Photosensitive resin composition, photosensitive resin film, printed wiring board, production method therefor, and semiconductor package

Abstract

Provided is a photosensitive resin composition containing: (A) a photopolymerizable compound having an ethylenically unsaturated group, and an acidic substituent; (B) a compound having an ethylenically unsaturated group, and an isocyanurate ring or glycoluril ring; and (C) a maleimide resin having two or more N-substituted maleimide groups, and a group including a condensed ring composed of an aromatic ring and aliphatic ring. Also provided are a photosensitive resin film using said photosensitive resin composition, a printed wiring board, a production method therefor, and a semiconductor package.

Description

Photosensitive resin composition, photosensitive resin film, printed circuit board and method for manufacturing the same, and semiconductor package

[0001] This embodiment relates to a photosensitive resin composition, a photosensitive resin film, a printed circuit board, a method for manufacturing the same, and a semiconductor package.

[0002] In recent years, electronic devices have become smaller and more high-performance, leading to increased density in printed circuit boards through an increase in the number of circuit layers and miniaturization of wiring. In particular, the density of semiconductor package substrates such as BGA (Ball Grid Array) and CSP (Chip Size Package), on which semiconductor chips are mounted, is remarkable. This requires not only miniaturization of wiring but also thinning of the insulating layer and further reduction in the diameter of vias used for interlayer connections.

[0003] A conventional method for manufacturing printed circuit boards (PCBs) is the build-up method (see, for example, Patent Document 1), in which an interlayer insulating layer and a conductor layer are sequentially laminated. In PCBs, with the miniaturization of wiring, the semi-additive method, in which the conductor layer is formed by plating, has become mainstream. In the conventional semi-additive method, for example, (1) a thermosetting resin film is laminated onto the conductor layer, and then the thermosetting resin film is cured by heating to form an "interlayer insulating layer". (2) Next, vias for interlayer connection are formed by laser processing, and then desmear treatment and roughening treatment are performed by alkaline permanganate treatment, etc. (3) After that, electroless copper plating is applied to the substrate, a pattern is formed using a resist, and then copper circuits, which are the conductor layers, are formed by electroplating. (4) Subsequently, after peeling off the resist, the copper circuits are formed by flash etching of the electroless plated layer.

[0004] As mentioned above, laser processing is the mainstream method for forming vias in the interlayer insulating layer formed by curing thermosetting resin film, but the ability to reduce the diameter of vias by laser irradiation using a laser processing machine is reaching its limits. Furthermore, when forming vias with a laser processing machine, it is necessary to form each via hole one by one, and when a large number of vias are required for high density, it takes a lot of time to form the vias, resulting in poor manufacturing efficiency.

[0005] Under these circumstances, a method has been proposed for forming multiple small-diameter vias simultaneously by photolithography using a photosensitive resin composition containing an acid-modified vinyl group-containing epoxy resin, a photopolymerizable compound, a photopolymerization initiator, an inorganic filler, and a silane compound, wherein the inorganic filler content is 10 to 80% by mass (see, for example, Patent Document 2).

[0006] Japanese Patent Publication No. 7-304931 Japanese Patent Publication No. 2017-116652

[0007] Incidentally, in electronic devices, the speed and capacity of signals used are increasing year by year. Accordingly, printed circuit board substrate materials are required to have dielectric properties that can reduce the transmission loss of high-frequency signals, namely low relative permittivity and low dielectric loss tangent. One method being considered to improve dielectric properties is to use components with low polarity, but increasing the content ratio of low-polarity components makes it difficult to achieve good adhesion strength to the conductor layer (hereinafter also referred to as "conductor adhesion"). Therefore, there is a need for a technology that can improve conductor adhesion while maintaining good dielectric properties.

[0008] In view of the current situation, this embodiment aims to provide a photosensitive resin composition with excellent dielectric properties and conductor adhesion, a photosensitive resin film using the photosensitive resin composition, a printed circuit board and a method for manufacturing the same, and a semiconductor package.

[0009] As a result of proceeding with studies to solve the above problems, the present inventors have found that the above problems can be solved by the following present embodiment. That is, the present embodiment relates to the following [1] to

[13] . [1] A photosensitive resin composition containing: (A) a photopolymerizable compound having an ethylenically unsaturated group and an acidic substituent; (B) a compound having an isocyanurate ring or a glycoluril ring and an ethylenically unsaturated group; and (C) a maleimide resin having a group containing a condensed ring of an aromatic ring and an aliphatic ring and two or more N-substituted maleimide groups. [2] The photosensitive resin composition according to [1] above, wherein the component (B) has an allyl group as the ethylenically unsaturated group. [3] The photosensitive resin composition according to [1] or [2] above, wherein the component (B) is a compound represented by the following general formula (B-1) or a compound represented by the following general formula (B-2). (In the formula, R Ｂ１ , R Ｂ２ and R Ｂ３ are each independently a hydrogen atom or an organic group, and at least one of R Ｂ１ , R Ｂ２ and R Ｂ３ is an allyl group.) (In the formula, R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ are each independently a hydrogen atom or an organic group, and at least one of R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ is an allyl group.) [4] The photosensitive resin composition according to any one of [1] to [3] above, wherein the group containing a condensed ring of an aromatic ring and an aliphatic ring possessed by the component (C) is a group containing an indane ring as the condensed ring. [5] The photosensitive resin composition according to [4] above, wherein the group containing an indane ring is a divalent group represented by the following general formula (C-1). (In the formula, R Ｃ１This is an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. Ｃ１ R is an integer between 0 and 3. Ｃ２ ~R Ｃ４ Each is independently an alkyl group having 1 to 10 carbon atoms. * represents a bonding site.) [6] The photosensitive resin composition according to any one of [1] to [5] above, wherein the content of component (B) is 1 to 50% by mass with respect to 100% by mass of the resin components in the photosensitive resin composition. [7] The photosensitive resin composition according to any one of [1] to [6] above, wherein the content of component (C) is 1 to 50% by mass with respect to 100% by mass of the resin components in the photosensitive resin composition. [8] The photosensitive resin composition according to any one of [1] to [7] above, wherein the ratio of the content of component (B) to the content of component (C) [(B) component / (C) component] is 0.1 to 10 by mass. [9] The photosensitive resin composition according to any one of [1] to [8] above, used for forming an interlayer insulating layer having a photovia.

[10] A photosensitive resin film comprising the photosensitive resin composition described in any of [1] to [9] above.

[11] A printed circuit board comprising a cured product of the photosensitive resin composition described in any of [1] to [9] above.

[12] A semiconductor package comprising the printed circuit board described in

[11] above and a semiconductor element.

[13] A method for manufacturing a printed circuit board comprising the following (1) to (4): (1) Laminating the photosensitive resin film described in

[10] above to one or both sides of a circuit board. (2) Forming an interlayer insulating layer having vias by exposing and developing the photosensitive resin film laminated in (1). (3) Heat curing the interlayer insulating layer having vias. (4) Forming a circuit pattern on the interlayer insulating layer.

[0010] According to this embodiment, it is possible to provide a photosensitive resin composition with excellent dielectric properties and conductor adhesion, a photosensitive resin film using the photosensitive resin composition, a printed circuit board and a method for manufacturing the same, and a semiconductor package.

[0011] This is a schematic diagram illustrating one aspect of the manufacturing process of a printed circuit board that uses the photosensitive resin film of this embodiment as the material for the interlayer insulating layer.

[0012] In the numerical ranges described herein, the lower and upper limits of those ranges may be replaced with the values ​​shown in the examples. Furthermore, the lower and upper limits of a numerical range can be arbitrarily combined with the lower or upper limits of other numerical ranges. In the notation "AA to BB" for the numerical range, the numbers AA and BB at both ends are included in the range as the lower and upper limits, respectively.

[0013] In this specification, for example, the phrase "10 or more" means 10 and numbers greater than 10, and the same applies when the numbers are different. Similarly, for example, the phrase "10 or less" means 10 and numbers less than 10, and the same applies when the numbers are different.

[0014] In this specification, the content of each component refers to the total content of multiple substances if there are multiple substances corresponding to each component, unless otherwise specified.

[0015] In this specification, "solids" means non-volatile components excluding volatile substances such as solvents, and includes substances that are liquid at room temperature. Here, room temperature in this specification means 25°C.

[0016] In this specification, "resin component" means resin and compounds that form resin through a curing reaction. In the photosensitive resin composition of this embodiment, for example, components (A), (B), (C), (D), and (H), described later, are resin components, while components (E), (F), (G), and (I) are not resin components.

[0017] In this specification, "ring-forming carbon number" refers to the number of carbon atoms required to form a ring, and does not include the number of carbon atoms in substituents on the ring. For example, both the cyclohexane skeleton and the methylcyclohexane skeleton have a ring-forming carbon number of 6.

[0018] The notation "(meth)acrylic XX" refers to either or both acrylic XX and its corresponding methacrylic XX. Similarly, "(meth)acryloyl group" refers to either or both an acryloyl group and a methacryloyl group.

[0019] In this specification, when the term "layer" is used, for example, as in "interlayer insulating layer," it includes not only solid layers, but also layers that are not solid but have some island-like structures, layers with holes, and layers where the interface with the adjacent layer is unclear.

[0020] In this specification, weight-average molecular weight (Mw) and number-average molecular weight (Mn) refer to values ​​measured in polystyrene equivalent by gel permeation chromatography (GPC). Specifically, the weight-average molecular weight (Mw) in this specification can be measured by the method described in the examples.

[0021] The mechanism of action described herein is speculative and does not limit the mechanism by which the effects of this embodiment are achieved.

[0022] Embodiments that combine any combination of the information described herein are also included.

[0023] [Photosensitive resin composition] The photosensitive resin composition of this embodiment is a photosensitive resin composition comprising: (A) a photopolymerizable compound having an ethylenically unsaturated group and an acidic substituent; (B) a compound having an isocyanurate ring or a glycoluryl ring and an ethylenically unsaturated group; and (C) a maleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring and two or more N-substituted maleimide groups.

[0024] In this specification, each component may be referred to as "Component (A)," "Component (B)," etc., as appropriate.

[0025] The photosensitive resin composition of this embodiment can form patterns such as vias by exposure and development. Therefore, the photosensitive resin composition of this embodiment is suitable for use in forming interlayer insulating layers having photovias. In this specification, "photovia" means a via formed by photolithography, i.e., exposure and development. Furthermore, the photosensitive resin composition of this embodiment is suitable for negative-type photosensitive resin compositions. Moreover, the photosensitive resin composition of this embodiment is also useful as a surface protective film such as solder resist.

[0026] <(A) Photopolymerizable compound having an ethylenically unsaturated group and an acidic substituent> The photosensitive resin composition of this embodiment contains (A) a photopolymerizable compound having an ethylenically unsaturated group and an acidic substituent. Component (A) may be used alone or in combination of two or more.

[0027] Component (A) is a compound that exhibits photopolymerization, particularly radical polymerization, because it has an ethylenically unsaturated group. Examples of ethylenically unsaturated groups in component (A) include vinyl group, allyl group, propargyl group, butenyl group, ethynyl group, phenylethynyl group, maleimide group, nadiimide group, and (meth)acryloyl group. Among these, the (meth)acryloyl group is preferred from the viewpoint of reactivity and via resolution.

[0028] Component (A) has an acidic substituent from the viewpoint of enabling alkaline development. Examples of acidic substituents on component (A) include carboxyl groups, sulfonic acid groups, and phenolic hydroxyl groups. Among these, a carboxyl group is preferred from the viewpoint of via resolution. The acid value of component (A) is preferably 20 to 200 mg KOH / g, more preferably 40 to 180 mg KOH / g, even more preferably 60 to 150 mg KOH / g, and particularly preferably 80 to 120 mg KOH / g. When the acid value of component (A) is above the lower limit, the via resolution tends to be superior. Also, when the acid value of component (A) is below the upper limit, the dielectric properties tend to be superior. The acid value of component (A) can be measured by the method described in the examples.

[0029] The weight-average molecular weight (Mw) of component (A) is preferably 300 to 10000, more preferably 500 to 7000, even more preferably 700 to 5000, even more preferably 1000 to 3000, and particularly preferably 1500 to 2500. When the weight-average molecular weight (Mw) of component (A) is within the above range, the conductive adhesion, heat resistance, and dielectric properties tend to be excellent.

[0030] Component (A) preferably contains an alicyclic skeleton from the viewpoint of dielectric properties. From the viewpoint of via resolution, conductor adhesion, and dielectric properties, an alicyclic skeleton with 5 to 20 ring-forming carbon atoms is preferred for component (A), more preferably an alicyclic skeleton with 5 to 18 ring-forming carbon atoms, even more preferably an alicyclic skeleton with 6 to 18 ring-forming carbon atoms, even more preferably an alicyclic skeleton with 8 to 14 ring-forming carbon atoms, and particularly preferably an alicyclic skeleton with 8 to 12 ring-forming carbon atoms. Furthermore, from the viewpoint of via resolution, conductor adhesion, and dielectric properties, the above alicyclic skeleton preferably consists of two or more rings, more preferably two to four rings, and even more preferably three rings. Examples of alicyclic skeletons with two or more rings include norbornane skeletons, decalin skeletons, bicycloundecane skeletons, and saturated dicyclopentadiene skeletons. These alicyclic skeletons may or may not have substituents. In this specification, a saturated dicyclopentadiene skeleton means a skeleton containing a ring structure in which the unsaturated bonds in the dicyclopentadiene ring are saturated, and tricyclo[5.2.1.0 ２，６ This can also be called a decane structure. Among these, a saturated dicyclopentadiene skeleton is preferred from the viewpoint of via resolution, conductor adhesion, and dielectric properties. From a similar viewpoint, component (A) is preferably one that includes an alicyclic skeleton represented by the following general formula (A-1).

[0031] (In the formula, R Ａ１ m represents an alkyl group having 1 to 12 carbon atoms and may be substituted anywhere in the above alicyclic skeleton. １ (This is an integer between 0 and 6. * indicates a connection site to another structure.)

[0032] In the above general formula (A-1), R Ａ１Examples of C1-C12 alkyl groups represented by include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl groups. C1-C6 alkyl groups are preferred, C1-C3 alkyl groups are more preferred, and methyl groups are even more preferred. １ m is an integer between 0 and 6, preferably between 0 and 2, and more preferably 0. １ If R is an integer between 2 and 6, then multiple R Ａ１ These may be the same or different. Furthermore, multiple R Ａ１ The carbon atoms may be substituted on the same carbon atom or on different carbon atoms, to the extent possible. * is a bonding site to another structure, and may be bonded to any carbon atom on the alicyclic skeleton, but it is preferable that they are bonded to the carbon atom at the site indicated by 1 or 2 in the general formula (A-1') below, and to the carbon atom at the site indicated by either 3 or 4.

[0033] (In the formula, R Ａ１ , m １ And * are the same as those in general formula (A-1).

[0034] Component (A) is preferably an acid-modified vinyl group-containing epoxy resin obtained by reacting a compound obtained by modifying an epoxy resin (a1) with an organic acid containing an ethylenically unsaturated group (a2) [hereinafter sometimes referred to as component (A')] with a polybasic acid anhydride containing a saturated or unsaturated group, from the viewpoint of via resolution, conductor adhesion, and dielectric properties. Here, "acid-modified" in "acid-modified vinyl group-containing epoxy resin" means having an acidic substituent, "vinyl group" means an ethylenically unsaturated group, and "epoxy resin" means using epoxy resin as a raw material. The acid-modified vinyl group-containing epoxy resin does not necessarily need to have epoxy groups and may not have epoxy groups. Below, preferred embodiments of component (A) obtained from (a1) epoxy resin, (a2) organic acid containing an ethylenically unsaturated group, and (a3) ​​polybasic acid anhydride containing a saturated or unsaturated group will be described.

[0035] (a1) Epoxy resin) The epoxy resin (a1) is preferably an epoxy resin having two or more epoxy groups. The epoxy resin (a1) may be used alone or in combination of two or more types. The epoxy resin (a1) is classified into glycidyl ether type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, etc. Among these, the glycidyl ether type epoxy resin is preferred.

[0036] (a1) Epoxy resins can be classified into various types based on differences in their main skeleton, including epoxy resins with an alicyclic skeleton, novolac-type epoxy resins, bisphenol-type epoxy resins, aralkyl-type epoxy resins, and other epoxy resins. Among these, epoxy resins with an alicyclic skeleton and bisphenol-type epoxy resins are preferred.

[0037] -Epoxy resin having an alicyclic skeleton- The alicyclic skeleton of the epoxy resin having an alicyclic skeleton will be described in the same way as the alicyclic skeleton of component (A) described above, and the preferred embodiments are also the same. As the epoxy resin having an alicyclic skeleton, the epoxy resin represented by the following general formula (A-2) is preferred.

[0038] (In the formula, R Ａ１ R represents an alkyl group having 1 to 12 carbon atoms and may be substituted anywhere in the above alicyclic skeleton. Ａ２ m represents an alkyl group with 1 to 12 carbon atoms. １ is an integer from 0 to 6, m ２ n is an integer between 0 and 3. n is a number between 0 and 50.

[0039] In general formula (A-2), R Ａ１ R in general formula (A-1) Ａ１ It is the same as and the preferred embodiment is also the same. R in general formula (A-2) Ａ２Examples of C1-C12 alkyl groups represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, etc. C1-C6 alkyl groups are preferred, C1-C3 alkyl groups are more preferred, and methyl groups are even more preferred. In general formula (A-2), m １ m in general formula (A-1) １ It is the same as, and the preferred embodiment is also the same. m in general formula (A-2) ２ n is an integer from 0 to 3, preferably 0 or 1, and more preferably 0. In general formula (A-2), n represents the number of repetitions of the structural unit in parentheses, and is a number from 0 to 50. Since epoxy resins are usually mixtures of structural units with different numbers of repetitions in parentheses, in that case, n is represented by the average value of the mixture. A number from 0 to 30 is preferred for n.

[0040] -Bisphenol-type epoxy resin- Examples of bisphenol-type epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 3,3',5,5'-tetramethyl-4,4'-diglycidyloxydiphenylmethane. Among these, bisphenol A type epoxy resin is preferred. As a bisphenol-type epoxy resin, an epoxy resin having a structural unit represented by the following general formula (A-3) is preferred.

[0041] (In the formula, R Ａ３ Y represents a hydrogen atom or a methyl group. Ａ１ Each of these independently represents a hydrogen atom or a glycidyl group. Multiple R Ａ３ These may be the same or different. ２ (This represents a number greater than or equal to 0.)

[0042] R Ａ３ From the viewpoint of improving the resolution of the via, it is preferable that both are methyl groups. Also, from the same viewpoint, Y Ａ１ It is preferable that it is a glycidyl group.

[0043] n ２The integer represents a number greater than or equal to 0, and can be appropriately selected from, for example, integers from 10 to 100, integers from 10 to 80, or integers from 15 to 60.

[0044] It is expressed by the above general formula (A-3), Y Ａ１ A bisphenol A-type epoxy resin or a bisphenol F-type epoxy resin in which is a glycidyl group is, for example, represented by the above general formula (A-3), Y Ａ１ The hydroxyl group (-OY) of a bisphenol A type epoxy resin or bisphenol F type epoxy resin is a hydrogen atom. Ａ１ It can be obtained by reacting it with epichlorohydrin.

[0045] Examples of novolac-type epoxy resins include bisphenol novolac-type epoxy resins such as bisphenol A novolac-type epoxy resin, bisphenol F novolac-type epoxy resin, and bisphenol S novolac-type epoxy resin; phenol novolac-type epoxy resin, cresol novolac-type epoxy resin, biphenyl novolac-type epoxy resin, and naphthol novolac-type epoxy resin. Examples of aralkyl-type epoxy resins include phenol aralkyl-type epoxy resin, biphenyl aralkyl-type epoxy resin, and naphthol aralkyl-type epoxy resin. Other epoxy resins include stilbene-type epoxy resin, naphthalene skeleton-containing epoxy resin, biphenyl-type epoxy resin, dihydroanthracene-type epoxy resin, cyclohexanedimethanol-type epoxy resin, trimethylol-type epoxy resin, alicyclic epoxy resin, aliphatic chain epoxy resin, heterocyclic epoxy resin, spiroring-containing epoxy resin, and rubber-modified epoxy resin.

[0046] (a2) Organic acid containing an ethylenically unsaturated group (a2) As the organic acid containing an ethylenically unsaturated group (a2), a monocarboxylic acid containing an ethylenically unsaturated group is preferred. The ethylenically unsaturated group that component (a2) has is the same as that listed as the ethylenically unsaturated group that component (A) has. Examples of component (a2) include acrylic acid derivatives such as acrylic acid, acrylic acid dimers, methacrylic acid, β-furfurylacrylic acid, β-styrylacrylic acid, cinnamic acid, crotonic acid, and α-cyanocinnamic acid; semi-ester compounds which are reaction products of hydroxyl group-containing acrylates and dibasic acid anhydrides; and semi-ester compounds which are reaction products of vinyl group-containing monoglycidyl ethers or vinyl group-containing monoglycidyl esters and dibasic acid anhydrides. Component (a2) may be used alone or in combination of two or more.

[0047] The above-mentioned semi-ester compounds are obtained by reacting one or more ethylenically unsaturated group-containing compounds selected from the group consisting of hydroxyl group-containing acrylates, vinyl group-containing monoglycidyl ethers, and vinyl group-containing monoglycidyl esters with a dibasic acid anhydride. In this reaction, it is preferable to react the ethylenically unsaturated group-containing compound and the dibasic acid anhydride in equimolar amounts.

[0048] Examples of hydroxyl group-containing acrylates used in the synthesis of the above-mentioned semi-ester compounds include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, trimethylolpropanedi(meth)acrylate, pentaerythritol tri(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Examples of vinyl group-containing monoglycidyl ethers include glycidyl (meth)acrylate.

[0049] The dibasic acid anhydride used in the synthesis of the above-mentioned semi-ester compound may contain saturated groups or unsaturated groups. Examples of dibasic acid anhydrides include succinic anhydride, maleic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, ethyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, ethylhexahydrophthalic anhydride, and itaconic anhydride.

[0050] Component (A'), obtained by reacting component (a1) and component (a2), has hydroxyl groups formed by a ring-opening addition reaction between the epoxy group of component (a1) and the carboxyl group of component (a2) when an ethylenically unsaturated monocarboxylic acid is used as component (a2). Next, by further reacting component (a3) ​​with component (A'), an acid-modified vinyl group-containing epoxy resin can be obtained in which the hydroxyl groups of component (A') (including hydroxyl groups originally present in component (a1)) and the acid anhydride group of component (a3) ​​are semi-esterified.

[0051] (a3) Polybasic acid anhydride containing saturated or unsaturated groups The (a3) ​​component may contain saturated groups or unsaturated groups. Examples of (a3) ​​components include succinic anhydride, maleic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, ethyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, ethylhexahydrophthalic anhydride, itaconic anhydride, etc. Among these, tetrahydrophthalic anhydride is preferred from the viewpoint of via resolution. The (a3) ​​component may be used alone or in combination of two or more.

[0052] In the reaction between component (A') and component (a3), for example, the acid value of the acid-modified vinyl group-containing epoxy resin can be adjusted by reacting 0.1 to 1.0 equivalents of component (a3) ​​with 1 equivalent of hydroxyl groups in component (A').

[0053] (Content of component (A)) The content of component (A) in the photosensitive resin composition of this embodiment is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, even more preferably 15 to 60% by mass, even more preferably 20 to 55% by mass, and particularly preferably 30 to 50% by mass, based on the total amount of resin components in the photosensitive resin composition of this embodiment, from the viewpoint of heat resistance, dielectric properties, chemical resistance and conductor adhesion.

[0054] <(B) Compound having an isocyanurate ring or glycoluryl ring and an ethylenically unsaturated group> Component (B) is a compound having an isocyanurate ring or glycoluryl ring and an ethylenically unsaturated group. Component (B) may be used alone or in combination of two or more.

[0055] The photosensitive resin composition of this embodiment exhibits improved dielectric properties due to the inclusion of component (B). The reason for this is presumed to be as follows: Component (B) contained in the photosensitive resin composition of this embodiment is a compound having an isocyanurate ring or a glycoluryl ring. The isocyanurate ring and glycoluryl ring have highly symmetrical structures, which is thought to reduce the overall polarity of the molecule. This reduction in polarity is thought to contribute to the reduction of the relative permittivity and dielectric loss tangent.

[0056] In this embodiment, compounds having an isocyanurate ring or a glycoluryl ring and an ethylenically unsaturated group are classified as component (B) rather than component (A), even if they have an acidic substituent.

[0057] Examples of ethylenically unsaturated groups in component (B) include vinyl groups, allyl groups, propargyl groups, butenyl groups, ethynyl groups, phenylethynyl groups, maleimide groups, nadiimide groups, and (meth)acryloyl groups. Among these, allyl groups are preferred from the viewpoint of dielectric properties.

[0058] The number of ethylenically unsaturated groups contained in one molecule of component (B) is preferably two or more, more preferably two to six, and even more preferably two to four.

[0059] In this embodiment, "isocyanurate ring" means a ring represented by the following general formula (B-a), and "glycoluryl ring" means a ring represented by the following general formula (B-b).

[0060] (In the formula, * represents a bonding site.)

[0061] (In the formula, * represents a bonding site.)

[0062] The number of isocyanurate rings in one molecule of component (B), which has an isocyanurate ring, is preferably 1 to 3, more preferably 1 or 2.

[0063] As component (B) having an isocyanurate ring, compounds represented by the following general formula (B-1) are preferred, and compounds represented by the following general formula (B-1a) are more preferred.

[0064] (In the formula, R Ｂ１ , R Ｂ２ and R Ｂ３ Each is independently a hydrogen atom or an organic group, R Ｂ１ , R Ｂ２ and R Ｂ３ (At least one of them is an allyl group.)

[0065] (In the formula, R Ｂ１ａ (This is a hydrogen atom or an organic group.)

[0066] In the above general formula (B-1), R Ｂ１ ~R Ｂ３ and R in the above general formula (B-1a) Ｂ１ａThe organic group represented is preferably a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. The number of carbon atoms in the substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferably 2 to 17, more preferably 3 to 15. The number of carbon atoms in the substituent is not included in this calculation. Examples of substituents that the aliphatic hydrocarbon group may have include alkoxy groups having 1 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, halogen atoms, etc. The number of carbon atoms in the substituent that the substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms may have is preferably 0 to 20, more preferably 0 to 15. The substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms may be linear or branched.

[0067] The substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. That is, the compound represented by the above general formula (B-1a) is preferably a compound represented by the following general formula (B-1a-1).

[0068] (In the formula, R Ｂ１ａ－１ (This refers to a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.)

[0069] R Ｂ１ａ－１ Examples of unsubstituted alkyl groups having 1 to 20 carbon atoms represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group.

[0070] In the above general formula (B-1a), R Ｂ１ａ The organic group represented by may include an isocyanurate ring having an allyl group. Ｂ１ａ If the compound contains an isocyanurate ring having an allyl group, component (B) is preferably a compound represented by the following general formula (B-1a-2).

[0071] (In the formula, R Ｂ１ａ－２(This is a divalent organic group.)

[0072] Examples of component (B) having an isocyanurate ring include trivinyl isocyanurate, trybutenyl isocyanurate, 1-(meth)acryloyl-3,5-dimethyl isocyanurate, 1-(meth)acryloyl-3,5-diphenyl isocyanurate, 5-octyl-1,3-diallyl isocyanurate, 5-dodecyl-1,3-diallyl isocyanurate, and triallyl isocyanurate.

[0073] The (B) component having a glycoluryl ring is preferably a compound represented by the following general formula (B-2).

[0074] (In the formula, R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ Each is independently a hydrogen atom or an organic group, R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ (At least one of them is an allyl group.)

[0075] In the above general formula (B-2), R Ｂ４ ~R Ｂ７ The explanation of the organic group represented by is R in the general formula (B-1) above. Ｂ１ , R Ｂ２ and R Ｂ３ This is the same as the explanation for the organic group represented by R. Ｂ４ ~R Ｂ７ Of these, the allyl groups are preferably 2 to 4, more preferably 3 or 4, and even more preferably 4. That is, the compound represented by the above general formula (B-2) is preferably the compound represented by the following formula (B-2a).

[0076]

[0077] Examples of component (B) having a glycoluryl ring include 1-allyl glycoluryl, 1,3-diallyl glycoluryl, 1,4-diallyl glycoluryl, 1,6-diallyl glycoluryl, 1,3,4-trialyl glycoluryl, 1,3,4,6-tetraallyl glycoluryl, 1-allyl-3a-methyl glycoluryl, 1,3-diallyl-3a-methyl glycoluryl, 1,4-diallyl-3a-methyl glycoluryl, 1,6-diallyl-3a-methyl glycoluryl, 1,3,4-trialyl-3a-methyl glycoluryl, 1,3,4,6-tetraallyl-3a-methyl glycoluryl, 1-allyl-3a,6a-dimethyl glycoluryl, and 1,3-diallyl-3a,6 Examples include α-dimethylglycoluryl, 1,4-diallyl-3a,6a-dimethylglycoluryl, 1,6-diallyl-3a,6a-dimethylglycoluryl, 1,3,4-triallyl-3a,6a-dimethylglycoluryl, 1,3,4,6-tetraallyl-3a,6a-dimethylglycoluryl, 1-allyl-3a,6a-diphenylglycoluryl, 1,3-diallyl-3a,6a-diphenylglycoluryl, 1,4-diallyl-3a,6a-diphenylglycoluryl, 1,6-diallyl-3a,6a-diphenylglycoluryl, 1,3,4,6-tetraallyl-3a,6a-diphenylglycoluryl, and the like. Among these, the compound represented by the above general formula (B-2a) (1,3,4,6-tetraallylglycoluryl) is preferred.

[0078] As for component (B), among the compounds mentioned above, compounds having an isocyanurate ring and an ethylenically unsaturated group are preferred from the viewpoint of dielectric properties, compounds represented by the above general formula (B-1) are more preferred, compounds represented by the above general formula (B-1a) are even more preferred, and compounds represented by the above general formula (B-1a-1) are even more preferred.

[0079] The boiling point of component (B) is preferably 150°C or higher, more preferably 160°C or higher, and even more preferably 170°C or higher, from the viewpoint of dielectric properties and conductive adhesion. The upper limit of the boiling point of component (B) is not particularly limited and may be 400°C or lower, or 300°C or lower. In this specification, "boiling point" refers to the boiling point at normal pressure (1 atmosphere).

[0080] (Content of component (B)) The content of component (B) in the photosensitive resin composition of this embodiment is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, even more preferably 3 to 30% by mass, even more preferably 4 to 20% by mass, and particularly preferably 5 to 10% by mass, based on the total amount of resin components in the photosensitive resin composition of this embodiment, from the viewpoint of heat resistance, dielectric properties, chemical resistance and conductor adhesion.

[0081] <(C) Maleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring, and two or more N-substituted maleimide groups> The photosensitive resin composition of this embodiment contains a maleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring, and two or more N-substituted maleimide groups. Component (C) may be used alone or in combination of two or more.

[0082] Component (C) has a group containing a fused ring of an aromatic ring and an aliphatic ring, and it is believed that the bulky three-dimensional structure of the fused ring contributes to improving the dielectric properties and conductor adhesion of the cured product of the photosensitive resin composition of this embodiment.

[0083] Component (C) is preferably an aromatic maleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring, and two or more N-substituted maleimide groups directly bonded to the aromatic ring, from the viewpoint of dielectric properties and conductive adhesion, and more preferably an aromatic bismaleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring, and two N-substituted maleimide groups directly bonded to the aromatic ring.

[0084] The fused ring of an aromatic ring and an aliphatic ring in component (C) is preferably a fused bicyclic structure from the viewpoint of dielectric properties, conductor adhesion and ease of manufacture, more preferably a group containing a fused ring of a benzene ring and an aliphatic ring, and even more preferably a group containing an indan ring. The group containing an indan ring is preferably a divalent group represented by the following general formula (C-1).

[0085] (In the formula, R Ｃ１ This is an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. Ｃ１ R is an integer between 0 and 3. Ｃ２ ~R Ｃ４ Each of these is an alkyl group having 1 to 10 carbon atoms. (* indicates a bonding site.)

[0086] In the above general formula (C-1), R Ｃ１ Examples of C1-C10 alkyl groups represented by include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups. These alkyl groups may be linear or branched. Ｃ１ Examples of alkyl groups included in the C1-C10 alkyloxy group and C1-C10 alkylthio group represented by the above include the same C1-C10 alkyl groups. Ｃ１ Examples of aryl groups having 6 to 10 carbon atoms represented by R include the phenyl group and the naphthyl group. Ｃ１ The aryl groups included in the aryloxy group and arylthio group having 6 to 10 carbon atoms represented by the above-mentioned aryl group having 6 to 10 carbon atoms are the same as those mentioned above. Ｃ１Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and the like. In the general formula (C-1), n Ｃ１ When is an integer of 1 to 3, R Ｃ１ is preferably an alkyl group having 1 to 4 carbon atoms from the viewpoints of solvent solubility and reactivity.

[0087] R Ｃ２ ~R Ｃ４ Examples of the alkyl group having 1 to 10 carbon atoms represented by include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and the like. These alkyl groups may be either linear or branched. Among these, R Ｃ２ ~R Ｃ４ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. In the general formula (C-1), n Ｃ１ is an integer of 0 to 3. When n Ｃ１ is 2 or 3, a plurality of R Ｃ１ may be the same or different from each other.

[0088] Among the above, from the viewpoint of ease of production, the divalent group represented by the general formula (C-1) is more preferably a divalent group represented by the following formula (C-1a), the following formula (C-1a'), or the following formula (C-1a'') in which n Ｃ１ is 0 and R Ｃ２ ~R Ｃ４ is a methyl group.

[0089] (In the formula, * represents a bonding site.)

[0090] As the component (C) containing the divalent group represented by the general formula (C-1), those represented by the following general formula (C-2) are preferable from the viewpoints of dielectric properties, conductor adhesion, heat resistance, and ease of production.

[0091] (In the formula, R Ｃ１ ~R Ｃ４ and n Ｃ１This is the same as the one in the general formula (C-1) above. R Ｃ５ Each of these is independently a C1-C10 alkyl group, a C1-C10 alkyloxy group, a C1-C10 alkylthio group, a C6-C10 aryl group, a C6-C10 aryloxy group, a C6-C10 arylthio group, a C3-C10 cycloalkyl group, a halogen atom, a nitro group, a hydroxyl group, or a mercapto group. Ｃ２ Each of these is an integer between 0 and 4, independently of the others. Ｃ３ (This is a number between 0.95 and 10.0.)

[0092] In the above general formula (C-2), multiple R Ｃ１ fellows, multiple n Ｃ１ fellow, multiple R Ｃ５ fellows, multiple n Ｃ２ Each of these elements may be identical or different. Ｃ３ If the number exceeds 1, multiple R Ｃ２ fellow, multiple R Ｃ３ R with each other and with multiple Rs Ｃ４ Each of the members may be the same or different.

[0093] In the above general formula (C-2), R Ｃ５ For an explanation of the C1-C10 alkyl groups, C1-C10 alkyloxy groups, C1-C10 alkylthio groups, C6-C10 aryl groups, C6-C10 aryloxy groups, C6-C10 arylthio groups, and C3-C10 cycloalkyl groups represented by R, see above. Ｃ１ The explanation is the same as for alkyl groups having 1 to 10 carbon atoms, alkyloxy groups having 1 to 10 carbon atoms, alkylthio groups having 1 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, aryloxy groups having 6 to 10 carbon atoms, arylthio groups having 6 to 10 carbon atoms, and cycloalkyl groups having 3 to 10 carbon atoms. Among these, R Ｃ５ From the viewpoint of solvent solubility and ease of manufacture, alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, and aryl groups having 6 to 10 carbon atoms are preferred, alkyl groups having 1 to 3 carbon atoms are more preferred, and methyl groups are even more preferred.

[0094] n in the above general formula (C-2)Ｃ２ n is an integer from 0 to 4, and is preferably an integer from 0 to 3, more preferably 0 or 2, from the viewpoint of compatibility with other resins, dielectric properties, conductive adhesion, and ease of manufacture. Ｃ３ From the viewpoint of dielectric properties, conductive adhesion, solvent solubility, handling properties, and heat resistance, the number is preferably 0.98 to 8.0, more preferably 1.0 to 7.0, and even more preferably 1.1 to 6.0. Ｃ３ This represents the average number of structures containing an indan ring.

[0095] The component (C) represented by the above general formula (C-2) is preferably represented by the following general formula (C-3) from the viewpoint of dielectric properties, conductor adhesion, solvent solubility, and ease of manufacture.

[0096] (In the formula, R Ｃ６ Each of these is independently a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group. Ｃ３ This is the same as the one in the general formula (C-2) above.

[0097] (Content of component (C)) From the viewpoint of dielectric properties and conductive adhesion, the content of component (C) in the photosensitive resin composition of this embodiment is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, even more preferably 3 to 30% by mass, even more preferably 4 to 20% by mass, and particularly preferably 5 to 10% by mass, based on the total amount of resin components in the photosensitive resin composition of this embodiment.

[0098] The ratio of the content of component (B) to the content of component (C) in the photosensitive resin composition of this embodiment [component (B) / component (C)] is preferably 0.1 to 10 by mass, more preferably 0.3 to 5, even more preferably 0.5 to 3, and particularly preferably 0.8 to 1.5. When the content ratio [component (B) / component (C)] is within the above range, the dielectric properties tend to be better.

[0099] <(D) Compound having two or more ethylenically unsaturated groups and no acidic substituents> The photosensitive resin composition of this embodiment preferably further contains (D) a compound having two or more ethylenically unsaturated groups and no acidic substituents (excluding components (B) and (C)). Component (D) reacts with the ethylenically unsaturated groups of component (A) to increase the crosslinking density of the photosensitive resin composition after curing. The inclusion of component (D) in the photosensitive resin composition of this embodiment tends to further improve the heat resistance and dielectric properties of the cured product of the photosensitive resin composition of this embodiment. Component (D) may be used alone or in combination of two or more types.

[0100] Examples of ethylenically unsaturated groups in component (D) include vinyl groups, allyl groups, propargyl groups, butenyl groups, ethynyl groups, phenylethynyl groups, maleimide groups, nadiimide groups, and (meth)acryloyl groups. Among these, (meth)acryloyl groups are preferred from the viewpoint of reactivity and via resolution.

[0101] Examples of component (D) include difunctional monomers having two (meth)acryloyl groups and polyfunctional monomers having three or more (meth)acryloyl groups. It is preferable that component (D) contains the above-mentioned polyfunctional monomers.

[0102] Examples of the above-mentioned difunctional monomers include aliphatic di(meth)acrylates such as trimethylolpropane di(meth)acrylate, polypropylene glycol di(meth)acrylate, and polyethylene glycol di(meth)acrylate; di(meth)acrylates having an alicyclic skeleton such as dicyclopentadiene di(meth)acrylate and tricyclodecanedimethanol di(meth)acrylate; and aromatic di(meth)acrylates such as 2,2-bis(4-(meth)acryloxypolyethoxypolypropoxyphenyl)propane and bisphenol A diglycidyl ether di(meth)acrylate.

[0103] Examples of the above-mentioned polyfunctional monomers include (meth)acrylate compounds having a trimethylolpropane-derived skeleton such as trimethylolpropane tri(meth)acrylate; (meth)acrylate compounds having a tetramethylolmethane-derived skeleton such as tetramethylolmethane tri(meth)acrylate and tetramethylolmethane tetra(meth)acrylate; (meth)acrylate compounds having a pentaerythritol-derived skeleton such as pentaerythritol tri(meth)acrylate and pentaerythritol tetra(meth)acrylate; (meth)acrylate compounds having a dipentaerythritol-derived skeleton such as dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate; (meth)acrylate compounds having a ditrimethylolpropane-derived skeleton such as ditrimethylolpropane tetra(meth)acrylate; and (meth)acrylate compounds having a diglycerin-derived skeleton. Among these, from the viewpoint of via resolution and conductor adhesion, (meth)acrylate compounds having a trimethylolpropane-derived skeleton, such as trimethylolpropane tri(meth)acrylate, are preferred, and trimethylolpropane tri(meth)acrylate is more preferred. Here, the above-mentioned "(meth)acrylate compound having a skeleton derived from XXX" (where XXX is the name of the compound) means an esterified product of XXX and (meth)acrylic acid, and this esterified product also includes compounds modified with alkylene oxy groups.

[0104] (Content of component (D)) When the photosensitive resin composition of this embodiment contains component (D), the content of component (D) in the photosensitive resin composition of this embodiment is preferably 5 to 70% by mass, more preferably 10 to 60% by mass, even more preferably 15 to 50% by mass, and particularly preferably 20 to 40% by mass, based on the total amount of resin components of the photosensitive resin composition of this embodiment, from the viewpoint of heat resistance and dielectric properties.

[0105] <(E) Inorganic Filler> The photosensitive resin composition of this embodiment preferably further contains (E) an inorganic filler. The inclusion of (E) an inorganic filler in the photosensitive resin composition of this embodiment tends to further improve the low thermal expansion, heat resistance, and flame retardancy of the cured product of the photosensitive resin composition of this embodiment. One type of (E) inorganic filler may be used alone, or two or more types may be used in combination.

[0106] (E) Examples of inorganic fillers include silica, alumina, titanium oxide, mica, beryllium, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay, molybdate compounds, talc, aluminum borate, silicon carbide, etc. Among these, (E) as inorganic fillers, silica and alumina are preferred from the viewpoint of thermal expansion coefficient, heat resistance and flame retardancy, and silica is more preferred. Examples of silica include crushed silica, fumed silica, and fused silica. Examples of shapes for (E) inorganic fillers include spherical and crushed shapes, with spherical being preferred.

[0107] (E) Volume average particle size of inorganic filler (D ５０ The volume average particle diameter (D) is preferably 0.01 to 10 μm, more preferably 0.05 to 5 μm, even more preferably 0.1 to 2 μm, even more preferably 0.2 to 1.5 μm, and particularly preferably 0.3 to 1 μm. In this specification, the volume average particle diameter (D) is used. ５０ The particle size can be determined by using a submicron particle analyzer (manufactured by Beckman Coulter, Inc., product name: N5) in accordance with the international standard ISO 13321, measuring particles dispersed in a solvent with a refractive index of 1.38, and determining the particle size as the particle diameter corresponding to 50% of the cumulative value (by volume) in the particle size distribution.

[0108] (E) The inorganic filler may be surface-treated with a surface treatment agent such as a coupling agent, for example, from the viewpoint of dielectric properties, chemical resistance, and conductor adhesion. When a coupling agent is used, the treatment method may be a so-called integral blend treatment method in which the inorganic filler is blended into the photosensitive resin composition and then the coupling agent is added, or it may be a method in which the surface is treated with a coupling agent beforehand, either dry or wet.

[0109] (Content of (E) Inorganic Filler) When the photosensitive resin composition of this embodiment contains (E) an inorganic filler, the content of (E) an inorganic filler in the photosensitive resin composition of this embodiment is preferably 5 to 80% by mass, more preferably 10 to 75% by mass, even more preferably 20 to 70% by mass, even more preferably 40 to 65% by mass, and particularly preferably 50 to 60% by mass, based on the total solid content of the photosensitive resin composition of this embodiment, from the viewpoint of low thermal expansion, heat resistance, flame retardancy, dielectric properties, chemical resistance and conductor adhesion.

[0110] <(F) Organic Peroxide> The photosensitive resin composition of this embodiment preferably further contains (F) organic peroxide. (F) organic peroxide is a polymerization initiator for the thermal radical polymerization reaction of ethylenically unsaturated groups. The inclusion of (F) organic peroxide in the photosensitive resin composition of this embodiment tends to further improve the dielectric properties of the cured product of the photosensitive resin composition of this embodiment. One type of (F) organic peroxide may be used alone, or two or more types may be used in combination.

[0111] (F) Examples of organic peroxides include peroxyketals such as 1,1-di(t-butylperoxy)cyclohexane, 2,2-di(t-butylperoxy)butane, 2,2-di(4,4-di-t-butylperoxycyclohexyl)propane, and 1,1-di(t-amylperoxy)cyclohexane; hydroperoxides such as cumene hydroperoxide and t-butyl hydroperoxide; alkyl peroxides such as t-butylperoxyacetate and t-amylperoxyisononanoate; and t-butylcumylperoxide and di-t-butyl Examples include dialkyl peroxides such as t-butyl peroxide, dicumyl peroxide, di-t-hexyl peroxide, and 1,3-di(t-butylperoxyisopropyl)benzene; peroxyesters such as t-butyl peroxyacetate, t-butyl peroxybenzoate, and t-butylperoxyisopropyl monocarbonate; peroxycarbonates such as t-butylperoxyisopropyl carbonate and polyethertetrakis(t-butylperoxycarbonate); and diacyl peroxides such as dibenzoyl peroxide. Among these, 1,3-di(t-butylperoxyisopropyl)benzene is preferred.

[0112] (Content of (F) Organic Peroxide) When the photosensitive resin composition of this embodiment contains (F) organic peroxide, the content of (F) organic peroxide in the photosensitive resin composition of this embodiment is preferably 0.05 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, even more preferably 0.5 to 7 parts by mass, even more preferably 1 to 5 parts by mass, and particularly preferably 2 to 4 parts by mass, based on 100 parts by mass of the total amount of resin components in the photosensitive resin composition of this embodiment.

[0113] <(G) Photopolymerization Initiator> The photosensitive resin composition of this embodiment preferably further contains (G) a photopolymerization initiator. The photosensitive resin composition of this embodiment tends to have improved via resolution by containing (G) a photopolymerization initiator. (G) A single type of photopolymerization initiator may be used, or two or more types may be used in combination.

[0114] (G) The photopolymerization initiator is not particularly limited as long as it can photopolymerize ethylenically unsaturated groups, and can be appropriately selected from commonly used photopolymerization initiators. (G) Examples of photopolymerization initiators include benzoin compounds such as benzoin, benzoin methyl ether, and benzoin isopropyl ether; acetophenone compounds such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-[4-(methylthio)benzoyl]-2-(4-morpholinyl)propane, and N,N-dimethylaminoacetophenone; 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone, 2 Examples include anthraquinone compounds such as aminoanthraquinone; ketal compounds such as acetophenone dimethyl ketal and benzyl dimethyl ketal; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinyl)heptane; acylphosphine oxide compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide; and oxime ester compounds such as 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(O-benzoyl oxime), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanone-1-(O-acetyl oxime), and 1-phenyl-1,2-propanedione-2-[O-(ethoxycarbonyl)oxime]. Among these, acylphosphine oxide compounds are preferred from the viewpoint of bottom curability, and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide is more preferred.

[0115] (Content of (G) Photopolymerization Initiator) When the photosensitive resin composition of this embodiment contains (G) a photopolymerization initiator, the content of (G) in the photosensitive resin composition of this embodiment is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, even more preferably 0.5 to 5 parts by mass, and particularly preferably 1 to 3 parts by mass, based on 100 parts by mass of the total amount of resin components in the photosensitive resin composition of this embodiment.

[0116] <(H) Other Thermosetting Resins> The photosensitive resin composition of this embodiment may further contain (H) other thermosetting resins other than components (B) and (C) described above. The photosensitive resin composition of this embodiment tends to have improved heat resistance of the interlayer insulating layer formed from the photosensitive resin composition of this embodiment by containing (H) other thermosetting resins. (H) Other thermosetting resins may be used individually or in combination of two or more types.

[0117] (H) Other thermosetting resins include, for example, epoxy resins, maleimide resins other than component (C), allyl resins other than component (B), isocyanate resins, phenolic resins, cyanate resins, benzoxazine resins, oxetane resins, amino resins, unsaturated polyester resins, vinyl resins, dicyclopentadiene resins, silicone resins, triazine resins, melamine resins, and other known thermosetting resins. Among the above options, the photosensitive resin composition of this embodiment preferably contains one or more selected from the group consisting of epoxy resins and isocyanate resins, from the viewpoint of heat resistance and conductive adhesion.

[0118] (Epoxy resin) As the epoxy resin, an epoxy resin having two or more epoxy groups is preferred. Epoxy resins are classified into, for example, glycidyl ether type epoxy resins, glycidyl amine type epoxy resins, glycidyl ester type epoxy resins, etc. Among these, glycidyl ether type epoxy resins are preferred.

[0119] Furthermore, epoxy resins are classified into various types based on differences in their main skeleton, and each of the aforementioned types of epoxy resins is further classified as follows: Specifically, epoxy resins include, for example, bisphenol-type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin; bisphenol-based novolac type epoxy resins such as bisphenol A novolac type epoxy resin and bisphenol F novolac type epoxy resin; novolac type epoxy resins other than the aforementioned bisphenol-based novolac type epoxy resins, such as phenol novolac type epoxy resin, cresol novolac type epoxy resin, and biphenyl novolac type epoxy resin; phenol aralkyl type epoxy resin; and stilbene type epoxy resin. Epoxy resins are classified into the following categories: lipids; naphthalene skeleton-containing epoxy resins such as naphthol novolac type epoxy resin, naphthol type epoxy resin, naphthol aralkyl type epoxy resin, and naphthylene ether type epoxy resin; biphenyl type epoxy resin; biphenyl aralkyl type epoxy resin; xylylene type epoxy resin; dihydroanthracene type epoxy resin; alicyclic epoxy resins such as saturated dicyclopentadiene type epoxy resin; heterocyclic epoxy resin; spiroring-containing epoxy resin; cyclohexanedimethanol type epoxy resin; trimethylol type epoxy resin; aliphatic chain epoxy resin; rubber-modified epoxy resin; and so on. Among these, bisphenol type epoxy resin, naphthalene skeleton-containing epoxy resin, and biphenyl aralkyl type epoxy resin are preferred, with naphthalene skeleton-containing epoxy resin being more preferred.

[0120] (Isocyanate resins) Examples of isocyanate resins include compounds having two or more isocyanate groups. Compounds having two or more isocyanate groups include aliphatic isocyanates having two or more isocyanate groups, such as trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate; alicyclic isocyanates having two or more isocyanate groups, such as 1,3-cyclopentane diisocyanate, 1,4-cyclohexane diisocyanate, 1,2-cyclohexane diisocyanate, isophorone diisocyanate, and norbornane diisocyanate; aromatic isocyanates having two or more isocyanate groups, such as xylylene diisocyanate, 2,4-tolylene diisocyanate, and 2,6-tolylene diisocyanate; their biuret forms; and their nurates. Among these, aliphatic isocyanates having two or more isocyanate groups are preferred, and hexamethylene diisocyanate is more preferred.

[0121] If the photosensitive resin composition of this embodiment contains epoxy resin as (H) other thermosetting resin, the epoxy resin content in the photosensitive resin composition of this embodiment is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, and even more preferably 3 to 10% by mass, based on the total amount of resin components in the photosensitive resin composition of this embodiment, from the viewpoint of heat resistance, dielectric properties and conductive adhesion.

[0122] If the photosensitive resin composition of this embodiment contains an isocyanate resin as (H) other thermosetting resin, the isocyanate resin content in the photosensitive resin composition of this embodiment is preferably 0.5 to 20% by mass, more preferably 1 to 10% by mass, and even more preferably 2 to 7% by mass, based on the total amount of resin components in the photosensitive resin composition of this embodiment, from the viewpoint of heat resistance, dielectric properties and conductive adhesion.

[0123] <(I) Curing Accelerator> The photosensitive resin composition of this embodiment preferably further contains (I) a curing accelerator. The inclusion of (I) a curing accelerator in the photosensitive resin composition of this embodiment tends to further improve the heat resistance, dielectric properties, etc. of the cured product of the photosensitive resin composition of this embodiment. (I) A curing accelerator may be used alone or in combination of two or more types.

[0124] (I) As curing accelerators, imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 2-phenylimidazole, 2-phenyl-1-benzyl-1H-imidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, isocyanate mask imidazole (addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole); trimethylamine, N,N-dimethyloctylamine, N-benzyldimethylamine, pyridine, N-methylmorpholine, hexa(N-methyl)melamine, 2,4,6-tris(dimethylaminophenol), tetramethyl Examples include tertiary amines such as luguanidine and m-aminophenol; organic phosphines such as tributylphosphine, triphenylphosphine, and tris-2-cyanoethylphosphine; phosphonium salts such as tri-n-butyl(2,5-dihydroxyphenyl)phosphonium bromide and hexadecyltributylphosphonium chloride; quaternary ammonium salts such as benzyltrimethylammonium chloride and phenyltributylammonium chloride; the polybasic anhydrides mentioned above; diphenyliodonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, and 2,4,6-triphenylthiopyrillium hexafluorophosphate. Among these, imidazole compounds are preferred from the viewpoint of obtaining excellent curing properties.

[0125] (Content of (I) curing accelerator) When the photosensitive resin composition of this embodiment contains (I) curing accelerator, the content of (I) curing accelerator in the photosensitive resin composition of this embodiment is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, and even more preferably 0.1 to 1 part by mass, based on 100 parts by mass of the total amount of resin components in the photosensitive resin composition of this embodiment, from the viewpoint of improving heat resistance and dielectric properties.

[0126] <(J) Other Components> The photosensitive resin composition of this embodiment may contain (J) other components as needed. Examples of (J) other components include resins other than the above components; curing agents; organic fillers; sensitizers; polymerization inhibitors; foam stabilizers; pigments; adhesive aids such as melamine; foam stabilizers such as silicone compounds; thickeners; flame retardants; organic solvents, etc. Each of these may be used alone or in combination of two or more. The content of (J) other components in the photosensitive resin composition of this embodiment may be adjusted as appropriate according to the respective purpose, but each may be 0.01 to 10% by mass, 0.05 to 5% by mass, or 0.1 to 1% by mass based on the total solid content of the photosensitive resin composition.

[0127] <Method for producing the photosensitive resin composition> The photosensitive resin composition of this embodiment can be obtained by kneading and mixing each component in a roll mill, bead mill, or the like.

[0128] [Photosensitive Resin Film] The photosensitive resin film of this embodiment contains the photosensitive resin composition of this embodiment. This photosensitive resin film is useful as a photosensitive layer for forming an interlayer insulating layer. The components in the photosensitive resin film of this embodiment and their content are as described in the description of the components in the photosensitive resin composition of this embodiment and their content.

[0129] The photosensitive resin film of this embodiment may be provided on a carrier film. Examples of carrier films include polyesters such as polyethylene terephthalate and polybutylene terephthalate; and polyolefins such as polypropylene and polyethylene. The thickness of the carrier film is preferably 5 to 100 μm, more preferably 10 to 60 μm, and even more preferably 15 to 45 μm. The photosensitive resin film of this embodiment may also have a protective film on the side opposite to the side in contact with the carrier film.

[0130] The photosensitive resin film of this embodiment can be formed, for example, by applying and drying the photosensitive resin composition of this embodiment onto a carrier film using a known coating apparatus such as a comma coater, bar coater, kiss coater, roll coater, gravure coater, or die coater. The coating film formed by applying the photosensitive resin composition can be dried using a hot air dryer, a far-infrared ray dryer, or a near-infrared ray dryer. The drying temperature is preferably 60 to 150°C, more preferably 70 to 120°C, and even more preferably 80 to 110°C. The drying time is preferably 1 to 60 minutes, more preferably 2 to 30 minutes, and even more preferably 5 to 20 minutes. The content of residual diluent in the photosensitive resin film after drying is preferably 3% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less, from the viewpoint of avoiding the diffusion of the diluent during the manufacturing process of printed circuit boards.

[0131] The thickness of the photosensitive resin film in this embodiment is preferably 1 to 100 μm, more preferably 3 to 60 μm, and even more preferably 5 to 40 μm, from the viewpoint of thinning the printed circuit board.

[0132] [Printed Wiring Board] The printed wiring board of this embodiment is a printed wiring board that includes a cured product of the photosensitive resin composition of this embodiment. Preferably, the printed wiring board of this embodiment has an interlayer insulating layer which is a cured product of the photosensitive resin film of this embodiment. The "interlayer insulating layer" of the printed wiring board of this embodiment also includes the state after various processing or treatments such as the formation of vias and wiring and roughening treatment have been performed.

[0133] The method for manufacturing a printed circuit board according to this embodiment is not particularly limited as long as it uses the photosensitive resin film of this embodiment, but a method for manufacturing a printed circuit board that includes the following (1) to (4) is preferred. (1): Laminating the photosensitive resin film of this embodiment to one or both sides of a circuit board (hereinafter also referred to as the "laminating step (1)"). (2): Forming an interlayer insulating layer having vias by exposing and developing the photosensitive resin film laminated in (1) (hereinafter also referred to as the "via formation step (2)"). (3): Heat curing the interlayer insulating layer having vias (hereinafter also referred to as the "heat curing step (3)"). (4): Forming a circuit pattern on the interlayer insulating layer (hereinafter also referred to as the "circuit pattern formation step (4)").

[0134] The method for manufacturing a printed circuit board according to this embodiment will be described below with reference to Figure 1 as appropriate. In this specification, for convenience, certain operations may be referred to as "step XX," but "step XX" is not limited to the embodiments specifically described herein.

[0135] (Laminating process (1)) In laminating process (1), the photosensitive resin film of this embodiment is laminated to one or both sides of the circuit board. Figure 1(a) illustrates the process of forming a photosensitive layer 103 on both sides of a substrate 101 having a circuit pattern 102. The photosensitive layer 103 can be formed by laminating the photosensitive resin film of this embodiment to both sides of the substrate 101. Lamination can be performed, for example, by pressing and heating using a vacuum laminator. If a carrier film is attached to the photosensitive layer 103 after lamination, the carrier film may be peeled off before exposure, as described later, or after exposure.

[0136] (Via formation process (2)) In via formation process (2), an interlayer insulating layer having vias is formed by exposing and developing the photosensitive layer formed in lamination process (1). Figure 1(b) illustrates the process of forming an interlayer insulating layer 104 having vias 105 by exposing and developing the photosensitive layer 103. Exposing the photosensitive layer 103 initiates a photoradical polymerization reaction, thereby curing the photosensitive resin film.

[0137] The method for exposing the photosensitive layer 103 may be, for example, a mask exposure method in which active light is irradiated in an image pattern through a negative or positive mask pattern called artwork, or a direct drawing exposure method such as LDI (Laser Direct Imaging) exposure or DLP (Digital Light Processing) exposure, in which active light is irradiated in an image pattern. Examples of light sources for the active light include gas lasers such as carbon arc lamps, mercury vapor arc lamps, high-pressure mercury lamps, xenon lamps, and argon lasers; solid-state lasers such as YAG lasers; and known light sources such as semiconductor lasers that effectively emit ultraviolet or visible light. The exposure amount can be appropriately adjusted depending on the light source used and the thickness of the photosensitive layer. For example, when exposing a photosensitive layer with a thickness of 1 to 100 μm using ultraviolet irradiation from a high-pressure mercury lamp, the exposure amount is preferably 10 to 1,000 mJ / cm². ２ , more preferably 50 to 700 mJ / cm² ２More preferably 150 to 400 mJ / cm² ２ That is the case.

[0138] Next, if a carrier film is present on the photosensitive layer 103, the carrier film is removed before development. During development, the uncured portion of the photosensitive layer 103 is removed, and the photocured portion is formed on the substrate as the interlayer insulating layer 104. The development method may be wet development or dry development, but wet development is preferred. As for the wet development method, a spray method is preferred from the viewpoint of improving resolution. Examples of developer solutions include alkaline aqueous solutions, aqueous developers, and organic solvent-based developers, and among these, alkaline aqueous solutions are preferred. After exposure and development, post-exposure may be performed from the viewpoint of increasing the degree of hardening of the interlayer insulating layer. The exposure amount in post-exposure is preferably 0.2 to 10 J / cm ２ A more preferable 0.5 to 5 J / cm ２ That is the case.

[0139] There are no particular restrictions on the shape of the via. In terms of cross-sectional shape, examples include a square or an inverted trapezoid. Note that an inverted trapezoid is a shape in which the top side is longer than the bottom side. In terms of plan view, examples include a circle or a square. In the photolithography method of via formation in this embodiment, vias with an inverted trapezoidal cross-section can be formed. Vias having this shape are preferable because they have high adhesion of plated copper to the via wall surface. In the photolithography method of via formation in this embodiment, the diameter of the via can be made smaller than the diameter of a via produced by laser processing. The diameter of a via formed by the manufacturing method of this embodiment may be, for example, 40 μm or less, 35 μm or less, or 30 μm or less. There are no particular restrictions on the lower limit of the via diameter, but for example, it may be 15 μm or more, or 20 μm or more.

[0140] (Heat curing step (3)) In heat curing step (3), the interlayer insulating layer having vias is heat cured. That is, in heat curing step (3), heating is used to promote the curing reaction of the thermosetting components contained in the photosensitive resin film of this embodiment. The heating temperature is preferably 100 to 300°C, more preferably 120 to 200°C, and even more preferably 150 to 180°C. The heating time is preferably 0.3 to 3 hours, more preferably 0.5 to 2 hours, and even more preferably 0.75 to 1.5 hours.

[0141] (Circuit pattern formation process (4)) Next, a circuit pattern is formed on the interlayer insulating layer formed above. From the viewpoint of forming fine wiring, it is preferable to form the circuit pattern by a semi-additive process in which roughening treatment, seed layer formation, resist pattern formation, copper circuit layer formation, and resist pattern removal are performed in this order.

[0142] The roughening treatment is a process that roughens the surface of the interlayer insulating layer to form anchors of irregularities. If smearing occurs in the via formation process (2), the roughening treatment and removal of the smear may be performed simultaneously using a roughening solution. Examples of roughening solutions include alkaline permanganate roughening solutions such as sodium permanganate roughening solution; chromium / sulfuric acid roughening solution; sodium fluoride / chromium / sulfuric acid roughening solution.

[0143] Figure 1(c) illustrates the process of forming the seed layer 106. The seed layer 106 is for forming a power supply layer for electrolytic copper plating. The seed layer 106 can be formed by applying electroless copper plating treatment using a palladium catalyst or the like to the via bottom, via wall surface, and the entire surface of the interlayer insulating layer.

[0144] Figure 1(d) illustrates the process of forming a resist pattern 107 on the seed layer 106. The resist pattern 107 can be formed, for example, by heat-pressing a dry film resist onto the seed layer 106 using a roll laminator or the like, and then exposing and developing it. Commercially available dry film resists can be used.

[0145] The dry film resist can be exposed by passing it through a mask on which the desired wiring pattern is drawn. After exposure, the dry film resist is developed using an alkaline aqueous solution to remove unexposed areas and form the resist pattern 107. Subsequently, plasma treatment may be performed to remove any development residue of the dry film resist, if necessary.

[0146] Figure 1(e) illustrates the process of forming a copper circuit layer 108. The copper circuit layer 108 is preferably formed by electrolytic copper plating. As the electrolytic copper plating solution used for electrolytic copper plating, commercially available electrolytic copper plating solutions, such as those containing copper sulfate, can be used. After electrolytic copper plating, the resist pattern 107 is removed using an alkaline aqueous solution or an amine-based stripping agent, and then flash etching to remove the seed layer 106 between the wirings, removal of the palladium catalyst, etc., are performed as appropriate by known methods. Furthermore, if necessary, a post-bake treatment may be performed to sufficiently heat-cur any unreacted thermosetting components.

[0147] Figure 1(f) shows a multilayer printed circuit board 100A that is formed by repeating the above steps and has a solder resist layer 109 on its outermost surface. The solder resist layer 109 can be formed using a known photosensitive resin film for solder resist.

[0148] The above describes a method for manufacturing a printed circuit board using the photosensitive resin film of this embodiment to form vias. However, since the photosensitive resin film of this embodiment has excellent pattern resolution, it is also suitable for forming cavities for embedding chips or passive elements, for example. The cavities can be suitably formed, for example, in the description of the printed circuit board above, by making the drawing pattern when exposing the photosensitive resin film to form a pattern such that it can form the desired cavity.

[0149] [Semiconductor Package] The semiconductor package of this embodiment is a semiconductor package having the printed circuit board of this embodiment and semiconductor elements. The semiconductor package of this embodiment can be manufactured, for example, by mounting semiconductor elements such as semiconductor chips and memory at predetermined positions on the printed circuit board of this embodiment and sealing the semiconductor elements with a sealing resin or the like.

[0150] The embodiments will be described in more detail below with reference to examples, but the embodiments are not limited to these examples.

[0151] [Method for measuring acid value] The acid value was calculated from the amount of potassium hydroxide solution required to neutralize the substance being measured.

[0152] [Method for Measuring Weight-Average Molecular Weight (Mw)] The weight-average molecular weight (Mw) was measured using the following GPC measuring device and measurement conditions, and then converted using a calibration curve for standard polystyrene. The calibration curve was created using a set of five sample polystyrene samples ("PStQuick MP-H" and "PStQuick B," manufactured by Tosoh Corporation) as standard polystyrene. (GPC Measuring Device) GPC device: High-speed GPC device "HCL-8320GPC", detector: differential refractometer or UV, manufactured by Tosoh Corporation. Column: TSKgel SuperMultipore HZ-H column (column length: 15 cm, column inner diameter: 4.6 mm), manufactured by Tosoh Corporation. (Measurement Conditions) Solvent: Tetrahydrofuran (THF) Measurement temperature: 40°C Flow rate: 0.35 ml / min Sample concentration: 10 mg / THF 5 ml Injection volume: 20 μl

[0153] [Production of Photosensitive Resin Compositions and Photosensitive Resin Films] Examples 1-7, Comparative Examples 1-5 (1) Production of Photosensitive Resin Compositions Each component was blended according to the formulation shown in Table 1 (the units of the numerical values ​​in the table are parts by mass, and in the case of solutions, the amount is on a solid content basis), and kneaded using a three-roll mill and a self-rotating mixer. Then, methyl ethyl ketone was added so that the solid content concentration was 65% by mass to obtain a photosensitive resin composition.

[0154] (2) A polyethylene terephthalate film with a manufacturing thickness of 25 μm (manufactured by Toyobo Co., Ltd., trade name "Toyobo Ester HPE") was prepared as a carrier film. The photosensitive resin composition prepared in each example was applied onto the carrier film so that the film thickness after drying was 25 μm, and a photosensitive resin film was formed by drying it at 100°C for 10 minutes using a hot air convection dryer. Subsequently, a polyethylene film (manufactured by Unitika Ltd., trade name "TRFA") was laminated as a protective film onto the surface of the photosensitive resin film opposite to the side in contact with the carrier film, and a photosensitive resin film was prepared by laminating the carrier film and the protective film.

[0155] [Method for measuring relative permittivity (Dk) and dielectric loss tangent (Df)] Two photosensitive resin films, with the protective film removed, are bonded together, and with the carrier films on both sides still attached, they are exposed to light at 400 mJ / cm² using a flatbed exposure machine. ２ , using a UV conveyor type exposure machine at 2 J / cm ２ The material was irradiated. Then, it was heat-treated at 170°C for 1 hour using a hot air circulating dryer, and cut into 7cm x 10cm pieces to be used as evaluation samples. The obtained evaluation samples were sealed with a desiccant and dried for more than 10 hours, and the relative permittivity (Dk) and dielectric loss tangent (Df) in the 10GHz band were measured using the split-post dielectric resonator method (SPDR method) and evaluated based on the following criteria: (Evaluation criteria for relative permittivity (Dk)) A: Less than 3.2 B: 3.2 or more, 3.3 or less C: Greater than 3.3 (Evaluation criteria for dielectric loss tangent (Df)) A: Less than 0.009 B: 0.009 or more, 0.010 or less C: Greater than 0.010

[0156] [Measurement of Minimum Development Time] The copper foil surface of a printed circuit board substrate (manufactured by Resonac Co., Ltd., product name "MCL-E-679"), which consists of copper foil (thickness 12 μm) laminated on a glass epoxy substrate, was pre-treated with a roughening pre-treatment solution (manufactured by MEC Co., Ltd., product name "CZ-8101"), then washed with water and dried. Next, a photosensitive resin film, from which the protective film had been peeled off, was laminated onto the copper foil of the pre-treated printed circuit board substrate with the photosensitive resin film facing the adhesive surface. A press-type vacuum laminator (manufactured by Meiki Seisakusho Co., Ltd., product name "MVLP-500") was used for lamination, and the lamination conditions were: atmospheric pressure 4 kPa or less, vacuuming time 20 seconds, press hot plate temperature 75°C, lamination press time 30 seconds, and pressure 0.4 MPa. After lamination, the laminate was left at room temperature for at least one hour to obtain an evaluation laminate in which a photosensitive resin film and a carrier film were laminated in that order on the copper foil surface of a printed circuit board substrate. The carrier film of the evaluation laminate obtained above was removed, and the photosensitive resin film was spray-developed using a 1% by mass sodium carbonate aqueous solution at 30°C. At this time, the minimum development time was defined as the minimum development time, and it was evaluated based on the following criteria: (Evaluation criteria) A: Minimum development time is less than 20 seconds. B: Minimum development time is 20 seconds or more and 40 seconds or less. C: Minimum development time is more than 40 seconds.

[0157] [Method for measuring adhesion strength to plated copper] (1) Sensitivity measurement of photosensitive resin film An evaluation laminate was prepared using the same procedure as in [Measurement of minimum development time] above, and 41 step tablets were placed on the carrier film of the evaluation laminate. Next, exposure was performed using a parallel light exposure machine (manufactured by Oak Manufacturing Co., Ltd., product name "EXM-1201") with an ultra-high pressure mercury lamp as the light source. After exposure, the film was left at room temperature for 30 minutes, then the carrier film of the evaluation laminate obtained above was removed, and the photosensitive resin film was spray developed using a 1% by mass sodium carbonate aqueous solution at 30°C. The amount of exposure energy at which the number of remaining gloss steps was 8.0 was determined, and this was used as the sensitivity of the photosensitive resin film (unit: mJ / cm). ２) (2) Exposure and Development Process The entire surface of the evaluation laminate was exposed with the exposure energy amount that was the sensitivity determined above, and the photosensitive resin film was cured. After exposure, it was left at room temperature for 30 minutes, then the carrier film of the evaluation laminate was peeled off and the photosensitive resin film was spray developed using a 1% by mass sodium carbonate aqueous solution at 30°C for a development time twice the minimum development time. (3) Post-Cure Treatment Subsequently, using a high-pressure mercury lamp irradiation type UV conveyor device (manufactured by Oak Manufacturing Co., Ltd.), the exposure amount was 2 J / cm ２ Post-UV curing was performed at the conveyor speed. Then, using a hot air circulating dryer, the laminate was heated at 170°C for 1 hour to cure the photosensitive resin film and obtain an evaluation laminate having an interlayer insulating layer. (4) Roughening treatment The evaluation laminate having the obtained interlayer insulating layer was treated with the swelling solution "Swelling Dip Securigant P" at 70°C for 5 minutes and then washed with water. Next, it was roughened with the roughening solution "Dosing Securigant P500J" at 60°C for 15 minutes and then washed with water at 50°C for 1 minute. Subsequently, it was neutralized with the neutralizing solution "Reduction Conditioner Securigant P500" at 50°C for 5 minutes and then washed with water. After that, it was treated with buffered hydrofluoric acid "LAL1800 SA High Purity Buffered Hydrofluoric Acid" at room temperature for 10 minutes and then washed with water. The swelling solution, roughening solution, and neutralizing solution were all manufactured by Atotec Japan Co., Ltd., and the buffered hydrofluoric acid was manufactured by Stella Chemifa Co., Ltd. (5) Plating Treatment The evaluation laminate after the roughening treatment was subjected to electroless plating treatment at 30°C for 15 minutes using the electroless plating solution "Print Gun MSK-DK" (manufactured by Atotec Japan Co., Ltd.), and then rinsed with water. Subsequently, the evaluation laminate with electroless plating was dried in a dryer at 150°C for 30 minutes. Then, electroplating treatment was performed at 24°C and 2 A / dm using the electroplating solution "Caparaside HL" (manufactured by Atotec Japan Co., Ltd.) ２This was done for 1.5 hours. After that, it was annealed in a 150°C dryer for 1 hour to form plated copper on the interlayer insulating layer. The thickness of the plated copper was 25 μm. (6) Measurement of adhesion strength with plated copper The adhesion strength with plated copper was measured by vertical peel strength at 23°C in accordance with JIS C 6481:1996 and evaluated based on the following criteria. (Evaluation criteria) A: Adhesion strength with plated copper is greater than 0.45 kN / m. B: Adhesion strength with plated copper is 0.30 kN / m or more and 0.45 kN / m or less. C: Adhesion strength with plated copper is less than 0.30 kN / m.

[0158]

[0159] The components used in Table 1 are as follows: [Component (A)] Compound having a carboxyl group and an acryloyl group: Manufactured by Nippon Kayaku Co., Ltd., trade name "ZXR-1807H", acid value: 100 mg KOH / g, weight-average molecular weight (Mw): 2,000, a compound having a carboxyl group and an acryloyl group, and containing an alicyclic skeleton represented by the above general formula (A-1).

[0160] [Component (B)] ・Allyl resin 1 having an isocyanurate ring: Manufactured by Shikoku Chemicals, Ltd., trade name "L-DAIC", a compound having one isocyanurate ring and two allyl groups, a compound represented by the above general formula (B-1a-1), boiling point 170°C or higher ・Allyl resin 2 having a glycoluryl ring: Manufactured by Shikoku Chemicals, Ltd., trade name "TA-G", a compound having one glycoluryl ring and four allyl groups, a compound represented by the above general formula (B-2a), boiling point 170°C or higher ・Allyl resin 3 having an isocyanurate ring: Manufactured by Shikoku Chemicals, Ltd., trade name "DD-1", a compound having two isocyanurate rings and four allyl groups, a compound represented by the above general formula (B-1a-2), boiling point 170°C or higher

[0161] [Component (C)] Maleimide resin containing an indane skeleton: Aromatic bismaleimide resin having an indane skeleton, compound represented by the above general formula (C-2)

[0162] [Comparative components] ・Biphenyl aralkyl maleimide resin: Manufactured by Nippon Kayaku Co., Ltd., product name "MIR-3000" ・Bisallyl nadiimide compound: Manufactured by Maruzen Petrochemical Co., Ltd., product name "BANI-X"

[0163] [Component (D)] Trimethylolpropane triacrylate

[0164] [(E) Component] Silica: Molten spherical silica, volume average particle size (D ５０ ): 0.5 μm

[0165] [Component (F)] Organic peroxide: 1,3-di(t-butylperoxyisopropyl)benzene

[0166] [Component (G)] • Photopolymerization initiator: Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide

[0167] [(H) Components] ・Epoxy resin: Naphthol-type epoxy resin: Manufactured by Nippon Steel & Sumitomo Metal Corporation, product name "ESN-475V", epoxy group equivalent: 325 g / eq ・Isocyanate resin: Hexamethylene diisocyanate

[0168] [(I) Components] • Curing accelerator: 1-benzyl-2-phenylimidazole

[0169] [(J) Components] Sensitizer: 4,4'-bis-(diethylamino)benzophenone Polymerization inhibitor: t-butylcatechol

[0170] Table 1 shows that the photosensitive resin compositions of Examples 1 to 7 of this embodiment all exhibit excellent chemical resistance and conductor adhesion.

[0171] 100A Multilayer Printed Wiring Board 101 Substrate 102 Circuit Pattern 103 Photosensitive Layer 104 Interlayer Insulation Layer 105 Via 106 Seed Layer 107 Resist Pattern 108 Copper Circuit Layer 109 Solder Resist Layer

Claims

1. A photosensitive resin composition comprising: (A) a photopolymerizable compound having an ethylenically unsaturated group and an acidic substituent; (B) a compound having an isocyanurate ring or a glycoluryl ring and an ethylenically unsaturated group; and (C) a maleimide resin having a group containing a fused ring of an aromatic ring and an aliphatic ring and two or more N-substituted maleimide groups.

2. The photosensitive resin composition according to claim 1, wherein component (B) has an allyl group as the ethylenically unsaturated group.

3. The photosensitive resin composition according to claim 2, wherein the component (B) is a compound represented by the following general formula (B-1) or a compound represented by the following general formula (B-2). (In the formula, R Ｂ１ , R Ｂ２ and R Ｂ３ are each independently a hydrogen atom or an organic group, and at least one of R Ｂ１ , R Ｂ２ and R Ｂ３ is an allyl group.) (In the formula, R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ are each independently a hydrogen atom or an organic group, and at least one of R Ｂ４ , R Ｂ５ , R Ｂ６ and R Ｂ７ is an allyl group.) 4. The photosensitive resin composition according to any one of claims 1 to 3, wherein the group comprising a condensed ring of an aromatic ring and an aliphatic ring in component (C) is a group comprising an indan ring as the condensed ring.

5. The photosensitive resin composition according to claim 4, wherein the group containing the indan ring is a divalent group represented by the following general formula (C-1). (In the formula, R Ｃ１ This is an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. Ｃ１ R is an integer between 0 and 3. Ｃ２ ~R Ｃ４ Each of these is an alkyl group having 1 to 10 carbon atoms. (* indicates a bonding site.) 6. The photosensitive resin composition according to any one of claims 1 to 3, wherein the content of component (B) is 1 to 50% by mass relative to 100% by mass of the resin component in the photosensitive resin composition.

7. The photosensitive resin composition according to any one of claims 1 to 3, wherein the content of component (C) is 1 to 50% by mass relative to 100% by mass of the resin component in the photosensitive resin composition.

8. The photosensitive resin composition according to any one of claims 1 to 3, wherein the ratio of the content of component (B) to the content of component (C) [component (B) / component (C)] is 0.1 to 10 by mass.

9. A photosensitive resin composition according to any one of claims 1 to 3, used for forming an interlayer insulating layer having photovias.

10. A photosensitive resin film comprising the photosensitive resin composition according to any one of claims 1 to 3.

11. A printed circuit board comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 3.

12. A semiconductor package comprising a printed circuit board according to claim 11 and a semiconductor element.

13. A method for manufacturing a printed circuit board, comprising the following (1) to (4): (1) Laminating the photosensitive resin film described in claim 10 to one or both sides of a circuit board; (2) Forming an interlayer insulating layer having vias by exposing and developing the photosensitive resin film laminated in (1); (3) Heat-curing the interlayer insulating layer having vias; (4) Forming a circuit pattern on the interlayer insulating layer.

Images