, etc., and two or more thereof may be contained.

[0092] Examples of the compound represented by formula (2) include 3-pyrroline-2-one, 1-methyl-3-pyrroline-2-one, 1-ethyl-3-pyrroline-2-one, 1-propyl-3-pyrroline-2-one, 1-butyl-3-pyrroline-2-one, 1-vinyl-3-pyrroline-2-one, 5-methyl-3-pyrroline-2-one, 5-ethyl-3-pyrroline-2-one, 5-propyl-3-pyrroline-2-one, 5-butyl-3-pyrroline-2-one, 5-vinyl-3-pyrroline-2-one, -3-pyrroline-2-one, 4-methyl-3-pyrroline-2-one, 4-ethyl-3-pyrroline-2-one, 4-propyl-3-pyrroline-2-one, 4-butyl-3-pyrroline-2-one, 4-vinyl-3-pyrroline-2-one, 3-methyl-3-pyrroline-2-one, 3-ethyl-3-pyrroline-2-one, 3-propyl-3-pyrroline-2-one, 3-butyl-3-pyrroline-2-one, 3-vinyl-3-pyrroline-2-one, 1,5-dimethyl -3-pyrroline-2-one, 1-methyl-5-ethyl-3-pyrroline-2-one, 1-methyl-5-propyl-3-pyrroline-2-one, 1-methyl-5-butyl-3-pyrroline-2-one, 1-methyl-5-vinyl-3-pyrroline-2-one, 1,4-dimethyl-3-pyrroline-2-one, 1-methyl-4-ethyl-3-pyrroline-2-one, 1-methyl-4-propyl-3-pyrroline-2-one, 1-methyl-4-butyl-3-pyrroline-2-one, 1-methyl-4-vinyl-3-pyrroline-2-one, 1,3-dimethyl-3-pyrroline-2-one, 1-methyl-3-ethyl-3-pyrroline-2-one, 1-methyl-4-propyl-3-pyrroline-2-one, 4-methoxy-3-pyrroline-2-one, 1-methyl-4-butyl-3-pyrroline-2-one, 1-methyl-4-vinyl-3-pyrroline-2-one, 3-ethyl-4-methyl-3-pyrroline-2-one, etc., and two or more thereof may be contained.

[0093] Among these, from the viewpoint of suppressing viscosity change, compound (B) is preferably a compound represented by formula (3), i.e., 1-methyl-4-pyrroline-2-one and / or a compound represented by formula (4), i.e., 1-methyl-3-pyrroline-2-one, and more preferably a compound represented by formula (3), i.e., 1-methyl-4-pyrroline-2-one and a compound represented by formula (4), i.e., 1-methyl-3-pyrroline-2-one.

[0094] [Chemical formula 9]

[0095]

[0096] In the present invention, from the viewpoint of suppressing viscosity change, the content of compound (B) is preferably 0.01% by weight or more, more preferably 0.10% by weight or more, relative to 100% by weight of the resin composition. In addition, from the same viewpoint, it is preferably 0.25% by weight or less, more preferably 0.20% by weight or less, relative to 100% by weight of the resin composition.

[0097] In the present invention, from the viewpoint of suppressing viscosity change, compound (B) is preferably a compound represented by formula (1) and a compound represented by formula (2). Furthermore, in terms of its content, from the viewpoint of suppressing viscosity change, the compound represented by formula (2) is preferably 100 parts by weight or more relative to 100 parts by weight of the compound represented by formula (1). Similarly, from the viewpoint of suppressing viscosity change, the amount of formula (2) is preferably 2,000 parts by weight or less, and more preferably 1,100 parts by weight or less relative to 100 parts by weight of the compound represented by formula (1).

[0098] <Additives (C)>

[0099] From the viewpoint of suppressing viscosity change, the resin composition of the present invention preferably contains at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone.

[0100] In the present invention, from the viewpoint of suppressing viscosity change, the content of the additive (C) is preferably 0.01% by weight or more relative to 100% by weight of the resin composition. In addition, from the same viewpoint, it is preferably 0.25% by weight or less, more preferably 0.20% by weight or less relative to 100% by weight of the resin composition.

[0101] <Morpholine>

[0102] From the viewpoint of suppressing a change in viscosity, the resin composition of the present invention preferably contains morpholine.

[0103] In the present invention, from the viewpoint of suppressing viscosity change, the content of morpholine is preferably more than 0.01 wt %, more preferably more than 0.03 wt % relative to 100 wt % of resin combination. In addition, from the same viewpoint, it is preferably below 0.05 wt %, more preferably below 0.04 wt % relative to 100 wt % of resin combination.

[0104] Furthermore, in the present invention, from the viewpoint of suppressing viscosity change, the content of morpholine is preferably 5 parts by weight or more relative to 100 parts by weight of compound (B). In addition, from the same viewpoint, it is preferably 20 parts by weight or less relative to 100 parts by weight of compound (B).

[0105] <Photosensitive Compound>

[0106] The resin composition of the present invention may contain a photosensitive compound and can be a photosensitive resin composition. Examples of the photosensitive compound include a photoacid generator and a photopolymerization initiator. A photoacid generator is a compound that generates an acid by light irradiation, and a photopolymerization initiator is a compound that generates a bond cleavage and / or a reaction by exposure to light to generate free radicals.

[0107] By containing a photoacid generator, acid is generated in the light-irradiated part, and the solubility of the light-irradiated part in the alkaline aqueous solution is increased, so that a positive relief pattern in which the light-irradiated part is dissolved can be obtained. In addition, by containing a photoacid generator and an epoxy compound or a thermal crosslinking agent described later, the acid generated in the light-irradiated part promotes the crosslinking reaction of the epoxy compound and the thermal crosslinking agent, so that a negative relief pattern in which the light-irradiated part is insoluble can be obtained. On the other hand, by containing a photopolymerization initiator and a free radical polymerizable compound described later, free radical polymerization is carried out in the light-irradiated part, so that a negative relief pattern in which the light-irradiated part is insoluble can be obtained.

[0108] Examples of the photoacid generator include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, iodonium salts, etc. Two or more photoacid generators may be contained.

[0109] Examples of the photopolymerization initiator include benzyl ketal photopolymerization initiators, α-hydroxyketone photopolymerization initiators, α-aminoketone photopolymerization initiators, acylphosphine oxide photopolymerization initiators, oxime ester photopolymerization initiators, acridine photopolymerization initiators, titanocene photopolymerization initiators, benzophenone photopolymerization initiators, acetophenone photopolymerization initiators, aromatic ketoester photopolymerization initiators, and benzoate photopolymerization initiators. Two or more photopolymerization initiators may be contained.

[0110] <Radical polymerizable compound>

[0111] The resin composition of the present invention may further contain a radical polymerizable compound.

[0112] A free radical polymerizable compound refers to a compound having a plurality of ethylenically unsaturated double bonds in the molecule. During exposure, the free radicals generated by the aforementioned photopolymerization initiator allow free radical polymerization of the free radical polymerizable compound to proceed, so that the light irradiated portion is insolubilized, thereby obtaining a negative pattern. In addition, by containing a free radical polymerizable compound, the photocuring of the light irradiated portion is promoted, and the sensitivity can be further improved. In addition, the crosslinking density after thermal curing is increased, so the hardness of the cured film can be increased.

[0113] <Thermal crosslinking agent>

[0114] The resin composition of the present invention may further contain a thermal crosslinking agent. A thermal crosslinking agent refers to a compound having at least two thermally reactive functional groups such as alkoxymethyl, hydroxymethyl, epoxy, oxetanyl, etc. in the molecule. By containing a thermal crosslinking agent, the resin (A) or other added components can be crosslinked to improve the heat resistance, chemical resistance and hardness of the film after thermal curing. These thermal crosslinking agents can be combined to contain two or more.

[0115] <Solvent>

[0116] The resin composition of the present invention may contain a solvent. By containing a solvent, it can be made into a varnish state and coating properties can be improved.

[0117] Examples of the solvent include polar aprotic solvents such as γ-butyrolactone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, and dipropylene glycol monomethyl ether. , dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tetrahydrofuran, dioxane and other ethers, acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, diacetone alcohol and other ketones, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate , propylene glycol monoethyl ether acetate, esters such as ethyl lactate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, acetic acid Isopropyl, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutyrate and other esters, toluene, xylene and other aromatic hydrocarbons, N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amides, etc. Two or more of these may be contained.

[0118] <Adhesion Improver>

[0119] Resin combination of the present invention can also contain a close fit improver. As a close fit improver, silane coupling agents such as vinyl trimethoxy silane, vinyl triethoxy silane, epoxy cyclohexyl ethyl trimethoxy silane, 3-glycidoxy propyl trimethoxy silane, 3-glycidoxy propyl triethoxy silane, p-phenyl trimethoxy silane, 3-aminopropyl trimethoxy silane, 3-aminopropyl triethoxy silane, N-phenyl-3-aminopropyl trimethoxy silane, titanium chelate, aluminum chelate, compounds obtained by reacting aromatic amine compounds with alkoxy-containing silicon compounds, etc. can be enumerated. Two or more of them can be contained. By containing these close fit improvers, the developing close fit of base substrates such as silicon wafer, ITO, SiO2, silicon nitride can be improved when the resin film is developed. In addition, the tolerance to the oxygen plasma and UV ozone treatment used in cleaning, etc. can be improved.

[0120] <Surfactant>

[0121] The resin composition of the present invention can further contain a surfactant as needed to improve wettability with a substrate. As a surfactant, for example, Dow Corning Toray (strain) SH series, SD series, ST series, BYK-Chemie Japan (strain) BYK series, Shin-Etsu Chemical Industry (strain) KP series, NOF (strain) Disfoam series, DIC (strain) "Megafac" (registered trademark) series, Sumitomo 3M (strain) Fluorad series, Asahi Glass (strain) "Surflon" (registered trademark) series, "Asahi Guard" (registered trademark) series, Omnova Solutions company Polyfox series and other fluorine-based surfactants, Kyoeisha Chemical (strain) Polyflow series, Kusumoto Chemical (strain) "Disparlon" (registered trademark) series and other acrylic and / or methacrylic surfactants can be cited.

[0122] <Inorganic particles>

[0123] The resin composition of the present invention may further contain inorganic particles. Preferred specific examples of inorganic particles include silicon oxide, titanium oxide, barium titanate, aluminum oxide, talc, etc. The primary particle size of the inorganic particles is preferably 100 nm or less, more preferably 60 nm or less.

[0124] <Thermal Acid Generator>

[0125] The resin composition of the present invention may further contain a thermal acid generator. The thermal acid generator generates an acid by heating, which promotes the crosslinking reaction of the thermal crosslinking agent. In addition, when the resin of the component (A) has an unclosed imide ring structure or an oxazole ring structure, it can promote their cyclization, thereby further improving the mechanical properties of the cured film.

[0126] <Method for producing resin composition>

[0127] Next, the method for producing the resin composition of the present invention is described. For example, the resin composition can be obtained by dissolving the resin (A), the compound (B), and the additive (C) added as needed, morpholine, a photosensitive compound, a radical polymerizable compound, a thermal crosslinking agent, other solvents, a close fit improver, a surfactant, inorganic particles, a thermal acid generator, etc.

[0128] Alternatively, the following resin solution may be used instead of the above-mentioned resin (A), wherein the resin solution is obtained by using a solvent containing a compound (B) as a polymerization solvent for the resin (A). As a dissolving method, stirring and heating may be mentioned. In the case of heating, the heating temperature is preferably set within a range that does not damage the performance of the resin composition, and is usually room temperature to 80°C. In addition, the dissolution order of the components is not particularly limited, and for example, a method of dissolving in sequence from compounds with low solubility may be mentioned. In addition, for components such as surfactants and a part of the close fit improver that are prone to generate bubbles when stirred and dissolved, poor dissolution of other components caused by the generation of bubbles can be prevented by adding them last after dissolving other components.

[0129] The obtained resin composition is preferably filtered using a filter to remove dirt and particles. The filter pore size is, for example, 0.5 μm, 0.2 μm, 0.1 μm, 0.07 μm, 0.05 μm, 0.02 μm, etc., but is not limited to these. The material of the filter includes polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), etc., preferably polyethylene and nylon.

[0130] <Cured Film>

[0131] The cured film of the present invention can be obtained by curing the above-mentioned resin composition.

[0132] The curing conditions are as long as heat treatment is performed to allow the thermal crosslinking reaction to proceed. The heat treatment can be performed by heating in stages or by continuously heating. The heat treatment is preferably performed for 5 minutes to 5 hours. As an example, an example of heat treatment at 140°C for 30 minutes and then further heat treatment at 320°C for 60 minutes can be cited. As the heat treatment conditions, it is preferably above 140°C and below 400°C. In order to allow the thermal crosslinking reaction to proceed, the heat treatment conditions are preferably above 140°C, and more preferably above 160°C. In addition, in order to provide an excellent cured film and improve the yield, the heat treatment conditions are preferably below 400°C, and more preferably below 350°C.

[0133] Next, a method for producing a cured film using the resin composition of the present invention, a resin film formed from the resin composition, or a resin sheet will be described.

[0134] It should be noted that, herein, the so-called resin film is defined as a film obtained by coating the resin composition of the present invention on a substrate and drying. A resin sheet is defined as a sheet obtained by coating a resin composition on a removable substrate and drying. In addition, a cured film is defined as a resin film or a film obtained by curing a resin sheet.

[0135] The method for producing a cured film of the present invention is a method for producing a cured film comprising the following steps: a step of applying the above-mentioned resin composition on a substrate, or laminating a resin sheet on a substrate, and drying to form a resin film; an exposure step of exposing the resin film when it has photosensitivity; a development step of developing the exposed resin film; and a heat treatment step of heat-treating the developed resin film.

[0136] First, the resin composition of the present invention is applied to a substrate to obtain a coating film of the resin composition. As a substrate, a silicon wafer, a ceramic, a gallium arsenide, an organic circuit substrate, an inorganic circuit substrate, and a substrate having a circuit-forming material disposed on these substrates, etc. are used, but are not limited to these. As a coating method, there are methods such as spin coating, slit coating, dip coating, spray coating, and printing. In addition, the coating film thickness varies according to the coating method, the solid content concentration of the composition, the viscosity, etc., and is usually applied in a manner such that the film thickness after drying becomes 0.1 to 150 μm.

[0137] The substrate to be coated with the resin composition can be pre-treated with the aforementioned adhesion improver before coating. For example, the following method can be cited: using a solution obtained by dissolving the adhesion improver in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diethyl adipate at 0.5 to 20 mass %, the substrate surface is treated by spin coating, slit die coating, rod coating, dip coating, spray coating, steam treatment and the like. After the substrate surface is treated, a reduced pressure drying treatment can be implemented as needed. In addition, the reaction between the substrate and the adhesion improver can be carried out by heat treatment at 50°C to 280°C.

[0138] Next, the coating film of the resin composition is dried to obtain a resin film. Drying is preferably performed using an oven, a heating plate, infrared rays, etc., in the range of 50°C to 140°C for 1 minute to several hours. On the other hand, in the case of using a resin sheet formed from the resin composition of the present invention, when the aforementioned resin sheet has a protective film, it is peeled off, the resin sheet is placed opposite to the substrate, and bonded by thermocompression (sometimes the operation of placing the resin sheet opposite to the substrate and bonding by thermocompression is recorded as laminating the resin sheet on the substrate). Next, the resin sheet laminated on the substrate is dried in the same manner as when the above-mentioned resin film is obtained to form a resin film. The resin sheet can be obtained by applying the resin composition of the present invention on a supporting film composed of polyethylene terephthalate or the like as a releasable substrate and drying it.

[0139] Thermocompression bonding can be performed by heat pressing, heat lamination, heat vacuum lamination, etc. From the perspective of adhesion and embedding properties with the substrate, the lamination temperature is preferably 40° C. or higher. In addition, when the resin sheet is photosensitive, the lamination temperature is preferably 140° C. or lower in order to prevent the resin sheet from being cured during lamination and thus reducing the resolution of pattern formation in the exposure and development process.

[0140] When the resin film is photosensitivity, in the exposure process, chemical rays are irradiated through a mask having a desired pattern on the photosensitive resin film. When the resin film is not photosensitivity, in the exposure process, for example, after a known photoresist film is formed on the resin film, chemical rays are irradiated through a mask having a desired pattern. It should be noted that the photoresist film is preferably removed using a chemical solution or the like after the development process described below is completed. As chemical rays used in exposure, there are ultraviolet rays, visible light, electron beams, X-rays, etc. In the present invention, it is preferred to use g-line (436nm), h-line (405nm) or i-line (365nm) as common exposure wavelengths.

[0141] Next, the exposed resin film is developed. As a developer, preferably, tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, hexamethylenediamine and other alkaline compounds are aqueous solutions. In addition, according to the circumstances, polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, γ-butyrolactone, dimethylacrylamide, alcohols such as methanol, ethanol, isopropanol, esters such as ethyl lactate, propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, methyl isobutyl ketone, etc., or two or more thereof can be added to these alkaline aqueous solutions. After development, rinse with water. Here, the rinsing treatment may be performed by adding alcohols such as ethanol and isopropyl alcohol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and the like to water.

[0142] The resin film obtained in the above manner is heated to allow a thermal crosslinking reaction to proceed, thereby obtaining a cured film of the present invention. As far as the cured film is concerned, heat resistance and chemical resistance are improved by crosslinking. The heat treatment can be carried out by raising the temperature in stages, or it can be carried out while continuously raising the temperature. The heat treatment is preferably carried out for 5 minutes to 5 hours. As an example, an example of heat treatment at 140°C for 30 minutes and further heat treatment at 320°C for 60 minutes can be cited. As a heating treatment condition, it is preferably above 40°C and below 400°C. In order to allow the thermal crosslinking reaction to proceed, the heating treatment condition is preferably above 140°C, and more preferably above 160°C. In addition, in order to provide an excellent cured film and improve the yield, the heating treatment condition is preferably below 400°C, and more preferably below 350°C.

[0143] <Semiconductor Device>

[0144] The semiconductor device or electronic component of the present invention has a cured film formed by curing a resin composition or a resin sheet. The semiconductor device of the present invention is a semiconductor device having metal wiring and an insulating film, and may have the cured film of the present invention as an insulating film. A semiconductor device generally refers to a device comprising semiconductor elements and an integrated circuit obtained by integrating the semiconductor elements as a component. The semiconductor device of the present invention is not only a device comprising semiconductor elements, but also a device comprising components for semiconductor devices such as wiring substrates. In addition, semiconductor packages in which semiconductor elements, etc. are protected by sealing resins and further have the function of being electrically connected to the outside are also included in the semiconductor device of the present invention. Specifically, the cured film of the present invention can be preferably used for passivation films of semiconductors, protective films of semiconductor elements, interlayer insulating films of multilayer wiring for high-density packaging, and the like.

[0145] The cured film formed from the resin composition or resin sheet of the present invention is also suitable as a surface protective film for logic devices such as CPUs and GPUs, MRAMs, polymer memories (Polymer Ferroelectric RAM: PFRAM) that are expected to be the next generation of memories, phase change memories (Phase Change RAM: PCRAM, or Ovonic Unified Memory: OUM) and other memories. In addition, it can also be used for an insulating layer of a display device including a first electrode formed on a substrate and a second electrode disposed opposite to the first electrode, specifically, for example, LCDs, ECDs, ELDs, and display devices (organic electroluminescent devices) using organic electroluminescent elements.

[0146] In particular, for semiconductor devices in recent years, along with the further miniaturization of the electrodes of semiconductor elements and the metal wiring of the substrate, semiconductor devices with electrodes, metal wiring and bumps using gold, silver, copper, nickel, aluminum, etc. have become mainstream, and in the etching process of the metal wiring, barrier metal, and the pattern forming process of the resist when forming them, they are in contact with many chemical liquids such as flux and stripping agents for removing photoresists. When using the cured film formed from the resin composition or resin sheet of the present invention as a protective film for such electrodes and metal wiring, it has high tolerance to these chemical liquids, so it can be particularly preferably used. It should be noted that copper wiring is sometimes subjected to oxidation treatment in the manufacturing process. In such a case, the cured film of the present invention can also be preferably used. In addition, the resin composition or resin sheet of the present invention has thick film processability, so it is not only the case where the thickness of the metal wiring is less than 10 μm, but also can be used as a protective film or interlayer insulating film even in the range of more than 10 μm and less than 20 μm. In this case, the thickness of the cured film of the present invention is preferably 11 μm or more, more preferably 15 μm or more, from the viewpoint of coverage of metal wiring, and preferably 20 μm or less, more preferably 1 μm or less, from the viewpoint of processability.

[0147] Next, an example in which a cured film formed from the resin composition or resin sheet of the present invention is applied to a semiconductor device having bumps will be described using the drawings. Figure 1 FIG. 1 is an enlarged cross-sectional view of a pad portion of a semiconductor device having a bump. Figure 1As shown, an aluminum (hereinafter referred to as Al) pad 2 for input and output and a passivation film 3 are formed on a silicon wafer 1, and a through hole is formed in the passivation film 3. Furthermore, an insulating film 4 formed from a cured product of the resin composition or resin sheet of the present invention is formed thereon, and further, a metal film 5 is formed in a manner electrically connected to the Al pad 2. As a material for the metal film 5, Cr, Ti, etc. can be preferably used. A metal wiring 6 is provided on the metal film 5. As a material for the metal wiring 6, Ag, Cu, etc. can be preferably used. In recent years, as described above, copper wiring is particularly preferably used. Preferably, the metal wiring 6 is formed on the metal film 5 by a plating method. On the insulating film 4 and the metal film 5, an insulating film 7 obtained from a cured product of the resin composition or resin sheet of the present invention is formed. In the insulating film 7, it is necessary to preliminarily open the scribe groove 9 and the pad portion where the solder bump 10 is provided by a photolithography process. A barrier metal 8 is film-formed on the pad portion, and then the solder bump 10 is formed. Polyimide resin and polybenzoxazole resin also have excellent mechanical properties, and thus can relax stress from the sealing resin during packaging, thereby preventing damage to the low-k dielectric constant (low-k) layer and providing a highly reliable semiconductor device.

[0148] Next, based on Figure 2 A detailed method for manufacturing a semiconductor device is described. Figure 2 In step a, the resin composition or resin sheet of the present invention is applied or laminated on the silicon wafer 1 having the Al pad 2 and the passivation film 3 formed thereon, patterned by a photolithography process, and then cured to form an insulating film 4. Figure 2 In step b, the metal film 5 is formed by sputtering. Figure 2 As shown in c, metal wiring 6 is formed on the metal film 5 by plating. Figure 2 d', the resin composition or resin sheet of the present invention is coated or laminated thereon, patterned by photolithography, and then cured to form a structure as shown in FIG. Figure 2 d. Insulating film 7 is formed in a shape as shown in FIG. 4. At this time, the insulating film 7 forms an opening at the scribe groove 9. Metal wiring (so-called rewiring) can be further formed on the insulating film 7. By repeating the above-mentioned steps, a multilayer wiring structure can be formed in which more than two layers of rewiring are separated by an insulating film obtained from the cured product of the resin composition or resin sheet of the present invention. The insulating film separating the rewiring is called an interlayer insulating film. At this time, although the insulating film formed will be in contact with various chemical solutions many times, due to the excellent adhesion and chemical resistance of the insulating film obtained from the cured product of the resin composition or resin sheet of the present invention, a good multilayer wiring structure can be formed. There is no upper limit to the number of layers of the multilayer wiring structure, and most of the layers used are less than 10 layers.

[0149] Then, if Figure 2 e and Figure 2 As shown in FIG. 5 , a barrier metal 8 and a solder bump 10 are formed. Then, the wafer is cut along the scribe line 9 to be divided into chips. When the insulating film 7 does not form an opening at the scribe line 9 or a residue remains, cracks may occur during cutting, which may affect the reliability of the chip. Therefore, a technology that can provide excellent pattern processing in thick film processing is very ideal for obtaining high reliability of semiconductor devices.

[0150] In addition, the resin composition or resin sheet of the present invention can also be suitably used in fan-out wafer-level packaging (fan-out WLP) or fan-out panel-level packaging (fan-out PLP). Fan-out WLP is a technology for manufacturing multiple semiconductor packages on a wafer at once. Fan-out PLP is a technology for manufacturing multiple semiconductor packages on a square substrate, i.e., a panel, at once in part or all of the process.

[0151] Figure 3 It is a cross-sectional view of the manufacturing process of an example of a semiconductor device having a cured film of the present invention. In detail, it is an enlarged cross-sectional view of a semiconductor package called a chip-first fan-out WLP or a chip-first fan-out PLP. A silicon wafer having an Al pad 2 and a passivation film 3 is cut and divided into semiconductor chips 1', and then sealed with a sealing resin 11. On the sealing resin 11 and the semiconductor chip 1', the resin composition or resin sheet of the present invention is applied or laminated, and an opening is set by pattern formation using a photolithography process, and then cured to form an insulating film 4. On the insulating film 4, a metal film 5 formed of Cr, Ti, etc. and a metal wiring 6 formed of Ag, Cu, etc. are further formed. The metal film 5 and the metal wiring 6 are electrically connected to the Al pad 2 provided on the semiconductor chip 1' at the opening provided in the insulating film 4. An insulating film 7 is further formed thereon. In the formation of the insulating film 7, it is also preferred to use the resin composition or resin sheet of the present invention. The barrier metal 8 and the solder bump 10 are formed in the opening portion provided in the insulating film 7. The barrier metal 8 and the solder bump 10 are electrically connected to the metal wiring 6.

[0152] Chip-first fan-out WLP or Chip-first fan-out PLP is a semiconductor package that is provided with an extension portion around the semiconductor chip using a sealing resin such as epoxy resin, rewiring is performed from the electrode on the semiconductor chip to the extension portion, and solder balls are also mounted on the extension portion, thereby ensuring the necessary number of terminals. In chip-first fan-out WLP or chip-first fan-out PLP, metal wiring is provided in a manner that crosses the boundary line formed by the main surface of the semiconductor chip and the main surface of the sealing resin. That is, an insulating film 7 is provided as an interlayer insulating film on a substrate composed of two or more materials such as a semiconductor chip and a sealing resin, and metal wiring (rewiring) 6 is provided on the interlayer insulating film.

[0153] In chip-first fan-out WLP or chip-first fan-out PLP, the rewiring is becoming increasingly miniaturized. The cured film of the present invention has high metal adhesion to metal wirings with a width of 5 μm or less and a spacing between adjacent metal wirings, and can therefore be suitably used for fine rewiring. Here, the width of the metal wiring and the spacing between adjacent metal wirings are 5 μm or less, which means that the width of the metal wiring is 5 μm or less and the spacing between adjacent metal wirings is also 5 μm or less.

[0154] In a chip-first fan-out WLP or chip-first fan-out PLP having such a fine structure, it is preferred to have a multilayer stacked structure in which a plurality of rewiring layers are stacked, and in each adjacent rewiring layer, the width of the metal wiring of the rewiring layer closer to the semiconductor chip and the interval between adjacent metal wirings are the same or narrower than the width of the metal wiring of the rewiring layer farther from the semiconductor chip and the interval between adjacent metal wirings. Here, the so-called rewiring layer refers to a layer including a group of rewiring and an interlayer insulating film formed thereon in a multilayer wiring structure in which a plurality of rewirings are separated by a plurality of interlayer insulating films. It should be noted that there is also a case where the rewiring layer includes only one layer. In addition, the so-called width of the metal wiring of the rewiring layer and the spacing between adjacent metal wirings being the same or narrower means that: compared with the width of the metal wiring of the rewiring layer farther away from the semiconductor chip, the width of the metal wiring of the rewiring layer closer to the semiconductor chip is the same or narrower, and compared with the spacing between adjacent metal wirings in the rewiring layer farther away from the semiconductor chip, the spacing between adjacent metal wirings in the rewiring layer closer to the semiconductor chip is the same or narrower.

[0155] In this structure, preferably, among adjacent rewiring layers, the thickness of the interlayer insulating film of the rewiring layer closer to the semiconductor chip is equal to or thinner than the thickness of the interlayer insulating film of the rewiring layer farther from the semiconductor chip.

[0156] That is, the rewiring layers constituting the multilayer wiring structure are preferably gradually fine-pitch from far away from the semiconductor chip to close to the semiconductor chip. With such a structure, even a highly integrated semiconductor chip can smoothly connect the semiconductor chip and the terminal. In order to manufacture such a structure, the in-plane uniformity of the interlayer insulating film in each rewiring layer is important.

[0157] In addition, in fan-out WLP or fan-out PLP, there is a type of semiconductor package made using the following process called RDL (Redistribution Layer)-first, that is, on a supporting substrate provided with a temporary adhesive material, a plurality of redistribution layers including metal wiring (redistribution) and an interlayer insulating film are stacked, and a semiconductor chip and a sealing resin are further arranged thereon to form a semiconductor package, and then the supporting substrate and the redistribution layer are peeled off to separate the semiconductor package. That is, the supporting substrate is only used in the manufacturing process and is not included in the completed semiconductor package. In this process, as a supporting substrate, a glass substrate that is more easily warped than a silicon wafer is mostly used, so the insulating film is preferably low stress. In addition, in this process, since a large-area panel is used (which has cost advantages brought about by mass production), it becomes a subject to reduce the warping caused by film shrinkage of the interlayer insulating film and improve the in-plane uniformity of the film thickness.

[0158] use Figure 4 The method for manufacturing a semiconductor device in RDL-first is described below. Figure 4 In a, a barrier metal such as Ti is formed on a supporting substrate 20 such as a glass substrate or a silicon wafer on which a temporary bonding material may be arranged by sputtering, and then a Cu seed crystal (seed layer) is formed thereon by sputtering, and then an electrode pad 21 obtained from Cu is formed by plating. Figure 4 In step b, the resin composition or resin sheet of the present invention is applied or laminated on the entire surface of the support substrate 20 on which the electrode pads 21 are formed, patterned by a photolithography process, and then cured to form an insulating film 22. Figure 4 In step c, a seed layer is formed again by sputtering, and a metal wiring 23 (rewiring) is formed from Cu by plating. Figure 4 b and Figure 4 c process, forming Figure 4 d shows a multilayer wiring structure. Figure 4In the process of e, the resin composition or resin sheet of the present invention is coated or laminated again, a pattern is formed by a photolithography process, and then it is cured to form an insulating film 22, and then a Cu column 24 is formed on the metal wiring 23 in the opening of the insulating film 22 by a plating method. Here, the pitch of the Cu column 24 is equal to the pitch of the conductive part of the semiconductor chip 26. That is, the pitch of the conductive part of the semiconductor chip 26 is finer than the pitch of the electrode pad 21, and the result is as follows Figure 4 As shown in FIG. 5 , each rewiring layer constituting the multilayer wiring structure gradually fine-pitch from the electrode pad 21 to the Cu column 24, while the wiring is multilayered. The thickness of the adjacent interlayer insulating film 22 in the multilayer wiring structure is also the same or becomes thinner as it approaches the semiconductor chip. Figure 4 In the process of f, the semiconductor chip 26 is connected to the Cu column 24 via the solder bump 25. Thus, the electrode pad 21 and the semiconductor chip 26 are electrically connected via the metal wiring 23 and the solder bump 25. Then, the semiconductor chip 26 is sealed with a sealing resin to form a semiconductor package, and then the support substrate and the rewiring layer are peeled off to separate the semiconductor package. In the above manner, a semiconductor device with a multi-layer wiring structure using the RDL-first process can be obtained.

[0159] In addition, for the semiconductor package of the type that semiconductor chip is embedded in the recess formed on the glass epoxy resin substrate, metal wiring is set in the mode of the boundary line of the main surface of the main surface of the semiconductor chip and the printed circuit board.In this way, also on the base material consisting of two or more materials, interlayer insulating film is formed, metal wiring (rewiring) is formed on this interlayer insulating film.For the cured film formed by the resin combination of the present invention or resin sheet solidification, there is high adhesion with the semiconductor chip formed with metal wiring, and also there is high adhesion with sealing resins such as epoxy resins, therefore be suitable as the interlayer insulating film on the base material consisting of two or more materials.

[0160] <Other devices>

[0161] Furthermore, the resin composition or resin sheet of the present invention is also suitably used for a coil component of an inductor device. Figure 5 FIG. 2 is a cross-sectional view showing a coil component of an inductor device according to an embodiment of the present invention. Figure 5As shown, an insulating film 13 is formed on the entire surface of a substrate 12, and an insulating film 14 is formed thereon, and the insulating film 14 is formed with an opening. As the substrate 12, ferrite or the like is used. The resin composition or resin sheet of the present invention can be used for any of the insulating film 13 and the insulating film 14. A metal film 15 composed of Cr, Ti, etc. is formed in the opening of the insulating film 14, and a metal wiring 16 composed of Ag, Cu, etc. is formed thereon by a plating method. The metal wiring 16 is formed in a spiral shape. The above steps are repeated multiple times to stack the insulating film 13, the insulating film 14, the metal film 15 and the metal wiring 16, thereby being able to function as a coil. The metal wiring 16 arranged on the top layer is connected to the electrode 18 through the metal wiring 17 formed of Ag, Cu, etc., and is sealed with a sealing resin 19.

[0162] The resin composition or resin sheet of the present invention can be used for a display device including: a first electrode formed on a substrate; an insulating layer formed so as to cover the periphery of the first electrode; and a second electrode provided to face the first electrode.

[0163] The resin composition or resin sheet of the present invention is also suitable for an organic EL display device. The organic EL display device has a driving circuit, a planarization layer, a first electrode, an insulating layer, a light-emitting layer and a second electrode on a substrate, wherein the planarization layer and / or the insulating layer are formed from the cured film of the present invention. Organic EL light-emitting materials are easily degraded by moisture, sometimes resulting in adverse effects such as a reduction in the area ratio of the light-emitting portion relative to the area of ​​the light-emitting pixel, but since the water absorption rate of the cured film of the present invention is low, stable driving and light-emitting characteristics can be obtained. When an active matrix organic EL display device is taken as an example, on a substrate formed of glass, various plastics, etc., there is a TFT and a metal wiring located on the side of the TFT and connected to the TFT, on which a planarization layer is provided in a manner covering the concave and convex, and further a display element is provided on the planarization layer. The display element is connected to the metal wiring via a contact hole formed in the planarization layer.

[0164] use Figure 6 A specific example of a display device will be described. The display device includes: a first electrode formed on a substrate; an insulating layer formed so as to cover a periphery of the first electrode; and a second electrode provided to face the first electrode.

[0165] Figure 6, a cross-sectional view of an example of a TFT substrate is shown in FIG. On a substrate 32, bottom-gate or top-gate TFTs (thin film transistors) 27 are arranged in rows and columns, and a TFT insulating layer 29 is formed in a state of covering the TFTs 27. In addition, a metal wiring 28 connected to the TFTs 27 is provided on the TFT insulating layer 29. Furthermore, a planarizing layer 30 is provided on the TFT insulating layer 29 in a state of burying the metal wiring 28. A contact hole 33 that reaches the wiring 28 is provided in the planarizing layer 30. Then, a transparent electrode 31 formed of ITO or the like as a first electrode is formed on the planarizing layer 30 through the contact hole 33 in a state of being connected to the metal wiring 28. Here, the transparent electrode 31 becomes an electrode of a display element (for example, an organic EL element). Then, an insulating layer 34 is formed in a manner covering the periphery of the transparent electrode 31. Then, a light-emitting layer is formed on the first electrode and the insulating layer, and a second electrode is provided in a manner opposite to the first electrode. The organic EL element may be a top emission type that releases the emitted light from the side opposite to the substrate 32, or a bottom emission type that extracts the light from the side of the substrate 32. In this way, an active matrix type organic EL display device can be obtained in which each organic EL element is connected to a TFT 27 for driving it.

[0166] The TFT insulating layer 29, the planarizing layer 30 and / or the insulating layer 34 can be formed by the following steps: forming a resin film formed from the resin composition or resin sheet of the present invention; exposing the resin film; developing the exposed resin film; and heating the developed resin film. An organic EL display device can be obtained by a manufacturing method having these steps.

[0167] Example

[0168] Hereinafter, the present invention will be described with reference to Examples and the like, but the present invention is not limited to these Examples.

[0169] The evaluation methods in each of the Examples and Comparative Examples are shown below.

[0170] (1) Weight average molecular weight of resin (A)

[0171] The resin solution obtained in each synthesis example was measured for a polystyrene-equivalent weight average molecular weight (Mw) using a GPC (gel permeation chromatography) apparatus Waters 2690-996 (manufactured by Japan Waters Co., Ltd.) and N-methyl-2-pyrrolidone (hereinafter referred to as NMP) as a developing solvent.

[0172] (2) Evaluation of the contents of the compound (B), additive (C), and morpholine in the resin composition

[0173] The resin (A) was fractionated from the resin composition used in each of the Examples and Comparative Examples using a GPC fractionator (manufactured by Shimadzu Corporation) to determine the content of the resin (A) in the resin composition.

[0174] Next, after concentrating the components other than the solid component obtained by GPC fractionation using an evaporator, GC-MS analysis was performed using a GC-MS apparatus (manufactured by Shimadzu Corporation) under the conditions of column temperature: 40 to 250° C., carrier gas: helium (2.1 mL / min), and scanning range: m / z 29 to 800. GC-MS analysis was performed using 3,5-dimethyl-4-acetyl-4-pyrrolin-2-one (B1-1), 1-methyl-4-pyrrolin-2-one (B1-2), 1-methyl-3-pyrrolin-2-one (B2-3), 3-ethyl-4-methyl-3-pyrrolin-2-one (B2-4), 1,5-dimethylpyrrolidone (C-1), 1,4-dimethylpyrrolidone (C-2), 1,3-dimethylpyrrolidone (C-3), and morpholine under the same conditions as above, and a calibration curve was prepared to measure each content. Based on the obtained contents, the contents of the compound (B), additive (C) and morpholine in the resin composition are calculated. In addition, similarly, the content of the compound (B) represented by formula (2) (hereinafter, referred to as compound B2) relative to the compound (B) represented by formula (1) (hereinafter, referred to as compound B1) and the content of morpholine relative to the compound (B) are also calculated.

[0175] (3) Storage stability evaluation

[0176] For the resin composition used in each embodiment and comparative example, an E-type viscometer TVE-25H (manufactured by Toki Industry Co., Ltd.) was used to measure the temperature at 25°C and the rotation speed at 1.0 rpm, and the value after 10 minutes was recorded. Then, after being stored at -15°C for a specified time, it was thawed to a temperature of 25°C for 2 hours, and the viscosity was measured in the same manner as above. The viscosity after storage was calculated by setting the viscosity before storage to 1.00. It should be noted that the closer the calculated value is to 1.00, the better the storage stability is, and the evaluation criteria are shown below.

[0177] Viscosity change rate 0.95 or more and 1.05 or less: Excellent (no need to adjust film thickness during coating)

[0178] Viscosity change rate 0.85 or more and less than 0.95, greater than 1.05 and less than 1.15: Good (film thickness can be adjusted by slightly changing the conditions during coating)

[0179] Viscosity change rate 0.80 or more and less than 0.85, greater than 1.15 and less than 1.20: Fair (film thickness can be adjusted by changing the conditions during coating)

[0180] Viscosity change rate is less than 0.80 and greater than 1.20: Not acceptable (difficult to adjust film thickness during coating)

[0181] (4) Heat resistance evaluation

[0182] The resin composition used in each embodiment and comparative example was applied on a 4-inch silicon wafer substrate using a spin coater coating device (manufactured by MIKASA Co., Ltd.), and baked at 120°C for 3 minutes to prepare a pre-baked film with a thickness of 15 μm. It should be noted that the film thickness was measured using Lambda Ace STM-602 (manufactured by SCREEN Co., Ltd.) under a refractive index of 1.63. For the obtained pre-baked film, an inert oven CLH-21CD-S (manufactured by Koyo Thermo System Co., Ltd.) was used to heat the film to 350°C at a temperature increase of 5°C / min at an oxygen concentration of less than 20 ppm, and further calcined at 350°C for 1 hour to prepare a cured film of the resin composition. After measuring the film thickness of the obtained cured film, an incision was made in the peripheral portion of the silicon wafer substrate with the cured film, and the film was immersed in an aqueous hydrofluoric acid solution. Then, the cured film of the resin composition was peeled off from the silicon wafer substrate to separate the cured film.

[0183] For the obtained cured film (sample), the weight loss starting temperature is measured under nitrogen flow using a thermogravimetric measuring device TGA-50 (manufactured by Shimadzu Corporation). The heating conditions are as follows: in the first stage, the sample is heated to 150°C at a heating rate of 10°C / min and maintained at 150°C for 30 minutes. Thus, the adsorbed water of the sample is removed. In the subsequent second stage, the sample is air-cooled to room temperature at a cooling rate of 10°C / min. In the subsequent third stage, the sample is heated at a heating rate of 10°C / min, and the temperature at which a 1% weight loss is confirmed is determined as the weight loss starting temperature. The higher the temperature, the better the heat resistance.

[0184] (Compound)

[0185] The compounds and abbreviations used appropriately are shown below.

[0186] AIBN: Azobisisobutyronitrile

[0187] 4,4'-DAE: 4,4'-diaminodiphenyl ether

[0188] BTDA: Benzophenone tetracarboxylic dianhydride

[0189] Compound B1-1: 3,5-dimethyl-4-acetyl-4-pyrrolidine-2-one (corresponding to the compound represented by formula (1), not corresponding to the compound represented by formula (3))

[0190] Compound B1-2: 1-methyl-4-pyrrolidine-2-one (equivalent to the compound represented by formula (3))

[0191] Compound B2-3: 1-methyl-3-pyrrolidine-2-one (equivalent to the compound represented by formula (4))

[0192] Compound B2-4: 3-ethyl-4-methyl-3-pyrrolin-2-one (corresponding to the compound represented by formula (2), not corresponding to the compound represented by formula (4))

[0193] Additive C-1: 1,5-dimethylpyrrolidone

[0194] Additive C-2: 1,4-dimethylpyrrolidone

[0195] Additive C-3: 1,3-dimethylpyrrolidone.

[0196] <Synthesis Example 1 Synthesis of Resin A-1>

[0197] 2 g of AIBN and 50 g of NMP were placed in a 500 mL flask. Then, 40.2 g of methacrylic acid, 21.3 g of styrene, and 24.7 g of methyl methacrylate were added, stirred at room temperature for a while, the flask was fully purged with nitrogen by bubbling, and then heated and stirred at 70°C for 5 hours. Next, 14.6 g of glycidyl methacrylate, 0.2 g of p-methoxyphenol, and 100 g of NMP were added to the obtained solution, and heated and stirred at 90°C for 4 hours. NMP was added to the obtained acrylic polymer solution in such a way that the solid content concentration became 20 wt%, and resin (A-1) was obtained. The weight average molecular weight Mw measured by the GPC method in terms of polystyrene conversion was 13,500.

[0198] <Synthesis Example 2 Synthesis of Resin A-2>

[0199] In a 500 mL flask, 22.8 g of 4,4'-DAE and 36.0 g of BTDA were dissolved in 186.2 g of NMP under a dry nitrogen stream, and stirred at 70°C for 5 hours. Then, 0.7 g of phthalic anhydride was added together with 10 g of NMP, and reacted at 40°C for 1 hour. Then, NMP was added to the obtained solution in such a way that the solid content concentration became 20 wt%, and resin A-2 was obtained. The weight average molecular weight Mw measured by the GPC method in terms of polystyrene was 70,000.

[0200] <Production Example 1>

[0201] 99.90 parts by weight of the resin (A-2) obtained in Synthesis Example 2 and 0.10 parts by weight of the compound (B1-1) were mixed and stirred to obtain a resin composition (J-1). The resin composition (J-1) was subjected to the aforementioned GPC fractionation and GC-MS analysis and evaluation. As a result, the content of the compound (B1-1) in the resin composition was 0.10 parts by weight.

[0202] <Manufacturing Example 2 to Manufacturing Example 35>

[0203] The resin (A-1) and resin (A-2) obtained in Synthesis Examples 1 and 2 were mixed with compounds (B1-1) to (B2-4), additives (C-1) to (C-3), and morpholine to prepare resin compositions (J-2) to (J-35). As described above, GPC fractionation and GC-MS analysis and evaluation were performed, and the calculated contents are shown in Tables 1 to 4.

[0204] [Table 1]

[0205]

[0206] [Table 2]

[0207]

[0208] [Table 3]

[0209]

[0210] [Table 4]

[0211] [Table 4]

[0212]

[0213] <Example 1>

[0214] Using the resin composition (J-1) obtained in Production Example 1, storage stability evaluation and heat resistance evaluation were performed by the above-mentioned methods.

[0215] In the storage stability evaluation, the initial viscosity was 15,000 mPa·s, but the viscosity did not change after 1 month and 3 months, and it was 15,750 mPa·s after 6 months, indicating excellent storage stability. After 9 months, it was 16,500 mPa·s, indicating good storage stability, and after 12 months, it was 18,000 mPa·s, indicating fair storage stability.

[0216] As a result of the heat resistance evaluation, 1% weight loss was found to be 450°C.

[0217] <Examples 2 to 34, Comparative Example 1>

[0218] Using the resin compositions (J-2) to (J-35) obtained in Production Examples 2 to 35, evaluation was performed in the same manner as in Example 1. The evaluation results of Examples 2 to 34 and Comparative Example 1 are shown in Tables 5 to 10.

[0219] [Table 5]

[0220]

[0221] [Table 6]

[0222]

[0223] [Table 7]

[0224] [Table 7]

[0225]

[0226] [Table 8]

[0227]

[0228] [Table 9]

[0229]

[0230] [Table 10]

[0231]

[0232] Description of Reference Numerals

[0233] 1: Silicon wafer

[0234] 1': Semiconductor chip

[0235] 2: Al pad

[0236] 3: Passivation film

[0237] 4: Insulation film

[0238] 5: Metal film

[0239] 6: Metal wiring

[0240] 7: Insulation film

[0241] 8: Barrier Metal

[0242] 9: Scribe groove

[0243] 10: Solder Bumps

[0244] 11: Sealing resin

[0245] 12: Substrate

[0246] 13: Insulation film

[0247] 14: Insulation film

[0248] 15: Metal film

[0249] 16: Metal wiring

[0250] 17: Metal wiring

[0251] 18: Electrode

[0252] 19: Sealing resin

[0253] 20: Support base plate

[0254] 21: Electrode pad

[0255] 22: Insulation film

[0256] 23: Metal wiring

[0257] 24: Cu column

[0258] 25: Solder Bump

[0259] 26: Semiconductor chips

[0260] 27: TFT

[0261] 28: Wiring

[0262] 29: TFT insulation layer

[0263] 30: Flattening layer

[0264] 31: Transparent electrode

[0265] 32: Substrate

[0266] 33: Contact hole

[0267] 34: Insulation layer

[0268] Industrial Applicability

[0269] The resin composition of the present invention can be suitably used for the surface protection layer of semiconductor elements such as LSI, interlayer insulating layer, insulating layer of organic electroluminescence and organic EL display element, planarization layer of TFT substrate for display device. In addition, it can also be suitably used for fan-out wafer level packaging (fan-out WLP) or fan-out panel level packaging (fan-out PLP). The cured film of the present invention can be suitably used for the passivation film of semiconductor, the protective film of semiconductor element, the interlayer insulating film of multilayer wiring for high-density packaging, etc.

Claims

1. A resin composition comprising at least a resin (A) and a compound (B), wherein the compound (B) is a compound represented by formula (1) and / or a compound represented by formula (2), In formula (1) and formula (2), R 1 ~R 8 Each independently represents a group selected from the group consisting of a hydrogen atom, an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group and an organic group having 1 to 20 carbon atoms.

2. The resin composition according to claim 1, wherein The resin (A) contains at least one selected from the group consisting of polyimide, polybenzoxazole, polyamideimide, and precursors thereof.

3. The resin composition according to claim 1, wherein The compound represented by the formula (1) and the compound represented by the formula (2) are respectively the compound represented by the formula (3) and the compound represented by the formula (4), 4. The resin composition according to claim 1, wherein The content of the compound (B) is 0.01 to 0.25% by weight relative to 100% by weight of the resin composition.

5. The resin composition according to claim 1, wherein The compound (B) is a compound represented by formula (1) and a compound represented by formula (2).

6. The resin composition according to claim 5, wherein The content ratio of the compound represented by the formula (1) to the compound represented by the formula (2) is 100 to 2,000 parts by weight of the compound represented by the formula (2) per 100 parts by weight of the compound represented by the formula (1). 7 . The resin composition according to claim 1 , further comprising at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone.

8. The resin composition according to claim 7, wherein The content of the additive (C) is 0.01 to 0.25 wt % based on 100 wt % of the resin composition.

9. The resin composition according to claim 1, comprising morpholine.

10. The resin composition according to claim 9, wherein The content of morpholine is 0.01 to 0.05% by weight based on 100% by weight of the resin composition.

11. The resin composition according to claim 9, wherein The content ratio of the compound (B) and morpholine is 5 to 20 parts by weight of morpholine relative to 100 parts by weight of the compound (B). 12 . A cured film, which is a cured film of the resin composition according to claim 1 . 13 . A semiconductor device comprising the cured film according to claim 12 .

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