KR20230159431A - diester compounds - Google Patents

Abstract

A low-viscosity diester compound that forms a resin composition exhibiting excellent fluidity when combined with a crosslinkable resin is provided. The diester compound is represented by the following formula (X).

⁽ In the formula _{, X core} ^represents a divalent aliphatic group ^, X ¹ _{end and} , an aromatic ring having as a substituent one or more types selected from an unsaturated aliphatic hydrocarbon group, a halogen atom, an alkyl group, and an aryl group.)

Description

diester compounds

The present invention relates to diester compounds. It also relates to a resin crosslinking agent, resin composition, resin sheet, prepreg, cured product, semiconductor chip package, printed wiring board, and semiconductor device obtained by using the diester compound.

A resin composition containing a crosslinkable resin such as an epoxy resin and its crosslinking agent (curing agent) forms a cured product with excellent insulation, heat resistance, adhesion, etc., and has been widely used as a material for electronic components such as semiconductor packages and printed wiring boards.

Meanwhile, in high-speed communications such as the 5th generation mobile communication system (5G), transmission loss when operating in a high-frequency environment is a problem. Therefore, an insulating material with excellent dielectric properties (low dielectric constant, low dielectric loss tangent) is needed. In addition, as electronic devices become more compact, highly integrated, and multi-functional, bump diameters are becoming smaller, pitches are becoming narrower, and gaps are becoming narrower by increasing the number of fins. As a result, the flow path of the sealing material during seal molding became more complex, the semiconductor sealing material required even better fluidity, and the crosslinking agent used was also required to have a lower viscosity.

As a resin material with excellent dielectric properties, for example, Patent Document 1 discloses an active ester resin that is a reaction product of aromatic diacid chlorides and aromatic hydroxy compounds as a crosslinking agent for epoxy resins.

[Patent Document 1] International Publication No. 2018/235424

The active ester resin described in Patent Document 1 has excellent dielectric properties compared to conventional phenol-based crosslinking agents, etc., but there is room for improvement in lowering the viscosity, and the fluidity of the resin composition containing the active ester resin and the crosslinkable resin is satisfactory. It is not at a level that can be achieved.

In addition, from the viewpoint of obtaining a cured product with a low dielectric loss tangent, from the viewpoint of improving heat resistance and moisture resistance after seal molding, from the viewpoint of realizing low warpage when seal molding a large area such as wafer level package (WLP), power semiconductors, etc. In some cases, a resin composition with a high content of inorganic filler is used from the viewpoint of achieving good heat dissipation in a high-heat device, but in such cases, fluidity at the molding temperature deteriorates, and flow marks and unfilled areas occur. Problems like this are likely to occur.

The object of the present invention is to provide a low-viscosity diester compound that forms a resin composition exhibiting excellent fluidity when combined with a crosslinkable resin.

Conventionally, when using an ester compound as a crosslinking agent for a crosslinkable resin, in order to exhibit crosslinking characteristics, the ester compound has an aromatic carbon-ester bond-aromatic carbon structure as described in Patent Document 1 as an ester bond portion. It has been thought to be limited to having . However, as a result of careful study by the present inventors, even in the structure of aliphatic carbon-ester bond-aromatic carbon, the ester bond portion having the structure of aliphatic carbon -C(=O)-O-aromatic carbon exhibits crosslinking characteristics. I found that And in the process of examining diester compounds having the structure of this aliphatic carbon -C(=O)-O- aromatic carbon, it was discovered that the above problem could be solved by a diester compound having the following structure, The present invention has been completed.

That is, the present invention includes the following contents.

[1] A diester compound represented by the following formula (X).

(During the ceremony,

X _core represents a divalent aliphatic group,

_X ¹ _{end and} X ² _end each independently represent an aromatic ring which may have a substituent, and at least one of X ^{1 end} and It is an aromatic ring having one or more types selected from as a substituent.)

[2] The diester compound according to [1], in which the number of carbon atoms of the divalent aliphatic group in the X _core is 6 or more.

[3] The diester compound according to [1] or [2], wherein in the X _core , the divalent aliphatic group is an alkylene group.

[4] The diester compound according to any one of [1] to [3], wherein both X ¹ _end and X ² _end are aromatic rings having an unsaturated aliphatic hydrocarbon group as a substituent.

[5] The diester compound according to any one of [1] to [4], wherein the unsaturated aliphatic hydrocarbon group at X ¹ _end and X ² _end is an allyl group.

[6] The diester compound according to any one of [1] to [5], wherein the aromatic ring in X ¹ _end and X ² _end is an aromatic carbocycle having 6 to 14 carbon atoms.

[7] The diester compound according to any one of [1] to [6], which is liquid at 25°C.

[8] The diester compound according to any one of [1] to [7], wherein the diester compound has a viscosity of 300 mPa·s or less at 25°C.

[9] A resin crosslinking agent containing a diester compound represented by the following formula (X).

(During the ceremony,

X _core represents a divalent aliphatic group,

X ¹ _end and X ² _end each independently represent an aromatic ring that may have a substituent.)

[10] The resin crosslinking agent according to [9], wherein the diester compound is the diester compound according to any one of [1] to [8].

[11] A resin composition comprising a diester compound (X) and a crosslinkable resin (Y),

A resin composition in which the diester compound (X) is represented by the following formula (X).

(During the ceremony,

X _core represents a divalent aliphatic group,

X ¹ _end and X ² _end each independently represent an aromatic ring that may have a substituent.)

[12] The resin composition according to [11], wherein the diester compound (X) is the diester compound according to any one of [1] to [8].

[13] The resin composition according to [11] or [12], wherein the crosslinkable resin (Y) is at least one selected from the group consisting of thermosetting resins and radically polymerizable resins.

[14] The resin composition according to any one of [11] to [13], further comprising an inorganic filler.

[15] The resin composition according to any one of [11] to [14], further comprising an organic solvent.

[16] The resin composition according to any one of [11] to [15], which is for sealing semiconductors.

[17] The resin composition according to any one of [11] to [15], which is for an insulating layer of a printed wiring board.

[18] A resin sheet comprising a support and a layer of the resin composition according to any one of [11] to [17] provided on the support.

[19] A prepreg produced by impregnating a sheet-like fiber base material with the resin composition according to any one of [11] to [17].

[20] A cured product of the resin composition according to any one of [11] to [17].

[21] A semiconductor chip package including a sealing layer made of a cured product of the resin composition according to any one of [11] to [16].

[22] The semiconductor chip package described in [21], which is a fan-out type package.

[23] A printed wiring board comprising an insulating layer made of a cured product of the resin composition according to any one of [11] to [15] and [17].

[24] A semiconductor device comprising the semiconductor chip package according to [21] or [22] or the printed wiring board according to [23].

According to the present invention, it is possible to provide a low-viscosity diester compound that forms a resin composition exhibiting excellent fluidity when combined with a crosslinkable resin.

According to the diester compound of the present invention, even when the content of inorganic filler is high, a resin composition showing good fluidity at the molding temperature can be formed.

[FIG. 1A] FIG. 1A shows a GPC chart of the diester compound (A) in Example 1.
[FIG. 1B] FIG. 1B shows an IR chart of the diester compound (A) in Example 1.
[FIG. 2A] FIG. 2A shows a GPC chart of the diester compound (B) in Example 2.
[FIG. 2B] FIG. 2B shows an IR chart of the diester compound (B) in Example 2.
[FIG. 3A] FIG. 3A shows a GPC chart of the diester compound (C) in Example 3.
[FIG. 3B] FIG. 3B shows the IR chart of the diester compound (C) in Example 3.
[FIG. 4A] FIG. 4A shows the GPC chart of the diester compound (D) in Example 4.
[FIG. 4B] FIG. 4B shows the IR chart of the diester compound (D) in Example 4.
[FIG. 5A] FIG. 5A shows a GPC chart of the diester compound (E) in Example 5.
[FIG. 5B] FIG. 5B shows an IR chart of the diester compound (E) in Example 5.
[FIG. 6A] FIG. 6A shows a GPC chart of the diester compound (F) in Comparative Example 1.
[FIG. 6B] FIG. 6B shows an IR chart of the diester compound (F) in Comparative Example 1.

<Explanation of terms>

In this specification, the term “may have a substituent” referring to a compound or group refers to the case where the hydrogen atom of the compound or group is not substituted with a substituent, and some or all of the hydrogen atoms of the compound or group are It means both sides when substituted with a substituent.

In this specification, unless otherwise specified, the term “substituent” refers to a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkapolyenyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cycloalkyloxy group, and an aryl group. group, aryloxy group, arylalkyl group, arylalkoxy group, monovalent heterocyclic group, alkylidene group, amino group, silyl group, acyl group, acyloxy group, carboxyl group, sulfo group, cyano group, nitro group, hydroxy group, mercap It refers to earthenware and oxoware. On the other hand, aliphatic hydrocarbon groups having unsaturated bonds such as alkenyl group, alkynyl group, alkapolyenyl group, and cycloalkenyl group are collectively referred to as “unsaturated aliphatic hydrocarbon group.”

Examples of halogen atoms used as substituents include fluorine atom, chlorine atom, bromine atom, and iodine atom.

The alkyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 14, further preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl. , and decyl groups.

The alkenyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkenyl group is preferably 2 to 20, more preferably 2 to 14, even more preferably 2 to 12, even more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkenyl group include vinyl, allyl, 1-propenyl, butenyl, sec-butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, Nonenyl group, and decenyl group are mentioned.

The alkynyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkynyl group is preferably 2 to 20, more preferably 2 to 14, even more preferably 2 to 12, even more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkynyl group include ethynyl group, propynyl group, butynyl group, sec-butynyl group, isobutynyl group, tert-butynyl group, pentynyl group, hexynyl group, heptynyl group, octynyl group, noninyl group, and decynyl group. You can raise your flag.

The alkapolyenyl group used as a substituent may be either linear or branched, and the number of double bonds is preferably 2 to 10, more preferably 2 to 6, further preferably 2 to 4, and more preferably 2 to 4. More preferably, it is 2. The number of carbon atoms of the alkapolyenyl group is preferably 3 to 20, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 6.

The number of carbon atoms of the cycloalkyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6. Examples of the cycloalkyl group include cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.

The number of carbon atoms of the cycloalkenyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6. Examples of the cycloalkenyl group include cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, and cyclohexenyl group.

The alkoxy group used as a substituent may be either linear or branched. The number of carbon atoms of the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and still more preferably 1 to 6. Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, and hepyloxy group. Examples include tyloxy group, octyloxy group, nonyloxy group, and decyloxy group.

The number of carbon atoms of the cycloalkyloxy group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6. Examples of the cyclooxy group include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, and cyclohexyloxy group.

The aryl group used as a substituent is a group obtained by removing one hydrogen atom on the aromatic ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of the aryl group include phenyl group, naphthyl group, and anthracenyl group.

The number of carbon atoms of the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and even more preferably 6 to 10. Examples of aryloxy groups used as substituents include phenoxy group, 1-naphthyloxy group, and 2-naphthyloxy group.

The number of carbon atoms of the arylalkyl group used as a substituent is preferably 7 to 25, more preferably 7 to 19, further preferably 7 to 15, and even more preferably 7 to 11. As the arylalkyl group, for example, phenyl-C ₁ to C ₁₂ alkyl group, naphthyl-C ₁ to C ₁₂ alkyl group, and anthracenyl-C ₁ to A C ₁₂ alkyl group may be mentioned.

The number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7 to 25, more preferably 7 to 19, further preferably 7 to 15, and even more preferably 7 to 11. As the arylalkoxy group, for example, phenyl-C ₁ to C ₁₂ alkoxy group, and naphthyl-C ₁ to A C ₁₂ alkoxy group may be mentioned.

A monovalent heterocyclic group used as a substituent refers to a group in which one hydrogen atom has been removed from the heterocyclic ring of a heterocyclic compound. The number of carbon atoms of the monovalent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and still more preferably 3 to 9. The monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl group). Examples of the monovalent heterocycle include thienyl group, pyrrolyl group, furanyl group, furyl group, pyridyl group, pyridazinyl group, pyrimidyl group, pyrazinyl group, triazinyl group, pyrrolidyl group, and piperidyl group. , quinolyl group, and isoquinolyl group.

An alkylidene group used as a substituent refers to a group obtained by removing two hydrogen atoms from the same carbon atom of an alkane. The number of carbon atoms of the alkylidene group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 12, even more preferably 1 to 6, especially preferably 1 to 3. . Examples of the alkylidene group include methylidene group, ethylidene group, propylidene group, isopropylidene group, butylidene group, sec-butylidene group, isobutylidene group, tert-butylidene group, and pentylidene group. , hexylidene group, heptylidene group, octylidene group, nonylidene group, and decylidene group.

The acyl group used as a substituent refers to a group represented by the formula: -C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be either linear or branched. Examples of the aryl group represented by R include phenyl group, naphthyl group, and anthracenyl group. The number of carbon atoms of the acyl group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. Examples of the acyl group include acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, and benzoyl group.

The acyloxy group used as a substituent refers to a group represented by the formula: -O-C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be either linear or branched. Examples of the aryl group represented by R include phenyl group, naphthyl group, and anthracenyl group. The number of carbon atoms of the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. Examples of the acyloxy group include acetoxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, pivaloyloxy group, and benzoyloxy group.

The above-mentioned substituent may further have a substituent (hereinafter sometimes referred to as a “secondary substituent”). As the secondary substituent, unless otherwise specified, the same substituent as the above-mentioned substituent may be used.

In this specification, the term “aliphatic group” refers to a group in which one or more hydrogen atoms bonded to the aliphatic carbon of an aliphatic compound have been removed. In detail, a monovalent aliphatic group refers to a group in which one hydrogen atom bonded to the aliphatic carbon of an aliphatic compound has been removed, and a divalent aliphatic group refers to a group in which two hydrogen atoms bonded to the aliphatic carbon of an aliphatic compound have been removed. Examples of the divalent aliphatic group include an alkylene group which may have a substituent, a cycloalkylene group which may have a substituent, an alkenylene group which may have a substituent, and a cycloalkenylene group which may have a substituent. In this specification, unless otherwise specified, the number of carbon atoms of the aliphatic group is preferably 1 or more, more preferably 2 or more, further preferably 3 or more, 4 or more, 5 or more, or 6 or more. Preferably it is 50 or less, more preferably 40 or less, and even more preferably 30 or less, 20 or less, 18 or less, 16 or less, 14 or less, or 12 or less. The number of carbon atoms of the substituent is not included in the number of carbon atoms.

In this specification, the term “aromatic ring” refers to a ring according to Hückel's rule in which the number of electrons contained in the cyclic π electron system is 4p + 2 (p is a natural number), a monocyclic aromatic ring, and two or more monocyclic rings. Condensed aromatic rings are included in which cyclic aromatic rings are condensed. The aromatic ring may be an aromatic carbocyclic ring having only carbon atoms as ring constituent atoms, or an aromatic heterocycle having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms as ring constituent atoms. In this specification, unless otherwise specified, the number of carbon atoms in the aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, and still more preferably 6 or more, and the upper limit is preferably 24. or less, more preferably 18 or less or 14 or less, and even more preferably 10 or less. The number of carbon atoms of the substituent is not included in the number of carbon atoms. Examples of aromatic rings include benzene ring, furan ring, thiophene ring, pyrrole ring, pyrazole ring, oxazole ring, isoxazole ring, thiazole ring, imidazole ring, pyridine ring, pyridazine ring, pyrimidine ring, and pyridine ring. Monocyclic aromatic rings such as jin rings; Naphthalene ring, anthracene ring, phenanthrene ring, benzofuran ring, isobenzofuran ring, indole ring, isoindole ring, benzothiophene ring, benzoimidazole ring, indazole ring, benzoxazole ring, benzoisoxazole ring, benzothia Condensed aromatic rings are a condensation of two or more monocyclic aromatic rings, such as a sol ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, an acridine ring, a quinazoline ring, a cinnoline ring, and a phthalazine ring.

Hereinafter, the present invention will be described in detail based on its preferred embodiments. However, the present invention is not limited to the following embodiments and examples, and may be implemented with any modification without departing from the scope of the claims and equivalents thereof.

[Diester compound]

The diester compound of the present invention is,

A core unit consisting of a divalent aliphatic group,

It contains first and second blocking units bonded to the core unit through an ester bond, and the first and second blocking units are each independently an aromatic ring that may have a substituent.

In the diester compound of the present invention, the core unit and the blocking unit are bonded through an ester bond (-C(=O)-O-). In detail, the core unit and the blocking unit are bonded through an ester bond so that the carbonyl group (-C(=O)-) is bonded to the core unit and the oxy group (-O-) is bonded to the blocking unit. Accordingly, the diester compound of the present invention has a structure of aliphatic carbon -C(=O)-O- aromatic carbon as the ester bond portion. As described later, the present invention is based on the discovery that an ester bond portion having the structure of such an aliphatic carbon -C(=O)-O- aromatic carbon exhibits crosslinking characteristics, and it was predicted from the prior art knowledge that It starts with knowledge you didn’t even have before.

Therefore, assuming that the core unit is X _core and the first and second blocking units are X ¹ _end and X ² _end , respectively, the diester compound of the present invention can be represented by the following formula (X).

(During the ceremony,

X _core represents a divalent aliphatic group,

X ¹ _end and X ² _end each independently represent an aromatic ring that may have a substituent.)

-Core unit (X _core )-

Core unit X _core consists of a divalent aliphatic group.

By having a core unit composed of a divalent aliphatic group, the diester compound of the present invention can exhibit low viscosity characteristics. Additionally, when combined with a crosslinkable resin, a cured product with high toughness and flexibility can be obtained.

When using an ester compound as a crosslinking agent for a crosslinkable resin, in order to express crosslinking properties and form an active ester bond, the ester bond portion must have the structure of an aromatic carbon -C(=O)-O- aromatic carbon. It has been considered In contrast, the diester compound of the present invention containing a core unit composed of a divalent aliphatic group has a structure of aliphatic carbon -C(=O)-O- aromatic carbon. The present inventors have discovered that a diester compound having such a specific ester bond structure exhibits good low viscosity characteristics and functions as a crosslinking agent for a crosslinkable resin.

In the _core unit Accordingly, in one preferred embodiment, in the core unit X _core , the number of carbon atoms of the divalent aliphatic group is 6 or more. The upper limit of the number of carbon atoms of the divalent aliphatic group is not particularly limited, and may be appropriately determined within the above-mentioned range. On the other hand, the number of carbon atoms of the substituent is not included in the number of carbon atoms.

In the _core unit An alkylene group, which may have , is particularly suitable. The alkylene group in the core unit may be either linear or branched. Accordingly, in one preferred embodiment, in the core unit X _core , the divalent aliphatic group is an alkylene group.

The substituents that the alkylene group or alkenylene group in the core unit may have are as described above. Among these, the substituent is preferably at least one selected from a halogen atom, an alkyl group, and an alkenyl group, and more preferably at least one selected from a fluorine atom and an alkyl group having 1 to 6 carbon atoms.

-First and second blockade units (X ¹ _end and X ² _end )-

The first and second blocking units X ¹ _end and X ² _end are each independently an aromatic ring that may have a substituent.

By having an aromatic ring that may have a substituent as the first and second blocking units, the diester compound of the present invention can be used by blending into a resin composition as a crosslinking agent for a crosslinkable resin.

^In the blocking units X ¹ _{end and} The number of carbon atoms in the aromatic carbocyclic ring is preferably 6 to 14, more preferably 6 to 10. Accordingly, in one suitable embodiment, in the cloaking unit, the aromatic ring is an aromatic carbocycle having 6 to 14 carbon atoms.

The substituents that the aromatic ring in the blocking unit may have are as described above. Among them, from the viewpoint of realizing a diester compound with a lower viscosity, at least one type selected from an unsaturated aliphatic hydrocarbon group, a halogen atom, an alkyl group, and an aryl group is preferable, and an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms is preferable. , a fluorine atom, an alkyl group with 1 to 6 carbon atoms, and an aryl group with 6 to 10 carbon atoms, is more preferable. When the aromatic ring in the blocking unit has a substituent, only one of the first and second blocking units X ¹ _end and X ² _end may have a substituent, or both of them may have a substituent. ^In _one embodiment _{, at} least one of the ^first and ^second blocking units At least _one ^of the In the case of an aromatic ring ⁱⁿ which the X ¹ _end and _the On the other hand, in the case of aromatic rings in which X ¹ _end and X ² _end have substituents, crystallinity is weak, it is easy to liquefy at room temperature, and fluidity and workability are excellent.

Among them, when at least _{one of} the ^first and ^second blocking units Therefore, in one preferred embodiment, at least one of the first and second blocking units X ¹ _end and X ² _end is an aromatic ring having an unsaturated aliphatic hydrocarbon group as a substituent. When both the first and second blocking units are aromatic rings having an unsaturated aliphatic hydrocarbon group as a substituent, a diester compound having a particularly low viscosity, for example, a liquid state at room temperature (25°C) can be realized. Here, in this specification, “liquid state at room temperature (25°C)” regarding a diester compound means that the viscosity of the diester compound at 25°C is 3,000 mPa·s or less. Therefore, in one preferred embodiment, both the first and second blocking units X ¹ _end and X ² _end are aromatic rings having an unsaturated aliphatic hydrocarbon group as a substituent.

From the viewpoint of realizing a diester compound with even lower viscosity, the number of carbon atoms of the unsaturated aliphatic hydrocarbon group that the aromatic ring in the blocking unit may have as a substituent is preferably 2 to 20, more preferably 2 to 14, 2 to 12, 2 to 10 or 2 to 6. From the viewpoint of realizing a diester compound with even lower viscosity, the unsaturated aliphatic hydrocarbon group is preferably an alkenyl group or an alkynyl group, and more preferably an alkenyl group. Among them, the unsaturated aliphatic hydrocarbon group that the aromatic ring in the blocking unit may have as a substituent is preferably an alkenyl group with 2 to 10 carbon atoms, more preferably an alkenyl group with 2 to 6 carbon atoms, and even more preferably an allyl group. do. Therefore, in one preferred embodiment, in the blocking units X ¹ _end and X ² _end , the unsaturated aliphatic hydrocarbon group that the aromatic ring may have as a substituent is an allyl group.

In one embodiment, the diester compound of the present invention is represented by the following formula (X1).

(During the ceremony,

X _core represents a core unit consisting of a divalent aliphatic group,

Ring Ar each independently represents an aromatic ring,

R ¹ each independently represents an unsaturated aliphatic hydrocarbon group,

R ² each independently represents a substituent,

n11 and n12 each independently represent an integer from 0 to 2,

m11 and m12 represent integers that satisfy 0≤m11≤(p-n11) and 0≤m12≤(p-n12), assuming that the number of hydrogen atoms that can be substituted for ring Ar is p.)

In formula (X1), X _core represents a core unit consisting of a divalent aliphatic group. Regarding the core unit, suitable examples thereof are included and are as described above. In one preferred _embodiment , Suitable examples of substituents are also as described above.

In formula (X1), each ring Ar independently represents an aromatic ring. The aromatic ring corresponds to the aromatic ring in the first and second blocking units, includes suitable examples thereof, and is as described above. In a suitable embodiment, the rings Ar are each independently an aromatic carbocycle having 6 to 14 carbon atoms, and more preferably a benzene ring or a naphthalene ring.

In formula (X1), R ¹ each independently represents an unsaturated aliphatic hydrocarbon group. R ¹ corresponds to an unsaturated aliphatic hydrocarbon group that the aromatic ring in the first and second blocking units may have as a substituent, includes suitable examples thereof, and is as described above. In one suitable embodiment, R ¹ is each independently an unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms (preferably 2 to 10 or 2 to 6). alkenyl group, or an alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 or 2 to 6 carbon atoms), and more preferably an allyl group.

In formula (X1), R ² each independently represents a substituent. R ² corresponds to a substituent that the aromatic ring in the first and second blocking units may have, includes suitable examples thereof, and is as described above. In one suitable embodiment, R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group, more preferably a fluorine atom, an alkyl group with 1 to 6 carbon atoms, and 6 to 10 carbon atoms. is selected from the aryl group of

In formula (X1), n11 and n12 each independently represent an integer of 0 to 2. As explained for the first and second containment units, it is preferable that at least one of n11 and n12 is 1 or more, especially from the viewpoint of realizing a low-viscosity diester compound. In one preferred embodiment, n11 and n12 are each independently 1 or 2, and more preferably, both n11 and n12 are 1.

When n11 or n12 is 1 or more, the bonding position of R ¹ to ring Ar is not particularly limited, but from the viewpoint of realizing a diester compound with lower viscosity, in the relationship with the bonding position of the oxy group of the ester bond, It is preferable that it is an ortho position or a meta position, and an ortho position is more preferable.

In formula (X1), m11 and m12 are integers that satisfy 0≤m11≤(p-n11) and 0≤m12≤(p-n12), assuming that the number of hydrogen atoms that can be substituted for ring Ar is p. represents. The number p of replaceable hydrogen atoms in ring Ar does not include the bonding site with the oxy group of the ester bond. For example, when ring Ar is a benzene ring, the number p of replaceable hydrogen atoms is 5, and when ring Ar is a naphthalene ring, the number p of replaceable hydrogen atoms is 7.

In one suitable embodiment, the diester compound of the present invention is represented by the following formula (X2) or the following formula (X3).

(During the ceremony,

X _core , R ¹ and R ² are as described above,

n21 and n22 each independently represent an integer from 0 to 2,

m21 and m22 represent integers satisfying 0≤m21≤(5-n21) and 0≤m22≤(5-n22).)

(During the ceremony,

X _core , R ¹ and R ² are as described above,

n31 and n32 each independently represent an integer from 0 to 2,

m31 and m32 represent integers that satisfy 0≤m31≤(7-n31) and 0≤m32≤(7-n32).)

Regardless of _formula ( ^X2 ) or formula ( ^X3 ),

In the formula (X2), n21 and n22 each independently represent an integer of 0 to 2. In particular, from the viewpoint of realizing a low-viscosity diester compound, it is preferable that at least one of n21 and n22 is 1 or more. In one suitable embodiment, n21 and n22 are each independently 1 or 2, and more preferably, both n21 and n22 are 1.

When n21 or n22 is 1 or more, the bonding position of R ¹ to the benzene ring is not particularly limited, but from the viewpoint of realizing a diester compound with lower viscosity, in the relationship with the bonding position of the oxy group of the ester bond It is preferable that it is an ortho position or a meta position, and an ortho position is more preferable.

In formula (X2), m21 and m22 represent integers satisfying 0≤m21≤(5-n21) and 0≤m22≤(5-n22).

In formula (X3), n31 and n32 each independently represent an integer of 0 to 2. In particular, from the viewpoint of realizing a low-viscosity diester compound, it is preferable that at least one of n31 and n32 is 1 or more. In one suitable embodiment, n31 and n32 are each independently 1 or 2, and more preferably, both n31 and n32 are 1.

When n31 or n32 is 1 or more, the bonding position of R ¹ to the naphthalene ring is not particularly limited, but from the viewpoint of realizing a diester compound with lower viscosity, in the relationship with the bonding position of the oxy group of the ester bond, It is preferable that it is an ortho position or a meta position, and an ortho position is more preferable.

In formula (X3), m31 and m32 represent integers satisfying 0≤m31≤(7-n31) and 0≤m32≤(7-n32).

In one suitable embodiment, in formula (X2):

i) X _core is an alkylene group with 6 or more carbon atoms which may have a substituent,

ii) (a) at least one of n21 and n22 is 1 or 2, R ¹ is each independently an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms, and m21 and m22 is each independently an integer of 0 to 2, and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group, or (b) n21 and n22 are 0, and m21 and m22 is each independently an integer of 0 to 5, and ^R2 is each independently selected from a halogen atom, an alkyl group, and an aryl group.

In a more suitable embodiment, in formula (X2),

i ₎

ii) (a) At least one of n21 and n22 is 1 or 2, R ¹ is each independently an alkenyl group having 2 to 10 carbon atoms, and m21 and m22 are each independently an integer of 0 to 2. and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group, or (b) n21 and n22 are 0, and m21 and m22 are each independently an integer of 0 to 5. and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group.

In one suitable embodiment, in formula (X3):

i) X _core is an alkylene group with 6 or more carbon atoms which may have a substituent,

ii) (a) at least one of n31 and n32 is 1 or 2, R ¹ is each independently an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms, and m31 and m32 is each independently an integer of 0 to 2, and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group, or (b) n31 and n32 are 0, and m31 and m32 is each independently an integer of 0 to 7, and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group.

In a more suitable embodiment, in formula (X3),

i ₎

ii) (a) At least one of n31 and n32 is 1 or 2, R ¹ is each independently an alkenyl group having 2 to 10 carbon atoms, and m31 and m32 are each independently an integer of 0 to 2. and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group, or (b) n31 and n32 are 0, and m31 and m32 are each independently an integer of 0 to 7. and R ² is each independently selected from a halogen atom, an alkyl group, and an aryl group.

In the diester compound of the present invention, the equivalent weight of the oxycarbonyl group (active ester equivalent weight) is preferably 150 g/eq. or more, more preferably 160 g/eq. or more, more preferably 180 g/eq. Above, 200g/eq. That's it. The upper limit of the equivalent weight of the oxycarbonyl group is, for example, 1000 g/eq. Below, 750g/eq. Below, 700g/eq. Below, 600g/eq. or less than or equal to 500 g/eq. This can be done as follows.

The molecular weight (number average molecular weight Mn in the case of distribution) of the diester compound of the present invention is preferably 2000 or less, more preferably 1500 or less, from the viewpoint of mixing and using it in a resin composition as a crosslinking agent for a crosslinkable resin. More preferably, it is 1400 or less, 1200 or less, or 1000 or less. The lower limit of the molecular weight is not particularly limited and can be, for example, 300 or more, 320 or more. The molecular weight can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC).

Below, an example of the synthesis procedure for the diester compound of the present invention is shown.

In one embodiment, the diester compound of the present invention is:

(A) a divalent aliphatic carboxylic acid compound or a divalent aliphatic carboxylic acid halide compound,

(B) Monovalent aromatic hydroxy compounds that may have substituents

It can be obtained through a condensation reaction.

-(A) Divalent aliphatic carboxylic acid (halide) compound-

The component (A) is a divalent aliphatic carboxylic acid compound or a divalent aliphatic carboxylic acid halide compound, and is represented by the following formula (X4).

(In the formula, X _core is as described above, and Z represents a hydroxy group or a halogen atom.)

As the component (A), any divalent aliphatic carboxylic acid (halide) compound may be used depending on the target core unit X _core . Suitable examples of X _core are as described above. For example, if the target core _unit It is good to use .

-(B) Monovalent aromatic hydroxy compound which may have a substituent-

(B) Component is a monovalent aromatic hydroxy compound which may have a substituent, and is represented by the following formula (X5).

(During the ceremony,

Rings Ar, R ¹ and R ² are as described above,

n represents an integer from 0 to 2,

m represents an integer that satisfies 0≤m≤(p-n), assuming that p is the number of hydrogen atoms that can be substituted for ring Ar.)

As the component (B), any aromatic monomer may be used depending on the intended blocking unit. Rings Ar, R ¹ and R ² are as described above. For example, as such an aromatic monool, when the target blocking unit is a benzene ring having one alkenyl group with 2 to 6 carbon atoms as a substituent, n is 1 and R ¹ is a ring with 2 to 6 carbon atoms. It is good to use alkenyl phenol compounds, such as vinyl phenol, allyl phenol, 1-propenyl phenol, butenyl phenol, pentenyl phenol, and hexenyl phenol. In addition, when the target blocking unit is a benzene ring having a fluorine atom as a substituent, a phenolic compound in which m is 1 to 5 and R ² is a fluorine atom, for example, pentafluorophenol, tetrafluorophenol, trifluorophenol, It is good to use something like lophenol.

The condensation reaction may proceed in a solvent-free system without using a solvent, or may proceed in an organic solvent system using an organic solvent. Examples of the organic solvent used in the condensation reaction include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; Acetic acid ester solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; Carbitol-based solvents such as Cellosolve and butylcarbitol; Aromatic hydrocarbon solvents such as toluene and xylene; Amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone can be mentioned. Organic solvents may be used individually, or may be used in combination of two or more types.

In the condensation reaction, a base may be used. Examples of the base include alkali metal hydroxides such as sodium hydroxide (caustic soda) and potassium hydroxide; and tertiary amines such as triethylamine, pyridine, and N,N-dimethyl-4-aminopyridine (DMAP). Bases may be used individually or in combination of two or more types.

In the condensation reaction, a condensing agent or an interlayer transfer catalyst may also be used. These may be any conventionally known material that can be used in an esterification reaction.

The reaction temperature in the condensation reaction is not particularly limited as long as the condensation reaction proceeds, and may be, for example, in the range of 0 to 80°C. In addition, the reaction time in the condensation reaction is not particularly limited as long as the structure of the target diester compound is achieved, and may be, for example, in the range of 30 minutes to 8 hours.

The diester compound may be purified after the condensation reaction. For example, after the condensation reaction, a purification process such as water washing or microfiltration may be performed to remove by-product salts and excess starting materials from the system. In detail, after the condensation reaction, the amount of water necessary to dissolve the by-product salt is added, and the liquid is separated while standing to remove the water layer. Additionally, if necessary, add acid to neutralize and repeat washing. Afterwards, the diester compound can be obtained by going through a dehydration process using a chemical or azeotropic agent, purifying it by microfiltration to remove impurities, and then distilling off the organic solvent as needed. It may be used as a solvent for the resin composition without completely removing the organic solvent.

The diester compound of the present invention is characterized by low viscosity. For example, when measured with a vibration viscometer as described in the section below (viscosity measurement conditions during heating), the viscosity of the diester compound of the present invention at 75°C is preferably 1000 mPa·s or less, more preferably Preferably it may be 500 mPa·s or less, more preferably 300 mPa·s or less, 200 mPa·s or less, 150 mPa·s or less, 100 mPa·s or less, 80 mPa·s or less, 60 mPa·s or less, or 50 mPa·s or less.

In a suitable embodiment where at least one (preferably both) of the first and second blocking units is an aromatic ring having an unsaturated aliphatic hydrocarbon group as a substituent, a particularly low viscosity can be exhibited. In this preferred embodiment, the diester compound of the present invention is liquid at room temperature (25°C). For example, when measured with an E-type viscometer (100 rpm) as described in the (Viscosity measurement conditions) column described later, the viscosity of the diester compound of the present invention at 25°C is preferably 2000 mPa·s or less, More preferably, it may be 1500 mPa·s or less, and even more preferably 1000 mPa·s or less, 800 mPa·s or less, 600 mPa·s or less, 500 mPa·s or less, or 400 mPa·s or less. In a particularly suitable embodiment in which both the first and second blocking units are aromatic rings having an unsaturated aliphatic hydrocarbon group as a substituent, the diester compound of the present invention can exhibit a lower viscosity, and the viscosity at 25°C is: For example, it is possible to lower it to 300 mPa·s or less, 250 mPa·s or less, 200 mPa·s or less, 150 mPa·s or less, or 100 mPa·s or less. Therefore, in one suitable embodiment, the viscosity of the diester compound of the present invention at 25°C is 300 mPa·s or less.

The diester compound of the present invention has the advantages of an ester compound in that it forms a cured product with excellent dielectric properties when combined with a crosslinkable resin, but has low viscosity and has good fluidity when combined with a crosslinkable resin. The composition can be realized, and furthermore, the occurrence of flow marks or unfilled parts during molding such as seal molding can be suppressed. Additionally, the diester compound of the present invention can form a cured product with good toughness and flexibility when combined with a crosslinkable resin. In addition, even when the content of the inorganic filler is high, a resin composition showing good fluidity at the molding temperature can be formed, and a cured product with excellent heat resistance and moisture resistance, a lower dielectric loss tangent, low warpage, and good heat dissipation can be realized. You can. Therefore, in a suitable embodiment, the diester compound of the present invention can be suitably used as a resin crosslinking agent.

[Resin composition]

A resin composition can be produced using the diester compound of the present invention. The present invention also provides such a resin composition.

The resin composition of the present invention includes a diester compound (X) and a crosslinkable resin (Y), and the diester compound (X) is a diester compound of the present invention, that is, a diester compound represented by the formula (X). It is characterized as an ester compound.

Details of the diester compound (X), including suitable examples of the core unit and the first and second blocking units, and suitable aspects of the general formula, are as described in the [Diester compound] section above.

In the resin composition of the present invention, the type of crosslinkable resin (Y) is not particularly limited as long as it can be crosslinked in combination with the diester compound (X). In combination with the diester compound (X), from the viewpoint of forming a cured product showing excellent dielectric properties and at the same time showing good fluidity during molding, the crosslinkable resin (Y) is a thermosetting resin and a radical polymerizable resin. It is preferable that there is at least one type selected from the group consisting of.

As the thermosetting resin and radical polymerizable resin, you may use a known resin used when forming the insulating layer of a printed wiring board or semiconductor chip package. Hereinafter, thermosetting resins and radical polymerizable resins that can be used as the crosslinkable resin (Y) will be described.

Examples of thermosetting resins include epoxy resin, benzocyclobutene resin, epoxy acrylate resin, urethane acrylate resin, urethane resin, cyanate resin, polyimide resin, benzoxazine resin, unsaturated polyester resin, phenol resin, Melamine resin, silicone resin, phenoxy resin, etc. can be mentioned. Thermosetting resins may be used individually, or may be used in combination of two or more types. Among them, in combination with the diester compound (X), the crosslinkable resin (Y) preferably contains an epoxy resin from the viewpoint of exhibiting good fluidity during molding and excellent dielectric properties after curing. do.

The type of epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups per molecule. As epoxy resins, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, phenol novolak type epoxy resin, tert-butyl-catechol type epoxy resin, naphthol type. Epoxy resin, naphthalene type epoxy resin, naphthylene ether type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, cresol novolak type epoxy resin, biphenyl type epoxy resin, phenol aralkyl type epoxy resin, Biphenyl aralkyl type epoxy resin, fluorene skeleton type epoxy resin, dicyclopentadiene type epoxy resin, anthracene type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spiro Ring-containing epoxy resin, cyclohexanedimethanol type epoxy resin, trimethylol type epoxy resin, halogenated epoxy resin, etc. are mentioned. According to the resin composition of the present invention containing the diester compound (X), regardless of the type of epoxy resin, it can exhibit good fluidity during molding and provide excellent dielectric properties after curing.

Epoxy resins can be classified into liquid epoxy resins at a temperature of 20°C (hereinafter referred to as “liquid epoxy resins”) and solid epoxy resins at a temperature of 20°C (hereinafter referred to as “solid epoxy resins”). The resin composition of the present invention may contain only a liquid epoxy resin as the crosslinkable resin (Y), may contain only a solid epoxy resin, or may contain a combination of a liquid epoxy resin and a solid epoxy resin. When a combination of liquid epoxy resin and solid epoxy resin is included, the mixing ratio (liquid phase: solid phase) is in the range of 20:1 to 1:20 in mass ratio (preferably 10:1 to 1:10, more preferably 3 :1 to 1:3) may be used.

The epoxy group equivalent of the epoxy resin is preferably 50 g/eq. to 2000 g/eq., more preferably 60 g/eq. to 1000 g/eq., more preferably 80 g/eq. to 500 g/eq. The epoxy group equivalent is the mass of the epoxy resin containing 1 equivalent of the epoxy group, and can be measured according to JIS K7236.

The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and still more preferably 400 to 1,500. The Mw of the epoxy resin can be measured as a polystyrene conversion value by GPC method.

The type of radically polymerizable resin is not particularly limited as long as it has one or more (preferably two or more) radically polymerizable unsaturated groups per molecule. Examples of the radically polymerizable resin include radically polymerizable unsaturated groups such as maleimide group, vinyl group, allyl group, styryl group, vinylphenyl group, acryloyl group, methacryloyl group, fumaroyl group, and maleoyl group. Resins having one or more types selected from: Among them, in combination with the diester compound (X), the crosslinkable resin (Y) is a maleimide resin, (meta) from the viewpoint of exhibiting good fluidity during molding and excellent dielectric properties after curing. It is preferable that it contains at least one type selected from acrylic resin and styryl resin.

As a maleimide resin, as long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl group) per molecule, The type is not particularly limited. As maleimide resin, for example, "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all designer Moleculars) maleimide resins containing an aliphatic skeleton with 36 carbon atoms derived from dimerdiamine, such as those produced by the company; A maleimide resin containing an indan skeleton, described in Invention Association Public Notice No. 2020-500211; “MIR-3000-70MT” (manufactured by Nippon Kayaku Co., Ltd.), “BMI-4000” (manufactured by Yamato Kasei Co., Ltd.), “BMI-80” (manufactured by KAI Kasei Co., Ltd.), etc., directly bonded to the nitrogen atom of the maleimide group. and a maleimide resin containing an aromatic ring skeleton.

The type of (meth)acrylic resin is not particularly limited as long as it has one or more (preferably two or more) (meth)acryloyl groups in one molecule. Here, the term “(meth)acryloyl group” is a general term for acryloyl group and methacryloyl group. As methacrylic resin, for example, "A-DOG" (manufactured by Shinnakamura Chemical Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Co., Ltd.), "NPDGA", "FM-400", and "R" (meth)acrylic resins such as "-687", "THE-330", "PET-30", and "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.).

The type of styryl resin is not particularly limited as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups per molecule. Examples of the styryl resin include styryl resins such as "OPE-2St", "OPE-2St 1200", and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Co., Ltd.).

The resin composition of the present invention may contain only a thermosetting resin as the crosslinkable resin (Y), may contain only a radically polymerizable resin, or may contain a combination of a thermosetting resin and a radically polymerizable resin.

In the resin composition of the present invention, the mass ratio ((X)/(Y)) of the diester compound (X) to the crosslinkable resin (Y) is preferably 0.8 or more, and more preferably 0.9 or more. , it may be 1 or more, 1.1 or more, or 1.2 or more. The upper limit of the mass ratio ((X)/(Y)) may be, for example, 2 or less, 1.9 or less, 1.8 or less. Therefore, in one embodiment, the diester compound for the crosslinkable resin (Y) The mass ratio ((X)/(Y)) of (X) is 0.8 to 2.0.

The resin composition of the present invention may further contain an inorganic filler. By containing an inorganic filler, the linear thermal expansion coefficient and dielectric loss tangent can be further reduced. Additionally, by containing an inorganic filler with high thermal conductivity, a cured product with excellent heat dissipation properties can be achieved.

Inorganic fillers include, for example, silica, alumina, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum borate, barium titanate, strontium titanate, and titanic acid. Calcium, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, calcium zirconate, etc. may be selected depending on the specific use. Inorganic fillers may be used individually or in combination of two or more types. Commercially available inorganic fillers include, for example, “UFP-30” (manufactured by Denka Chemical Co., Ltd.); 「YC100C」, 「YA050C」, 「YA050C-MJE」, 「YA010C」, 「SC2500SQ」, 「SC4050-SX」, 「SO-C4」, 「SO-C2」, 「SO-C1」, 「SC-C2」 」(all manufactured by Adomatex); “Real-pencil NSS-3N”, “Real-pencil NSS-4N”, “Real-pencil NSS-5N” (manufactured by Tokuyama Corporation), and “DAW-0525” (manufactured by Denka Co., Ltd.).

The average particle diameter of the inorganic filler may be determined within a suitable range depending on the specific use. For example, when forming an interlayer insulating layer of a printed wiring board or a redistribution layer of a semiconductor chip package, the surface of the cured product (insulating layer) becomes low-illuminance, and from the viewpoint of facilitating the formation of fine wiring, the average particle size of the inorganic filler The diameter is preferably 5 μm or less, more preferably 2 μm or less, and even more preferably 1 μm or less. In addition, when forming the sealing layer of a semiconductor chip package, from the viewpoint of improving fluidity during sealing molding, the average particle diameter of the inorganic filler is preferably 15 μm or less, more preferably 14 μm or less, and even more preferably Typically, it is 12㎛ or less, 10㎛ or less, or 8㎛ or less. The lower limit of the average particle diameter is not particularly limited and may be determined depending on the specific use, for example, 0.01 μm or more, 0.02 μm or more, 0.03 μm or more, 0.05 μm or more, or 0.1 μm or more. The average particle diameter of the inorganic filler can be measured by a laser diffraction/scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be prepared on a volume basis using a laser diffraction scattering type particle size distribution measuring device, and the median diameter can be measured as the average particle diameter. The measurement sample can preferably be one in which an inorganic filler is dispersed in water by ultrasonic waves. As a laser diffraction scattering type particle size distribution measuring device, LA-950 manufactured by Horiba Sesakusho, etc. can be used.

Inorganic fillers include aminosilane coupling agents, ureidosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, vinyl silane coupling agents, styryl silane coupling agents, acrylate silane coupling agents, and isocyanates. It is preferable to treat the surface with a surface treatment agent such as a silane-based coupling agent, sulfide silane-based coupling agent, organosilazane compound, or titanate-based coupling agent to improve moisture resistance and dispersibility.

When the resin composition of the present invention contains an inorganic filler, the content of the inorganic filler in the resin composition may be determined according to the characteristics required for the resin composition, but when the non-volatile component in the resin composition is 100% by mass, for example For example, it is 5 mass% or more, 10 mass% or more, preferably 30 mass% or more, more preferably 40 mass% or more, and even more preferably 50 mass% or more. According to the resin composition of the present invention containing the diester compound (X) having a core unit made of a divalent aliphatic group, the content of the inorganic filler can be increased while ensuring good fluidity during molding. The content of the inorganic filler in the resin composition may be increased to, for example, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75% by mass or more, or 80% by mass or more. Accordingly, the resin composition of the present invention satisfies narrow gap filling properties, has a lower dielectric loss tangent, is excellent in heat resistance, moisture resistance, and low warpage, and, depending on the type of inorganic filler, produces a cured product with high heat dissipation properties. It can be realized. The upper limit of the content of the inorganic filler in the resin composition is not particularly limited, but can be, for example, 95% by mass or less, 90% by mass or less, etc.

The resin composition of the present invention may further contain a resin crosslinking agent other than the diester compound (X).

Resin crosslinking agents other than diester compound (X) include "TD2090", "TD2131" (manufactured by DIC), "MEH-7600", "MEH-7851", and "MEH-8000H" (manufactured by Maywa Kasei), “NHN”, “CBN”, “GPH-65”, “GPH-103” (manufactured by Nippon Kayaku), “SN170”, “SN180”, “SN190”, “SN475”, “SN485”, “SN495”, Phenol-based curing agents such as “SN375”, “SN395” (manufactured by Nittetsu Chemical & Materials), “LA7052”, “LA7054”, “LA3018”, and “LA1356” (manufactured by DIC); Benzoxazine-based crosslinking agents such as “F-a”, “P-d” (manufactured by Shikoku Kasei Co., Ltd.), and “HFB2006M” (manufactured by Showa Kobunshi Co., Ltd.); Acid anhydride crosslinking agents such as methylhexahydrophthalic anhydride, methylnadic anhydride, and hydrogenated methylnadic anhydride; Cyanate ester crosslinking agents such as PT30, PT60, and BA230S75 (manufactured by Lonza Japan); and benzoxazine-based crosslinking agents.

When the resin composition of the present invention contains a resin cross-linking agent other than the diester compound (X), the content of the resin cross-linking agent in the resin composition may be determined according to the characteristics required for the resin composition, but the non-volatile component in the resin composition may be determined. When said to be 100 mass%, it is preferably 40 mass% or less, more preferably 20 mass% or less, and even more preferably 10 mass% or less, with the lower limit being 0.01 mass% or more, 0.05 mass% or more, and 0.1 mass%. This can be done as above.

The resin composition of the present invention may further contain a crosslinking accelerator. By including a crosslinking accelerator, the crosslinking time and crosslinking temperature can be adjusted efficiently.

Examples of the crosslinking accelerator include organic phosphine compounds such as “TPP”, “TPP-K”, “TPP-S”, and “TPTP-S” (manufactured by Hokko Chemical Co., Ltd.); “Curesol 2MZ”, “2E4MZ”, “Cl1Z”, “Cl1Z-CN”, “Cl1Z-CNS”, “Cl1Z-A”, “2MZ-OK”, “2MA-OK”, “2PHZ” (Shikoku Ka Imidazole compounds such as those manufactured by Seiko Corporation; Amine adduct compounds such as Novacure (manufactured by Asahi Kaseiko Co., Ltd.) and Fujicure (manufactured by Fuji Kaseiko Co., Ltd.); 1,8-diazabicyclo[5,4,0]undecene-7,4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 4-dimethylaminopyridine, etc. amine compounds; Examples include organometallic complexes or organometallic salts such as cobalt, copper, zinc, iron, nickel, manganese, and tin.

When the resin composition of the present invention contains a crosslinking accelerator, the content of the crosslinking accelerator in the resin composition may be determined depending on the characteristics required for the resin composition, but if the nonvolatile component in the resin composition is 100% by mass, it is preferable is 10 mass% or less, more preferably 5 mass% or less, further preferably 1 mass% or less, and the lower limit can be 0.001 mass% or more, 0.01 mass% or more, 0.05 mass% or more, etc.

The resin composition of the present invention may further contain optional additives. Examples of such additives include organic fillers such as rubber particles; Radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; Thermoplastic resins such as phenoxy resin, polyvinyl acetal resin, polysulfone resin, polyether sulfone resin, polyphenylene ether resin, polyether ether ketone resin, and polyester resin; Organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; Colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; Polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; Leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; Thickeners such as bentone and montmorillonite; Antifoaming agents such as silicone-based defoaming agents, acrylic-based defoaming agents, fluorine-based defoaming agents, and vinyl resin-based defoaming agents; UV absorbers such as benzotriazole-based UV absorbers; Adhesion improvers such as urea silane; Adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; Antioxidants such as hindered phenol antioxidants; Fluorescent whitening agents such as stilbene derivatives; Surfactants such as fluorine-based surfactants and silicone-based surfactants; Flame retardants such as phosphorus-based flame retardants (e.g., phosphoric acid ester compounds, phosphazene compounds, phosphinic acid compounds, red), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); Phosphate ester-based dispersant, polyoxyalkylene-based dispersant, acetylene-based dispersant, silicone-based dispersant, anionic dispersant, cationic dispersant; Stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers can be mentioned. The content of these additives may be determined depending on the properties required for the resin composition.

The resin composition of the present invention may further contain an organic solvent as a volatile component. Examples of organic solvents include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; Ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; Alcohol-based solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; Ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; Ester alcohol-based solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol-based solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butylcarbitol); amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; Sulfoxide-based solvents such as dimethyl sulfoxide; Nitrile-based solvents such as acetonitrile and propionitrile; Aliphatic hydrocarbon-based solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon-based solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. Organic solvents may be used individually, or may be used in combination of two or more types.

When the resin composition of the present invention contains an organic solvent, the content of the organic solvent in the resin composition may be determined depending on the characteristics required for the resin composition, but when all components in the resin composition are assumed to be 100% by mass, for example , 60 mass% or less, 40 mass% or less, 30 mass% or less, 20 mass% or less, 15 mass% or less, 10 mass% or less, etc.

Here, in order to reduce the viscosity of the resin composition, the resin composition has been prepared by adding an organic solvent as a diluent. When such a resin composition is used to form the insulating layer of a semiconductor chip package or printed wiring board, voids are generated during the film forming process or sealing molding process, large-scale disposal facilities for organic solvents are required, or the resulting insulation is required. It causes defects such as organic solvent remaining in the layer. On the other hand, according to the resin composition of the present invention containing the diester compound ( It is preferable because it can exhibit good fluidity. The content of the organic solvent in the resin composition of the present invention is, for example, less than 10 mass%, 8 mass% or less, 6 mass% or less, 5 mass% or less, 4 mass% or less, 2 mass% or less, 1 mass% or less. Alternatively, it may be set as low as 0.5% by mass or less, or 0% by mass (solvent-free system) may be used.

The resin composition of the present invention is prepared by appropriately mixing the necessary components among the above components and, if necessary, kneading means such as three rolls, ball mills, bead mills, sand mills, etc., or super mixers, planetary mixers, etc. It can be prepared by kneading or mixing using a stirring means.

The resin composition of the present invention comprising a diester compound (X) and a crosslinkable resin (Y) in combination exhibits good fluidity during molding and can provide excellent dielectric properties after curing.

In one embodiment, the cured product of the resin composition of the present invention is characterized by a low dielectric constant (Dk). For example, when measured at 5.8 GHz and 23°C as described in the [Dielectric Properties] column described later, the dielectric constant (Dk) of the cured product of the resin composition of the present invention is preferably 3.3 or less, 3.2 or less, and 3.1. It can be less than or equal to 3.0, less than or equal to 2.9, or less than or equal to 2.8.

In one embodiment, the cured product of the resin composition of the present invention exhibits the characteristic of low dielectric loss tangent (Df). For example, when measured at 5.8 GHz and 23°C as described in the [Dielectric Properties] section described later, the dielectric loss tangent (Df) of the cured product of the resin composition of the present invention is preferably 0.01 or less, 0.008 or less, It can be 0.007 or less, 0.006 or less, 0.005 or less, or 0.004 or less.

In one embodiment, the cured product of the resin composition of the present invention is characterized by high thermal conductivity. For example, when measured by the hot disk method as described in the [Thermal Conductivity] column described later, the thermal conductivity of the cured product of the resin composition of the present invention is preferably 2.5 W/mK or more, 2.6 W/mK or more, It can be greater than 2.8W/mK, greater than 3W/mK, greater than 3.1W/mK, or greater than 3.2W/mK.

The resin composition of the present invention can be suitably used as a resin composition for sealing a semiconductor chip (semiconductor sealing resin composition). The resin composition of the present invention can also be suitably used as a resin composition for a redistribution forming layer (resin composition for a redistribution forming layer) as an insulating layer for forming a redistribution layer in a semiconductor chip package. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for an insulating layer of a printed wiring board), and a resin composition for forming an interlayer insulating layer of a printed wiring board (a resin composition for forming an interlayer insulating layer of a printed wiring board). It can be more suitably used as a resin composition for an interlayer insulating layer. The resin composition of the present invention can be suitably used even when the printed wiring board is a circuit board with built-in components. The resin composition of the present invention can also be widely used in applications requiring a resin composition, such as sheet-like laminated materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, and component filling resins. .

[Sheet-like lamination material (resin sheet, prepreg)]

The resin composition of the present invention may be used as is, or may be used in the form of a sheet-like laminated material containing the resin composition.

As the sheet-like laminated material, the resin sheets and prepregs shown below are preferable.

In one embodiment, the resin sheet includes a support and a layer of a resin composition (hereinafter simply referred to as “resin composition layer”) provided on the support, and the resin composition layer is formed of the resin composition of the present invention. It is characterized by

The appropriate value for the thickness of the resin composition layer varies depending on the application, and may be determined appropriately depending on the application. For example, the thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, 120 μm or less, 100 μm or less, 80 μm or less, from the viewpoint of reducing the thickness of the printed wiring board or semiconductor chip package. It is 60㎛ or less or 50㎛ or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but can usually be 1 μm or more, 5 μm or more, etc.

Examples of the support include films made of plastic materials, metal foils, and release papers, and films and metal foils made of plastic materials are preferred.

When using a film made of a plastic material as a support, examples of the plastic material include polyester such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polycarbonate (PC), and polymethyl methacrylate (PMMA). ), acrylic, cyclic polyolefin, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is especially preferable.

When using a metal foil as a support, examples of the metal foil include copper foil, aluminum foil, etc., and copper foil is preferable. As the copper foil, a foil made of the simple metal of copper may be used, or a foil made of an alloy of copper and other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used. good night.

The support may be subjected to mat treatment, corona treatment, or antistatic treatment on the surface joined to the resin composition layer. Additionally, as the support, you may use a support with a mold release layer that has a mold release layer on the surface bonded to the resin composition layer. Examples of the release agent used in the release layer of the support with a release layer include at least one type of release agent selected from the group consisting of alkyd resin, polyolefin resin, urethane resin, and silicone resin. The support with the release layer may be a commercially available product, for example, "SK-1", "AL-5", and "AL-" manufactured by Lintec, which are PET films with a release layer containing an alkyd resin-based release agent as a main component. 7”, “Lumira T60” manufactured by Torres, “Purex” manufactured by Teijin, and “Unifill” manufactured by Unichika.

The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. On the other hand, when using a support body with a release layer, it is preferable that the entire thickness of the support body with a release layer is within the above range.

As a support, you may also use metal foil with a support base material, which is a thin metal foil bonded with a peelable support base material. In one embodiment, the metal foil with a support base material contains a support base material, a peeling layer provided on the support base material, and a metal foil provided on the peeling layer. When using a metal foil with a support base as a support, the resin composition layer is provided on the metal foil.

In the metal foil with a support base, the thickness of the support base is not particularly limited, but examples include copper foil, aluminum foil, stainless steel foil, titanium foil, and copper alloy foil. When copper foil is used as the support base material, electrolytic copper foil or rolled copper foil may be used. In addition, the peeling layer is not particularly limited as long as the metal foil can be peeled from the supporting base material, and examples include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; Organic films, etc. can be mentioned.

In the metal foil with a support base, the material of the metal foil is preferably copper foil or copper alloy foil, for example.

In the metal foil with a support base, the thickness of the support base is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. In addition, the thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

In one embodiment, the resin sheet may further include an arbitrary layer as needed. Examples of such an optional layer include a protective film provided on the side of the resin composition layer that is not bonded to the support (that is, the side opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating a protective film, adhesion of dust or the like to the surface of the resin composition layer and scratches can be suppressed.

For the resin sheet, for example, a liquid resin composition is prepared as is, or a resin varnish is prepared by dissolving the resin composition in an organic solvent, and this is applied on a support using a die coater or the like and further dried to form a resin composition layer. It can be manufactured by:

Examples of the organic solvent include the same organic solvents described as components of the resin composition. Organic solvents may be used individually, or two or more types may be used in combination.

Drying may be performed by known methods such as heating or hot air spraying. Drying conditions are not particularly limited, but the resin composition layer is dried so that the content of the organic solvent is 10% by mass or less, preferably 5% by mass or less. It also varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, but for example, when using a resin composition or resin varnish containing 30% by mass to 60% by mass of an organic solvent, the temperature is 50°C to 150°C for 3 minutes to 10 minutes. By drying, a resin composition layer can be formed.

The resin sheet can be wound into a roll and stored. When the resin sheet has a protective film, it becomes usable by peeling off the protective film.

In one embodiment, the prepreg is formed by impregnating a sheet-like fiber base material with the resin composition of the present invention.

The sheet-like fiber base material used for the prepreg is not particularly limited, and commonly used base materials for prepregs, such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric, can be used. From the viewpoint of reducing the thickness of printed wiring boards or semiconductor chip packages, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, particularly preferably 20 μm or less. am. The lower limit of the thickness of the sheet-like fiber base material is not particularly limited. Usually, it is 10㎛ or more.

Prepreg can be manufactured by known methods such as hot melt method and solvent method.

The thickness of the prepreg can be within the same range as that of the resin composition layer in the above-mentioned resin sheet.

The sheet-like laminate material of the present invention can be suitably used for sealing semiconductor chips (for semiconductor sealing) and can be suitably used for a redistribution forming layer as an insulating layer for forming a rewiring layer. The sheet-like laminate material of the present invention can also be suitably used to form an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and to form an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board). ) can be used more appropriately.

[Semiconductor chip package]

The semiconductor chip package of the present invention includes a sealing layer made of a cured product of the resin composition of the present invention. As described above, the semiconductor chip package of the present invention may also include an insulating layer for forming a rewiring layer (rewiring forming layer) made of a cured product of the resin composition of the present invention.

A semiconductor chip package can be manufactured, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. To form the sealing layer in step (3) or the redistribution layer in step (5), the resin composition and resin sheet of the present invention may be used. Hereinafter, an example of forming a sealing layer or a rewiring layer using a resin composition or a resin sheet will be shown. However, the technology for forming a sealing layer or a rewiring layer in a semiconductor chip package is known, and those skilled in the art will know how to use the resin composition of the present invention. A semiconductor package can be manufactured according to known techniques using or resin sheets.

(1) A process of laminating a temporarily fixed film on a substrate,

(2) A process of temporarily fixing a semiconductor chip on a temporarily fixing film,

(3) Process of forming a sealing layer on the semiconductor chip,

(4) A process of peeling the base material and temporarily fixed film from the semiconductor chip,

(5) A process of forming a redistribution layer as an insulating layer on the surface of the semiconductor chip from which the substrate and temporarily fixed film are peeled, and

(6) Process of forming a redistribution layer as a conductor layer on the redistribution formation layer

-Process (1)-

The material used for the base material is not particularly limited. As a base material, silicon wafer; glass wafer; glass substrate; Metal substrates such as copper, titanium, stainless steel, and cold rolled steel (SPCC); A substrate in which glass fibers are impregnated with an epoxy resin and then heat cured (for example, an FR-4 substrate); and a substrate made of bismaleimide triazine resin (BT resin).

The material of the temporarily fixed film is not particularly limited as long as it can be peeled from the semiconductor chip in step (4) and can temporarily fix the semiconductor chip. A commercially available product can be used as the temporarily fixed film. Commercially available products include Liva Alpha manufactured by Nitto Denko Co., Ltd.

-Process (2)-

The semiconductor chip is temporarily fixed on the temporarily fixed film so that the electrode pad surface is bonded to the temporarily fixed film. Temporarily fixing a semiconductor chip can be performed using a known device such as a flip chip bonder or die bonder. The layout and number of batches of semiconductor chips can be appropriately set according to the shape and size of the temporarily fixed film, the number of target semiconductor packages produced, etc., for example, by arranging them in a matrix of multiple rows and multiple columns. It can be temporarily fixed.

-Process (3)-

The resin composition of the present invention is applied on a semiconductor chip, or the resin composition layer of the resin sheet of the present invention is laminated on the semiconductor chip and cured (for example, heat cured) to form a sealing layer.

By using the resin composition of the present invention containing the diester compound ( It can exhibit good fluidity during molding.

For example, when used in the form of a resin sheet, the lamination of the semiconductor chip and the resin sheet can be performed by removing the protective film of the resin sheet and then heat-pressing the resin sheet to the semiconductor chip from the support side. As a member for heat-pressing the resin sheet to the semiconductor chip (hereinafter also referred to as “heat-pressing member”), a heated metal plate (SUS head plate, etc.) or a metal roll (SUS roll) can be used, for example. On the other hand, it is preferable not to press the heat-compression member directly on the resin sheet, but to press it through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the semiconductor chip. The lamination of the semiconductor chip and the resin sheet may be performed by a vacuum lamination method, and the lamination conditions are the same as those described later in relation to the method of manufacturing a printed wiring board, and the preferable range is also the same.

After lamination, the resin composition is heat-cured to form a sealing layer. The conditions for thermal curing are the same as those for thermal curing described later in relation to the method of manufacturing a printed wiring board.

The support of the resin sheet may be peeled off after laminating the resin sheet on the semiconductor chip and heat curing, or may be peeled before laminating the resin sheet on the semiconductor chip.

When forming a sealing layer by applying the resin composition of the present invention, the application conditions may be the same as the application conditions for forming the resin composition layer described in relation to the resin sheet of the present invention. By using the resin composition of the present invention, good fluidity can be achieved at application and molding temperatures.

-Process (4)-

The method of peeling off the base material and the temporarily fixed film can be appropriately changed depending on the material of the temporarily fixed film, etc., for example, a method of peeling the temporarily fixed film by heating and foaming (or expanding), and irradiating ultraviolet rays from the base material side. A method of lowering the adhesive force of the temporarily fixed film and peeling it off is included.

In the method of peeling a temporarily fixed film by heating and foaming (or expanding), the heating conditions are usually 100 to 250°C for 1 to 90 seconds or 5 to 15 minutes. In addition, in the method of peeling off the temporarily fixed film by irradiating ultraviolet rays from the substrate side to reduce the adhesive force of the temporarily fixed film, the irradiation amount of ultraviolet rays is usually 10 mJ/cm2 to 1000 mJ/cm2.

-Process (5)-

The material forming the redistribution forming layer (insulating layer) is not particularly limited as long as it has insulating properties at the time of forming the redistribution forming layer (insulating layer), and from the viewpoint of ease of manufacturing a semiconductor chip package, photosensitive resin and thermosetting resin are preferable. do. You may form a redistribution formation layer using the resin composition and resin sheet of this invention.

After forming the redistribution forming layer, a via hole may be formed in the redistribution forming layer in order to interlayer connect the semiconductor chip and the conductor layer described later. The via hole may be formed by a known method depending on the material of the redistribution formation layer.

-Process (6)-

The material of the conductor layer formed on the redistribution formation layer is not particularly limited. In a suitable embodiment, the conductor layer comprises one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin and indium. do. The conductor layer may be a single metal layer or an alloy layer, and the alloy layer may be, for example, an alloy of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium A layer formed of an alloy) may be mentioned. Among them, from the viewpoint of versatility of forming the conductor layer, cost, ease of patterning, etc., a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or a nickel-chromium alloy or copper-nickel alloy , an alloy layer of a copper-titanium alloy is preferable, and a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or an alloy layer of a nickel-chromium alloy is more preferable, and a single metal layer of copper is more preferable. This is more preferable.

The conductor layer may have a single-layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

The thickness of the conductor layer depends on the design of the desired semiconductor chip package, but is generally 1 μm to 35 μm, preferably 1 μm to 20 μm.

In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the redistribution layer using a conventionally known technique such as a semi-additive method or a full additive method, and from the viewpoint of ease of manufacture, It is preferable to form it by the semi-additive method. Hereinafter, an example of forming a conductor layer by a semi-additive method will be shown.

First, a plating seed layer is formed on the surface of the redistribution formation layer by electroless plating. Next, on the formed plating seed layer, a mask pattern is formed to expose a portion of the plating seed layer corresponding to the desired wiring pattern. After forming a metal layer by electrolytic plating on the exposed plating seed layer, the mask pattern is removed. Thereafter, the unnecessary plating seed layer can be removed by etching or the like to form a conductor layer (rewiring layer) having a desired wiring pattern.

On the other hand, steps (5) and (6) may be repeatedly performed to alternately stack (build up) the conductor layer (rewiring layer) and the rewiring forming layer (insulating layer).

In manufacturing a semiconductor chip package, (7) forming a solder resist layer on a conductor layer (rewiring layer), (8) forming a bump, (9) attaching a plurality of semiconductor chip packages to each semiconductor chip package. A process of dicing and dividing into pieces may be additionally performed. These processes may be performed according to various methods known to those skilled in the art that are used in the production of semiconductor chip packages.

The above is an example of manufacturing using the chip 1st (Chip-1 ^st ) method, which is a method of first preparing a semiconductor chip and forming a redistribution layer on the electrode pad surface. In addition to the above chip 1st method, the semiconductor chip package of the present invention includes first providing a rewiring layer, providing a semiconductor chip on the rewiring layer in a state where the electrode pad surface can be electrically connected to the rewiring layer, and sealing it. It may be manufactured using the redistribution layer 1st (RDL-1 ^st ) method. The resin composition and resin sheet of the present invention, which have excellent narrow gap filling properties, can realize a semiconductor chip package with extremely low transmission loss required for 5G applications, regardless of the Chip-1 ^st method or the RDL-1 ^st method.

By molding the sealing layer and the redistribution layer using the resin composition and resin sheet of the present invention, which exhibits good fluidity during molding and has excellent dielectric properties after curing, the semiconductor package is of the fan-in type. Regardless of whether it is a package or a fan-out type package, it is possible to realize a semiconductor chip package with extremely low transmission loss while suppressing the occurrence of flow marks, uncharged parts, and warpage. In one embodiment, the semiconductor chip package of the present invention is a fan-out type package. The resin composition and resin sheet of the present invention can be applied to either a fan-out panel level package (FOPLP) or a fan-out wafer level package (FOWLP). In one embodiment, the semiconductor package of the present invention is a fan-out panel level package (FOPLP). In another embodiment, the semiconductor package of the present invention is a fan-out wafer level package (FOWLP).

[Printed wiring board]

The printed wiring board of the present invention includes an insulating layer made of a cured product of the resin composition of the present invention.

A printed wiring board can be manufactured, for example, by a method including the following steps (I) and (II) using the above resin sheet.

(I) A process of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is bonded to the inner layer substrate.

(II) Process of forming an insulating layer by curing (e.g., heat curing) the resin composition layer.

The “inner layer substrate” used in step (I) is a member that becomes the substrate of the printed wiring board, for example, glass epoxy substrate, metal substrate, polyester substrate, polyimide substrate, BT resin substrate, and thermosetting polyphenylene. Ether substrates, etc. can be mentioned. Additionally, the substrate may have a conductor layer on one or both sides, and this conductor layer may be pattern-processed. An inner layer substrate on which a conductor layer (circuit) is formed on one or both sides of the substrate is sometimes referred to as an “inner layer circuit board.” Additionally, when manufacturing a printed wiring board, an intermediate product on which an insulating layer and/or a conductor layer must be additionally formed is also included in the "inner layer substrate" referred to in the present invention. If the printed wiring board is a circuit board with embedded components, an inner layer board with embedded components may be used.

Lamination of the inner layer substrate and the resin sheet can be performed, for example, by heat-pressing the resin sheet to the inner layer substrate from the support side. As a member for heat-pressing the resin sheet to the inner layer substrate (hereinafter also referred to as “heat-pressing member”), for example, a heated metal plate (SUS head plate, etc.) or a metal roll (SUS roll) can be used. On the other hand, the heat-pressed member may be pressed directly onto the resin sheet, or may be pressed through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the inner layer substrate.

Lamination of the inner layer substrate and the resin sheet may be performed by a vacuum lamination method. In the vacuum lamination method, the heat-pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, and the heat-compression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably is in the range of 0.29 MPa to 1.47 MPa, and the heat compression time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination can be preferably carried out under reduced pressure conditions of 26.7 hPa or less.

Lamination can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressurization laminator manufactured by Meiki Sesakusho, a vacuum applicator manufactured by Nikko Materials, and a batch vacuum pressurization laminator.

After lamination, the laminated resin sheets may be smoothed under normal pressure (under atmospheric pressure), for example, by pressing a heat-pressing member from the support side. The press conditions for the smoothing treatment can be the same as the heat-pressing conditions for the above-mentioned lamination. Smoothing treatment can be performed using a commercially available laminator. On the other hand, the lamination and smoothing treatment may be performed continuously using the commercially available vacuum laminator described above.

The support may be removed between step (I) and step (II), or may be removed after step (II). On the other hand, when metal foil is used as the support, the conductor layer may be formed using the metal foil without peeling the support. In addition, when a metal foil with a support base is used as the support, the support base (and the peeling layer) may be peeled off. Also, the conductor layer can be formed using metal foil.

In step (II), the resin composition layer is cured (for example, heat cured) to form an insulating layer made of a cured resin composition. The curing conditions of the resin composition layer are not particularly limited, and conditions normally employed when forming the insulating layer of a printed wiring board may be used.

For example, the heat curing conditions of the resin composition layer vary depending on the type of the resin composition, etc., but in one embodiment, the curing temperature is preferably 120°C to 250°C, more preferably 150°C to 240°C, and more preferably 150°C to 240°C. Preferably it is 180°C to 230°C. The curing time is preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to heat curing the resin composition layer, the resin composition layer is cured at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°C for 5 minutes or more. Preheating may be performed preferably for 5 minutes to 150 minutes, more preferably for 15 minutes to 120 minutes, and even more preferably for 15 minutes to 100 minutes.

When manufacturing a printed wiring board, (III) a step of perforating the insulating layer, (IV) a step of roughening the insulating layer, and (V) a step of forming a conductor layer may be further performed. These steps (III) to (V) may be performed according to various methods known to those skilled in the art that are used in the manufacture of printed wiring boards. On the other hand, when the support is removed after step (II), the support is removed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). ) may be carried out in between. Additionally, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeated to form a multilayer wiring board.

In another embodiment, the printed wiring board of the present invention can be manufactured using the above-mentioned prepreg. The manufacturing method is basically the same as when using a resin sheet.

Process (III) is a process of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, laser, plasma, etc., depending on the composition of the resin composition used to form the insulating layer. The size and shape of the hole may be determined appropriately according to the design of the printed wiring board.

Process (IV) is a process of roughening the insulating layer. Usually, in this step (IV), smear removal (desmear) is also performed. The procedures and conditions of the roughening process are not particularly limited, and known procedures and conditions normally used when forming the insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by performing swelling treatment with a swelling liquid, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing liquid in this order.

The swelling liquid used in the roughening treatment is not particularly limited, and includes an alkaline solution and a surfactant solution, and is preferably an alkaline solution. As the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferable. Examples of commercially available swelling liquids include "Swelling Deep Securiganth P" and "Swelling Deep Securiganth SBU" manufactured by Atotech Japan. The swelling treatment using the swelling liquid is not particularly limited, but can be performed, for example, by immersing the insulating layer in a swelling liquid of 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid of 40°C to 80°C for 5 to 15 minutes.

The oxidizing agent used in the roughening treatment is not particularly limited, but examples include an alkaline permanganate solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganic acid solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. Additionally, the concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as “Concentrate Compact CP” and “Dosing Solution Securiganth P” manufactured by Atotech Japan.

In addition, as the neutralizing liquid used in the roughening treatment, an acidic aqueous solution is preferable, and examples of commercial products include "Reduction Solution Securigant P" manufactured by Atotech Japan.

Treatment with a neutralizing liquid can be performed by immersing the treated surface that has been roughened with an oxidizing agent in a neutralizing liquid at 30°C to 80°C for 5 to 30 minutes. In terms of workability, etc., a method of immersing an object that has been roughened with an oxidizing agent in a neutralizing liquid at 40°C to 70°C for 5 to 20 minutes is preferable.

Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. Step (V) may be performed in the same manner as step (6) described in connection with the method of manufacturing a semiconductor chip package.

The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

The conductor layer may also be formed using metal foil. When forming a conductor layer using metal foil, step (V) is preferably performed between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. Lamination of the resin composition layer and the metal foil may be performed by a vacuum lamination method. The conditions for lamination may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Thereafter, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by conventionally known techniques such as the subtractive method and the modified semiadditive method.

Metal foil can be manufactured by known methods such as electrolysis and rolling, for example. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Nikko Nisseki Kinzoku Corporation, 3EC-III foil and TP-III foil manufactured by Mitsui Kinzoku Kozan Corporation.

Alternatively, when metal foil or metal foil with a support base is used as a support for the resin sheet, the conductor layer may be formed using the metal foil as described above.

[Semiconductor device]

The semiconductor device of the present invention includes a layer made of a cured product of the resin composition of the present invention. The semiconductor device of the present invention can be manufactured using the semiconductor chip package or printed wiring board of the present invention.

Examples of semiconductor devices include various semiconductor devices used in electrical appliances (e.g., computers, mobile phones, digital cameras, televisions, etc.) and vehicles (e.g., motorcycles, automobiles, trams, ships, aircraft, etc.). there is.

Example

<Example 1> Synthesis of diester compound (A)

Measure out 268 g (2.00 mol) of allylphenol, 239 g (1.00 mol) of sebacic acid dichloride, and 500 g of methyl isobutyl ketone into a 2-liter four-necked round flask equipped with a stirring device, thermometer, dropping funnel, and nitrogen gas inlet. The temperature was raised to 30°C while stirring to uniformly dissolve the contents. 231 g (2.20 mol) of triethylamine was added dropwise thereto. Triethylamine was added dropwise at a temperature of 30°C, and was added dropwise over a period of 1 hour, paying attention to heat generation, following a temperature increase curve so that the liquid temperature reached 60 to 70°C after completion of the dropwise addition. After further stirring was continued at 60 to 70°C for 1 hour, 200 g of distilled water was added to completely dissolve the by-product organic salt. After that, the liquid was transferred to a separatory funnel, and the lower layer (aqueous layer) was subjected to static liquid separation. Next, 200 g of distilled water and 10 g of disodium phosphate were added and permeated vigorously, followed by static separation to remove the lower layer (aqueous layer). Washing with an additional 200 g of distilled water was repeated three times. An appropriate amount of magnesium sulfate (dehydrating agent) was added to the washed reaction solution and dehydrated by shaking vigorously, and the dehydrated reaction solution was microfiltered. Finally, using a rotary evaporator, etc., the reaction solvent was distilled and recovered under high vacuum under reduced pressure (maximum temperature 120°C) using the filtrate to obtain 405 g of diester compound (A) as a liquid compound.

With respect to the obtained diester compound (A), the viscosity was measured using an E-type viscometer (for viscosity at 25°C) and a vibration type viscometer (for viscosity at 75°C) based on the following measurement conditions. The diester compound (A) had a viscosity of 72 mPa·s at 25°C and 12 mPa·s at 75°C.

(Viscosity measurement conditions)

Measuring device: E-type viscometer (“RE-80U” manufactured by Toki Sangyo Co., Ltd.)

Cone plate: radius 24 mm, angle 1.34°

Rotation speed: 100rpm

Temperature: 25℃

(Viscosity measurement conditions during heating)

Measuring device: Vibration viscometer (“VM-10A-L” manufactured by Sekonic Co., Ltd.)

Temperature: 75℃

Additionally, the obtained diester compound (A) was measured by gel permeation chromatography (GPC) and infrared spectroscopy (IR). The GPC chart of this compound is shown in Figure 1A, and the IR chart is shown in Figure 1B. Additionally, in the mass spectrum, a spectrum of m/z=434 corresponding to the molecular weight of the target substance was observed. As a result, it was confirmed that the obtained diester compound (A) had the desired molecular structure shown below.

<Example 2> Synthesis of diester compound (B)

325 g of diester compound (B) was obtained as a solid compound in the same manner as in Example 1, except that 188 g (2.00 mol) of phenol was used instead of allyl phenol.

The melting point of the obtained diester compound (B) was 60°C. Additionally, the viscosity was measured using a vibrating viscometer in the same manner as in Example 1, and the viscosity of the compound at 75°C was 17 mPa·s. The GPC chart of this compound is shown in Figure 2A, and the IR chart is shown in Figure 2B. Additionally, in the mass spectrum, a spectrum of m/z=354 corresponding to the molecular weight of the target substance was observed. As a result, it was confirmed that the obtained diester compound (B) had the desired molecular structure shown below.

<Example 3> Synthesis of diester compound (C)

370 g of diester compound (C) was obtained as a liquid compound in the same manner as in Example 1, except that 211 g (1.00 mol) of suberic acid dichloride was used instead of sebacic acid dichloride.

Regarding the obtained diester compound (C), the viscosity was measured using an E-type viscometer and a vibration viscometer in the same manner as in Example 1, and the viscosity at 25°C was 68 mPa·s and the viscosity at 75°C was 12 mPa·s. It was s. The GPC chart of this compound is shown in Figure 3A, and the IR chart is shown in Figure 3B. Additionally, in the mass spectrum, a spectrum of m/z=406 corresponding to the molecular weight of the target substance was observed. As a result, it was confirmed that the obtained diester compound (C) had the desired molecular structure shown below.

<Example 4> Synthesis of diester compound (D)

In the same manner as in Example 1, except that 288 g (2.00 mol) of 1-naphthol was used instead of allylphenol, 418 g of diester compound (D) was obtained as a solid compound.

The melting point of the obtained diester compound (D) was 68°C. Additionally, the viscosity was measured using a vibrating viscometer in the same manner as in Example 1, and the viscosity of the compound at 75°C was 76 mPa·s. The GPC chart of this compound is shown in Figure 4A, and the IR chart is shown in Figure 4B. Additionally, in the mass spectrum, a spectrum of m/z=454 corresponding to the molecular weight of the target substance was observed. As a result, it was confirmed that the obtained diester compound (D) had the desired molecular structure shown below.

<Example 5> Synthesis of diester compound (E)

505 g of diester compound (E) was obtained as a solid compound in the same manner as in Example 1, except that 368 g (2.00 mol) of pentafluorophenol was used instead of allylphenol.

The melting point of the obtained diester compound (E) was 61°C. Additionally, the viscosity was measured using a vibrating viscometer in the same manner as in Example 1, and the viscosity at 75°C was 19 mPa·s. The GPC chart of this compound is shown in Figure 5A, and the IR chart is shown in Figure 5B. Additionally, in the mass spectrum, a spectrum of m/z=534 corresponding to the molecular weight of the target substance was observed. As a result, it was confirmed that the obtained diester compound (E) had the desired molecular structure shown below.

<Comparative Example 1> Synthesis of diester compound (F)

240 g of diester compound (F) was obtained as a liquid compound in the same manner as in Example 1, except that 203 g (1.00 mol) of isophthalic acid dichloride was used instead of sebacic acid dichloride.

Instead of the obtained diester compound (F), the viscosity was measured using an E-type viscometer and a vibration viscometer in the same manner as in Example 1, and the viscosity at 25°C was 6000 mPa·s and the viscosity at 75°C was 85 mPa·s. It was s. The GPC chart of this compound is shown in Figure 6A, and the IR chart is shown in Figure 6B. Additionally, in the mass spectrum, a spectrum of m/z=398, which corresponds to the molecular weight of the target substance, was observed. As a result, it was confirmed that the obtained diester compound (F) had the molecular structure shown below.

<Examples 6 to 20 and Comparative Examples 2 to 4>

(1) Preparation of resin composition

Using the synthesized diester compounds (A) to (F), a resin composition was prepared by stirring and mixing the compositions shown in Tables 1 to 3 below while heating to 80°C.

(2) Production of cured product

The prepared resin composition was injected into a mold into the gap between two glass plates and cured by heating at 180°C for 90 minutes using a thermal circulation oven to obtain a cured product with a thickness of about 1 mm.

An evaluation test was performed using the obtained cured product and resin composition in the following manner. The results are shown in Tables 1 to 3.

[genetic characteristics]

The cured material was cut into test pieces with a width of 2 mm and a length of 80 mm, and the cavity was measured using a cavity perturbation method dielectric constant measurement device (“CP521” manufactured by Kanto Applied Electronics Development Co., Ltd.) and a network analyzer (“E8362B” manufactured by Agilent Technologies Co., Ltd.). The relative dielectric constant and dielectric loss tangent were measured using the resonance method at a measurement frequency of 5.8 GHz and 23°C. For each cured product, measurements were made on two test pieces (n=2), and the average value was calculated.

[Personality evaluation]

The cured product was cut into test pieces with a width of 30 mm and a length of 80 mm, and the state when bent 180° in half in the long side direction was visually confirmed.

○: No cracks or destruction are visible in the cured product.

×: Cracks and destruction are visible in the hardened product.

[Thermal conductivity]

Each resin composition was placed in a predetermined container and cured by heating at 180°C for 90 minutes using a thermal circulation oven to produce a cylindrical cured product with a thickness of 10 mm and a diameter of ϕ36 mm. The thermal conductivity of the obtained cylindrical cured product was measured by the hot disk method using a thermal property measuring device (“TPS-2500” manufactured by Kyoto Denshi Kogyo Co., Ltd.) in a constant temperature environment of 25°C and 40%RH.

Claims (24)

A diester compound represented by the following formula (X).

(During the ceremony,
X _core represents a divalent aliphatic group,
_X ¹ _{end and} X ² _end each independently represent an aromatic ring which may have a substituent, and at least one of X ^{1 end} and It is an aromatic ring having one or more types selected from as a substituent.) The diester compound according to claim 1, wherein in the X _core , the number of carbon atoms of the divalent aliphatic group is 6 or more. The diester compound according to claim 1 or 2, wherein in the X _core , the divalent aliphatic group is an alkylene group. The diester compound according to any one of claims 1 to 3, wherein both X ¹ _end and X ² _end are aromatic rings having an unsaturated aliphatic hydrocarbon group as a substituent. The diester compound according to any one of claims 1 to 4, wherein the unsaturated aliphatic hydrocarbon group at X ¹ _end and X ² _end is an allyl group. The diester compound according to any one of claims 1 to 5, wherein the aromatic ring at X ¹ _end and X ² _end is an aromatic carbocycle having 6 to 14 carbon atoms. The diester compound according to any one of claims 1 to 6, which is liquid at 25°C. The diester compound according to any one of claims 1 to 7, wherein the diester compound has a viscosity at 25°C of 300 mPa·s or less. A resin crosslinking agent containing a diester compound represented by the following formula (X).

(During the ceremony,
X _core represents a divalent aliphatic group,
X ¹ _end and X ² _end each independently represent an aromatic ring that may have a substituent.) The resin crosslinking agent according to claim 9, wherein the diester compound is the diester compound according to any one of claims 1 to 8. A resin composition comprising a diester compound (X) and a crosslinkable resin (Y),
A resin composition in which the diester compound (X) is represented by the following formula (X).

(During the ceremony,
X _core represents a divalent aliphatic group,
X ¹ _end and X ² _end each independently represent an aromatic ring that may have a substituent.) The resin composition according to claim 11, wherein the diester compound (X) is a diester compound according to any one of claims 1 to 8. The resin composition according to claim 11 or 12, wherein the crosslinkable resin (Y) is at least one selected from the group consisting of thermosetting resins and radical polymerizable resins. The resin composition according to any one of claims 11 to 13, further comprising an inorganic filler. The resin composition according to any one of claims 11 to 14, further comprising an organic solvent. The resin composition according to any one of claims 11 to 15, which is for sealing semiconductors. The resin composition according to any one of claims 11 to 15, which is for an insulating layer of a printed wiring board. A resin sheet comprising a support and a layer of the resin composition according to any one of claims 11 to 17 provided on the support. A prepreg formed by impregnating a sheet-like fiber base material with the resin composition according to any one of claims 11 to 17. A cured product of the resin composition according to any one of claims 11 to 17. A semiconductor chip package comprising a sealing layer made of a cured product of the resin composition according to any one of claims 11 to 16. The semiconductor chip package according to claim 21, which is a fan-out type package. A printed wiring board comprising an insulating layer made of a cured product of the resin composition according to any one of claims 11 to 15 and 17. A semiconductor device comprising the semiconductor chip package according to claim 21 or 22 or the printed wiring board according to claim 23.