TW202302515A - Diester compound - Google Patents

Abstract

Provided is a low-viscosity diester compound that is capable of, when combined with a crosslinkable resin, providing a resin composition exhibiting high flowability. This diester compound is represented by formula (X). (In the formula: Xcore represents a divalent aliphatic group; and X1 end and X2 end independently represent an optionally substituted aromatic ring, provided that X1 end and/or X2 end represent an aromatic ring having, as a substituent, at least one selected from among an unsaturated aliphatic hydrocarbon group, a halogen atom, an alkyl group and an aryl group.).

Description

Diester compound

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

Resin compositions containing cross-linkable resins such as epoxy resins and their cross-linking agents (curing agents) are widely used as semiconductor packaging or Electronic component materials such as printed wiring boards.

On the other hand, in the high-speed communication of the 5th generation mobile communication system (5G), the transmission loss when operating in a high-frequency environment becomes a problem. Therefore, insulating materials with dielectric properties (low dielectric coefficient, low dielectric dissipation factor) are required. Moreover, along with the further miniaturization, high integration and multi-functionalization of electronic equipment, the reduction in diameter, narrower pitch and narrower gap of bumps utilizing multi-pins has progressed. As a result, the flow path of the sealing material during sealing and molding becomes more complicated, better fluidity is required for semiconductor sealing materials, and lower viscosity is also required for the crosslinking agent used.

As a resin material excellent in dielectric properties, for example, Patent Document 1 discloses an active ester resin that is a reaction product of an aromatic diacid chloride and an aromatic hydroxy compound as a crosslinking agent for an epoxy resin. [Prior Art Literature] [Patent Document]

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

[Problem to be solved by the invention]

The active ester resin described in Patent Document 1 has excellent dielectric properties compared with conventional phenolic cross-linking agents, but there is still room for improvement in terms of lowering the viscosity. The resin composition containing this active ester resin and a cross-linking resin The fluidity of the material has not yet reached a satisfactory level.

Also, based on the viewpoint of obtaining a cured product with low dielectric dissipation factor, the viewpoint of improving heat resistance and moisture resistance after sealing and molding, and the viewpoint of realizing low warpage when sealing and molding a large area such as wafer level packaging (WLP) , From the point of view of achieving good heat dissipation in high-heat-generating devices such as power semiconductors, there are cases where a resin composition with a high content of inorganic filler is used, but in this case, fluidity at the molding temperature tends to deteriorate, There are problems of flow marks and unfilled parts.

The object of the present invention is to provide a low-viscosity diester compound capable of obtaining a resin composition exhibiting excellent fluidity in combination with a crosslinkable resin. [Means to solve the problem]

In the past, when using an ester compound as a crosslinking agent for a crosslinkable resin, in order to express crosslinking characteristics, it is considered that the ester compound is limited to a structure having an aromatic carbon-ester bond-aromatic carbon as described in Patent Document 1. Those with ester bonds. However, as a result of extensive research conducted by the present inventors, it was found that even in the structure of aliphatic carbon-ester bond-aromatic carbon, the ester bond having the structure of aliphatic carbon-C(=O)-O-aromatic carbon part, exhibiting cross-linking properties. In the process of examining the diester compound having the aliphatic carbon-C(=O)-O-aromatic carbon structure, it was found that the above-mentioned problems can be solved by the diester compound having the following structure, and thus the present invention was completed.

(式中， X _core表示2價脂肪族基， X ¹ _end及X ² _end分別獨立表示可具有取代基之芳香環，且X ¹ _end及X ² _end之至少一者為具有選自不飽和脂肪族烴基、鹵原子、烷基及芳基之1種以上作為取代基之芳香環)。 [2] 如[1]之二酯化合物，其中X _core中，2價脂肪族基之碳原子數為6以上。 [3] 如[1]或[2]之二酯化合物，其中X _core中，2價脂肪族基為伸烷基。 [4] 如[1]至[3]中任一項之二酯化合物，其中X ¹ _end及X ² _end之兩者為具有不飽和脂肪族烴基作為取代基之芳香環。 [5] 如[1]至[4]中任一項之二酯化合物，其中X ¹ _end及X ² _end中，不飽和脂肪族烴基為烯丙基。 [6] 如[1]至[5]中任一項之二酯化合物，其中X ¹ _end及X ² _end中，芳香環為碳原子數6~14之芳香族碳環。 [7] 如[1]至[6]中任一項之二酯化合物，其於25℃下為液狀。 [8] 如[1]至[7]中任一項之二酯化合物，其於25℃下之黏度為300mPa·s以下。 [9] 一種樹脂交聯劑，其包含以下述式(X)表示之二酯化合物，

(式中， X _core表示2價脂肪族基， X ¹ _end及X ² _end分別獨立表示可具有取代基之芳香環)。 [10] 如[9]之樹脂交聯劑，其中二酯化合物係如[1]至[8]中任一項之二酯化合物。 [11] 一種樹脂組成物，其係包含二酯化合物(X)與交聯性樹脂(Y)之樹脂組成物，二酯化合物(X)係以下述式(X)表示，

(式中， X _core表示2價脂肪族基， X ¹ _end及X ² _end分別獨立表示可具有取代基之芳香環)。 [12] 如[11]之樹脂組成物，其中二酯化合物(X)係如[1]至[8]中任一項之二酯化合物。 [13] 如[11]或[12]之樹脂組成物，其中交聯性樹脂(Y)係選自由熱硬化性樹脂及自由基聚合性樹脂所成之群之1種以上。 [14] 如[11]至[13]中任一項之樹脂組成物，其中進而包含無機填充材。 [15] 如[11]至[14]中任一項之樹脂組成物，其中進而包含有機溶劑。 [16] 如[11]至[15]中任一項之樹脂組成物，其係半導體密封用。 [17] 如[11]至[15]中任一項之樹脂組成物，其係印刷配線板之絕緣層用。 [18] 一種樹脂薄片，其係包含支撐體與設於該支撐體上之如[11]至[17]中任一項之樹脂組成物之層。 [19] 一種預浸片，其係於薄片狀纖維基材中含浸如[11]至[17]中任一項之樹脂組成物。 [20] 一種如[11]至[17]中任一項之樹脂組成物之硬化物。 [21] 一種半導體晶片封裝，其係包含由如[11]至[16]中任一項之樹脂組成物之硬化物而成之密封層。 [22] 如[21]之半導體晶片封裝，其係扇出(Fan-Out)型封裝。 [23] 一種印刷配線板，其係包含由如[11]~[15]、[17]中任一項之樹脂組成物之硬化物而成之絕緣層。 [24] 一種半導體裝置，其係包含如[21]或[22]之半導體晶片封裝或如[23]之印刷配線板。 [發明效果] That is, the present invention includes the following. [1] A diester compound represented by the following formula (X),

(wherein, X _core represents a divalent aliphatic group, X ¹ _end and X ² _end each independently represent an aromatic ring that may have substituents, and at least one of X ¹ _end and X ² _end is a group selected from unsaturated aliphatic Aromatic rings with one or more of aromatic hydrocarbon groups, halogen atoms, alkyl groups, and aryl groups as substituents). [2] The diester compound according to [1], wherein the number of carbon atoms in the divalent aliphatic group in X _core is 6 or more. [3] The diester compound according to [1] or [2], wherein in X _core , the divalent aliphatic group is an alkylene group. [4] The diester compound according to any one of [1] to [3], wherein both of X ¹ _end and X ² _end are aromatic rings having unsaturated aliphatic hydrocarbon groups as substituents. [5] The diester compound according to any one of [1] to [4], wherein in X ¹ _end and X ² _end , the unsaturated aliphatic hydrocarbon group is an allyl group. [6] The diester compound according to any one of [1] to [5], wherein in X ¹ _end and X ² _end , the aromatic ring is an aromatic carbocyclic ring 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], which has a viscosity at 25°C of 300 mPa·s or less. [9] A resin crosslinking agent comprising a diester compound represented by the following formula (X),

(In the formula, X _core represents a divalent aliphatic group, and X ¹ _end and X ² _end each independently represent an aromatic ring which 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), wherein the diester compound (X) is represented by the following formula (X):

(In the formula, X _core represents a divalent aliphatic group, and X ¹ _end and X ² _end each independently represent an aromatic ring which 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 used for semiconductor sealing. [17] The resin composition according to any one of [11] to [15], which is used 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 impregnated with the resin composition according to any one of [11] to [17] in a sheet-shaped fibrous base material. [20] A cured product of the resin composition according to any one of [11] to [17]. [21] A semiconductor chip package comprising a sealing layer made of a hardened resin composition according to any one of [11] to [16]. [22] The semiconductor chip package as in [21], which is a fan-out (Fan-Out) package. [23] A printed wiring board comprising an insulating layer made of a hardened resin composition according to any one of [11] to [15] and [17]. [24] A semiconductor device comprising the semiconductor chip package of [21] or [22] or the printed wiring board of [23]. [Invention effect]

According to the present invention, it is possible to provide a low-viscosity diester compound for obtaining a resin composition exhibiting excellent fluidity in combination with a crosslinkable resin.

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

＜Explanation of terms＞

In this specification, the term "may have a substituent" in relation to a compound or group means the case where the hydrogen atoms of the compound or group are not substituted by a substituent and the case where a part or all of the hydrogen atoms of the compound or group are substituted by a substituent of both.

In this specification, the term "substituent" means a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkanolyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cycloalkane group, unless otherwise specified. Oxygen, aryl, aryloxy, arylalkyl, arylalkoxy, monovalent heterocyclic group, alkylene, amino, silyl, acyl, acyloxy, carboxyl, sulfo, cyano group, nitro group, hydroxyl group, mercapto group and oxo group. Aliphatic hydrocarbon groups with unsaturated bonds such as alkenyl, alkynyl, alkanopolyenyl, and cycloalkenyl are collectively referred to as "unsaturated aliphatic hydrocarbon groups".

The halogen atom used as a substituent includes, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The alkyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-20, more preferably 1-14, more preferably 1-12, still more preferably 1-6, particularly preferably 1-3. As the alkyl group, for example, methyl, ethyl, propyl, isopropyl, butyl, second butyl, isobutyl, third butyl, pentyl, hexyl, heptyl, octyl, nonyl base and decyl.

The alkenyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkenyl group is preferably 2-20, more preferably 2-14, more preferably 2-12, still more preferably 2-6, particularly preferably 2 or 3. As the alkenyl group, for example, vinyl, allyl, 1-propenyl, butenyl, second butenyl, isobutenyl, third butenyl, pentenyl, hexenyl, heptenyl , octenyl, nonenyl and decenyl.

The alkynyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkynyl group is preferably 2-20, more preferably 2-14, more preferably 2-12, still more preferably 2-6, particularly preferably 2 or 3. Examples of the alkynyl group include ethynyl, propynyl, butynyl, second butynyl, isobutynyl, third butynyl, pentynyl, hexynyl, heptynyl, octynyl, etc. base, nonynyl and decynyl.

The alkyl polyenyl group used as a substituent may be either linear or branched, and the number of double bonds is preferably 2-10, more preferably 2-6, more preferably 2-4, and even more preferably for 2. The number of carbon atoms in the alkyl polyenyl group is preferably 3-20, more preferably 3-14, more preferably 3-12, and still more preferably 3-6.

The number of carbon atoms of the cycloalkyl group used as a substituent is preferably 3-20, more preferably 3-12, and still more preferably 3-6. As this cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group etc. are mentioned, for example.

The number of carbon atoms of the cycloalkenyl group used as a substituent is preferably 3-20, more preferably 3-12, and still more preferably 3-6. As this cycloalkenyl group, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group etc. are mentioned, for example.

The alkoxy group used as a substituent may be linear or branched. The number of carbon atoms in the alkoxy group is preferably 1-20, more preferably 1-12, and still more preferably 1-6. As the alkoxy group, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, second butoxy, isobutoxy, tertiary butoxy, pentyloxy , Hexyloxy, Heptyloxy, Octyloxy, Nonyloxy and Decyloxy.

The number of carbon atoms of the cycloalkoxy group used as a substituent is preferably 3-20, more preferably 3-12, still more preferably 3-6. Examples of the cycloalkoxy group include cyclopropoxy, cyclobutoxy, cyclopentyloxy and cyclohexyloxy.

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

The number of carbon atoms of the aryloxy group used as a substituent is preferably 6-24, more preferably 6-18, still more preferably 6-14, still more preferably 6-10. The aryloxy group used as a substituent includes, for example, phenoxy, 1-naphthyloxy and 2-naphthyloxy.

The number of carbon atoms of the arylalkyl group used as a substituent is preferably 7-25, more preferably 7-19, still more preferably 7-15, still more preferably 7-11. Examples of the arylalkyl group include, for example, phenyl-C ₁ -C ₁₂ alkyl, naphthyl-C ₁ -C ₁₂ alkyl and anthracenyl-C ₁ -C ₁₂ alkyl.

The number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7-25, more preferably 7-19, still more preferably 7-15, still more preferably 7-11. Examples of the arylalkoxy group include phenyl-C ₁ -C ₁₂ alkoxy and naphthyl-C ₁ -C ₁₂ alkoxy.

The monovalent heterocyclic group used as a substituent means a group obtained by removing one hydrogen atom from a heterocyclic ring of a heterocyclic compound. The number of carbon atoms in the monovalent heterocyclic group is preferably 3-21, more preferably 3-15, and still more preferably 3-9. The monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl). Examples of the monovalent heterocycle include thienyl, pyrrolyl, furanyl, fyryl, pyridyl, pyrazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolidinyl, Piperidinyl, quinolinyl and isoquinolinyl.

The alkylene group used as a substituent means a group obtained by removing two hydrogen atoms from the same carbon atom of an alkane. The number of carbon atoms in the alkylene group is preferably 1-20, more preferably 1-14, more preferably 1-12, still more preferably 1-6, particularly preferably 1-3. Examples of the alkylene group include methylene, ethylene, propylene, isopropylene, butylene, second-butylene, isobutylene, tert-butylene, pentylene, Hexylene, heptylene, octylene, nonylene and decylene.

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

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

The above-mentioned substituent may further have a substituent (hereinafter may be referred to as a "secondary substituent"). As the secondary substituent, unless otherwise stated, the same ones as those described above can be used.

In the present specification, the term "aliphatic group" refers to a group except one or more hydrogen atoms bonded to the aliphatic carbon of the aliphatic compound. Specifically, the so-called monovalent aliphatic group refers to the group that removes one hydrogen atom bonded to the aliphatic carbon of the aliphatic compound, and the so-called bivalent aliphatic group refers to the group that removes two aliphatic carbon bonds with the aliphatic compound. The basis of the hydrogen atom of the knot. Examples of the divalent aliphatic group include an optionally substituted alkylene group, an optionally substituted cycloalkylene group, an optionally substituted alkenylene group, and an optionally substituted cycloalkene group. In the present specification, unless otherwise specified, the number of carbon atoms in the aliphatic group is preferably 1 or more, more preferably 2 or more, more preferably 3 or more, 4 or more, 5 or more, or 6 or more, preferably 50 or less , more preferably 40 or less, 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 a substituent is not included in the number of carbon atoms.

In this specification, the term "aromatic ring" refers to a ring in which the number of electrons contained in the π electron system on the ring is 4p+2 (p is a natural number) and conforms to Huckel's law, including monocyclic aromatic rings, and A condensed aromatic ring in which two or more monocyclic aromatic rings are condensed. The aromatic ring may be an aromatic carbocyclic ring having only carbon atoms as ring constituting atoms, or an aromatic heterocyclic ring having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms as ring constituting 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 more preferably 6 or more, and the upper limit is preferably 24 or less, more preferably It is 18 or less or 14 or less, and more preferably 10 or less. The number of carbon atoms of a substituent is not included in the number of carbon atoms. Examples of the aromatic ring include, for example, a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an imidazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyrazine ring. Monocyclic aromatic rings such as rings; naphthalene ring, anthracene ring, phenanthrene ring, benzofuran ring, isobenzofuran ring, indole ring, isoindole ring, benzothiophene ring, benzimidazole ring, indazole ring ring, benzoxazole ring, benzisoxazole ring, benzothiazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, acridine ring, quinazoline ring, cinnoline ring, phthalazine ring A condensed aromatic ring formed by condensing two or more monocyclic aromatic rings.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments and illustrations, and can be implemented with arbitrary changes within the scope not departing from the scope of the present invention and its equivalent scope.

[Diester compound] The characteristics of the diester compound of the present invention include: A core unit composed of divalent aliphatic groups, and the first and second capping units bonded to the core unit via an ester bond, The first and second capping units are each independently an aromatic ring which may have a substituent.

In the diester compound of the present invention, the core unit and the capping unit are bonded via an ester bond (-C(=O)-O-). Specifically, the core unit and the end cap unit are bonded via an ester bond such that the carbonyl group (-C(=O)-) is bonded to the core unit and the oxygen group (-O-) is bonded to the end cap unit. Accordingly, the diester compound of the present invention has a structure of aliphatic carbon-C(=O)-O-aromatic carbon as an ester bond. The present invention, as described later, is based on the discovery that the ester bond portion having the aliphatic carbon-C(=O)-O-aromatic carbon structure exhibits crosslinking properties, and it is the first discovery of a finding that could not be predicted by the prior art.

Therefore, when the core unit is X _core and the first and second end capping 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).

(式中， X _core表示2價脂肪族基， X ¹ _end及X ² _end分別獨立表示可具有取代基之芳香環)。

(In the formula, X _core represents a divalent aliphatic group, and X ¹ _end and X ² _end each independently represent an aromatic ring which may have a substituent).

-Core unit (X _core )- The core unit X _core is composed of divalent aliphatic groups.

By having a core unit composed of divalent aliphatic groups, the diester compound of the present invention can exhibit low-viscosity properties. Furthermore, when combined with a cross-linkable resin, a cured product rich in toughness and flexibility can be obtained.

When using an ester compound as a crosslinking agent for a crosslinkable resin, in order to exhibit crosslinking properties, an active ester bond should be formed, and the ester bond must have an aromatic carbon-C(=O)-O-aromatic carbon structure. On the other hand, the diester compound of the present invention including a core unit composed of a divalent aliphatic group has a structure of aliphatic carbon-C(=O)-O-aromatic carbon. The inventors of the present invention found that the diester compound having the specific ester bond structure exhibits good low-viscosity properties and functions as a crosslinking agent for crosslinkable resins.

In the core unit X _core , the number of carbon atoms of the divalent aliphatic group is preferably 4 or more, more preferably 6 or more or 8 or more, from the viewpoint of realizing a lower viscosity diester compound. Therefore, in a preferred embodiment, in the core unit X _core , the number of carbon atoms in 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 can be appropriately determined within the aforementioned range. In addition, the number of carbon atoms of a substituent is not included in the number of carbon atoms.

In the core unit X _core , the divalent aliphatic group is preferably an alkylene group which may have a substituent or an alkenylene group which may have a substituent, particularly preferably An alkylene group which may have a substituent. The alkylene group in the core unit may be linear or branched. Therefore, in a preferred embodiment, in the core unit X _core , the divalent aliphatic group is an alkylene group.

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

-First and second end capping units (X ¹ _end and X ² _end )—The first and second end capping units X ¹ _end and X ² _end are each independently an aromatic ring which may have a substituent.

By having an aromatic ring which may have a substituent as the first and second end-capping units, the diester compound of the present invention is formulated in a resin composition as a crosslinking agent for a crosslinkable resin.

Among the end-capping units X ¹ _end and X ² _end , the aromatic ring is preferably an aromatic carbocyclic ring from the viewpoint of better enjoying the effect of the present invention. The number of carbon atoms of the aromatic carbocyclic ring is preferably 6-14, more preferably 6-10. Therefore, in a preferred embodiment, in the capping unit, the aromatic ring is an aromatic carbocyclic ring having 6 to 14 carbon atoms.

The substituents that the aromatic ring in the capping unit may have are as described above. Among them, from the viewpoint of realizing a lower-viscosity diester compound, it is preferably one or more selected from unsaturated aliphatic hydrocarbon groups, halogen atoms, alkyl groups, and aryl groups, and more preferably selected from unsaturated aliphatic hydrocarbon groups with 2 to 20 carbon atoms. One or more of saturated aliphatic hydrocarbon groups, fluorine atoms, alkyl groups with 1 to 6 carbon atoms, and aryl groups with 6 to 10 carbon atoms. When the aromatic ring in the end capping unit has a substituent, only one of the first and second end capping units X ¹ _end and X ² _end may have a substituent, or both may have a substituent. In one embodiment, at least one of the first and second end-capping units X ¹ _end and X ² _end is an aromatic ring having a substituent. In a preferred embodiment, the first and second end-capping units X ¹ _end and at least one of X ² _end is an aromatic ring having one or more substituents selected from unsaturated aliphatic hydrocarbon groups, halogen atoms, alkyl groups, and aryl groups. When X ¹ _end and X ² _end are aromatic rings without substituents, they tend to be highly crystalline and difficult to liquefy at room temperature. In addition, when X ¹ _end and X ² _end are aromatic rings having substituents, they have weak crystallinity, are easily liquefied at room temperature, and have excellent fluidity and handleability.

Among them, when at least one of the first and second end-capping units X ¹ _end and X ² _end is an aromatic ring having an unsaturated aliphatic hydrocarbon group as a substituent, it is preferable to realize a particularly low-viscosity diester compound. Therefore, in a preferred embodiment, at least one of the first and second end capping 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 capping units are aromatic rings having unsaturated aliphatic hydrocarbon groups as substituents, particularly low viscosity can be achieved, such as diester compounds that are liquid at normal temperature (25°C). Here, in this specification, the term "liquid at room temperature (25° C.)" for the diester compound means that the viscosity of the diester compound at 25° C. is 3,000 mPa·s or less. Therefore, in a preferred embodiment, both of the first and second end capping units X ¹ _end and X ² _end are aromatic rings having unsaturated aliphatic hydrocarbon groups as substituents.

Based on the viewpoint of realizing a lower viscosity diester compound, the number of carbon atoms of the unsaturated aliphatic hydrocarbon group that can be used as a substituent in the aromatic ring in the capping unit is preferably 2-20, more preferably 2-14 , 2~12, 2~10 or 2~6. From the viewpoint of realizing a lower viscosity diester compound, the unsaturated aliphatic hydrocarbon group is preferably an alkenyl or alkynyl group, more preferably an alkenyl group. Among them, the unsaturated aliphatic hydrocarbon group that may be contained as a substituent in the aromatic ring in the capping unit is preferably an alkenyl group with 2 to 10 carbon atoms, more preferably an alkenyl group with 2 to 6 carbon atoms, and more preferably Allyl is preferred. Therefore, in a preferred embodiment, in the end-capping units X ¹ _end and X ² _end , the unsaturated aliphatic hydrocarbon group that may have as a substituent in the aromatic ring is an allyl group.

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

(式中， X _core表示由2價脂肪族基所成之芯單元， 環Ar分別獨立表示芳香環， R ¹分別獨立表示不飽和脂肪族烴基， R ²分別獨立表示取代基， n11及n12分別獨立表示0~2之整數， m11及m12，於將環Ar之可取代氫原子數設為p個時，表示滿足0≦m11≦(p-n11)及0≦m12≦(p-n12)之整數)。

(In the formula, X _core represents a core unit composed of a divalent aliphatic group, the ring Ar independently represents an aromatic ring, R ¹ represents an unsaturated aliphatic hydrocarbon group independently, R ² represents a substituent independently, n11 and n12 respectively Integers independently representing 0~2, m11 and m12, when the number of substitutable hydrogen atoms in the ring Ar is set as p, it means that 0≦m11≦(p-n11) and 0≦m12≦(p-n12) are satisfied integer).

In formula (X1), X _core represents a core unit composed of a divalent aliphatic group. About this core unit, including the preferable example, it is as above-mentioned. In a preferred embodiment, X _core is a divalent aliphatic group having 6 or more carbon atoms, more preferably an alkylene group having 6 or more carbon atoms which may have a substituent. Preferable examples of substituents are also as described above.

In the formula (X1), the rings Ar each independently represent an aromatic ring. The aromatic rings correspond to the aromatic rings in the first and second capping units, including their preferred examples, as described above. In a preferred embodiment, the rings Ar are each independently an aromatic carbocyclic ring having 6 to 14 carbon atoms, more preferably a benzene ring or a naphthalene ring.

In formula (X1), R ¹ each independently represent an unsaturated aliphatic hydrocarbon group. R ¹ corresponds to an unsaturated aliphatic hydrocarbon group that may be present as a substituent in the aromatic ring in the first and second end-capping units, and is as described above including its preferred examples. In a preferred embodiment, ^R are independently unsaturated aliphatic hydrocarbon groups with 2 to 20 carbon atoms, more preferably alkenyl groups with 2 to 20 carbon atoms (preferably 2 to 10 or 2 to 6), or An alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 or 2 to 6), more preferably an allyl group.

In formula (X1), R ² each independently represent a substituent. R ² corresponds to a substituent that may be present in the aromatic ring in the first and second capping units, including preferred examples thereof, as described above. In a preferred embodiment, R ^are independently selected from halogen atoms, alkyl groups and aryl groups, more preferably selected from fluorine atoms, alkyl groups with 1-6 carbon atoms, and aryl groups with 6-10 carbon atoms.

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

When n11 or n12 is 1 or more, the bonding position of ^R1 to the ring Ar is not particularly limited, but based on the viewpoint of realizing a lower viscosity diester compound, the relationship with the bonding position of the oxygen group of the ester bond is preferably Ortho or meta, more preferably ortho.

In formula (X1), m11 and m12 represent integers satisfying 0≦m11≦(p-n11) and 0≦m12≦(p-n12), when the number of substitutable hydrogen atoms in ring Ar is p. The number p of substitutable hydrogen atoms in the ring Ar does not include the bonding site of the oxy group bonded to the ester. For example, when the ring Ar is a benzene ring, the number p of hydrogen atoms that can be substituted is 5, and when the ring Ar is a naphthalene ring, the number p of hydrogen atoms that can be substituted is 7.

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

(式中， X _core、R ¹及R ²如上述， n21及n22分別獨立表示0~2之整數， m21及m22表示滿足0≦m21≦(5-n21)及0≦m22≦(5-n22)之整數)。

(In the formula, X _core , R ¹ and R ² are as above, n21 and n22 independently represent integers from 0 to 2, m21 and m22 indicate that 0≦m21≦(5-n21) and 0≦m22≦(5-n22 ) is an integer).

(式中， X _core、R ¹及R ²如上述， n31及n32分別獨立表示0~2之整數， m31及m32表示滿足0≦m31≦(7-n31)及0≦m32≦(7-n32)之整數)。

(In the formula, X _core , R ¹ and R ² are as above, n31 and n32 independently represent integers from 0 to 2, m31 and m32 indicate that 0≦m31≦(7-n31) and 0≦m32≦(7-n32 ) is an integer).

No matter which one of formula (X2) and formula (X3), X _core , R ¹ and R ² are as above, and their preferred examples are also as described above.

In the formula (X2), n21 and n22 each independently represent an integer of 0 to 2. At least one of n21 and n22 is preferably 1 or more from the viewpoint of realizing a lower-viscosity diester compound. In a preferred embodiment, n21 and n22 are independently 1 or 2, more preferably both n21 and n22 are 1.

When n21 or n22 is 1 or more, the bonding position of ^R1 relative to the benzene ring is not particularly limited. From the viewpoint of realizing a diester compound with lower viscosity, the relationship with the bonding position of the oxygen group of the ester bond is preferably ortho Position or meta position, more preferably ortho position.

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

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

When n31 or n32 is 1 or more, ^R1 is not particularly limited to the bonding position of the naphthalene ring, but from the viewpoint of realizing a diester compound with lower viscosity, the relationship with the bonding position of the oxygen group of the ester bond is preferably adjacent Position or meta position, more preferably ortho position.

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

In a preferred embodiment, in formula (X2), i) X _core is an alkylene group having 6 or more carbon atoms that may have a substituent, ii) at least one of (a) n21 and n22 is 1 or 2, ^R1 is independently an alkenyl group with 2 to 20 carbon atoms or an alkynyl group with 2 to 20 carbon atoms, m21 and m22 are each independently an integer of 0 to 2, and ^R2 are independently selected from halogen atoms, alkyl groups and Aryl, or (b) n21 and n22 are 0, m21 and m22 are independently integers of 0 to 5, and ^R2 are independently selected from halogen atoms, alkyl groups and aryl groups.

In a more preferable embodiment, in formula (X2), i) X _core is an alkyl group having 6 or more carbon atoms which may have one or more substituents selected from halogen atoms, alkyl groups and alkenyl groups, ii) (a ) at least one of n21 and n22 is 1 or 2, ^R1 is independently an alkenyl group with 2 to 10 carbon atoms, m21 and m22 are each independently an integer of 0 to 2, and ^R2 is independently selected from a halogen atom, Alkyl and aryl, or (b) n21 and n22 are 0, m21 and m22 are respectively independently an integer of 0 to 5, and ^R2 is independently selected from a halogen atom, an alkyl group and an aryl group.

In a preferred embodiment, in formula (X3), i) X _core is an alkylene group having 6 or more carbon atoms which may have a substituent, ii) at least one of (a) n31 and n32 is 1 or 2, ^R1 is independently an alkenyl group with 2~20 carbon atoms or an alkenyl group with 2~20 carbon atoms, m31 and m32 are each independently an integer of 0~2, and ^R2 are independently selected from halogen atoms, alkyl groups and Aryl, or (b) n31 and n32 are 0, m31 and m32 are independently integers of 0 to 7, and ^R2 are independently selected from halogen atoms, alkyl groups and aryl groups.

In a more preferred embodiment, in formula (X3), i) X _core is an alkylene group having 6 or more carbon atoms which may have one or more substituents selected from halogen atoms, alkyl groups and alkenyl groups, ii) ( a) At least one of n31 and n32 is 1 or 2, ^R1 is independently an alkenyl group with 2 to 10 carbon atoms, m31 and m32 are each independently an integer of 0 to 2, and ^R2 is independently selected from a halogen atom , an alkyl group and an aryl group, or (b) n31 and n32 are 0, m31 and m32 are independently an integer of 0 to 7, and ^R2 is independently 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) is preferably at least 150 g/eq., more preferably at least 160 g/eq., more preferably at least 180 g/eq., and at least 200 g/eq. . The upper limit of the equivalent of the oxycarbonyl group is, for example, 1000 g/eq. or less, 750 g/eq. or less, 700 g/eq. or less, 600 g/eq. or less, or 500 g/eq.

The molecular weight of the diester compound of the present invention (number average molecular weight Mn when having a distribution) is preferably 2,000 or less, more preferably 1,500 or less, from the viewpoint of blending in the resin composition as a cross-linking agent for a cross-linkable resin. More preferably, it is 1400 or less, 1200 or less, or 1000 or less. The lower limit of this molecular weight is not specifically limited, For example, it may be 300 or more, 320 or more. The molecular weight can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC).

One example is shown below with respect to the synthesis|combination procedure of the diester compound of this invention.

In one embodiment, the diester compound of the present invention is obtained by using (A) A divalent aliphatic carboxylic acid compound or a divalent aliphatic carboxylic acid halide compound and (B) Monovalent aromatic hydroxy compound which may have a substituent For condensation reaction derived.

-(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).

(式中，X _core如上述，Z表示羥基或鹵原子)。

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

As the (A) component, any divalent aliphatic carboxylic acid (halide) compound may be used depending on the intended core unit X _core . Preferred examples of X _core are as above. For example, when the target core unit X _core is a straight-chain alkylene group with 6 carbon atoms, suberic acid (chloride) can be used, and when it is a straight-chain alkylene group with 8 carbon atoms, only decane can be used. Acids (chlorides) are sufficient.

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

(式中， 環Ar、R ¹及R ²如上述， n表示0~2之整數， m於將環Ar之可取代氫原子數設為p個時，表示滿足0≦m≦(p-n)的整數)。

(In the formula, ring Ar, R ¹ and R ² are as above, n represents an integer of 0 to 2, and m, when the number of substitutable hydrogen atoms in ring Ar is set as p, represents a condition that satisfies 0≦m≦(pn) integer).

As the (B) component, any aromatic monoalcohol may be used depending on the intended terminal unit. Ring Ar, R ¹ and R ² are as described above. For example, as the aromatic monoalcohol, when the intended end-capping unit is a benzene ring having an alkenyl group having 2 to 6 carbon atoms as a substituent, n is ¹ and R is 2 to 6 carbon atoms. As the alkenyl phenol compound, for example, vinylphenol, allylphenol, 1-propenylphenol, butenylphenol, pentenylphenol, hexenylphenol and the like may be used. And, when the intended terminal unit is a benzene ring having a fluorine atom as a substituent, m is 1 to 5 and ^R2 is a phenolic compound of a fluorine atom, for example, as long as pentafluorophenol, tetrafluorophenol, trifluorophenol, etc. are used. Can.

The condensation reaction may be performed in an anhydrous system without using a solvent, or may be performed in an organic solvent system using an organic solvent. As the organic solvent used in the condensation reaction, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and other ketone solvents; ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol Acetate-based solvents such as monomethyl ether acetate and carbitol acetate; carbitol-based solvents such as cellosolve and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; N , Amide-based solvents such as N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc. An organic solvent may be used individually by 1 type, and may use it in combination of 2 or more types.

In the condensation reaction, a base can be used. As the base, for example, alkali metal hydroxides such as sodium hydroxide (caustic soda) or potassium hydroxide; tertiary grades of triethylamine, pyridine, N,N-dimethyl-4-aminopyridine (DMAP), etc. Amines etc. The base may be used alone or in combination of two or more.

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

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

The diester compound can be purified after the condensation reaction. For example, after the condensation reaction, in order to remove by-product salts and excess starting materials from the system, purification steps such as washing with water or microfiltration may also be performed. Specifically, after the condensation reaction, the amount of water required to dissolve the by-produced salt was added, the liquid separation was carried out at rest, and the aqueous layer was discarded. Furthermore, acid addition, neutralization, and water washing were repeated as needed. Then, after purifying impurities are removed by fine filtration of a chemical agent or an azeotropic dehydration step, the diester compound can be obtained by distilling off an organic solvent as necessary. It can also be used as a solvent of 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 vibrating viscometer as described in the section (Conditions for measuring viscosity during heating), the viscosity of the diester compound of the present invention at 75° C. is preferably 1000 mPa·s or less, more preferably 500 mPa·s or less , and 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.

A preferred embodiment in which at least one (preferably both) of the first and second capping units is an aromatic ring having an unsaturated aliphatic hydrocarbon group as a substituent can exhibit particularly low viscosity. In this preferred embodiment, the diester compound of the present invention is liquid at normal 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 1500 mPa·s or less, more preferably less than 1000 mPa·s, less than 800 mPa·s, less than 600 mPa·s, less than 500 mPa·s, or less than 400 mPa·s. In a particularly preferred embodiment in which both the first and second capping units are aromatic rings having unsaturated aliphatic hydrocarbon groups as substituents, the diester compound of the present invention can exhibit lower viscosity. The viscosity at 25°C is, for example, 300mPa·s or less, 250mPa·s or less, 200mPa·s or less, 150mPa·s or less or can be reduced to 100mPa·s or less. Therefore, in a preferred embodiment, the diester compound of the present invention has a viscosity at 25° C. of 300 mPa·s or less.

The diester compound of the present invention, when combined with a cross-linking resin, can obtain the advantages of an ester compound of a hardened product exhibiting excellent dielectric properties, and is low in viscosity, and can realize flow when combined with a cross-linking resin Since it is a resin composition with good properties, it can suppress the occurrence of flow marks and unfilled parts during molding such as sealing molding. In addition, the diester compound of the present invention can be combined with a cross-linkable resin to obtain a cured product rich in toughness and flexibility. In addition, even if the content of the inorganic filler is high, a resin composition with good fluidity at the molding temperature can be obtained, which can achieve excellent heat resistance and moisture resistance, lower dielectric loss factor, low warpage, and heat dissipation Also a good hardener. Therefore, in a preferred 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 the resin composition.

The feature of the resin composition of the present invention is to include a diester compound (X) and a crosslinkable resin (Y). ester compounds.

Preferred examples of the core unit and the first and second capping units, and details of the diester compound (X) represented by a preferred embodiment of the general formula are as described in the above-mentioned [diester compound] column.

In the resin composition of the present invention, the type of the 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), the crosslinkable resin (Y) is preferably selected from thermosetting resins from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and exhibiting good fluidity during molding. and one or more of the group consisting of radically polymerizable resins.

As the thermosetting resin and the radically polymerizable resin, known resins used when forming insulating layers of printed wiring boards and semiconductor chip packages can be used. Hereinafter, thermosetting resins and radical polymerizable resins usable as the crosslinkable resin (Y) will be described.

Examples of thermosetting resins include epoxy resins, benzocyclobutene resins, epoxy acrylate resins, urethane acrylate resins, urethane resins, cyanate resins, polyamide resins, etc. Amine resin, benzoxazine resin, unsaturated polyester resin, phenol resin, melamine resin, silicone resin, phenoxy resin, etc. The thermosetting resin may be used alone or in combination of two or more. Among them, when used in combination with the diester compound (X), the crosslinkable resin (Y) preferably includes an epoxy resin from the viewpoint of exhibiting good fluidity during molding and obtaining excellent dielectric properties after curing.

The type of the epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups in one molecule. Examples of epoxy resins include 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, tertiary Catechol-based epoxy resin, naphthol-based epoxy resin, naphthalene-based epoxy resin, naphthyl ether-based epoxy resin, glycidylamine-based epoxy resin, glycidyl ester-based epoxy resin, cresol novolak-based Epoxy resin, biphenyl type epoxy resin, phenol aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin, fennel skeleton type epoxy resin, dicyclopentadiene type epoxy resin, anthracene type epoxy resin Oxygen resin, chain aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexanedimethanol ring Oxygen resin, trimethylol type epoxy resin, halogenated epoxy resin, etc. According to the resin composition of the present invention containing the diester compound (X), regardless of the type of epoxy resin, it exhibits good fluidity during molding, and can obtain excellent dielectric properties after curing.

Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter referred to as "solid epoxy resins"). ), in the resin composition of the present invention, as the crosslinkable resin (Y), it may only contain liquid epoxy resin, may only contain solid epoxy resin, or may include liquid epoxy resin and solid epoxy resin in combination. oxygen resin. When the combination includes liquid epoxy resin and solid epoxy resin, the deployment ratio (liquid:solid) is in the range of 20:1~1:20 by mass ratio (preferably 10:1~1:10, more preferably Preferably 3:1~1:3).

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

The weight average molecular weight (Mw) of the epoxy resin is preferably 100-5,000, more preferably 250-3,000, and more preferably 400-1,500. The Mw of the epoxy resin can be measured as a polystyrene-equivalent value by the 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 in one molecule. As the radically polymerizable resin, there are, for example, those having a radically polymerizable unsaturated group selected from the group consisting of maleimide group, vinyl group, allyl group, styryl group, vinylphenyl group, acryl group, formyl group, etc. One or more resins of acryl, fumaryl and maleyl. Among them, when used in combination with the diester compound (X), the crosslinkable resin (Y) preferably contains a compound selected from the group consisting of manilimide resins, One or more of (meth)acrylic resin and styrene resin.

As long as the maleimide resin has more than one (preferably more than two) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl) in one molecule ), the type is not particularly limited. Examples of maleimide resins include "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all are Designer Manufactured by Molecules Co., Ltd.) and the like containing maleimide resins containing an aliphatic skeleton with 36 carbon atoms derived from dimer diamine lipids; those containing an indane skeleton as described in Public Technical Publication No. 2020-500211 of the Invention Association Maleimide resin; "MIR-3000-70MT" (manufactured by Nippon Kayaku Co., Ltd.), "BMI-4000" (manufactured by Daiwa Chemical Co., Ltd.), "BMI-80" (manufactured by KI Chemical Co., Ltd.) and Malay A maleimide resin with an aromatic ring skeleton directly bonded to the nitrogen atom of the imide group.

The type of the (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)acryl" is a generic term for acryl and methacryl. Examples of methacrylic resins include "A-DOG" (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Co., Ltd.), "NPDGA", "FM-400", "R- 687", "THE-330", "PET-30", "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.) and other (meth)acrylic resins.

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

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

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

Examples of inorganic fillers include silicon oxide, aluminum oxide, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum borate, titanic acid Barium, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, calcium zirconate, etc. can be selected according to the specific application. The inorganic filler may be used alone or in combination of two or more. Examples of commercially available inorganic fillers include "UFP-30" (manufactured by Denka Kagaku Kogyo Co., Ltd.); SX", "SO-C4", "SO-C2", "SO-C1", "SC-C2" (all manufactured by ADMATECHS); "SILFILL NSS-3N", "SILFILL NSS-4N", "SILFILL "NSS-5N" (manufactured by TOKUYAMA), "DAW-0525" (manufactured by DENKA), etc.

The average particle size of the inorganic filler may be determined in an appropriate range according to specific applications. For example, when forming the interlayer insulating layer of a printed wiring board or the rewiring formation layer of a semiconductor chip package, the average particle size of the inorganic filler is Preferably it is 5 μm or less, more preferably 2 μm or less, and still more preferably 1 μm or less. In addition, when forming the sealing layer of the semiconductor chip package, the average particle diameter of the inorganic filler is preferably 15 μm or less, more preferably 14 μm or less, and more preferably 12 μm or less, 10 μm or less from the viewpoint of improving fluidity during sealing molding. Or less than 8 μm. The lower limit of the average particle size is not particularly limited, as long as it is determined according to specific applications, for example, it can be 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 size of the inorganic filler can be measured by the laser diffraction-scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be prepared on a volume basis using a laser diffraction scattering particle size distribution measuring device, and the median diameter can be used as the average particle diameter for measurement. As a measurement sample, one obtained by dispersing an inorganic filler in water with ultrasonic waves can be used. As a laser diffraction-scattering type particle size distribution measuring device, LA-950 manufactured by Horiba Seisakusho Co., Ltd., etc. can be used.

Inorganic fillers are preferably amino silane coupling agents, urea silane coupling agents, epoxy silane coupling agents, mercapto silane coupling agents, vinyl silane coupling agents, styryl silane coupling agents, acrylates Silane coupling agent, isocyanate silane coupling agent, thioether silane coupling agent, organic silazane compound, titanate coupling agent and other surface treatment agents are used for surface treatment 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 can be determined according to the properties required for the resin composition, but when the non-volatile components in the resin composition are set to 100% by mass, for example It is 5 mass % or more, 10 mass % or more, Preferably it is 30 mass % or more, More preferably, it is 40 mass % or more, More preferably, it is 50 mass % or more. According to the resin composition of the present invention having the diester compound (X) as a core unit composed of a divalent aliphatic group, good fluidity during molding can be ensured, and the content of the inorganic filler can be further increased. The content of the inorganic filler in the resin composition is, for example, 60 mass % or more, 65 mass % or more, 70 mass % or more, 75 mass % or more, or as high as 80 mass % or more. Thereby, the resin composition of the present invention satisfies narrow gap filling properties, and has a particularly low dielectric dissipation factor, excellent heat resistance, moisture resistance, and low warpage, and can achieve high heat dissipation depending on the type of inorganic filler of hardened. The upper limit of the content of the inorganic filler in the resin composition is not particularly limited, for example, it may be 95% by mass or less, 90% by mass or less.

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

Examples of resin crosslinking agents other than the diester compound (X) include "TD2090", "TD2131" (manufactured by DIC Corporation), "MEH-7600", "MEH-7851", "MEH-8000H" (manufactured by Meiwa Chemical Co., Ltd. ), "NHN", "CBN", "GPH-65", "GPH-103" (Nippon Kayaku), "SN170", "SN180", "SN190", "SN475", "SN485", Phenolic hardeners such as "SN495", "SN375", "SN395" (manufactured by Nippon Steel Chemical & Materials Co., Ltd.), "LA7052", "LA7054", "LA3018", "LA1356" (manufactured by DIC Corporation); "F-a" , "P-d" (manufactured by Shikoku Chemicals Co., Ltd.), "HFB2006M" (manufactured by Showa Polymer Co., Ltd.) and other benzoxazine-based crosslinking agents; Anhydride-based cross-linking agents such as Ginaldine anhydride; cyanate-based cross-linking agents such as PT30, PT60, and BA230S75 (manufactured by Japan Lonza Co.); benzoxazine-based cross-linking agents, etc.

When the resin composition of the present invention contains a resin crosslinking agent other than the diester compound (X), the content of the resin crosslinking agent in the resin composition can be determined according to the required properties of the resin composition, but the resin composition When the non-volatile content is 100% by mass, it is preferably 40% by mass or less, more preferably 20% by mass or less, more preferably 10% by mass or less, and the lower limit may be 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or less. Mass% or more.

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

As a crosslinking accelerator, for example, organic phosphine compounds such as "TPP", "TPP-K", "TPP-S", "TPTP-S" (manufactured by Hokko Chemical Industry Co., Ltd.); "Curazole 2MZ", "2E4MZ ", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", "Cl1Z-A", "2MZ-OK", "2MA-OK", "2PHZ" (manufactured by Shikoku Chemical Industry Co., Ltd.) and other imidazole compounds ; Amine adduct compounds such as Nobacure (manufactured by Asahi Chemical Industry Co., Ltd.), Fujicure (manufactured by Fuji Chemical Industry Co., Ltd.); 1,8-diazabicyclo[5,4,0]undecene-7,4-di Amine compounds such as methylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 4-dimethylaminopyridine; cobalt, copper, zinc, iron, nickel, Manganese, tin and other organometallic complexes or organometallic salts, etc.

When the resin composition of the present invention contains a crosslinking accelerator, the content of the crosslinking accelerator in the resin composition can be determined according to the properties required for the resin composition, but the non-volatile components in the resin composition are set to 100% by mass , preferably at most 10 mass %, more preferably at most 5 mass %, and more preferably at most 1 mass %, the lower limit may be at least 0.001 mass %, at least 0.01 mass %, or at least 0.05 mass %.

The resin composition of the present invention may further contain arbitrary 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; Aldehyde resin, polyether resin, polyether resin, polyphenylene ether resin, polyether ether ketone resin, polyester resin and other thermoplastic resins; organic copper compounds, organic zinc compounds, organic cobalt compounds and other organic metal compounds; phthalocyanine blue, Phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black and other colorants; hydroquinone, catechol, pyrogallol, phenothiazine and other polymerization inhibitors; silicone-based leveling agent, acrylic acid Leveling agents such as polymer-based leveling agents; thickeners such as BENTONE and montmorillonite; silicone-based defoamers, acrylic-based defoamers, fluorine-based defoamers, vinyl resin-based defoamers, etc. UV absorbers such as benzotriazole-based UV absorbers; adhesiveness enhancers such as urea silane; triazole-based adhesion imparting agents, tetrazole-based adhesion-imparting agents, triazine-based adhesion-imparting agents, etc. Adhesion imparting agent; hindered phenol-based antioxidant and other antioxidants; diphenylethylene derivatives and other optical brighteners; fluorine-based surfactants, silicone-based surfactants and other surfactants; phosphorus-based flame retardants (such as phosphate ester compounds, phosphazene compounds, phosphonic acid compounds, red phosphorus), nitrogen-based flame retardants (such as melamine sulfate), halogen-based flame retardants, inorganic flame retardants (such as antimony trioxide), etc. Dispersants; Phosphate-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, cationic dispersants and other dispersants; borate-based stabilizers, titanate-based Stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, carboxylic anhydride-based stabilizers, etc. The content of the additive can be determined according to the required properties of 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 solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and isobutyl acetate; Pentyl ester, methyl propionate, ethyl propionate, γ-butyrolactone and other ester solvents; tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, Diphenyl ether and other ether solvents; methanol, ethanol, propanol, butanol, ethylene glycol and other alcohol solvents; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether Ether ester solvents such as esters, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohols such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate solvents; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, diethylene glycol monobutyl ether (butyl carbitol); Amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc.; amide-based solvents such as dimethylsulfide; acetonitrile nitrile solvents such as propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and trimethylbenzene Department of solvents, etc. An organic solvent may be used individually by 1 type, and may use it in combination of 2 or more types.

When the resin composition of the present invention includes an organic solvent, the content of the organic solvent in the resin composition can be determined according to the required properties of the resin composition, but when the total components in the resin composition are set to 100% by mass, for example, it can be 60% by mass. 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, an organic solvent can be added as a diluent to prepare the resin composition. When the resin composition is used to form an insulating layer of a semiconductor chip package or a printed wiring board, the following disadvantages occur: voids are generated in the film forming step or the sealing molding step, a large volume of waste equipment is required due to organic solvents, and the resulting insulating layer Residual organic solvents, etc. On the other hand, according to the resin composition of the present invention containing the diester compound (X) having a core unit composed of a divalent aliphatic group, even when the organic solvent content is reduced or the organic solvent is not contained, the resin composition is uniform during molding. It is preferable because it can exhibit good fluidity. The organic solvent content in the resin composition of the present invention may be, for example, less than 10% by mass, 8% by mass or less, 6% by mass or less, 5% by mass or less, 4% by mass or less, 2% by mass or less, 1% by mass or less, or It may be as low as 0.5 mass % or less, and may be 0 mass % (solvent-free system).

The resin composition of the present invention can be obtained by mixing the necessary components of the above-mentioned components appropriately, and if necessary, by mixing chain means such as three-rollers, ball mills, bead mills, sand mills, etc., or super mixers, planetary mixers, etc. Stirring means to be blended or mixed to prepare.

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

In one embodiment, the cured product of the resin composition of the present invention exhibits 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 coefficient (Dk) of the cured product of the resin composition of the present invention may be 3.3 or less, 3.2 or less, 3.1 or less, or 3.0 or less. , below 2.9 or below 2.8.

In one embodiment, the cured product of the resin composition of the present invention exhibits a low dielectric loss factor (Df). For example, when measured at 5.8 GHz and 23°C as described in the "Dielectric Properties" column described later, the dielectric dissipation factor (Df) of the cured product of the resin composition of the present invention is preferably 0.01 or less, 0.008 or less, and 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 exhibits high thermal conductivity. For example, when measured by the hot plate 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, 2.8 W/mK or more, or 2.8 W/mK or more. More than mK, 3W/mK or more, 3.1W/mK or more, or 3.2W/mK or more.

The resin composition of the present invention can be suitably used as a resin composition for sealing a semiconductor chip (resin composition for semiconductor sealing). The resin composition of the present invention can also be suitably used as a resin composition for a rewiring formation layer (resin composition for a rewiring formation layer) used as an insulating layer for forming a rewiring layer in a semiconductor chip package. Furthermore, the resin composition of the present invention can 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 is more suitably used as an interlayer insulation for forming a printed wiring board. Layer resin composition (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with built-in parts. The resin composition of the present invention can further be used as necessary resin compositions such as sheet-shaped laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die attach materials, hole filling resins, and parts embedding resins. It is used in a wide range of applications.

[Sheet Laminates (Resin Sheets, Prepregs)] The resin composition of the present invention may be used as it is, or may be used in the form of a sheet-like laminate containing the resin composition.

As a sheet-like laminate material, resin sheets and prepregs as shown below are preferable.

In one embodiment, the resin sheet includes a support and a layer of resin composition provided on the support (hereinafter referred to as "resin composition layer"), which is characterized in that the resin composition layer is formed of the resin composition of the present invention.

The preferred value of the thickness of the resin composition layer varies depending on the application, and can be appropriately determined according to 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, 60 μm or less, or 50 μm or less from the viewpoint of thinning printed wiring boards and semiconductor chip packages. The lower limit of the thickness of the resin composition layer is not particularly limited, but may be generally 1 μm or more, 5 μm or more, or the like.

Examples of the support include, for example, films made of plastic materials, metal foils, release paper, preferably films made of plastic materials, and metal foils.

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

When a metal foil is used as a support body, examples of the metal foil include copper foil, aluminum foil, etc., preferably copper foil. As the copper foil, a foil made of a single metal of copper, or an alloy of copper and other metals (such as tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used.

The support body can also be subjected to matte treatment, corona treatment, and antistatic treatment on the surface that is bonded to the resin composition layer. Furthermore, as the support body, a support body with a release layer having a release layer on the surface bonded to the resin composition layer can also be used. The release agent used for the release layer of the support with release layer is, for example, one or more selected from the group consisting of alkyd resin, polyolefin resin, urethane resin, and silicone resin. Release agent. The support body with the release layer can also use commercially available products, such as "SK-1" and "AL-5" manufactured by Lintec Co., Ltd., which have a release layer mainly composed of an alkyd resin release agent. , "AL-7", "LUMIRROR T60" manufactured by Toray Corporation, "PUREX" manufactured by Teijin Corporation, "UNIPEEL" manufactured by UNITIKA Corporation, etc.

The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, more preferably in the range of 10 μm to 60 μm. Moreover, when using the support body with a release layer, it is preferable that the whole thickness of the support body with a release layer is the said range.

As the support, a metal foil with a support base in which a peelable support base is bonded to a thin metal foil can also be used. In one embodiment, the metal foil with a support base includes a support base, a release layer provided on the support base, and a metal foil provided on the release layer. When using a metal foil with a supporting substrate as a support, the resin composition layer is arranged on the metal foil.

In the metal foil with supporting base material, the material of the supporting base material is not particularly limited, for example, copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as a support base material, it may be electrolytic copper foil or rolled copper foil. In addition, the peeling layer is not particularly limited as long as it can peel the metal foil from the supporting base material, and examples thereof include alloys of elements selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P. layer; organic film, etc.

Among the metal foils 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 supporting base material, the thickness of the supporting base material is not particularly limited, but is preferably in the range of 10 μm to 150 μm, more preferably in the range of 10 μm to 100 μm. In addition, the thickness of the metal foil may be in the range of, for example, 0.1 μm to 10 μm.

In one embodiment, the resin sheet may further include arbitrary layers as necessary. As this arbitrary layer, the protective film etc. which are provided in the surface (ie, the surface opposite to a support body) of the resin composition layer, for example which are bonded to a support body are mentioned, for example. The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating a protective film, it is possible to suppress adhesion of dust and the like to the surface of the resin composition layer and to suppress scratches.

Resin flakes can be formed by, for example, directly applying a liquid resin composition, or preparing a resin varnish in which a resin composition is dissolved in an organic solvent, using a die coater, etc., to coat a support, and then drying to form a resin composition. made of layers.

Examples of the organic solvent are the same as those described as the components of the resin composition. An organic solvent may be used individually by 1 type, and may use it in combination of 2 or more types.

Drying can be carried out by known methods such as heating and blowing hot air. The drying conditions are not particularly limited, but they are dried until the organic solvent content in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although it varies with the boiling point of the organic solvent in the resin composition or resin varnish, for example, when using a resin composition or resin varnish containing 30% by mass to 60% by mass of organic solvent, dry it at 50°C to 150°C for 3 minutes. In 10 minutes, a resin composition layer can be formed.

Resin flakes can be stored in roll form. When the resin sheet has a protective film, it can be used by peeling off the protective film.

In one embodiment, the prepreg is formed by impregnating the resin composition of the present invention into a sheet-shaped fibrous base material.

The sheet-like fiber substrate used for the prepreg is not particularly limited, and glass cloth, aramid nonwoven fabric, liquid crystal polymer nonwoven fabric, etc., which are commonly used as the substrate for prepreg sheets, can be used. From the viewpoint of thinning printed wiring boards and semiconductor chip packages, the thickness of the flaky fibrous substrate is preferably at most 50 μm, more preferably at most 40 μm, more preferably at most 30 μm, and most preferably at most 20 μm. The lower limit of the thickness of the flake-shaped fibrous substrate is not particularly limited. Usually 10 μm or more.

Prepregs can be produced by known methods such as hot melt method and solvent method.

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

The sheet-like build-up material of the present invention can be suitably used for sealing a semiconductor wafer (for semiconductor sealing), and can be suitably used for a rewiring formation layer as an insulating layer for forming a rewiring layer. The sheet-like laminated material of the present invention can be suitably used to form an insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can also be suitably used to form an interlayer insulating layer of a printed wiring board (interlayer insulating layer of a printed wiring board). use).

[Semiconductor Chip Package] The semiconductor chip package of the present invention includes a sealing layer formed of a cured product of the resin composition of the present invention. The semiconductor chip package of the present invention may also include an insulating layer (rewiring formation layer) for forming a rewiring layer made of a cured product of the resin composition of the present invention as described above.

A semiconductor chip package can be manufactured by, for example, using the resin composition and resin sheet of the present invention, by a method including the following steps (1) to (6). In order to form the sealing layer in step (3) or the rewiring formation layer in step (5), the resin composition and resin sheet of the present invention may be used. The following shows an example of forming a sealing layer or a rewiring forming layer using a resin composition or a resin sheet, but the technique of forming a sealing layer or a rewiring forming layer of a semiconductor chip package is known, and those skilled in the art can use this The inventive resin composition or resin sheet is used to manufacture semiconductor packages according to known techniques. (1) The step of laminating a temporary fixed film on the substrate, (2) The step of temporarily fixing the semiconductor wafer on the temporary fixing film, (3) The step of forming a sealing layer on the semiconductor wafer, (4) The step of peeling the substrate and the temporarily fixed film from the semiconductor wafer, (5) A step of forming a rewiring formation layer as an insulating layer on the substrate of the semiconductor wafer and the surface from which the temporary fixing film is peeled off, and (6) A step of forming a rewiring layer as a conductor layer on the rewiring forming layer.

-step 1)- The material used for the substrate is not particularly limited. Examples of substrates include silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel plates (SPCC); FR-4 substrate); a substrate made of bismaleimide triazine resin (BT resin).

The material of the temporarily fixing film is not particularly limited as long as it can be peeled from the semiconductor wafer in step (4) and can temporarily fix the semiconductor wafer. As the temporary fixing film, a commercially available one can be used. Examples of commercially available products include RIVA ALPHA manufactured by Nitto Denko Co., Ltd., and the like.

-Step (2)- The semiconductor chip is temporarily fixed on the temporary fixing film in such a way that the electrode pad surface thereof is bonded to the temporary fixing film. The temporary fixation of the semiconductor wafer can be performed using known devices such as flip-chip bonders, die bonders, and the like. The layout and number of semiconductor chips can be appropriately set according to the shape and size of the temporarily fixed film, the number of semiconductor packages produced for the purpose, etc., for example, it can be temporarily fixed in a matrix arrangement of multiple columns and multiple rows.

-Step (3)- The resin composition of the present invention is coated on a semiconductor wafer, or the resin composition of the resin sheet of the present invention is laminated on a semiconductor wafer, and cured (for example, thermally cured) to form a sealing layer.

By using the resin composition of the present invention containing the diester compound (X) having a core unit composed of a divalent aliphatic group, the resin composition can be laminated in the form of a resin sheet even when the resin composition is directly coated In the case of layers, good fluidity can be exhibited during sealing and forming.

For example, when used in the form of a resin sheet, the lamination of the semiconductor wafer and the resin sheet can be carried out by removing the protective film of the resin sheet, and then heating and pressing the resin sheet to the semiconductor wafer from the support side. As a member for heat-pressing a resin sheet to a semiconductor wafer (hereinafter referred to as "heat-pressing member"), for example, a heated metal plate (SUS mirror plate, etc.) or a metal roll (SUS roll) is exemplified. Also, instead of directly pressing the heat-pressing member on the resin sheet, it is preferable to press the resin sheet through an elastic material such as heat-resistant rubber in such a way that the resin sheet fully follows the surface irregularities of the semiconductor wafer. The lamination of the semiconductor chip and the resin sheet can be carried out by vacuum lamination, and the lamination conditions are the same as the lamination conditions described later in relation to the manufacturing method of the printed wiring board, and the preferred range is also the same.

After lamination, the sealing layer is formed by thermosetting the resin composition. The thermosetting conditions are the same as the thermosetting conditions mentioned later in connection with the manufacturing method of a printed wiring board.

The support body of the resin sheet can be peeled off after the resin sheet is laminated on the semiconductor wafer by thermosetting, and the support body can also be peeled off before the resin sheet is laminated on the semiconductor chip.

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

-Step (4)- The method of peeling off the substrate and temporarily fixing the film can be appropriately changed according to the material of the temporarily fixing film, for example, the method of heating the temporarily fixing film to cause foaming (or expansion) and peeling off, and irradiating ultraviolet rays from the side of the substrate to make The method of peeling off the temporarily fixed film due to the reduction of its adhesive force, etc.

In the method of heating, foaming (or expanding) the temporarily fixed film and peeling off, the heating condition is usually 100-250° C. for 1-90 seconds or 5-15 minutes. In addition, in the method of irradiating ultraviolet rays from the substrate side to reduce the adhesive force of the temporarily fixed film and peel it off, the irradiation amount of ultraviolet rays is usually 10 mJ/cm ² to 1000 mJ/cm ² .

-Step (5)- The material for forming the rewiring forming layer (insulating layer) is not particularly limited as long as it has insulating properties when the rewiring forming layer (insulating layer) is formed. From the viewpoint of ease of manufacturing semiconductor chip packages, photosensitive resins, Thermosetting resin. The resin composition and resin sheet of the present invention can also be used to form a rewiring forming layer.

After the rewiring formation layer is formed, a via hole may be formed in the rewiring formation layer for interlayer connection between the semiconductor chip and the conductor layer described later. The via hole is formed by a known method according to the material of the rewiring formation layer.

-Step (6)- The material of the conductor layer formed on the rewiring formation layer is not particularly limited. In a preferred embodiment, the conductive layer contains at least one metal selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium . The conductor layer may be a single metal layer or an alloy layer. As an alloy layer, for example, an alloy of two or more metals selected from the above group (such as nickel‧chromium alloy, copper‧nickel alloy and copper‧titanium alloy) layer of formation. Among them, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or a nickel‧chrome alloy is preferred from the viewpoint of the versatility, cost, and ease of patterning of the conductor layer formation. , copper‧nickel alloy, copper‧titanium alloy layer, more preferably a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or an alloy layer of nickel‧chromium alloy, and more preferably A single metal layer of copper is preferred.

The conductor layer can be 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 can be formed by plating. For example, by plating on the surface of the rewiring formation layer by semi-additive method, full-additive method and other known techniques in the past, a conductor layer with the required wiring pattern can be formed. Based on the viewpoint of ease of manufacture, it is preferred Formed by semiadditive 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 rewiring formation layer by electroless plating. Then, on the formed plating seed layer, form a mask pattern corresponding to the desired wiring pattern to expose a part of the plating seed layer. On the exposed plating seed layer, after forming a metal layer by electrolytic plating, the mask pattern is removed. Subsequently, the unnecessary plating seed layer is removed by etching or the like, and a conductor layer (rewiring layer) having a desired wiring pattern can be formed.

Step (5) and step (6) are repeated again, and the conductor layer (rewiring layer) and the rewiring forming layer (insulating layer) (build-up layer) are alternately laminated.

When manufacturing semiconductor chip packages, it is also possible to further implement (7) the step of forming a solder resist layer on the conductor layer (rewiring layer), (8) the step of forming bumps, and (9) cutting multiple semiconductor chip packages into individual semiconductor chips. The step of chip packaging and singulation. These steps can be performed according to various methods known to those skilled in the art for manufacturing semiconductor chip packages.

The above is an example of the method of firstly disposing the semiconductor chip and forming the rewiring layer on the surface of the electrode pad, that is, the case of manufacturing by the chip 1st (Chip-1 ^st ) method. In the semiconductor chip package of the present invention, in addition to the chip 1st method, a rewiring layer can also be provided first, and a semiconductor chip can be placed on the rewiring layer in a state where the electrode pad surface and the rewiring layer can be electrically connected. And sealing method, that is, redistribution layer 1st (RDL-1 ^st ) manufacturing method. The resin composition and resin sheet of the present invention with excellent narrow gap filling properties can realize semiconductor chip packaging with very little transmission loss required for 5G applications, regardless of the Chip-1 ^st method or the RDL-1 ^st method.

Using the resin composition of the present invention that exhibits good fluidity during molding and obtains excellent dielectric properties after hardening, the resin sheet forms the sealing layer, and the rewiring formation layer, so that the semiconductor package is fan-in (Fan-In) type package or Fan-out (Fan-Out) packaging can suppress the occurrence of flow marks, unfilled parts, and warpage, and realize semiconductor chip packaging with extremely low transmission loss. In one embodiment, the semiconductor chip package of the present invention is a fan-out (Fan-Out) package. The resin composition and the resin sheet of the present invention are applicable to fan-out panel-level packaging (FOPLP) or fan-out wafer-level packaging (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 this invention contains the insulating layer which consists of the hardened|cured material of the resin composition of this invention.

A printed wiring board can be manufactured by the method including the process of following (I) and (II) using the said resin sheet, for example. (I) A step of laminating a resin sheet on the inner substrate so that the resin composition layer of the resin sheet is bonded to the inner substrate. (II) A step of hardening (for example, thermosetting) the resin composition layer to form an insulating layer.

The "inner layer substrate" used in step (I) is a component that becomes a substrate of a printed wiring board, for example, a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, a thermosetting poly Phenyl ether substrate, etc. Moreover, the substrate can have a conductor layer on one or both sides thereof, and the conductor layer can also be patterned. Inner substrates with conductive layers (circuits) formed on one or both sides of the substrate are sometimes referred to as "inner circuit substrates". In addition, when manufacturing a printed wiring board, an intermediate product that should further form an insulating layer and/or a conductive layer is also included in the "inner layer substrate" in the present invention. When the printed wiring board is a circuit board with built-in parts, the inner substrate of the built-in parts can also be used.

The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heating and pressing the resin sheet onto the inner layer substrate from the side of the support. As a member for heat-pressing the resin sheet to the inner substrate (hereinafter also referred to as “heat-press member”), for example, a heated metal plate (SUS mirror plate, etc.) or a metal roll (SUS roll) is exemplified. In addition, the heat-pressing member may directly press the resin sheet, or may apply pressure through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the inner substrate.

The lamination of the inner substrate and the resin sheet can be carried out by vacuum lamination. In the vacuum lamination method, the heating and 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 heating and pressing pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably in the range of 0.29MPa to 1.47 In the range of MPa, the heating and pressing 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 preferably be carried out under reduced pressure conditions with a pressure below 26.7hPa.

Lamination can be performed with a commercially available vacuum laminator. As a commercially available vacuum laminator, for example, a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by NIKKO Material Co., Ltd., a batch type vacuum pressure laminator, etc. are exemplified.

After the lamination, the laminated resin sheet can be smoothed by applying pressure under normal pressure (atmospheric pressure), for example, from the support body side with a heating press member. The pressure conditions for the smoothing treatment may be the same as the heat pressing conditions for the above-mentioned laminate. Smoothing can be performed with a commercially available laminator. Moreover, lamination and smoothing can be performed continuously using the above-mentioned commercially available vacuum laminator.

The support can be removed between step (I) and step (II), and can also be removed after step (II). When using a metal foil as a support body, you may form a conductor layer using this metal foil, without peeling a support body. And when using a metal foil with a supporting substrate as a support, it is only necessary to peel off the supporting substrate (and the peeling layer). Also, a metal foil may be used to form the conductor layer.

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

For example, the thermosetting conditions of the resin composition layer vary according to the type of the resin composition, but in one embodiment, the curing temperature is preferably 120°C~250°C, more preferably 150°C~240°C, and more preferably 180°C ~230°C. The hardening time is preferably from 5 minutes to 240 minutes, more preferably from 10 minutes to 150 minutes, and more preferably from 15 minutes to 120 minutes.

Before thermosetting the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, before thermally hardening the resin composition layer, preheat the resin composition layer for more than 5 minutes at a temperature of 50°C~120°C, preferably 60°C~115°C, more preferably 70°C~110°C , preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and more preferably 15 minutes to 100 minutes.

When manufacturing a printed wiring board, (III) the step of opening holes in the insulating layer, (IV) the step of roughening the insulating layer, and (V) the step of forming a conductor layer can be further implemented. These steps (III) to (V) can be implemented according to various methods known to those skilled in the art for producing printed wiring boards. Also, when the support is removed after step (II), the support can be removed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and Implemented between steps (V). And according to need, by repeatedly implementing steps (I) to step (V) to form an insulating layer and a conductor layer, a multilayer wiring board can be formed.

In other embodiment, the printed wiring board of this invention can be manufactured using the said prepreg. The manufacturing method is basically the same as the case of using a resin sheet.

The step (III) is a step of opening holes in the insulating layer, thereby forming holes such as through holes, through holes, etc. in the insulating layer. Step (III) corresponds to the composition of the resin composition used to form the insulating layer, for example, using a drill, laser, plasma, etc. to implement. The size and shape of the hole can be appropriately determined according to the design of the printed wiring board.

Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), the removal of smears (de-smearing) is also performed. The order and conditions of the roughening treatment are not particularly limited, and the known order and conditions generally used when forming an insulating layer of a printed wiring board can be employed. For example, the insulating layer may be roughened by sequentially performing swelling treatment with swelling liquid, roughening treatment with oxidizing agent, and neutralization treatment with neutralizing solution.

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

The oxidizing agent used for the roughening treatment is not particularly limited, but for example, an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide is exemplified. Roughening treatment with an oxidizing agent such as alkaline permanganic acid solution is preferably carried out by immersing the insulating layer in an oxidizing solution heated to 60°C to 100°C for 10 minutes to 30 minutes. Moreover, the concentration of permanganate in the alkaline permanganic acid solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganic acid solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Atotech Corporation of Japan.

In addition, the neutralizing solution used for the roughening treatment is preferably an acidic aqueous solution, and as a commercial product, for example, "Reduction Solution Securiganth P" manufactured by Atotech Corporation of Japan is exemplified.

The treatment of the neutralizing solution can be carried out by immersing the surface roughened by the oxidizing agent in the neutralizing solution at 30°C to 80°C for 5 minutes to 30 minutes. In terms of workability, etc., it is preferable to immerse the object roughened by the oxidizing agent in a neutralizing solution at 40°C to 70°C for 5 minutes to 20 minutes.

Step (V) is a step of forming a conductive layer, and the conductive layer is formed on the insulating layer. The step (V) can be implemented in the same way as the step (6) described in connection with the manufacturing method of the semiconductor chip package.

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

The conductive layer can also be formed using metal foil. When metal foil is used to form the conductor layer, step (V) is preferably implemented between step (I) and step (II). For example, after the step (I), the support body is removed, and the metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be performed by a vacuum lamination method. Lamination conditions can be identical with the conditions described in step (1). Next, implement step (II) to form an insulating layer. Subsequently, using the metal foil on the insulating layer, the conductive layer with the required wiring pattern can be formed by subtractive method, modified semi-additive method and other conventional techniques.

Metal foil can be produced by known methods such as electrolysis and calendering, for example. Examples of commercially available metal foils include HLP foil and JXUT-III foil manufactured by JX Nippon Oil & Metal Co., Ltd., 3EC-III foil and TP-III foil manufactured by Mitsui Metal Mining Co., Ltd., and the like.

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

[semiconductor device] The semiconductor device of the present invention includes a layer formed 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 the printed wiring board of the present invention.

Examples of semiconductor devices include various semiconductor devices used in electrical products (such as computers, mobile phones, digital cameras, and televisions, etc.) and vehicles (such as locomotives, automobiles, trains, ships, and airplanes, etc.). [Example]

<Example 1> Synthesis of diester compound (A) In a 2-liter four-neck round flask equipped with a stirring device, a thermometer, a dropping funnel, and a nitrogen blowing inlet, measure 268 g (2.00 moles) of allylphenol, 239 g (1.00 moles) of sebacic acid dichloride, and formaldehyde 500 g of 1-isobutyl ketone was added, and the temperature was raised to 30° C. while stirring to dissolve the contents uniformly. 231 g (2.20 moles) of triethylamine was added dropwise thereto. The dropwise addition of triethylamine started when the temperature of the contents was 30°C. While paying attention to heat generation, it was added dropwise over 1 hour with a heating curve so that the liquid temperature became 60-70°C after the dropwise addition. Furthermore, after continuing stirring at 60-70 degreeC for 1 hour, 200 g of distilled water was added, and byproduct organic salt was completely dissolved. Then, the liquid was transferred to a separatory funnel, and left to separate to remove the lower layer (water layer). Next, 200 g of distilled water and 10 g of disodium phosphate were added, and after vigorous soaking, the liquid was separated by standing and the lower layer (aqueous layer) was discarded. Furthermore, water washing was repeated 3 times using 200 g of distilled water. Add an appropriate amount of magnesium sulfate (dehydrating agent) to the washed reaction solution, vibrate vigorously for dehydration, and perform precision filtration on the dehydrated reaction solution. Finally, using a rotary evaporator, etc., the reaction solvent was recovered from the filtrate by vacuum distillation (maximum temperature: 120° C.), and 405 g of the diester compound (A) was obtained as a liquid compound.

About the obtained diester compound (A), the viscosity was measured using the E-type viscometer (for 25 degreeC viscosity) and the vibration type viscometer (for 75 degreeC viscosity) based on the following measurement conditions. The diester compound (A) had a viscosity of 72 mPa·s at 25°C and a viscosity of 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 24mm, angle 1.34° Speed: 100rpm Temperature: 25°C

(Viscosity measurement conditions during heating) Measuring device: vibrating viscometer ("VM-10A-L" manufactured by SEKONIC Co., Ltd.) Temperature: 75°C

Moreover, the measurement by the gel permeation chromatography (GPC) method and infrared spectroscopy (IR) method was performed about the obtained diester compound (A). The GPC chart of the compound is shown in Figure 1a, and the IR chart is shown in Figure 1b. And in the 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 target molecular structure shown below.

<Example 2> Synthesis of diester compound (B) Except having used 188 g (2.00 mol) of phenols instead of allylphenol, it carried out similarly to Example 1, and obtained 325 g of diester compounds (B) as a solid compound.

The melting point of the obtained diester compound (B) was 60°C. And the vibrating viscometer was used to measure the viscosity as in Example 1, and the viscosity of the compound at 75° C. was 17 mPa·s. The GPC chart of the compound is shown in Figure 2a, and the IR chart is shown in Figure 2b. In the 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 target molecular structure shown below.

<Example 3> Synthesis of diester compound (C) Except having used 211 g (1.00 moles) of suberic acid dichloride instead of sebacic acid dichloride, it carried out similarly to Example 1, and obtained 370 g of diester compounds (C) as a liquid compound.

For the obtained diester compound (C), after the viscosity was measured using the E-type viscometer and the vibrating viscometer in the same manner as in Example 1, the viscosity at 25°C was 68mPa·s, and the viscosity at 75°C was 12mPa·s . The GPC chart of the compound is shown in Figure 3a, and the IR chart is shown in Figure 3b. And in the 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 target molecular structure shown below.

<Example 4> Synthesis of diester compound (D) Except having used 288 g (2.00 mol) of 1-naphthols instead of allylphenol, it carried out similarly to Example 1, and obtained 418 g of diester compounds (D) as a solid compound.

The melting point of the obtained diester compound (D) was 68°C. And after measuring the viscosity with a vibrating viscometer as in Example 1, the viscosity of the compound at 75° C. was 76 mPa·s. The GPC chart of the compound is shown in Figure 4a, and the IR chart is shown in Figure 4b. And in the 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 target molecular structure shown below.

<Example 5> Synthesis of diester compound (E) Except having used 368 g (2.00 mol) of pentafluorophenols instead of allylphenol, it carried out similarly to Example 1, and obtained 505 g of diester compounds (E) as a solid compound.

The melting point of the obtained diester compound (E) was 61°C. And after measuring the viscosity with a vibrating viscometer similarly to Example 1, the viscosity at 75° C. was 19 mPa·s. The GPC chart of the compound is shown in Figure 5a, and the IR chart is shown in Figure 5b. And in the 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 target molecular structure shown below.

<Comparative Example 1> Synthesis of diester compound (F) Except having used 203 g (1.00 moles) of isophthalic acid dichloride instead of sebacic acid dichloride, it carried out similarly to Example 1, and obtained 240 g of diester compounds (F) as a liquid compound.

For the obtained diester compound (F), after the viscosity was measured using the E-type viscometer and the vibrating viscometer in the same manner as in Example 1, the viscosity at 25°C was 6000mPa·s, and the viscosity at 75°C was 85mPa·s . The GPC chart of the compound is shown in Figure 6a, and the IR chart is shown in Figure 6b. And in the spectrum, a spectrum of m/z=398 corresponding 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 6~20 and Comparative Examples 2~4> (1) Preparation of resin composition Using the synthesized diester compounds (A)~(F), the compositions shown in the following Tables 1~3 were stirred and mixed while heating to 80°C to prepare a resin composition.

(2) Manufacture of hardened products The prepared resin composition was injection-molded into the gap between two glass plates, and cured by heating at 180° C. for 90 minutes in a heat-circulating oven to obtain a cured product with a thickness of about 1 mm.

Using the obtained cured product and resin composition, an evaluation test was carried out in the following procedure. The results are shown in Tables 1-3.

[Dielectric properties] Cut the cured product into test pieces with a width of 2 mm and a length of 80 mm, and use a dielectric coefficient measuring device (manufactured by Kanto Applied Electronics Development Co., Ltd. "CP521") and a network analyzer (manufactured by Agilent Technologies "E8362B") , The specific permittivity and dielectric loss factor were measured by the cavity resonance method at a frequency of 5.8GHz and 23°C. For each cured product, two test pieces were measured (n=2), and the average value was calculated.

[Toughness evaluation] Cut the cured product into test pieces with a width of 30mm and a length of 80mm, and visually confirm the state when it is bent in half in the longitudinal direction by 180°. ○: No cracks or cracks were observed in the hardened product ×: Cracks and damage are seen in the hardened product

[Thermal conductivity] Put each resin composition into a specific container, heat it in a heat circulation oven at 180°C for 90 minutes to harden, and make a cylindrical hardened product with a thickness of 10mm and a diameter of φ36mm. The thermal conductivity of the obtained cylindrical hardened product was measured by the hot plate method using a thermophysical property measuring device ("TPS-2500" manufactured by Kyoto Denshi Kogyo Co., Ltd.) in a constant temperature environment at a measurement temperature of 25°C and 40% RH.

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

Claims (24)

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

(wherein, X _core represents a divalent aliphatic group, X ¹ _end and X ² _end each independently represent an aromatic ring that may have substituents, and at least one of X ¹ _end and X ² _end is a group selected from unsaturated aliphatic Aromatic rings with one or more of aromatic hydrocarbon groups, halogen atoms, alkyl groups, and aryl groups as substituents). The diester compound according to claim 1, wherein in the X _core , the number of carbon atoms in the divalent aliphatic group is 6 or more. The diester compound according to claim 1, wherein in X _core , the divalent aliphatic group is an alkylene group. The diester compound according to claim 1, wherein both of X ¹ _end and X ² _end are aromatic rings having unsaturated aliphatic hydrocarbon groups as substituents. The diester compound according to claim 1, wherein in X ¹ _end and X ² _end , the unsaturated aliphatic hydrocarbon group is an allyl group. The diester compound as claimed in item 1, wherein in X ¹ _end and X ² _end , the aromatic ring is an aromatic carbocyclic ring with 6 to 14 carbon atoms. The diester compound of claim 1, which is liquid at 25°C. The diester compound according to Claim 1 has a viscosity of 300 mPa·s or less at 25°C. A resin crosslinking agent comprising a diester compound represented by the following formula (X),

(In the formula, X _core represents a divalent aliphatic group, and X ¹ _end and X ² _end each independently represent an aromatic ring which may have a substituent). The resin cross-linking agent as claimed in item 9, wherein the diester compound is the diester compound as claimed in any one of items 1 to 8. A resin composition, which is a resin composition comprising a diester compound (X) and a crosslinkable resin (Y), wherein the diester compound (X) is represented by the following formula (X),

(In the formula, X _core represents a divalent aliphatic group, and X ¹ _end and X ² _end each independently represent an aromatic ring which may have a substituent). The resin composition according to claim 11, wherein the diester compound (X) is the diester compound according to any one of claims 1-8. The resin composition according to claim 11, wherein the crosslinkable resin (Y) is at least one selected from the group consisting of thermosetting resins and radically polymerizable resins. The resin composition according to claim 11, further comprising an inorganic filler. The resin composition according to claim 11, further comprising an organic solvent. Such as the resin composition of claim 11, which is used for sealing semiconductors. The resin composition as claimed in item 11 is used for the 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 disposed on the support. A prepreg, which is impregnated with the resin composition according to any one of claims 11 to 17 in a sheet-shaped fiber substrate. 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 hardened resin composition according to any one of claims 11 to 16. Such as the semiconductor chip package of claim 21, which is a fan-out (Fan-Out) package. A printed wiring board comprising an insulating layer made of a hardened resin composition according to any one of Claims 11-15, 17. A semiconductor device comprising the semiconductor chip package according to Claim 21 or 22 or the printed wiring board according to Claim 23.

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