JP2024016751A - Polyketone compound, photosensitive resin composition, dry film, cured product and electronic component - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polyketone compound which has more excellent heat resistance and mechanical strength, and has excellent resolution when being used as a photosensitive material.

SOLUTION: There is provided a polyketone compound. The polyketone compound includes a repeating unit of the following formula (1) (wherein, X and Y are single bonds, oxygen atoms or divalent organic groups).

SELECTED DRAWING: None

COPYRIGHT: (C)2024,JPO&INPIT

Description

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

In recent years, with the demand for higher functionality and miniaturization of semiconductor devices, it has become necessary to form cured films with finer patterns (resolution ) is required. Since these insulating films and cured films are used as permanent films, they are also required to have excellent properties such as insulating properties, high heat resistance, and mechanical strength. However, there are still a limited number of photosensitive materials that can achieve both resolution, insulation, heat resistance, mechanical strength, etc., and there is an increasing demand for new photosensitive materials.

Generally, aromatic polyketones have excellent heat resistance and mechanical properties, and are used as engineering plastics. Patent Document 1 discloses that an aromatic polyketone having a specific structure can form a cured product having not only excellent heat decomposition resistance and high transparency but also high Tg and excellent toughness.

Japanese Patent Application Publication No. 2018-168270

Although it is disclosed that the aromatic polyketone of Patent Document 1 has excellent heat resistance and mechanical properties, no evaluation has been made regarding the possibility of patterning or resolution when used as a photosensitive material. It has not been. Furthermore, the polyketone synthesized in the example of Patent Document 1 does not contain the hydroxyl group necessary for making a photosensitive material by adding a photoacid generator, etc. Nothing is disclosed about the effects. For this reason, the polyketone disclosed in Patent Document 1 has poor resolution and may not be patternable.

Therefore, an object of the present disclosure is to provide a polyketone compound that has excellent resolution when used as a photosensitive material.

（Ｘ、Ｙは、互いに独立に、単結合、酸素原子又は２価の有機基である。）
前記Ｘは、単結合であることが好ましい。
前記Ｙは、炭素数が２０以下の、芳香環を含む２価の有機基であることが好ましい。
本開示技術の別の一態様によれば、ポリケトン化合物と、光酸発生剤とを含む感光性樹脂組成物を提供することができる。
本開示技術の別の一態様によれば、前記感光性樹脂組成物により形成された樹脂層を備えることを特徴とする、ドライフィルムを提供することができる。
本開示技術の別の一態様によれば、前記感光性樹脂組成物又は前記ドライフィルムの樹脂層により形成されることを特徴とする、硬化物を提供することができる。
本開示技術の別の一態様によれば、前記硬化物を有することを特徴とする、電子部品を提供することができる。 The present inventors have discovered that the above-mentioned problems can be solved when a polyketone compound having a specific structure is used as a photosensitive material, and has completed the present invention.
That is, according to one aspect of the disclosed technology,
A polyketone compound characterized by containing a repeating structure of the following formula (1) can be provided.

(X and Y are each independently a single bond, an oxygen atom, or a divalent organic group.)
The X is preferably a single bond.
The Y is preferably a divalent organic group containing an aromatic ring and having 20 or less carbon atoms.
According to another aspect of the disclosed technology, a photosensitive resin composition containing a polyketone compound and a photoacid generator can be provided.
According to another aspect of the presently disclosed technology, it is possible to provide a dry film characterized by including a resin layer formed from the photosensitive resin composition.
According to another aspect of the technology of the present disclosure, it is possible to provide a cured product characterized by being formed of the photosensitive resin composition or the resin layer of the dry film.
According to another aspect of the disclosed technology, it is possible to provide an electronic component that includes the cured product.

According to the disclosed technology, it is possible to provide a polyketone compound that has excellent resolution when used as a photosensitive material.

1 is a ¹ H-NMR spectrum of the polyketone compound of Example 1. 1 is a ¹ H-NMR spectrum of the polyketone compound of Example 2. 1 is a ¹ H-NMR spectrum of the polyketone compound of Comparative Example 1. ¹ H-NMR spectrum of the polyketone compound of Comparative Example 2.

Hereinafter, embodiments of the disclosed technology will be described in detail. In addition, in this specification, the notation "a to b" in the description of numerical ranges represents a range from a to b, unless otherwise specified.

（Ｘ、Ｙは、単結合、酸素原子又は２価の有機基である） <<Polyketone compound>>
The polyketone compound of the present disclosure includes a repeating structure of the following formula (1), preferably a repeating structure of the following formula (1)'.

(X and Y are a single bond, an oxygen atom, or a divalent organic group)

（Ｘ、Ｙは、単結合、酸素原子又は２価の有機基である）

(X and Y are a single bond, an oxygen atom, or a divalent organic group)

X is a single bond, an oxygen atom, or a divalent organic group. The divalent organic group is not particularly limited, and can be linear, branched, or cyclic. The divalent organic group is preferably a hydrocarbon group or a divalent organic group containing an ether bond. Further, the divalent organic group may be unsubstituted, or may be substituted with a halogen atom such as fluorine, chlorine, bromine, or iodine. Further, X is preferably a single bond, an oxygen atom, or a divalent organic group having 10 or less carbon atoms, more preferably a single bond, an oxygen atom, or a divalent organic group having 5 or less carbon atoms, and even more preferably a single bond. When X has such a structure, it is possible to obtain a polyketone compound that has superior heat resistance and mechanical strength, and has excellent resolution when used as a photosensitive material.

Y is a single bond, an oxygen atom, or a divalent organic group, and the divalent organic group is not particularly limited and can be linear, branched, or cyclic. The divalent organic group may be unsubstituted, or may be substituted with a halogen atom such as fluorine, chlorine, bromine, or iodine. Further, Y is preferably a single bond, an oxygen atom, or a divalent organic group having 20 or less carbon atoms, and more preferably a divalent organic group containing an aromatic ring and having 20 or less carbon atoms. When Y has such a structure, it is possible to obtain a polyketone compound that has superior heat resistance and mechanical strength, and has excellent resolution when used as a photosensitive material.

As an example of a polyketone compound, a polyketone compound having a repeating structure of the following formula (2) or the following formula (3) has better heat resistance and mechanical strength, and when used as a photosensitive material, has an excellent It is preferably used because it has good resolution.

The weight average molecular weight (Mw) of the polyketone compound can be freely selected depending on the application, but for example, when used in a photosensitive material, the Mw can be set to 2,000 to 50,000.
The number average molecular weight (Mn) of the polyketone compound can also be freely selected depending on the application, but for example, when used in a photosensitive material, Mn can be set to 1,000 to 30,000.
The molecular weight dispersity (PDI) of the polyketone compound can be freely selected depending on the application, and for example, when used in a photosensitive material, it can be set to 1.5 to 4.0.
In this specification, the weight average molecular weight and number average molecular weight are values measured by gel permeation chromatography (GPC) and converted to standard polystyrene.
Moreover, in this specification, molecular weight dispersity (PDI) is calculated by the following formula (4).
PDI=Mw/Mn...(4)

<<Production method of polyketone compound>>
The method for producing a polyketone compound of the present disclosure is not particularly limited, but for example, an aromatic monomer having a structure of the following formula (5) and a dicarboxylic acid having a structure of the following formula (6) are condensed in an acidic solvent. Examples include methods using reactions.

Examples of dicarboxylic acids having a divalent organic group containing an aromatic ring and having 20 or less carbon atoms include phthalic acid, isophthalic acid, terephthalic acid, 4,6-dimethylisophthalic acid, 4,4'-biphenyldicarboxylic acid, and benzophenone. 4,4'-dicarboxylic acid, 1,4-naphthalene dicarboxylic acid, 4,4'-stilbenedicarboxylic acid, 4-(carboxymethyl)benzoic acid, 4-methylphthalic acid, 4,4'-dicarboxydiphenyl ether, ethylene glycol Examples include bis(4-carboxyphenyl) ether and 1,6-bis(4-carboxyphenoxy)hexane. These can be used alone or in combination in any ratio. Among these, terephthalic acid and 4,4'-dicarboxydiphenyl ether are preferably used.

As the acidic solvent, a solution of aluminum chloride in an organic solvent, trifluoroalkanesulfonic acid, polyphosphoric acid, and a mixture of diphosphorus pentoxide and an organic sulfonic acid can be used. Among these, trifluoroalkanesulfonic acid is preferred, and trifluoromethanesulfonic acid is more preferably used.

The amount of the acidic solvent is not particularly limited as long as it can dissolve the aromatic monomer of the above formula (5) and the dicarboxylic acid of the above formula (6). For example, the amount of the dicarboxylic acid of the above formula (6) is 1 mass. 5 to 100 parts by mass.

The polyketone compound is prepared by dissolving the aromatic monomer of the above formula (5) and the dicarboxylic acid of the above formula (6) in an acidic solvent in a reaction vessel, and heating the mixture for 10 to 10 minutes in an air atmosphere or an inert gas atmosphere such as nitrogen or argon. It can be produced by adjusting the temperature to 100°C and stirring for 1 to 72 hours. After the reaction is completed, a poor solvent (e.g., water) for the polyketone compound is poured into the reaction container, and a mixture containing the polyketone compound is precipitated, collected by filtration, etc., and dried (e.g., using a vacuum drying method in an environment of 25 ° C. (dry for about 3 hours). After dissolving the obtained mixture in a solvent (for example, N,N-dimethylacetamide) in a container, a poor solvent for the polyketone compound (for example, 2-propanol) is poured off, the polyketone compound is precipitated, and the polyketone compound is filtered. Collect. Thereafter, the polyketone compound can be obtained by drying (for example, drying for about 12 hours using a vacuum drying method in an environment of 80° C.).

<<Uses of polyketone compounds>>
The polyketone compound of the present disclosure can be blended with a photoacid generator and used as a photosensitive resin composition. The obtained photosensitive resin composition can be suitably used as a forming material for display devices, semiconductor elements, electronic components, optical components, building materials, and the like. Examples of materials for forming semiconductor elements include resist materials, buffer coat films, and insulating films. Furthermore, examples of materials for forming electronic components include printed wiring boards, interlayer insulating films, wiring coating films, and the like.

<Photosensitive resin composition>
A polyketone compound can be blended with a photoacid generator and used as a photosensitive resin composition.
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 rays or visible light, and examples thereof include naphthoquinone diazide compounds, diarylsulfonium salts, triarylsulfonium salts, dialkylphenacylsulfonium salts, Examples include diaryliodonium salts, aryldiazonium salts, aromatic tetracarboxylic acid esters, aromatic sulfonic acid esters, nitrobenzyl esters, aromatic N-oxyimidosulfonates, aromatic sulfamides, benzoquinonediazosulfonic acid esters, etc. . These can be used alone or in combination in any ratio. The photoacid generator is preferably a dissolution inhibitor, and preferably a naphthoquinone diazide compound.

Examples of naphthoquinone diazide compounds include naphthoquinone diazide adducts of tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (for example, TKF-520, TKF-528, TKF-420 manufactured by Sanpo Chemical Research Institute). , TKF-428), naphthoquinonediazide adducts of tetrahydroxybenzophenone (for example, BS550, BS570, BS599 manufactured by Sanpo Chemical Research Institute), etc. can be used. Here, addition of naphthoquinonediazide can be carried out by, for example, reacting o-quinonediazide sulfonyl chloride with a hydroxy compound or an amino compound. These can be used alone or in combination in any ratio.

The amount of the photoacid generator to be blended can be 3 to 20% by mass, when the total mass of the photosensitive resin composition is 100% by mass.

The photosensitive resin composition can be produced by dissolving a polyketone compound and a photoacid generator in a solvent and stirring the solution.

The solvent is not particularly limited, and examples include 2-methoxy-1-methylethyl acetate (PGMEA), cyclohexanone, γ-butyrolactone, ethyl lactate, butyl acetate, benzyl acetate, ethoxyethylpropionate, and 3-methylmethoxy. Propionate, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosphorylamide, tetramethylene sulfone, diethyl ketone, diisobutyl Ketones, methyl amyl ketone, propylene glycol monomethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, xylene, mesitylene, ethylbenzene, propylbenzene, cumene, diisopropylbenzene, hexylbenzene, anisole, diglyme, dimethyl Examples include sulfoxide, chloroform, dichloromethane, dichloroethane, and chlorobenzene. These can be used alone or in combination in any ratio.

The photosensitive resin composition can contain other components as long as they do not impair the effects of the disclosed technology. As other components, known components that can be included in the photosensitive resin composition can be used, such as crosslinking agents, adhesives, surfactants, plasticizers, thermal acid generators, sensitizers, and leveling agents. agents, colorants, fibers, fine particles, basic compounds, etc. Among them, it is desirable to use a compound having an epoxy group or methylol group that can react with a phenolic hydroxyl group as a crosslinking agent.

<Dry film>
A dry film can be formed by applying the photosensitive resin composition onto a base material to form a resin layer. Further, in order to protect the resin layer, a protective film may be further laminated on the surface of the resin layer.

Although the base material is not particularly limited, examples thereof include metal foil such as copper foil, films such as polyimide film, polyester film, and polyethylene naphthalate (PEN) film.

The protective film is not particularly limited, but polyethylene film, polytetrafluoroethylene film, polypropylene film, paper, etc. can be used. It is preferable to select a protective film in which the adhesive strength between the protective film and the resin layer is lower than the adhesive strength between the base material and the resin layer. In order to make the adhesion between the protective film and the resin layer lower than the adhesion between the base material and the resin layer, the surface of the protective film may be subjected to a release treatment.

The thickness of the resin layer is not particularly limited, but can be 1 to 150 μm depending on the application. For example, the resin layer is formed by applying a photosensitive resin composition onto a base material, using a comma coater, a blade coater, a lip coater, a rod coater, a squeeze coater, a reverse coater, a transfer roll coater, a gravure coater, a spray coater, etc. It can be obtained by adjusting the thickness of the resin layer and drying it.

<Cured product>
The cured product of the present disclosure is obtained by curing the resin layer of the photosensitive resin composition or dry film of the present disclosure. The cured product may be a patterned cured product. Examples of methods for producing a patterned cured product include the following method.

(Dry coating forming process)
The dry coating film forming step is a step in which the photosensitive resin composition of the present disclosure is applied onto a substrate to form a coating film, and then dried. In the dry coating film forming step, it is also possible to form a dry coating film on the substrate by transferring the resin layer of the dry film onto the substrate.

The method of applying the photosensitive resin composition onto the substrate is not particularly limited, and examples thereof include applying using a spin coater, bar coater, blade coater, curtain coater, screen printer, etc., and spraying using a spray coater. method, inkjet method, etc.

The method of drying the coating film is not particularly limited, and examples thereof include air drying, heating drying using an oven or hot plate, vacuum drying, and the like. The conditions for heat drying are, for example, a heating temperature of 70 to 140°C and a drying time of 1 to 30 minutes.

Transfer of the resin layer of the dry film onto the base material is preferably performed under pressure and heat using a vacuum laminator or the like. The heating temperature can be, for example, 60 to 100°C.

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

(Exposure process)
In the exposure process, the dry coating film formed in the dry coating film formation process is irradiated with radiation through a photomask that allows the formation of the desired pattern, thereby exposing the photoacid generator in the exposed area to light and making it active. This is the process of generating seeds. If patterning is not required, there is no need to use a photomask. Alternatively, a pattern may be drawn directly with a laser using a direct drawing device.

The wavelength of the radiation used is one that can activate the photoacid generator, and in order to perform fine patterning, the maximum wavelength is preferably 410 nm or less. The irradiation energy can be adjusted depending on the thickness of the dried coating film formed, the absorption wavelength of the photoacid generator, etc., and can be, for example, 10 to 1000 mJ/cm ² . 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.

(Development process)
The developing step is a step in which a patterned coating film is obtained by treating the exposed dry coating film with a developer and dissolving and removing the exposed area in the developer. As a developing method, a known method can be used, such as a rotary spray method, a paddle method, an immersion method accompanied by ultrasonic treatment, and the like.

As the developer, known developers can be used, such as inorganic alkalis such as sodium hydroxide, sodium carbonate, sodium silicate, and aqueous ammonia, organic amines such as ethylamine, diethylamine, triethylamine, and triethanolamine, and tetrahydroxide. Examples include aqueous solutions of quaternary ammonium salts such as methylammonium hydroxide and tetrabutylammonium hydroxide. If necessary, a water-soluble organic solvent such as methanol, ethanol, isopropyl alcohol, or a surfactant can be added.

After the treatment with the developer, the coating film can be washed with a rinsing solution if necessary to obtain a patterned coating film. The rinsing liquid 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 in any ratio.

(Post-development heating step)
The post-development heating step is a step in which the patterned coating film formed in the development step is heated to complete the curing of the patterned coating film and obtain a cured patterned coating film (cured product), and the composition components include a crosslinking agent. When a compound having an epoxy group or a methylol group is used, the thermal properties, mechanical properties, etc. of the cured product can be improved by crosslinking with the phenolic hydroxyl group of the polyketone. The heating temperature can be 150 to 200°C, and the heating time can be 1 to 120 minutes. Heating can be performed using a known method such as a hot plate or an inert oven, and heating is preferably performed under a nitrogen atmosphere.

The present invention will be explained in more detail using examples, but the present invention is not limited to the examples.

A polyketone compound was produced as follows.

<Synthesis Example 1: Polyketone compound of Example 1>
Dissolve 4,4'-dicarboxydiphenyl ether (ODBA; 0.078 g, 0.30 mmol) and 2,2'-dihydroxybiphenyl (DHBP; 0.077 g, 0.36 mmol) in trifluoromethanesulfonic acid (0.45 ml). The mixture was stirred at 40°C for 24 hours. The mixture was poured into water and the resulting precipitate was collected by filtration. After vacuum drying for 3 hours at 25° C., the obtained polymer was dissolved in N,N-dimethylacetamide (DMAc). The mixture was poured into 2-propanol, and the resulting precipitate was collected by filtration. The polyketone compound of Example 1 was obtained by vacuum drying at 80° C. for 12 hours.
The structure of the polyketone compound of Example 1 was confirmed by ¹ H-NMR analysis. The spectrum of the measured ¹ H-NMR analysis is shown in FIG.
The polyketone compound of Example 1 had a weight average molecular weight (Mw) of 30,600, a number average molecular weight (Mn) of 13,300, and a molecular weight dispersity (PDI) of 2.3.

Below is the structural formula of the polyketone compound of Example 1.

Below is the structural formula of 4,4'-dicarboxydiphenyl ether (ODBA).

Below is the structural formula of 2,2'-dihydroxybiphenyl (DHBP).

<Synthesis Example 2: Polyketone compound of Example 2>
Terephthalic acid (TP; 0.050 g, 0.30 mmol) and 2,2'-dihydroxybiphenyl (DHBP; 0.077 g, 0.36 mmol) were dissolved in trifluoromethanesulfonic acid (0.45 ml), and the mixture was heated at 40°C for 24 hours. Stir for hours. The mixture was poured into water and the resulting precipitate was collected by filtration. After vacuum drying for 3 hours at 25° C., the obtained polymer was dissolved in N,N-dimethylacetamide (DMAc). The mixture was poured into 2-propanol, and the resulting precipitate was collected by filtration. The polyketone compound of Example 2 was obtained by vacuum drying at 80° C. for 12 hours.
The structure of the polyketone compound of Example 2 was confirmed by ¹ H-NMR analysis. The spectrum of the measured ¹ H-NMR analysis is shown in FIG.
The polyketone compound had a weight average molecular weight (Mw) of 4,900, a number average molecular weight (Mn) of 1,810, and a molecular weight dispersity (PDI) of 2.7.

Below is the structural formula of the polyketone compound of Example 2.

Below is the structural formula of terephthalic acid (TP).

<Synthesis Example 3: Polyketone compound of Comparative Example 1>
Dissolve 4,4'-dicarboxydiphenyl ether (ODBA; 0.078 g, 0.30 mmol) and 2,2'-dimethoxybiphenyl (DMB; 0.077 g, 0.36 mmol) in trifluoromethanesulfonic acid (0.45 ml). The mixture was stirred at 40°C for 24 hours. The mixture was poured into water and the resulting precipitate was collected by filtration. After vacuum drying for 3 hours at 25° C., the obtained polymer was dissolved in N,N-dimethylacetamide (DMAc). The mixture was poured into 2-propanol, and the resulting precipitate was collected by filtration. Vacuum drying was performed at 80° C. for 12 hours to obtain a polyketone compound of Comparative Example 1.
The structure of the polyketone compound of Comparative Example 1 was confirmed by ¹ H-NMR analysis. The spectrum of the measured ¹ H-NMR analysis is shown in FIG.
The polyketone compound of Comparative Example 1 had a weight average molecular weight (Mw) of 30,600, a number average molecular weight (Mn) of 13,300, and a molecular weight dispersity (PDI) of 2.3.

The following is the structural formula of the polyketone compound of Comparative Example 1.

Below is the structural formula of 2,2'-dimethoxybiphenyl (DMB).

<Synthesis Example 4: Polyketone compound of Comparative Example 2>
Terephthalic acid (TP; 0.050 g, 0.30 mmol) and 2,2'-dimethoxybiphenyl (DMB; 0.077 g, 0.36 mmol) were dissolved in trifluoromethanesulfonic acid (0.45 ml), and the mixture was heated at 40°C for 24 hours. Stir for hours. The mixture was poured into water and the resulting precipitate was collected by filtration. After vacuum drying for 3 hours at 25° C., the obtained polymer was dissolved in N,N-dimethylacetamide (DMAc). The mixture was poured into 2-propanol, and the resulting precipitate was collected by filtration. Vacuum drying was performed at 80° C. for 12 hours to obtain a polyketone compound of Comparative Example 2.
The structure of the polyketone compound of Comparative Example 2 was confirmed by ¹ H-NMR analysis. The spectrum of the measured ¹ H-NMR analysis is shown in FIG.
The polyketone compound of Comparative Example 2 had a weight average molecular weight (Mw) of 4,900, a number average molecular weight (Mn) of 1,810, and a molecular weight dispersity (PDI) of 2.7.

The following is the structural formula of the polyketone compound of Comparative Example 2.

<Preparation of photosensitive resin composition>
100 parts by mass of each of the obtained polyketone compounds of Examples and Comparative Examples and 20 parts by mass of a photoacid generator (TKF-428 manufactured by Sanpo Chemical Research Institute) were dissolved in a solvent, and the non-volatile components in the varnish were dissolved in the solvent. By dissolving and adjusting the concentration of 20% by mass, varnishes of photosensitive resin compositions of each example and comparative example were obtained. As a solvent, PGMEA was used for the polyketone of Example 1 and Comparative Example 1, and cyclohexanone was used for the polyketone compound of Example 2 and Comparative Example 2.

<Evaluation>
The following evaluations were performed using the obtained varnishes of each Example and Comparative Example.

(Resolution evaluation)
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 would be 3.0 μm, and dried using a hot plate at 110°C for 3 minutes. A dried coating film of the photosensitive resin composition of Comparative Example was obtained. This dried coating film was exposed to a test pattern with L/S of 2 μm/2 μm using a contact exposure device (light source: high-pressure mercury lamp). Thereafter, development was performed for 60 seconds using a 2.38% TMAH aqueous solution and rinsed with pure water to obtain samples having patterns of the photosensitive resin compositions of the respective Examples and Comparative Examples. In addition, the exposure conditions (exposure amount and focus) for the photosensitive resin compositions of each Example and Comparative Example were selected to provide the best resolution for each photosensitive resin composition of each Example and Comparative Example. I went.
The obtained samples of each example and comparative example were 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) to evaluate whether a 2 μm/2 μm (L/S) test pattern was normally formed.
As a result, the photosensitive resin compositions using the polyketone compounds of Examples 1 and 2 were able to normally form a pattern and showed excellent resolution, but the photosensitive resin compositions using the polyketone compounds of Comparative Examples 1 and 2 Pattern formation and resolution could not be obtained with resin compositions.

Claims (9)

A polyketone compound characterized by containing a repeating structure represented by the following formula (1).

(X and Y are each independently a single bond, an oxygen atom, or a divalent organic group) The polyketone compound according to claim 1, wherein the X is a single bond. 3. The polyketone compound according to claim 1, wherein Y is a divalent organic group containing an aromatic ring and having 20 or less carbon atoms. A photosensitive resin composition comprising the polyketone compound according to claim 1 or 2 and a photoacid generator. A dry film comprising a resin layer formed from the photosensitive resin composition according to claim 4. A cured product formed from the photosensitive resin composition according to claim 4. An electronic component comprising the cured product according to claim 6. A cured product formed from the resin layer of the dry film according to claim 5. An electronic component comprising the cured product according to claim 8.

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