Novel curing agent and method of preparing same

Abstract

The present invention relates to a novel curing agent including a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxy group, which exhibits excellent low dielectric loss characteristics (low Df), desmear properties, copper foil adhesion, and solution stability, a preparation method therefor, and an epoxy composition, a cured product, and an article including same. Not only does the curing agent of the present invention exhibit excellent solution stability, but also the epoxy composition comprising the curing agent and epoxy resin of the present invention achieves excellent low dielectric loss, desmear properties, and copper foil adhesion. Due to these improved properties, therefore, the epoxy composition comprising the curing agent of the present invention is suitable for use as an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, an underfill material, and the like.

Description

Novel curing agent and method for manufacturing curing agent

[0001] The present invention relates to a curing agent comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group, a method for manufacturing the same, an epoxy composition comprising the same, a cured product, and an article. Specifically, the invention relates to a novel curing agent comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group that exhibits excellent low dielectric loss (low Df), desmearability, adhesion, and solution stability, a method for manufacturing the same, an epoxy composition comprising the same, a cured product, and an article.

[0002] With the advancement of AI, data centers, and HPC (High Performance Computing) technologies, the importance of high-capacity data transmission and reception technologies is increasing. Accordingly, there is a demand for the development of semiconductor packaging material technologies that enable the transmission of large volumes of data as quickly as possible without transmission loss. Since high dielectric loss values ​​in epoxy materials used for semiconductor packaging lead to significant data transmission loss and degraded signal quality, the low dielectric loss (low Df) characteristic of semiconductor materials is a critical feature for high-quality, high-speed data transmission.

[0003] As disclosed in Patent No. 2051374, the most representative method for lowering the dielectric loss of epoxy materials is to use an active ester-based compound as a curing agent. Although the dielectric loss characteristics of epoxy insulating materials have been improved by the use of conventional active ester-based curing agents, there are problems such as insufficient solution dispersibility, desmearability, and adhesion to the copper foil layer.

[0004] Therefore, in order to manufacture semiconductor components for ultra-high-speed semiconductor data transmission, there is a need to develop an epoxy insulating material that can simultaneously satisfy excellent low dielectric loss (i.e., low Df) characteristics, as well as desmear processability and copper foil adhesion.

[0005] As mentioned above, there is a need to develop a material that satisfies excellent low dielectric loss characteristics and processability, specifically solution stability, desmearability, and adhesion, in a cured product of an epoxy resin (hereinafter referred to as "epoxy cured product"). The inventors have discovered that a novel curing agent comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group of the present invention not only exhibits improved processability in epoxy materials, specifically excellent solution stability, desmearability, and adhesion, but also satisfies excellent low dielectric loss characteristics in the cured product of the epoxy, and the present invention is based thereon. Accordingly, the present invention provides a novel curing agent comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group, a method for manufacturing the same, an epoxy composition containing the same, a cured product, and an article.

[0006] In a first aspect of the present invention, a curing agent comprising the following components (a), (b) and (c) is provided;

[0007] (a) A diester compound represented by the following chemical formula (1),

[0008] (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and

[0009] (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2).

[0010]

[0011] In a second aspect of the present invention, a curing agent of the first aspect is provided, wherein the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the curing agent is 10 to 90: 5 to 60: 0.1 to 30.

[0012] In a third aspect of the present invention, the method comprises the step of mixing 0.6 to 1.4 equivalents of at least one amino aromatic alcohol selected from aminophenol and aminonaphthol per 1 equivalent (i.e., 2 equivalents based on the ester group) of a diester compound represented by the following formula (1).

[0013] (a) A diester compound represented by the following chemical formula (1),

[0014] (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and

[0015] (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2).

[0016] A method for manufacturing a curing agent including is provided.

[0017]

[0018]

[0019] In a fourth aspect of the present invention, a method for manufacturing a curing agent according to a third aspect is provided, wherein the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the curing agent is 10 to 90: 5 to 60: 0.1 to 30.

[0020] In a fifth aspect of the present invention, an epoxy composition is provided, comprising (A) an epoxy resin and (B) a curing agent, wherein the curing agent (B) comprises the curing agent of the first aspect or the second aspect.

[0021] In the sixth aspect of the present invention, a cured product of the epoxy composition of the fifth aspect is provided.

[0022] In the seventh aspect of the present invention, an article is provided comprising a cured product of the epoxy composition of the fifth aspect and / or the epoxy composition of the sixth aspect.

[0023] In the eighth aspect of the present invention, the article of the seventh aspect is provided, which is an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, or an underfill material.

[0024] The curing agent of the present invention, comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group, exhibits excellent low dielectric loss (Df), solution stability, desmearability, and copper foil adhesion depending on the specific compositional ratio of the constituent compounds. That is, the curing agent of the present invention, comprising a naphthyl ester group, an N-aromatic amide group, and an aromatic hydroxyl group, not only maintains an excellent balance of low dielectric loss (Df), solution stability, desmearability, and copper foil adhesion, but also makes it easy to adjust the composition of the curing agent so that the properties particularly required among these can be expressed depending on the application field.

[0025] The curing agent of the present invention can be easily prepared by modifying a dinaphthyl ester compound in a single step. Furthermore, by adjusting the degree of modification of the dinaphthyl ester compound by adjusting the equivalent amount (i.e., the amount used in the reaction) of the amino aromatic alcohol that is the reactant, the ratio of naphthyl ester groups, N-aromatic amide groups, and aromatic hydroxyl groups in the curing agent can be easily controlled, thereby enabling the balance of low dielectric loss and processability (specifically, solution stability, desmearability, and copper foil adhesion) achieved by the novel curing agent.

[0026] In addition, the epoxy composition of the present invention, which includes the curing agent of the present invention, is suitable for use as an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, an underfill material, etc., due to the excellent low dielectric loss (Df), solution stability, desmearability, and copper foil adhesion achieved by the curing agent of the present invention.

[0027] According to the present invention, a novel curing agent exhibiting excellent low dielectric loss characteristics, solution stability, desmearability, and copper foil adhesion in epoxy materials, a method for manufacturing the same, an epoxy composition comprising the same, a cured product of the epoxy composition, and an article comprising the epoxy composition are provided. These are described below.

[0028] A. Novel curing agent

[0029] According to one embodiment of the present invention, as a novel curing agent,

[0030] (a) A diester compound represented by the following chemical formula (1),

[0031] (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2) and

[0032] (c) A novel curing agent is provided comprising a diamide compound which is at least one of the following chemical formulas (3-1) and (3-2).

[0033]

[0034] In the novel curing agent above, the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound is 10 to 90: 5 to 60: 0.1 to 30. To ensure low dielectric loss characteristics, the diester compound is preferably present in a weight ratio of 10 to 90, more preferably 20 to 90. If the diester compound exceeds 90 weights, solution stability and adhesion characteristics may deteriorate, and if it is less than 10 weights, it is difficult to ensure low dielectric loss characteristics. To ensure low dielectric loss characteristics and processability, the amide ester compound is preferably present in a weight ratio of 5 to 60, more preferably 10 to 60. If the amide ester compound exceeds 60 weights, the dielectric loss value may increase, which is undesirable, and if it is less than 5 weights, solution stability and adhesion characteristics may deteriorate. The diamide compound is present in a weight ratio of 0.1 to 30, preferably 0.1 to 25, in terms of the balance of low dielectric loss characteristics and processability. If the diamide compound exceeds 30 weight percent, the dielectric loss value increases, and it is desirable for the ratio to be 0.1 or higher in terms of the balance of processability.

[0035] According to another embodiment of the present invention, the curing agent

[0036] (a) 10 to 90 parts by weight, preferably 20 to 90 parts by weight, of a diester compound represented by the above chemical formula (1),

[0037] (b) 5 to 60 parts by weight, preferably 10 to 60 parts by weight, of an amide ester compound of at least one of the above chemical formulas (2-1) and (2-2) and

[0038] (c) It may include 0.1 to 30 parts by weight, preferably 0.1 to 25 parts by weight, of a diamide compound that is at least one of the above chemical formulas (3-1) and (3-2).

[0039] The ester and amide groups, which are functional groups of the three compounds constituting the curing agent of the present invention, form a curing structure in which OH groups are not generated during the curing reaction with the epoxy resin, thereby enabling low Df characteristics of the epoxy cured product. In addition, due to the presence of amide groups and aromatic hydroxyl groups, not only are the dispersibility and solution stability of the epoxy composition improved, but the desmearability and adhesion of the epoxy cured product are also improved.

[0040] Accordingly, the low Df characteristics and processability (specifically, solution stability, desmearability, and adhesion) can be controlled by adjusting the degree of modification of the dinaphthyl ester compound according to the desired low Df characteristics, solution stability, desmearability, and adhesion. That is, the low Df characteristics and processability of the curing agent, epoxy composition, and / or epoxy cured product can be controlled by appropriately adjusting the weight ratio of the three components constituting the curing agent. As described below, the weight ratio of the compounds constituting the novel curing agent can be controlled by adjusting the degree of modification by controlling the relative ratio of the dinaphthyl ester compound and the amino aromatic alcohol, which are reactants, during the preparation of the curing agent.

[0041] Accordingly, the novel curing agent according to the present invention exhibits excellent low dielectric loss characteristics, solution stability, desmearability, and copper foil adhesion.

[0042] The novel curing agent described above acts as a curing agent for epoxy resin (hereinafter referred to as "epoxy curing agent"). The novel curing agent has a curing agent equivalent (equivalent of reactive functional groups reacting with the epoxy resin) of 70 to 300 g / Eq, preferably 80 to 250 g / Eq. It is desirable for the curing agent equivalent to be within the above range in terms of ensuring low dielectric loss characteristics and processability. It is undesirable for the curing agent equivalent to be less than 70 g / Eq or more than 300 g / Eq in terms of not ensuring low dielectric loss characteristics and processability.

[0043] B. Method for manufacturing a novel curing agent

[0044] The curing agent according to the present invention is prepared by a single-step reaction of modifying a dinaphthyl ester compound, as shown in the reaction scheme below. That is, it is prepared by a single-step reaction of a dinaphthyl ester compound and an amino aromatic alcohol. As the amino aromatic alcohol, at least one of aminophenol and aminonaphthol may be used.

[0045] [Reaction Example of Dinaphthyl Ester Compound]

[0046]

[0047] [Reaction product of reaction between dinaphthyl ester compound and aminophenol]

[0048]

[0049] [Reaction product of reaction between dinaphthyl ester compound and aminonaphthol]

[0050]

[0051] The single-step reaction of the above dinaphthyl ester compound and the amino aromatic alcohol (i.e., aminophenol and / or aminonaphthol) can control the weight ratio of the compounds constituting the curing agent, i.e., the weight ratio of the above (a) diester compound, (b) amide ester compound and (3) diamide compound, depending on the degree of modification of the dinaphthyl ester compound (i.e., the equivalent ratio of the dinaphthyl ester compound to the amino aromatic alcohol).

[0052] The reaction between the above dinaphthyl ester compound and the amino aromatic alcohol may be carried out by contact, for example, mixing the dinaphthyl ester compound and the amino aromatic alcohol, though not limited thereto. Mixing may be carried out, for example, by stirring the reactants, though not limited thereto.

[0053] In the above reaction, 0.6 to 1.4 equivalents, preferably 0.6 to 1 equivalent, of an amino aromatic alcohol may be used for every 1 equivalent (2 equivalents based on the ester group) of a dinaphthyl ester compound. If the amount of amino aromatic alcohol is less than 0.6 equivalents, it is difficult to ensure solution stability, adhesion, and desmearability, and if the amount of amino aromatic alcohol exceeds 1.4 equivalents, the low dielectric loss characteristics deteriorate.

[0054] The reaction may be carried out at a temperature of 80°C to 180°C, preferably 80°C to 160°C, taking into account the solubility of the reactants and the reaction time. A temperature below 80°C is undesirable because the reaction rate may be significantly slowed down, and a temperature above 180°C is undesirable because side reactions may occur.

[0055] The reaction time varies depending on the structure of the reactants, the extent of the reaction, the solvent, and the amount of catalyst, but it is desirable to have a reaction time of 1 hour to 48 hours, preferably 4 hours to 12 hours, in terms of reaction efficiency. Less than 1 hour is undesirable because it is difficult for a sufficient reaction to proceed, and more than 48 hours is undesirable because additional reactions may occur.

[0056] The above reaction may be carried out in the presence of an acid or base catalyst and a solvent, as needed.

[0057] When a separate acid or base catalyst is used, the reaction rate can be accelerated. Examples of usable acid catalysts include, but are not limited to, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid, nitric acid, acetic acid, etc. Examples of base catalysts include, but are not limited to, NaOH, KOH, K2CO3, Na2CO3, KHCO3, NaHCO3, triethylamine, diisopropylethylamine, pyridine, etc. These catalysts may be used alone or in combination of two or more. When an acid catalyst is used, it may be used in an amount of 0.01 to 0.1 equivalents per 1 equivalent of the amino aromatic alcohol used in the reaction. When a base catalyst is used, it may be used in an amount of 0.1 to 1 equivalent per 1 equivalent of the amino aromatic alcohol.

[0058] In this case, if the amount of acid catalyst used is less than 0.01 equivalents, the effect of using the catalyst may be insufficient, and if it is used in excess of 0.1 equivalents, it is undesirable as the reaction may not proceed. When using a base catalyst, if the amount of base catalyst used is less than 0.1 equivalents, the effect of using the catalyst may be insufficient, and even if it is used in excess of 1 equivalent, it is unnecessary as the effect of adding the base catalyst does not increase further.

[0059] In addition, a solvent may be used as needed. For example, if the viscosity of the reactants at the reaction temperature is suitable for the reaction to proceed without a separate solvent, a solvent may not be used. That is, if the viscosity of the reactants is low enough that mixing and stirring of the reactants can proceed smoothly without a solvent, a separate solvent is not required, which can be easily determined by a person skilled in the art. If a solvent is used, any solvent may be used as long as it can effectively dissolve the reactants, does not adversely affect the reaction, and can be easily removed after the reaction. Examples of solvents that may be used, though not limited thereto, include toluene, xylene, acetonitrile, THF (tetrahydrofuran), MEK (methyl ethyl ketone), DMF (dimethyl formamide), DMSO (dimethyl sulfoxide), methylene chloride (MC), chloroform (CHCl3), and water (H2O). These solvents may be used individually or in combination of two or more. The amount of solvent used is not particularly limited and can be used in a suitable amount within a range where the reactants are sufficiently dissolved and no undesirable effects are applied to the reaction, and a person skilled in the art can make a suitable selection taking this into consideration.

[0060] Upon completion of the above reaction, a novel curing agent according to the present invention, i.e.

[0061] (a) A diester compound represented by the above chemical formula (1),

[0062] (b) an amide ester compound of at least one of the above chemical formulas (2-1) and (2-2) and

[0063] (c) A novel curing agent is provided comprising a diamide compound which is at least one of the chemical formulas (3-1) and (3-2) above. In addition, in the novel curing agent prepared by the above manufacturing method, the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound is 10 to 90: 5 to 60: 0.1 to 30, and a curing agent is prepared to which all the details described in item A. Novel Curing Agent above apply.

[0064] As is generally known in the field of chemistry, not all reactants proceed completely in a chemical reaction, and the reaction product may contain substances that are incidentally included in addition to the curing agent of the present invention intended herein, and the reaction product containing such various substances may also be used as a curing agent. Furthermore, naphthol, etc. generated during the reaction may also be included in the reaction product.

[0065] C. Epoxy composition

[0066] In another embodiment of the present invention, an epoxy composition is provided that exhibits not only improved low dielectric loss characteristics in an epoxy cured product but also excellent desmearability, copper foil adhesion, and solution stability, wherein the epoxy composition of the present invention comprises (A) an epoxy resin and (B) a curing agent, and (B) the curing agent comprises the novel curing agent of the present invention.

[0067] The epoxy composition of the present invention may additionally include one or more of (C) an inorganic filler, (D) a thermoplastic resin, and (E) a curing catalyst, as needed. The components of the epoxy composition of the present invention will be described individually below.

[0068] (A) Epoxy resin

[0069] The epoxy composition of the present invention comprises an epoxy resin (A) as the main resin. The epoxy resin (A) may be any epoxy resin conventionally known in the art, and its type and / or physical properties are not limited. Details regarding such epoxy resins are generally known in the art and are not described in detail herein.

[0070] General epoxy resins are not limited thereto, but include, for example, glycidyl-based epoxy resins selected from the group consisting of bisphenol, biphenyl, naphthalene, benzene, thiodiphenol, fluorene, anthracene, isocyanurate, triphenylmethane, 1,1,2,2-tetraphenylethane, tetraphenylmethane, 4,4'-diaminodiphenylmethane, aminophenol, glycidyl ether-based epoxy resins having alicyclic, aliphatic, or novolac unit, glycidylamine-based epoxy resins, and glycidyl ester-based epoxy resins; and alicyclic epoxy resins, and one or more selected from these epoxy resins may be used. The general epoxy resins include both liquid and solid epoxy resins. The general epoxy resins may also include epoxy resins having additional alkoxysilyl groups in addition to epoxy groups.

[0071] In this technical field, it is common practice to blend and use various epoxy resins together, taking into account epoxy compositions, their cured products, their fields of application, and physical properties such as processability, drying properties, and viscosity in subsequent processing steps for epoxy compositions. Accordingly, those skilled in the art may appropriately mix and use various general epoxy resins as needed, considering the physical properties required for the field of application of the epoxy composition, and this is not described in detail in this specification.

[0072] The epoxy equivalent of the above epoxy resin is not particularly limited, but, for example, it may be 70 g / Eq to 1000 g / Eq, preferably 80 g / Eq to 1000 g / Eq, more preferably 80 g / Eq to 800 g / Eq, and even more preferably 100 g / Eq to 500 g / Eq. By using an epoxy resin within the above epoxy equivalent range, the crosslinking density of the cured product becomes sufficient, making it possible to secure the properties of the cured product.

[0073] The weight-average molecular weight (Mw) of the epoxy resin is also not particularly limited, but, for example, in terms of processability and compatibility with inorganic fillers, it may be 300 g / mol to 8000 g / mol, preferably 300 g / mol to 5000 g / mol, and more preferably 300 g / mol to 4000 g / mol. Here, the weight-average molecular weight of the epoxy resin is the weight-average molecular weight in polystyrene equivalent measured by gel permeation chromatography (GPC).

[0074] (B) Curing agent

[0075] The epoxy composition of the present invention includes a curing agent (B), and the curing agent includes the curing agent of the present invention described above; therefore, the contents of item A. Novel Curing Agent are all applied identically.

[0076] Furthermore, the curing agent (B) may additionally include not only the curing agent of the present invention described above, but also any curing agent generally known in the art as an epoxy curing agent (hereinafter also referred to as 'conventional curing agent').

[0077] The above-mentioned conventional curing agents are not limited thereto, but examples include active ester-based curing agents, phenol-based curing agents, cyanate ester-based curing agents, acid anhydride-based curing agents, etc., and depending on the needs, one or more of these may be used in any combination.

[0078] Any active ester-based curing agent known to be used in epoxy resins can be used as the above active ester-based curing agent. For example, as the active ester-based curing agent, a compound having two active ester groups in one molecule is preferred, although not limited thereto. An active ester compound obtained by the reaction of a carboxylic acid compound and a hydroxyl compound is preferred. Here, isophthalic acid, terephthalic acid, etc. are preferred as the carboxylic acid compound used to produce the active ester-based curing agent, and phenol, naphthol, etc. are preferred as the hydroxyl compound. The above active ester-based curing agent may be used as a single type or in any combination of two or more types. In terms of improving the low dielectric loss characteristics of the epoxy composition of the present invention, it is preferable to use the curing agent of the present invention together with a conventional active ester-based curing agent. A cured product of an epoxy composition in which the curing agent of the present invention and a conventional active ester-based curing agent are used together exhibits a dielectric loss of less than 0.006.

[0079] Any phenol novolak curing agent known to be used in epoxy resins may be used as the above-mentioned phenolic curing agent. For example, phenolic curing agents may include, but are not limited to, phenol novolak resin, trifunctional phenol novolak resin, cresol novolak resin, bisphenol A novolak resin, xylene novolak resin, triphenyl novolak resin, biphenyl novolak resin, dicyclopentadiene novolak resin, naphthalene novolak resin, phenol p-xylene resin, phenol 4,4'-dimethylbiphenylene resin, xylok (p-xylene modified) resin and / or compounds, and triazine compounds, etc. In addition, the above-mentioned phenolic curing agent may additionally have an alkoxysilyl group in addition to a phenolic group. Therefore, the above-mentioned phenolic curing agent also includes all phenolic curing agents having a phenolic group and an additional alkoxysilyl group. The above phenolic curing agent may be used in any combination of one or two or more types.

[0080] Any cyanate ester-based curing agent known to be used in epoxy resins can be used as the cyanate ester-based curing agent. For example, cyanate ester-based curing agents may include, but are not limited to, novolak-type (phenol novolak type, alkylphenol novolak type, etc.) cyanate ester-based curing agents, dicyclopentadiene-type cyanate ester-based curing agents, bisphenol-type (bisphenol A type, bisphenol F type, bisphenol S type, etc.) cyanate ester-based curing agents, and prepolymers in which some of these are triazinated. One or more of the above cyanate ester-based curing agents may be used in combination.

[0081] Any acid anhydride-based curing agent known to be used in epoxy resins can be used as the acid anhydride-based curing agent. Examples of acid anhydride-based curing agents include, but are not limited to, aliphatic acid anhydrides such as dodecenyl succinic anhydride (DDSA) and poly azelaic poly anhydride; alicyclic acid anhydrides such as hexahydrophthalic anhydride (HHPA), methyl tetrahydrophthalic anhydride (MeTHPA), and methylnadic anhydride (MNA); aromatic acid anhydrides such as trimellitic anhydride (TMA), pyromellitic acid dianhydride (PMDA), and benzophenonetetracarboxylic dianhydride (BTDA). The above acid anhydride-based curing agent may be used in a combination of one or more types.

[0082] The amount of curing agent in an epoxy composition is determined by the equivalent ratio with respect to the epoxy resin. Although not limited thereto, for example, the curing agent is used in a range of 0.7 to 1.4 equivalents, preferably 0.7 to 1.3 equivalents, per 1 equivalent of the epoxy resin. If the amount is less than 0.7 equivalents, sufficient low dielectric loss characteristics may not be secured, and if the amount exceeds 1.4 equivalents, the degree of curing of the epoxy cured product may decrease.

[0083] The amount of the above-mentioned curing agent is the amount of the curing agent according to the present invention when the curing agent of the present invention is used alone, and is the sum of the amount of the curing agent of the present invention and the amount of the conventional curing agent when the curing agent of the present invention and a conventional curing agent are used together as curing agents.

[0084] Meanwhile, the equivalent weight of the epoxy resin is the value obtained by dividing the solid mass of the epoxy resin by the number of epoxide functional groups, and the equivalent weight of the curing agent is the value obtained by dividing the solid mass of the curing agent by the 'number of functional groups capable of reacting with epoxy groups.' The equivalent weight of the curing agent is the equivalent weight of the sum of the amounts of all curing agents used in the formulation. Therefore, when the curing agent of the present invention is used alone, it is the equivalent weight of the curing agent of the present invention used; and when the curing agent of the present invention and a conventional curing agent are used together, it is the equivalent weight of the sum of the amount of the curing agent of the present invention used and the amount of the conventional curing agent. Here, 'solid mass' refers to the weight of the pure epoxy resin or curing agent excluding any accidental liquids and solvents that may be present in the epoxy resin or curing agent. The calculation of the equivalent weight of the epoxy resin or curing agent is generally well known in the technical field.

[0085] When a conventional curing agent is used in combination, the mixing ratio of the curing agent according to the present invention and the conventional curing agent is not particularly limited. Considering the physical properties of the intended cured product, the conventional curing agent may be used in any suitable ratio, which is generally known in the art and is not described in detail herein.

[0086] Meanwhile, specifically, for example, when the curing agent (a) of the present invention and a conventional active ester-based curing agent and / or a phenol-based curing agent (b) are used together, it is preferable that the curing agent (a) of the present invention and the conventional curing agent (b) be used together in a molar ratio of curing agent (a):conventional curing agent (b) of 0.5:9.5 to 9.5:0.5, preferably 9:1 to 1:9. That is, by mixing the curing agent (a) and the conventional active ester-based curing agent and / or phenol-based curing agent (b) in the above molar ratio, the curing agent mixed with respect to 1 equivalent of epoxy resin as described above can be used in a range of 0.7 to 1.4 equivalents, preferably 0.7 to 1.3 equivalents.

[0087] In the molar ratio of the above curing agent (a) and the conventional active ester-based curing agent and / or phenol-based curing agent (b), if the curing agent (a) of the present invention is used below the lower limit, it is undesirable in that the physical properties intended by using the curing agent of the present invention are not sufficiently secured, and even if the curing agent (a) exceeds the upper limit, it is undesirable in that the effect of the curing agent formulation of the present invention is no longer increased.

[0088] (C) Inorganic Filler

[0089] The epoxy composition of the present invention may additionally include an inorganic filler as needed. Inorganic fillers are components commonly used in the art to reinforce the physical properties of epoxy compositions.

[0090] Although not limited thereto, any inorganic filler known in the art to be used to reinforce the physical properties of epoxy resin may be used as an inorganic filler. Although not limited thereto, examples of inorganic fillers include silica (e.g., fused silica and crystalline silica), metal oxides such as zirconia, titania, alumina, and magnesium oxide, aluminum nitride, silicon nitride, and silsesquioxane. The above inorganic fillers may be used alone or in combination of two or more types. Regarding the average particle diameter of the inorganic filler, although not limited thereto, for example, the inorganic filler may be a spherical powder with a particle diameter (cut-size) of 0.01 μm to 100 μm, preferably 0.02 μm to 70 μm, and more preferably 0.02 μm to 50 μm, in terms of dispersibility, processability, and reliability. If the average particle size of the inorganic filler is less than 0.01㎛, it is not only expensive but may also cause problems with dispersion, and if it exceeds 100㎛, it may cause problems with fine pattern formation and filling.

[0091] Inorganic fillers are generally known in this technical field and are not described in detail here.

[0092] In the epoxy composition of the present invention, the content of the inorganic filler may be formulated to be 93% by weight or less based on the total weight of the solids of the epoxy composition (e.g., 93% by weight or less per 100% by weight of the solids of the epoxy composition), from the perspective of using an amount necessary to secure the physical properties required of the epoxy composition. Since the inorganic filler may be formulated as needed, the lower limit of the formula amount is not particularly limited; however, if added, it may be formulated to be at least 10% by weight (e.g., at least 10% by weight per 100% by weight of the solids of the epoxy composition) so that the effect of the addition is realized. The inorganic filler may be formulated specifically in an amount of 10% by weight to 93% by weight, preferably 20% by weight to 90% by weight, considering the securing of physical properties and dispersibility by the epoxy composition. If the amount is less than 10% by weight, it may be difficult to secure the physical properties of the epoxy cured product intended by the formulation of the filler, and if it exceeds 93% by weight, it may be difficult to disperse the filler.

[0093] (D) Thermoplastic resin

[0094] The epoxy composition of the present invention may additionally include a thermoplastic resin as needed. For example, a thermoplastic resin may be additionally used when it is necessary to impart filmability and / or flexibility.

[0095] As for the thermoplastic resin, any thermoplastic resin generally known to be used in this technical field, such as acrylic resin, phenoxy resin, polyvinyl acetal resin, polyimide resin, polyamideimide resin, polyether sulfone resin, and polysulfone resin, may be used as one type or in any combination of two or more types, and the structure, molecular weight, etc. of these thermoplastic resins are not limited. Details regarding thermoplastic resins are generally known in this technical field and are not described in detail here.

[0096] When a thermoplastic resin is used, it may be used in an amount generally used in this technical field, and the amount used is not particularly limited. However, for example, the thermoplastic resin may be incorporated as a component that can be added as needed, in an amount of 7% by weight or less (i.e., 7% by weight or less per 100% by weight of the total solid content of the epoxy composition). However, when a thermoplastic resin is incorporated, in order to produce the intended effect, for example, considering the processability (film formability) and / or flexibility of the epoxy composition, the thermoplastic resin may be incorporated in an amount of 0.5% to 7% by weight (i.e., 0.5% to 7% by weight per 100% by weight of the total solid content of the epoxy composition) based on the total solid content of the epoxy composition. If the thermoplastic resin is added in an amount of less than 0.5 weight%, the properties intended by the thermoplastic resin, such as film processability or flexibility, may not be sufficient, and if it exceeds 7 weight%, the properties of the epoxy material may deteriorate.

[0097] (E) Curing catalyst

[0098] The epoxy composition of the present invention may also include a curing catalyst as needed. By rapidly curing the epoxy composition using a curing catalyst, the crosslinking structure in the cured product becomes uniform and the crosslinking density is increased.

[0099] The above curing catalyst is not particularly limited, and any curing catalyst known in the art to be used as a curing catalyst for curing epoxy resins may be used. Only one type of the above curing catalyst may be used, or two or more types may be used in combination.

[0100] Examples of the above-mentioned curing catalysts include imidazole-based compounds, amine-based compounds, organophosphine-based compounds, organophosphonium salt-based compounds, etc.

[0101] The above imidazole-based compounds include 2-undecylimidazole, 2-heptadecylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1,2-dimethylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazole trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-methylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-dihydroxymethylimidazole, One or more types of 1,3,5-triazine-2,4-diamine6-[2-(2-methyl-1H-imidazole-1-yl)ethyl] and 1,3,5-triazine-2,4,6(1H,3H,5H)-trione, etc., may be used in combination.

[0102] As the above amine compounds, one or more of the following may be used: diethylamine, triethylamine, diethylenetetramine, triethylenetetramine, 4-dimethylaminopyridine (DMAP), benzyl dimethylamine (BDMA), trisdimethylaminomethylphenol (DMP-30), triethylenediamine, diazabicycloundecene (DBU), etc.

[0103] As for the above-mentioned organophosphine compounds and organophosphonium salt compounds, one or more types such as TPP, TPP-K, TPP-S, TPTP-S, TBP-DA, TPP-SCN, and TPTP-SCN (product name of Hokyo Gakaku Kogyo Co., Ltd.) may be used in combination.

[0104] The above-mentioned curing catalyst may be used in an amount generally used in this technical field. Although not limited thereto, the curing catalyst may be used in an amount of, for example, 0.1 to 10 parts by weight, or for example, 0.2 to 10 parts by weight, per 100 parts by weight of epoxy resin. If the amount of curing catalyst used is less than 0.1 parts by weight, the effect resulting from the use of the curing catalyst is negligible, and even if it exceeds 10 parts by weight, it is not desirable as there is no additional improvement effect. It is preferable to use the curing catalyst in the above amount in terms of promoting the curing reaction and controlling the curing reaction rate. By using the above-mentioned curing catalyst in the above range, curing proceeds rapidly, and an improvement in work throughput can be expected.

[0105] (F) Other additives

[0106] In any aspect of the present invention, other additives such as flame retardants, plasticizers, antimicrobial agents, leveling agents, defoaming agents, colorants, stabilizers, coupling agents, viscosity modifiers, diluents, and molding agents, which are conventionally incorporated into epoxy compositions in the art to control the properties of the epoxy composition, may also be incorporated as needed, to the extent that the properties of the epoxy composition are not impaired. Additionally, the epoxy composition may be dispersed using a solvent as needed so that the composition can be easily dispersed before curing. The types, composition, and content of such other additives and / or solvents are generally known to those skilled in the art and are not described in detail in this specification.

[0107] In the present invention, the term "solid content of the epoxy composition" refers to the amount of the components of the epoxy composition that are cured to form the final product (e.g., cured product), excluding any liquid components, such as liquid components and solvents, that are removed during drying and / or curing, in cases where a liquid component is incidentally present in the epoxy composition and / or a solvent is used (even if a component is liquid, a component that constitutes the final product is included in the solid content). For example, in the case of an epoxy composition comprising (A) an epoxy resin, (B) a curing agent, and optionally included (C) an inorganic filler, (D) a thermoplastic resin, (E) a curing catalyst, and / or (F) other additives, the term "solid content of the epoxy composition" refers to the total weight of the components of the epoxy composition that are cured to form the final product (e.g., cured product), excluding any liquid components, such as solvents, that are removed during drying and / or curing, from the epoxy composition containing these components (even if a component is liquid, a component that constitutes the final product is included in the solid content).

[0108] In addition, the term "composition of the present invention" in the above and below is understood to refer to an epoxy composition comprising (A) an epoxy resin and (B) a curing agent, and optionally, (C) an inorganic filler, (D) a thermoplastic resin, (E) a curing catalyst and / or (F) the other additives mentioned above.

[0109] For example, in the epoxy composition of the present invention, (B) a curing agent may be included in an amount ranging from 0.7 to 1.4 equivalents based on 1 equivalent of the epoxy resin, (C) an inorganic filler may be included in an amount of 93% by weight or less, preferably 10 to 93% by weight, based on the total weight of the epoxy composition, and (D) a thermoplastic resin may be included in an amount of 7% by weight or less, preferably 0.5% to 7% by weight, based on the total weight of the epoxy composition. The epoxy composition may also, if necessary, include (E) a curing catalyst and (F) other additives in amounts commonly used in the art. In the epoxy composition according to the present invention, the remainder of the content (e.g., the remainder at 100% by weight) may be epoxy resin.

[0110] In addition, the epoxy composition of the present invention includes these components within the above-mentioned mixing ratio range such that the total amount is 100% by weight based on the total solid content. If the composition of the components (e.g., component (C) and component (D)) expressed in weight percent based on the total weight of the solid content of the epoxy composition does not amount to 100% by weight, the remainder is composed of other components (specifically, (A) epoxy resin, (B) curing agent, (E) curing catalyst and / or (F) other additives) to amount to 100% by weight.

[0111] D. Cured products and uses of epoxy compositions

[0112] According to another embodiment of the present invention, a cured product of the epoxy composition according to the present invention is provided. The cured product may be obtained by curing the epoxy composition, for example, by thermal curing. A person skilled in the art may cur the epoxy composition by suitably selecting any curing method and curing conditions generally known in the art, and the curing method and / or curing conditions are not particularly limited.

[0113] In addition, the curing method and curing conditions of the epoxy composition are generally known in this technical field and are not described in detail here. The above cured product is a partially cured and fully cured epoxy cured product, and is used to include epoxy cured products without inorganic fillers and epoxy composites containing fillers. As described above, not only the low dielectric loss characteristics but also processability (specifically, desmearability and adhesion) are improved in the cured product formed from the epoxy composition of the present invention.

[0114] For example, the cured product of an epoxy composition containing the curing agent of the present invention exhibits a dielectric loss of less than 0.010, preferably less than 0.008, and more preferably less than 0.006. In addition, the cured product of an epoxy composition containing the curing agent of the present invention has a glass transition temperature of 120°C or higher, preferably 130°C or higher.

[0115] Furthermore, according to another embodiment of the present invention, an article comprising an epoxy composition and / or a cured product thereof according to any aspect of the present invention is provided.

[0116] As described above, the epoxy composition containing the curing agent of the present invention achieves not only low dielectric loss in the epoxy cured product but also excellent processability, namely desmearability and adhesion. The epoxy composition containing the curing agent of the present invention is suitable for insulating films, epoxy films for semiconductor packaging, adhesive films, build-up films, substrate films, underfill materials, epoxy molding materials, specifically next-generation semiconductor packaging components, for example, packaging components (materials) that process large amounts of data at ultra-high speed (advanced semiconductor packaging).

[0117] The above article may be an epoxy insulating film, specifically an insulating film for an IC substrate, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an underfill material, an epoxy molding material, for example, an epoxy molding material for semiconductor packaging, a next-generation semiconductor packaging component, for example, a packaging component that processes large amounts of data at ultra-high speed.

[0118] The method of manufacturing an epoxy insulating film using the epoxy composition of the present invention, e.g., an insulating film for an IC substrate, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an underfill material, an epoxy molding material, e.g., an epoxy molding material for semiconductor packaging, and a next-generation semiconductor packaging component, e.g., a packaging component for processing large amounts of data at ultra-high speed, is not particularly limited, and such articles may be manufactured by any method known in the art, which is not described in detail herein.

[0119] Although not limited thereto, for example, the above-described film-shaped article may be manufactured into a film by applying the epoxy composition of the present invention to a release film in a film-forming process, drying and curing it, or by extruding the epoxy composition. Various methods known in the art may be used as the above-described film-forming process and are not particularly limited, but examples include various printing methods such as offset printing and screen printing, blade coating, dip coating, spin coating, bar coating, slit coating, inkjet, and die coating.

[0120] Examples

[0121] The present invention will be explained in more detail below through examples. However, the examples are illustrative of the present invention and are not intended to limit the invention.

[0122] A. Synthetic Example

[0123] (1) Synthesis Example 1

[0124] 100g of a diester compound (chemical formula (1) below) and 10g of toluene were placed in a 2-neck flask equipped with a reflux condenser and stirred at 110°C for 30 minutes under nitrogen. Afterward, 7.61g of 5-amino-1-naphthol was added to the flask, the temperature was raised to 150°C, and stirring was continued for an additional 12 hours. After the reaction was finished, the reaction product was cooled to room temperature (15°C to 25°C, hereinafter the same) and dried using a vacuum pump to obtain a final compound (curing agent equivalent 174g / Eq) with a composition ratio of diester (1):amide ester (2-2): diamide (3-2) = 88:12:0.1 by weight.

[0125]

[0126] (2) Synthesis Example 2

[0127] Except for using 15.23 g of 5-amino-1-naphthol and adding 0.33 g of p-toluenesulfonic acid, the reaction was carried out in the same manner as in Synthesis Example 1 above to obtain a final compound (curing agent equivalent 151 g / Eq) with a composition ratio of diester (1):amide ester (2-2):diamide (3-2) = 60:36:4 by weight.

[0128] (3) Synthesis Example 3

[0129] Except for adding 15.67g of 3-aminophenol instead of 7.61g of 5-amino-1-naphthol, the reaction was carried out in the same manner as in Synthesis Example 1 above to obtain a final compound (curing agent equivalent 128 g / Eq) with a composition ratio of diester (1):amide ester (2-1):diamide (3-1) = 44:48:8 by weight.

[0130] (4) Synthesis Example 4

[0131] Except for adding 26.11g of 3-aminophenol and 9.28g of diisopropylethylamine instead of 7.61g of 5-amino-1-naphthol, the reaction was carried out in the same manner as in Synthesis Example 1 above to obtain a final compound (curing agent equivalent 106 g / Eq) with a composition ratio of diester (1):amide ester (2-1):diamide (3-1) = 25:55:20 by weight.

[0132] B. Preparation of cured epoxy products and evaluation of physical properties

[0133] (1) Dielectric loss (D f Preparation and evaluation of samples for measuring ) and Continuous Thermal Expansion (CTE)

[0134] <Sample Preparation>

[0135] The epoxy resin, curing agent, thermoplastic resin, and silica were dissolved in methyl ethyl ketone at room temperature according to the composition of Table 1 below. This mixture was mixed using a mixer at a speed of 1500 rpm for 30 minutes. Afterward, a curing catalyst was added and mixed to obtain a homogeneous solution. The mixture was then cast onto a release film to a uniform thickness, and the solvent on the cast film was dried in a convection oven heated to 70°C. The composition was cured on the dried film at 190°C for 90 minutes to prepare the sample. The sample size for dielectric loss measurement is 60mm x 50mm x 0.1mm, and the sample size for CTE measurement is 4mm x 40mm x 0.1mm.

[0136] <Sample Evaluation>

[0137] The dielectric loss of the fabricated epoxy film was evaluated at room temperature and 5.125 GHz using an Agilent Technologies E5071C. The thermal expansion characteristics of the cured epoxy, i.e., the dimensional change with temperature, were evaluated using a thermomechanical analyzer.

[0138] (2) Solution stability evaluation

[0139] Methyl ethyl ketone was added to the composition excluding silica in Table 1 below, and all components were completely dissolved at room temperature to form a clear solution. At this time, the solid content was 60% by weight. The precipitation of the composition was observed for one day at room temperature.

[0140] (Evaluation Criteria)

[0141] N: No precipitation

[0142] Y: Precipitation

[0143] (3) Preparation and evaluation of blister packs and samples for measuring adhesion strength

[0144] Sample Preparation

[0145] The epoxy resin, curing agent, thermoplastic resin, and silica were dissolved in methyl ethyl ketone at room temperature according to the composition of Table 1 below. This mixture was mixed using a mixer at a speed of 1500 rpm for 30 minutes. Afterward, a curing catalyst was added and mixed to obtain a homogeneous solution. The mixture was then cast onto a release film to a uniform thickness, and the solvent on the cast film was dried in a convection oven heated to 70°C. The dried film was laminated onto a copper foil substrate and cured in an oven at 120°C for 40 minutes and at 180°C for 20 minutes.

[0146] After desmearing the cured epoxy film, electroless copper plating and electroplating were performed, followed by heat treatment (curing) at 190°C for 2 hours.

[0147] <Blister and Adhesion Evaluation>

[0148] The presence of blisters was evaluated by observing the surface of the above sample, which was cured at 190°C after copper foil treatment. Then, the adhesive strength (kgf / cm²) was determined by measuring the load when the plated conductor layer of the cured copper foil sample was peeled vertically at a speed of 50 mm / min at room temperature. 2 evaluated ).

[0149] (Evaluation Criteria)

[0150] N: No blister creation

[0151] Y: Create blister

[0152] [Table 1]

[0153]

[0154] Note: The compounds used in Table 1 above are as follows.

[0155] (1) Samhwa Paint Co., Ltd., SSE-B20H™, EEW 420g / Eq.

[0156] (2) Samhwa Paint Co., Ltd., Serapoxy SHE0002™, EEW 348g / Eq.

[0157] (3) Samhwa Paint Co., Ltd., SSE-D30H™, EEW 438g / Eq.

[0158] (4) Sigma Aldrich, EEW 105g / Eq

[0159] (5) DIC Inc., HP4770™, EEW 205g / Eq.

[0160] (6) Sigma Aldrich, EEW 188.5g / Eq,

[0161] (7) Mitsubishi Kagaku Inc., YX4000HK™, EEW 190.

[0162] (8) DIC Co., Ltd., Epiclon EXB-8, 209g / Eq.

[0163] (9) DIC Co., Ltd., Epiclon HPC 8000L™, 220g / Eq.

[0164] (10) Meiwa Plastic Industries, HF-1M™, 107 g / Eq.

[0165] (11) Admatechs, SC2050-MTX™

[0166] (12) SEKISUI, BX-5™

[0167] (13) Sigma Aldrich

[0168] (14) Evonik, CUREZOL®

[0169] As can be seen from Table 1 above, the cured products of Examples 1 to 8 containing the curing agent of the present invention exhibit excellent low dielectric loss characteristics and processability (solution stability, desmearability, and adhesion). As can be seen from this, the balance of low dielectric loss characteristics and processability can be controlled by adjusting the reaction ratio of the dinaphthyl ester compound and the amino aromatic alcohol (aminophenol or aminonaphthol). When the concentration of the amino aromatic alcohol is low (Example 1), the low dielectric loss characteristics are excellent, and when the concentration of the amino aromatic alcohol is high (Example 2), processability, particularly adhesion, is excellent. In addition, when the curing agent of the present invention was mixed with a conventional curing agent (Examples 4 to 7), it was also possible to manufacture excellent epoxy cured products in which both low dielectric loss characteristics and processability were secured.

[0170] Meanwhile, Comparative Examples 1 to 4, which used conventional curing agents (active ester curing agents and / or phenol curing agents), failed to simultaneously satisfy low dielectric loss characteristics and processability.

[0171] Specifically, Comparative Examples 1 and 2, which used a conventional active ester curing agent, had relatively good dielectric loss characteristics, but unlike the case where the curing agent of the present invention was included (Examples 1 to 8), there were problems with processability. Comparative Example 1, which used a conventional active ester-based curing agent, dinaphthyl ester (corresponding to the diester of Formula (1) above), showed precipitation when storing the composition solution, and due to insufficient desmearability, blisters were formed and the adhesion was low. Comparative Example 2, which used a conventional active ester curing agent, ensured solution stability, but due to poor desmear etchability, not only were blisters formed but the adhesion was also low.

[0172] In addition, Comparative Example 3, which used a conventional active ester curing agent and a phenol novolak curing agent, not only had a somewhat high dielectric loss value but also poor solution stability. In the case of Comparative Example 3, although blistering was improved by mixing with the conventional novolak curing agent, there was a problem with the adhesion strength still being low. Specifically, it was found that the adhesion strength of Comparative Example 3 was much lower than that of Example 8, which had a similar formulation. Comparative Example 4, which used the conventional novolak curing agent, lacked low dielectric loss characteristics. Furthermore, although Comparative Example 4 had excellent solution stability, severe etching occurred during desmearing, making it impossible to manufacture copper foil samples.

[0173] The curing agent of the present invention exhibits low dielectric loss (Df), solution stability, desmearability, and copper foil adhesion, making it suitable for use as a curing agent for epoxy resins in epoxy compositions. Furthermore, the epoxy composition of the present invention containing the curing agent of the present invention can be usefully utilized as an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, an underfill material, etc.

Claims

1. A curing agent comprising the following components (a), (b) and (c); (a) A diester compound represented by the following chemical formula (1), (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2).

2. In Paragraph 1, A curing agent in which the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the above curing agent is 10 to 90:5 to 60:0.1 to 30.

3. A step comprising mixing 0.6 to 1.4 equivalents of at least one amino aromatic alcohol selected from aminophenol and aminonaphthol per 1 equivalent of a diester compound represented by the following chemical formula (1), (a) A diester compound represented by the following chemical formula (1), (b) an amide ester compound of at least one of the following chemical formulas (2-1) and (2-2), and (c) A diamide compound of at least one of the following chemical formulas (3-1) and (3-2). A method for manufacturing a curing agent comprising 4. A method for manufacturing a curing agent according to claim 3, wherein the weight ratio of (a) diester compound: (b) amide ester compound: (c) diamide compound in the curing agent is 10 to 90:5 to 60:0.1 to 30.

5. (A) comprising an epoxy resin and (B) a curing agent, The above (B) curing agent is an epoxy composition comprising the curing agent of claim 1 or 2.

6. Cured product of the epoxy composition of paragraph 5.

7. An article comprising the epoxy composition of paragraph 5.

8. In paragraph 7, the above article is an insulating film, an epoxy film for semiconductor packaging, an adhesive film, a build-up film, a substrate film, an epoxy molding material, or an underfill material.

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