Photosensitive resin composition

Abstract

To provide a photosensitive resin composition or the like that can give a cured product having excellent residual film properties and dielectric properties.SOLUTION: A photosensitive resin composition contains (A) a polyimide precursor, (B) a compound having a divalent aliphatic hydrocarbon group with 8 or more carbon atoms, optionally having two ethylenically unsaturated bonds and a substituent, (C) a crosslinker having three or more functional groups, and (D) a photoradical generator.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a photosensitive resin composition. Furthermore, it relates to a photosensitive film, a semiconductor package substrate, a semiconductor device, and a method for manufacturing a semiconductor package substrate obtained by using the photosensitive resin composition.

Background Art

[0002] Conventionally, polyimide resins having excellent heat resistance and insulation properties have been used for insulating layers and the like of semiconductor devices. Further, since polyimide resins have low solubility in solvents, in photosensitive resin compositions, they are used in the state of polyimide precursors, and after forming an insulating layer or the like, the polyimide precursor is cyclized to form an insulating layer (Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Disclosure of the Invention

Problems to be Solved by the Invention

[0004] In recent years, with the increase in communication speed and capacity in communication devices, excellent dielectric properties such as low dielectric constant and low dielectric tangent of the cured product have been required for the photosensitive resin composition used in the semiconductor package substrate of communication devices. Further, in order to form an appropriate pattern, good pattern remaining film properties after exposure and development processes are also required.

[0005] The present invention has been made in view of the above problems, and an object thereof is to provide a photosensitive resin composition excellent in remaining film properties and dielectric properties of the cured product, a photosensitive film, a semiconductor package substrate, a semiconductor device, and a method for manufacturing a semiconductor package substrate obtained by using the photosensitive resin composition.

Means for Solving the Problems

[0006] As a result of intensive studies by the present inventors, it has been found that the above problems can be solved by incorporating a polyimide precursor, a specific compound having an ethylenically unsaturated bond and an aliphatic hydrocarbon group, a crosslinking agent having a functionality of 3 or more, and a photo radical generator into a photosensitive resin composition, and the present invention has been completed.

[0007] That is, the present invention includes the following. [1] A photosensitive resin composition containing (A) a polyimide precursor, (B) a compound having two ethylenically unsaturated bonds and a divalent aliphatic hydrocarbon group having 8 or more carbon atoms which may have a substituent, (C) a crosslinking agent having a functionality of 3 or more, and (D) a photo radical generator. [2] The photosensitive resin composition according to [1], further containing (E) a sensitizer. [3] The photosensitive resin composition according to [1] or [2], wherein the component (B) includes a compound represented by the following formula (B-1). [Chemical formula] (In the formula, R 1b and R 2b each independently represent a hydrogen atom or a methyl group. nb represents an integer of 8 to 20.) [4] The photosensitive resin composition according to any one of [1] to [3], wherein the component (A) has a structural unit represented by the following formula (A-1). [Chemical formula] (In the formula, A each independently represents a tetravalent organic group, B each independently represents a divalent organic group, R 1 and R 2 each independently represent a hydrogen atom or a monovalent organic group. n represents an integer of 5 to 200.) [5] The photosensitive resin composition according to [4], wherein at least one of R 1 and R 2 in the formula (A-1) is a radical reactive group. [6] The photosensitive resin composition according to [5], wherein the radical-reactive group is represented by the following formula (A-2). [Chemical formula] (In the formula, R 4 ~R 6 each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and p represents an integer of 1 to 10.) [7] The photosensitive resin composition according to any one of [4] to [6], wherein B in the formula (A-1) is each independently a divalent organic group having an indane skeleton. [8] The photosensitive resin composition according to any one of [1] to [7], wherein the component (A) has a structural unit represented by the following formula (A-3). [Chemical formula] (In the formula, A1 each independently represents a tetravalent organic group, R 11 and R 12 each independently represents a hydrogen atom or a monovalent organic group, R 13 each independently represents a hydrogen atom or a methyl group, Xa each independently represents a single bond, a group represented by the following formula (1), or a group represented by formula (2), and Xb each independently represents a single bond, a group represented by formula (3), or a group represented by formula (4). m1 represents an integer of 1 to 5, and n1 represents an integer of 5 to 200.) [Chemical formula] (In formulas (1) to (4), * represents a bond.) [9] A photosensitive film in which a photosensitive resin composition layer made of the photosensitive resin composition according to any one of [1] to [8] is formed on a support.

[10] A semiconductor package substrate including an insulating layer formed of a cured product of the photosensitive resin composition according to any one of [1] to [8].

[11] A semiconductor device including the semiconductor package substrate according to

[10] .

[12] A step of forming a photosensitive resin composition layer containing the photosensitive resin composition according to any one of [1] to [8] on a circuit board, A step of irradiating the photosensitive resin composition layer with actinic rays, A step of developing the photosensitive resin composition layer, and a method for manufacturing a semiconductor package substrate including the steps.

Advantages of the Invention

[0008] According to the present invention, there can be provided a photosensitive resin composition excellent in residual film properties and dielectric properties of a cured product, a photosensitive film, a semiconductor package substrate, a semiconductor device, and a method for manufacturing a semiconductor package substrate obtained by using the photosensitive resin composition.

Embodiments for Carrying Out the Invention

[0009] Hereinafter, the photosensitive resin composition, photosensitive film, semiconductor package substrate, semiconductor device, and method for manufacturing a semiconductor package substrate of the present invention will be described in detail. In the following description, the "dielectric constant" represents the "relative dielectric constant" unless otherwise specified.

[0010] [Photosensitive Resin Composition] The photosensitive resin composition of the present invention contains (A) a polyimide precursor, (B) a compound having two ethylenically unsaturated bonds and a divalent aliphatic hydrocarbon group having 8 or more carbon atoms which may have a substituent, (C) a crosslinking agent having three or more functional groups, and (D) a photo radical generator. By combining the components (A) to (D) and containing them in the photosensitive resin composition, a cured product excellent in residual film properties and dielectric properties can be obtained.

[0011] The photosensitive resin composition of the present invention is suitable as a negative photosensitive resin composition.

[0012] The photosensitive resin composition may further contain optional components in combination with the components (A) to (D). Examples of the optional components include (E) a sensitizer, (F) other additives, and (G) a solvent. Hereinafter, each component contained in the photosensitive resin composition will be described in detail.

[0013] <(A) Polyimide Precursor> The photosensitive resin composition contains, as component (A), a (A) polyimide precursor. By including component (A) in the photosensitive resin composition, a cured product with excellent dielectric properties can be obtained. Component (A) may be used alone or in combination of two or more.

[0014] (A) component can use a resin having a plurality of amic acid structures and / or amic acid ester structures. Specifically, a compound obtained by reacting a tetracarboxylic dianhydride and a diamine compound can be used.

[0015] Among them, as component (A), from the viewpoint of obtaining a cured product with excellent residual film properties and excellent dielectric properties, it preferably has a radical reactive group. Examples of the radical reactive group include a vinyl group, an allyl group, a propargyl group, a butenyl group, an ethynyl group, a phenylethynyl group, a maleimide group, a nadimide group, a (meth)acryloyl group, a group represented by formula (A-2) described later, etc., and a group represented by formula (A-2) is preferred. The “(meth)acryloyl group” includes a methacryloyl group, an acryloyl group, and combinations thereof. Also, as component (A), from the viewpoint of obtaining a cured product with excellent residual film properties and excellent dielectric properties, a polyimide precursor having an indane skeleton is preferred, and a polyimide precursor having an indane skeleton and a radical reactive group is more preferred. As the polyimide precursor having an indane skeleton, a compound having an indane skeleton and obtained by reacting a tetracarboxylic dianhydride and a diamine compound can be used. The indane skeleton represents the skeleton shown in the following (a1), and is preferably the trimethylindane skeleton shown in the following formula (a2).

Chemical formula

[0016] Examples of the tetracarboxylic dianhydride include, for example, aliphatic tetracarboxylic dianhydrides and aromatic tetracarboxylic dianhydrides, with aliphatic tetracarboxylic dianhydrides being preferred. Examples of the tetracarboxylic dianhydride include, for example, 4,4'-oxydiphthalic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, 3,4,9,10-perylene tetracarboxylic dianhydride, 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-paraterphenyl tetracarboxylic dianhydride, 3,3',4,4'-metaterphenyl tetracarboxylic dianhydride, 1,2,4,5-cyclohexane tetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, bicyclo[2.2.1]heptane-2-endo-3-endo-5-exo-6-exo-2,3,5,6-tetracarboxylic dianhydride, bicyclo[2.2.1]heptane-2-exo-3-exo-5-exo-6-exo-2,3,5,6-tetracarboxylic dianhydride, bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic dianhydride, decahydro-dimethanonaphthalene tetracarboxylic dianhydride, bis[2-(3-aminopropoxy)ethyl]ether, 1,4-butanediol-bis(3-aminopropyl)ether, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraspiro-5,5-undecane, 1,2-bis(2-aminoethoxy)ethane, 1,2-bis(3-aminopropoxy)ethane, triethylene glycol-bis(3-aminopropyl)ether, polyethylene glycol-bis(3-aminopropyl)ether, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraspiro-5,5-undecane, 1,4-butanediol-bis(3-aminopropyl)ether, and the like.

[0017] As the diamine compound, for example, when the component (A) is a polyimide precursor having an indane skeleton, a diamine having an indane skeleton is used. Examples of the diamine having an indane skeleton include the diamines exemplified below. [Chemical formula]

[0018] From the viewpoint of obtaining a cured product excellent in residual film properties and dielectric properties, the component (A) preferably has a structural unit represented by the following formula (A-1). [Chemical formula] (In the formula, each A independently represents a tetravalent organic group, each B independently represents a divalent organic group, R 1 and R 2 each independently represent a hydrogen atom or a monovalent organic group. n represents an integer of 5 to 200.)

[0019] In formula (A-1), each A independently represents a tetravalent organic group. As the tetravalent organic group, a tetravalent organic group having 6 to 40 carbon atoms is preferable. Examples of the tetravalent organic group having 6 to 40 carbon atoms include, for example, a -COOR 1 group and a -COOR 2 group, an aromatic group in which a -CONH- group is ortho to each other, or an alicyclic aliphatic group (R 1 and R 2 are the same as R 1 and R 2 in formula (A-1).). Examples of such groups include the groups of (i) to (ix). Among them, as A, the following exemplified tetravalent organic groups are preferable, and the group of (viii) and the group of (ix) are more preferable. In the formula, * represents a bond. [Chemical formula]

[0020] In formula (A-1), each B independently represents a divalent organic group. The divalent organic group preferably has an aromatic ring, more preferably has a divalent organic group having an indane skeleton, and even more preferably has an aromatic ring in addition to the indane skeleton. Examples of the divalent organic group include the groups (1a) to (27a) exemplified below, and the groups (1a) to (7a) (divalent organic groups having an indane skeleton) are preferred, and the group (7a) is more preferred. In the formula, * represents a bond.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0021] R in formula (A-1) 1 and R 2 each independently represents a hydrogen atom or a monovalent organic group. Examples of the monovalent organic group include a saturated aliphatic group having 1 to 4 carbon atoms; a reactive group that can be polymerized by a radical generated by heat or light, that is, a radical-reactive group, etc., and it is preferably a radical-reactive group. The radical-reactive group is as described above. R in formula (A-1) 1 and R 2 are each independently preferably at least one is a radical-reactive group, and more preferably both are radical-reactive groups. As the radical-reactive group, a group represented by the following formula (A-2) is preferred.

Chemical formula

[0022] R in formula (A-2) 4 ~R6 each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms. Examples of the aliphatic hydrocarbon group having 1 to 3 carbon atoms include an alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, etc., and among them, a methyl group is preferable.

[0023] As the saturated aliphatic group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms is preferable, and examples thereof include a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, an n-butyl group, etc. R 1 and R 2 at least one of them preferably represents an alkyl group having 1 to 4 carbon atoms or a radical-reactive group.

[0024] In formula (A-2), p represents an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 2.

[0025] In formula (A-1), R 1 and R 2 each independently is preferably such that at least one of them is a radical-reactive group, more preferably at least one of them is a group represented by formula (A-2), and even more preferably both R 1 and R 2 are both groups represented by formula (A-2).

[0026] In formula (A-1), n represents an integer of 5 to 200, preferably an integer of 5 to 150, more preferably an integer of 5 to 100, even more preferably an integer of 5 to 70, an integer of 10 to 170, or an integer of 50 to 150.

[0027] Component (A) preferably has a structural unit represented by formula (A-3).

Chemical formula

[0028] In formula (A-3), A1 each independently represents a tetravalent organic group, and A1 is the same as A in formula (A-1).

[0029] R in formula (A-3) 11 and R 12 each independently represents a hydrogen atom or a monovalent organic group, and R 1 and R 2 in formula (A-1) are the same as each other.

[0030] Xa each independently represents a single bond, a group represented by formula (1), or a group represented by formula (2).

[0031] Examples of the group represented by formula (1) include a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group.

[0032] Examples of the group represented by formula (2) include the following groups (2-1) to (2-6). [Chemical formula]

[0033] Among them, as Xa, a group represented by formula (2) is preferable, and the group of (2-1) is more preferable.

[0034] Xb each independently represents a single bond, a group represented by formula (3), or a group represented by formula (4).

[0035] Examples of the group represented by formula (3) include a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, and the like.

[0036] Examples of the group represented by formula (4) include the following groups. [Chemical formula]

[0037] Among them, as Xb, a group represented by formula (3) is preferable, and a 1,4-phenylene group is more preferable.

[0038] R 13 each independently represents a hydrogen atom or a methyl group, and preferably represents a methyl group.

[0039] m1 represents an integer of 1 to 5, preferably represents an integer of 1 to 3, more preferably represents 2 or 3, and even more preferably represents 3.

[0040] n1 represents an integer of 5 to 200 and is the same as n in formula (A-1).

[0041] Component (A) preferably has a structural unit represented by the following (A-4). [Chemical formula] (In the formula, A2 each independently represents a tetravalent organic group, and R 21 or R 22 each independently represents a hydrogen atom or a group represented by the following formula (A-5). n2 represents an integer of 5 to 200.) [Chemical formula] (In the formula, R 14 ~R 16 each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and p1 represents an integer of 1 to 10.)

[0042] In formula (A-4), each A2 independently represents a tetravalent organic group, which is the same as A in formula (A-1).

[0043] R in formula (A-4) 21 and R 22 each independently represent a hydrogen atom or a group represented by formula (A-5), and the group represented by formula (A-5) is preferred. R in the group represented by formula (A-5) 14 ~R 16 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, which is the same as R in the group represented by formula (A-2). p1 in the group represented by formula (A-5) represents an integer of 1 to 10, which is the same as p in the group represented by formula (A-2). 4 ~R 6 n2 represents an integer of 5 to 200, which is the same as n in formula (A-1).

[0044]

[0045] Component (A) may be a copolymer containing a structural unit having an indane skeleton and a structural unit not containing an indane skeleton in addition to the structural unit having an indane skeleton. For example, component (A) may contain, in addition to the structural unit containing an indane skeleton represented by formula (A-1), a structural unit not containing an indane skeleton represented by formula (A-1).

[0046] Specific examples of component (A) include the following compounds (A1) to (A6). However, component (A) is not limited to these specific examples. In the formula, n represents an integer of 5 to 200.

Chemical formula

Chemical formula

[0047] ​The weight average molecular weight of component (A) is preferably 5000 or more, more preferably 10000 or more, still more preferably 50000 or more, and preferably 1000000 or less, more preferably 500000 or less, still more preferably 200000 or less, from the viewpoint of remarkably obtaining the effects of the present invention. The weight average molecular weight of the resin can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC).

[0048] The production method of component (A) is not particularly limited. Component (A) can usually be obtained by reacting the above-mentioned tetracarboxylic dianhydride and diamine compound. Component (A) can be produced, for example, by the production methods described in JP-A-2015-209461 or JP-A-2015-214680.

[0049] The content of component (A) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, and preferably 90% by mass or less, more preferably 85% by mass or less, still more preferably 80% by mass or less, when the non-volatile components of the photosensitive resin composition are 100% by mass, from the viewpoint of remarkably obtaining the effects of the present invention. In the present invention, the content of each component in the photosensitive resin composition is a value when the non-volatile components in the photosensitive resin composition are 100% by mass, unless otherwise specified.

[0050] The photosensitive resin composition contains, as component (B), a compound having two ethylenically unsaturated bonds and a divalent aliphatic hydrocarbon group having 8 or more carbon atoms which may have a substituent. By using component (B) in combination with component (C) described later in the photosensitive resin composition, it becomes possible to obtain a cured product excellent in residual film properties and dielectric properties. In particular, when a polyimide precursor having an indane skeleton is used as component (A), the effects of the present invention can be remarkably obtained. Component (B) may be used alone or in combination of two or more. Also, those corresponding to the above-described component (A) are excluded from component (B).

[0051] (B) As the component, a compound having two ethylenically unsaturated bonds and a divalent aliphatic hydrocarbon group having 8 or more carbon atoms can be used. The ethylenically unsaturated bond represents a carbon-carbon double bond. Therefore, component (B) may contain a group having an ethylenically unsaturated bond (hereinafter, may be appropriately referred to as an "ethylenically unsaturated group"). The ethylenically unsaturated group is usually a monovalent group, and examples thereof include a vinyl group, an allyl group, a propargyl group, a butenyl group, an ethynyl group, a phenylethynyl group, a maleimide group, a nadimide group, and a (meth)acryloyl group. From the viewpoint of the reactivity of photoradical polymerization, a (meth)acryloyl group and a phenylethynyl group are preferable, and a (meth)acryloyl group is particularly preferable. Since component (B) contains an ethylenically unsaturated bond, photoradical polymerization is possible. Component (B) functions as a crosslinking agent in the same manner as component (C). Also, the two ethylenically unsaturated groups in component (B) may be the same or different.

[0052] The number of carbon atoms of the divalent aliphatic hydrocarbon group having 8 or more carbon atoms is 8 or more, preferably 9 or more, from the viewpoint of improving the residual film properties. As the upper limit, from the viewpoint of improving solubility, it is preferably 20 or less, more preferably 15 or less, and still more preferably 12 or less.

[0053] Examples of the divalent aliphatic hydrocarbon group having 8 or more carbon atoms include an alkylene group having 8 or more carbon atoms, an alkenylene group having 8 or more carbon atoms, an alkynylene group having 8 or more carbon atoms, etc., and an alkylene group having 8 or more carbon atoms is preferable.

[0054] Examples of the alkylene group having 8 or more carbon atoms include an octylene group, a nonylene group, a decylene group, an undecylene group, a dodecylene group, etc. Examples of the alkenylene group having 8 or more carbon atoms include an octenylene group, a nonenylene group, a decenylene group, an undecenylene group, a dodecenylene group, etc. Examples of the alkynylene group having 8 or more carbon atoms include an octenylene group, a nonenylene group, a decenylene group, an undecenylene group, a dodecenylene group, etc.

[0055] The divalent aliphatic hydrocarbon group having 8 or more carbon atoms may have a substituent. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom; a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group; a hydroxy group; a halogen atom-substituted alkyl group such as a trifluoromethyl group, etc., and a halogen atom is preferable. The above-mentioned substituent may further have a substituent (hereinafter sometimes referred to as a "secondary substituent"). The substituents may be included alone or in combination of two or more.

[0056] As the component (B), a compound represented by the following formula (B-1) is preferable.

Chemical formula

[0057] R 1b and R 2bEach independently represents a hydrogen atom or a methyl group, and a methyl group is preferred. R 1b and R 2b It is preferred that at least one of them is a methyl group, and more preferably both are methyl groups.

[0058] nb represents an integer of 8 or more and 20 or less, preferably 9 or more. The upper limit is preferably 15 or less, more preferably 12 or less.

[0059] Specific examples of component (B) include the following compounds (B1) to (B3). However, component (B) is not limited to these specific examples.

Chemical formula

[0060] From the viewpoint of significantly obtaining the effects of the present invention, the content of component (B) is preferably 1 part by mass or more, more preferably 3 parts by mass or more, still more preferably 4 parts by mass or more, and preferably 25 parts by mass or less, more preferably 20 parts by mass or less, still more preferably 15 parts by mass or less with respect to 100 parts by mass of component (A).

[0061] From the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile components of the photosensitive resin composition are 100% by mass, the content of component (B) is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less.

[0062] <(C) Crosslinking agent having three or more functional groups> The photosensitive resin composition contains a crosslinking agent having three or more functional groups as component (C). However, those corresponding to the above-mentioned components (A) and (B) are excluded from component (C). By including component (C) in the photosensitive resin composition in combination with component (B), it becomes possible to obtain a cured product having excellent residual film properties and excellent dielectric properties. In particular, when a polyimide precursor having an indane skeleton is used as component (A), the effects of the present invention can be remarkably obtained. Component (C) may be used alone or in combination of two or more.

[0063] (C) component usually contains three or more structures capable of reacting with an ethylenically unsaturated bond per molecule. Examples of the structure capable of reacting with an ethylenically unsaturated bond include a group having an ethylenically unsaturated bond. That is, component (C) is preferably a compound having three or more ethylenically unsaturated groups. The ethylenically unsaturated bond is as described above. The preferred ethylenically unsaturated groups in component (C) are the same as those in component (B). From the viewpoint of the reactivity of photoradical polymerization, a (meth)acryloyl group and a phenylethynyl group are preferred, and a (meth)acryloyl group is particularly preferred. The number of structures of component (C) capable of reacting with an ethylenically unsaturated bond per molecule is usually 3 or more, preferably 4 or more, preferably 8 or less, more preferably 6 or less, and still more preferably 5 or less. When component (C) contains three or more ethylenically unsaturated groups per molecule, those ethylenically unsaturated groups may be the same or different. As component (C), a compound having three or more ethylenically unsaturated bonds per molecule and at least one of the carbon atoms at the α-position of the ethylenically unsaturated bond being bonded to a carbonyl group or an aromatic group is preferred. The carbon atom at the α-position of the ethylenically unsaturated bond refers to the first carbon atom adjacent to the carbon atom bonded by a carbon-carbon double bond.

[0064] As component (C), a compound represented by the following general formula (C-1) is preferred.

Chemical formula

[0065] R 1c each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Examples of the linear or branched alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1-butyl group, an s-butyl group, a t-butyl group, etc. Among them, R 1c is preferably a hydrogen atom or a methyl group.

[0066] Z 1c each independently represents a linear or branched alkylene group having 1 to 20 carbon atoms which may contain an oxygen atom, an arylene group which may contain an oxygen atom, or a linear or branched alkenylene group having 2 to 20 carbon atoms which may contain an oxygen atom. As the linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkylene group having 1 to 10 carbon atoms is preferable, and a linear or branched alkylene group having 1 to 6 carbon atoms is more preferable. Examples of such an alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, etc., and a methylene group is preferable. The alkylene group may also be an oxyalkylene group containing an oxygen atom, and specific examples of such a group include those shown below. In the formula, "*" represents a bond, and a represents an integer of 1 to 23.

Chemical formula

[0067] The arylene group which may contain an oxygen atom is preferably an arylene group having 6 to 20 carbon atoms, more preferably an arylene group having 6 to 15 carbon atoms, and even more preferably an arylene group having 6 to 10 carbon atoms. Examples of such arylene groups include a phenylene group and a naphthylene group. The arylene group may contain an oxygen atom, and specific examples of such groups include, for example, those shown below. In the formula, “*” represents a bond, and a represents an integer of 1 to 23. [Chemical formula]

[0068] The linear or branched alkenylene group having 2 to 20 carbon atoms which may contain an oxygen atom is preferably a linear or branched alkenylene group having 2 to 10 carbon atoms, and more preferably a linear or branched alkenylene group having 2 to 6 carbon atoms. Examples of such alkenylene groups include an ethenylene group, a propenylene group, a butenylene group, a pentenylene group, and a hexenylene group. The alkenylene group may also be an oxyalkenylene group containing an oxygen atom, and specific examples of such groups include, for example, those shown below. In the formula, “*” represents a bond, and a represents an integer of 1 to 23. The propenylene group is preferred as the alkenylene group. [Chemical formula]

[0069] Among them, Z 1c is preferably a linear or branched alkylene group having 1 to 20 carbon atoms which may contain an oxygen atom, and more preferably a methylene group.

[0070] A 1crepresents a linear, cyclic or branched nc-valent organic group having 1 to 10 carbon atoms. Examples of the nc-valent organic group include an nc-valent hydrocarbon group which may contain an oxygen atom, an nc-valent group derived from bisphenol, an nc-valent group derived from fluorene, an nc-valent group derived from tricyclodecane, or an nc-valent group derived from an isocyanuric group. Examples of the nc-valent hydrocarbon group which may contain an oxygen atom include an nc-valent aliphatic hydrocarbon group which may contain an oxygen atom and an nc-valent aromatic hydrocarbon group which may contain an oxygen atom, and the nc-valent aliphatic hydrocarbon group which may contain an oxygen atom is preferred. A 1c Specific examples of the group represented by are, for example, those shown below. In the formula, “*” represents a bond.

Chemical formula

[0071] nc represents a positive integer of 3 to 6, preferably a positive integer of 3 to 5, more preferably 3 or 4, and still more preferably 4.

[0072] As the component (C), a compound represented by the following general formula (C-2) is preferred.

Chemical formula

[0073] R 2c represents a hydrogen atom or a methyl group, and a methyl group is preferred.

[0074] Z 2c each independently represents a linear or branched alkylene group having 1 to 20 carbon atoms which may contain an oxygen atom, and is the same as Z 1c in the formula (C-1).

[0075] A 2c represents a linear, cyclic or branched tetravalent organic group having 1 to 10 carbon atoms, and A in formula (C-1) 1c is the same as that.

[0076] Specific examples of the component (C) include the following compounds (CL-1) to (CL-6). However, the component (C) is not limited to these specific examples.

Chemical formula

[0077] As the component (C), commercially available products can be used. Examples of commercially available products include NK Ester D-TMP, 4G, 9G, 14G, 23G, DCP, etc. manufactured by Shin-Nakamura Chemical Co., Ltd.

[0078] From the viewpoint of significantly obtaining the effects of the present invention, the content of the component (C) is preferably 1 part by mass or more, more preferably 3 parts by mass or more, still more preferably 5 parts by mass or more, and preferably 20 parts by mass or less, more preferably 15 parts by mass or less, still more preferably 10 parts by mass or less with respect to 100 parts by mass of the component (A).

[0079] From the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile components of the photosensitive resin composition are 100% by mass, the content of the component (C) is preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, and preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less.

[0080] When the non-volatile components of the photosensitive resin composition are 100% by mass, and the content of the component (C) is c1 and the content of the component (B) is b1, from the viewpoint of significantly obtaining the effects of the present invention, b1 / c1 is preferably 0.1 or more, more preferably 0.3 or more, still more preferably 0.5 or more, and preferably 5 or less, more preferably 2 or less, still more preferably 1.5 or less.

[0081] <(D) Photo radical generator> The photosensitive resin composition contains a (D) photo radical generator as the component (D). The component (D) generates radicals upon irradiation with actinic rays, and the crosslinking reaction can proceed by these radicals. In the photosensitive resin composition, the portion where the crosslinking reaction by radicals occurs hardens to become a cured product, and the resistance to the developer is improved. Therefore, it becomes possible to selectively remove the photosensitive resin composition except for the portion where the crosslinking reaction has proceeded during development, and a negative-type pattern can be advantageously formed. The component (D) may be used alone or in combination of two or more. Further, those corresponding to the above-described components (A) to (C) are excluded from the component (D).

[0082] (D) components include benzophenone derivatives such as benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl ketone, dibenzyl ketone, fluorenone; acetophenone derivatives such as 2,2'-diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone; thioxanthone derivatives such as thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone; benzyl derivatives such as benzyl, benzyl dimethyl ketal, benzyl-β-methoxyethyl acetal; benzoin derivatives such as benzoin, benzoin methyl ether; oximes such as 1-phenyl-1,2-butanedione-2-(o-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-benzoyl)oxime, 1,3-diphenylpropanetrione-2-(o-ethoxycarbonyl)oxime, 1-phenyl-3-ethoxypropanetrione-2-(o-benzoyl)oxime; N-aryl glycines such as N-phenylglycine; peroxides such as benzoyl perchloride; aromatic biimidazoles; titanocenes; α-(n-octanesulfonyloxyimino)-4-methoxybenzyl cyanide; etc. Among them, from the viewpoint of photosensitivity, oximes are preferred as the (D) component.

[0083] (D) component can use commercially available products. Examples of commercially available products include "Irgacure - OX02", "Irgacure - OX04" manufactured by BASF.

[0084] (D) component content, from the viewpoint of significantly obtaining the effects of the present invention, is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, still more preferably 1 part by mass or more, and preferably 20 parts by mass or less, more preferably 10 parts by mass or less, still more preferably 5 parts by mass or less, based on 100 parts by mass of the (A) component.

[0085] As for the content of the (D) component, from the viewpoint of remarkably obtaining the effects of the present invention, when the non-volatile components of the photosensitive resin composition are 100% by mass, it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, still more preferably 1% by mass or more, and preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less.

[0086] <(E) Sensitizer> The photosensitive resin composition may contain an (E) sensitizer as an optional component. By containing the (E) sensitizer in the photosensitive resin composition, it becomes possible to improve the photosensitivity of the photosensitive resin composition. The (E) component may be used alone or in combination of two or more. Also, those corresponding to the above-described (A) to (D) components are excluded from the (E) component.

[0087] Component (E) can use a compound capable of improving the photosensitivity of the photosensitive resin composition. Examples of such compounds include benzophenones such as Michler's ketone, 4,4'-bis(diethylamino)benzophenone, and 4-morpholinobenzophenone; cyclic alkanes such as 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, and 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone; chalcones such as 4,4'-bis(dimethylamino)chalcone and 4,4'-bis(diethylamino)chalcone; indanones such as p-dimethylaminocinnamylidene indanone and p-dimethylaminobenzylidene indanone; thiazoles such as 2-(p-dimethylaminophenylbiphenylene)-benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, and 2-(p-dimethylaminophenylvinylene)isonaphthothiazole; acetones such as 1,3-bis(4'-dimethylaminobenzal)acetone and 1,3-bis(4'-diethylaminobenzal)acetone; coumarins such as 3,3'-carbonyl-bis(7-diethylaminocoumarin), 3-acetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, and 3-ethoxycarbonyl-7-diethylaminocoumarin; amines such as N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, N-p-tolyldiethanolamine, N-phenylethanolamine, isoamyl dimethylaminobenzoate, and isoamyl diethylaminobenzoate; heterocyclic compounds such as 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzothiazole, 2-(p-dimethylaminostyryl)naphtho(1,2-d)thiazole, 1-phenyl-5-mercaptotetrazole, and 1-p-hydroxyphenyl-5-mercaptotetrazole; and styrenes such as 2-(p-dimethylaminobenzoyl)styrene.

[0088] Among them, as the (E) component, from the viewpoint of remarkably obtaining the effects of the present invention, a heterocyclic compound is preferable, and a compound represented by the following general formula (E-1) is more preferable.

Chemical formula

[0089] R 1e represents a hydrogen atom, a linear or branched alkyl group having 1 to 7 carbon atoms, a halogen atom, a hydroxy group, a methoxy group, or a t-butoxy group. Examples of the linear or branched alkyl group having 1 to 7 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a t-butyl group, and the like. Among them, R 1e preferably represents a hydroxy group, a methoxy group, or a t-butoxy group having an oxygen atom, preferably a hydrogen atom or a hydroxy group, and more preferably a hydrogen atom.

[0090] R 1e The bonding position of may be any of the ortho position, meta position, and para position with respect to the site of the phenylene group bonded to the nitrogen atom of mercaptotetrazole, but from the viewpoint of remarkably obtaining the effects of the present invention, the para position is preferable.

[0091] The compound represented by (E-1) is preferably either the compound represented by the following (E-2) or the compound represented by the following (E-3).

Chemical formula

[0092] From the viewpoint of significantly obtaining the effects of the present invention, the content of component (E) is preferably 1 part by mass or more, more preferably 2 parts by mass or more, still more preferably 3 parts by mass or more, and preferably 20 parts by mass or less, more preferably 15 parts by mass or less, still more preferably 10 parts by mass or less, based on 100 parts by mass of component (A).

[0093] From the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile components of the photosensitive resin composition are 100% by mass, the content of component (E) is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, and preferably 15% by mass or less, more preferably 10% by mass or less, still more preferably 8% by mass or less.

[0094] <(F) Other Additives> The photosensitive resin composition may further contain (F) other additives to the extent that it does not inhibit the object of the present invention. Examples of (F) other additives include adhesion aids; surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone-based surfactants; thermoplastic resins; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black, and naphthalene black; polymerization inhibitors such as hydroquinone, phenothiazine, methyl hydroquinone, hydroquinone monomethyl ether, catechol, and pyrogallol; thickeners such as benton and montmorillonite; defoamers such as silicone-based, fluorine-based, and vinyl resin-based defoamers; flame retardants such as epoxy resins, antimony compounds, phosphorus-based compounds, aromatic condensed phosphoric acid esters, and halogen-containing condensed phosphoric acid esters; and various additives such as thermosetting resins such as phenolic curing agents and cyanate ester-based curing agents can be added.

[0095] <(G) Solvent> The photosensitive resin composition may contain, as an optional component, (G) a solvent in combination with the above-described non-volatile components such as components (A) to (F). (G) The solvent is a volatile component, and is preferably one that can uniformly dissolve at least any one of components (A) to (D) and components (E) and (F) which are optional components. Examples of such solvents include ether compounds having 2 to 9 carbon atoms such as dimethyl ether, diethyl ether, methyl ethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether; ketone compounds having 2 to 6 carbon atoms such as acetone and methyl ethyl ketone; saturated hydrocarbon compounds having 5 to 10 carbon atoms such as normal pentane, cyclopentane, normal hexane, cyclohexane, methylcyclohexane, and decalin; aromatic hydrocarbon compounds having 6 to 10 carbon atoms such as benzene, toluene, xylene, mesitylene, and tetralin; ester compounds having 3 to 9 carbon atoms such as methyl acetate, ethyl acetate, γ-butyrolactone, and methyl benzoate; halogen-containing compounds having 1 to 10 carbon atoms such as chloroform, methylene chloride, and 1,2-dichloroethane; nitrogen-containing compounds having 2 to 10 carbon atoms such as acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; and sulfur-containing compounds such as dimethyl sulfoxide.

[0096] Further, examples of the component (G) include N-ethyl-2-pyrrolidone, tetrahydrofuran, N,N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, pyridine, cyclopentanone, α-acetyl-γ-butyrolactone, tetramethylurea, 1,3-dimethyl-2-imidazolinone, N-cyclohexyl-2-pyrrolidone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl ethyl ketone, methyl isobutyl ketone, anisole, ethyl acetate, ethyl lactate, and butyl lactate. The component (G) may be used alone or in combination of two or more.

[0097] When the total amount of the photosensitive resin composition including the component (G) is 100% by mass, the content of the component (G) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, preferably 99% by mass or less, more preferably 97% by mass or less, and still more preferably 95% by mass or less. In addition, when the total amount of the photosensitive resin composition including the component (G) is 100% by mass, the content of the component (G) in the photosensitive resin composition layer of the photosensitive film is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, preferably 40% by mass or less, more preferably 35% by mass or less, and still more preferably 30% by mass or less.

[0098] The photosensitive resin composition can be produced by mixing the above components (A) to (D) as essential components, appropriately mixing the above components (E) to (G) as optional components, and kneading or stirring as necessary by kneading means such as a three-roll mill, ball mill, bead mill, sand mill, or stirring means such as a super mixer or planetary mixer.

[0099] <Physical properties and uses of the photosensitive resin composition> The photosensitive resin composition exhibits the property of excellent residual film property. For example, the photosensitive resin composition is applied onto a substrate to form a photosensitive resin composition layer. The photosensitive resin composition layer is exposed and developed. The film thickness residual rate (residual film property) is evaluated by applying it to "the film thickness of the photosensitive resin composition layer after development" / "the film thickness of the photosensitive resin composition layer after coating (before exposure)" × 100 (%). At this time, the residual film property is preferably 60% or more, more preferably 63%, and still more preferably 65% or more. The evaluation of the residual film property can be measured according to the method described in the examples below.

[0100] The cured product obtained by thermally curing the photosensitive resin composition at 170 °C for 3 hours exhibits the property of low dielectric constant (Dk). The dielectric constant at 23 °C is preferably 5 or less, more preferably 4 or less, and still more preferably 3 or less. The lower limit is not particularly limited, and it can be 1 or more, etc. The dielectric constant can be measured according to the method described in the examples below.

[0101] The cured product obtained by thermally curing the photosensitive resin composition at 170 °C for 3 hours exhibits the property of low dielectric tangent (Df). The dielectric tangent at 23 °C is preferably 0.01 or less, more preferably 0.009 or less, and still more preferably 0.008 or less. The lower limit is not particularly limited, and it can be 0.0001 or more, etc. The dielectric tangent can be measured according to the method described in the examples below.

[0102] The use of the photosensitive resin composition of the present invention is not particularly limited, and it can be used in a wide range of applications where a photosensitive resin composition is used, such as photosensitive films, insulating resin sheets such as prepregs, silicon wafers, circuit boards (for laminates, multilayer printed wiring boards, etc.), solder resists, buffer coat films, underfill materials, die bonding materials, semiconductor encapsulants, hole filling resins, component embedding resins, etc. Among them, a photosensitive resin composition for an insulating layer of a printed wiring board (a printed wiring board having a cured product of the photosensitive resin composition as an insulating layer), a photosensitive resin composition for an interlayer insulating layer (a printed wiring board having a cured product of the photosensitive resin composition as an interlayer insulating layer), a photosensitive resin composition for plating formation (a printed wiring board having plating formed on a cured product of the photosensitive resin composition), and a photosensitive resin composition for solder resist (a printed wiring board having a cured product of the photosensitive resin composition as a solder resist), a photosensitive resin composition for a rewiring formation layer of a wafer-level package (a wafer-level package having a cured product of the photosensitive resin composition as a rewiring formation layer), a photosensitive resin composition for a rewiring formation layer of a fan-out wafer-level package (a fan-out wafer-level package having a cured product of the photosensitive resin composition as a rewiring formation layer), a photosensitive resin composition for a rewiring formation layer of a fan-out panel-level package (a fan-out panel-level package having a cured product of the photosensitive resin composition as a rewiring formation layer), a photosensitive resin composition for buffer coat (a semiconductor device having a cured product of the photosensitive resin composition as a buffer coat), and a photosensitive resin composition for an insulating layer for a display (a display having a cured product of the photosensitive resin composition as an insulating layer) can be preferably used.

[0103] [Photosensitive film] The photosensitive resin composition of the present invention can be applied to a photosensitive film. The photosensitive film can include a support and a photosensitive resin composition layer formed on the support. The photosensitive resin composition layer is a layer made of the above-described photosensitive resin composition. Further, the photosensitive film may include a support, a photosensitive resin composition layer, and a protective film in this order.

[0104] Examples of the support include polyethylene terephthalate film, polyethylene naphthalate film, polypropylene film, polyethylene film, polyvinyl alcohol film, triacetyl acetate film, etc., and polyethylene terephthalate film is particularly preferred.

[0105] Examples of commercially available supports include polypropylene films such as the product names "Alpha MA-410" and "E-200C" manufactured by Oji Paper Co., Ltd., the product names "GF-1" and "GF-8" manufactured by Tamapoly Co., Ltd., and those manufactured by Shin-Etsu Film Co., Ltd., and polyethylene terephthalate films such as the product name "PS-25" of the PS series manufactured by Teijin Limited, etc., but are not limited thereto. In order to facilitate removal of these supports, it is preferable that a release agent such as a silicone coating agent or a non-silicone coating agent is applied to the surface. Examples of the support whose surface is treated with such a release agent include "AL-5" manufactured by Lintec Corporation. The thickness of the support is preferably in the range of 5 μm to 100 μm, and more preferably in the range of 10 μm to 50 μm.

[0106] The thickness of the photosensitive resin composition layer is not particularly limited, and can be, for example, 1 μm or more and 100 μm or less. Among them, it is preferably 2 μm or more, more preferably 4 μm or more, preferably 50 μm or less, and more preferably 30 μm or less.

[0107] The photosensitive resin composition layer may be protected with a protective film. By protecting the photosensitive resin composition layer with a protective film, adhesion of dust and scratches to the surface of the photosensitive resin composition layer can be suppressed. As the protective film, for example, a film made of the same material as the above support can be used. The thickness of the protective film is not particularly limited, but is preferably in the range of 1 μm to 40 μm, more preferably in the range of 5 μm to 30 μm, and even more preferably in the range of 10 μm to 30 μm. It is preferable that the adhesive force between the photosensitive resin composition layer and the protective film is smaller than the adhesive force between the photosensitive resin composition layer and the support.

[0108] The photosensitive film can be produced, for example, by applying a photosensitive resin composition onto a support and drying the (G) solvent as necessary.

[0109] [Semiconductor package substrate] The semiconductor package substrate of the present invention includes an insulating layer formed of a cured product of the photosensitive resin composition of the present invention. The insulating layer is preferably used as a rewiring formation layer, an interlayer insulating layer, a buffer coat film, or a solder resist.

[0110] Specifically, the semiconductor package substrate of the first embodiment of the present invention can be manufactured using the above-described photosensitive resin composition, and the cured product of the photosensitive resin composition is used as an insulating layer. Specifically, the method for manufacturing a semiconductor package substrate includes (I) a step of forming a photosensitive resin composition layer containing the photosensitive resin composition of the present invention on a circuit board, (II) a step of irradiating the photosensitive resin composition layer with actinic rays, and (III) a step of developing the photosensitive resin composition layer, in this order.

[0111] <Step (I)> Examples of the method for forming the photosensitive resin composition layer include a method of directly applying a resin varnish containing the photosensitive resin composition onto the circuit board and a method using the photosensitive film.

[0112] When directly applying a resin varnish containing the photosensitive resin composition onto the circuit board, a photosensitive resin composition layer is formed on the circuit board by drying and volatilizing the (G) component.

[0113] Examples of the application method of the resin varnish include, for example, gravure coating method, microgravure coating method, reverse coating method, kiss reverse coating method, die coating method, slot die method, lip coating method, comma coating method, blade coating method, roll coating method, knife coating method, curtain coating method, chamber gravure coating method, slot orifice method, spin coating method, slit coating method, spray coating method, dip coating method, hot melt coating method, bar coating method, applicator method, air knife coating method, curtain flow coating method, offset printing method, brush painting method, full-surface printing method by screen printing method, etc.

[0114] The resin varnish may be applied in several portions, may be applied once, or may be applied by combining a plurality of different methods. Among them, the die coating method, which is excellent in uniform coating properties, is preferable. Also, in order to avoid foreign matter contamination, etc., it is preferable to carry out the coating process in an environment with less generation of foreign matter such as a clean room.

[0115] After applying the resin varnish, drying is carried out using a hot air furnace or an infrared furnace, etc. as necessary. The drying conditions are preferably 80°C to 120°C for 3 minutes to 13 minutes. In this way, a photosensitive resin composition layer is formed on the circuit board.

[0116] Examples of the circuit board include, for example, glass epoxy board, metal board, polyester board, polyimide board, BT resin board, thermosetting polyphenylene ether board, etc. Here, the circuit board refers to a board in which a conductor layer (circuit) subjected to pattern processing is formed on one or both sides of the support board as described above. Also, in a multilayer printed wiring board formed by alternately laminating a conductor layer and an insulating layer, a board in which one or both sides of the outermost layer of the multilayer printed wiring board are conductor layers (circuits) subjected to pattern processing is also included in the circuit board referred to here. Note that the surface of the conductor layer may be previously roughened by blackening treatment, copper etching, etc.

[0117] On the other hand, when using a photosensitive film, the photosensitive resin composition layer side is laminated on one or both sides of the circuit board using a vacuum laminator. In the lamination process, if the photosensitive film has a protective film, the protective film is removed, and then, if necessary, the photosensitive film and the circuit board are preheated, and the photosensitive resin composition layer is pressure-bonded to the circuit board while applying pressure and heat. In the case of a photosensitive film, a method of laminating it on the circuit board under reduced pressure by the vacuum lamination method is preferably used.

[0118] The lamination conditions are not particularly limited. For example, the pressure-bonding temperature (lamination temperature) is preferably 70°C to 140°C, and the pressure-bonding pressure is preferably 1 kgf / cm 2 ~11 kgf / cm 2 (9.8×10 4 N / m 2 ~107.9×10 4 N / m 2 ), the pressure-bonding time is preferably 5 seconds to 300 seconds, and it is preferably laminated under reduced pressure with an air pressure of 20 mmHg (26.7 hPa) or less. Also, the lamination process may be a batch type or a continuous type using a roll. The vacuum lamination method can be carried out using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include the Vacuum Applicator manufactured by Nippon Materials Co., Ltd., the Vacuum Pressure Laminator manufactured by Meiki Seisakusho Co., Ltd., the Roll-Type Dry Coater manufactured by Hitachi Industries Co., Ltd., the Vacuum Laminator manufactured by Hitachi AIC Inc., and the like.

[0119] <Process (II)> After a photosensitive resin composition layer is provided on the circuit board, then, through a mask pattern, an exposure process of irradiating a predetermined portion of the photosensitive resin composition layer with actinic rays is performed. Examples of actinic rays include ultraviolet rays, visible rays, electron beams, X-rays, etc., and ultraviolet rays are particularly preferred. The irradiation amount of ultraviolet rays is generally 10 mJ / cm 2 ~1000 mJ / cm 2This is the case. As for the exposure method, there are a contact exposure method in which a mask pattern is brought into close contact with a circuit board and a non-contact exposure method in which parallel light rays are used for exposure without bringing them into close contact, and either method may be used.

[0120] In step (II), as the mask pattern, for example, a via pattern such as a round hole pattern can be used to form vias. The via diameter (opening diameter) is preferably 100 μm or less, more preferably 50 μm or less, and even more preferably 30 μm or less. The lower limit is not particularly limited, but can be 0.1 μm or more, 0.5 μm or more, etc.

[0121] <Step (III)> After the exposure step, a pattern can be formed by performing a development step of removing the unexposed portion of the photosensitive resin composition layer with a developer. Development is usually performed by wet development.

[0122] In the case of the above wet development, as the developer, a developer that is safe, stable, and has good operability, such as an alkaline solution, an aqueous developer, or an organic solvent, is used. Also, as the development method, known methods such as spraying, rocking immersion, brushing, and scraping are appropriately employed.

[0123] Examples of the alkaline aqueous solution used as the developer include aqueous solutions of alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, carbonates or bicarbonates such as sodium carbonate and sodium bicarbonate, alkali metal phosphates such as sodium phosphate and potassium phosphate, alkali metal pyrophosphates such as sodium pyrophosphate and potassium pyrophosphate, and aqueous solutions of organic bases that do not contain metal ions. An aqueous solution of tetramethylammonium hydroxide (TMAH) is preferable in that it does not contain metal ions and does not affect the semiconductor chip.

[0124] These alkaline aqueous solutions can contain surfactants, antifoaming agents, etc. to improve the development effect. The pH of the above alkaline aqueous solution is preferably in the range of 8 to 12, more preferably in the range of 9 to 11. Also, the base concentration of the above alkaline aqueous solution is preferably 0.1% by mass to 10% by mass. The temperature of the above alkaline aqueous solution can be appropriately selected according to the developability of the photosensitive resin composition layer, but is preferably 20°C to 50°C.

[0125] Organic solvents used as developers include, for example, acetone, ethyl acetate, alkoxyethanol having an alkoxy group with 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, cyclopentanone, cyclohexanone.

[0126] The concentration of such organic solvents is preferably 2% by mass to 90% by mass based on the total amount of the developer. Also, the temperature of such organic solvents can be adjusted according to the developability. Furthermore, such organic solvents can be used alone or in combination of two or more. Examples of organic solvent-based developers used alone include 1,1,1-trichloroethane, N-methylpyrrolidone, N,N-dimethylformamide, cyclohexanone, methyl isobutyl ketone, γ-butyrolactone.

[0127] In pattern formation, two or more developing methods can be used in combination as needed. Examples of developing methods include dip method, paddle method, spray method, high-pressure spray method, brushing, slapping, etc. The high-pressure spray method is suitable for improving resolution. When the spray method is adopted, the spray pressure is preferably 0.05 MPa to 0.3 MPa.

[0128] <Thermosetting (post-baking) process> After the completion of the above step (III), a thermal curing (post-baking) step is performed as necessary. In the above steps (I) to (III), the curing of the photosensitive resin composition layer may progress, but by the thermal curing step, the curing of the photosensitive resin composition can be further advanced to obtain an insulating layer with excellent mechanical strength. Examples of the post-baking step include a heating step using a clean oven. The atmosphere during thermal curing may be air or an inert gas atmosphere such as nitrogen. The heating conditions may be appropriately selected according to the type and content of the resin component in the photosensitive resin composition, but are preferably in the range of 150°C to 250°C for 20 minutes to 180 minutes, more preferably in the range of 160°C to 230°C for 30 minutes to 120 minutes.

[0129] <Other steps> The method for manufacturing a semiconductor package substrate may further include a drilling step and a desmear step after forming the insulating layer as the cured photosensitive resin composition layer. These steps may be carried out according to various methods known to those skilled in the art used for manufacturing a semiconductor package substrate.

[0130] After forming the insulating layer, if desired, a drilling step is performed on the insulating layer formed on the circuit board to form via holes and through holes. The drilling step can be carried out by known methods such as drill, laser, plasma, etc., and if necessary, these methods can be combined. However, a laser drilling step using a carbon dioxide laser, a YAG laser, etc. is preferred.

[0131] The desmear step is a step of performing desmear treatment. Generally, resin residues (smear) adhere inside the openings formed in the drilling step. Since such smear causes poor electrical connection, a treatment (desmear treatment) for removing the smear is carried out in this step.

[0132] The desmear treatment may be carried out by dry desmear treatment, wet desmear treatment, or a combination thereof.

[0133] Examples of dry desmear treatment include, for example, desmear treatment using plasma. Desmear treatment using plasma can be carried out using a commercially available plasma desmear treatment apparatus. Among commercially available plasma desmear treatment apparatuses, suitable examples for the production of semiconductor package substrates include a microwave plasma apparatus manufactured by Nissin Corporation, an atmospheric pressure plasma etching apparatus manufactured by Sekisui Chemical Co., Ltd., and the like.

[0134] Examples of wet desmear treatment include, for example, desmear treatment using an oxidizing agent solution. When performing desmear treatment using an oxidizing agent solution, it is preferable to perform swelling treatment with a swelling solution, oxidation treatment with an oxidizing agent solution, and neutralization treatment with a neutralizing solution in this order. Examples of the swelling solution include "Swelling Dip Security Gun P" and "Swelling Dip Security SBU" manufactured by Atotech Japan Co., Ltd. The swelling treatment is preferably carried out by immersing the substrate having formed vias and the like in a swelling solution heated to 60°C to 80°C for 5 minutes to 10 minutes. As the oxidizing agent solution, an alkaline permanganic acid aqueous solution is preferable, and examples thereof include a solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The oxidation treatment with the oxidizing agent solution is preferably carried out by immersing the substrate after the swelling treatment in an oxidizing agent solution heated to 60°C to 80°C for 10 minutes to 30 minutes. Commercially available products of the alkaline permanganic acid aqueous solution include, for example, "Concentrate Compact CP" and "Dosing Solution Security Gun P" manufactured by Atotech Japan Co., Ltd. The neutralization treatment with the neutralizing solution is preferably carried out by immersing the substrate after the oxidation treatment in a neutralizing solution at 30°C to 50°C for 3 minutes to 10 minutes. As the neutralizing solution, an acidic aqueous solution is preferable, and commercially available products include, for example, "Reduction Solution Security Ant P" manufactured by Atotech Japan Co., Ltd.

[0135] When performing a combination of dry desmear treatment and wet desmear treatment, the dry desmear treatment may be carried out first, or the wet desmear treatment may be carried out first.

[0136] Regardless of whether the insulating layer is formed as any of the rewiring formation layer, the interlayer insulating layer, and the solder resist, after the thermosetting process, a drilling process and a desmear process may be performed. Further, in the method for manufacturing a semiconductor package substrate, a plating process may be further performed.

[0137] The plating process is a process of forming a conductor layer on the insulating layer. The conductor layer may be formed by sputtering after forming the insulating layer, may be formed by combining electroless plating and electroplating, or may form a plating resist having a pattern opposite to that of the conductor layer and form the conductor layer only by electroless plating. As a method for pattern formation thereafter, for example, a subtractive method, a semi-additive method, or the like known to those skilled in the art can be used.

[0138] The semiconductor package substrate according to the second embodiment of the present invention can be manufactured using the above-described photosensitive resin composition, and the cured product of the photosensitive resin composition is used as a rewiring formation layer. Specifically, the method for manufacturing a semiconductor package substrate is (A) a step of laminating a temporary fixing film on a base material, (B) a step of temporarily fixing a semiconductor chip on the temporary fixing film, (C) a step of forming a sealing layer on the semiconductor chip, (D) a step of peeling the base material and the temporary fixing film from the semiconductor chip, (E) a step of forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled, (F) a step of forming a rewiring layer as a conductor layer on the rewiring formation layer, and (G) a step of forming a solder resist layer on the rewiring layer, is included. Further, the method for manufacturing the semiconductor chip package is (H) a step of dicing and singulating a plurality of semiconductor chip packages into individual semiconductor chip packages, may be included.

[0139] <Step (A)> Step (A) is a step of laminating a temporary fixing film on a base material. The lamination conditions between the base material and the temporary fixing film are not particularly limited. For example, the crimping temperature (lamination temperature) is preferably 70°C to 140°C, the crimping pressure is preferably 1 kgf / cm 2 ~11 kgf / cm 2 , the crimping time is preferably 5 seconds to 300 seconds, and it is preferable to laminate under reduced pressure with an air pressure of 20 mmHg or less. Also, the lamination process may be a batch type or a continuous type using rolls. The vacuum lamination method can be carried out using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include the Vacuum Applicator manufactured by Nichco Materials Co., Ltd., the Vacuum Press Laminator manufactured by Meiki Seisakusho Co., Ltd., the Roll Type Dry Coater manufactured by Hitachi Industries Co., Ltd., the Vacuum Laminator manufactured by Hitachi AIC Inc., etc.

[0140] Examples of the base material include silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, cold-rolled steel sheets (SPCC); substrates in which glass fibers are impregnated with an epoxy resin or the like and heat-cured, such as FR-4 substrates; substrates made of bismaleimide triazine resins such as BT resins; and the like.

[0141] The temporary fixing film can be peeled from the semiconductor chip and any material that can temporarily fix the semiconductor chip can be used. Examples of commercially available products include "Revival Alpha" manufactured by Nitto Denko Corporation.

[0142] <Step (B)> Step (B) is a step of temporarily fixing a semiconductor chip on the temporary fixing film. The temporary fixing of the semiconductor chip can be carried out using a device such as a flip chip bonder or a die bonder. The layout and the number of arrangements of the semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc. For example, the semiconductor chips may be aligned and temporarily fixed in a matrix pattern of multiple rows and multiple columns.

[0143] <Step (C)> Step (C) is a step of forming a sealing layer on a semiconductor chip. Any insulating material can be used for the sealing layer, and the photosensitive resin composition described above may also be used. The sealing layer is usually formed by a method including a step of forming a resin composition layer for sealing on the semiconductor chip and a step of thermally curing this resin composition layer to form the sealing layer.

[0144] The formation of the resin composition layer for sealing is preferably carried out by a compression molding method. In the compression molding method, usually, the semiconductor chip and the resin composition for sealing are placed in a mold, and pressure and, if necessary, heat are applied to the resin composition for sealing in the mold to form a resin composition layer for sealing covering the semiconductor chip.

[0145] The specific operation of the compression molding method can be, for example, as follows. As a mold for compression molding, an upper mold and a lower mold are prepared. Also, a resin composition for sealing is applied to the semiconductor chip temporarily fixed on the temporary fixing film as described above. The semiconductor chip coated with the resin composition for sealing is attached to the lower mold together with the base material and the temporary fixing film. Then, the upper mold and the lower mold are clamped, and heat and pressure are applied to the resin composition for sealing to perform compression molding.

[0146] Also, the specific operation of the compression molding method may be, for example, as follows. As a mold for compression molding, an upper mold and a lower mold are prepared. The resin composition for sealing is placed on the lower mold. Also, the semiconductor chip is attached to the upper mold together with the base material and the temporary fixing film. Then, the upper mold and the lower mold are clamped so that the resin composition for sealing placed on the lower mold contacts the semiconductor chip attached to the upper mold, and heat and pressure are applied to perform compression molding.

[0147] The molding conditions vary depending on the composition of the resin composition for sealing, and appropriate conditions can be adopted to achieve good sealing. For example, the temperature of the mold during molding is preferably a temperature at which the resin composition for sealing can exhibit excellent compression moldability, preferably 80°C or higher, more preferably 100°C or higher, particularly preferably 120°C or higher, and preferably 200°C or lower, more preferably 170°C or lower, particularly preferably 150°C or lower. Also, the pressure applied during molding is preferably 1 MPa or higher, more preferably 3 MPa or higher, particularly preferably 5 MPa or higher, and preferably 50 MPa or lower, more preferably 30 MPa or lower, particularly preferably 20 MPa or lower. The cure time is preferably 1 minute or longer, more preferably 2 minutes or longer, particularly preferably 5 minutes or longer, and preferably 60 minutes or shorter, more preferably 30 minutes or shorter, particularly preferably 20 minutes or shorter. Usually, after the formation of the resin composition layer for sealing, the mold is removed. The removal of the mold may be performed before or after the thermosetting of the resin composition layer for sealing.

[0148] The compression molding method may be performed by discharging the resin composition for sealing filled in the cartridge onto the lower mold.

[0149] <Step (D)> Step (D) is a step of peeling the substrate and the temporary fixing film from the semiconductor chip. It is desirable to adopt an appropriate method according to the material of the temporary fixing film. Examples of the peeling method include a method of peeling by heating, foaming, or expanding the temporary fixing film. Also, examples of the peeling method include a method of irradiating ultraviolet rays through the substrate onto the temporary fixing film to reduce the adhesive force of the temporary fixing film and then peeling it.

[0150] In the method of peeling by heating, foaming, or expanding the temporary fixing film, the heating conditions are usually 100°C to 250°C for 1 second to 90 seconds or 5 minutes to 15 minutes. Also, in the method of irradiating ultraviolet rays to reduce the adhesive force of the temporary fixing film and then peeling it, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000 mJ / cm 2 is.

[0151] <Engineering (E)> Engineering (E) is a process of forming a redistribution layer as an insulating layer on the surface from which the base material of the semiconductor chip and the temporary fixing film have been peeled off. The redistribution layer uses the photosensitive resin composition of the present invention. The method of forming the redistribution layer is the same as the method of forming the photosensitive resin composition layer in process (I) of the first embodiment.

[0152] When forming the redistribution layer, in order to layer-connect the semiconductor chip and the redistribution layer, via holes may be formed in the redistribution layer.

[0153] Via holes can usually be formed by performing an exposure process of irradiating actinic light through a mask pattern on the surface of the photosensitive resin composition layer for forming the redistribution layer, and a development process of developing and removing the unexposed portions where the actinic light has not been irradiated. The irradiation amount and irradiation time of the actinic light can be appropriately set according to the photosensitive resin composition layer. Examples of the exposure method include a contact exposure method of bringing the mask pattern into close contact with the photosensitive resin composition layer for exposure, and a non-contact exposure method of using parallel light rays for exposure without bringing the mask pattern into close contact with the photosensitive resin composition layer. The actinic light, the alkaline aqueous solution, and the exposure and development method are as described above.

[0154] The shape of the via hole is not particularly limited, but is generally circular (substantially circular). The top diameter of the via hole is preferably 50 μm or less, more preferably 30 μm or less, still more preferably 20 μm or less, and preferably 0.1 μm or more, preferably 0.5 μm or more, more preferably 1.0 μm or more. Here, the top diameter of the via hole refers to the diameter of the opening of the via hole on the surface of the redistribution layer.

[0155] <Process (F)> Step (F) is a step of forming a rewiring layer as a conductor layer on a rewiring formation layer. The method of forming a rewiring layer on a rewiring formation layer may be the same as the method of forming a conductor layer on an insulating layer in the first embodiment. Further, steps (E) and (F) may be repeated to alternately stack (build up) the rewiring layer and the rewiring formation layer.

[0156] <Step (G)> Step (G) is a step of forming a solder resist layer on the rewiring layer. As the material of the solder resist layer, any insulating material can be used. Among them, a photosensitive resin and a thermosetting resin are preferable from the viewpoint of ease of manufacturing a semiconductor chip package. Further, the photosensitive resin composition of the present invention may be used.

[0157] Further, in step (G), bumping processing for forming bumps may be performed as necessary. The bumping processing can be performed by methods such as solder balls and solder plating. Further, the formation of via holes in the bumping processing can be performed in the same manner as in step (E).

[0158] The method for manufacturing a semiconductor chip package may include step (H) in addition to steps (A) to (G). Step (H) is a step of dicing a plurality of semiconductor chip packages into individual semiconductor chip packages and separating them. The method for dicing a semiconductor chip package into individual semiconductor chip packages is not particularly limited.

[0159] [Semiconductor Device] Examples of the semiconductor device in which the above-described semiconductor chip package is mounted include various semiconductor devices used in electrical products (for example, computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical devices, and televisions, etc.) and vehicles (for example, motorcycles, automobiles, trains, ships, and airplanes, etc.).

Examples

[0160] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the following description, unless otherwise specified, "parts" and "%" mean "parts by mass" and "mass %", respectively.

[0161] <Synthesis Example 1: Synthesis of Polyimide Precursor A> 52.0 g of 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (BPADA) was placed in a 2 L separable flask, 500 mL of N-methyl-2-pyrrolidone was added, and the mixture was stirred at room temperature. Further, 45.0 g of 5-(4-aminophenoxy)-3-[4-(4-aminophenoxy)phenyl]-1,1,3-trimethylindane (INDAN) was added, and at the same time, the reaction vessel was heated in an oil bath until the internal temperature reached 40 °C, and polymerization was carried out for 20 hours.

[0162] Next, 2.01 g of potassium hydride was added to the reaction solution and stirred at room temperature, 4.40 g of ethylene carbonate was added, and at the same time, the reaction vessel was heated in an oil bath until the internal temperature reached 80 °C, and stirring was carried out for 10 hours. The obtained reaction solution was cooled to 40 °C, 4.53 g of acryloyl chloride, 0.6 g of 4-dimethylaminopyridine, and 10.1 g of triethylamine were added, and stirring was carried out for 3 hours.

[0163] Next, the obtained reaction solution was dropped into 6 L of ultrapure water to precipitate the polymer. After filtering off the precipitated polymer, it was dried under heating at 80 °C in vacuum to obtain 71 g of polyimide precursor A. The structure of the polyimide precursor is shown in the following formula (wherein n is an integer of 5 to 200, and the ratio of the structural unit in which R represents a hydrogen atom to the structural unit in which R represents other than hydrogen is 1 about 75:25 from 1H NMR.). When the molecular weight of polyimide precursor A was measured by gel permeation chromatography (in terms of standard polystyrene), the weight average molecular weight (Mw) was 50,000. [Chemical formula]

[0164] <Preparation of Photosensitive Resin Composition> According to the description in the following table, 100 parts by mass of the polyimide precursor A1 prepared in Synthesis Example 1 as component (A), component (B), component (C), component (D) and component (E) were dissolved in 280 parts by mass of γ-butyrolactone (GBL) to prepare each photosensitive resin composition described in the following table.

[0165]

Table 1

[0166] The abbreviations etc. in the table are as follows. A-1: Polyimide Precursor A Prepared in Synthesis Example B-1: Compound Represented by the Following Formula (Manufactured by Shin-Nakamura Chemical Co., Ltd., NOD-N)

Chemical Formula

[0167] B-2: Compound Represented by the Following Formula (Manufactured by Shin-Nakamura Chemical Co., Ltd., DOD-N)

Chemical Formula

[0168] B-3: Compound Represented by the Following Formula (Manufactured by Shin-Nakamura Chemical Co., Ltd., DDD)

Chemical Formula

[0169] B-4: Compound Represented by the Following Formula (Manufactured by Shin-Nakamura Chemical Co., Ltd., HOD-N)

Chemical Formula

[0170] B-5: Compound Represented by the Following Formula (Manufactured by Shin-Nakamura Chemical Co., Ltd., 14G)

Chemical Formula

[0171] C-1: Compound represented by the following formula (manufactured by Shin-Nakamura Chemical Co., Ltd., D-TMP)

Chemical formula

[0172] D-1: Compound represented by the following formula (manufactured by BASF, Irgacure OXE01)

Chemical formula

[0173] D-2:: Compound represented by the following formula (manufactured by BASF, Irgacure OXE02)

Chemical formula

[0174] E-1: Compound represented by the following formula

Chemical formula

[0175] <Evaluation of residual film property (film thickness reduction during development)> Copper plating was laminated on a silicon wafer with a film thickness of 5 μm, and the photosensitive resin compositions formulated in the examples and comparative examples were applied onto a substrate that had been roughened with a 1% hydrochloric acid aqueous solution for 10 seconds at a rotational speed suitable for a film thickness of 15 μm using a spin coater, and then heated on a hot plate at 120 °C for 2 minutes to prepare a photosensitive resin composition layer. This is referred to as a laminate.

[0176] The prepared laminate was exposed to ultraviolet light (wavelength 365 nm, intensity 40 mW / cm 2 ). The exposure dose was set to the optimum value in the range from 50 mJ / cm 2 to 1000 mJ / cm 2 . A quartz glass mask for drawing a round hole (via) with an opening diameter of 20 μm was used as the exposure pattern.

[0177] Next, on the entire surface of the photosensitive resin composition layer of the laminate, spray development was performed with cyclopentanone as a developer at a spray pressure of 0.1 MPa for an optimal time between 20 seconds and 90 seconds, and then spray rinsing was performed with propylene glycol monomethyl ether acetate at a spray pressure of 0.1 MPa for 30 seconds. Further, heat treatment was performed at 170 °C for 180 minutes to cure the photosensitive resin composition layer. The diameter of the bottom of the via was observed (magnification 1000 times) by SEM and measured, and the formation of vias with an opening diameter of 20 μm was confirmed.

[0178] The film thickness after development was measured, and the remaining film property was calculated as the film thickness residual ratio by the following calculation method and evaluated according to the following criteria. Film thickness residual ratio = Film thickness after development / Film thickness after coating (before exposure) × 100 (%) 〇: Film thickness residual ratio is 60% or more ×: Film thickness residual ratio is less than 60%

[0179] <Evaluation of dielectric constant and dielectric loss tangent> The photosensitive resin compositions prepared in the examples and comparative examples were coated on a peeled PET film (product name NS-80A: manufactured by Fujimori Kogyo Co., Ltd.) using a blade so that the film thickness became 140 μm. The solution on this PET film was heated at 80 °C for 10 minutes using a heating machine to obtain a photosensitive resin composition layer. The photosensitive resin composition layer was peeled from the PET film, and the photosensitive resin composition layer was attached to a metal frame using a heat-resistant tape and cured at 170 °C for 3 hours to prepare a photosensitive resin composition film for physical property measurement.

[0180] From the photosensitive resin composition film for physical property measurement, test pieces with a width of 2 mm and a length of 80 mm were cut out. For the cut test pieces, the dielectric loss tangent and dielectric constant were measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23 °C by the cavity resonance perturbation method using a measuring device "HP8362B" manufactured by Agilent Technologies.

[0181]

Table 2

[0182] In Examples 1 to 4, cured products excellent in residual film properties and dielectric properties could be obtained. On the other hand, Comparative Examples 1 to 3 did not satisfy all of the residual film properties and dielectric properties. In addition, in Examples 1 to 4, even when the (E) component was not contained, although there was a difference in degree, it was confirmed that by increasing the exposure amount, the same results as those of the above examples could be achieved.

Claims

1. (A) A polyimide precursor, (B) A compound having two ethylenically unsaturated bonds and a divalent aliphatic hydrocarbon group having 8 or more carbon atoms which may have a substituent, (C) A crosslinking agent having three or more functional groups, and (D) A photo radical generator, which contains, and the photosensitive resin composition in which the component (A) has a structural unit represented by the following formula (A-1). 【Chemical 1】 (In the formula, each A independently represents a tetravalent organic group, each B independently represents a divalent organic group having an indane skeleton, R 1 and R 2 each independently represent a hydrogen atom or a monovalent organic group. n represents an integer of 5 to 200.)

2. The photosensitive resin composition according to claim 1, further containing (E) a sensitizer.

3. The photosensitive resin composition according to claim 1 or 2, wherein the component (B) contains a compound represented by the following formula (B-1). 【Chemical Formula 2】 (wherein, R １ｂ and R ２ｂ each independently represents a hydrogen atom or a methyl group. nb represents an integer of 8 to 20.)

4. R in formula (A-1) １ and R ２ are each independently a photosensitive resin composition according to claim 1, wherein at least one of them is a radical-reactive group.

5. The photosensitive resin composition according to claim 1, wherein the radical reactive group is represented by the following formula (A-2). 【Chemical Formula 3】 (wherein, R ４ ~R ６ each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and p represents an integer of 1 to 10.)

6. The photosensitive resin composition according to claim 1, wherein the component (A) has a structural unit represented by the following formula (A-3). [Chemical Formula 4] (In the formula, each A1 independently represents a tetravalent organic group, and R １１ and R １２ each independently represent a hydrogen atom or a monovalent organic group, R １３ each independently represent a hydrogen atom or a methyl group, each Xa independently represents a single bond, a group represented by the following formula (1), or a group represented by formula (2), and each Xb independently represents a single bond, a group represented by formula (3), or a group represented by formula (4). m1 represents an integer of 1 to 5, and n1 represents an integer of 5 to 200.) 【Chemical Formula 5】 (In formulas (1) to (4), * represents a bond.)

7. A photosensitive film in which a photosensitive resin composition layer composed of the photosensitive resin composition according to any one of claims 1 to 6 is formed on a support.

8. A semiconductor package substrate including an insulating layer formed of a cured product of the photosensitive resin composition according to any one of claims 1 to 6.

9. A semiconductor device including the semiconductor package substrate according to claim 8.

10. A step of forming a photosensitive resin composition layer containing the photosensitive resin composition according to any one of claims 1 to 6 on a circuit board; A step of irradiating the photosensitive resin composition layer with actinic rays; A method for manufacturing a semiconductor package substrate, including a step of developing the photosensitive resin composition layer.

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