JP6763178B2 - Photosensitive resin composition, photosensitive resin film, method for manufacturing cured product, laminate, and electronic components - Google Patents

Description

The present disclosure relates to photosensitive resin compositions, photosensitive resin films, methods for producing cured products, laminates, and electronic components.

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 production of a wiring board, a resist is formed using a photosensitive resin composition, and then a conductor pattern, a metal post, or the like is formed by a plating process. More specifically, a photosensitive layer is formed on a support (substrate) using a photosensitive resin composition or the like, and the photosensitive layer is exposed through a predetermined mask pattern, followed by a conductor pattern and a metal post. A resist pattern (resist) is formed by developing a portion such as, etc. so that it can be selectively removed (peeled). Next, a conductor such as copper is formed on the removed portion by a plating treatment, and then the resist pattern is removed to manufacture a wiring board provided with a conductor pattern, a metal post, or the like.

Conventionally, a thick conductor pattern and a metal post have been produced by growing a metal plating after removing a resist pattern. In order to meet such demands, for example, a photosensitive resist for a thick film having a thickness of about 30 μm and a thickness of about 65 μm has been used (see Patent Documents 1 and 2).
Further, in recent years, in order to further improve the performance, the conductor layer has a thickness of 150 μm by performing a plating treatment while selectively destroying a layer existing in the direction in which plating growth is desired among the metal ion dilute layers with a plating solution. Attempts have been made to form the film as thick as possible (see Patent Document 3).

Japanese Unexamined Patent Publication No. 2015-034926 Japanese Unexamined Patent Publication No. 2014-077774 Japanese Unexamined Patent Publication No. 2014-080674

However, in the conventional photosensitive resist for a thick film, for example, when it is required to form a thick photosensitive layer of 70 μm or more, light may not easily pass to the bottom and the pattern shape may be deteriorated. Further, in the method described in Patent Document 3, since the plating proceeds while partially destroying the metal ion dilute layer, it is difficult to stably form an excellent pattern. Therefore, even when a photosensitive layer having a thickness of 70 μm, 150 μm thicker than the conventional one, or more (thickness in the direction perpendicular to the substrate) is formed, the photosensitive layer has excellent pattern forming properties. Resist is required.

Therefore, the problem to be solved by the present disclosure has been made in view of the above circumstances. For example, a photosensitive resin having excellent pattern forming property even when a thick photosensitive layer of 70 μm or more is formed. It is an object of the present invention to provide a composition, a photosensitive resin film, a method for producing a cured product, a laminate, and an electronic component (hereinafter, may be referred to as a "photosensitive resin composition or the like").

As a result of intensive studies to solve the above problems, the present inventors have found that the problem can be solved by a photosensitive resin composition having the following constitution. The present disclosure provides the following photosensitive resin compositions and the like.

[1] Component (A): Two or more compounds having a photopolymerizable functional group and a urethane bond, and component (B): a photopolymerization initiator.
The component (B) is an acylphosphine oxide-based photopolymerization initiator, an aromatic ketone-based photopolymerization initiator, a quinone-based photopolymerization initiator, an alkylphenone-based photopolymerization initiator, an acrydin-based photopolymerization initiator, and a phenylglycine-based component. A photosensitive resin composition containing at least one photopolymerization initiator selected from the group consisting of a photopolymerization initiator and a coumarin-based photopolymerization initiator.
[2] In the above [1], the component (B) contains at least one photopolymerization initiator selected from the group consisting of an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator. The photosensitive resin composition according to the above.
[3] Component (A): Two or more compounds having a photopolymerizable functional group and a urethane bond, and component (B): a photopolymerization initiator.
A photosensitive resin composition containing a photopolymerization initiator having a molar extinction coefficient of the component (B) of 2,000 L / mol · cm or less.
[4] The photosensitive resin composition according to any one of the above [1] to [3], wherein the component (A) contains two or more compounds having a (meth) acryloyl group as a photopolymerizable functional group.
[5] The photosensitive resin composition according to any one of the above [1] to [4], wherein the component (A) contains a high molecular weight substance having a photopolymerizable functional group and a urethane bond.
[6] The above [1] to [6], wherein the component (A) contains a high molecular weight body 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.
[7] The photosensitive resin composition according to any one of [1] to [6] above, wherein the component (A) contains a low molecular weight substance having a photopolymerizable functional group and a urethane bond.
[8] The photosensitive resin composition according to the above [7], wherein the low molecular weight substance as the component (A) contains a low molecular weight substance having two or more (meth) acryloyl groups as photopolymerizable functional groups. ..
[9] The photosensitive resin composition according to any one of the above [1] to [8], which further contains a component (C): a low molecular weight substance having an isocyanul ring skeleton or an alicyclic skeleton.
[10] The photosensitive substance according to the above [9], wherein the low molecular weight substance as the component (C) contains a low molecular weight substance having two or more (meth) acryloyl groups together with an isocyanul ring skeleton or an alicyclic skeleton. Resin composition.
[11] The photosensitive resin composition according to any one of the above [1] to [10], which further contains a component (D): a silane compound.
[12] The photosensitive resin composition according to the above [11], wherein the component (D) contains a silane compound having a thiol group.
[13] A photosensitive resin film having a photosensitive layer using the photosensitive resin composition according to any one of the above [1] to [12].
[14] A step of providing a photosensitive layer on a substrate using the photosensitive resin composition according to any one of the above [1] to [12] or the photosensitive resin film according to the above [13]. Curing includes, in order, a step of irradiating at least a part of the layer with active light to form a photocurable portion, and a step of removing at least a part other than the photocurable portion of the photosensitive layer to form a resin pattern. How to make things.
[15] The method for producing a cured product according to the above [14], further comprising a step of heat-treating the resin pattern.
[16] The method for producing a cured product according to the above [14] or [15], wherein the thickness of the resin pattern is 70 μm or more and 300 μm or less.
[17] A laminate comprising a cured product of the photosensitive resin composition according to any one of the above [1] to [12].
[18] The laminate according to the above [17], wherein the thickness of the cured product is 70 μm or more and 300 μm or less.
[19] An electronic component comprising a cured product of the photosensitive resin composition according to any one of the above [1] to [12].

According to the present disclosure, for example, it is possible to provide a photosensitive resin composition having excellent pattern forming property even when a thick photosensitive layer of 70 μm or more is formed.

It is a schematic diagram of the mask for resolution evaluation used in an Example.

Hereinafter, the present disclosure will be described in detail.
In the present specification, the numerical range indicated by using "~" indicates a range including the numerical values before and after "~" as the minimum value and the maximum value, respectively. Further, in the numerical range described stepwise in the present specification, the upper limit value or the lower limit value of the numerical range of one step may be replaced with the upper limit value or the lower limit value of the numerical range of another step. In the numerical range described in the present specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
The term "(meth) acrylic acid" means at least one of "acrylic acid" and the corresponding "methacrylic acid", and the same applies to other similar expressions such as (meth) acrylate.

[Photosensitive resin composition]
One of the photosensitive resin compositions according to the embodiment in the present disclosure (hereinafter, may be simply referred to as the present embodiment) is
[I] Component (A): Two or more compounds having a photopolymerizable functional group and urethane bond, and component (B): a photopolymerization initiator.
The component (B) is an acylphosphine oxide-based photopolymerization initiator, an aromatic ketone-based photopolymerization initiator, a quinone-based photopolymerization initiator, an alkylphenone-based photopolymerization initiator, an acrydin-based photopolymerization initiator, and a phenylglycine-based component. A photosensitive resin composition containing a photopolymerization initiator selected from the group consisting of a photopolymerization initiator and a coumarin-based photopolymerization initiator.
Another aspect of the photosensitive resin composition according to this embodiment is
[II] Component (A): Two or more compounds having a photopolymerizable functional group and urethane bond, and component (B): a photopolymerization initiator.
A photosensitive resin composition containing a photopolymerization initiator having a molar extinction coefficient of the component (B) of 2,000 L / mol · cm or less.
In addition, in this specification, a "solid content" is a non-volatile content excluding volatile substances such as water and a solvent contained in a photosensitive resin composition, and when the resin composition is dried, it means. , Shows components that remain unvolatilized, and also includes those that are liquid, starch syrup, and wax at room temperature. In the present specification, room temperature refers to 25 ° C.
Hereinafter, each component will be described.

<Component (A): Compound having photopolymerizable functional group and urethane bond>
The photosensitive resin composition of the present embodiment contains two or more compounds having a photopolymerizable functional group and a urethane bond as the component (A). By containing two or more kinds of components (A) having different structures, the effect of improving the pattern forming property is greatly improved.
Examples of the photopolymerizable functional group contained in the compound include ethylenically unsaturated groups such as (meth) acryloyl group; alkenyl group such as vinyl group and allyl group. From the viewpoint of improving the pattern forming property, the component (A) may contain two or more compounds having a (meth) acryloyl group as a photopolymerizable functional group.
The component (A) has at least one photopolymerizable functional group and at least one urethane bond. Further, from the viewpoint of improving the pattern forming property when a thick photosensitive layer of 70 μm or more is formed, the lower limit of the content of the component (A) is 70% by mass based on the total solid content of the photosensitive resin composition. As described above, 80% by mass or more, 85% by mass or more, 90% by mass or more, or 95% by mass or more may be appropriately selected. Considering the pattern-forming property and coatability of the obtained resin composition, and the physical properties and characteristics required for the cured product of the resin composition, the upper limit is not particularly limited, but the total solid content of the photosensitive resin composition is used as a reference. It can be appropriately selected from 100% by mass or less, 99% by mass or less, 95% by mass or less, 85% by mass or less, or 80% by mass or less. The number of photopolymerizable functional groups contained in the component (A) is not particularly limited, but from the viewpoint of improving pattern formation and heat resistance, 2 to 30, 2 to 24, 2 to 20, 2 in one molecule. ~ 15, 4 ~ 12, 4-10, 8 ~ 15, 8 ~ 12, 15-24, or 18 ~ 22 may be appropriately selected, and from the viewpoint of stabilizing the physical properties and properties of the obtained cured product. , 2 to 20, 2 to 10 can be appropriately selected.
The compound of the component (A) may be a high molecular weight substance or a low molecular weight substance. That is, the component (A) may contain a high molecular weight substance having a photopolymerizable functional group and a urethane bond, or may contain a low molecular weight substance having a photopolymerizable functional group and a urethane bond. As one aspect of the present embodiment, the component (A) may contain a high molecular weight substance having a photopolymerizable functional group and a urethane bond, and a low molecular weight body having a photopolymerizable functional group and a urethane bond. Further, in consideration of pattern forming property and tack property, those having two peaks in the molecular weight distribution of the component (A) may be used.
As described above, the photosensitive resin composition of the present embodiment contains two or more compounds having a photopolymerizable functional group and a urethane bond as the component (A). More specifically, as the component (A), one or more high molecular weight substances having a photopolymerizable functional group and a urethane bond and one or more low molecular weight substances having a photopolymerizable functional group and a urethane bond may be contained. However, it may contain two or more kinds of high molecular weight compounds having a photopolymerizable functional group and a urethane bond, or may contain two or more kinds of low molecular weight bodies having a photopolymerizable functional group and a urethane bond. ..
When two or more kinds of high molecular weight substances having a photopolymerizable functional group and a urethane bond are contained, one or more kinds of low molecular weight bodies having a photopolymerizable functional group and a urethane bond may be further contained. Further, when two or more kinds of low molecular weight substances having a photopolymerizable functional group and a urethane bond are contained, one or more kinds of high molecular weight substances having a photopolymerizable functional group and a urethane bond may be further contained.
A high molecular weight substance having a photopolymerizable functional group and a urethane bond and a low molecular weight substance having a photopolymerizable functional group and a urethane bond will be described in order below.

(High molecular weight body having photopolymerizable functional group and urethane bond)
The "high molecular weight substance" means a compound having a weight average molecular weight (Mw) of 2,000 or more. In this specification, the value of the weight average molecular weight is a value obtained by gel permeation chromatography (GPC) method using tetrahydrofuran (THF) in terms of standard polystyrene.
Examples of the photopolymerizable functional group contained in the photopolymerizable functional group and the high molecular weight substance having a urethane bond (hereinafter, may be simply referred to as the high molecular weight body) include a (meth) acryloyl group; a vinyl group and an allyl group. Examples thereof include alkenyl groups such as, and ethylenically unsaturated groups such as. From the viewpoint of improving the pattern forming property, the high molecular weight material may contain a high molecular weight material having a (meth) acryloyl group as a photopolymerizable functional group. Examples of the high molecular weight substance having a (meth) acryloyl group include (meth) acrylate and (meth) acrylate having a urethane bond (hereinafter, may be referred to as “urethane (meth) acrylate”).
The high molecular weight body has at least one photopolymerizable functional group and at least one urethane bond. The number of photopolymerizable functional groups contained in the high molecular weight substance is not particularly limited, but from the viewpoint of improving pattern forming property and heat resistance, 2 to 30, 2 to 24, 2 to 20, 2 to 2 in one molecule. It may be appropriately selected from 15, 4 to 12, 4 to 10, 8 to 15, 8 to 12, 15 to 24, or 18 to 22, and from the viewpoint of stabilizing the physical properties and properties of the obtained cured product. , 2 to 20, 2 to 10 can be appropriately selected.
The high molecular weight body may contain a high molecular weight body having 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 high molecular weight urethane (meth) acrylate 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 a compound having at least one hydroxyl group and at least one (meth) acryloyl group in one molecule. More specifically, for example, 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, 2-hydroxy- Monofunctional (meth) acrylates such as 3- (2-naphthoxy) propyl (meth) acrylates, their ethoxylated forms, their propoxylates, their ethoxylated propoxylates, and their caprolactone variants; trimethylol Bifunctional (meth) acrylates such as propanedi (meth) acrylate, glycerindi (meth) acrylate, bis (2- (meth) acryloyloxyethyl) (2-hydroxyethyl) isocyanurate, these ethoxylated forms, these Propoxides of, these ethoxylated propoxys, and their caprolactone variants; cyclohexanedimethanol type epoxy di (meth) acrylate, tricyclodecanedimethanol type epoxy di (meth) acrylate, hydrogenated bisphenol A type epoxy di (meth). ) Acrylate, hydrogenated bisphenol F type epoxy di (meth) acrylate, hydroquinone type epoxy di (meth) acrylate, resorcinol type epoxy di (meth) acrylate, catechol type epoxy di (meth) acrylate, bisphenol A type epoxy di (meth) acrylate, bisphenol F type Bifunctional epoxy (meth) acrylates such as epoxy di (meth) acrylate, bisphenol AF type epoxy di (meth) acrylate, biphenol type epoxy di (meth) acrylate, fluorene bisphenol type epoxy di (meth) acrylate, and isocyanurate monoallyl type epoxy di (meth) acrylate. Trifunctional or higher functional (meth) acrylates such as ditrimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and ethoxylation thereof. The body, these propoxys, these ethoxylated propoxys, and these caprolactone variants; Trifunctional or higher functional epoxy (meth) acrylates such as enol novolac type epoxy (meth) acrylate, cresol novolac type epoxy poly (meth) acrylate, and isocyanuric acid type epoxy tri (meth) acrylate; trimethylolpropane tri (meth) acrylate, ditri Examples thereof include hydroxypropylated products such as methylolpropanetetra (meth) acrylate.
These can be used alone or in combination of two or more.

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

Examples of the isocyanate compound having an isocyanate group include a compound having at least one isocyanate group in one molecule, and may be a compound having 1 to 3 isocyanate groups in one molecule. More specifically, aliphatic monoisocyanate compounds such as ethyl isocyanate, propyl isocyanate, butyl isocyanate, octadecyl isocyanate and 2-isocyanate ethyl (meth) acrylate; alicyclic monoisocyanate compounds such as cyclohexyl isocyanate; aromatics such as phenylisocyanate. Monoisocyanate compounds such as group monoisocyanate compounds; aliphatic diisocyanate compounds such as tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate; 1,3-bis (isocyanatomethyl) cyclohexane , Isophorone diisocyanate, 2,5-bis (isocyanatomethyl) norbornene, bis (4-isocyanatocyclohexyl) methane, 1,2-bis (4-isocyanatocyclohexyl) ethane, 2,2-bis (4-isocyanatocyclohexyl) Alicyclic diisocyanate compounds such as cyclohexyl) propane, 2,2-bis (4-isocyanatocyclohexyl) hexafluoropropane, bicycloheptanetriisocyanate; 1,4-phenylenediocyanate, 2,4-tolylene diisocyanate, 2,6 Fragrances such as -tolylene diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, hydrogenated xylylene diisocyanate, naphthalene-1,5-diisocyanate Examples thereof include diisocyanate compounds such as diisocyanate compounds, and multimers such as uretdione-type dimer, isocyanurate-type, and biuret-type trimer of these diisocyanate compounds. These can be used alone or in combination of two or more, and the two or three isocyanate compounds constituting the multimer may be the same or different.

Among them, from the viewpoint of improving the pattern forming property, a diisocyanate compound such as an aliphatic diisocyanate compound, an alicyclic diisocyanate compound, an aromatic diisocyanate compound, and a multimer of these diisocyanate compounds may be appropriately selected, and in particular, hexamethylene diisocyanate. , Isophorone diisocyanate, 1,4-phenylenediocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, and isocyanurate-type multimers ( Isocyanurate-type polyisocyanate) may be appropriately selected.

The reaction product of the (meth) acrylate having a hydroxyl group and the isocyanate compound described above has a (meth) acryloyl group as a photopolymerizable functional group and has a urethane bond, and more specifically, For example, it has an organic group derived from a (meth) acrylate having a hydroxyl group in the molecule (that is, having 1 to 5 (meth) acryloyl groups which are residues obtained by removing the hydroxyl group from the (meth) acrylate having the above hydroxyl group. An organic group (which can also be called an organic group), a urethane bond, and an organic group derived from the above-mentioned isocyanate compound (that is, a residue obtained by removing the isocyanate group from the above-mentioned isocyanate compound, such as a chain hydrocarbon skeleton, an alicyclic skeleton, or It can be said to be an organic group having an aromatic ring skeleton). These organic groups may be the same or different.

As the high molecular weight urethane (meth) acrylate, from the viewpoint of improving the pattern forming property, for example, the terminal isocyanate group of the heavy adduct of the isocyanate compound having at least two isocyanate groups in one molecule and the diol compound can be used. It may contain a reaction product obtained by reacting a (meth) acrylate having a hydroxyl group.

As the isocyanate compound used here having at least two isocyanate groups in one molecule, among the compounds exemplified as the above-mentioned isocyanate compounds, diisocyanate compounds such as aliphatic diisocyanate compounds, alicyclic diisocyanate compounds and aromatic diisocyanate compounds are used. In addition, multimers such as uretdione-type dimer, isocyanurate-type, and biuret-type trimer of these diisocyanate compounds can be mentioned.
The above isocyanate compounds can be used alone or in combination of two or more.

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

The diol compound having a chain hydrocarbon skeleton has 1 to 20 carbon atoms and 2 to 16 carbon atoms from the viewpoint of improving the pattern forming property and increasing the glass transition point (Tg) after polymerization to improve the water resistance. , 2 to 14 saturated diol compounds may be appropriately selected, and more specifically, ethylene glycol and octadecane diol may be appropriately selected.
Further, the diol compound having an alicyclic skeleton has 5 to 20, 5 carbon atoms from the viewpoint of improving pattern forming property and increasing the glass transition point (Tg) after polymerization to improve water resistance. It may be appropriately selected from diol compounds having 18, 6 to 16 alicyclic skeletons, and more specifically, various cyclohexanediols such as 1,3-cyclohexanediol and 1,4-cyclohexanediol, 1,3-. It may be appropriately selected from various cyclohexanedimethanols such as cyclohexanedimethanol and 1,4-cyclohexanedimethanol.

Further, as the (meth) acrylate having a hydroxyl group used here, those exemplified as the (meth) acrylate used for the reaction product of the above-mentioned (meth) acrylate having a hydroxyl group and the isocyanate compound having an isocyanate group are exemplified. Can be mentioned.

As a reaction product obtained by reacting a (meth) acrylate having a hydroxyl group with a terminal isocyanate group of a heavy adduct of an isocyanate compound having at least two isocyanate groups in one molecule and a diol compound, for example, the following general formula ( Examples thereof include those having a structural unit represented by 1).

In the general formula (1), X ₁ represents a divalent organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, and Y ₁ represents a chain hydrocarbon skeleton or an alicyclic skeleton. Indicates a divalent organic group having. Further, when the component (A) has a plurality of the structural units, the plurality of X ₁ and Y ₁ may be the same or different. That is, as the component (A), a component having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton can be mentioned.

Examples of the divalent organic group of X ₁ include an aliphatic diisocyanate compound, an alicyclic diisocyanate compound, and an organic group derived from an aromatic diisocyanate compound, that is, the above-mentioned isocyanate compound, which is exemplified as the compound having an isocyanate group. Examples thereof include a divalent organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, which is a residue excluding the isocyanate group. Further, the divalent organic group represented by X ₁ may be these residues themselves, or residues derived from an isocyanate compound derivative such as a heavy adduct of the isocyanate compound and the diol compound. You may.
From the viewpoint of improving the pattern forming property and improving the transparency, water resistance, and moisture resistance of the resin composition in a well-balanced manner, X ₁ is a divalent organic group having an alicyclic skeleton, among which the following formula is used. It may be a divalent organic group having an alicyclic skeleton, which is a residue of isophorone diisocyanate represented by (2).

Examples of the divalent organic group having a chain hydrocarbon skeleton or an alicyclic skeleton of Y ₁ include a diol compound having a chain hydrocarbon skeleton and a diol having an alicyclic skeleton exemplified as the above diol compound. Examples thereof include an organic group derived from the compound, that is, a divalent organic group having a chain hydrocarbon skeleton or an alicyclic skeleton, which is a residue obtained by removing a hydroxyl group from the above diol compound.
Among them, the divalent organic group having a chain hydrocarbon skeleton has 1 carbon atom from the viewpoint of improving the pattern forming property and increasing the glass transition point (Tg) after polymerization to improve the water resistance. It may be appropriately selected from the residues obtained by removing the hydroxyl groups from the saturated diol compounds of ~ 20, 2 to 16 and 2 to 14, and more specifically, it may be appropriately selected from the residues obtained by removing the hydroxyl groups from ethylene glycol and octadecanediol. Just do it. From the same viewpoint, as the divalent organic group having an alicyclic skeleton, the residue obtained by removing the hydroxyl group from the diol compound having an alicyclic skeleton having 5 to 20, 5 to 18, 6 to 16 carbon atoms. It may be appropriately selected from the groups, and more specifically, various cyclohexanediols such as 1,3-cyclohexanediol and 1,4-cyclohexanediol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol and the like. It may be appropriately selected from the residues obtained by removing the hydroxyl group from various cyclohexanedimethanol.

Specifically, as a reaction product obtained by reacting a (meth) acrylate having a hydroxyl group with a terminal isocyanate group of a heavy adduct of an isocyanate compound having at least two isocyanate groups in one molecule and a diol compound, for example, , Compounds represented by the following general formulas (3) and (4) can be mentioned.

In the general formulas (3) and (4), n ₁ and n ₂ each independently represent an integer of 3 to 20.

Further, as the reaction product when an isocyanurate-type trimer (isocyanurate-type triisocyanate), which is a trimer of diisocyanate, is used as the isocyanate compound, for example, the following general formulas (5) and (6) are used. Examples include the compounds shown.

In the general formulas (5) and (6), n ₃ and n ₄ each independently represent an integer of 2 to 20.

Examples of commercially available products containing urethane acrylate having the structural unit represented by the general formula (1) include UN-953: (number of functional groups: 20, weight average molecular weight: 14,000 to 40,000), UN-. 954: (Number of functional groups: 6, weight average molecular weight: 4,500), H-219 (number of functional groups: 9, weight average molecular weight: 25,000 to 50,000), UN-333 (number of functional groups: 2, Mw: 5,000), UN-1255 (number of functional groups: 2, Mw: 8,000), UN-904 (number of functional groups: 10, Mw: 4,900), UN-2600 (number of functional groups: 2, Mw: 2, 500), UN-6200 (number of functional groups: 2, Mw: 6,500), UN-9000PEP (number of functional groups: 2, Mw: 5,000), UN-9200A (number of functional groups: 2, Mw: 15,000) , UN-3320HS (number of functional groups: 15, Mw: 4,900), UN-6301 (number of functional groups: 2, Mw: 33,000) (all of the above are trade names, manufactured by Negami Kogyo Co., Ltd.), EBECRYL8405 (urethane) Examples thereof include commercially available products such as an addition reaction product of acrylate / 1,6-hexanediol diacrylate = 80/20, the number of functional groups: 4, Mw: 2,700) (trade name, manufactured by Daicel Ornex Co., Ltd.). Among these, UN-953, UN-954, and H-219 are particularly preferable from the viewpoint of pattern formation and photosensitivity.
Further, as a commercially available product containing urethane methacrylate having a structural unit represented by the above general formula (1), for example, UN-6060PTM (number of functional groups: 2, Mw: 6,000, trade name, manufactured by Negami Kogyo Co., Ltd.) ) And other commercially available products. 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.

Further, as a commercially available product containing the urethane acrylate represented by the general formula (3), for example, UN-952 (number of functional groups: 10, Mw: 6,500 to 11,000) is represented by the general formula (6). Examples of the commercially available product containing the urethane acrylate represented include commercially available products such as UN-905 (number of functional groups: 15, Mw: 40,000 to 200,000) (all of the above are trade names, Negami Kogyo). Made by Co., Ltd.).
Among these, UN-952 is particularly preferable from the viewpoint of pattern formation and photosensitivity.

The total number of (meth) acryloyl groups (number of photopolymerizable functional groups) contained in the high molecular weight urethane (meth) acrylate is 2 to 30, 2 to 2 in one molecule from the viewpoint of improving pattern formation and heat resistance. It may be appropriately selected from 24, 2-20, 2-15, 4-12, 4-10, 8-15, 8-12, 15-24, or 18-22, and the physical properties of the obtained cured product. From the viewpoint of stabilizing the characteristics, 2 to 20, 2 to 10, or 6 to 20 may be appropriately selected.
When the number of photopolymerizable functional groups is 2 or more, it is possible to improve the pattern forming property, heat resistance, and rigidity of the cured product at high temperature. On the other hand, when the number of photopolymerizable functional groups is 30 or less, the rigidity of the cured product is improved and the adhesion to the substrate or the like is improved. Further, a resin composition having an appropriate viscosity can be obtained, the coatability is improved, and when the resin composition after coating is irradiated with light, only the surface portion is easily photocured rapidly and the inside is easily cured. Can suppress the phenomenon that photocuring does not proceed sufficiently, and excellent resolution can be obtained. Therefore, excellent pattern formability can be obtained even when a thick photosensitive layer is formed. Further, after at least one of photo-curing and thermosetting is performed, the residual unreacted (meth) acryloyl group can be further reduced, and fluctuations in the physical properties and properties of the obtained cured product can be further suppressed.

The weight average molecular weight of the high molecular weight body is 2,000 or more, and may be 2,500 or more, or 3,000 or more, from the viewpoint of improving the coatability and resolution of the resin composition. Further, from the viewpoint of improving developability and compatibility, the number may be 3,500 or more. 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 further improving the developability and compatibility. From the viewpoint of, it may be 20,000 or less.
When the weight average molecular weight is 2,000 or more, when it is applied on a substrate, the generation of dripping of the applied composition can be suppressed, so that excellent film formability can be obtained. In addition, it is possible to easily form a thick photosensitive layer, and it is possible to suppress the problem that the stress of the resin due to curing shrinkage increases and the reliability decreases.
On the other hand, when the weight average molecular weight is 40,000 or less, the coatability is improved, a thick photosensitive layer is easily formed, and the pattern formability is improved. In addition, since the solubility in a developing solution is also good, excellent resolution can be exhibited. Further, the transparency of the cured product is improved, and a cured product having an excellent transmittance required as a transparent material can be obtained.

(Low molecular weight material having photopolymerizable functional group and urethane bond)
By "low molecular weight" is meant a compound having a weight average molecular weight of less than 2,000.
Examples of the photopolymerizable functional group contained in the photopolymerizable functional group and the low molecular weight substance having a urethane bond (hereinafter, may be simply referred to as the low molecular weight substance) include a (meth) acryloyl group; a vinyl group and an allyl. Examples thereof include ethylenically unsaturated groups such as alkenyl groups such as groups. The low molecular weight substance may be a low molecular weight substance having at least one photopolymerizable functional group, and from the viewpoint of improving pattern forming property, the low molecular weight substance is a (meth) acryloyl group as a photopolymerizable functional group. May have. From the viewpoint of improving the pattern forming property, the low molecular weight substance may have 2 to 6 photopolymerizable functional groups, may have 2 to 4 photopolymerizable functional groups, and may have 2 photopolymerizable functional groups. You may have one. Further, the low molecular weight substance may contain a low molecular weight substance having two or more (meth) acryloyl groups as a photopolymerizable functional group from the viewpoint of improving the pattern forming property, and 2 to 6 (meth) acryloyl groups may be contained. It may contain a low molecular weight body having a group, or it may contain a low molecular weight body having 2 to 4 (meth) acryloyl groups.
In the present specification, a low molecular weight substance having a (meth) acryloyl group as a photopolymerizable functional group may be simply referred to as "low molecular weight urethane (meth) acrylate".

Examples of the low molecular weight urethane (meth) acrylate include a reaction product of a (meth) acrylate having a hydroxyl group and an isocyanate compound having an isocyanate group. Here, examples of the (meth) acrylate having a hydroxyl group and the isocyanate compound include an acrylate having a hydroxyl group and an isocyanate compound exemplified as those used for producing a high molecular weight substance. Here, as an example of what is appropriately selected from the viewpoint of improving pattern formation and the like, the same one which is appropriately selected as being used for producing a high molecular weight body from the same viewpoint is exemplified.

As the low molecular weight urethane (meth) acrylate, a (meth) acrylate having a hydroxyl group is reacted with the terminal isocyanate group of the heavy adduct of the isocyanate compound having at least two isocyanate groups in one molecule and the diol compound. Examples thereof include the reaction products produced. Here, as the isocyanate compound having at least two isocyanate groups in one molecule, the diol compound, and the (meth) acrylate having a hydroxyl group, each of them has an isocyanate group in one molecule exemplified as being used for producing a high molecular weight substance. Examples thereof include an isocyanate compound having at least two of them, a diol compound, and a (meth) acrylate having a hydroxyl group. Here, as an example of what is appropriately selected from the viewpoint of improving pattern formation and the like, the same one which is appropriately selected as being used for producing a high molecular weight body from the same viewpoint is exemplified.
Examples of this reaction product include those having a structural unit represented by the following general formula (7).

In the general formula (7), X ₂ represents a divalent organic group having a chain hydrocarbon skeleton, an alicyclic skeleton, or an aromatic ring skeleton, and Y ₂ represents a chain hydrocarbon skeleton or an alicyclic skeleton. Indicates a divalent organic group having. That is, examples of the low molecular weight body include those having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton, an alicyclic skeleton, and an aromatic ring skeleton. Examples of X ₂ and Y ₂ are the same as those of X ₁ and Y ₁ in the general formula (1), respectively.
From the viewpoint of improving the pattern forming property and improving the transparency, water resistance, and moisture resistance of the resin composition in a well-balanced manner, X ₂ is a divalent organic group having a chain hydrocarbon skeleton, which is branched. It may be appropriately selected from a divalent organic group having a chain hydrocarbon skeleton, a branched alkylene group having 2 to 12 carbon atoms, for example, a residue of the above aliphatic diisocyanate compound. From the same viewpoint, Y ₂ may be appropriately selected from the residues of a divalent organic group having an alicyclic skeleton, for example, the diol compound having the alicyclic skeleton.

Specific examples of the low molecular weight urethane (meth) acrylate include urethane acrylate represented by the following general formula (8).

In the above chemical formula (8), n ₅ represents an integer of 1 to 4. R ¹³ and R ¹⁴ are independent hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, and a plurality of R ¹³ and R ¹⁴ are alkyl groups having at least 3 carbon atoms of 1 to 4 carbon atoms, respectively. ..
Among the urethane acrylates represented by the chemical formula (8), X ₂ of the general formula (7) is a residue of trimethylhexamethylene diisocyanate which is a divalent organic group having a chain hydrocarbon skeleton, and Y ₂ As a commercial product containing urethane acrylate having a structural unit which is a residue of cyclohexanedimethanol of a divalent organic group having an alicyclic skeleton, for example, TMCH-5R (trade name, number of functional groups: 2, Mw) : 950, manufactured by Hitachi Kasei Co., Ltd.) and other commercially available products.
Further, as commercially available products containing urethane (meth) acrylate having a structural unit represented by the above general formula (7), KRM8452 (number of functional groups: 10, Mw: 1,200, manufactured by Daicel Ornex Co., Ltd.), UN Examples thereof include commercially available products such as -3320HA (number of functional groups: 6, Mw: 1,500, manufactured by Negami Kogyo Co., Ltd.) and UN-3320HC (number of functional groups: 6, Mw: 1,500, manufactured by Negami Kogyo Co., Ltd.). In the above description, the number of functional groups and Mw in parentheses are the total number of (meth) acryloyl groups and the weight average molecular weight contained in the urethane (meth) acrylate, respectively.

The weight average molecular weight of the low molecular weight body is less than 2,000, may be 1,800 or less from the viewpoint of improving adhesion, and is 1,600 or less from the viewpoint of improving resolution. It may be 1,000 or less. On the other hand, the lower limit of the weight average molecular weight may be 500 or more, or 700 or more, from the viewpoint of film formability, although it can be appropriately used according to a desired purpose.

The content of the component (A) is 10% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass based on the total solid content of the photosensitive resin composition. As described above, it may be appropriately selected from 80% by mass or more or 90% by mass or more. When the content is 10% by mass or more, the coatability is improved, and excellent pattern forming property can be obtained even when a thick photosensitive layer is formed.
Considering the pattern-forming property and coatability of the obtained resin composition, and the physical properties and properties required for the cured product of the resin composition, the upper limit of the content of the component (A) is not particularly limited, but the photosensitive resin Based on the total solid content of the composition, it can be appropriately selected from 100% by mass or less, 99% by mass or less, 95% by mass or less, 85% by mass or less, or 80% by mass or less.
The lower limit value and the upper limit value of the content of the component (A) can be appropriately combined while maintaining consistency.
Further, for example, when the component (A) contains two kinds of high molecular weight substances, the content ratio thereof is not particularly limited, but the mass ratio can be 20/80 to 80/20. When the component (A) contains two kinds of low molecular weight bodies, the content ratio thereof is not particularly limited, but the mass ratio can be 20/80 to 80/20. When the component (A) contains both a high molecular weight substance and a low molecular weight substance, the content ratio thereof (total amount of the high molecular weight substance / total amount of the low molecular weight substance) is not particularly limited, but the mass ratio is 100/20. It can be ~ 100/80, and it can also be 100/30 ~ 100/70.

<Component (B): Photopolymerization initiator>
The photosensitive resin composition of the present embodiment contains the following specific photopolymerization initiator as the component (B).
That is, from the viewpoint of improving the pattern forming property, the component (B) is at least [I] acylphosphine oxide-based photopolymerization initiator, aromatic ketone-based photopolymerization initiator, quinone-based photopolymerization initiator, and alkylphenone-based component. It contains at least one photopolymerization initiator selected from the group consisting of a photopolymerization initiator, an acridin-based photopolymerization initiator, a phenylglycine-based photopolymerization initiator, and a coumarin-based photopolymerization initiator, or [ II] Contains a photopolymerization initiator having a molar extinction coefficient of 2,000 L / mol · cm or less. Here, the molar extinction coefficient is a value measured according to the method described in Examples.
Among the above [I], from the viewpoint of improving the pattern forming property, it is preferable to contain a photopolymerization initiator selected from the group consisting of an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator. Further, in the above [II], from the viewpoint of improving the pattern forming property, the molar extinction coefficient may be 1,500 L / mol · cm or less, or 1,000 L / mol · cm or less. It may be 500 L / mol · cm or less, 200 L / mol · cm or less, 100 L / mol · cm or less, 50 L / mol · cm or less, 30 L / mol / cm or less. It may be mol · cm or less.
Hereinafter, each photopolymerization initiator will be described in order.

The acylphosphine oxide-based photopolymerization initiator has an acylphosphine oxide group [> P (= O) -C (= O) -R], and is, for example, (2,6-dimethoxybenzoyl) -2,4. , 6-Pentylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide ("IRGACURE-TPO" (BASF)), ethyl-2 , 4,6-trimethylbenzoylphenylphosphinate, bis (2,4,6-trimethylbenzoyl) -phenylphosphenyl oxide ("IRGACURE-819" (manufactured by BASF)), (2,5-dihydroxyphenyl) diphenylphosphine Examples thereof include oxides, (p-hydroxyphenyl) diphenylphosphine oxide, bis (p-hydroxyphenyl) phenylphosphine oxide, tris (p-hydroxyphenyl) phosphine oxide and the like.

Examples of the aromatic ketone photopolymerization initiator include benzophenone, N, N'-tetramethyl-4,4'-diaminobenzophenone (Michler ketone), N, N'-tetraethyl-4,4'-diaminobenzophenone, 4 -Methyl-4'-dimethylaminobenzophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one ("IRGACURE-651" (manufactured by BASF)), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one ("IRGACURE-369" (manufactured by BASF)), 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propane-1-one ("IRGACURE-907" (manufactured by BASF)) and the like.

Examples of the quinone-based photopolymerization initiator include 2-ethylanthraquinone, phenanthrenquinone, 2-t-butyl anthraquinone, octamethyl anthraquinone, 1,2-benz anthraquinone, 2,3-benz anthraquinone, 2-phenylanthraquinone, and 2 , 3-Diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 2-methyl-1,4-naphthoquinone, 2,3-dimethylanthraquinone, etc. Be done.

Examples of the alkylphenone-based photopolymerization initiator include benzoin-based compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin phenyl ether, and 2,2-dimethoxy-1,2-diphenylethane-1-. On ("IRGACURE-651" (manufactured by BASF)), 1-hydroxy-cyclohexyl-phenyl-ketone ("IRGACURE-184" (manufactured by BASF)), 2-hydroxy-2-methyl-1-phenyl-propane- 1-one ("IRGACURE-1173" (manufactured by BASF)), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propane-1-one ("IRGACURE-") 2959 ”(manufactured by BASF)), 2-Hirodoxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methyl-propan-1-one (“IRGACURE) -127 "(manufactured by BASF)) and the like.

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

Examples of the phenylglycine-based photopolymerization initiator include N-phenylglycine, N-methyl-N-phenylglycine, N-ethyl-N-phenylglycine and the like.

Examples of the coumarin-based photopolymerization initiator include 7-amino-4-methylcoumarin, 7-dimethylamino-4-methylcoumarin, 7-diethylamino-4-methylcoumarin, and 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, 4,6-dimethyl-7-diethylaminocoumarin, 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] Kinolidine 12 (9H) -one, 7-diethylamino-5', 7'-dimethoxy-3,3'-carbonylbiscoumarin, 3,3'-carbonylbis [7- (diethylamino) coumarin], 7-diethylamino -3-Chienoki silk coumarin and the like.

Among these (B) photopolymerization initiators, a compound represented by the following general formula (B1) may be used as the acylphosphine oxide-based photopolymerization initiator from the viewpoint of improving the pattern forming property. Further, as the alkylphenon-based photopolymerization initiator, a compound represented by the following general formula (B2) may be used. Further, as the photopolymerization initiator satisfying the molar extinction coefficient, a compound represented by the following general formula (B1) or (B2) may be used.

( ^RB1 , R ^B2 and R ^B3 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and R ^B4 and R ^B5 independently represent each. hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms. ^R B1 ^{to R B5} other than a hydrogen atom, each have a substituent May be.)

( ^RB6 represents a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or an amino group, and ^RB7 and ^RB8 are independently hydrogen atoms, an alkyl group having 1 to 8 carbon atoms, and 6 to 12 carbon atoms, respectively. R ^B7 and R ^B8 may be bonded to each other to form a cyclic structure having 3 to 16 carbon atoms. Other than the hydroxyl group and the hydrogen atom. Each of R ^{B6 to} R ^B8 may have a substituent, and the amino groups having a substituent may form a cyclic structure having 3 to 12 carbon atoms by bonding the substituents to each other. ..
Each ^RB9 is an organic having 1 to 10 carbon atoms which may independently contain one or more selected from hydrogen atom, halogen atom, hydroxyl group, amino group, mercapto group, or oxygen atom, nitrogen atom and sulfur atom. Indicates a group. )

In the general formula (B1), ^RB1 , ^RB2 and ^RB3 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
Alkyl group having 1 to 6 carbon atoms which R ^{B1, R B2} and ^{R B3} represents may be an alkyl group having 1 to 3 carbon atoms may be an alkyl group having 1 or 2 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-heptyl group, an n-hexyl group and the like.
The alkoxy group having 1 to 6 carbon atoms represented by R ^B1 , R ^B2 and R ^B3 may be an alkoxy group having 1 to 3 carbon atoms or an alkoxy group having 1 or 2 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, an n-butoxy group, a tert-butoxy group and the like.
Among these groups, ^RB1 , ^RB2 and ^RB3 may be methyl groups from the viewpoint of improving pattern formation.

In the general formula (B1), ^RB4 and ^RB5 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms. ..
Alkyl and alkoxy groups having 1 to 6 carbon atoms having 1 to 6 carbon atoms which R ^B4 and ^{R B5} represents ^is described as in the case of R ^{B1, R B2} and ^{R B3.}
The aryl group having 6 to 12 carbon atoms represented by R ^B4 and R ^B5 may be an aryl group having 6 to 10 carbon atoms or an aryl group having 6 to 8 carbon atoms. Examples of the aryl group include a phenyl group and a naphthyl group.

The R ^B1 to R ^B5 is the substituent which may have, for example, a halogen atom, a carboxyl group, hydroxy group, an amino group, a mercapto group, an alkyl group having 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms Examples thereof include a group and an aryl group having 6 to 12 carbon atoms. R ^B1 to R ^B5 is a substituent which may have an alkyl group, an alkoxy group and aryl group, an alkyl group described as R ^B1 to R ^B5, are the same as those of the alkoxy group and an aryl group ..

In the general formula (B2), ^RB6 represents a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or an amino group.
The alkoxy group represented by R ^B6 is described in the same manner as in the case of R ^B1 , R ^B2 and R ^B 3 in the general formula (B1).
Among these groups, R ^B6, from the viewpoint of improving the pattern formability may be a hydroxyl group.

In the general formula (B2), ^RB7 and ^RB8 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an aryl group having 6 to 12 carbon atoms. ..
Alkyl groups R ^B7 and ^{R B8} represents an alkoxy group and aryl group, the general formula (B1) in the alkyl group represented by ^R B1 ^{to R B5,} are the same as those of the alkoxy group and aryl group.
R ^B7 and R ^B8 may be bonded to each other to form a cyclic structure having 3 to 16 carbon atoms.
The cyclic structure may be a cyclic structure having 4 to 10 carbon atoms or a cyclic structure having 5 to 8 carbon atoms.
The cyclic structure may be an alicyclic structure from the viewpoint of improving the pattern forming property, and examples of the alicyclic structure include a cyclopentane structure, a cyclohexane structure, a cycloheptane structure, and a cyclooctane structure. In addition, these alicyclic structures may contain carbon atoms to which R ^B7 and R ^B8 are directly bonded together.

The substituents that R ^{B6 to} R ^B8 can have will be described in the same manner as the substituents that R ^{B1 to} R ^B5 may have in the general formula (B1).
However, the amino group having a substituent may form a cyclic structure having 3 to 12 carbon atoms by bonding the substituents to each other.
The cyclic structure formed by the substituent of the amino group may be a cyclic structure having 3 to 10 carbon atoms or a cyclic structure having 3 to 5 carbon atoms.
The cyclic structure may be a 5 to 10-membered ring containing a nitrogen atom of an amino group, a 5 to 7-membered ring containing a nitrogen atom of an amino group, or a 6-membered ring containing a nitrogen atom of an amino group. It may be a ring. Furthermore, these cyclic structures may contain heteroatoms other than nitrogen atoms such as oxygen atoms. Specific examples of the cyclic structure formed by the substituent of the amino group include a structure (morpholino group) represented by the following formula (B3).

In the general formula (B2), ^RB9 may independently contain one or more selected from hydrogen atom, halogen atom, hydroxyl group, amino group, mercapto group, or oxygen atom, nitrogen atom and sulfur atom. It shows an organic group having 1 to 10 carbon atoms.
The organic group having 1 to 10 carbon atoms represented by ^RB9 may be an organic group having 1 to 6 carbon atoms or an organic group having 1 to 4 carbon atoms.
The organic group having 1 to 10 carbon atoms represented by ^RB9 may be a hydrocarbon group such as an alkyl group, an alkenyl group or an aryl group. These alkyl group, the alkenyl group and an aryl group, an alkyl group represented by R ^B1 to R ^B5 in the formula (B1), those similar to the alkenyl group and aryl group.
Examples of the organic group having 1 to 10 carbon atoms containing an oxygen atom represented by ^RB9 include an alkoxy group having 1 to 10 carbon atoms.
Examples of the organic group having 1 to 10 carbon atoms containing a nitrogen atom represented by ^RB9 include a group represented by the general formula (B3).
Examples of the organic group having 1 to 10 carbon atoms containing a sulfur atom represented by ^RB9 include an alkylthio group such as a methylthio group.

Examples of the photopolymerization initiator having a molar extinction coefficient of 2,000 L / mol · cm or less include "IRGACURE-819" (molar extinction coefficient:: bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide. 965 L / mol · cm, manufactured by BASF, trade name), "IRGACURE-TPO", 2,4,6-trimethylbenzoyldiphenylphosphine oxide (molar extinction coefficient: 164 L / mol · cm, manufactured by BASF, trade name) , 1-Hydroxy-cyclohexyl-phenyl-ketone "IRGACURE-184" (molar extinction coefficient: 18 L / mol · cm, manufactured by BASF, trade name) and the like, but are not particularly limited thereto. ..

The content of the component (B) is such that the absorbance of the photosensitive layer formed by the photosensitive resin composition (thickness after drying) of 50 μm with respect to light having a wavelength of 365 nm is 0.35 or less, 0.3 or less. It may be appropriately selected from an amount of 0.2 or less, or an amount of 0.1 or less. With the above content, for example, even when a pattern is formed by a thick photosensitive layer of 70 μm or more, light can easily pass to the bottom of the photosensitive layer (the surface of the photosensitive layer on the substrate side), so that the pattern is formed. The sex can be improved. Here, the absorbance can be adjusted to a wavelength of 365 nm by using, for example, an ultraviolet-visible spectrophotometer (product name: “U-3310 Spectrophotometer”, manufactured by Hitachi High-Technologies Corporation) and using a polyethylene terephthalate film alone as a reference. The absorbance for light can be measured. The absorbance of the photosensitive layer against light having a wavelength of 365 nm when the thickness is 50 μm can be obtained by converting the absorbance measured for the photosensitive layer having a thickness other than 50 μm into the absorbance having a thickness of 50 μm based on Lambertbert's law. it can.

The content of the component (B) may be appropriately determined based on the absorbance at a thickness of the photosensitive layer of 50 μm, and is usually 0.05 to 20% by mass or 0.05 to 20% by mass based on the total solid content of the photosensitive resin composition. It may be appropriately selected from 10% by mass, 0.1% by mass, 0.1 to 5% by mass, or 0.1 to 3% by mass. By setting the content as described above, the sensitivity of the photosensitive resin composition can be improved, the deterioration of the resist shape can be suppressed, and the pattern forming property can be improved.

As the component (B), in addition to the photopolymerization initiator, at least one selected from the group consisting of an oxime ester-based photopolymerization initiator and an imidazole-based photopolymerization initiator as long as the effects of the present invention are not impaired. It may contain a seed photopolymerization initiator.
The oxime ester-based photopolymerization initiator is a photopolymerization initiator having an oxime ester bond, and is, for example, 1,2-octanedione-1- [4- (phenylthio) phenyl] -2- (O-benzoyloxime) ( Product name: OXE-01, manufactured by BASF), 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] Ethanone 1- (O-acetyloxime) (trade name: OXE) -02, manufactured by BASF), 1-phenyl-1,2-propanedione-2- [O- (ethoxycarbonyl) oxime] (trade name: Quanture-PDO, manufactured by Nippon Kayaku Co., Ltd.) and the like.
Examples of the imidazole-based photopolymerization initiator as a 2,4,5-triarylimidazole dimer include 2- (2-chlorophenyl) -1- [2- (2-chlorophenyl) -4,5-diphenyl. -1,3-Diazole-2-yl] -4,5-diphenylimidazole and other 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 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 and the like can be mentioned.
In this case, the content of at least one photopolymerization initiator selected from the group consisting of the oxime ester-based photopolymerization initiator and the imidazole-based photopolymerization initiator is preferably 20 with respect to the total amount of the component (B). It is mass% or less, more preferably 10 mass% or less, still more preferably 5 mass% or less. Further, the content of at least one photopolymerization initiator selected from the group consisting of the oxime ester-based photopolymerization initiator and the imidazole-based photopolymerization initiator is substantially included in the total amount of the component (B). It does not have to be, and more specifically, it is preferably 1% by mass or less, and more preferably 0% by mass.

In addition to the above component (B), N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine, triethanolamine, etc. (B') photopolymerization initiators such as secondary amines can also be used alone or in combination of two or more.

(Component (C): low molecular weight substance having an isocyanul ring or an alicyclic skeleton)
The "low molecular weight substance" of the component (C) means a compound having a weight average molecular weight of less than 2,000.
From the viewpoint of improving pattern formation, the photosensitive resin composition of the present embodiment can contain a low molecular weight substance having an isocyanul ring or an alicyclic skeleton as the component (C). The component (C) can be used alone or in combination of two or more. Even a low molecular weight substance having an isocyanul ring or an alicyclic skeleton is classified into the component (A) if it has a photopolymerizable functional group and a urethane bond.
The component (C) may have two or more photopolymerizable functional groups or two to five photopolymerizable functional groups from the viewpoint of improving the pattern forming property, and may have two or five photopolymerizable functional groups. It may have two or three sex functional groups, or it may have three.
Examples of the photopolymerizable functional group contained in the component (C) include an ethylenically unsaturated group such as a (meth) acryloyl group; an alkenyl group such as a vinyl group and an allyl group. From the viewpoint of improving the pattern forming property, the component (C) may contain a compound having a (meth) acryloyl group as a photopolymerizable functional group.
From the above, the component (C) may contain a low molecular weight substance having two or more (meth) acryloyl groups together with an isocyanul ring or an alicyclic skeleton.
Among the components (C), examples of the low molecular weight compound having an isocyanul ring include a compound represented by the following general formula (C1).

(In the general formula (C1), R ⁷ , R ⁸ and R ⁹ each independently represent an alkylene group having 1 to 6 carbon atoms, and R ¹⁰ and R ¹¹ each independently represent a hydrogen atom or a methyl group. R ¹² represents a hydrogen atom or a (meth) acryloyl group.)

In the general formula (C1), the alkylene group having 1 to 6 carbon atoms represented by R ⁷ , R ⁸ and R ⁹ may be an alkylene group having 1 to 4 carbon atoms, or an alkylene group having 1 to 3 carbon atoms. There may be.
Examples of the alkylene group having 1 to 6 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, an isopropylene group, an isobutylene group, a t-butylene group, a pentylene group, a hexylene group and the like. , It may be an ethylene group from the viewpoint of improving the pattern forming property.
In the general formula (C1), R ¹⁰ and R ¹¹ each independently represent a hydrogen atom or a methyl group, and may be a hydrogen atom from the viewpoint of improving pattern formation.
In the general formula (C1), R ¹² represents a hydrogen atom or a (meth) acryloyl group, and may be a (meth) acryloyl group from the viewpoint of improving pattern formation.

The compound represented by the general formula (C1) may be at least one selected from the group consisting of the compound represented by the following formula (C1-1) and the compound represented by the following formula (C1-2). Often, from the viewpoint of improving the pattern forming property, it may be a compound represented by the following formula (C1-1).

The weight average molecular weight of the low molecular weight substance having an isocyanul ring among the components (C) is less than 2,000, and from the viewpoint of improving pattern formation, 200 to 1,500, 300 to 1,000, or , 350-600 may be appropriately selected.

As the low molecular weight substance having an isocyanul ring, a commercially available product may be used. Examples of commercially available products include "A-9300" (compound represented by the above formula (C1-1)) manufactured by Shin-Nakamura Chemical Industry Co., Ltd. and "M-215" manufactured by Toagosei Co., Ltd. (the above formula (the above formula (C1-1)). Examples thereof include the compound) represented by C1-2).
The low molecular weight compound having an isocyanul ring can be used alone or in combination of two or more.

Among the components (C), the low molecular weight substance having an alicyclic skeleton is not particularly limited, and examples thereof include an alicyclic hydrocarbon skeleton having 5 to 20 carbon atoms. The alicyclic hydrocarbon skeleton is at least one selected from the group consisting of a cyclopentane skeleton, a cyclohexane skeleton, a cyclooctane skeleton, a cyclodecane skeleton, a norbornane skeleton, a dicyclopentane skeleton, and a tricyclodecane skeleton. May be good. Among these, a tricyclodecane skeleton may be used from the viewpoint of improving pattern formation.

Among the components (C), the weight average molecular weight of the low molecular weight substance having an alicyclic skeleton is less than 2,000, may be less than 1,500 from the viewpoint of improving adhesion, and has further resolution. It may be less than 1,000 or less than 500 from the viewpoint of improvement. On the other hand, the lower limit of the weight average molecular weight may be 150 or more, or 200 or more, from the viewpoint of film formability, although it can be appropriately used according to a desired purpose.
The low molecular weight substance having an alicyclic skeleton may be tricyclodecanedimethanol diacrylate from the viewpoint of pattern formation.
As the low molecular weight body having an alicyclic skeleton, a commercially available product may be used. Examples of commercially available products include A-DCP (tricyclodecanedimethanol diacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) and the like.
The low molecular weight compound having an alicyclic skeleton can be used alone or in combination of two or more.

When the photosensitive resin composition of the present embodiment contains the component (C), the content thereof is 3% by mass or more, 5% by mass or more, and 10% by mass based on the total solid content of the photosensitive resin composition. It may be appropriately selected from the above or 20% by mass or more. (C) Content of component is 1% by mass
With the above, excellent pattern forming property 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 as this, the upper limit of the content of the component (C) is appropriately from 70% by mass or less, 60% by mass or less, or 40% by mass or less based on the total solid content of the photosensitive resin composition. You can select it.

<Component (D): Silane compound>
Further, the photosensitive resin composition of the present embodiment can further contain the (D) silane compound. As the component (D), a known silane coupling agent can be used. The component (D) can improve the adhesiveness of the electronic component to the substrate, and in particular, when the substrate contains silicon (for example, a glass substrate, a silicon wafer, an epoxy resin impregnated glass cloth substrate, etc.). Is valid. Examples of the silane coupling agent include alkoxysilanes such as methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane; (meth) acryloxypropyltrimethoxysilane, and (meth) acryloxipropylmethyldimethoxysilane. (Meta) acryloyl group-containing alkoxysilanes such as: γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-triethoxysilyl-N- (1, 3-Dimethylbutylidene) Amine-based alkoxysilanes such as propylamine; γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, glycidoxypropylmethyldiethoxysilane, glycidoxypropylmethyldi Glycydoxy group-containing alkoxysilane such as isopropenoxysilane; alicyclic epoxy group-containing alkoxysilane such as 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; ureido group-containing alkoxy such as 3-ureidopropyltriethoxysilane Silane; mercapto group-containing alkoxysilanes such as 3-mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane; carbamate group-containing alkoxysilanes such as triethoxysilylpropylethylcarbamate; 3- (triethoxysilyl) propylsuccinate anhydride Examples thereof include alkoxysilane containing a polybasic acid anhydride group. These can be used alone or in combination of two or more.
From the viewpoint of further improving adhesiveness, (meth) acryloyl group-containing alkoxysilanes such as (meth) acryloxypropyltrimethoxysilane and (meth) acryloxypropylmethyldimethoxysilane, glycidoxypropyltrimethoxysilane, and glycidoxy A silane coupling agent having an ethylenically unsaturated group in the molecule, such as a glycidoxy group-containing alkoxysilane such as propylmethyldiethoxysilane and glycidoxypropylmethyldiisopropenoxysilane, may be used.

When the photosensitive resin composition of the present embodiment contains the component (D), the content thereof is 0.05 to 15% by mass, 0.1 to 10 based on the total solid content of the photosensitive resin composition. It may be appropriately selected from mass%, 0.1 to 7 mass%, 1 to 7 mass%, or 1 to 5 mass%. By setting the content as described above, deterioration of the resist shape can be suppressed and pattern forming property can be improved.

<Component (E): Thermal radical polymerization initiator>
In addition, the photosensitive resin composition of the present embodiment can further contain (E) a thermal radical polymerization initiator. The component (E) is not particularly limited, and for example, α, α'-bis (t-butylperoxy) diisopropylbenzene, dicumylperoxide, t-butylcumylperoxide, di-t-butylperoxide and the like. Dialkyl peroxides; ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide; 1,1-bis (t-butylperoxy) cyclohexane, 1,1-bis (t-butylperoxy)- 2-Methylcyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) cyclohexane, 1,1-bis (t-hexyl) Peroxy) -3,3,5-Peroxyketal such as trimethylcyclohexane; Hydroperoxide such as p-menthanhydroperoxide; Diacylper such as octanoyl peroxide, lauroyl peroxide, stearyl peroxide, benzoyl peroxide, etc. Oxide: Peroxy such as bis (4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethylperoxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-3-methoxybutylperoxydicarbonate, etc. Carbonate; t-butylperoxypivalate, t-hexylperoxypivalate, 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-hexylper Oxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurylate, t-butylperoxyisopropylmonocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate , T-Butylperoxybenzoate, t-Hexylperoxybenzoate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, peroxides such as peroxyesters such as t-butylperoxyacetate Polymerization initiator, 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2' Examples thereof include azo-based polymerization initiators such as −azobis (4-methoxy-2'-dimethylvaleronitrile).

As the component (E), a peroxide-based polymerization initiator, a dialkyl peroxide-based polymerization initiator, and particularly dicumyl peroxide can be selected from the viewpoint of improving the pattern forming property. In addition, the component (E) can be used alone or in combination of two or more.

When the component (E) is contained, the content thereof is 0.1 to 10% by mass, 0.2 to 5% by mass, or 0.3 to 1% based on the total solid content of the photosensitive resin composition. It may be appropriately selected from 5% by mass. By setting the content as described above, the heat resistance of the photosensitive resin composition is improved, and the reliability when used as a permanent film is improved.

<(F) component: inorganic filler>
The photosensitive resin composition of the present embodiment may contain the component (F) for the purpose of further improving various properties such as adhesiveness between the photosensitive resin composition and the substrate, heat resistance, and rigidity of the cured product. it can.
Examples of the component (F) include silica (SiO ₂ ), alumina (Al ₂ O ₃ ), titania (TIO ₂ ), tantalum oxide (Ta ₂ O ₅ ), zirconia (ZrO ₂ ), and 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 ), titanium Lead Acid Acid (PbO · TiO ₂ ), Lead Zirconate Titanium (PZT), Lead Zirconate Titanium (PLZT), Gallium Oxide (Ga ₂ O ₃ ), Spinel (MgO · Al ₂ O ₃ ), Murite (3Al) ₂ O ₃ · 2SiO _2), cordierite _{(2MgO · 2Al 2 O 3 ·} 5SiO 2), talc _{(3MgO · 4SiO 2 · H 2} O), aluminum titanate _{(TiO 2 · Al 2 O 3} ), yttria-containing Zirconia (Y ₂ O ₃ · ZrO ₂ ), barium silicate (BaO · 8SiO ₂ ), boron nitride (BN), calcium carbonate (CaCO ₃ ), barium sulfate (BaSO ₄ ), calcium sulfate (CaSO ₄ ), zinc oxide (ZnO), magnesium titanate (MgO · TiO ₂ ), hydrotalcite, mica, calcined kaolin, carbon (C) and the like can be used. These inorganic fillers can be used alone or in combination of two or more.

The average particle size of the component (F) is appropriately selected from 0.01 to 3 μm, 0.01 to 2 μm, or 0.02 to 1 μm from the viewpoint of improving adhesiveness, heat resistance, and rigidity of the cured product. Just do it. Here, the average particle size of the component (F) is the average particle size of the inorganic filler dispersed in the photosensitive resin composition, and is a value obtained by measuring as follows. First, the photosensitive resin composition is diluted (or dissolved) 1000 times with methyl ethyl ketone, and then conformed to the international standard ISO13321 using a submicron particle analyzer (manufactured by Beckman Coulter, Inc., trade name: N5). Then, the particles dispersed in the solvent are measured at a refractive index of 1.38, and the particle size at an integrated value of 50% (volume basis) in the particle size distribution is taken as the average particle size. Further, the component (F) contained in the photosensitive layer or the cured film of the photosensitive resin composition provided on the carrier film is also diluted (or dissolved) 1000 times (volume ratio) with a solvent as described above. After that, it can be measured by using the above-mentioned submicron particle analyzer.

The content of the component (F) may be appropriately selected from 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 is 0. It may be appropriately selected from more than% by mass, and may be 0% by mass (that is, it may not be included). As described above, by substantially not containing the component (F), the permeability of the photosensitive resin composition is improved, and for example, even when a pattern is formed by a thick photosensitive layer of 70 μm or more, the photosensitive layer is formed. Since light can easily pass through to the bottom of the photosensitive layer (the surface of the photosensitive layer on the substrate side), the pattern forming property is improved.

<Other additives>
The photosensitive resin composition of the present embodiment further contains additives such as a sensitizer, a heat-resistant high molecular weight substance, a heat-crosslinking agent, and an adhesion aid other than the component (D), if necessary. Can be done.

Examples of the sensitizer include sensitizers such as pyrazolines, anthracenes, xanthones, oxazoles, benzoxazoles, thiazoles, benzothiazoles, triazoles, stillbens, triazines, thiophenes and naphthalimides. Agents can be mentioned. These can be used alone or in combination of two or more.

Examples of the heat-resistant high molecular weight material include polyoxazole and its precursors, novolak resins such as phenol novolac and cresol novolak, and polyamides, which have high heat resistance and are used as engineering plastics from the viewpoint of improving processability. Examples thereof include imide and polyamide. These can be used alone or in combination of two or more.

From the viewpoint of improving the rigidity of the cured product, the thermal cross-linking agent includes, for example, an epoxy resin, a phenol resin in which the α-position is substituted with a methylol group and an alkoxymethyl group, and a group consisting of a methylol group and an alkoxymethyl group at the N-position. Examples thereof include a melamine resin and a urea resin substituted with at least one selected. 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 does not impair the effect of the photosensitive resin composition of the present embodiment, and is, for example, 0 based on the total solid content of the photosensitive resin composition. .1 to 10% by mass, 0.3 to 5% by mass, or 0.5 to 5% by mass may be appropriately selected.

<Diluent>
A diluent can be used in the photosensitive resin composition of the present embodiment, if necessary. Examples of the diluent 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; dimethyl. Sulfur atom-containing substances such as sulfoxide and sulfolane; esters such as γ-butyrolactone and dimethyl carbonate; cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate. , Esters such as propylene glycol monoethyl ether acetate, and other polar solvents. 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 such that the total solid content in the photosensitive resin composition is 50 to 90% by mass, 60 to 80% by mass, or 65 to 75% by 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% by mass, 20 to 40% by mass, or 25 to 35% by mass. By setting the amount of the diluent used within the above range, the coatability of the photosensitive resin composition is improved, and a higher-definition pattern can be formed.
Further, for example, when forming a photosensitive layer having a thickness of 70 μm or more, the viscosity of the photosensitive resin composition at 25 ° C. is 0.5 to 20 Pa · s, or 0.5 to 20 Pa · s, in consideration of the ease of forming the photosensitive layer. The amount can be 1 to 10 Pa · s.

The photosensitive resin composition of the present embodiment contains the above-mentioned components (A) and (B), as well as components (C) to (F), other additives, and a diluent used as desired. It can be obtained by uniformly kneading and mixing with a roll mill, a bead mill or the like.

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

The absorbance of the photosensitive layer formed by the photosensitive resin composition of the present embodiment with respect to light having a wavelength of 365 nm at a thickness (thickness after drying) of 50 μm is 0.35 or less, 0.3 or less, 0.2 or less, or. It can be appropriately selected from 0.1 or less. When the absorbance of the photosensitive layer at a thickness of 50 μm is 0.35 or less, for example, even when a pattern is formed by a thick photosensitive layer of 70 μm or more, the bottom of the photosensitive layer (on the substrate side of the photosensitive layer). Since the light can easily pass to the surface), the pattern forming property can be improved.

[Photosensitive resin film]
The photosensitive resin film of the present embodiment has a photosensitive layer using the photosensitive resin composition of the present embodiment. The photosensitive resin film of the present embodiment may have a carrier film. In the present specification, the term "layer" includes not only a structure having a shape formed on the entire surface but also a structure having a shape partially formed when observed as a plan view.

In the photosensitive resin film of the present embodiment, for example, the photosensitive resin composition of the present embodiment is applied onto a carrier film by the above-mentioned various coating methods to form a coating film, and the coating film is dried. , A photosensitive layer can be formed and manufactured. Further, when the photosensitive resin composition of the present embodiment contains a diluent, at least a part of the diluent may be removed at the time of drying.

For drying the coating film, a dryer using hot air drying, far infrared rays, or near infrared rays can be used, and the drying temperature is from 60 to 120 ° C., 70 to 110 ° C., or 90 to 110 ° C. It may be selected as appropriate. The drying time may be appropriately selected from 1 to 60 minutes, 2 to 30 minutes, or 5 to 20 minutes. When dried under the above conditions, when the photosensitive resin composition of the present embodiment contains a diluent, at least a part of the diluent can be removed.

Examples of the carrier film include a polyester resin film such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polyethylene naphthalate (PEN), and a resin film such as a polyolefin resin film such as polypropylene and polyethylene. A polyester resin film may be selected from the viewpoint of improving the mechanical strength and heat resistance of the photosensitive resin film.
The thickness of the carrier film may be appropriately selected from 10 μm to 3 mm or 10 to 200 μm in consideration of handleability 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 it to 30 μm or more, for example, when forming a photosensitive layer having a thickness of 150 μm or more, the number of operations by laminating or the like can be further reduced, and by setting it to 100 μm or less, a photosensitive resin film is wound. When wound around the core, the deformation of the photosensitive layer due to the stress difference between the inside and the outside of the core can be further reduced. Considering the effect of the photosensitive resin composition of the present embodiment that excellent pattern forming property can be obtained even when a thick photosensitive layer is formed, the thickness may be 70 μm or more, and the thickness may exceed 100 μm. There may be. The photosensitive layer having a thickness of 70 μm or more can be formed 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 carrier film. A photosensitive resin film having a thick photosensitive layer and a protective layer in this order can be obtained.

Further, in the photosensitive resin film of the present embodiment, a protective layer can be laminated on the surface of the photosensitive layer opposite to the surface in contact with the carrier film. As the protective layer, for example, a resin film such as polyethylene or polypropylene may be used. Further, the same resin film as the above-mentioned carrier film may be used, or a different resin film may be used.

[Manufacturing method of cured product]
The method for producing a cured product of the present embodiment includes a step of providing a photosensitive layer on a substrate using the photosensitive resin composition of the present embodiment or a photosensitive resin film (photosensitive layer forming step), and at least one of the photosensitive layers. A step of irradiating the portion with active light to form a photocurable portion (exposure step) and a step of removing at least a part of the photosensitive layer other than the photocurable portion to form a resin pattern (removal step). Have in order. Further, if desired, the resin pattern is further heat-treated (heating step). According to the method for producing a cured product of the present embodiment, a desired pattern can be formed, and even when a thick photosensitive layer of 70 μm or more is formed, the photosensitive layer of the present embodiment has excellent pattern forming properties. Taking advantage of the characteristics of the sex resin composition, for example, a desired pattern can be formed by a thick cured product having a thickness of 70 μm or more. In the present specification, the term "process" is used not only as an independent process but also as a "process" if the desired action of the process is achieved even when it cannot be clearly distinguished from other processes. include.

(Photosensitive layer forming process)
In the formation of the photosensitive layer, the photosensitive layer can be formed by applying or laminating the photosensitive resin composition or the photosensitive resin film of the present embodiment on the substrate, respectively.
Examples of the substrate include a glass substrate, a silicon wafer, a metal oxide insulator such as TiO ₂ and SiO ₂ , a silicon nitride, a ceramic piezoelectric substrate, an epoxy resin impregnated glass cloth substrate, and the like.

When the photosensitive resin composition is applied to the substrate to form a photosensitive layer, the photosensitive resin composition dissolved in the above-mentioned diluent in the form of a solution may be applied to the substrate, and may be applied as necessary. The coating film thus obtained may be dried. The coating and drying may be carried out by the various coating methods described for producing the above-mentioned photosensitive resin film and the method of drying the coating film.
When a photosensitive resin film is used, the photosensitive layer can be formed by a laminating 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 laminating method), the solid content concentration and viscosity of the photosensitive resin composition, etc., but is used as the lower limit of the thickness of the photosensitive layer after drying. It 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, 100 μm or more, 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 according to the application, and when used for electronic components or the like, 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 500 μm. Hereinafter, it may be appropriately selected from 300 μm or less or 250 μm or less.
In the method for producing a cured product of the present embodiment, since the photosensitive layer is formed by using the photosensitive resin composition of the present embodiment, it is possible to form a thick photosensitive layer. For example, when forming a photosensitive layer having a thickness of 150 μm or more, it is not formed by one coating (and drying if necessary) or by laminating, but is applied multiple times (and as necessary) until a desired thickness is obtained. Drying) or laminating may be repeated.

(Exposure process)
In the exposure step, at least a part of the photosensitive layer provided on the substrate in the photosensitive layer forming step is irradiated with active light as necessary, and the exposed portion is photocured to form a cured portion. When irradiating the active light beam, the photosensitive layer may be irradiated with the active light ray through a mask having a desired pattern, and an LDI (Laser Direct Imaging) exposure method, a DLP (Digital Light Processing) exposure method, or the like may be used. The active light may be irradiated by the direct drawing exposure method.
Further, from the viewpoint of improving the pattern forming property, post-exposure heating (PEB: Post exposure break) may be performed after exposure using a hot plate, a dryer or the like. The drying conditions are not particularly limited, but the drying 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.

Exposure amount of active ray ^{is, 10~2,000mJ / cm 2, 100~1,500mJ /} cm 2, or, may be suitably selected from 300~1,000mJ / cm ^2. Examples of the active light beam used include ultraviolet rays, visible light rays, electron beams, X-rays and the like. Further, as the light source, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a halogen lamp, or the like can be used.

(Removal process)
In the removing step, at least a part of the photosensitive layer formed in the exposure step other than the cured portion (unexposed portion) is removed to form a resin pattern. The unexposed portion may be removed by using, for example, a developing solution such as an organic solvent.
Examples of the organic solvent include ethanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, N-methylpyrrolidone and the like. Above all, cyclopentanone can be used from the viewpoint of development speed. These can be used alone or in combination of two or more.
In addition, various additives that can be usually used may be added to the organic solvent used as the developing solution.

After removing the unexposed portion with a developing solution, if necessary, wash (rinse) with water, alcohol such as methanol, ethanol, isopropyl alcohol, n-butyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether acetate, etc. You may.

(Heating process)
The heating step is a step adopted as necessary, and is a step of heat-treating the resin pattern formed in the removing step to form a cured product. The heat treatment is preferably carried out for 1 to 2 hours while selecting the heating temperature and gradually raising the temperature. The heating temperature may be appropriately selected from 120 to 240 ° C., 140 to 230 ° C., or 150 to 220 ° C. When the temperature is raised stepwise, for example, after heat treatment at at least one of around 120 ° C. and 160 ° C. for 10 to 50 minutes or 20 to 40 minutes, 30 to 100 at around 220 ° C. The heat treatment may be carried out for 1 minute or 50 to 70 minutes.

The thickness of the obtained resin pattern is the same as the thickness of the photosensitive layer after drying, and the lower limit is appropriately from 10 μm or more, 30 μm or more, 50 μm or more, 70 μm or more, 100 μm or more, 100 μm or more, or 150 μm or more. It may be selected, and the upper limit may be appropriately selected from 500 μm or less, 300 μm or less, or 250 μm or less. The thickness of the resin pattern may be appropriately selected from the above range according to the application, and when used for electronic parts or the like, 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 500 μm. Hereinafter, it may be appropriately selected from 300 μm or less and 250 μm or less.

[Laminate]
The laminate of the present embodiment includes a cured product of the photosensitive resin composition of the present embodiment, and for example, various types such as a substrate used in the above-mentioned method for producing a cured product, a carrier film of a photosensitive resin film, and the like. An example is one in which the cured product is provided on a support. The cured product of the photosensitive resin composition of the present embodiment can be formed, for example, by the above-mentioned method for producing the cured product of the present embodiment.

The thickness of the cured product in the laminate of the present embodiment 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, 100 μm or more, or 150 μm or more as the lower limit, and 500 μm or less and 300 μm as the upper limit. The following, or 250 μm or less may be appropriately selected. The thickness of the cured product may be appropriately selected from the above range according to the application, and when used for electronic parts or the like, 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 500 μm. Hereinafter, it may be appropriately selected from 300 μm or less and 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 the present embodiment, and excellent pattern forming property can be obtained even in a thick photosensitive layer of, for example, 70 μm or more. Therefore, for example, it is possible to respond to a request regarding an electronic circuit board that requires a thick cured product to be provided on a substrate in a finer pattern with the trend of miniaturization and high performance of electronic devices. .. Further, for example, in the plating treatment step in the manufacture of an electronic circuit board, by using the cured product formed by the photosensitive resin composition of the present embodiment as an insulating film, it is possible to suppress a decrease in yield due to a short circuit between wirings. it can.
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, for example.

Hereinafter, the purpose and advantages of the present embodiment will be described more specifically based on Examples and Comparative Examples, but the present embodiment is not limited to the following Examples. The method for measuring the weight average molecular weight of each component and the molar extinction coefficient of the photopolymerization initiator is as follows.

(Measurement of weight average molecular weight)
The weight average molecular weight was a value determined by standard polystyrene conversion by the GPC method using the following apparatus, and was measured using a solution of 0.5 mg of polymer in 1 mL of tetrahydrofuran (THF).
Device name: HLC-8320GPC manufactured by Tosoh Corporation
Columns: Gelpack R-420, R-430, and R-440 (three joints)
Detector: RI detector Column temperature: 40 ° C
Eluent: THF
Flow velocity: 1 ml / min Standard substance: Polystyrene

(Measurement of molar extinction coefficient of photopolymerization initiator)
1.0 mg of the photopolymerization initiator of the component (B) was precisely weighed in a 50 ml volumetric flask and dissolved in 10 ml of methanol precisely weighed with a whole pipette to prepare a solution.
Using an ultraviolet-visible spectrophotometer U-3010 (manufactured by JASCO Corporation), methanol was added to both the reference cell (made of quartz glass) and the sample cell (made of quartz glass) to perform baseline correction.
Then, the prepared solution was put into a sample cell, the absorption spectrum was measured, and the molar extinction coefficient was calculated from the Lanbert-Beer formula using the obtained absorbance (wavelength 365 nm) and the molar concentration of the solution.

(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 prepare a mixed solution. The above mixed solution was added to a 1 L autoclave equipped with a stirrer and a condenser while adding 1030 g of propylene glycol monomethyl ether acetate as a solvent and stirring. Then, the mixture was polymerized at 90 ° C. for 6 hours under a stirring rotation speed of 100 min ^-1 and a nitrogen atmosphere to obtain an acrylic resin (resin P-1) solution having a weight average molecular weight of 43,370.

(Examples 1 to 20, Comparative Examples 1 to 10)
The composition is blended according to the blending composition shown in Table 1 or 2 (the unit of the numerical value in the table is a mass part, and in the case of a solution, it is a solid content equivalent amount), kneaded with a three-roll mill, and the photosensitive resin. The composition was prepared. N, N-dimethylacetamide was added so that the solid content concentration became 60% by mass to obtain a photosensitive resin composition.

Next, using the photosensitive resin composition obtained above, each evaluation was carried out by the methods shown below. The evaluation results are shown in Tables 1 and 2.

[Preparation of photosensitive resin film]
A polyethylene terephthalate film having a thickness of 50 μm (manufactured by Teijin Limited, trade name: A-4100) is used as a carrier film, and the resin compositions of Examples and Comparative Examples are placed on the carrier film so that the thickness after drying is 50 μm. Was evenly applied to. Next, a photosensitive layer was formed by heating and drying at 100 ° C. for 15 minutes using a hot air convection dryer to prepare a photosensitive resin film having a carrier film and a photosensitive layer.

[Evaluation of pattern formation]
The direction in which the photosensitive layer of the photosensitive resin film is located on the glass epoxy substrate side (MCL-E-679F (trade name, manufactured by Hitachi Kasei Co., Ltd.) by etching copper). The carrier film was removed. Lamination was performed at 60 ° C. using a laminator. Next, the photosensitive resin film was re-laminated on the photosensitive layer by the above method, the carrier film was removed, and this was repeated three times to form the photosensitive layer and the carrier film having a thickness of 200 μm on the glass epoxy substrate. A laminate was obtained.
A resolution evaluation mask (line width: 5 μm, 8 μm, 10 μm, 15 μm, 20 μm, 25 μm, all line spaces are 200 μm) having the pattern shape shown in FIG. 1 is placed on the carrier film of the laminated body as an exposed portion. Further, an i-line filter (manufactured by Asahi Spectral Co., Ltd .: HB-0365) was placed and exposed using a high-precision parallel exposure machine (manufactured by Mikasa Co., Ltd.). At this time, the laminate is divided into three regions, and the three regions are light with different exposure amounts (600 mJ / cm ² , 1,000 mJ / cm ² , 1,400 mJ / cm ² ) and a wavelength of 365 nm (i-line). Exposed with. The exposed sample was heated after exposure for 1 minute on a hot plate at 90 ° C.
Then, the carrier film was removed and the film was immersed in a developing solution (cyclopentanone) for 20 minutes for development. The pattern after development was dried at room temperature for 30 minutes and observed with a metallurgical microscope to evaluate the pattern forming property. The evaluation was performed according to the following criteria. Here, "formable" means that the unexposed portion is cleanly removed and there is no defect such as tilting in the line portion (exposed portion). The evaluation results are shown in Tables 1 and 2.
A: It was possible to form with a line width of 5 to 10 μm.
B: It could not be formed with a line width of 5 to 10 μm, but it could be formed with a line width of 15 to 20 μm.
C: It could not be formed with a line width of 20 μm or less, or the photosensitive layer was peeled off after development.

[Measurement of absorbance]
With respect to the photosensitive resin film obtained in the above [Preparation of photosensitive resin film], the absorbance of the photosensitive layer with respect to light having a wavelength of 365 nm at a thickness of 50 μm (thickness after drying) was measured. 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). As a reference, a polyethylene terephthalate (PET) film alone was used. The measurement results are shown in Tables 1 and 2.

Details of each material in Tables 1 and 2 are as follows.
[(A) component / high molecular weight substance]
UN-952: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 10, weight average molecular weight: 9,000, reaction product of acrylate having a hydroxyl group and a diisocyanate compound, and an acryloyl group in the molecule. (Photopolymerizable functional group), urethane bond, chain hydrocarbon skeleton, and alicyclic hydrocarbon skeleton.)
-UN-954: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 6, weight average molecular weight: 4,500)
-UN-953: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 20, weight average molecular weight: 18,000)
H-219: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 9, weight average molecular weight: 36,000)
-UN-905: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 15, weight average molecular weight: 76,000)
-UN-904: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 10, weight average molecular weight: 4,300)
-UN-3320HS: Urethane acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 15, weight average molecular weight: 5,000)

[(A) component / low molecular weight substance]
TMCH-5R: Urethane acrylate (manufactured by Hitachi Kasei Co., Ltd., trade name, number of functional groups: 2, weight average molecular weight: 950, acryloyl group (photopolymerizable functional group) in the molecule, urethane bond, chain hydrocarbon skeleton, And a compound having an alicyclic hydrocarbon skeleton.)
-UN-3320HC: Urethane (meth) acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 6, weight average molecular weight: 1,500)
-UN-3320HA: Urethane (meth) acrylate (manufactured by Negami Kogyo Co., Ltd., trade name, number of functional groups: 6, weight average molecular weight: 1,500)

(For comparison; (A') component / high molecular weight substance)
-Resin P-1: Acrylic resin solution prepared in Synthesis Example 1 (weight average molecular weight: 43,370)
Z250: Cyclomer P (ACA) Z250 (manufactured by Daicel Ornex Co., Ltd., three structural units represented by the following formulas produced by the reaction of an acid group-containing acrylic resin and an alicyclic epoxy group-containing unsaturated compound. Resin (weight average molecular weight: 19,000 to 25,000).

(In the formula, Ra represents ^a hydrogen atom or a methyl group. R ^b represents an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms.)

[(B) component]
-I-184: 1-hydroxy-cyclohexyl-phenyl-ketone "IRGACURE-184" (manufactured by BASF, trade name)
I-819: Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide "IRGACURE-819" (manufactured by BASF, trade name)
-TPO: "IRGACURE-TPO" (trade name, manufactured by BASF), which is a 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
(For comparison: (B') component)
OXE-01: 1,2-octanedione-1- [4- (phenylthio) phenyl] -2- (O-benzoyloxime) "IRGACURE-OXE-01" (manufactured by BASF, trade name)

[Component (C)]
A-9300: Ethylene oxide-modified triacrylate of isocyanuric acid (manufactured by Shin-Nakamura Chemical Industry Co., Ltd., molecular weight: 423, a compound represented by the above formula (C1-1)).

[(D) component]
KBM-503: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)
KBM-803: 3-mercaptopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

[(E) component]
・ Park Mill D: Dikmyl Peroxide (manufactured by NOF CORPORATION, product name)

From Table 1, it was confirmed that the photosensitive resin composition of the present embodiment of the example had excellent pattern forming property at any exposure amount.
On the other hand, from Table 2, Comparative Examples 1, 2, 5, 6 and 9 containing only one component (A), Comparative Examples 3 and 4 not containing the component (A) of the present embodiment, and the present invention. When the resin compositions of Comparative Examples 7 to 10 containing no photopolymerization initiator corresponding to the component (B) of the embodiment were used, the pattern forming property was poor at any exposure amount.

Claims (17)

Component (A): Compound having two or more photopolymerizable functional groups and urethane bonds having different weight average molecular weight or number of photopolymerizable functional groups, component (B): photopolymerization initiator, component (E): heat Contains a radical polymerization initiator,
The photosensitive resin composition, wherein the component (B) contains at least one photopolymerization initiator selected from the group consisting of an acylphosphine oxide-based photopolymerization initiator and an alkylphenone-based photopolymerization initiator.
A photosensitive resin composition in which the content of the component (E) is 0.1 to 10% by mass based on the total solid content of the photosensitive resin composition. The photosensitive resin composition according to claim 1, wherein the component (A) contains two or more compounds having a (meth) acryloyl group as a photopolymerizable functional group. The photosensitive resin composition according to claim 1 or 2, wherein the component (A) contains a high molecular weight substance having a photopolymerizable functional group and a urethane bond and having a weight average molecular weight of 2,000 or more . The photosensitivity according to any one of claims 1 to 3, wherein the component (A) contains a high molecular weight substance having at least one skeleton selected from the group consisting of a chain hydrocarbon skeleton and an alicyclic skeleton. Sex resin composition. The photosensitive resin composition according to any one of claims 1 to 4, wherein the component (A) contains a low molecular weight substance having a photopolymerizable functional group and a urethane bond and having a weight average molecular weight of less than 2,000 . .. The photosensitive resin composition according to claim 5, wherein the low molecular weight substance as the component (A) contains a low molecular weight substance having two or more (meth) acryloyl groups as photopolymerizable functional groups. The photosensitive resin composition according to any one of claims 1 to 6, further comprising a component (C): a low molecular weight substance having an isocyanul ring skeleton. The photosensitive resin composition according to claim 7, wherein the low molecular weight substance as the component (C) contains a low molecular weight substance having two or more (meth) acryloyl groups together with an isocyanul ring skeleton. The photosensitive resin composition according to any one of claims 1 to 8, further containing a component (D): a silane compound. The photosensitive resin composition according to claim 9, wherein the component (D) contains a silane compound having a thiol group. A photosensitive resin film having a photosensitive layer using the photosensitive resin composition according to any one of claims 1 to 10. A step of providing a photosensitive layer on a substrate using the photosensitive resin composition according to any one of claims 1 to 10 or the photosensitive resin film according to claim 11, at least a part of the photosensitive layer. A method for producing a cured product, which comprises, in order, a step of irradiating an active light beam to form a photocurable portion and a step of removing at least a part of the photosensitive layer other than the photocurable portion to form a resin pattern. The method for producing a cured product according to claim 12, further comprising a step of heat-treating the resin pattern. The method for producing a cured product according to claim 12 or 13, 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 10. The laminate according to claim 15, 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 10.