KR102104524B1 - Epoxy resin composite and printed circuit board comprising isolation using the same - Google Patents

Abstract

여기서, R¹ 내지 R¹⁴은 각각 H, Cl, Br, F, C₁~C₃ 알킬, C₂~C₃ 알켄, C₂~C₃ 알킨으로 구성된 그룹에서 선택될 수 있고, m, n은 각각 1, 2 또는 3이다.The epoxy resin composition according to an embodiment of the present invention includes an epoxy compound including a mesogen structure, a curing agent, and an inorganic filler, wherein the epoxy compound has the structure of Formula 1, and the inorganic filler is aluminum oxide and nitride Contains aluminum.

Here, R ¹ to R ¹⁴ may be selected from the group consisting of H, Cl, Br, F, C ₁ to C ₃ alkyl, C ₂ to C ₃ alkene, and C ₂ to C ₃ alkyne, respectively, and m and n are 1, 2 or 3, respectively.

Description

Printed circuit board comprising an epoxy resin composition and an insulating layer using the same {EPOXY RESIN COMPOSITE AND PRINTED CIRCUIT BOARD COMPRISING ISOLATION USING THE SAME}

The present invention relates to an epoxy resin composition, and more particularly, to an epoxy resin composition used as an insulating layer of a printed circuit board.

The printed circuit board includes a circuit pattern formed on an insulating layer, and various electronic components can be mounted on the printed circuit board.

The electronic component mounted on the printed circuit board may be, for example, a heating element. The heat emitted by the heating element may degrade the performance of the printed circuit board.

With the high integration and high capacity of electronic components, interest in heat dissipation problems of printed circuit boards is growing. In general, an epoxy resin composition containing a bisphenol A type epoxy compound or a bisphenol F type epoxy compound is used for an insulating layer of a printed circuit board. However, the bisphenol A-type epoxy compound or the bisphenol F-type epoxy compound has a low viscosity, and thus has a problem of lacking curability, mechanical strength, toughness, and the like.

Accordingly, an epoxy resin composition containing a crystalline epoxy compound containing a mesogen structure has been used. Such an epoxy resin composition has excellent storage stability and curing properties before curing, but has limitations in obtaining required levels of heat resistance and thermal conductivity.

Technical problem to be achieved by the present invention is to provide a printed circuit board comprising an epoxy resin composition and an insulating layer using the same.

The epoxy resin composition according to an embodiment of the present invention includes an epoxy compound including a mesogen structure, a curing agent, and an inorganic filler, the epoxy compound has a structure of the following formula, and the inorganic filler is aluminum oxide and aluminum nitride It includes.

Here, R ¹ to R ¹⁴ may be selected from the group consisting of H, Cl, Br, F, C ₁ to C ₃ alkyl, C ₂ to C ₃ alkene, and C ₂ to C ₃ alkyne, respectively, and m and n are 1, 2 or 3, respectively.

The epoxy compound may include an epoxy compound of the following formula.

The aluminum nitride may exceed 0 wt% and less than 25 wt% with respect to the entire epoxy resin composition.

The inorganic filler may further include a boron nitride agglomerate having a density of 0.3 to 0.4 g / cm ³ .

The boron nitride agglomerate may have a diameter of 25 to 60 μm and a surface area of 5.5 to 7 μm ² .

The inorganic filler may include 20 to 200 parts by weight of the boron nitride agglomerate with respect to 10 parts by weight of the aluminum nitride.

The curing agent may include diaminodiphenylsulfone and dihydroxydiphenyl ester.

According to the embodiment of the present invention, it is possible to obtain an epoxy resin composition excellent in thermal conductivity. Using this, an insulating material having high heat resistance and high thermal conductivity can be obtained, and heat dissipation performance and reliability of the printed circuit board can be improved.

1 is a cross-sectional view of a printed circuit board according to an embodiment of the present invention.

The present invention can be applied to various changes and can have various embodiments, and specific embodiments will be illustrated and described in the drawings. However, this is not intended to limit the present invention to specific embodiments, and should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

Terms including ordinal numbers such as second and first may be used to describe various components, but the components are not limited by the terms. The terms are used only for the purpose of distinguishing one component from other components. For example, the second component may be referred to as a first component without departing from the scope of the present invention, and similarly, the first component may also be referred to as a second component. The term and / or includes a combination of a plurality of related described items or any one of a plurality of related described items.

The terms used in this application are only used to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms "include" or "have" are intended to indicate the presence of features, numbers, steps, actions, components, parts or combinations thereof described herein, one or more other features. It should be understood that the existence or addition possibilities of fields or numbers, steps, operations, components, parts or combinations thereof are not excluded in advance.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Terms such as those defined in a commonly used dictionary should be interpreted as having meanings consistent with meanings in the context of related technologies, and should not be interpreted as ideal or excessively formal meanings unless explicitly defined in the present application. Does not.

When a portion of a layer, film, region, plate, etc. is said to be “above” another portion, this includes not only the case “directly above” the other portion but also another portion in the middle. Conversely, when one part is "just above" another part, it means that there is no other part in the middle.

Hereinafter, exemplary embodiments will be described in detail with reference to the accompanying drawings, but the same or corresponding components are assigned the same reference numbers regardless of reference numerals, and overlapping descriptions thereof will be omitted.

In the present specification, wt% may be replaced by parts by weight.

According to one embodiment of the present invention, an epoxy resin composition comprising an epoxy compound including a mesogen structure, a curing agent, and an inorganic filler is provided. Here, mesogen (mesogen) is a basic unit of a liquid crystal (liquid crystal), and includes a rigid (rigid) structure. Mesogen may include, for example, a rigid structure such as biphenyl.

The epoxy resin composition according to an embodiment of the present invention may include 1wt% to 40wt%, preferably 3wt% to 35wt%, more preferably 5wt% to 30wt% of the epoxy compound relative to the total epoxy resin composition . When the epoxy compound is 1 wt% or more of the total epoxy resin composition and is contained in 40 wt% or less, adhesion may be good and thickness control may be easy. In this case, 25 to 80 parts by weight of the amorphous epoxy compound may be included relative to 20 to 75 parts by weight of the crystalline epoxy compound. When the crystalline epoxy compound and the amorphous epoxy compound are included in such a ratio, crystallization is easy to increase the thermal conductivity effect, and room temperature stabilization is possible.

Here, the crystalline epoxy compound may be an epoxy compound including a mesogen structure as shown in Formula 1 below.

[Formula 1]

Here, R ¹ to R ¹⁴ may be selected from the group consisting of H, Cl, Br, F, C ₁ to C ₃ alkyl, C ₂ to C ₃ alkene, and C ₂ to C ₃ alkyne, respectively. Here, m, n may be 1, 2, or 3, respectively.

Compounds of Formula 1 include compounds of Formula 2.

[Formula 2]

Formula 2 may be referred to as 4,4'-biphenol ether diglycidyl ether (4,4'-biphenolether diglycidyl ether) or SE-4280. The physical properties of the epoxy compound according to the formula (2) has a melting point of 158 ° C, and the results of ¹ H NMR (CDCL ₃ -d6, ppm) are δ = 8.58 (s, 2H), δ = 8.17-8.19 (d, 4H), δ = 7.99-8.01 (d, 4H), δ = 7.33 (s, 4H), δ = 4.69-4.72 (d, 1H), δ = 4.18-4.22 (m, 1H), δ = 3.36-3.40 (m, 1H), δ = 2.92-2.94 (m, 1H) and δ = 2.74-2.77 (m, 1H). The melting point was measured at a heating rate of 10 ° C / min using a differential scanning calorimeter (DSC Q100 manufactured by TA). NMR was measured by H-NMR after dissolving in CDCL ₃ -d6.

The amorphous epoxy compound may be a conventional amorphous epoxy compound having two or more epoxy groups in the molecule.

The amorphous epoxy compound is, for example, bisphenol A, bisphenol F, 3,3 ', 5,5'-tetramethyl-4,4'-dihydroxydiphenylmethane, 4,4'-dihydroxydiphenyl Sulfone, 4,4'-dihydroxydiphenylsulfide, 4,4'-dihydroxydiphenylketone, fluorenebisphenol, 4,4'-biphenol, 3,3 ', 5,5'-tetra Methyl-4,4'-dihydroxybiphenyl, 2,2'-biphenol, resorcin, catechol, t-butylcatechol, hydroquinone, t-butylhydroquinone, 1,2-dihydroxynaphthalene, 1 , 3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydride Hydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,4-dihydroxynaphthalene, 2,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2, 8-dihydroxynaphthalene, allylates or polyallyliates of the dihydroxynaphthalene, allylated bisphenol A, allylated Bivalent phenols such as bisphenol F and allylated phenol novolac, or phenol novolac, bisphenol A novolac, o-cresol novolak, m-cresol novolak, p-cresol novolak, xylenol novolak, poly-p -Hydroxystyrene, tris- (4-hydroxyphenyl) methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, fluoroglycinol, pyrogallol, t-butylpyrogalol, Allylated pyrogallol, polyallylation pyrogallol, 1,2,4-benzenetriol, 2,3,4-trihydroxybenzophenone, phenol aralkyl resin, naphthol aralkyl resin, dicyclopentadiene resin, etc. It may be a glycidyl etherified product derived from one of trivalent or higher phenols, halogenated bisphenols such as tetrabromobisphenol A, and mixtures selected from them.

An example of the bisphenol A-type epoxy compound is as shown in Chemical Formula 3.

[Formula 3]

Here, n is an integer of 1 or more.

One example of the bisphenol F-type epoxy compound is as shown in Chemical Formula 4.

[Formula 4]

The epoxy resin composition according to an embodiment of the present invention may include a curing agent. 0.5 wt% to 30 wt%, preferably 1 wt% to 20 wt%, more preferably 1.5 wt% to 5 wt% of curing agent may be included relative to the total epoxy resin composition. When the curing agent is contained in 0.5wt% to 30wt% of the total epoxy resin composition, adhesion is good, and thickness control may be easy. The epoxy resin composition may include at least one of an amine curing agent, a phenol curing agent, an acid anhydride curing agent, a polymercaptan curing agent, a polyaminoamide curing agent, an isocyanate curing agent, and a block isocyanate curing agent.

The amine-based curing agent may be, for example, 4, 4'-diamino diphenyl sulfone. The following Chemical Formula 5 is an example of diaminodiphenylsulfone.

[Formula 5]

Other examples of the amine curing agent may be aliphatic amines, polyether polyamines, alicyclic amines, aromatic amines, and the like, and aliphatic amines include ethylenediamine, 1,3-diaminopropane, 1,4-diaminopropane, and hexa Methylenediamine, 2,5-dimethylhexamethylenediamine, trimethylhexamethylenediamine, diethylenetriamine, iminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, And N-hydroxyethyl ethylenediamine, tetra (hydroxyethyl) ethylenediamine, and the like. The polyether polyamines may be one of triethylene glycol diamine, tetraethylene glycol diamine, diethylene glycol bis (propylamine), polyoxypropylene diamine, polyoxypropylene triamine, and mixtures selected from them. Examples of the alicyclic amines include isophorone diamine, metasendiamine, N-aminoethyl piperazine, bis (4-amino-3-methyldicyclohexyl) methane, bis (aminomethyl) cyclohexane, and 3,9-bis (3 -Aminopropyl) 2,4,8,10-tetraoxaspiro (5,5) undecane, norbornenediamine, and the like. As aromatic amines, tetrachloro-p-xylenediamine, m-xylenediamine, p-xylenediamine, m-phenylenediamine, o-phenylenediamine, p-phenylenediamine, 2,4-diaminoanisole, 2 , 4-Toluenediamine, 2,4-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 4,4'-diamino-1,2-diphenylethane, 2,4-diaminodi Phenylsulfone, m-aminophenol, m-aminobenzylamine, benzyldimethylamine, 2-dimethylaminomethyl) phenol, triethanolamine, methylbenzylamine, α- (m-aminophenyl) ethylamine, α- (p-amino Phenyl) ethylamine, diaminodiethyldimethyldiphenylmethane, α, α′-bis (4-aminophenyl) -p-diisopropylbenzene and mixtures selected from them.

The phenolic curing agent is, for example, bisphenol A, bisphenol F, 4,4'-dihydroxydiphenylmethane, 4,4'-dihydroxydiphenyl ether, 1,4-bis (4-hydroxyphenoxy ) Benzene, 1,3-bis (4-hydroxyphenoxy) benzene, 4,4'-dihydroxydiphenylsulfide, 4,4'-dihydroxydiphenylketone, 4,4'-dihydride Hydroxydiphenylsulfone, 4,4'-dihydroxydiphenyl ester, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 10- (2,5-dihydroxyphenyl ) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, phenol novolak, bisphenol A novolak, o-cresol novolak, m-cresol novolak, p-cresol novolak, xylenol novolak , Poly-p-hydroxystyrene, hydroquinone, resorcin, catechol, t-butylcatechol, t-butylhydroquinone, fluoroglycinol, pyrogallol, t-butylpyrogalol, allylated pyrogallol, polyallyl Huapirogalol, 1,2,4-benzenetriol, 2,3,4-trihydroxybenzophenone, 1,2-dihydroxynaphthalene, 1,3-di Droxinaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2 , 3-dihydroxynaphthalene, 2,4-dihydroxynaphthalene, 2,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2,8-dihydride Roxynaphthalene, allyl or polyallyl of the dihydroxynaphthalene, bisphenol allylate A, bisphenol allylate F, allyl phenol novolac, allyl pyrogallol and mixtures selected from them.

Acid anhydride-based curing agents include, for example, dodecenyl anhydrous succinic acid, polyadipic acid anhydride, polyazelinic acid anhydride, polysevacinic acid anhydride, poly (ethyl octadecanoic acid) anhydride, poly (phenylhexadecane diacid) anhydride, methyl tetrahydro Phthalic anhydride, methyl hexahydro anhydride phthalic acid, hexahydro anhydride phthalic anhydride, methyl hymic anhydride, tetrahydro anhydride phthalic acid, trialkyltetrahydro anhydride phthalic acid, methylcyclohexene dicarboxylic anhydride, methylcyclohexene tetracarboxylic anhydride, phthalic anhydride, Trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic anhydride, ethylene glycol bistrimellitate, hetic anhydride, nadic anhydride, methylnadic anhydride, 5- (2,5-dioxotetrahydro-3 -Furanyl) -3-methyl-3-cyclohexane-1,2-dicarboxylic acid anhydride, 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalenesuccinic dianhydride, 1- Methyl-dicarboxy-1 , 2,3,4-tetrahydro-1-naphthalenesuccinic dianhydride and mixtures selected from them.

The epoxy resin composition according to an embodiment of the present invention may include two or more kinds of curing agents, for example, diaminodiphenylsulfone and dihydroxydiphenyl ester.

The epoxy resin composition according to an embodiment of the present invention may further include a curing accelerator. Curing accelerators include, for example, amine curing accelerators, imidazole curing accelerators, organic phosphine curing accelerators, Lewis acid curing accelerators, and specifically, 1,8-diazabicyclo (5,4,0). Ter-7, triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol and other tertiary amines, 2-methylimidazole, 2-phenylimidazole, 2-phenyl- Imidazoles such as 4-methylimidazole and 2-heptadecylimidazole, organic phosphines such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine, and phenylphosphine, Tetra-substituted phosphonium-tetra-substituted borate, 2-ethyl-4-methylimidazole-tetra, such as tetraphenylphosphonium-tetraphenylborate, tetraphenylphosphonium-ethyltriphenylborate, tetrabutylphosphonium-tetrabutylborate Phenyl borate, N-methyl morpholine te La and the like tetraphenyl boron salts such as borate.

The epoxy resin composition according to an embodiment of the present invention may include an inorganic filler of 30wt% to 98.5wt% with respect to the total epoxy resin composition. When the inorganic filler is included in 30wt% to 98.5wt%, the high thermal conductivity, low thermal expansion and high temperature heat resistance of the epoxy resin composition may be improved. High thermal conductivity, low thermal expansion, and high temperature heat resistance are better as the amount of the inorganic filler added is higher, but is not improved according to the volume fraction, and is improved dramatically from the specific amount added. However, when the addition amount of the inorganic filler is more than 98.5wt%, the viscosity increases and the moldability is weakened.

According to an embodiment of the present invention, the inorganic filler may include aluminum oxide and aluminum nitride. When the inorganic filler includes aluminum oxide and aluminum nitride, it can increase the withstand voltage and thermal conductivity. Aluminum nitride may contain more than 0wt% of the total epoxy resin composition and less than 25wt%. If the aluminum nitride is contained in more than 25wt% of the total epoxy resin composition, the thermal conductivity may be lowered.

Here, 1 to 60 parts by weight of aluminum oxide may be included with respect to 10 parts by weight of aluminum nitride. When aluminum oxide is contained less than 1 part by weight with respect to 10 parts by weight of aluminum nitride, dispersibility is lowered, and when it is contained more than 60 parts by weight, thermal conductivity may be lowered.

According to an embodiment of the present invention, the inorganic filler may further include a boron nitride agglomerate. The boron nitride agglomerate means a mass of plate-like boron nitride. The boron nitride agglomerate may have a density of 0.3 to 0.4 g / cm ³ , a diameter of 25 to 60 μm, and a surface area of 5.5 to 7 μm ² . When the boron nitride agglomerates are included as the inorganic filler, the thermal conductivity in the through plane is increased, so that a high thermal conductivity effect can be obtained compared to plate-like boron nitride or acicular boron nitride. At this time, if the density of the boron nitride agglomerates exceeds 0.4 g / cm ³ or the diameter is larger than 60 μm or the surface area is larger than 7 μm ² , dispersibility may be deteriorated. In addition, when the density of the boron nitride agglomerates is less than 0.3 g / cm ³ , the diameter is less than 25 μm, or the surface area is less than 5.5 μm ² , a high thermal conductivity effect cannot be obtained compared to plate-like boron nitride or acicular boron nitride.

The boron nitride agglomerate may be included in an amount of 20 to 200 parts by weight, preferably 50 to 180 parts by weight, and more preferably 70 to 150 parts by weight with respect to 10 parts by weight of aluminum nitride. If the aluminum nitride and boron nitride agglomerates are outside this ratio, the thermal conductivity may be lowered.

The epoxy resin composition according to an embodiment of the present invention may include a release agent. As a mold release agent, wax, for example, stearic acid, montanic acid, montanic acid ester, phosphoric acid ester, or the like can be used.

The epoxy resin composition according to an embodiment of the present invention may include a catalyst. The catalyst may be included in an amount of 0.1 wt% to 5 wt%, preferably 0.2 wt% to 3 wt%, more preferably 0.3 wt% to 2 wt% relative to the total epoxy resin composition.

The catalyst may include, for example, an imidazole-based additive such as the following Chemical Formula 6.

[Formula 6]

Here, R ¹⁵ to R ¹⁷ may be selected from the group consisting of H, Cl, Br, F, C ₁ to C ₂₀ alkyl, C ₂ to C ₂₀ alkene, and C ₂ to C ₂₀ alkyne, respectively.

The imidazole-based additive of Formula 6 may include Formula 7 below.

[Formula 7]

When the epoxy resin composition according to an embodiment of the present invention includes the catalyst of Chemical Formula 6, adhesion to a metal may be enhanced. As a result, the adhesion between the insulating layer and the circuit pattern made of copper is increased, and the possibility of breakage and disconnection of the circuit pattern is lowered, so that processing of the printed circuit board is facilitated and reliability of the printed circuit board is increased.

The epoxy resin composition according to an embodiment of the present invention may be applied to a printed circuit board. 1 is a cross-sectional view of a printed circuit board according to an embodiment of the present invention.

Referring to FIG. 1, the printed circuit board 100 includes a metal plate 110, an insulating layer 120 and a circuit pattern 130.

The metal plate 110 may be made of copper, aluminum, nickel, gold, platinum, and alloys selected from them.

An insulating layer 120 made of an epoxy resin composition according to an embodiment of the present invention is formed on the metal plate 110.

The circuit pattern 130 is formed on the insulating layer 120. The circuit pattern 130 may be made of metal such as copper and nickel.

The insulating layer 120 insulates the metal plate 110 from the circuit pattern 130.

By curing the epoxy resin composition according to an embodiment of the present invention and using it as an insulating layer, a printed circuit board having excellent heat dissipation performance can be obtained.

Particularly, according to one embodiment of the present invention, an insulating layer including an epoxy resin composition having a thermal conductivity of 11.5 W / Km or more can be obtained. Preferably, an insulating layer including an epoxy resin composition having a thermal conductivity of 13 W / Km or more can be obtained. More preferably, an insulating layer containing an epoxy resin composition having a thermal conductivity of 14 W / Km or more can be obtained.

Hereinafter, examples and comparative examples will be described in more detail.

<Example 1>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 76 wt% of aluminum oxide, 15 wt% of aluminum nitride and 2 wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate, and then pressed at 150 ° C for 1 hour and 30 minutes to obtain the epoxy resin composition of Example 1.

<Example 2>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 11 wt% of aluminum oxide, 70 wt% of boron nitride agglomerate, 10 wt% of aluminum nitride, and 2 wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain the epoxy resin composition of Example 2.

<Example 3>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 11 wt% of aluminum oxide, 75 wt% of boron nitride agglomerate, 5 wt% of aluminum nitride, and 2 wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate, and then pressed at 150 ° C for 1 hour and 30 minutes to obtain the epoxy resin composition of Example 3.

<Comparative Example 1>

2.5 wt% of the crystalline epoxy compound of Formula 2, 2.5 wt% of the bisphenol F-type epoxy compound of Formula 4, and 1.5 wt% of 4, 4'-diaminodiphenylsulfone are dissolved in MEK (Methyl Ethly Ketone) for 20 minutes. , 91.5wt% of aluminum oxide and 2wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain an epoxy resin composition of Comparative Example 1.

<Comparative Example 2>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 91 wt% of aluminum oxide and 2 wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain an epoxy resin composition of Comparative Example 2.

<Comparative Example 3>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 41 wt% of aluminum oxide, 25 wt% of boron nitride agglomerates, 25 wt% of aluminum nitride and 2 wt% of additives of formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain an epoxy resin composition of Comparative Example 3.

<Comparative Example 4>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 11 wt% of aluminum oxide, 10 wt% of boron nitride agglomerate, 70 wt% of aluminum nitride, and 2 wt% of the additive of Formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain an epoxy resin composition of Comparative Example 4.

<Comparative Example 5>

2.5 wt% of crystalline epoxy compound of formula 2, 2.5 wt% of bisphenol F type epoxy compound of formula 4, 1.5 wt% of 4, 4'-diaminodiphenylsulfone, 0.5 wt of 4,4'-dihydroxydiphenyl ester After dissolving% in MEK (Methyl Ethly Ketone) for 20 minutes, 31 wt% of aluminum oxide, 30 wt% of boron nitride agglomerates, 30 wt% of aluminum nitride and 2 wt% of additives of formula 7 were stirred for 2 hours. After the stirring was completed, the solution was coated on a copper plate and pressed at 150 ° C. for 1 hour and 30 minutes to obtain an epoxy resin composition of Comparative Example 4.

<Experimental Example>

The thermal conductivity of the epoxy resin compositions of Examples 1 to 3 and Comparative Examples 1 to 5 was measured by an abnormal heating method using a LFA447 type thermal conductivity meter manufactured by NETZSCH. Table 1 shows the results.

Experiment number Thermal conductivity (W / m.K) Example 1 11.5 Example 2 13.5 Example 3 14.1 Comparative Example 1 7.2 Comparative Example 2 11 Comparative Example 3 8.2 Comparative Example 4 7.5 Comparative Example 5 7.3

In Comparative Example 1, only diaminodiphenylsulfone is used as a curing agent, but in Comparative Example 2, diaminodiphenylsulfone and dihydroxydiphenyl ester are further included, and the thermal conductivity of Comparative Example 2 is higher than that of Comparative Example 1. Is high. Accordingly, it can be seen that the use of diaminodiphenylsulfone and dihydroxydiphenyl ester as a curing agent can improve thermal conductivity.

On the other hand, in Comparative Example 2, only aluminum oxide is used as the inorganic filler, but in Example 1, aluminum oxide and aluminum nitride are further included, and the thermal conductivity of Example 1 is higher than that of Comparative Example 2. Accordingly, it can be seen that the thermal conductivity can be improved by using aluminum oxide and aluminum nitride together as an inorganic filler.

In addition, in Example 1, aluminum oxide and aluminum nitride are used as inorganic fillers, but in Examples 2 to 3, boron nitride agglomerates are further included together with aluminum oxide and aluminum nitride. 3, high thermal conductivity. Accordingly, it can be seen that the thermal conductivity can be improved by using aluminum oxide, aluminum nitride, and boron nitride agglomerates together as an inorganic filler.

However, when Examples 2 to 3 and Comparative Examples 3 to 5 are compared, the thermal conductivity of Examples 2 to 3 is remarkably high even though aluminum oxide, aluminum nitride and boron nitride agglomerates are all used as inorganic fillers. This is due to the content of aluminum oxide, aluminum nitride and boron nitride agglomerates. That is, as in Examples 2 to 3, when the boron nitride agglomerates contain 65 to 80 parts by weight with respect to 1 to 15 parts by weight of aluminum nitride, high thermal conductivity can be obtained.

The epoxy resin composition according to an embodiment of the present invention can be variously applied to not only the insulating layer of the printed circuit board, but also to electronic components requiring heat dissipation and insulation performance. For example, the epoxy resin composition according to an embodiment of the present invention may be implemented as a heat dissipation sheet of an electronic component.

Although described above with reference to preferred embodiments of the present invention, those skilled in the art variously modify and change the present invention without departing from the spirit and scope of the present invention as set forth in the claims below. You can understand that you can.

Claims (7)

Epoxy compound containing mesogen structure,
Hardener comprising diaminodiphenylsulfone, and
Contains inorganic filler,
The epoxy compound has the structure of Formula 1, and the inorganic filler includes a boron nitride agglomerate in which aluminum oxide, aluminum nitride and plate-like boron nitride are agglomerated,
1 to 60 parts by weight of the aluminum oxide is included with respect to 10 parts by weight of the aluminum nitride,
The epoxy resin composition containing 65 to 80 parts by weight of the boron nitride agglomerate relative to 1 to 15 parts by weight of the aluminum nitride:
[Formula 1]

Here, R ¹ to R ¹⁴ may be selected from the group consisting of H, Cl, Br, F, C ₁ to C ₃ alkyl, C ₂ to C ₃ alkene, and C ₂ to C ₃ alkyne, respectively, and m, n are 1, 2 or 3, respectively. According to claim 1,
The epoxy compound is an epoxy resin composition comprising an epoxy compound of formula (2):
[Formula 2]

According to claim 1,
The aluminum nitride is an epoxy resin composition containing more than 0wt% and less than 25wt% of the total epoxy resin composition. According to claim 1,
The boron nitride agglomerate has a density of 0.3 to 0.4g / cm ³ epoxy resin composition. According to claim 4,
The boron nitride agglomerates have a diameter of 25 to 60 μm, and an epoxy resin composition having a surface area of 5.5 to 7 μm ² . delete According to claim 1,
The curing agent further comprises a dihydroxydiphenyl ester epoxy resin composition.

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