Polyhydroxyamide compound, photosensitive resin composition, dry film, cured product, and electronic component

Abstract

To provide: a novel polyhydroxyamide compound that can be used in a resin composition such as a photosensitive resin composition; a photosensitive resin composition that contains the polyhydroxyamide compound; a dry film that has a resin layer formed using the photosensitive resin composition; a cured product that is formed of the photosensitive resin composition or the resin layer of the dry film; and an electronic component that has the cured product.SOLUTION: A polyhydroxyamide compound having a structural unit represented by the following formula (1) is provided. (In the formula, R1 and R2 each independently represent a divalent organic group, and a ring A and a ring B represent divalent groups having a monocyclic or polycyclic aromatic. At least one among R1, the ring A, and the ring B contains one or more phenolic hydroxyl groups).SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to a polyhydroxyamide compound, a photosensitive resin composition, a dry film, a cured product, and an electronic component.

Background Art

[0002] A photosensitive resin composition containing a polyimide precursor exhibits excellent properties such as insulation, heat resistance, and mechanical strength, and thus is widely used as an insulating film in various fields such as semiconductors and electronic components.

[0003] Conventionally, with the improvement in performance and miniaturization of electronic components and electrical equipment, higher integration of semiconductor elements has been demanded. To meet this requirement, high-performance and miniaturization technologies have been developed in the field of semiconductor element packages such as wafer-level packages. In the insulating film used for the redistribution layer, excellent resolution is required for miniaturization of pattern formation.

[0004] Patent Document 1 discloses a photosensitive resin composition containing a polybenzoxazole precursor, a compound that generates an acid upon irradiation with actinic rays in a specific wavelength region, a compound that can be crosslinked or polymerized, and a compound that generates an acid by heat. According to the disclosure of Patent Document 1, a negative-type photosensitive resin composition is provided that exhibits good sensitivity and resolution and imparts chemical resistance, heat resistance, and mechanical properties.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] In recent years, with the demands for higher performance and miniaturization of electronic components and electrical devices, further high integration of semiconductor elements has been required. To meet these demands, high-performance and miniaturization technologies in the field of semiconductor element packages such as wafer-level packages (WLPs) have been developed, and in the insulating films used for rewiring layers, in addition to further miniaturization of pattern formation, various characteristics suitable for these high-performance and miniaturization technologies have come to be required.

[0007] Therefore, an object of the present disclosure is to provide a novel polyhydroxyamide compound that can be used in resin compositions such as photosensitive resin compositions.

Means for Solving the Problems

[0008] One aspect of the present invention is a polyhydroxyamide compound. The polyhydroxyamide compound is a polyhydroxyamide compound having a structural unit of the following formula (1).

Chemical formula

[0009] In the polyhydroxyamide compound of the above aspect, it is preferable that at least one of ring A or ring B in the formula (1) contains one or more phenolic hydroxyl groups.

[0010] In the polyhydroxyamide compound of the above aspect, it is preferable that the formula (1) contains a structural unit of the following formula (2).

Chemical formula

[0011] Another aspect of the present invention is a photosensitive resin composition. The photosensitive resin composition contains the polyhydroxyamide compound of the above aspect.

[0012] Another aspect of the present invention is a dry film. The dry film includes a resin layer formed by the photosensitive resin composition of the above aspect.

[0013] Another aspect of the present invention is a cured product. The cured product is obtained by curing the photosensitive resin composition of the above aspect or the resin layer of the dry film of the above aspect.

[0014] Another aspect of the present invention is an electronic component. The electronic component has the cured product of the above aspect.

Advantages of the Invention

[0015] According to the present invention, a novel polyhydroxyamide compound that can be used in resin compositions such as photosensitive resin compositions can be provided. Further, a photosensitive resin composition containing the polyhydroxyamide compound; a dry film having a resin layer formed by the photosensitive resin composition; a cured product formed by the photosensitive resin composition or the resin layer of the dry film; an electronic component having the cured product; can be provided.

Brief Description of the Drawings

[0016]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0017] Hereinafter, embodiments of the disclosed technology will be described in detail. In this specification, the notation "a~b" in the description of a numerical range represents a to b inclusive, unless otherwise specified.

[0018] In this specification, when a plurality of upper limit values and a plurality of lower limit values are separately described, all numerical ranges that can be freely combined and set from these upper limit values and lower limit values are considered to be described in this specification.

[0019] In this specification, when a certain compound is described, its isomers are also considered to be described simultaneously.

[0020] The "substituent" is not particularly limited, and unless otherwise specified, examples include a hydroxyl group, a phenol group, a phenyl group, a halogen group, a thiol group, a sulfo group, an amino group, an imino group, a hydroxyamino group, a nitro group, a nitroso group, a carboxy group, a thiocarboxy group, an ester group, a thioester group, an aldehyde group, an acetyl group, and the like.

[0021] "Aromatic" is not particularly limited, and unless otherwise specified, it includes heterocycles.

[0022] In this specification, the solid content means the components constituting the photosensitive resin composition or the composition other than the solvents (especially organic solvents) of each raw material, and is based on mass unless otherwise specified.

[0023] 1. Polyhydroxyamide compound The polyhydroxyamide compound of this embodiment has a structural unit represented by the following formula (1).

Chemical formula

[0024] R1 in formula (1) is not particularly limited as long as it is a divalent organic group. For example, it can include an aliphatic hydrocarbon group (alkylene group, cycloalkylene group), an aromatic hydrocarbon group (arylene group), an ether group, a ketone group, an ester group, a sulfonyl group, etc. Among these, R1 is preferably an aliphatic hydrocarbon group having 1 to 30 carbon atoms. R1 may further contain a substituent, for example, it may contain a phenol group.

[0025] R2 in formula (1) is not particularly limited as long as it is a divalent organic group. For example, it can include an aliphatic hydrocarbon group (alkylene group, cycloalkylene group), an aromatic hydrocarbon group, (arylene group), an ether group, a ketone group, an ester group, a sulfonyl group, a triazine ring, a triazole ring, a siloxane bond, etc. More specifically, it preferably has a structure such as biphenyl, diphenyl ether, diphenyl thioether, benzophenone, diphenylmethane, diphenylpropane, diphenylhexafluoropropane, diphenyl sulfoxide, diphenyl sulfone, benzene, 2-methyl-1,3,5-triazine, 2-phenyl-1,3,5-triazine, 1,1,3,3,-tetramethyl-1,3-dipropyldisiloxane, etc.

[0026] From the viewpoints of the resolution of the photosensitive resin composition and the insulation reliability of the cured product, the number of carbon atoms of R1 is preferably 1 to 30, 1 to 10, or 1 to 5. The number of carbon atoms of R2 is preferably 1 to 30, 5 to 20, or 5 to 15. In addition, two or more of the groups exemplified above as R1 and R2 can be respectively contained in the molecule of the polyhydroxyamide compound. Also, R1 and R2 may have the same structure or different structures.

[0027] In formula (1), ring A and ring B each independently represent a group having a monocyclic or polycyclic aromatic group. The monocyclic or polycyclic aromatic group is preferably, for example, a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, or an anthracene ring, and more preferably a benzene ring. Examples of the group having a benzene ring include a phenyl group, a biphenyl group, and a terphenyl group. The number of carbon atoms of ring A is preferably 6 to 20, and more preferably 6 to 15. Ring A and ring B may further contain a substituent, and preferably contain, for example, a phenolic hydroxyl group.

[0028] At least one of R1, ring A, and ring B contains one or more phenolic hydroxyl groups. Further, at least one of ring A and ring B preferably contains one or more phenolic hydroxyl groups, and more preferably both ring A and ring B each contain one or more phenolic hydroxyl groups.

[0029] In the polyhydroxyamide compound of the present embodiment, since at least one of R1, ring A, and ring B has a phenolic hydroxyl group which is an alkali-soluble group, it can be used as an alkali-soluble resin. As will be described later, when the polyhydroxyamide compound of the present embodiment is used as a photosensitive resin composition, an alkali-developable negative photosensitive resin composition or a positive photosensitive resin composition can be obtained.

[0030] In the polyhydroxyamide compound of the present embodiment, it is preferable that the formula (1) contains a structural unit of the following formula (2).

Chemical formula

[0031] The polyhydroxyamide compound of this embodiment may have an alkali-soluble group at its terminal. The alkali-soluble group at the terminal is not particularly limited, and examples thereof include functional groups such as alcoholic hydroxyl groups, phenolic hydroxyl groups, acid anhydride groups, carboxyl groups, sulfonic acid groups, sulfonamide groups, and active methylene groups. From the viewpoint of solubility in a developer, it preferably has a carboxyl group or a phenolic hydroxyl group.

[0032] When the polyhydroxyamide compound of this embodiment is used as a negative photosensitive resin composition, among these alkali-soluble groups, a phenolic hydroxyl group is particularly preferred. When the polyhydroxyamide compound has a phenolic hydroxyl group at its terminal, the solubility of the polyhydroxyamide compound in a developer can be improved. Furthermore, since the phenolic hydroxyl group has lower reactivity compared to the carboxyl group, when used as a photosensitive resin composition in combination with a crosslinking agent or the like, an excessive reaction with the crosslinking agent or the like is suppressed, and even when a PEB process is performed, the solubility of the unexposed portion in the developer can be maintained. It is presumed that a negative photosensitive resin composition excellent in resolution can be provided thereby.

[0033] Also, the alkali-soluble group contained at the terminal of these polyhydroxyamide compounds may be one having as a residue of the monomer constituting the polyhydroxyamide compound, or may be one having as a terminal structure introduced by a terminal capping agent having an alkali-soluble group. The alkali-soluble group contained at the terminal of the polyhydroxyamide compound is preferably one having as a terminal structure introduced by a terminal capping agent having an alkali-soluble group.

[0034] The terminal blocking agent is not particularly limited, and examples thereof include compounds having one amino group and one hydroxyl group such as aminophenol compounds, hydroxybenzylamine compounds, aminobenzyl alcohol compounds, and alcoholamine compounds; compounds having one carboxyl group and one hydroxyl group such as hydroxy acids; acid anhydride compounds having a hydroxyl group such as hydroxy acid anhydrides; compounds having an amino group and a carboxyl group such as aminobenzoic acid and amino acids; acid anhydride compounds such as phthalic anhydride and 5-norbornene-2,3-dicarboxylic anhydride.

[0035] Examples of the method for producing the polyhydroxyamide compound include a method in which a hydroxycarboxylic acid compound represented by the following formula (3) and a diamine compound represented by the following formula (4) are polycondensed using an activator and a condensing agent described later.

Chemical formula

Chemical formula

[0036] As the hydroxycarboxylic acid compound represented by the above formula (3), a hydroxycarboxylic acid compound represented by the following formula (3-1) is preferable.

Chemical formula

[0037] Examples of the hydroxycarboxylic acid compound represented by the above formula (3-1) include methylenedisalicylic acid (MDSA) and 5,5'-thiodisalicylic acid. In this embodiment, MDSA is preferably used. MDSA is shown in the following formula (3-2).

Chemical formula

[0038] As the diamine compound represented by the above formula (4), known diamine compounds can be used without particular limitation. For example, 3,4'-diaminodiphenyl ether (3,4'-ODA), 4,4'-diaminodiphenyl ether, 3,3'-oxydianiline, 4,4'-oxydianiline, 2,7-diaminofluorene, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 4,4'-ethylenedianiline, diethylenetriamine, 1,12-diaminododecane, 1,11-diaminoundecane, 1,10-diaminodecane, 1,9-diaminononane, 1,8-diaminooctane, 1,7-diaminoheptane, 1,6-diaminohexane, 1,5-diaminopentane, 1,4-diaminobutane, 1,3-diaminopropane, ethylenediamine, 3,5-diamino-1,2,4-triazole, benzoguanamine, 1,3-bis(3-aminopropyl)tetramethyldisiloxane Examples thereof include tetramethyl-1,3-bis(3-aminopropyl)disiloxane. Since there are many types of the diamine compound represented by the above formula (4) as described above, according to this embodiment, a wide variety of polyhydroxyamide compounds can be produced, and polyhydroxyamide compounds having various properties can be obtained.

[0039] Other compounds copolymerizable with the above-described compounds may be copolymerized. Examples of other copolymerizable compounds include diol compounds, acid dianhydrides, diisocyanate compounds, and the like.

[0040] In the above polycondensation reaction, the carboxyl group of the hydroxycarboxylic acid compound represented by the above formula (3) is activated by an activator. The activated carboxyl group binds to the amino group portion of the diamine compound represented by the above formula (4) through a condensation reaction with a condensing agent, forming an amide bond. As this condensation reaction proceeds, the polycondensation reaction progresses. The polycondensation reaction proceeds in an appropriate liquid medium. Examples of the liquid medium include water, an aqueous buffer solution (e.g., an acidic buffer solution), and organic solvents such as N-methylpyrrolidone (NMP).

[0041] Examples of the activator include N-hydroxy polyvalent carboxylic acid imides such as N-hydroxysuccinimide (NHS) and n-hydroxy-5-norbornene-2,3-dicarboxylic acid imide (HONB), N-hydroxy triazoles such as 1-hydroxybenzotriazole (HOBt), N-hydroxy triazines such as 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine (HOOBt), ethyl 2-hydroxyimino-2-cyanoacetate, and pentafluorophenol. Among these, HOBt is preferred.

[0042] Examples of the condensing agent include carbodiimide-based condensing agents such as diisopropylcarbodiimide (DIPC), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDAC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), and dicyclohexylcarbodiimide (DCC), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), and carbonyldiimidazole. Among these, EDAC and DMT-MM are preferred.

[0043] The reaction temperature and reaction time of the polycondensation reaction can be appropriately selected from conventionally known reaction conditions. For example, the reaction can be carried out at -20°C to 100°C for 5 minutes to 24 hours.

[0044] The weight average molecular weight (Mw) of the polyhydroxyamide compound can be 2,000 to 20,000, preferably 2,000 to 19,000, more preferably 3,000 to 15,000, and even more preferably 4,000 to 10,000. By setting the range in this way, it becomes possible to form an L / S pattern that is finer and has a higher aspect ratio.

[0045] The number average molecular weight (Mn) of the polyhydroxyamide compound is preferably 1,000 to 10,000, and more preferably 1,500 to 6,000.

[0046] The molecular weight distribution (PDI) of the polyhydroxyamide compound is preferably 1.5 to 25.0, and more preferably 1.5 to 10.0. The molecular weight distribution (PDI) is calculated by the following formula. PDI = Mw / Mn

[0047] When the weight average molecular weight (Mw), number average molecular weight (Mn), and molecular weight distribution (PDI) of the polyhydroxyamide compound are within such ranges, the solubility in the developer in the unexposed portion and the reaction with the crosslinking agent in exposure achieve a suitable balance, and a photosensitive resin composition with excellent resolution can be obtained.

[0048] In this specification, the weight average molecular weight (Mw) and number average molecular weight (Mn) are values measured by gel permeation chromatography (GPC) (GL7700 manufactured by GL Science) and converted using standard polystyrene. The specific measurement conditions are as follows.

[0049] Column: TSKgel αM (manufactured by Tosoh Corporation) Column internal temperature: 40 °C Eluent composition: NMP solution containing 100 mmol / L of H3PO4 (using an 85% aqueous solution of H3PO4 as a raw material) and 10 mmol / L of LiBr Eluent flow rate: 0.5 mL / min Calibration standard reagent: Polystyrene Detector wavelength: 260 nm and 300 nm Detector temperature: Room temperature (about 25 °C) Baseline range during analysis: 15 - 40 minutes Molecular weight calculation range during analysis: 20 - 35 minutes

[0050] The alkali dissolution rate of the polyhydroxyamide compound is not particularly limited, and from the viewpoint of obtaining a photosensitive resin composition excellent in developability and sensitivity, it can be, for example, 10 - 1000 nm / sec, more preferably 50 - 700 nm / sec, and even more preferably 100 - 500 nm / sec. If the alkali dissolution rate is too low, the photosensitive resin composition may not dissolve sufficiently during development, making pattern formation difficult. If the alkali dissolution rate is too high, the sensitivity may decrease or the pattern may swell during development. The alkali dissolution rate of the polyhydroxyamide compound can be measured by the method described in the examples below.

[0051] 2. Photosensitive resin composition The photosensitive resin composition of this embodiment contains the above-described polyhydroxyamide compound. The polyhydroxyamide compound of this embodiment can be used in both negative and positive photosensitive resin compositions.

[0052] The photosensitive resin composition of this embodiment may further contain a crosslinking agent, a photoacid generator, a basic compound, etc.

[0053] 2-1. Crosslinking agent The crosslinking agent is not particularly limited and known ones can be used. For example, melamine compounds, guanamine compounds, triazine compounds, epoxy compounds, oxetane compounds, isocyanate compounds, oxazoline compounds, etc. can be mentioned. The crosslinking agent is preferably a compound having at least one or more selected from the group consisting of a methoxymethyl group and a methylol group. These functional groups use the acid generated from the photoacid generator described later as an active species, and undergo a crosslinking reaction with phenolic hydroxyl groups and carboxyl groups contained in polyhydroxyamide compounds, etc. by heating, so that negative photolithography (pattern formation) is realized by exposure, PEB, and development processes. Further, after pattern formation, by further heating, the curing reaction of the photosensitive resin composition proceeds, and excellent properties as a cured product are exhibited.

[0054] Also, the crosslinking agent preferably contains a heterocyclic ring in order to improve the resolution of the photosensitive resin composition and the insulation reliability after curing. The heterocyclic ring is not particularly limited and contains one or more heteroatoms such as boron, nitrogen, oxygen, phosphorus, sulfur, antimony, arsenic, bismuth, selenium, silicon, tellurium, tin, etc., and includes a saturated or unsaturated ring of a 3-membered ring, 4-membered ring, 5-membered ring, 6-membered ring, 7-membered ring or 8-membered ring. From the viewpoints of the resolution of the photosensitive resin composition and the insulation reliability of the cured product, the heterocyclic ring preferably contains nitrogen, and more preferably contains a plurality of nitrogens.

[0055] Specifically, from the perspective of being able to provide a composition, compounds having a triazine structure such as hexamethylol melamine and hexamethoxymethyl melamine, compounds having a guanamine structure such as tetramethylol benzoguanamine and tetramethoxymethyl benzoguanamine, compounds having a glycoluril structure such as tetramethylol glycoluril and tetramethoxyglycoluril, and compounds having an imidazolidinone structure such as 1,3-bis(methoxymethyl)-2-imidazolidinone are more preferred. Among these, particularly from the perspective of being able to provide a negative photosensitive resin composition capable of forming a finer and higher aspect ratio L / S pattern, compounds having a triazine structure containing a triazine ring and compounds having a guanamine structure can be preferably used.

[0056] 2-2. Photoacid generator The photoacid generator is not particularly limited as long as it is a compound that generates an acid upon irradiation with light such as ultraviolet light or visible light. Examples include naphthoquinone diazide compounds, diaryl sulfonium salts, triaryl sulfonium salts, dialkyl phenacyl sulfonium salts, diaryl iodonium salts, aryldiazonium salts, aromatic tetracarboxylic acid esters, aromatic sulfonic acid esters, nitrobenzyl esters, aromatic N-oxyamide sulfonates, aromatic N-oxyimide sulfonates, aromatic sulfamides, oxime sulfonate compounds, naphthalimides, and benzoquinone diazosulfonic acid esters. These can be used alone or in combination of a plurality at an arbitrary ratio.

[0057] When the polyhydroxyamide compound of this embodiment is used as a negative photosensitive resin composition, the photoacid generator is preferably used in combination with the crosslinking agent described above, and the photoacid generator is preferably an oxime sulfonate compound. Examples of the oxime sulfonate compound include Irgacure PAG103, Irgacure PAG108, Irgacure PAG121, and Irgacure PAG203 manufactured by BASF, and those containing the structure of the following formula (5) are particularly preferred. [Chemical formula] (In formula (5), X is a hydrocarbon group or a halogen atom, m is an integer from 0 to 3, and R3 is a hydrogen atom, a hydrocarbon group, an organic group containing a ketone group, or a halogen atom.)

[0058] X in the above formula (5) is not particularly limited and can be, for example, a hydrocarbon group (such as an alkyl group, an alkenyl group, an alkynyl group, an aryl group, etc.) or a halogen atom. The hydrocarbon group may have a substituent and can have a linear, branched, or cyclic structure. A linear or branched hydrocarbon group having 1 to 4 carbon atoms is preferably used. As the halogen atom, a chlorine atom or a fluorine atom is preferably used.

[0059] m in the above formula (5) represents an integer from 0 to 3, and 0 or 1 is preferred. When m is 2 or 3, the plurality of Xs may be the same or different.

[0060] R3 in the above formula (5) is preferably a hydrogen atom, a hydrocarbon group, an organic group containing a ketone group, or a halogen atom. The hydrocarbon group (such as an alkyl group, an alkenyl group, an alkynyl group, an aryl group, etc.) may be unsubstituted or may be substituted with a halogen atom.

[0061] The hydrocarbon group is preferably linear, branched, or cyclic with 1 to 20 carbon atoms, and more preferably linear, branched, or cyclic with 1 to 10 carbon atoms. The halogen atom may be a chlorine atom or a fluorine atom.

[0062] When the polyhydroxyamide compound of the present embodiment is used as a positive photosensitive resin composition, the photoacid generator is preferably a dissolution inhibitor and preferably a naphthoquinonediazide compound. Examples of the naphthoquinonediazide compound include naphthoquinonediazide adducts of tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (for example, TKF-520, TKF-528, TKF-420, TKF-428 manufactured by Sanpo Chemical Laboratory), naphthoquinonediazide adducts of tetrahydroxybenzophenone (for example, BS550, BS570, BS599 manufactured by Sanpo Chemical Laboratory), etc. Here, for the addition of naphthoquinonediazide, for example, o-quinonediazide sulfonyl chlorides may be reacted with hydroxy compounds or amino compounds. These can be used alone or in combination of a plurality at an arbitrary ratio.

[0063] 2-3. Basic Compound The photosensitive resin composition of the present embodiment may contain a basic compound. In particular, when the photosensitive resin composition of the present embodiment contains a basic compound, it is possible to suppress the diffusion of the acid generated from the photoacid generator by exposure to the unexposed portion, so that the resolution can be improved and development residues can be prevented from occurring in the unexposed portion after development.

[0064] The basic compound is not particularly limited. For example, amine compounds such as trimethylamine, diethylamine, triethylamine, N,N-diisopropylethylamine, di-n-propylamine, tri-n-propylamine, tri-n-pentylamine, tribenzylamine, diethanolamine, triethanolamine, tris(2-methoxy)amine, bis(2-methoxy)amine, tris(2-ethoxy)amine, bis(2-ethoxy)amine, N-methyldiethanolamine, N-ethyldiethanolamine, N,N-dimethylethanolamine, n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, ethylenediamine, N,N,N’,N’-tetramethylethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4’-diaminodiphenylmethane, 4,4’-diaminodiphenyl ether, 4,4’-diaminobenzophenone, 4,4’-diaminodiphenylamine; amide compounds such as formamide, N-methylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, propionamide, benzamide; lactams such as pyrrolidone, N-methylpyrrolidone; urea compounds such as methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea; nitrogen-containing heterocyclic compounds such as imidazole, benzimidazole, 4-methylimidazole, 8-hydroxyquinoline, acridine, purine, pyrrolidine, piperidine, 2,4,6-tri(2-pyridyl)-S-triazine, piperazine, 1,4-dimethylpiperazine, 1,4-diazabicyclo[2.2.2]octane, pyridine; morpholine compounds such as morpholine, 4-methylmorpholine; etc. can be mentioned. These can be used alone or in combination of a plurality at any ratio. Among these, amine compounds are preferred, alcohol amines such as N-methyldiethanolamine, N-ethyldiethanolamine, N,N-dimethylethanolamine are more preferred, and diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N,N-dimethylethanolamine are even more preferred.

[0065] 2-4. Solvent The photosensitive resin composition of this embodiment can contain a solvent. The solvent is not particularly limited, and examples thereof include ethers, esters, glycol esters, ketones, lactones, lactams, sulfoxides, tetramethylurea, dimethyl sulfone, pyridine, and the like.

[0066] Examples of ethers include 2-methoxy-1-methylethyl acetate (PGMEA), ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, propylene glycol dimethyl ether, dipropylene glycol dimethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, and the like.

[0067] Examples of esters include ethyl acetate, butyl acetate, ethyl lactate, methyl 3-methoxypropionate, methyl 2-methoxypropionate, ethyl 3-methoxypropionate, ethyl 2-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 2-ethoxypropionate, and the like.

[0068] Examples of ketones include methyl ethyl ketone; methyl isobutyl ketone (4-methyl-2-pentanone); 2-heptanone; Cycloalkanones which are monoketones such as cyclopropanone, cyclobutanone, cyclopentanone, cyclohexanone, methylcyclohexanone, cycloheptanone, cyclooctanone, 2-norbornanone, 2-methylcyclohexanone, 4-methylcyclohexanone, 3-methylcyclohexanone, 2,2-dimethylcyclopentanone; Cycloalkanones such as diketones including 1,3 - cyclopentanedione, 3 - methyl - 1,2 - cyclopentanedione, 1,2 - cyclohexanedione, 1,3 - cyclohexanedione, 1,4 - cyclohexanedione, 2 - methyl - 1,3 - cyclopentanedione, etc.; Cycloalkenones such as 4 - methyl - 2 - cyclopentenone, 2 - cyclohexenone, 2 - cyclopenten - 1 - one, 2 - cyclohexen - 1 - one, etc.; Cyclic ketones having a heterocyclic skeleton such as 2 - azetidinone, 4,5 - dihydro - 3(2H) - thiophenone, 4 - oxothiane, dihydroreboglucosen, etc. can be mentioned. etc.;

[0069] Examples of glycol esters include carbitol acetate, ethyl cellosolve acetate, ethylene glycol monoethyl ether acetate, etc.

[0070] Examples of lactones include γ - butyrolactone, etc., examples of lactams include N - methylpyrrolidone, N - methylcaprolactam, etc., and examples of sulfoxides include dimethyl sulfoxide, hexamethyl sulfoxide, etc.

[0071] These solvents can be used alone or in any ratio combination of a plurality. Among these solvents, from the viewpoint of excellent affinity with each component in the negative - type photosensitive resin composition, lactones or cyclic ketones are preferred, and γ - butyrolactone or cyclopentanone is preferred. Also, from the viewpoint of excellent solvent removability during drying of the negative - type photosensitive resin composition and compatibility with the edge rinse process in semiconductor manufacturing, cyclic ketones are preferred, cycloalkanones which are monoketones are more preferred, and cyclopropanone, cyclobutanone, cyclopentanone, cyclohexanone, methylcyclohexanone, cycloheptanone, cyclooctanone, 2 - norbornanone, 2 - methylcyclohexanone, 4 - methylcyclohexanone, 3 - methylcyclohexanone, 2,2 - dimethylcyclopentanone are even more preferred, and cyclopentanone is particularly preferred.

[0072] 2-5. Other components The photosensitive resin composition of this embodiment can contain other components as long as the effects of the disclosed technology are not impaired. As the other components, known components that can be contained in the photosensitive resin composition can be used. For example, fillers, adhesives, surfactants, plasticizers, thermal acid generators, sensitizers, leveling agents, colorants, fibers, fine particles, etc. can be mentioned.

[0073] The surfactant is not particularly limited, and examples include fluorine-based surfactants, silicone-based surfactants, etc. Commercially available products of fluorine-based surfactants include the "Megafac" series manufactured by DIC Corporation (for example, Megafac F-281, F-477, F-553, F-554, F-555, F-556, F-557, F-558, F-559, F-560, F-561, F-563, F-569, etc.). Commercially available products of silicone-based surfactants include the surface conditioner series of BYK Chemie (for example, BYK-302, BYK-307, BYK-310, BYK-322, BYK-323, BYK-326, BYK-331, BYK-332, BYK-333, BYK-348, BYK-349, BYK-377, BYK-378, BYK-3455, BYK-3760, etc.). These can be used alone or in combination of two or more.

[0074] 3. Preparation of the photosensitive resin composition The photosensitive resin composition of this embodiment can be obtained by mixing arbitrary components including components such as a crosslinking agent, a photoacid generator, and a basic compound in addition to the polyhydroxyamide compound described above. The mixing of each component can be carried out under heating as necessary.

[0075] 3-1. Polyhydroxyamide compound The content of the polyhydroxyamide compound can be 50 to 80% by mass based on 100% by mass of the total solid content of the photosensitive resin composition. Here, the solid content mass in this specification refers to the mass of the residue after completely volatilizing the volatile components.

[0076] 3-2. Crosslinking agent The content of the crosslinking agent can be 10 to 40% by mass based on 100% by mass of the total solid content of the photosensitive resin composition. When the crosslinking agent has a methoxymethyl group and / or a methylol group, the content of the crosslinking agent can be such that the ratio of the number of methoxymethyl groups and / or methylol groups contained in the crosslinking agent to the number of phenolic hydroxyl groups contained in the photosensitive resin composition (methoxymethyl group and / or methylol group: phenolic hydroxyl group) is 120:100 to 200:100. By setting such a ratio, the resolution of the photosensitive resin composition and the insulation reliability after curing can be made more excellent.

[0077] 3-3. Photoacid generator The content of the photoacid generator can be 0.5 to 10% by mass based on 100% by mass of the total solid content of the photosensitive resin composition, and preferably 1 to 5% by mass.

[0078] 3-4. Basic compound When adding a basic compound, the content can be 0.01 to 0.50% by mass based on 100% by mass of the total solid content of the photosensitive resin composition, and preferably 0.08 to 0.40% by mass. By setting such a range, it becomes easier to suppress the generation of development residues in the unexposed areas after developing the photosensitive resin composition.

[0079] 4. Dry film The dry film of this embodiment includes a base material and a resin layer formed on this base material using the photosensitive resin composition of this embodiment. Further, for the protection of the resin layer, a protective film may be laminated on the surface of the resin layer.

[0080] The resin layer can be obtained, for example, by applying a photosensitive resin composition onto a substrate, adjusting the thickness of the resin layer using a comma coater, blade coater, lip coater, rod coater, squeeze coater, reverse coater, transfer roll coater, gravure coater, spray coater, etc., and then drying it. The thickness of the resin layer is not particularly limited and can be set to 1 to 150 μm according to the application.

[0081] The substrate is not particularly limited, and examples thereof include metal foils such as copper foil; films such as polyimide film, polyester film, polyethylene naphthalate (PEN) film, etc.

[0082] The protective film is not particularly limited, and polyethylene film, polytetrafluoroethylene film, polypropylene film, paper, etc. can be used. It is preferable to select a protective film having an adhesive strength between the protective film and the resin layer lower than the adhesive strength between the substrate and the resin layer. In order to make the adhesive strength between the protective film and the resin layer lower than the adhesive strength between the substrate and the resin layer, a protective film whose surface has been subjected to a peeling treatment can be used.

[0083] 5. Cured Product The cured product of this embodiment is obtained by curing the resin layer of the above-described photosensitive resin composition or dry film. The cured product may be a patterned cured product. The manufacturing method of the patterned cured product will be described below by taking the case of a negative photosensitive resin composition as an example.

[0084] 5-1. Dry Coating Film Formation Step The dry coating film formation step is a step of applying the above-described photosensitive resin composition onto a substrate to form a coating film and then drying it. The dry coating film formation step can also form a dry coating film on the substrate by transferring the resin layer of the dry film onto the substrate.

[0085] The method of applying the photosensitive resin composition onto the substrate is not particularly limited. For example, methods of application using a spin coater, bar coater, blade coater, curtain coater, screen printing machine, etc., a method of spray coating with a spray coater, an inkjet method, etc. can be mentioned. The coating film thickness is not particularly limited and can be, for example, 10 μm or less, 5 μm or less, 3 μm or less. By making the film thickness thinner, finer L / S patterning becomes possible while maintaining the aspect ratio of the pattern.

[0086] The method of drying the coating film is not particularly limited. For example, air drying, heat drying using an oven or hot plate, vacuum drying, etc. can be mentioned. The conditions when performing heat drying are, for example, a heating temperature of 70 to 140 °C and a drying time of 1 to 30 minutes.

[0087] The transfer of the resin layer of the dry film onto the substrate is preferably performed under pressure and heating using a vacuum laminator or the like. The heating temperature can be, for example, 60 to 100 °C.

[0088] The substrate is not particularly limited and can be, for example, a printed wiring board on which a circuit is formed, a flexible printed wiring board, a wafer on which a semiconductor element is formed.

[0089] 5 - 2. Exposure process The exposure process is a process of irradiating radiation through a photomask capable of forming a desired pattern on the dry coating film formed in the dry coating film forming process, thereby sensitizing the photoacid generator in the exposed portion and generating active species. When patterning is not required, there is no need to use a photomask. Also, a pattern may be directly drawn with a laser using a direct drawing apparatus.

[0090] As the wavelength of the radiation, those having a wavelength capable of activating the photoacid generator are used. In order to perform miniaturized patterning, those having a maximum wavelength of 410 nm or less are preferable. The irradiation energy can be adjusted according to the thickness of the formed dry coating film, etc. and is, for example, 10 to 1500 mJ / cm 2It can be used. As the exposure light source, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, a mercury short arc lamp, a KRF laser, etc. can be used.

[0091] 5-3. PEB Process The PEB process is a process of heat-treating a dry coating film composed of a photosensitive resin composition exposed in the exposure process and imparting developability resistance to the exposed portion of the dry coating film (hereinafter, may be abbreviated as the exposed portion). In the PEB process, using the acid generated from the photoacid generator at the exposed portion as an active species, the crosslinking reaction between the polyhydroxyamide compound or the compound containing a phenolic hydroxyl group and the crosslinking agent proceeds, and the exposed portion becomes insoluble in the developer. The heating temperature in the PEB process can be 90 to 150 °C, and the heating time can be 0.5 to 10 minutes. The heating can be performed by a known method such as a hot plate or a heating furnace.

[0092] 5-4. Development Process The development process is a process of treating the dry coating film heated in the PEB process with a developer to obtain a pattern coating film. More specifically, a pattern coating film can be obtained by dissolving and removing the unexposed portion of the dry coating film with the developer. As the development method, a known method can be used, for example, the rotary spray method, the paddle method, the dipping method with ultrasonic treatment, etc. can be mentioned.

[0093] As the developer, a known one can be used, for example, aqueous solutions of inorganic alkalis such as sodium hydroxide, sodium carbonate, sodium silicate, aqueous ammonia, organic amines such as ethylamine, diethylamine, triethylamine, triethanolamine, quaternary ammonium salts such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide, etc. can be mentioned. If necessary, water-soluble organic solvents such as methanol, ethanol, isopropyl alcohol, and surfactants can be added.

[0094] After treatment with the developer, if necessary, the coating film can be washed with a rinsing solution to obtain a patterned coating film. The rinsing solution is not particularly limited, and examples thereof include pure water, methanol, ethanol, isopropyl alcohol, and the like. These can be used alone or in combination of two or more at an arbitrary ratio.

[0095] 5-5. Post-development heating step The post-development heating step is a step of heating the patterned coating film formed in the development step to complete the curing of the patterned coating film and obtain a cured patterned coating film (cured product). The heating temperature can be 150 to 200 °C, and the heating time can be 1 to 120 minutes. Heating can be performed by a known method such as a hot plate or an inert oven, and it is desirable to perform heating under a nitrogen atmosphere.

[0096] In addition, when the photosensitive resin composition of this embodiment is a positive photosensitive resin composition, a dissolution inhibitor is used as a photoacid generator, and the coating film is treated with a developer in the above-described development step, whereby the exposed portion of the dry coating film is dissolved and removed by the developer to obtain a patterned coating film.

[0097] 6. Uses of the photosensitive resin composition The photosensitive resin composition of the present embodiment can be suitably used as a forming material for display devices, semiconductor elements, electronic components, optical components, building materials, and the like. The forming material for semiconductor elements is, for example, a resist material, a buffer coat film, or an insulating film for a redistribution layer of a wafer-level package (WLP). Examples of the forming material for electronic components include printed wiring boards, interlayer insulating films, and wiring coating films.

Examples

[0098] Hereinafter, the present invention will be described with reference to Examples and Comparative Examples, but the present invention is not limited thereto. Each component used in the Examples and Comparative Examples is as follows.

[0099] <Polyhydroxyamide compound> The polyhydroxyamide compounds (A-1) to (A-7) were synthesized as follows. The compounding components, addition molar ratios, and the weight average molecular weight (Mw), number average molecular weight (Mn), and molecular weight dispersity (PDI) of the obtained polyhydroxyamide compounds (A-1) to (A-7) are shown in Table 1 below.

[0100] (Synthesis Example 1: Polyhydroxyamide Compound (A-1)) In a 100 mL flask equipped with a stirrer and a thermometer (at room temperature), 9.050 g (31.40 mmol) of methylenedisalicylic acid (MDSA) (isomer mixture), 5.730 g (28.57 mmol) of 3,4'-diaminodiphenyl ether (3,4'-ODA), 3.050 g (27.95 mmol) of 3-aminophenol (3AP), and 10.10 g (65.95 mmol) of 1-hydroxybenzotriazole monohydrate (HOBt) were stirred and dissolved in 71.00 g of N-methylpyrrolidone (NMP) for 15 minutes. Then, the flask was immersed in an ice bath, and while maintaining the inside of the flask at 0 to 5 °C, 10.23 g (65.92 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDAC) was added over 15 minutes, and the mixture was stirred in the ice bath for 30 minutes. After stirring at room temperature for 12 hours, the solution was poured into a large amount of methanol, and the precipitate was collected. The obtained solid was dissolved in 71 g of tetrahydrofuran. The obtained solution was poured into a large amount of methanol, and the precipitate was collected. After collecting the precipitated solid, it was dried under reduced pressure at 100 °C for 5 hours to obtain the polyhydroxyamide compound (A-1).

[0101] (Synthesis Example 2: Polyhydroxyamide Compound (A-2)) A polyhydroxyamide compound (A-2) was obtained in the same manner as in Synthesis Example 1, except that the addition molar ratios of methylenedisalicylic acid (MDSA) (isomer mixture), 3,4'-diaminodiphenyl ether (3,4'-ODA), and 3-aminophenol (3AP) were as shown in Table 1 below.

[0102] (A-1) to (A-2) Polyhydroxyamide Compounds [Chemical Formula]

[0103] (Activator) 1-Hydroxybenzotriazole monohydrate (HOBt) [Chemical formula]

[0104] (Condensing agent) 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide (EDAC) [Chemical formula]

[0105] Regarding the polyhydroxy compound (A-1), 1 1H-NMR measurement was performed. For the measurement, a nuclear magnetic resonance apparatus (manufactured by JEOL Ltd., JNM-ECA400II) was used. In Fig. 1, the 1 1H-NMR measurement results of the polyhydroxy compound (A-1) are shown. Also, in Fig. 2, the 1 positions of the hydrogens corresponding to the peaks in the 1H-NMR chart of the polyhydroxy compound (A-1) are shown.

[0106] From Fig. 1 and Fig. 2, in the polyhydroxy compound (A-1), the peak (a) corresponding to the hydrogen of the aromatic ring derived from MDSA, the peak (b) corresponding to the hydrogen of the amide group, the peak (c) corresponding to the hydrogen of -CH2- derived from MDSA, and the peak (d) corresponding to the hydrogen of the aromatic ring derived from 3,4'-ODA could be confirmed.

[0107] (Synthesis Example 3: Polyhydroxyamide Compound (A-3)) Polyhydroxyamide compound (A-3) was obtained in the same manner as in Synthesis Example 1, except that 3,4'-methylenedianiline (3,4'-MDA) was used instead of 3,4'-ODA and the added molar ratio of each component was as described in Table 1 below.

[0108] (A-3) Polyhydroxyamide compound [Chemical formula]

[0109] (Synthesis Example 4: Polyhydroxyamide Compound (A-4)) A polyhydroxyamide compound (A-4) was obtained in the same manner as in Synthesis Example 1, except that 1,3-bis(3-aminopropyl)tetramethyldisiloxane (BADS) was used instead of 3,4'-ODA and the addition molar ratio of each component was as described in Table 1 below.

[0110] (A-4) Polyhydroxyamide compound [Chemical formula]

[0111] (Synthesis Example 5: Polyhydroxyamide Compound (A-5)) A polyhydroxyamide compound (A-5) was obtained in the same manner as in Synthesis Example 1, except that 1,3-bis(3-aminopropyl)tetramethyldisiloxane (BADS) and benzoguanamine (BG) were used instead of 3,4'-ODA and the addition molar ratio of each component was as described in Table 1 below.

[0112] (A-5) Polyhydroxyamide compound [Chemical formula]

[0113] (Synthesis Example 6: Polyhydroxyamide Compound (A-6)) A polyhydroxyamide compound (A-6) was obtained in the same manner as in Synthesis Example 1, except that 1,3-bis(3-aminopropyl)tetramethyldisiloxane (BADS) was used instead of 3,4'-ODA, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was used instead of EDAC, and triethylamine (Et3N) was used instead of HOBt, and the addition molar ratio of each component was as described in Table 1 below.

[0114] (A-6) Polyhydroxyamide compound

Chem.

[0115] (Synthesis Example 7: Polyhydroxyamide compound (A-7)) In a 120 mL vial equipped with a stirrer and a thermometer (at room temperature), 6.85 g (24.4 mmol) of 2,2-bis(3-amino-4-hydroxyphenyl)sulfone (SO2AP) was used. After 0.860 g (7.87 mmol) of 3-aminophenol (3AP) was stirred and dissolved in 35 g of N-methylpyrrolidone (NMP), the vial was immersed in an ice bath. While maintaining the temperature inside the vial at 0 - 5 °C, 7.54 g (25.5 mmol) of 4,4'-oxybis(benzoyl chloride) (DEDC) was added in solid form over 10 minutes, and the mixture was stirred in the ice bath for 30 minutes. After stirring at room temperature for 18 hours, the solution was poured into a large amount of ion-exchanged water, and the precipitate was collected. The obtained solid was dissolved in 33 g of cyclopentanone. 5 g of an anion exchange resin (Amberlyst B-20 from Organo) was added thereto, and the mixture was vigorously stirred for 1 hour. After the stirred solution was concentrated, it was poured into a large amount of ion-exchanged water, and the precipitate was collected. After the precipitated solid was recovered, it was dried under reduced pressure to obtain the polyhydroxyamide compound (A-7).

[0116] (A-7) Polyhydroxyamide compound

Chem.

[0117] The following evaluations were performed on the polyhydroxyamide compound obtained in the above synthesis example. The evaluation results are shown in Table 1 below.

[0118] (Evaluation of alkali solubility) Using the polyhydroxyamide compound obtained in the above synthesis example, 20% by mass N-methylpyrrolidone (NMP) solutions were prepared respectively. The prepared solutions were spin-coated on a silicon substrate and dried by heating at 90 °C for 3 minutes using a hot plate to form a dry coating film of the polyhydroxyamide compound. After measuring the initial film thickness of the dry coating film with an optical interference film thickness meter, it was developed using an aqueous solution of 2.38% tetramethylammonium hydroxide (TMAH) at 25 °C, the dissolution time of the dry coating film was measured, and the alkali dissolution rate was calculated from the following formula. Alkali dissolution rate (nm / s) = Initial film thickness (nm) / Dissolution time (s) (Evaluation criteria) A: Dissolution rate is 50 nm / s or more and 500 nm / s or less B: Dissolution rate exceeds 500 nm / s C: Does not have alkali solubility, or the alkali dissolution rate is extremely slow (less than 50 nm / s) and the dissolution time cannot be measured

[0119]

Table 1

[0120] <Crosslinking agent> (B) MW-390 (Hexamethoxymethylmelamine compound manufactured by Nippon Carbide Industries Co., Ltd.)

Chemical formula

[0121] <Photoacid generator> (C) PAG-103 (Oxime sulfonate compound manufactured by BASF)

Chemical formula

[0122] <Basic compound> (D) Triethanolamine (TEA) [Chemical]

[0123] [Solvent] Cyclopentanone (manufactured by Tokyo Chemical Industry Co., Ltd.) Dimethyl sulfoxide (DMSO) (manufactured by Fujifilm Wako Pure Chemical Corporation) N-Methylpyrrolidone (NMP) (manufactured by Fujifilm Wako Pure Chemical Corporation)

[0124] [Surfactant] BYK-310 (a polyester-modified silicone-based surfactant manufactured by BYK-Chemie GmbH)

[0125] [Preparation of Photosensitive Resin Composition] Each component was blended in the amounts shown in Table 2 below, and dissolved and adjusted so that the concentration of the non-volatile components in the varnish became 30%, thereby obtaining the varnishes of the photosensitive resin compositions of each example and comparative example. Note that, among the blending amounts of each component in Table 2 below, the amounts other than the blending amount of the solvent are shown in parts by mass of the solid content.

[0126] [Evaluation] The following evaluations were performed using the obtained photosensitive resin compositions of each example and comparative example. The results of each evaluation are shown in Table 2 below.

[0127] [Evaluation of Resolution and Sensitivity] The varnishes of each example and comparative example were applied onto a silicon wafer using a spin coater so that the film thickness after curing became 3.8 μm, and dried at 90°C for 3 minutes using a hot plate to obtain the dried coating films of the photosensitive resin compositions of each example and comparative example. A contact exposure machine (UVE-251S + EL-100 (manufactured by San-Ei Electric Co., Ltd.)) was used to expose a test pattern with an L / S of 2 / 2 μm to 10 / 10 μm at 1-μm intervals on this dried coating film, and post-exposure baking (PEB) was performed at 130°C for 60 seconds using a hot plate. The heating temperature in the PEB process was 130°C. Thereafter, development was performed for 30 seconds using a 2.38% TMAH aqueous solution, rinsing was performed with ultrapure water for 30 seconds, and spin drying was performed for 30 seconds to obtain a sample having a pattern.

[0128] Each sample was cut so that a cross-section perpendicular to the longitudinal direction of the pattern could be observed. The cut surface of the pattern was observed using a scanning electron microscope (observation magnification: 10,000 times), and the size of the minimum L / S that was normally patterned and the exposure amount at that time were described in Table 2 below. It shows that the smaller the size of the minimum L / S, the better the resolution, and the smaller the exposure amount, the better the sensitivity. Samples in which each pattern was vertically patterned without falling over were judged to be normally patterned. The pattern shape was evaluated according to the following evaluation criteria. (Evaluation Criteria) A: A substantially rectangular pattern is formed. C: A substantially rectangular pattern is not formed, or a pattern larger than the desired L / S width is formed due to swelling of the pattern or the like.

[0129]

Table 2

Industrial Applicability

[0130] The polyhydroxyamide compound of the present invention is a novel polyhydroxyamide compound that can be used in resin compositions such as photosensitive resin compositions, and thus can be suitably used as a forming material for display devices, semiconductor elements, electronic components, optical components, building materials, etc.

Claims

1. A polyhydroxyamide compound having a structural unit of the following formula (1). 【Chemical 1】 (R in formula (1) １ , R ２ each independently represents a divalent organic group, and ring A and ring B represent divalent groups having a monocyclic or polycyclic aromatic group. However, at least one of R １ , ring A, and ring B contains one or more phenolic hydroxyl groups.)

2. The polyhydroxyamide compound according to Claim 1, wherein at least one of ring A or ring B in the formula (1) contains one or more phenolic hydroxyl groups.

3. The polyhydroxyamide compound according to Claim 1, wherein the formula (1) contains a structural unit of the following formula (2). [Chemical Formula 2] (In formula (2), R １ , R ２ each independently represents a divalent organic group.)

4. A photosensitive resin composition comprising the polyhydroxyamide compound according to Claim 1.

5. A dry film comprising a resin layer formed by the photosensitive resin composition according to Claim 4.

6. A cured product obtained by curing the resin layer of the photosensitive resin composition according to Claim 4 or the dry film according to Claim 5.

7. An electronic component having the cured product according to Claim 6.

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