JP7637089B2 - Photosensitive resin composition, photosensitive resin film, method for producing cured product, laminate, and electronic component - Google Patents

Description

The present disclosure relates to a photosensitive resin composition, a photosensitive resin film, a method for producing a cured product, a laminate, and an electronic component.

In the field of manufacturing semiconductor integrated circuits (LSIs) or wiring boards, photosensitive materials are used as resists for producing conductor patterns. For example, in the manufacture of wiring boards, a resist is formed using a photosensitive resin composition, and then a conductor pattern, metal posts, etc. are formed by plating. More specifically, a photosensitive layer is formed on a support (substrate) using a photosensitive resin composition, etc., and the photosensitive layer is exposed through a predetermined mask pattern, and then a development process is performed so that the parts where the conductor pattern, metal posts, etc. are to be formed can be selectively removed (peeled off), forming a resist pattern (resist). Next, a conductor such as copper is formed on the removed parts by plating, and then the resist pattern is removed, thereby manufacturing a wiring board equipped with a conductor pattern, metal posts, etc.

Conventionally, thick conductor patterns and metal posts have been produced by growing metal plating after removing the resist pattern. In order to meet such demands, for example, thick-film photosensitive resists with a photosensitive layer thickness of about 30 μm, or even 65 μm at most, have been used (see Patent Documents 1 and 2).
In recent years, in order to achieve even higher performance, attempts have been made to form a conductor layer as thick as about 150 μm by performing a plating process while destroying, with a plating solution, the layer of the metal ion dilute layer that exists in the direction of the desired selective plating growth (see Patent Document 3).

JP 2015-034926 A JP 2014-074774 A JP 2014-080674 A

However, with conventional thick-film photosensitive resists, when a thick photosensitive layer of, for example, 70 μm or more is required, light does not easily pass through to the bottom, and the pattern shape may deteriorate. In addition, with the method described in Patent Document 3, plating proceeds while partially destroying the thin metal ion layer, so it is difficult to stably form an excellent pattern. Therefore, there is a demand for a photosensitive resist that has excellent pattern forming properties even when a photosensitive layer of 70 μm or even 150 μm or more thicker than conventional ones is formed.

The problem that this disclosure aims to solve has been made in consideration of the above circumstances, and is to provide a photosensitive resin composition, a photosensitive resin film, a method for producing a cured product, a laminate, and an electronic component (hereinafter sometimes referred to as "photosensitive resin composition, etc.") that have excellent pattern forming properties even when a thick photosensitive layer of, for example, 70 μm or more is formed.

As a result of intensive research into solving the above problems, the present inventors have found that the problems can be solved by a photosensitive resin composition having the following configuration. The present disclosure provides the following photosensitive resin composition.

[1] A photosensitive resin composition comprising: component (A): a high molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; component (B): a low molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; and component (C): a photopolymerization initiator, wherein component (B) contains a low molecular weight material having an acryloyl group as the photopolymerizable functional group.
[2] A photosensitive resin film having a photosensitive layer using the photosensitive resin composition according to [1] above.
[3] A method for producing a cured product, comprising the steps of: providing a photosensitive layer on a substrate using the photosensitive resin composition according to [1] above or the photosensitive resin film according to [2] above; irradiating at least a portion of the photosensitive layer with active light to form a photocured portion; and removing at least a portion of the photosensitive layer other than the photocured portion to form a resin pattern.
[4] A laminate comprising a cured product of the photosensitive resin composition described in [1] above.
[5] An electronic component comprising a cured product of the photosensitive resin composition described in [1] above.

According to the present disclosure, it is possible to provide a photosensitive resin composition etc. that has excellent pattern forming properties even when forming a thick photosensitive layer, for example, 70 μm or more.

FIG. 2 is a schematic diagram showing an example of a resolution evaluation mask used in the examples.

The present disclosure will be described in detail below.
In this specification, a numerical range indicated using "to" indicates a range including the numerical values described before and after "to" as the minimum and maximum values, respectively, and the minimum and maximum values described in stages may be arbitrarily combined. In addition, in a numerical range described in stages in this specification, the upper limit or lower limit of a numerical range in a certain stage may be arbitrarily combined with the upper limit or lower limit of a numerical range in another stage. In addition, in a numerical range described in this specification, the upper limit or lower limit of the numerical range may be replaced with a value shown in an example.
The term "(meth)acrylic acid" means at least one of "acrylic acid" and its corresponding "methacrylic acid", and the same applies to other similar expressions such as (meth)acrylate.

[Photosensitive resin composition]
A photosensitive resin composition according to an embodiment of the present disclosure (hereinafter, may be simply referred to as the present embodiment) is a photosensitive resin composition containing: component (A): a high molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; component (B): a low molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; and component (C): a photopolymerization initiator, wherein the component (B) contains a low molecular weight material having an acryloyl group as the photopolymerizable functional group.
In this specification, the term "solid content" refers to the non-volatile content excluding volatile substances such as water and solvent contained in the photosensitive resin composition, and refers to the components that remain without volatilization when the resin composition is dried, and also includes those that are liquid, starch syrup-like, or wax-like at room temperature (25°C). Each component will be described below.

<(A) component: high molecular weight body>
The photosensitive resin composition of the present embodiment contains a polymer having a photopolymerizable functional group and a carbon-nitrogen bond as component (A). The term "polymer" refers to a compound having a weight-average molecular weight of 2,000 or more. In this specification, the weight-average molecular weight (Mw) is a value determined by gel permeation chromatography (GPC) using tetrahydrofuran (THF) and converted into standard polystyrene.
Examples of the photopolymerizable functional group possessed by the polymer of component (A) include (meth)acryloyl groups; and ethylenically unsaturated groups such as alkenyl groups, such as allyl groups and vinyl groups. From the viewpoint of improving pattern formability, component (A) may include a polymer having a (meth)acryloyl group as the photopolymerizable functional group, and may further include a polymer having a urethane bond as the carbon-nitrogen bond. Examples of polymers having a (meth)acryloyl group as the photopolymerizable functional group include (meth)acrylates, and examples of polymers having a urethane bond as the carbon-nitrogen bond include urethane (meth)acrylates.
Furthermore, the component (A) may contain a polymer having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton.

Component (A) has at least one of these photopolymerizable functional groups and at least one carbon-nitrogen bond. The total number of photopolymerizable functional groups (number of functional groups) contained in the polymer of component (A) may be appropriately selected from 2 to 15 in one molecule from the viewpoint of improving pattern formability and heat resistance, and from 2 to 12 or 2 to 10 from the viewpoint of stabilizing the physical properties and characteristics of the resulting cured product.

Examples of the urethane (meth)acrylate of the component (A) include a reaction product of a (meth)acrylate having a hydroxyl group and an isocyanate compound having an isocyanate group.
Examples of the (meth)acrylate having a hydroxyl group include compounds having at least one hydroxyl group and at least one (meth)acryloyl group in one molecule. More specifically, examples of the (meth)acrylate having a hydroxyl group include monofunctional (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-hydroxy-3-(o-phenylphenoxy)propyl (meth)acrylate, 2-hydroxy-3-(1-naphthoxy)propyl (meth)acrylate, and 2-hydroxy-3-(2-naphthoxy)propyl (meth)acrylate, as well as ethoxylated products thereof, propoxylated products thereof, and ethoxylated propoxylated products thereof. difunctional (meth)acrylates such as trimethylolpropane di(meth)acrylate, glycerin di(meth)acrylate, bis(2-(meth)acryloyloxyethyl)(2-hydroxyethyl)isocyanurate, ethoxylated products thereof, propoxylated products thereof, ethoxylated propoxylated products thereof, and caprolactone-modified products thereof; cyclohexane dimethanol type epoxy di(meth)acrylate, tricyclodecane dimethanol type epoxy di(meth)acrylate, hydrogenated bisphenol A type epoxy di(meth)acrylate, hydrogenated bisphenol F type epoxy di(meth)acrylate, hydroquinone bifunctional epoxy (meth)acrylates such as aryl epoxy di(meth)acrylate, resorcinol epoxy di(meth)acrylate, catechol epoxy di(meth)acrylate, bisphenol A epoxy di(meth)acrylate, bisphenol F epoxy di(meth)acrylate, bisphenol AF epoxy di(meth)acrylate, biphenol epoxy di(meth)acrylate, fluorene bisphenol epoxy di(meth)acrylate, and monoallyl isocyanurate epoxy di(meth)acrylate; ditrimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipenta ... Examples of such epoxy (meth)acrylates include tri- or higher functional (meth)acrylates such as rhythritol tetra(meth)acrylate and dipentaerythritol penta(meth)acrylate, their ethoxylated products, their propoxylated products, their ethoxylated propoxylated products, and their caprolactone-modified products; tri- or higher functional epoxy (meth)acrylates such as phenol novolac type epoxy (meth)acrylate, cresol novolac type epoxy poly(meth)acrylate, and isocyanuric acid type epoxy tri(meth)acrylate; and hydroxypropylated products such as trimethylolpropane tri(meth)acrylate and ditrimethylolpropane tetra(meth)acrylate.
These may be used alone or in combination of two or more.

Here, the ethoxylated, propoxylated, ethoxylated propoxylated, and hydroxypropylated (meth)acrylates are obtained, for example, by using as a raw material an alcohol compound (or a phenol compound) which is a raw material for the (meth)acrylate, to which one or more ethylene oxide groups, propylene oxide groups, ethylene oxide groups and propylene oxide groups, and hydroxypropyl groups have been added.
The caprolactone modified product can be obtained by, for example, using as a raw material an alcohol compound (or a phenol compound) which is a raw material for the (meth)acrylate, modified with ε-caprolactone.

Examples of isocyanate compounds having an isocyanate group include compounds having at least one isocyanate group per molecule, and may be compounds having 1 to 3 isocyanate groups per molecule. More specifically, the monoisocyanate compounds include aliphatic monoisocyanate compounds such as ethyl isocyanate, propyl isocyanate, butyl isocyanate, octadecyl isocyanate, and 2-isocyanatoethyl (meth)acrylate; alicyclic monoisocyanate compounds such as cyclohexyl isocyanate; aromatic monoisocyanate compounds such as phenyl isocyanate; aliphatic diisocyanate compounds such as tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, decamethylene diisocyanate, and dodecamethylene diisocyanate; 1,3-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 2,5-bis(isocyanatomethyl)norbornene, bis(4-isocyanatocyclohexyl)methane, 1,2-bis(4-isocyanatocyclohexyl)methane, and the like. alicyclic diisocyanate compounds such as 2,2-bis(4-isocyanatocyclohexyl)ethane, 2,2-bis(4-isocyanatocyclohexyl)propane, 2,2-bis(4-isocyanatocyclohexyl)hexafluoropropane, and bicycloheptane triisocyanate; diisocyanate compounds such as 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, hydrogenated xylylene diisocyanate, and naphthalene-1,5-diisocyanate; and polymers such as uretdione dimers, isocyanurate types, and biuret trimers of these diisocyanate compounds. These can be used alone or in combination of two or more types, and the two or three isocyanate compounds constituting the polymer may be the same or different.

Among these, from the viewpoint of improving pattern formability, diisocyanate compounds such as aliphatic diisocyanate compounds, alicyclic diisocyanate compounds, and aromatic diisocyanate compounds, and polymers of these diisocyanate compounds may be appropriately selected, and in particular, hexamethylene diisocyanate, isophorone diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, and isocyanurate type polymers (isocyanurate type polyisocyanates) may be appropriately selected.

The reaction product of the above-mentioned (meth)acrylate having a hydroxyl group and an isocyanate compound has a (meth)acryloyl group as a photopolymerizable functional group and a urethane bond as a carbon-nitrogen bond, and more specifically, for example, has an organic group derived from the (meth)acrylate having a hydroxyl group in the molecule (i.e., an organic group having 1 to 5 (meth)acryloyl groups, which is the residue obtained by removing the hydroxyl group from the above-mentioned (meth)acrylate having a hydroxyl group), a urethane bond, and an organic group derived from the above-mentioned isocyanate compound (i.e., an organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, which is the residue obtained by removing the isocyanate group from the above-mentioned isocyanate compound). These organic groups may be the same or different.

The urethane (meth)acrylate of component (A) may include, for example, a reaction product obtained by reacting a (meth)acrylate having a hydroxyl group with a terminal isocyanate group of a polyaddition product of an isocyanate compound having at least two isocyanate groups in one molecule and a diol compound, from the viewpoint of improving pattern formability.

Examples of the isocyanate compound having at least two isocyanate groups in one molecule used here include, among the compounds exemplified as the isocyanate compound above, diisocyanate compounds such as aliphatic diisocyanate compounds, alicyclic diisocyanate compounds, and aromatic diisocyanate compounds, as well as multimers of these diisocyanate compounds such as uretdione dimers, isocyanurate dimers, and biuret trimers.
The above isocyanate compounds may be used alone or in combination of two or more kinds.

Examples of the diol compound include diol compounds having 1 to 20 carbon atoms, and specific examples thereof include linear or branched saturated diol compounds such as ethylene glycol, diethylene glycol, propanediol, dipropylene glycol, butanediol, pentanediol, isopentyl glycol, hexanediol, nonanediol, decanediol, dodecanediol, dimethyldodecanediol, and octadecanediol; linear or branched unsaturated diol compounds such as butenediol, pentenediol, hexenediol, methylpentenediol, and dimethylhexenediol; and diol compounds having an alicyclic skeleton such as various cyclohexanediols, various cyclohexanedimethanols, various tricyclodecanedimethanols, hydrogenated bisphenol A, and hydrogenated bisphenol F. Here, the above-mentioned saturated diol compounds and unsaturated diol compounds can be collectively referred to as diol compounds having a chain hydrocarbon skeleton.
The above diol compounds may be used alone or in combination of two or more.

The diol compound having a chain hydrocarbon skeleton may be appropriately selected from saturated diol compounds having 1 to 20, 2 to 16, or 2 to 14 carbon atoms, from the viewpoints of improving pattern formability and increasing the glass transition point (Tg) after polymerization to improve water resistance, and more specifically, may be appropriately selected from ethylene glycol and octadecanediol.
In addition, the diol compound having an alicyclic skeleton may be appropriately selected from diol compounds having an alicyclic skeleton having 5 to 20, 5 to 18, or 6 to 16 carbon atoms, from the viewpoints of improving pattern formability and increasing the glass transition point (Tg) after polymerization to improve water resistance. More specifically, the diol compound may be appropriately selected from various cyclohexane diols such as 1,3-cyclohexane diol and 1,4-cyclohexane diol, and various cyclohexane dimethanols such as 1,3-cyclohexane dimethanol and 1,4-cyclohexane dimethanol.

The (meth)acrylate having a hydroxyl group used here may be any of the (meth)acrylates exemplified above as being used in the reaction product of a (meth)acrylate having a hydroxyl group and an isocyanate compound having an isocyanate group.

An example of a reaction product obtained by reacting a terminal isocyanate group of a polyaddition product of an isocyanate compound having at least two isocyanate groups in one molecule with a diol compound with a (meth)acrylate having a hydroxyl group is one having a structural unit represented by the following general formula (1).

In the general formula (1), _X1 represents a divalent organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, and _Y1 represents a divalent organic group having a chain hydrocarbon skeleton or an alicyclic skeleton. When the component (A) has a plurality of the above structural units, the plurality of _X1s and _Y1s may be the same or different. That is, the component (A) may have at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton.

Examples of the divalent organic group of _X1 include organic groups derived from the aliphatic diisocyanate compounds, alicyclic diisocyanate compounds, and aromatic diisocyanate compounds exemplified above as compounds having an isocyanate group, i.e., divalent organic groups having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, which are residues obtained by removing an isocyanate group from the above isocyanate compounds. The divalent organic group represented by _X1 may be these residues themselves, or may be residues derived from isocyanate compound derivatives such as polyaddition products of the above isocyanate compounds and diol compounds.
From the viewpoints of improving the pattern formability and improving the transparency, water resistance, and moisture resistance of the resin composition in a well-balanced manner, _X1 may be a divalent organic group having an alicyclic skeleton, particularly a divalent organic group having an alicyclic skeleton which is a residue of isophorone diisocyanate represented by the following formula (2).

Examples of the divalent organic group having a chain hydrocarbon skeleton or an alicyclic skeleton for _Y1 include organic groups derived from the diol compounds having a chain hydrocarbon skeleton and the diol compounds having an alicyclic skeleton exemplified above as the diol compounds, i.e., divalent organic groups having a chain hydrocarbon skeleton or an alicyclic skeleton which are residues obtained by removing hydroxyl groups from the above diol compounds.
Among these, from the viewpoint of improving pattern formability and increasing the glass transition point (Tg) after polymerization to improve water resistance, the divalent organic group having a chain hydrocarbon skeleton may be appropriately selected from residues obtained by removing hydroxyl groups from saturated diol compounds having 1 to 20, 2 to 16, or 2 to 14 carbon atoms, more specifically, from residues obtained by removing hydroxyl groups from ethylene glycol or octadecanediol. From the same viewpoint, the divalent organic group having an alicyclic skeleton may be appropriately selected from residues obtained by removing hydroxyl groups from diol compounds having an alicyclic skeleton having 5 to 20, 5 to 18, or 6 to 16 carbon atoms, more specifically, from residues obtained by removing hydroxyl groups from various cyclohexanediols such as 1,3-cyclohexanediol and 1,4-cyclohexanediol, and various cyclohexanedimethanols such as 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol.

Specific examples of reaction products obtained by reacting a terminal isocyanate group of a polyaddition product of an isocyanate compound having at least two isocyanate groups in one molecule with a diol compound with a (meth)acrylate having a hydroxyl group include compounds represented by the following general formulas (3) and (4).

In formulae (3) and (4), _n1 and _n2 each independently represent an integer of 3 to 20.

When an isocyanurate trimer (isocyanurate triisocyanate), which is a trimer of diisocyanate, is used as the isocyanate compound, examples of the reaction products include the compounds shown in the following general formulas (5) and (6).

In formulae (5) and (6), _n3 and _n4 each independently represent an integer of 2 to 20.

Commercially available products containing a urethane acrylate having a structural unit represented by the above general formula (1) include, for example, UN-333 (functional group number: 2, Mw: 5,000), UN-1255 (functional group number: 2, Mw: 8,000), UN-904 (functional group number: 10, Mw: 4,900), UN-2600 (functional group number: 2, Mw: 2,500), UN-6200 (functional group number: 2, Mw: 6,500), UN-9000PEP ...1255 (functional group number: 2, Mw: 8 Examples of such copolymers include N-9200A (functionality: 2, Mw: 15,000), UN-3320HS (functionality: 15, Mw: 4,900), UN-6301 (functionality: 2, Mw: 33,000) (all trade names, manufactured by Negami Chemical Industrial Co., Ltd.), and EBECRYL8405 (addition product of urethane acrylate/1,6-hexanediol diacrylate=80/20, functionality: 4, Mw: 2,700) (trade name, manufactured by Daicel-Allnex Corporation).
Furthermore, examples of commercially available products containing a urethane methacrylate having a structural unit represented by the above general formula (1) include UN-6060PTM (number of functional groups: 2, Mw: 6,000, product name, manufactured by Negami Chemical Industries, Ltd.) etc. In the above description, the number of functional groups and Mw in parentheses are the total number of (meth)acryloyl groups contained in the urethane (meth)acrylate and the weight average molecular weight, respectively.

In addition, a commercially available product containing the urethane (meth)acrylate represented by the above general formula (3) is, for example, UN-952 (number of functional groups: 10, Mw: 6,500 to 11,000), and a commercially available product containing the urethane (meth)acrylate represented by the general formula (6) is, for example, UN-905 (number of functional groups: 15, Mw: 40,000 to 200,000) (all of the above are trade names, manufactured by Negami Chemical Industries, Ltd.).
Among these, UN-952 is particularly preferable from the viewpoints of pattern formability and photosensitivity.

The total number of (meth)acryloyl groups (number of functional groups) contained in the urethane (meth)acrylate of component (A) may be appropriately selected from 2 to 15 in one molecule from the viewpoint of improving pattern formability and heat resistance, and from 2 to 12 or 2 to 10 from the viewpoint of stabilizing the physical properties and characteristics of the obtained cured product.
If the number of functional groups is 2 or more, the pattern formability, heat resistance, and rigidity of the cured product at high temperatures can be improved. On the other hand, if the number of functional groups is 15 or less, the rigidity of the cured product is improved, and the adhesion to the substrate or the like is improved. In addition, a resin composition having a moderate viscosity can be obtained, and the coatability is improved. When the resin composition after coating is irradiated with light, the phenomenon that only the surface part is easily photocured rapidly and the inside is not photocured sufficiently can be suppressed, and excellent resolution can be obtained, so that even when a thick photosensitive layer is formed, excellent pattern formability can be obtained. Furthermore, after at least one of photocuring and heat curing is performed, the remaining unreacted (meth)acryloyl group can be reduced, and the fluctuation of the physical properties and characteristics of the obtained cured product can be further suppressed.

The weight average molecular weight of the polymer of the component (A) is 2,000 or more, and may be 2,500 or more from the viewpoint of improving the coatability and resolution of the resin composition, and may be 3,000 or more from the viewpoint of improving the developability and compatibility. On the other hand, the upper limit of the weight average molecular weight may be 40,000 or less, or 30,000 or less from the viewpoint of improving the coatability and resolution of the resin composition, and may be 20,000 or less from the viewpoint of improving the developability and compatibility.
If the weight average molecular weight is 2,000 or more, the occurrence of dripping of the composition when applied onto a substrate can be suppressed, resulting in excellent pattern formability. In addition, it is easy to form a thick photosensitive layer, and the problem of increased stress on the resin due to cure shrinkage and reduced reliability can be suppressed.
On the other hand, if the weight average molecular weight is 40,000 or less, the coating property is improved, it becomes easy to form a thick photosensitive layer, and the pattern formability is improved. In addition, the solubility in the developer is also good, so that excellent resolution can be expressed. Furthermore, the transparency of the cured product is improved, and a cured product having excellent transmittance required for a transparent material can be obtained.

The content of the component (A) may be appropriately selected from 10% by mass or more, 30% by mass or more, or 50% by mass or more based on the total solid content of the photosensitive resin composition. If the content is 10% by mass or more, the coatability is improved, and even when a thick photosensitive layer is formed, excellent pattern formability can be obtained.
Taking into consideration the pattern formability and coatability of the resulting resin composition, and the physical properties and characteristics required of a cured product of the resin composition, the upper limit of the content of component (A) may be appropriately selected from 95 mass % or less, 85 mass % or less, or 75 mass % or less, based on the total solid content of the photosensitive resin composition.
Furthermore, from the viewpoint of improving pattern formability, the content of the urethane (meth)acrylate in the component (A) may be appropriately selected from 70 to 100 mass%, 80 to 100 mass%, 90 to 100 mass%, 95 to 100 mass%, or 100 mass% (total amount) based on the total amount of solids in the component (A).

<(B) component: low molecular weight substance>
The photosensitive resin composition of the present embodiment contains, as component (B), a low molecular weight compound having a photopolymerizable functional group and a carbon-nitrogen bond, and the component (B) contains a low molecular weight compound having an acryloyl group as the photopolymerizable functional group. The "low molecular weight compound" means a compound having a weight average molecular weight of less than 2,000.
The (B) component contains a low molecular weight material having an acryloyl group as a photopolymerizable functional group. When the (B) component contains at least a low molecular weight material having an acryloyl group, sufficiently excellent pattern formability can be obtained. For example, when a compound containing a methacryloyl group but not containing an acryloyl group is used alone, it is difficult to obtain sufficient pattern formability. The (B) component may contain a urethane acrylate having a urethane bond as a carbon-nitrogen bond from the viewpoint of improving pattern formability. In general, a low molecular weight material having an acryloyl group requires a higher activation energy during photopolymerization than a low molecular weight material having a methacryloyl group, and the sensitivity is improved. In addition, when the low molecular weight material further has a carbon-nitrogen bond, it can act as a chain transfer agent for radical polymerization, and excellent pattern formability can be obtained.

Component (B) has at least one acryloyl group and at least one carbon-nitrogen bond. The total number of acryloyl groups (number of functional groups) contained in the low molecular weight component (B) may be appropriately selected from 2 to 15 in one molecule from the viewpoint of improving pattern formability and heat resistance, and from 2 to 12 or 2 to 10 from the viewpoint of stabilizing the physical properties and characteristics of the resulting cured product.

The urethane acrylate of component (B) may be a reaction product of an acrylate having a hydroxyl group and an isocyanate compound having an isocyanate group. Here, examples of the acrylate having a hydroxyl group and the isocyanate compound include the acrylate having a hydroxyl group and the isocyanate compound exemplified as those used to produce a polymeric substance. Here, examples of compounds appropriately selected from the viewpoint of improving pattern formability, etc. include the same compounds appropriately selected from the viewpoint of those used to produce a polymeric substance.

In addition, the low molecular weight urethane acrylate may be a reaction product of a terminal isocyanate group of a polyaddition product of an isocyanate compound having at least two isocyanate groups in one molecule and a diol compound, and an acrylate having a hydroxyl group is reacted with the isocyanate compound having at least two isocyanate groups in one molecule, a diol compound, and an acrylate having a hydroxyl group. Here, the isocyanate compound having at least two isocyanate groups in one molecule, a diol compound, and an acrylate having a hydroxyl group, each of which is exemplified as being used to generate a high molecular weight substance, may be exemplified as being appropriately selected from the viewpoint of improving pattern formability, etc., and the same as being appropriately selected as being used to generate a high molecular weight substance from the same viewpoint.
Examples of this reaction product include those having a structural unit represented by the following general formula (7).

In the general formula (7), _X2 represents a divalent organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, and _Y2 represents a divalent organic group having a chain hydrocarbon skeleton or an alicyclic skeleton. That is, the component (B) may have at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton. Examples of _X2 and _Y2 are the same as those of _X1 and _Y1 in the general formula (1).
From the viewpoint of improving the pattern formability and improving the transparency, water resistance, and moisture resistance of the resin composition in a well-balanced manner, _X2 may be appropriately selected from divalent organic groups having a chain hydrocarbon skeleton, divalent organic groups having a branched chain hydrocarbon skeleton, and branched alkylene groups having 2 to 12 carbon atoms, such as residues of the above-mentioned aliphatic diisocyanate compounds. From the same viewpoint, _Y2 may be appropriately selected from divalent organic groups having an alicyclic skeleton, such as residues of the above-mentioned diol compounds having an alicyclic skeleton.

Specific examples of urethane acrylates that can be used as component (B) include compounds represented by the following general formula (8):

In the above general formula (8), _n5 represents an integer of 1 to 4. ^R4 and ^R5 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and at least three of the multiple ^R4s and ^R5s are alkyl groups having 1 to 4 carbon atoms. Among the urethane acrylates represented by the above general formula (8), examples of commercially available products containing a urethane acrylate having a structural unit in which _X2 in the above general formula (7) is a residue of trimethylhexamethylene diisocyanate, which is a divalent organic group having a chain hydrocarbon skeleton, _{and Y2} is a residue of cyclohexanedimethanol, which is a divalent organic group having an alicyclic skeleton, include TMCH-5R (trade name, number of functional groups: 2, Mw: 950, manufactured by Hitachi Chemical Co., Ltd.).
In addition, examples of commercially available products containing a urethane acrylate having a structural unit represented by the above general formula (7) include KRM8452 (functional group number: 10, Mw: 1,200, manufactured by Daicel Allnex Co., Ltd.), UN-3320HA (functional group number: 6, Mw: 1,500), UN-3320HC (functional group number: 6, Mw: 1,500, manufactured by Negami Chemical Industries Co., Ltd.), etc. In the above description, the functional group number and Mw in parentheses are the functional group number and weight average molecular weight of the urethane acrylate, respectively.

The weight-average molecular weight of the low molecular weight component (B) is less than 2,000, and may be 1,800 or less from the viewpoint of improving adhesion, and may be 1,500 or less from the viewpoint of improving resolution. On the other hand, the lower limit of the weight-average molecular weight may be 500 or more from the viewpoint of film formability, although it may be appropriately set according to the desired purpose.

The content of the (B) component may be appropriately selected from 3% by mass or more, 5% by mass or more, 10% by mass or more, or 20% by mass or more based on the total solid content of the photosensitive resin composition. If the content is 3% by mass or more, excellent pattern formability can be obtained even when a thick photosensitive layer is formed, and excellent rigidity of the cured product can also be obtained. From the same viewpoint, the upper limit of the content of the (B) component may be appropriately selected from 70% by mass or less, 60% by mass or less, or 50% by mass or less based on the total solid content of the photosensitive resin composition.
The content of the component (B) based on the total solid content of the component (A) may be appropriately selected from 25 to 90 mass %, 30 to 80 mass %, or 35 to 65 mass % from the viewpoint of improving pattern formability and rigidity of the cured product.
In this embodiment, a low molecular weight material having a photopolymerizable functional group other than an acryloyl group may be included depending on the desired purpose. The content of the low molecular weight material having an acryloyl group as a photopolymerizable functional group based on the total solid content of the (B) component may be appropriately selected from 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more. If the content is 70% by mass or more, excellent pattern formability can be obtained even when a thick photosensitive layer is formed, and excellent rigidity of the cured product can also be obtained. From the same viewpoint, the upper limit of the content of the low molecular weight material having an acryloyl group as a photopolymerizable functional group is 100% by mass or less, and 100% by mass, i.e., the total amount of the (B) component may have an acryloyl group as a photopolymerizable functional group.

<Component (C): Photopolymerization initiator>
The photosensitive resin composition of the present embodiment contains a photopolymerization initiator as component (C). The component (C) is not particularly limited as long as it can polymerize at least one of the components (A) and (B), and can be appropriately selected from photopolymerization initiators that are commonly used. From the viewpoint of improving pattern formability, photopolymerization initiators that generate free radicals by active light, such as acylphosphine oxide-based, oxime ester-based, aromatic ketone-based, quinone-based, alkylphenone-based, imidazole-based, acridine-based, phenylglycine-based, and coumarin-based photopolymerization initiators, can be mentioned.

Acylphosphine oxide photopolymerization initiators have an acylphosphine oxide group (>P(=O)-C(=O)- group), and examples thereof include (2,6-dimethoxybenzoyl)-2,4,6-pentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (trade name: IRGACURE-TPO, manufactured by BASF), ethyl-2,4,6-trimethylbenzoylphenylphosphinate, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (trade name: IRGACURE-819, manufactured by BASF), (2,5-dihydroxyphenyl)diphenylphosphine oxide, (p-hydroxyphenyl)diphenylphosphine oxide, bis(p-hydroxyphenyl)phenylphosphine oxide, and tris(p-hydroxyphenyl)phosphine oxide.

The oxime ester photopolymerization initiator is a photopolymerization initiator having an oxime ester bond, and examples thereof include 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(O-benzoyloxime) (product name: OXE-01, manufactured by BASF), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone-1-(O-acetyloxime) (product name: OXE-02, manufactured by BASF), and 1-phenyl-1,2-propanedione-2-[O-(ethoxycarbonyl)oxime] (product name: Quantacure-PDO, manufactured by Nippon Kayaku Co., Ltd.).

Examples of aromatic ketone photopolymerization initiators include benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone (Michler's ketone), N,N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one (product name: IRGACURE-651, manufactured by BASF), 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one (product name: IRGACURE-369, manufactured by BASF), and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one (product name: IRGACURE-907, manufactured by BASF).

Quinone-based photopolymerization initiators include, for example, 2-ethylanthraquinone, phenanthrenequinone, 2-t-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 2-methyl-1,4-naphthoquinone, and 2,3-dimethylanthraquinone.

Examples of alkylphenone-based photopolymerization initiators include benzoin-based compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin phenyl ether; 2,2-dimethoxy-1,2-diphenylethan-1-one (trade name: IRGACURE-651, manufactured by BASF Corporation), 1-hydroxy-cyclohexyl-phenyl ketone (trade name: IRGACURE-184, manufactured by BASF Corporation), 2-hydroxy-2-methyl-1 -phenylpropan-1-one (trade name: IRGACURE-1173, manufactured by BASF), 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one (trade name: IRGACURE-2959, manufactured by BASF), 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)-benzyl]phenyl}-2-methylpropan-1-one (trade name: IRGACURE-127, manufactured by BASF), etc.

As the imidazole-based photopolymerization initiator, for example, 2,4,5-triarylimidazole dimers such as 2-(o-chlorophenyl)-4,5-diphenylimidazole dimers such as 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenyl-1,3-diazol-2-yl]-4,5-diphenylimidazole, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, etc. can be mentioned.

Examples of acridine-based photopolymerization initiators include 9-phenylacridine and 1,7-bis(9,9'-acridinyl)heptane.

Examples of phenylglycine-based photopolymerization initiators include N-phenylglycine, N-methyl-N-phenylglycine, and N-ethyl-N-phenylglycine.

Examples of coumarin-based photopolymerization initiators include 7-amino-4-methylcoumarin, 7-dimethylamino-4-methylcoumarin, 7-diethylamino-4-methylcoumarin, 7-methylamino-4-methylcoumarin, 7-ethylamino-4-methylcoumarin, 7-dimethylaminocyclopenta[c]coumarin, 7-aminocyclopenta[c]coumarin, 7-diethylaminocyclopenta[c]coumarin, 4,6-dimethyl-7-ethylaminocoumarin, 4,6-diethyl-7-ethylaminocoumarin, and 4,6-dimethyl-7-diethylaminocyclopenta[c]coumarin. coumarin, 4,6-dimethyl-7-dimethylaminocoumarin, 4,6-diethyl-7-ethylaminocoumarin, 4,6-diethyl-7-dimethylaminocoumarin, 2,3,6,7,10,11-hexanehydro-1H,5H-cyclopenta[3,4][1]benzopyrano-[6,7,8-ij]quinolizine 12(9H)-one, 7-diethylamino-5',7'-dimethoxy-3,3'-carbonylbiscoumarin, 3,3'-carbonylbis[7-(diethylamino)coumarin], 7-diethylamino-3-thienoxylcoumarin, etc.

From the viewpoint of improving photocurability and sensitivity and improving pattern formability, an appropriate selection can be made from acylphosphine oxide-based photopolymerization initiators. The above component (C) can be used alone or in combination of two or more kinds. In addition, the component (C) may be synthesized by a conventional method or may be a commercially available product.

The content of component (C) may be appropriately selected from the amount at which the absorbance of light with a wavelength of 365 nm is 0.35 or less, 0.3 or less, 0.2 or less, or 0.1 or less when the thickness (thickness after drying) of the photosensitive layer formed from the photosensitive resin composition is 50 μm. By setting the content as above, even when a pattern is formed with a thick photosensitive layer of, for example, 70 μm or more, light can easily pass through to the bottom of the photosensitive layer (the surface of the photosensitive layer facing the substrate), thereby improving pattern formability. Here, the absorbance can be measured, for example, using an ultraviolet-visible spectrophotometer (product name: U-3310 Spectrophotometer, manufactured by Hitachi High-Technologies Corporation) and a polyethylene terephthalate film alone as a reference, to measure the absorbance of light with a wavelength of 365 nm. In addition, the absorbance of light with a wavelength of 365 nm when the photosensitive layer is 50 μm thick can also be calculated by converting the absorbance of a photosensitive layer with a thickness other than 50 μm to the absorbance of a layer with a thickness of 50 μm based on the Beer-Lambert law.

In addition to the above component (C), photopolymerization initiator assistants such as N,N-dimethylaminobenzoic acid ethyl ester, N,N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine, triethanolamine, and other tertiary amines can be used as component (C'). These components (C') can be used alone or in combination of two or more.

As described above, the content of component (C) may be appropriately determined based on the absorbance at a thickness of 50 μm of the photosensitive layer, and may usually be appropriately selected from 0.05 to 20 mass%, 0.1 to 10 mass%, or 0.15 to 5 mass% based on the total solid content of the photosensitive resin composition. By setting the content at the above range, the sensitivity of the photosensitive resin composition can be improved, deterioration of the resist shape can be suppressed, and pattern formability can be improved.

<Component (D): Thermal Radical Polymerization Initiator>
The photosensitive resin composition of the present embodiment may further contain (D) a thermal radical polymerization initiator. The component (D) is not particularly limited, and examples thereof include dialkyl peroxides such as α,α'-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, t-butylcumyl peroxide, and di-t-butyl peroxide; ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; 1,1-bis(t-butylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, and 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane. peroxyketals such as 1,1-bis(t-hexylperoxy)cyclohexane and 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane; hydroperoxides such as p-menthane hydroperoxide; diacyl peroxides such as octanoyl peroxide, lauroyl peroxide, stearyl peroxide and benzoyl peroxide; bis(4-t-butylcyclohexyl)peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-3-methoxybutyl peroxycarbonate, peroxycarbonates such as butyl peroxypivalate, t-hexyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyisobutyrate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylauryl peroxide-based polymerization initiators such as peroxyesters such as peroxyacetate, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate, t-butylperoxybenzoate, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, and t-butylperoxyacetate; and azo-based polymerization initiators such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(4-methoxy-2'-dimethylvaleronitrile).

As the component (D), from the viewpoint of improving pattern formability, peroxide-based polymerization initiators and dialkyl peroxide-based polymerization initiators can be mentioned, among which dicumyl peroxide can be selected. In addition, the component (D) can be used alone or in combination of two or more kinds.

When component (D) is included, its content may be appropriately selected from 0.1 to 10 mass%, 0.2 to 5 mass%, or 0.3 to 1.5 mass%, based on the total solid content of the photosensitive resin composition. By setting the content within the above range, the heat resistance of the photosensitive resin composition is improved, and the reliability when used as a permanent film is improved.

<Component (E): Inorganic Filler>
The photosensitive resin composition of the present embodiment may contain a component (E) for the purpose of further improving various properties such as adhesion between the photosensitive resin composition and a substrate, heat resistance, and rigidity of the cured product.
Examples of the component (E) include silica (SiO ₂ ), alumina (Al ₂ O ₃ ), titania (TiO ₂ ), tantalum oxide (Ta ₂ O ₅ ), zirconia (ZrO ₂ ), silicon nitride (Si ₃ N ₄ ), barium titanate (BaO.TiO ₂ ), barium carbonate (BaCO ₃ ), magnesium carbonate (MgCO ₃ ), aluminum hydroxide (Al(OH) ₃ ), magnesium hydroxide (Mg(OH) ₂ ), lead titanate (PbO.TiO ₂ ), lead zirconate titanate (PZT), lead lanthanum zirconate titanate (PLZT), gallium oxide (Ga ₂ O ₃ ), spinel (MgO.Al ₂ O ₃ ), mullite (3Al ₂ O _{3.2SiO 2} ), cordierite (2MgO.2Al _{2 O 3} ), and the like. _{Examples of} inorganic fillers _that can be _used include _3.5SiO2 ), talc ( _{3MgO.4SiO2.H2O} ), _aluminum titanate ( _TiO2.Al2O3 ), yttria-containing zirconia ( _Y2O3.ZrO2 ), barium silicate ( _BaO.8SiO2 ), boron nitride ( _BN ), calcium carbonate (CaCO3), barium sulfate ( _BaSO4 ), calcium sulfate ( _CaSO4 ), _zinc oxide (ZnO), magnesium titanate (MgO.TiO2), hydrotalcite, mica, calcined kaolin, carbon ( _C ), etc. These inorganic fillers can be used alone or in combination of two or more.

The average particle size of component (E) may be appropriately selected from 0.01 to 3 μm, 0.01 to 2 μm, or 0.02 to 1 μm from the viewpoint of improving adhesion, heat resistance, and rigidity of the cured product. Here, the average particle size of component (E) is the average particle size of the inorganic filler in a state dispersed in the photosensitive resin composition, and is a value obtained by measuring as follows. First, the photosensitive resin composition is diluted (or dissolved) 1,000 times with methyl ethyl ketone, and then the particles dispersed in the solvent are measured at a refractive index of 1.38 using a submicron particle analyzer (product name: N5, manufactured by Beckman Coulter, Inc.) in accordance with the international standard ISO13321, and the particle size at an integrated value of 50% (volume basis) in the particle size distribution is taken as the average particle size. In addition, the component (E) contained in the photosensitive layer provided on the carrier film or the cured film of the photosensitive resin composition can also be measured using the submicron particle analyzer after diluting (or dissolving) it 1,000 times (volume ratio) using a solvent as described above.

The content of the (E) component may be appropriately selected from an upper limit of 10% by mass or less, 5% by mass or less, or 1% by mass or less, based on the total solid content of the photosensitive resin composition, and the lower limit may be appropriately selected from a range of more than 0% by mass, or may be 0% by mass (not included). In this way, by substantially not including the (E) component, the transmittance of the photosensitive resin composition is improved, and even when a pattern is formed using a thick photosensitive layer of, for example, 70 μm or more, light can easily pass through appropriately to the bottom of the photosensitive layer (the surface of the photosensitive layer facing the substrate), improving pattern formability.

<Other additives>
The photosensitive resin composition of the present embodiment may further contain additives such as a silane coupling agent, a sensitizer, a heat-resistant polymer, a thermal crosslinking agent, and an adhesive aid, as necessary.

Silane coupling agents can improve the adhesion of electronic components to the substrate, and are particularly effective when the substrate contains silicon (e.g., glass substrate, silicon wafer, epoxy resin-impregnated glass cloth substrate, etc.). Examples of silane coupling agents include alkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane, (meth)acryloyl group-containing alkoxysilanes such as (meth)acryloxypropyltrimethoxysilane and (meth)acryloxypropylmethyldimethoxysilane, amine-based alkoxysilanes such as aminopropyltrimethoxysilane and aminopropyltriethoxysilane, glycidoxy group-containing alkoxysilanes such as glycidoxypropyltrimethoxysilane, glycidoxypropylmethyldiethoxysilane, and glycidoxypropylmethyldiisopropenoxysilane. These can be used alone or in combination of two or more.
From the viewpoint of further improving adhesion, a silane coupling agent having an ethylenically unsaturated group in the molecule, such as an alkoxysilane containing a (meth)acryloyl group, such as (meth)acryloxypropyltrimethoxysilane or (meth)acryloxypropylmethyldimethoxysilane, or an alkoxysilane containing a glycidoxy group, such as glycidoxypropyltrimethoxysilane, glycidoxypropylmethyldiethoxysilane, or glycidoxypropylmethyldiisopropenoxysilane, may be used.

Examples of sensitizers include pyrazolines, anthracenes, xanthones, oxazoles, benzoxazoles, thiazoles, benzothiazoles, triazoles, stilbenes, triazines, thiophenes, and naphthalimides. These can be used alone or in combination of two or more.

Examples of heat-resistant polymers include polyoxazoles and their precursors, novolac resins such as phenol novolac and cresol novolac, polyamideimides, and polyamides, which have high heat resistance and are used as engineering plastics from the viewpoint of improving processability. These can be used alone or in combination of two or more.

From the viewpoint of improving the rigidity of the cured product, examples of the thermal crosslinking agent include epoxy resins, phenolic resins substituted at the α-position with a methylol group or an alkoxymethyl group, melamine resins substituted at the N-position with at least one group selected from the group consisting of a methylol group and an alkoxymethyl group, and urea resins. These can be used alone or in combination of two or more.

The adhesion aid can be used as desired to improve the adhesion between the photosensitive resin composition and the substrate, and examples of such an adhesion aid include organic silane compounds such as γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, triethoxysilylpropylethylcarbamate, 3-(triethoxysilyl)propylsuccinic anhydride, phenyltriethoxysilane, phenyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. These can be used alone or in combination of two or more.

The content of these other additives is not particularly limited as long as it is within a range that does not impair the effects of the photosensitive resin composition of this embodiment, and may be appropriately selected from, for example, 0.1 to 10 mass%, 0.3 to 5 mass%, or 0.5 to 5 mass% based on the total solid content of the photosensitive resin composition.

<Diluent>
A diluent can be used in the photosensitive resin composition of the present embodiment as necessary. Examples of diluents include alcohols having 1 to 6 carbon atoms, such as isopropanol, isobutanol, and t-butanol; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents, such as dimethyl sulfoxide and sulfolane; esters, such as γ-butyrolactone and dimethyl carbonate; and esters, such as cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate. These can be used alone or in combination of two or more.

The amount of the diluent used may be appropriately selected from an amount that results in a total solid content in the photosensitive resin composition of 50 to 90 mass%, 60 to 80 mass%, or 65 to 75 mass%. That is, when a diluent is used, the content of the diluent in the photosensitive resin composition may be appropriately selected from 10 to 50 mass%, 20 to 40 mass%, or 25 to 35 mass%. By setting the amount of the diluent used within the above range, the coatability of the photosensitive resin composition is improved, and a more precise pattern can be formed.
Furthermore, for example, when a photosensitive layer having a thickness of 70 μm or more is to be formed, the amount can be set so that the viscosity of the photosensitive resin composition at 25° C. is 0.5 to 20 Pa·s or 1 to 10 Pa·s, taking into consideration the ease of forming the photosensitive layer.

The photosensitive resin composition of this embodiment can be obtained by uniformly kneading and mixing the above-mentioned components (A) to (C), as well as components (D) and (E) that are used as desired, other additives, and diluents, using a roll mill, bead mill, etc.

The photosensitive resin composition of the present embodiment may be used in the form of a liquid or a film.
When used in a liquid form, the method for applying the photosensitive resin composition of the present embodiment is not particularly limited, and examples thereof include various application methods such as printing, spin coating, spray coating, jet dispensing, inkjet, dip coating, etc. Among these, from the viewpoint of more easily forming a thick photosensitive layer, the printing method or spin coating method may be appropriately selected.
When used in the form of a film, it can be used, for example, in the form of a photosensitive resin film described below. In this case, a photosensitive layer of the desired thickness can be formed by laminating using a laminator or the like.

The absorbance of the photosensitive layer formed from the photosensitive resin composition of this embodiment for light with a wavelength of 365 nm at a thickness (thickness after drying) of 50 μm can be appropriately selected from 0.35 or less, 0.3 or less, 0.2 or less, or 0.1 or less. If the absorbance of the photosensitive layer at a thickness of 50 μm is 0.35 or less, even when a pattern is formed with a thick photosensitive layer of, for example, 70 μm or more, light can easily pass through appropriately to the bottom of the photosensitive layer (the surface of the photosensitive layer facing the substrate), thereby improving pattern formability.

[Photosensitive resin film]
The photosensitive resin film of this embodiment has a photosensitive layer using the photosensitive resin composition of this embodiment. The photosensitive resin film of this embodiment may also have a carrier film. In this specification, the term "layer" includes a structure having a shape formed on the entire surface when observed in a plan view, as well as a structure having a shape formed on a part of the surface.

The photosensitive resin film of this embodiment can be produced, for example, by applying the photosensitive resin composition of this embodiment to a carrier film by the various application methods described above to form a coating film, and then drying the coating film to form a photosensitive layer. In addition, when the photosensitive resin composition of this embodiment contains a diluent, at least a portion of the diluent may be removed during drying.

The coating film can be dried using hot air drying, a dryer using far infrared rays, or a dryer using near infrared rays, and the drying temperature can be appropriately selected from 60 to 120°C, 70 to 110°C, or 90 to 110°C. The drying time can be appropriately selected from 1 to 60 minutes, 2 to 30 minutes, or 5 to 20 minutes. If the photosensitive resin composition of this embodiment contains a diluent, drying under the above conditions can also remove at least a portion of the diluent.

Examples of the carrier film include polyester resin films such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyethylene naphthalate (PEN), and polyolefin resin films such as polypropylene and polyethylene. From the viewpoint of improving the mechanical strength and heat resistance of the photosensitive resin film, a polyester resin film may be selected.
The thickness of the carrier film may be appropriately selected from 10 μm to 3 mm or 10 to 200 μm, taking into consideration ease of handling and the like.

The thickness of the photosensitive layer may be appropriately selected from 1 to 500 μm, 10 to 300 μm, or 30 to 100 μm. By setting the thickness to 30 μm or more, for example, when forming a photosensitive layer having a thickness of 150 μm or more, the number of operations such as lamination can be further reduced, and by setting the thickness to 100 μm or less, deformation of the photosensitive layer due to the stress difference between the inside and outside of the winding core when the photosensitive resin film is wound around the winding core can be further reduced. Considering the effect of obtaining excellent pattern formability even when a thick photosensitive layer is formed, which is possessed by the photosensitive resin composition of this embodiment, the thickness may be 70 μm or more, or may be a thickness exceeding 100 μm. In addition, a photosensitive layer having a thickness of 70 μm or more can be obtained by, for example, laminating a photosensitive layer formed on a carrier film and a photosensitive layer formed on a protective layer described later, to obtain a photosensitive resin film having a carrier film, a thick photosensitive layer, and a protective layer in this order.

In addition, the photosensitive resin film of this embodiment can also have a protective layer laminated on the surface opposite to the surface of the photosensitive layer that contacts the carrier film. The protective layer can be, for example, a resin film such as polyethylene or polypropylene. The same resin film as the carrier film described above can be used, or a different resin film can be used.

[Method of producing the cured product]
The method for producing a cured product of this embodiment includes a step of providing a photosensitive layer on a substrate using the photosensitive resin composition or photosensitive resin film of this embodiment (photosensitive layer forming step), a step of irradiating at least a part of the photosensitive layer with active light to form a photocured portion (exposure step), and a step of removing at least a part of the photosensitive layer other than the photocured portion to form a resin pattern (removal step). In addition, if desired, the method further includes a step of heat treating the resin pattern (heating step). The method for producing a cured product of this embodiment enables the formation of a desired pattern, and by taking advantage of the characteristics of the photosensitive resin composition of this embodiment that has excellent pattern forming properties even when a thick photosensitive layer of, for example, 70 μm or more is formed, the desired pattern can be formed by a thick cured product of, for example, 70 μm or more. In this specification, the term "step" refers not only to an independent step, but also to a step that cannot be clearly distinguished from other steps, as long as the intended action of the step is achieved.

(Photosensitive layer forming process)
In forming the photosensitive layer, the photosensitive resin composition or the photosensitive resin film of the present embodiment can be applied or laminated on a substrate to form the photosensitive layer.
Examples of the substrate include glass substrates, silicon wafers, metal oxide insulators such as TiO ₂ and SiO ₂ , silicon nitride, ceramic piezoelectric substrates, and epoxy resin-impregnated glass cloth substrates.

When forming a photosensitive layer by applying a photosensitive resin composition to a substrate, the photosensitive resin composition may be dissolved in the diluent to form a solution, and then applied to the substrate, and the coating film obtained by application may be dried as necessary. The application and drying may be performed by the various application methods and coating film drying methods described above for the preparation of the photosensitive resin film.
When a photosensitive resin film is used, the photosensitive layer can be formed by a lamination method using a laminator or the like.

The thickness of the photosensitive layer provided on the substrate varies depending on the forming method (coating method or lamination method), the solid content concentration and viscosity of the photosensitive resin composition, etc., but the lower limit of the thickness of the photosensitive layer after drying may be appropriately selected from 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, 100 μm or more, more than 100 μm, or 150 μm or more. The upper limit is not particularly limited as long as the resin pattern can be formed, but may be appropriately selected from, for example, 500 μm or less, 300 μm or less, or 250 μm or less. The thickness of the photosensitive layer may be appropriately selected from the above range depending on the application, and when used for electronic components, etc., the lower limit may be appropriately selected from 70 μm or more, more than 100 μm, or 150 μm or more, and the upper limit may be appropriately selected from 500 μm or less, 300 μm or less, or 250 μm or less.
In the method for producing a cured product according to the present embodiment, a photosensitive layer is formed using the photosensitive resin composition according to the present embodiment, so that a thick photosensitive layer can be formed. For example, when forming a photosensitive layer having a thickness of 150 μm or more, the layer may be repeatedly coated (and dried, if necessary) or laminated multiple times until a desired thickness is obtained, instead of being formed by a single coating (and drying, if necessary) or lamination.

(Exposure process)
In the exposure step, the photosensitive layer provided on the substrate in the photosensitive layer forming step is at least partially irradiated with active light as necessary, and the exposed portion is photocured to form a cured portion. When irradiating with active light, the photosensitive layer may be irradiated with active light through a mask having a desired pattern, or may be irradiated with active light by a direct writing exposure method such as a laser direct imaging (LDI) exposure method or a digital light processing (DLP) exposure method.
In order to improve pattern formability, after the exposure, post-exposure baking (PEB) may be performed using a hot plate, a dryer, etc. The drying conditions are not particularly limited, but may be performed at a temperature of 60 to 120° C. or 70 to 110° C. for 15 seconds to 5 minutes or 30 seconds to 3 minutes.

The exposure dose of the actinic rays may be appropriately selected from 10 to 2,000 mJ/cm ² , 100 to 1,500 mJ/cm ² , or 300 to 1,000 mJ/cm ^2. Examples of the actinic rays used include ultraviolet rays, visible rays, electron beams, X-rays, etc. Furthermore, examples of the light source that can be used include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, halogen lamps, etc.

(Removal process)
In the removal step, at least a portion of the photosensitive layer other than the cured portion (unexposed portion) formed in the exposure step is removed to form a resin pattern. The unexposed portion may be removed using a developer such as an organic solvent.
Examples of organic solvents include ethanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, and N-methylpyrrolidone. Among them, cyclopentanone can be used from the viewpoint of development speed. These can be used alone or in combination of two or more kinds.
In addition, various commonly used additives may be added to the organic solvent used as the developer.

After removing the unexposed areas with the developer, the film may be washed (rinsed) as necessary with water, alcohol such as methanol, ethanol, or isopropyl alcohol, n-butyl acetate, propylene glycol monomethyl ether acetate, or diethylene glycol dimethyl ether acetate.

(Heating process)
The heating step is a step that is adopted as necessary, and is a step in which the resin pattern formed in the removing step is heat-treated to form a cured product. The heating step is preferably carried out for 1 to 2 hours while the heating temperature is selected and gradually increased. The heating temperature may be appropriately selected from 120 to 240°C, 140 to 230°C, or 150 to 220°C. In addition, when the temperature is gradually increased, for example, the heating step may be performed at least at about 120°C or about 160°C for 10 to 50 minutes or 20 to 40 minutes, and then at about 220°C for 30 to 100 minutes or 50 to 70 minutes.

The thickness of the resulting resin pattern is the same as the thickness of the photosensitive layer after drying, and may be appropriately selected from 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, 100 μm or more, more than 100 μm, or 150 μm or more as a lower limit, and may be appropriately selected from 500 μm or less, 300 μm or less, or 250 μm or less as an upper limit. The thickness of the resin pattern may be appropriately selected from the above ranges depending on the application, and when used for electronic components, etc., the lower limit may be appropriately selected from 70 μm or more, more than 100 μm, or 150 μm or more as a lower limit, and may be appropriately selected from 500 μm or less, 300 μm or less, or 250 μm or less as an upper limit.

[Laminate and electronic component]
The laminate of the present embodiment includes a cured product of the photosensitive resin composition of the present embodiment, and examples of the laminate include a cured product on various supports such as a substrate used in the above-mentioned method for producing a cured product, a carrier film of a photosensitive resin film, etc. The cured product of the photosensitive resin composition of the present embodiment can be formed, for example, by the above-mentioned method for producing a cured product of the present embodiment.

The thickness of the cured product in the laminate of this embodiment may be appropriately selected from a lower limit of 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, 100 μm or more, more than 100 μm, or 150 μm or more, and an upper limit of 500 μm or less, 300 μm or less, or 250 μm or less. The thickness of the cured product may be appropriately selected from the above range depending on the application, and when used for electronic components, etc., the lower limit may be appropriately selected from a lower limit of 70 μm or more, more than 100 μm, or 150 μm or more, and an upper limit may be appropriately selected from a lower limit of 500 μm or less, 300 μm or less, or 250 μm or less.

The cured product provided on the substrate obtained by the above-mentioned method for producing a cured product uses the photosensitive resin composition of this embodiment, and excellent pattern formability can be obtained even with a thick photosensitive layer of, for example, 70 μm or more, so that, for example, along with the trend toward miniaturization and high performance of electronic devices, it is possible to meet the demand for electronic circuit boards that require a thick cured product to be provided on the substrate in a finer pattern. In addition, for example, in the plating process in the production of electronic circuit boards, a reduction in yield due to short circuits between wirings can be suppressed by using the cured product formed by the photosensitive resin composition of this embodiment as an insulating film.
Therefore, the laminate of this embodiment is used as an electronic component such as an electronic circuit board in a mobile terminal such as a mobile phone.

The objectives and advantages of this embodiment will be explained in more detail below based on examples and comparative examples, but this embodiment is not limited to the following examples.

(Synthesis Example 1: Synthesis of Resin P-1)
635 g of methyl methacrylate, 30 g of butyl acrylate, 245 g of butyl methacrylate, and 75 g of 2-hydroxyethyl methacrylate were mixed to obtain a monomer mixture. 0.9 g of 2,2'-azodiisobutyronitrile was dissolved in the obtained monomer mixture to obtain a mixed solution. 1030 g of propylene glycol monomethyl ether acetate was added as a solvent to a 1 L autoclave equipped with a stirrer and a condenser, and the above mixed solution was added while stirring. Next, polymerization was performed at 90°C for 6 hours under a nitrogen atmosphere at a stirring rotation speed of 100 min ^-1 to obtain an acrylic resin solution (resin P-1). The weight average molecular weight of the obtained acrylic resin was 43,370. Here, the weight average molecular weight is a value obtained by GPC method standard polystyrene conversion using the following device, and was measured using a solution in which 0.5 mg of the polymer was dissolved in 1 mL of tetrahydrofuran (THF).
Device name: Tosoh Corporation HLC-8320GPC
Columns: Gelpack R-420, R-430, and R-440 (3 columns in series)
Detector: RI detector Column temperature: 40°C
Eluent: THF
Flow rate: 1 ml/min Standard material: polystyrene

(Examples 1 to 5, Comparative Examples 1 to 8)
The compositions were mixed according to the formulation shown in Table 1 (the values in the table indicate parts by mass of each material, and in the case of a solution, the values indicate parts by mass converted into solid content), and kneaded using a three-roll mill to prepare photosensitive resin compositions. N,N-Dimethylacetamide was added so that the solid content concentration became 60% by mass, to obtain a photosensitive resin composition.

Details of each material in Table 1 are as follows.
UN-952: Urethane acrylate (manufactured by Negami Chemical Industries Co., Ltd., product name, number of functional groups: 10, weight average molecular weight: 9,000, a reaction product of an acrylate having a hydroxyl group and a diisocyanate compound, and having an acryloyl group (photopolymerizable functional group), a urethane bond (carbon-nitrogen bond), a chain hydrocarbon skeleton, and an alicyclic hydrocarbon skeleton in the molecule.)
Resin P-1: Acrylic resin prepared in Synthesis Example 1 (weight average molecular weight: 43,370)
Z250: Cyclomer P (ACA) Z250 (trade name, manufactured by Daicel Allnex Co., Ltd., has an acryloyl group (photopolymerizable functional group) in the molecule but does not have a carbon-nitrogen bond)
TMCH-5R: Urethane acrylate (manufactured by Hitachi Chemical Co., Ltd., product name, number of functional groups: 2, weight average molecular weight: 950, having an acryloyl group (photopolymerizable functional group), a urethane bond (carbon-nitrogen bond), a chain hydrocarbon skeleton, and an alicyclic hydrocarbon skeleton in the molecule.)
FA-324A: EO-modified bisphenol A diacrylate (manufactured by Hitachi Chemical Co., Ltd., product name, number of functional groups: 2, weight average molecular weight: 512)
FA-7220M: Amide bond-containing methacrylate (manufactured by Hitachi Chemical Co., Ltd., product name)
I-819: bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (BASF Corporation, trade name)
Percumyl D: Dicumyl peroxide (product name, manufactured by NOF Corporation)
KBM-503: methacryloxypropyltrimethoxysilane (product name, manufactured by Shin-Etsu Chemical Co., Ltd.)
AY43-031: Silane coupling agent (product name, manufactured by Dow Corning Toray Co., Ltd.)

Next, the photosensitive resin composition obtained above was used to carry out various evaluations under the conditions shown below. The evaluation results are shown in Table 2.

[Preparation of photosensitive resin film]
A 50 μm-thick polyethylene terephthalate film (product name: A-4100, manufactured by Teijin Limited) was used as a carrier film, and the resin compositions of the Examples and Comparative Examples were uniformly applied onto the carrier film so that the thickness after drying would be 50 μm. Next, the resin compositions were dried by heating at 100° C. for 15 minutes using a hot air convection dryer to form a photosensitive layer, and a photosensitive resin film having a carrier film and a photosensitive layer was produced.

[Evaluation of pattern formability]
A photosensitive resin film was laminated on a glass epoxy substrate (obtained by etching copper from MCL-E-679F (product name, manufactured by Hitachi Chemical Co., Ltd.)) with the photosensitive layer of the film facing the glass epoxy substrate, and the carrier film was removed. The lamination was performed at 60° C. using a laminator. Next, the photosensitive resin film was laminated again on the photosensitive layer by the above-mentioned method, and the carrier film was removed. This process was repeated three times to obtain a laminate comprising a 200 μm-thick photosensitive layer and a carrier film on a glass epoxy substrate.
A resolution evaluation mask (details will be described later) was placed on the carrier film of the laminate, and an i-line filter (product name: HB-0365, manufactured by Asahi Spectroscopy Co., Ltd.) was then placed on top, followed by exposure using a high-precision parallel exposure machine (manufactured by Mikasa Co., Ltd.). At this time, the laminate was divided into three regions, and the three regions were exposed to light with a wavelength of 365 nm (i-line) at different exposure doses (600, 1,000, 1,400 mJ/cm ² ). After exposure, the sample was post-exposure baked on a hot plate at 90° C. for 1 minute.
Thereafter, the carrier film was removed, and the pattern was developed by immersing in a developer (cyclopentanone) for 20 minutes. The developed pattern was dried at room temperature for 30 minutes, and observed using a metal microscope to evaluate the pattern formability. The evaluation was performed according to the following criteria. Here, "formable" means that the unexposed portion is completely removed, and there is no defect such as collapse in the line portion (exposed portion). The evaluation results using the photosensitive resin compositions of Examples 1 to 5 are shown in Table 2, and the evaluation results using the resin compositions of Comparative Examples 1 to 7 are shown in Table 3.
A: 6-1 to 6-8, 7-1 to 7-6, and 8-1 to 8-5 were able to be formed.
B: 7-7 to 7-8, 8-6 to 8-8 could be formed.
C: A pattern having a line width of 30 μm or less could not be formed, or the photosensitive layer peeled off after development.

Here, the resolution evaluation mask is a mask having a predetermined line pitch and line width, and has an L-shaped and linear pattern as shown in FIG. 1 (the unit of values in FIG. 1 is μm). FIG. 1 is a schematic diagram showing a resolution evaluation mask having a line pitch of 200 μm and a line width of 30 μm among the resolution evaluation masks. In this embodiment, a mask having several combinations of line pitch and line width is used, and is indicated by A-B (A is a number corresponding to the line pitch, and B is a number corresponding to the line width) according to the line pitch and line width, with A being 6, 7, and 8 for line pitches of 100, 150, and 200 μm, respectively, and B being 1 to 8 for line widths of 5, 8, 10, 12, 15, 20, 25, and 30 μm (see Table 4). For example, a line pitch of 100 μm and a line width of 5 μm is called 6-1, and a line pitch of 200 μm and a line width of 30 μm as shown in FIG. 1 is called 8-8. Therefore, the smaller the values of A and B, the more difficult it is to form a pattern. In other words, a photosensitive resin composition that can form a pattern even when using a mask with small values of A and B can be said to have better pattern formability.

From Table 2, it was confirmed that the photosensitive resin compositions of this embodiment of Examples 1 to 5 have excellent pattern forming properties. In contrast, when the resin compositions of Comparative Examples 1 and 2 not containing the (B) component were used, a pattern could not be formed even at an exposure dose of 600 (mJ/cm ² ), and when the resin compositions of Comparative Examples 3 and 4 not containing the (A) and (B) components were used, a pattern could not be formed even at an exposure dose of 1400 (mJ/cm ² ). When the resin compositions of Comparative Examples 5 to 7 containing the (B) component but not the (A) component were used, a pattern could be formed when the resin composition of Comparative Example 6 was used and the exposure dose was set to 1400 (mJ/cm ² ), but in other cases a pattern could not be formed. In addition, when the resin composition of Comparative Example 8 containing the (A) component but not containing a low molecular weight substance having an acryloyl group as a photopolymerizable functional group was used, a pattern could not be formed at all.

[Measurement of absorbance]
For the photosensitive resin film obtained in the above [Preparation of photosensitive resin film], the absorbance of light with a wavelength of 365 nm was measured when the photosensitive layer had a thickness (thickness after drying) of 50 μm. Specifically, the absorbance (Abs) at a wavelength of 365 nm was measured using an ultraviolet-visible spectrophotometer (product name: U-3310 Spectrophotometer, manufactured by Hitachi High-Technologies Corporation). A polyethylene terephthalate (PET) film alone was used as a reference. The measurement results are shown in Table 5.

From the results in Table 5, it was confirmed that the photosensitive resin compositions of this embodiment in Examples 1 to 5 had small absorbances of 0.35 or less, 0.3 or less, or 0.2 or less for light with a wavelength of 365 nm when the photosensitive layer had a thickness (thickness after drying) of 50 μm, and that the light passed through to the bottom of the photosensitive layer (the surface of the photosensitive layer facing the substrate), thereby exhibiting excellent pattern formability. On the other hand, the resin compositions of Comparative Examples 3 to 7 had absorbances greater than 0.36.

[Evaluation of insulation reliability]
The photosensitive resin film having a thickness of 50 μm obtained in Examples 1 to 5 was laminated on the interdigital copper electrode of a TEG (Test Element Group) (WALTZ-KIT EM0101JY (product name, manufactured by WALTZ Corporation, L/S=40 μm/15 μm)) which was an evaluation device, with the photosensitive layer facing the interdigital copper electrode. The lamination was performed at 60° C. using a laminator. Next, after exposure to i-line at an exposure dose of 1000 mJ/cm ² , the film was heated on a hot plate at 90° C. for 1 minute, and the carrier film was removed. Furthermore, the film was heated in an oven at 200° C. for 1 hour, and then cooled to room temperature to obtain a measurement sample.
Lead wires were attached to the TEG electrodes of the obtained measurement samples with solder, and a high temperature and high humidity bias test was performed (voltage: 5 V (DC), test time: 100 hours, 85° C., 85% RH (using a high temperature and high humidity chamber (manufactured by ESPEC))). As a result, it was confirmed that the measurement samples obtained using the photosensitive resin films of Examples 1 to 5 all maintained a resistance value of 1.0×10 ⁷ or more during the test time (100 hours), and thus had sufficiently excellent insulation reliability.

According to the present disclosure, the following embodiments are provided.
[1] A photosensitive resin composition comprising: component (A): a high molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; component (B): a low molecular weight material having a photopolymerizable functional group and a carbon-nitrogen bond; and component (C): a photopolymerization initiator, wherein component (B) contains a low molecular weight material having an acryloyl group as the photopolymerizable functional group.
[2] The photosensitive resin composition according to [1], wherein the component (A) contains a polymer having a (meth)acryloyl group as a photopolymerizable functional group.
[3] The photosensitive resin composition according to [1] or [2], wherein the component (A) contains a polymer having a urethane bond as a carbon-nitrogen bond.
[4] The photosensitive resin composition according to any one of [1] to [3], wherein the component (A) contains a polymer having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton.
[5] The photosensitive resin composition according to any one of [1] to [4], wherein the component (B) contains a low molecular weight compound having a urethane bond as a carbon-nitrogen bond.
[6] The photosensitive resin composition according to any one of [1] to [5], wherein the component (C) contains an acylphosphine oxide-based photopolymerization initiator.
[7] The photosensitive resin composition according to any one of [1] to [6], wherein the contents of the component (A), the component (B), and the component (C) are 10 to 95 mass%, 3 to 70 mass%, and 0.05 to 20 mass%, respectively, based on the total amount of solids in the photosensitive resin composition.
[8] The photosensitive resin composition according to any one of [1] to [7], further comprising a component (D): a thermal radical polymerization initiator.
[9] The photosensitive resin composition according to any one of [1] to [8], wherein the absorbance of the composition at a thickness of 50 μm for light having a wavelength of 365 nm is 0.35 or less.
[10] A photosensitive resin film having a photosensitive layer using the photosensitive resin composition according to any one of [1] to [9].
[11] A method for producing a cured product, comprising the steps of: providing a photosensitive layer on a substrate using the photosensitive resin composition according to any one of [1] to [9] or the photosensitive resin film according to [10]; irradiating at least a portion of the photosensitive layer with active light to form a photocured portion; and removing at least a portion of the photosensitive layer other than the photocured portion to form a resin pattern.
[12] The method for producing a cured product according to [11], further comprising a step of heat treating the resin pattern.
[13] The method for producing a cured product according to [12], wherein the thickness of the resin pattern is 70 μm or more and 300 μm or less.
[14] A laminate comprising a cured product of the photosensitive resin composition according to any one of [1] to [9].
[15] The laminate according to [14], wherein the thickness of the cured product is 70 μm or more and 300 μm or less.
[16] An electronic component comprising a cured product of the photosensitive resin composition according to any one of [1] to [9].

Claims (15)

Component (A): a high molecular weight substance having a photopolymerizable functional group and a carbon-nitrogen bond and a weight average molecular weight of 3,000 to 30,000;
Component (B): a low molecular weight substance having a photopolymerizable functional group and a carbon-nitrogen bond and a weight average molecular weight of less than 2,000;
(C) component: a photopolymerization initiator;
the component (A) contains a polymer having a (meth)acryloyl group as a photopolymerizable functional group,
the total number of photopolymerizable functional groups contained in the polymer is 4 to 15,
The content of the component (A) is 50% by mass or more based on the total amount of solids in the photosensitive resin composition,
the component (B) contains a low molecular weight material having an acryloyl group as a photopolymerizable functional group and a urethane bond as a carbon-nitrogen bond,
A photosensitive resin composition in which the content of the component (C) is 0.05 to 20 mass % based on the total solid content in the photosensitive resin composition (provided that: an alkali-soluble transparent resin composition comprising (A) a carboxyl group-containing photosensitive resin, (B) an α-hydroxyketone-based photopolymerization initiator, (C) a diluent, and (D) an epoxy compound; a photosensitive resin composition comprising (A) a carboxyl group-containing resin, (B) a urethane (meth)acrylate having 6 or more functional groups, (C) a photopolymerization initiator, and (D) titanium oxide; a photosensitive resin composition comprising at least (A) a radical polymerizable group in the molecule, (B) a urethane bond- and carboxyl group-containing resin that is substantially free of a reactive group, (C) a radically polymerizable compound, (D) a reactive group-containing compound that is reactive with a carboxyl group and substantially free of an aromatic ring in the molecule, (E) a photopolymerization initiator, (F) rutile-type titanium oxide, and (G) a phosphinate, and is substantially free of a silicon-containing organic compound; and a curable composition containing silica particles having an ethylenically unsaturated group. Component (A): a high molecular weight material having a weight average molecular weight of 2,000 to 30,000 and having a photopolymerizable functional group and a carbon-nitrogen bond;
Component (B): a low molecular weight substance having a photopolymerizable functional group and a carbon-nitrogen bond and a weight average molecular weight of less than 2,000;
(C) component: a photopolymerization initiator;
the component (A) contains a polymer having a (meth)acryloyl group as a photopolymerizable functional group,
the total number of photopolymerizable functional groups contained in the polymer is 4 to 15,
The content of the component (A) is 50 % by mass or more based on the total amount of solids in the photosensitive resin composition,
the component (B) contains a low molecular weight material having an acryloyl group as a photopolymerizable functional group and a urethane bond as a carbon-nitrogen bond,
A photosensitive resin composition in which the content of the component (C) is 0.05 to 20 mass% based on the total solid content in the photosensitive resin composition (however, excluding a photosensitive resin composition characterized by containing (A) a carboxyl group-containing resin, (B) a urethane (meth)acrylate having 6 or more functional groups, (C) a photopolymerization initiator, and (D) titanium oxide; a white photosensitive resin composition characterized by containing at least (A) a urethane bond- and carboxyl group-containing resin substantially not containing a radically polymerizable group in the molecule, (B) a urethane bond- and carboxyl group-containing resin containing a radically polymerizable group in the molecule, (C) a radically polymerizable compound, (D) a reactive group-containing compound reactive with a carboxyl group substantially not containing an aromatic ring in the molecule, (E) a photopolymerization initiator, (F) a rutile-type titanium oxide, and (G) a phosphinate, and substantially not containing a silicon-containing organic compound; and a curable composition containing silica particles having an ethylenically unsaturated group). The photosensitive resin composition according to claim 1 or 2, wherein the component (A) contains a polymer having a urethane bond as a carbon-nitrogen bond. The photosensitive resin composition according to any one of claims 1 to 3, wherein the component (A) contains a polymer having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton. The photosensitive resin composition according to any one of claims 1 to 4, wherein the component (C) contains an acylphosphine oxide-based photopolymerization initiator. 6. The photosensitive resin composition according to claim 1, wherein the content of the component (A) is 50 to 95 mass % based on the total amount of solids in the photosensitive resin composition. The photosensitive resin composition according to any one of claims 1 to 6, further comprising component (D): a thermal radical polymerization initiator. The photosensitive resin composition according to any one of claims 1 to 7, which has an absorbance of 0.35 or less for light with a wavelength of 365 nm at a thickness of 50 μm. A photosensitive resin film having a photosensitive layer using the photosensitive resin composition according to any one of claims 1 to 8. A method for producing a cured product, comprising the steps of providing a photosensitive layer on a substrate using the photosensitive resin composition according to any one of claims 1 to 8 or the photosensitive resin film according to claim 9, irradiating at least a portion of the photosensitive layer with active light to form a photocured portion, and removing at least a portion of the photosensitive layer other than the photocured portion to form a resin pattern. The method for producing a cured product according to claim 10 further comprises a step of heat treating the resin pattern. The method for producing a cured product according to claim 11, wherein the thickness of the resin pattern is 70 μm or more and 300 μm or less. A laminate comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 8. The laminate according to claim 13, wherein the thickness of the cured product is 70 μm or more and 300 μm or less. An electronic component comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 8.