JP7264688B2 - Photosensitive resin composition, dry film, cured product, and electronic component - Google Patents

Description

TECHNICAL FIELD The present invention relates to photosensitive resin compositions, dry films, cured products, and electronic parts.

Alkali-soluble resins such as photosensitive polyimide and polybenzoxazole (PBO), which are alkali-soluble resins, are used for buffer coat films of semiconductor devices such as LSIs and insulating films for rewiring of wafer level packages (WLP). Photosensitive resin compositions containing precursors are widely used. For example, a photosensitive resin composition that does not leave development residue (scum) on a wafer and enables high-sensitivity patterning includes an alkali-soluble resin, a diazonaphthoquinone compound, and a compound that does not contain a phenolic hydroxyl group but contains a methylol group. , a photosensitive resin composition has been proposed (see Patent Document 1).

As a method for forming a patterned cured insulating film using a photosensitive resin composition containing such a precursor, for example, the photosensitive resin composition is applied onto a substrate such as a wafer, and dried. A dry coating film is formed, the dry coating film is irradiated with an active energy ray, exposed, and then developed to form a desired pattern film, followed by a cyclization reaction at a temperature of about 320° C. and curing A common method is to

On the other hand, in rewiring of WLP, insulating layers and conductive circuits are alternately stacked in multiple layers due to miniaturization of semiconductor elements and multi-layer wiring due to high wiring density.
In the case of such multi-layer wiring, especially in the case of a photosensitive resin composition containing a precursor of a heat-resistant resin, a resin composition for forming an upper insulating layer is applied on the upper layer of the insulating layer to be the lower layer. As a result, the lower insulating layer is exposed to the solvent contained in the resin composition for forming the upper insulating layer, and there is a new problem that cracks are likely to occur in the lower insulating layer. they noticed.

In recent years, a so-called chip-first type fan-out wafer-level packaging method has emerged, in which rewiring is formed after semiconductor chips (dies) obtained by dicing a circuit-formed wafer are sealed with an epoxy resin sealing material. there is As an insulating material for rewiring used in such a construction method, a material that can be cured at a temperature of about 220° C. is required from the viewpoint of the heat resistance of epoxy resin. The inventors have noticed that there is also a problem that properties such as toughness and toughness are deteriorated.

Such a problem has not yet been solved by the technique of Patent Literature 1 described above.

JP-A-2005-37925

Accordingly, an object of the present invention is to provide a photosensitive resin composition that can be cured at a temperature of about 220° C. and has particularly excellent properties in terms of chemical resistance, dielectric properties, and toughness as cured products, dry films, cured products, It is to provide electronic parts.

The present inventors have made intensive studies toward the realization of the above object, and have found that by combining and blending a polybenzoxazole precursor and a compound having two allyl groups, polybenzoxazole or a polybenzoxazole precursor and Focusing on the formation of a so-called interpenetrating polymer network structure in which the allyl compound and the polymer are entangled with each other due to the self-reaction of the allyl compound, a photosensitive resin composition that forms such a molecular structure solves the above problems. The inventors have found that it is possible to do so, and have completed the present invention.

That is, the present invention
Provided is a photosensitive resin composition comprising (A) a polybenzoxazole precursor, (B) a photosensitizer, and (C) a compound containing two allyl groups in the molecule.

The present invention also provides a dry film, comprising a resin layer obtained by applying the photosensitive resin composition to a film and drying the film.

The present invention also provides a cured product obtained by curing the photosensitive resin composition or the resin layer of the rye film.

Moreover, this invention provides the electronic component characterized by having the said hardened|cured material.

According to the present invention, a photosensitive resin composition that can be cured at a low temperature of 220 ° C. or less, and has particularly excellent properties in terms of chemical resistance, dielectric properties, and toughness as a cured product, a dry film, a cured product, and an electronic component. can be provided.

In the present application, when the compounds described have isomers, all possible isomers can be used in the present invention unless otherwise specified.

1. Photosensitive resin composition The photosensitive resin composition of the present invention contains (A) a polybenzoxazole precursor, (B) a photosensitive agent, and (C) a compound containing two allyl groups in the molecule. , is a photosensitive resin composition.
The photosensitive resin composition of the present invention is described in detail below.

1-1. (A) Polybenzoxazole precursor The photosensitive resin composition of the present invention contains (A) a polybenzoxazole precursor.
The method for synthesizing this (A) polybenzoxazole precursor is not particularly limited, and it can be synthesized by a known method. For example, it can be obtained by reacting a dihydroxydiamine as an amine component with a dihalide of a dicarboxylic acid such as a dicarboxylic acid dichloride as an acid component.

（式中、Ｘは４価の有機基を示し、Ｙは２価の有機基を示す。ｎは１以上の整数であり、好ましくは１０～５０、より好ましくは２０～４０である。） (A) The polybenzoxazole precursor is preferably a polyhydroxyamide having a repeating structure represented by the following formula (1).
(Formula 1)

(Wherein, X represents a tetravalent organic group, Y represents a divalent organic group, n is an integer of 1 or more, preferably 10 to 50, more preferably 20 to 40.)

(A) When synthesizing a polybenzoxazole precursor by the above synthesis method, in the general formula (1), X is the residue of the dihydroxydiamines, and Y is the residue of the dicarboxylic acid. .

Examples of the dihydroxydiamines include 3,3′-diamino-4,4′-dihydroxybiphenyl, 4,4′-diamino-3,3′-dihydroxybiphenyl, bis(3-amino-4-hydroxyphenyl)propane, Bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4 -hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexa fluoropropane and the like. Among them, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane is preferred.

Examples of the dicarboxylic acid include isophthalic acid, terephthalic acid, 5-tert-butylisophthalic acid, 5-bromoisophthalic acid, 5-fluoroisophthalic acid, 5-chloroisophthalic acid, 2,6-naphthalenedicarboxylic acid, and 4,4′. -dicarboxybiphenyl, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxytetraphenylsilane, bis(4-carboxyphenyl)sulfone, 2,2-bis(p-carboxyphenyl)propane, 2,2 -Dicarboxylic acids having aromatic rings such as bis(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropane, oxalic acid, malonic acid, succinic acid, 1,2-cyclobutanedicarboxylic acid, Aliphatic dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid and 1,3-cyclopentanedicarboxylic acid are included. Among them, 4,4'-dicarboxydiphenyl ether is preferred.

In the general formula (1), the tetravalent organic group represented by X may be an aliphatic group or an aromatic group, but is preferably an aromatic group, and two hydroxy groups and two amino groups are at the ortho positions. Positioning on an aromatic ring is more preferred. The tetravalent aromatic group preferably has 6 to 30 carbon atoms, more preferably 6 to 24 carbon atoms. Specific examples of the tetravalent aromatic group include, but are not limited to, the following functional groups, and a known aromatic group that can be contained in the polybenzoxazole precursor is selected depending on the application. can do.

Among the aromatic groups, the tetravalent aromatic group is preferably the following group.

In the general formula (1), the divalent organic group represented by Y may be an aliphatic group or an aromatic group, but is preferably an aromatic group, and the carbonyl in the general formula (1) on the aromatic ring It is more preferable that the The divalent aromatic group preferably has 6 to 30 carbon atoms, more preferably 6 to 24 carbon atoms. Specific examples of the divalent aromatic group include, but are not limited to, the following groups, and any known aromatic group contained in the polybenzoxazole precursor may be selected depending on the application. good.

（式中、Ａは単結合、－ＣＨ_２－、－Ｏ－、－ＣＯ－、－Ｓ－、－ＳＯ_２－、－ＮＨＣＯ－、－Ｃ（ＣＦ_３）_２－、－Ｃ（ＣＨ_３）_２－からなる群から選択される２価の基を表す。）

(wherein A is a single bond, -CH ₂ -, -O-, -CO-, -S-, -SO ₂ -, -NHCO-, -C(CF ₃ ) ₂ -, -C(CH ₃ ) ₂ represents a divalent group selected from the group consisting of -.)

Among the aromatic groups, the divalent organic group is preferably the following group.

(A) The polybenzoxazole precursor can contain two or more repeating structures of the above polyhydroxyamic acid. Moreover, it may contain a structure other than the repeating structure of the polyhydroxyamic acid described above, and may contain, for example, a repeating structure of polyamic acid.

(A) The number average molecular weight (Mn) of the polybenzoxazole precursor is preferably 5,000 to 100,000, more preferably 8,000 to 50,000. Here, the number average molecular weight is a numerical value measured by GPC and converted with standard polystyrene. The weight average molecular weight (Mw) of (A) the polybenzoxazole precursor is preferably 10,000 to 200,000, more preferably 16,000 to 100,000. Here, the mass average molecular weight is a numerical value measured by GPC and converted with standard polystyrene. Mw/Mn is preferably 1-5, more preferably 1-3.

(A) A polybenzoxazole precursor may be used individually by 1 type, and may be used in combination of 2 or more type. (A) The content of the polybenzoxazole precursor is preferably 30 to 95% by mass, more preferably 50 to 90% by mass, based on the total solid content of the composition.

In addition, composition solid content means the component which comprises a composition other than a solvent (especially organic solvent), or its mass and volume.

1-2. (B) Photosensitizer The photosensitive resin composition of the present invention contains a photosensitizer.
The photosensitizer (B) of the present invention includes naphthoquinonediazide compounds, diarylsulfonium salts, triarylsulfonium salts, dialkylphenacylsulfonium salts, diaryliodonium salts, aryldiazonium salts, aromatic tetracarboxylic acid esters, and aromatic sulfonic acid esters. , nitrobenzyl esters, aromatic N-oxyimide sulfonates, aromatic sulfamides, benzoquinone diazosulfonic acid esters, and the like. Among these, naphthoquinone diazide compounds are preferred.

Specific examples of the naphthoquinonediazide compound include tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene naphthoquinonediazide adducts (for example, TS533, TS567, TS583, TS593 manufactured by Sambo Kagaku Kenkyusho Co., Ltd.). ), naphthoquinone diazide adducts of tetrahydroxybenzophenone (for example, BS550, BS570, BS599, manufactured by Sambo Kagaku Kenkyusho Co., Ltd.), and 4-{4-[1,1-bis(4-hydroxyphenyl)ethyl]- Naphthoquinonediazide adducts of α,α-dimethylbenzyl}phenol (eg, TKF-428 and TKF-528 manufactured by Sambo Kagaku Kenkyusho Co., Ltd.) and the like can be used.
Here, the addition of naphthoquinonediazide may be achieved, for example, by reacting o-quinonediazide sulfonyl chlorides with a hydroxy compound or an amino compound.

(B) The photosensitive agent may be used alone or in combination of two or more. (B) The blending amount of the photosensitive agent is preferably 3 to 20% by mass based on the total solid content of the composition.

1-3. (C) Compound Having Two Allyl Groups in Molecule The photosensitive resin composition of the present invention contains (C) a compound having two allyl groups in the molecule.
The (C) compound containing two allyl groups in the molecule is not particularly limited, but examples include diallyl phthalate, diallyl isophthalate, diallyl terephthalate, 2,2′-diallylbisphenol A, trimethylolpropane diallyl ether, diallyl isocyanurate, diallyl propyl isocyanurate, pentaerythritol diallyl ether, and the like. Then, the compound (C) containing two allyl groups in the molecule becomes a linear polymer by self-reaction at a low temperature of 220° C. or less. Forms an interpenetrating polymer network with the precursor. As a result, the photosensitive resin composition of the present invention can be cured at a low temperature of 220° C. or less, and the cyclization reaction of the polybenzoxazole precursor is hardly hindered.
In addition, among the above (C) compounds containing two allyl groups in the molecule, compounds having an isocyanuric ring as a molecular structure have excellent reactivity and small polarization in the molecule, resulting in a low dielectric constant. , is preferred because it provides a cured product with excellent chemical resistance and toughness. Specifically, examples of compounds having an isocyanuric ring as a molecular structure include diallyl isocyanurate and diallyl propyl isocyanurate.

These (C) compounds having two allyl groups in the molecule may be used singly or in combination of two or more. The amount of the compound (C) having two allyl groups in the molecule to be added is preferably 0.5 to 30% by mass, more preferably 3 to 20% by mass, based on the total solid content of the composition. With such a blending ratio, as described above, it is possible to cure the photosensitive resin composition at a low temperature of 220 ° C. or less. It becomes possible to prepare a photosensitive resin composition. In addition, the photosensitive resin composition may contain a compound having one allyl group in the molecule within a range that does not impair the effects of the present invention.

1-4. Other Components The photosensitive resin composition of the present invention may further contain other components. Other components include, for example, solvents, cross-linking agents, thermal acid generators, silane coupling agents, sensitizers, adhesion aids, surfactants, leveling agents, plasticizers, fine particles, and adhesion agents. can.

(A) a polybenzoxazole precursor, (B) a photosensitizer, (C) a compound having two allyl groups in its molecule, and at least one of the compounds, and any other additive that dissolves the solvent. If so, it is not particularly limited. Specific examples of solvents include N,N'-dimethylformamide, N-methylpyrrolidone, N-ethyl-2-pyrrolidone, N,N'-dimethylacetamide, diethylene glycol dimethyl ether, cyclopentanone, γ-butyrolactone, α-acetyl -γ-butyrolactone, tetramethylurea, 1,3-dimethyl-2-imidazolinone, N-cyclohexyl-2-pyrrolidone, dimethylsulfoxide, hexamethylphosphoramide, pyridine, diethylene glycol monomethyl ether. These may be used alone or in combination of two or more. The amount of the solvent used can be in the range of 50 to 9000 parts by mass with respect to 100 parts by mass of the (A) polybenzoxazole precursor, depending on the coating film thickness and viscosity.

In addition, the photosensitive resin composition of the present invention can improve physical properties and adhesion of the film by adding a crosslinking agent, a thermal acid generator, and a silane coupling agent. As the cross-linking agent, the thermal acid generator, and the silane coupling agent, known ones can be appropriately selected and used, and are not particularly limited.

Furthermore, the photosensitive resin composition of the present invention may contain a known sensitizer for improving photosensitivity and a known adhesion promoter for improving adhesion to a substrate, within a range that does not impair the effects of the present invention. Agents and the like can also be blended.

Furthermore, various organic or inorganic low-molecular-weight or high-molecular-weight compounds may be added to the photosensitive resin composition of the present invention in order to impart processing properties and various functionalities. For example, surfactants, leveling agents, plasticizers, fine particles and the like can be used. Fine particles include organic fine particles such as polystyrene and polytetrafluoroethylene, and inorganic fine particles such as colloidal silica, carbon, and layered silicate. Further, the photosensitive resin composition of the present invention may contain various coloring agents, fibers, and the like.

The photosensitive resin composition of the present invention may be of a positive type or a negative type, but the positive type is preferable because more remarkable effects can be obtained.

[Dry film]
The dry film of the present invention has a resin layer obtained by drying after applying the photosensitive resin composition of the present invention. The dry film of the present invention is used by laminating a resin layer so as to be in contact with a substrate.

The dry film of the present invention is prepared by uniformly applying the photosensitive resin composition of the present invention to a carrier film (support film) by an appropriate method such as a blade coater, a lip coater, a comma coater, a film coater, and drying. It can be produced by forming a coated resin layer and preferably laminating a cover film (protective film) thereon. The cover film and the carrier film may be made of the same film material or different films.

In the dry film of the present invention, the film materials of the carrier film and the cover film can be any known materials used for dry films.

As the carrier film, for example, a thermoplastic film such as a polyester film such as polyethylene terephthalate having a thickness of 2 to 150 μm is used.

As the cover film, a polyethylene film, a polypropylene film, or the like can be used.

The film thickness of the resin layer on the dry film of the present invention is preferably 100 μm or less, more preferably in the range of 5 to 50 μm.

2. Method for Producing Cured Product of Photosensitive Resin Composition Using the photosensitive resin composition of the present invention, a pattern film, which is a cured product thereof, is produced as follows, for example, in the case of a positive photosensitive resin composition. .

First, in step 1, a coating film is obtained by applying a photosensitive resin composition onto a substrate and drying it, or by transferring (laminating) a resin layer from a dry film onto the substrate. The method for applying the photosensitive resin composition onto the substrate includes methods conventionally used for applying photosensitive resin compositions, such as spin coaters, bar coaters, blade coaters, curtain coaters, screen printers, and the like. a method of applying with a spray coater, a method of spraying with a spray coater, an inkjet method, or the like.

As a method for drying the coating film, methods such as air drying, heat drying using an oven or a hot plate, and vacuum drying are used. Moreover, it is desirable to dry the coating film under conditions that do not cause ring closure of the (A) polybenzoxazole precursor in the photosensitive resin composition. Specifically, natural drying, air drying, or heat drying can be performed at 70 to 140° C. for 1 to 30 minutes. Drying is preferably carried out on a hot plate for 1-20 minutes. Vacuum drying is also possible, and in this case, it can be carried out at room temperature for 20 minutes to 1 hour.

The substrate is not particularly limited, and can be widely applied to semiconductor substrates such as silicon wafers, wiring substrates, and substrates made of various resins, metals, and the like.

Next, as step 2, the coating film is exposed through a photomask having a pattern or directly. The exposure light used has a wavelength capable of activating the (B) photosensitive agent. Specifically, the exposure light preferably has a maximum wavelength in the range of 350 to 410 nm. As described above, photosensitivity can be adjusted by using a suitable sensitizer. As an exposure device, a contact aligner, mirror projection, stepper, laser direct exposure device, or the like can be used.

Subsequently, as step 3, heating may be performed to partially ring-close the unexposed portion of the polybenzoxazole precursor (A). Here, the ring closure rate is about 30%. The heating time and heating temperature are appropriately changed according to (A) the polybenzoxazole precursor, the coating film thickness, and (B) the type of photosensitive agent.

Then, as step 4, the coating film is treated with a developer. As a result, the exposed portions in the coating film can be removed to form a pattern film of the photosensitive resin composition of the present invention.

As a method used for development, any method can be selected from conventionally known photoresist development methods, such as a rotary spray method, a paddle method, an immersion method accompanied by ultrasonic treatment, and the like. Examples of the developer include inorganic alkalis such as sodium hydroxide, sodium carbonate, sodium silicate and aqueous ammonia; organic amines such as ethylamine, diethylamine, triethylamine and triethanolamine; tetramethylammonium hydroxide and tetrabutylammonium hydroxide. and aqueous solutions of quaternary ammonium salts such as If necessary, a suitable amount of a water-soluble organic solvent such as methanol, ethanol or isopropyl alcohol or a surfactant may be added. After that, the coating film is washed with a rinsing liquid as necessary to obtain a pattern film. Distilled water, methanol, ethanol, isopropyl alcohol, or the like can be used alone or in combination as the rinsing liquid. Moreover, you may use the said solvent as a developer.

Thereafter, in step 5, the pattern film is heated to obtain a cured coating film (cured product). At this time, (A) the polybenzoxazole precursor is ring-closed to obtain polybenzoxazole. The heating temperature is appropriately set so that the polybenzoxazole pattern film can be cured. For example, heating is performed at 150 to 350° C. for about 5 to 120 minutes in an inert gas. A more preferable range of heating temperature is 200 to 300°C. Heating is performed by using, for example, a hot plate, an oven, or a temperature-programmable oven. As the atmosphere (gas) at this time, air may be used, or an inert gas such as nitrogen or argon may be used.

In the case where the photosensitive resin composition of the present invention is a negative photosensitive resin composition, a photopolymerization initiator or a photobase generator is used as the (B) photosensitive agent, and the coating film is developed with a developer in step 4 above. By treating with, the unexposed portions in the coating film can be removed to form a pattern film of the photosensitive resin composition of the present invention.
In particular, even if the cured coating film of the photosensitive resin composition of the present invention is cured at a temperature of about 220°C, it has characteristics comparable to those of a cured coating film cured at a temperature of about 320°C. It can be suitably used for the fan-out wafer level package method.

3. Use of the photosensitive resin composition The use of the photosensitive resin composition of the present invention is not particularly limited. It is preferably used as a material forming material. Specifically, as a material for forming a display device, it can be used as a layer forming material or an image forming material for a color filter, a flexible display film, an insulating film, an alignment film, or the like. In addition, as a material for forming a semiconductor element, it can be used as a layer forming material such as an insulating film and a buffer coat film. Furthermore, as a material for forming electronic parts, it can be used as a sealing material or a layer forming material for a printed wiring board, an interlayer insulating film, a wiring coating film, and the like. Furthermore, as a material for forming optical parts, it can be used as an optical material or a layer forming material for holograms, optical waveguides, optical circuits, optical circuit parts, antireflection films, and the like. Furthermore, as building materials, it can be used for paints, coating agents, and the like.

The photosensitive resin composition of the present invention is mainly used as a pattern forming material, and the pattern film formed by it functions as a component that imparts heat resistance and insulation as a permanent film made of, for example, polybenzoxazole. Therefore, in particular, surface protective films for semiconductor devices, display devices and light emitting devices, interlayer insulating films, insulating films for rewiring, protective films for flip chip devices, protective films for devices having a bump structure, interlayer insulating films for multilayer circuits, It can be suitably used as an insulating material for passive components, protective films for printed wiring boards such as solder resists and coverlay films, liquid crystal alignment films, and the like.

Furthermore, as a material for forming electronic parts, it can be used as a sealing material or a layer forming material for a printed wiring board, an interlayer insulating film, a wiring coating film, and the like.

Furthermore, as a material for forming optical parts, it can be used as an optical material or a layer forming material for holograms, optical waveguides, optical circuits, optical circuit parts, antireflection films, and the like.

Furthermore, as building materials, it can be used for paints, coating agents, and the like.

EXAMPLES The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples. In the following description, "parts" and "%" are based on mass unless otherwise specified.

(Synthesis of polybenzoxazole precursor A-1)
In a 0.5 liter flask equipped with a stirrer and thermometer, 10.0 g (27.3 mmol) of bis(3-amino-4-hydroxyphenyl)hexafluoropropane was dissolved in 1500 g of N-methylpyrrolidone with stirring. . After that, the flask was immersed in an ice bath, and 8.78 g (29.8 mmol) of 4,4'-diphenyletherdicarboxylic acid chloride was added as a solid over 10 minutes while maintaining the inside of the flask at 0 to 5°C. for 30 minutes. Stirring was then continued at room temperature for 18 hours. The stirred solution was put into 700 mL of ion-exchanged water (specific resistance: 18.2 MΩ·cm), and the precipitate was recovered. After that, the obtained solid was dissolved in 420 mL of acetone and put into 1 L of deionized water. After collecting the precipitated solid, it was dried under reduced pressure to obtain a carboxyl group-terminated polybenzoxazole precursor of formula (2). The weight average molecular weight determined by GPC standard polystyrene conversion was 29,500, the number average molecular weight was 11,600, and the PDI was 2.54.
(Formula 2)
A-1

分子中に２つのアリル基を有する化合物
Ｃ－１：ジアリルフタレート
Ｃ－２：ジアリルイソフタレート
Ｃ－３：ジアリルテレフタレート
Ｃ－４：ジアリルイソシアヌレート ＬＡＤＩＣ（四国化成製）
Ｃ－５：ジアリルプロピルイソシアヌレート
Ｃ－６：トリアリルイソシアヌレート

密着剤
Ｄ－１：ＫＢＭ－５７３（信越化学社製）
可塑剤
Ｅ－１：ポリエステルアクリレート アロニックスＭ６２５０（東亞合成社製）
Ｅ－２：エポキシ樹脂 ＥＸＡ４８５０－１５０（ＤＩＣ社製） (Preparation of resin compositions of Reference Examples 1 to 3, Examples 4 to 9 and Comparative Examples 1 to 3)
Based on the composition of Table 1, each raw material was blended, dissolved in 300 parts of γ-butyrolactone, and filtered through a 0.2 μm filter to obtain a varnish of a photosensitive resin composition.
Raw material polybenzoxazole precursor A-1: Polybenzoxazole precursor obtained by the above synthesis Photosensitizer B-1: TKF-428 (manufactured by Sambo Kagaku Co., Ltd., naphthoquinone diazide compound)

Compound having two allyl groups in the molecule C-1: diallyl phthalate C-2: diallyl isophthalate C-3: diallyl terephthalate C-4: diallyl isocyanurate LADIC (manufactured by Shikoku Kasei)
C-5: diallyl propyl isocyanurate C-6: triallyl isocyanurate

Adhesion agent D-1: KBM-573 (manufactured by Shin-Etsu Chemical Co., Ltd.)
Plasticizer E-1: Polyester acrylate Aronix M6250 (manufactured by Toagosei Co., Ltd.)
E-2: Epoxy resin EXA4850-150 (manufactured by DIC)

<Chemical resistance evaluation>
The obtained varnishes of Reference Examples 1 to 3, Examples 4 to 9 , and Comparative Examples 1 to 3 were each coated on a silicon wafer (φ6 inch) using a spin coater, and heated on a hot plate at 110° C. for 3 minutes. After drying, a coating film having a thickness of about 8 μm was obtained. Thereafter, the coating film was heated in an inert gas oven at 150° C. under a nitrogen atmosphere for 30 minutes, and then heated at 4° C./min. and heated at 220° C. for 60 minutes to obtain a cured film. The obtained sample was immersed in propylene glycol monomethyl ether acetate (PGMEA), γ-butyrolactone (GBL), and ethyl butyrate for 10 minutes. Those that did not were marked with x. Table 1 shows the results.

<Permittivity and dielectric loss tangent measurement>
The obtained varnishes of Reference Examples 1 to 3, Examples 4 to 9 , and Comparative Examples 1 to 3 were each coated on a silicon wafer (φ6 inch) using a spin coater, and heated on a hot plate at 110° C. for 3 minutes. After drying, a coating film having a thickness of about 8 μm was obtained. Thereafter, the coating film was heated in an inert gas oven at 150° C. under a nitrogen atmosphere for 30 minutes, and then heated at 4° C./min. and heated at 220° C. for 60 minutes to obtain a cured film. Next, using a pressure cooker test (PCT) device, the cured film was peeled off under the conditions of 121° C., 100% RH, and 60 minutes, and then the dielectric constant and dielectric loss tangent were measured. The dielectric constant and dielectric loss tangent were evaluated by measuring the dielectric constant and dielectric loss tangent at 10 GHz using an RF impedance/material analyzer (manufactured by Agilent Technologies, Agilent E4991A). The evaluation criteria are as follows. Table 1 shows the results.
Evaluation of dielectric constant ◎: less than 3.0,
○: 3.0 or more and less than 3.5,
×: 3.5 or more Evaluation of dielectric loss tangent ◎: less than 0.01,
○: 0.01 or more and less than 0.015,
x: 0.015 or more When a self-supporting film was not obtained, it was indicated as "-".

<Evaluation of elongation at break (toughness evaluation)>
The obtained varnishes of Reference Examples 1 to 3, Examples 4 to 9 , and Comparative Examples 1 to 3 were each coated on a silicon wafer (φ6 inch) using a spin coater, and heated on a hot plate at 110° C. for 3 minutes. After drying, a coating film having a thickness of about 8 μm was obtained. Thereafter, the coating film was heated in an inert gas oven at 150° C. under a nitrogen atmosphere for 30 minutes, and then heated at 4° C./min. and heated at 220° C. for 60 minutes to obtain a cured film. Next, using a pressure cooker test (PCT) device, the cured film was peeled off under the conditions of 121° C., 100% RH, and 60 minutes, and then the elongation at break was measured. The elongation at break was obtained from a tensile test using EZ-SX manufactured by Shimadzu Corporation. Evaluation was performed according to the following evaluation criteria. Moreover, evaluation was performed according to the following criteria. Table 1 shows the results.
◎: 10% or more ○: less than 10%, 2% or more ×: self-supporting film could not be obtained

From the above results, the effects of the present invention can be understood.

Claims (4)

(A) a polybenzoxazole precursor, (B) a photosensitizer, (C) a compound containing two allyl groups in the molecule ,
The above-mentioned compound is a photosensitive resin composition in which the compound self-reacts to form a linear polymer at a temperature of 220° C. or less and has an isocyanuric ring as a molecular structure. A dry film comprising a resin layer obtained by applying the photosensitive resin composition according to claim 1 to a film and drying the film. A cured product obtained by curing the photosensitive resin composition according to claim 1 or the resin layer of the dry film according to claim 2. An electronic component comprising the cured product according to claim 3 .