Resin composition for sealing electronic device, and electronic device manufactured using same

The resin composition addresses formability and thermal stability issues in semiconductor packages by using an epoxy compound, inorganic filler, and a bis(tetraalkylphosphonium) pyromellitate catalyst, enhancing flowability and thermal stability for effective sealing and heat dissipation.

WO2026014822A1PCT designated stage Publication Date: 2026-01-15DONGWOO FINE CHEM CO LTD
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Patent Information

Application Number
PCT/KR2025/009606
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-07-12
Filing Date
2025-07-04
Publication Date
2026-01-15

AI Technical Summary

Technical Problem

Existing resin compositions for sealing electronic devices face challenges in achieving improved formability, curing properties, and thermal stability, particularly in micro-sized semiconductor packages, with insufficient flow length and heat dissipation.

Method used

A resin composition comprising an epoxy compound, inorganic filler, ascorbic acid or its derivative, and a bis(tetraalkylphosphonium) pyromellitate compound, which includes specific chemical formulations to enhance flowability, moldability, and thermal stability, while maintaining appropriate curing speed and glass transition temperature.

Benefits of technology

The composition provides high fluidity, improved moldability, and increased glass transition temperature, ensuring reliable sealing and heat dissipation for highly integrated semiconductor packages.

✦ Generated by Eureka AI based on patent content.

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Abstract

A resin composition for sealing an electronic device according to embodiments of the present invention comprises an epoxy-based compound, an inorganic filler, ascorbic acid or a derivative thereof, and a catalyst including bis(tetraalkylphosphonium) pyromellitic acid-based compound.
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Description

Resin composition for sealing electronic devices and electronic devices manufactured using the same

[0001] The present invention relates to a resin composition for sealing electronic devices and an electronic device manufactured using the same. More specifically, the present invention relates to a resin composition for sealing electronic devices comprising an epoxy compound and an additive, and an electronic device manufactured using the same.

[0002] An integrated circuit (IC) chip containing a semiconductor device is surface-mounted on a circuit board, for example, using bumps, solder, or a ball grid array (BGA). The semiconductor device may be sealed or packaged on the circuit board using an epoxy molding compound (EMC) series resin.

[0003] Recently, as the integration level of the semiconductor devices increases and their sizes decrease, there is a need to apply a sealing resin composition having improved formability and curing properties.

[0004] For example, after mounting an IC chip on a BGA substrate, the EMC composition can be filled into the gap between the IC chip and the BGA substrate to fix the IC chip.

[0005] As the size of the above gap decreases, an EMC composition with sufficient flow length is required. In addition, the EMC composition may also be required to have heat dissipation properties that can sufficiently dissipate heat generated during the operation of the semiconductor device to the outside.

[0006] In addition, thermal stability needs to be provided from the EMC composition so as to provide sufficient resistance to heat generated from the semiconductor device and stable chip fixation characteristics.

[0007] One object of the present invention is to provide a resin composition for sealing electronic devices having improved formability.

[0008] One object of the present invention is to provide an electronic device manufactured using the resin composition for sealing an electronic device.

[0009] 1. A resin composition for sealing an electronic device, comprising an epoxy compound; an inorganic filler; ascorbic acid or a derivative thereof; and a catalyst including a bis(tetraalkylphosphonium) pyromellitate compound.

[0010] 2. In the above 1, the bis(tetraalkylphosphonium) pyromellitate compound is a resin composition for sealing an electronic device represented by the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] (In the above chemical formula 1, R1 to R4 are each independently a linear alkyl group having C2 to C5 or a branched alkyl group having C3 to C5).

[0014] 3. In the above 1, a resin composition for sealing an electronic device, wherein the bis(tetraalkylphosphonium) pyromellitate compound comprises bis(tetrabutylphosphonium) pyromellitate or bis(tetrapropylphosphonium) pyromellitate.

[0015] 4. A resin composition for sealing an electronic device, wherein the content of the catalyst in the above 1 is 0.01 wt% to 2 wt% of the total weight of the composition.

[0016] 5. A resin composition for sealing an electronic device, wherein the content of the ascorbic acid or its derivative in the above 1 is 0.01 wt% to 2 wt% of the total weight of the composition.

[0017] 6. A resin composition for sealing an electronic device, wherein in the above 1, the ratio of the content of the catalyst to the content of the ascorbic acid or its derivative in the total weight of the composition is 0.1 to 2.

[0018] 7. A resin composition for sealing an electronic device, wherein the epoxy compound in the above 1 comprises a biphenyl epoxy compound and a biphenyl-aralkyl epoxy compound.

[0019] 8. In the above 7, the biphenyl-based epoxy compound is a resin composition for sealing an electronic device represented by the following chemical formula 2:

[0020] [Chemical Formula 2]

[0021]

[0022] (In the above chemical formula 2, R5, R6, R7 and R8 are each independently hydrogen or a C1 to C5 alkyl group).

[0023] 9. In the above 7, the biphenyl-aralkyl epoxy compound is a resin composition for sealing an electronic device represented by the following chemical formula 3:

[0024] [Chemical Formula 3]

[0025]

[0026] (In the above chemical formula 3, R9 and R 10 are each a C1 to C5 alkylene group, and R 11 is hydrogen, or an alkyl group of C1 to C5, and n is an integer from 1 to 10).

[0027] 10. A resin composition for sealing an electronic device, wherein in the above 7, the weight ratio of the biphenyl-aralkyl epoxy compound to the biphenyl-aralkyl epoxy compound among the epoxy compounds is greater than 1 and less than 8.

[0028] 11. A resin composition for sealing an electronic device, wherein the content of the inorganic filler in the above 1 is 70 wt% to 95 wt% of the total weight of the composition.

[0029] 12. A resin composition for sealing an electronic device, further comprising an additive including at least one selected from the group consisting of a stress relaxant, a coupling agent, a colorant, a curing agent, and a release agent in the above 1.

[0030] 13. An electronic device comprising a sealant formed of the resin composition for sealing the electronic device of the above 1.

[0031] 14. An electronic device according to the above 13, further comprising a circuit board and a semiconductor chip mounted on the circuit board, wherein the sealant fills a space between the circuit board and the semiconductor chip.

[0032] The resin composition for electronic device sealing according to exemplary embodiments of the present invention can have a high glass transition temperature while maintaining an appropriate curing speed. Accordingly, the resin composition can provide a sealing material with improved thermal hardness while providing appropriate flowability for micro-molding.

[0033] The resin composition for sealing electronic devices according to embodiments of the present invention can have high fluidity and improved moldability. Accordingly, the flow length of the composition can be increased.

[0034] The above-mentioned resin composition for sealing an electronic device can be used as a sealing resin for a highly integrated semiconductor package, thereby improving the mounting reliability of a micro-sized integrated circuit chip.

[0035] FIG. 1 is a schematic cross-sectional view showing a semiconductor package using a resin composition for sealing an electronic device according to exemplary embodiments.

[0036] According to embodiments of the present invention, a resin composition for sealing an electronic device is provided, which comprises an epoxy compound, an inorganic filler, ascorbic acid or a derivative thereof, and a catalyst. Furthermore, according to embodiments of the present invention, an electronic device using the resin composition for sealing an electronic device is provided.

[0037] <Resin composition for sealing electronic devices>

[0038] A resin composition for sealing an electronic device according to exemplary embodiments (hereinafter, abbreviated as a resin composition) may include an epoxy compound, an inorganic filler, ascorbic acid or a derivative thereof, and a catalyst. In some embodiments, the resin composition may further include an additive.

[0039] The term "resin composition" as used in this application may encompass both cases where the composition directly includes a resin or where the composition is cured to form a resin.

[0040] The term "Ca to Cb" as used in this application refers to the number of carbon atoms in the group being a to b.

[0041] catalyst

[0042] The resin composition according to exemplary embodiments may include a catalyst. The catalyst may include a bis(tetraalkylphosphonium) pyromellitate-based compound. The bis(tetraalkylphosphonium) pyromellitate-based compound may function as a curing accelerator that promotes an epoxy ring-opening reaction between the epoxy-based compound and the curing agent.

[0043] According to exemplary embodiments, the bis(tetraalkylphosphonium) pyromellitate compound may be represented by the following chemical formula 1.

[0044] [Chemical Formula 1]

[0045]

[0046] In the above chemical formula 1, R1 to R4 can each independently be a C2 to C5 linear alkyl group or a C3 to C5 branched alkyl group. The linear or branched alkyl group can be substituted or unsubstituted. In the present specification, "substitution" can mean that at least one of the hydrogens of the hydrocarbon group is substituted with a functional group such as a hydroxyl group, a carboxyl group, an amine group, an amide group, a cyano group, a thiol group, or a sulfonic acid group.

[0047] For example, R1 to R4 can each independently be an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, or a neopentyl group. Preferably, R1 to R4 can be a propyl group or a butyl group.

[0048] The above tetraalkyl phosphonium cation is a monovalent cation, and the pyromellitate anion is a divalent anion. Accordingly, the bis(tetraalkylphosphonium) pyromellitate compound may contain two tetraalkyl phosphonium cations and one pyromellitate anion in stoichiometric amounts.

[0049] According to exemplary embodiments, the bis(tetraalkylphosphonium) pyromellitate compound may include bis(tetrabutylphosphonium) pyromellitate or bis(tetrapropylphosphonium) pyromellitate.

[0050] According to exemplary embodiments, a bis(tetraalkylphosphonium) pyromellitate compound represented by Chemical Formula 1 can be used to maintain an appropriate range of curing speed / curing initiation temperature. Accordingly, improved molding properties and hardness properties can be simultaneously secured in a micro semiconductor package sealing process. In addition, the bis(tetraalkylphosphonium) pyromellitate compound can increase the glass transition temperature of the resin composition.

[0051] For example, in the structure shown in Chemical Formula 1, the pyromellitate anion is -O -The structure and -OH structure can be included together. Accordingly, excessive increase in curing speed due to the bis(tetraalkylphosphonium) pyromellitate compound can be suppressed, thereby maintaining appropriate flowability and moldability of the resin composition.

[0052] In addition, the bis(tetraalkylphosphonium) pyromellitate compound may have a more stable structure than a monophosphonium ionic catalyst. The bis(tetraalkylphosphonium) pyromellitate compound may be a compound in which a tetraalkylphosphonium cation is arranged on both sides of a symmetrical pyromellitate anion. In this case, the glass transition temperature of the resin composition can be increased, thereby improving the thermal stability of the resin composition and the cured product.

[0053] In exemplary embodiments, the content of the catalyst may be 0.01 wt% to 2 wt%, preferably 0.05 wt% to 1.5 wt%, and more preferably 0.1 wt% to 0.5 wt%, based on the total weight of the composition. Within this range, the effects of controlling the curing speed, curing initiation temperature, and glass transition temperature can be practically easily realized.

[0054] ascorbic acid

[0055] The resin composition according to exemplary embodiments may include ascorbic acid or a derivative thereof. Ascorbic acid may be an organic acid represented by the following chemical formula:

[0056] [chemical formula]

[0057]

[0058] The above ascorbic acid may include L-ascorbic acid and D-ascorbic acid. L-ascorbic acid and D-ascorbic acid have an enantiomeric relationship and may act chemically identically or similarly.

[0059] The above derivative of ascorbic acid may include a compound in which any atom contained in ascorbic acid is substituted with a substituent, or in an oxidized or reduced form, within a range that can maintain the properties of ascorbic acid.

[0060] For example, the derivatives of ascorbic acid may include ascorbic acid salts, dehydroascorbic acid, and the like.

[0061] Resin compositions according to exemplary embodiments may include ascorbic acid and / or derivatives of ascorbic acid.

[0062] The above ascorbic acid or its derivative can function as a slip agent to increase the fluidity of the composition. Accordingly, the molding properties of the composition can be improved.

[0063] Additionally, the ascorbic acid or its derivative can act as an antioxidant, thereby preventing oxidation when the composition is exposed to air.

[0064] According to exemplary embodiments, the content of the ascorbic acid or a derivative thereof may be 0.01 wt% to 2 wt%. According to some embodiments, the content of the ascorbic acid or a derivative thereof may be 0.05 wt% to 1 wt%, 0.1 wt% to 0.8 wt%, or 0.15 wt% to 0.5 wt%. Within the above range, the releasability of the composition may be improved, thereby preventing residue from forming on the mold surface. In addition, the molding properties of the composition may be further improved.

[0065] According to exemplary embodiments, the ratio of the content (wt %) of the catalyst to the content (wt %) of the ascorbic acid or a derivative thereof in the total weight of the composition may be from 0.1 to 2. According to some embodiments, the ratio of the content of the catalyst to the content of the ascorbic acid or a derivative thereof in the total weight of the composition may be from 0.3 to 1.8, or from 0.4 to 1.6. Within this range, the curing speed of the composition may be increased while improving the fluidity.

[0066] epoxy compounds

[0067] An epoxy compound can be used to form a base resin or binder resin that provides thermosetting properties to the resin composition. The epoxy compound can be crosslinked or cured to form an electronic device sealant comprising the epoxy resin.

[0068] The above epoxy compound may include a biphenyl epoxy compound and a biphenyl-aralkyl epoxy compound.

[0069] The above biphenyl-based epoxy compound may refer to a compound in which an epoxy group is bonded to both terminals of the para position of the biphenyl group via an ether group. For example, the inclusion of the biphenyl-based epoxy compound may improve the flow properties of the resin composition and enhance the formability.

[0070] According to exemplary embodiments, the biphenyl epoxy compound may be represented by the following chemical formula 2.

[0071] [Chemical Formula 2]

[0072]

[0073] In the above chemical formula 2, R5, R6, R7 and R8 can each independently be hydrogen or a C1 to C5 alkyl group.

[0074] In one embodiment, in chemical formula 2, R5, R6, R7, and R8 can each be a methyl group.

[0075] The above biphenyl-aralkyl epoxy compound may refer to an epoxy compound in which an alkylene group is bonded to each of the two terminals at the para position of the biphenyl group.

[0076] According to exemplary embodiments, the biphenyl-aralkyl epoxy compound may be represented by the following chemical formula 3.

[0077] [Chemical Formula 3]

[0078]

[0079] In the above chemical formula 3, R9 and R 10 are each a C1 to C5 alkylene group, and R 11 may be hydrogen, or an alkyl group having C1 to C5 carbon atoms.

[0080] n is an integer from 1 to 50, preferably from 1 to 30, from 1 to 20, or from 1 to 10.

[0081] In one embodiment, R9 and R 10 are each methylene groups (-CH2-), and R 11 It could be hydrogen.

[0082] According to exemplary embodiments, the weight ratio of the biphenyl-based compound to the biphenyl-aralkyl-based epoxy compound may be greater than 1 and less than or equal to 8. According to some embodiments, the weight ratio of the biphenyl-based compound to the biphenyl-aralkyl-based epoxy compound may be from 1.4 to 4.5, from 1.5 to 4, or from 2 to 4.

[0083] When the above weight ratio is 1 or less, the flow length of the resin composition may be reduced, and an electronic device sealant having a uniform thickness and heat dissipation properties may not be formed.

[0084] If the above weight ratio exceeds 8, the composition may not have a sufficient glass transition temperature. Accordingly, sufficient heat resistance may not be provided in the high-temperature environment occurring in the semiconductor package.

[0085] The epoxy compound may be present in an amount of 1 wt% to 15 wt%, preferably 1 wt% to 10 wt%, and more preferably 3 wt% to 7 wt% of the total weight of the resin composition (e.g., solid content). Within the above range, the resin composition can be sufficiently cured while maintaining appropriate flowability and molding properties.

[0086] In one embodiment, the epoxy compound may not include a bisphenol epoxy compound (e.g., bisphenol F type resin). Accordingly, an increase in flow length through the introduction of the biphenyl epoxy compound can be sufficiently easily implemented.

[0087] Weapon filler

[0088] The above resin composition may include an inorganic filler. The heat dissipation properties of the semiconductor package can be effectively implemented through the sealant by the inorganic filler.

[0089] For example, the inorganic filler may include fused silica, crystalline silica, calcium carbonate, magnesium carbonate, alumina, magnesia, clay, talc, calcium silicate, titanium oxide, antimony oxide, glass fiber, etc. These may be used alone or in combination of two or more.

[0090] The above inorganic filler may include alumina particles in consideration of heat dissipation properties. The thermal conductivity of alumina may be 25 W / m·K to 30 W / m·K, and the thermal conductivity of the composition may be easily increased. The alumina particles may be a mixture of two or more types of alumina particles having different average particle diameters (e.g., D50).

[0091] The alumina particles may include a mixture of small-sized alumina particles having a D50 in the range of 0.1 μm to 1.5 μm and large-sized alumina particles having a D50 in the range of 1 μm to 5 μm. The D50 of the large-sized alumina particles may be greater than the D50 of the small-sized alumina particles.

[0092] The term "average particle size (D50)" used in this application may refer to the median particle size corresponding to 50% in a cumulative distribution (by number) in which the particles are arranged in order of size.

[0093] The above-mentioned inorganic filler may be included in the largest amount in the resin composition to enhance the heat dissipation effect. For example, the content of the above-mentioned inorganic filler may be 70 wt% to 95 wt%, preferably 80 wt% to 95 wt%, and more preferably 87 wt% to 93 wt% of the solid content of the resin composition.

[0094] additives

[0095] The above resin composition may optionally include additives in consideration of molding properties, adhesion properties, etc.

[0096] The above additive may include a stress reliever. The stress reliever may include an additive that can improve releasability by alleviating the stress generated when a resin composition is poured into a mold, etc., molded, cured, and then separated from the mold.

[0097] For example, the stress reliever may include a silicone-based compound. Examples of the silicone-based compound may include silicone oil, silicone elastomer, silicone powder, silicone resin, and the like. Preferably, the stress reliever may include silicone oil.

[0098] In exemplary embodiments, the silicone oil may include an epoxy-modified polysiloxane compound. For example, the silicone oil may include a polysiloxane compound represented by the following chemical formula 4.

[0099] [Chemical Formula 4]

[0100]

[0101] In the above chemical formula 4, R a Inland R j are each independently a linear alkyl group having C1 to C4, A may be a non-reactive functional group, and B may be a reactive functional group including an epoxy group. In addition, n, m, and p may each independently be an integer from 1 to 50.

[0102] The above R a Inland R j Each of A and B may be a methyl group, A may be a polyether group, and B may be a glycidyl ether group.

[0103] In exemplary embodiments, the average particle diameter (D50) of the silicon powder may be 1 μm to 10 μm. In some embodiments, the average particle diameter of the silicon powder may be 2 μm to 5 μm.

[0104] In exemplary embodiments, the viscosity of the silicone compound is 2000 mm 2 / s to 5000 mm 2 / s, preferably 2400 mm 2 / s to 4000 mm 2 / s may be. Within the above range, the stress relaxant can further improve the release properties of the cured product of the resin composition.

[0105] In exemplary embodiments, the content of the stress reliever may be 0.01 wt% to 1 wt%, preferably 0.05 wt% to 0.5 wt%, based on the total weight of the composition. Within this range, the stress reliever can further alleviate stress when the cured product of the resin composition is separated from the mold. Accordingly, deformation of the cured product can be prevented, and the cured product can be more easily separated from the mold.

[0106] The above additive may include a curing agent as a component that increases the hardness of the sealant by crosslinking through an epoxy ring-opening reaction with the above epoxy compound.

[0107] According to exemplary embodiments, the curing agent may include a resin containing a hydroxyl group, and may include a phenolic resin or a novolac resin.

[0108] For example, the curing agent may include a phenol novolac-type phenol resin, a multifunctional phenol resin, a xylok-type phenol resin, a cresol novolac-type phenol resin, a naphthol-type phenol resin, a terpene-type phenol resin, a dicyclopentadiene-based phenol resin, a novolac-type phenol resin synthesized from bisphenol A and resol, etc. These may be used alone or in combination of two or more.

[0109] In one embodiment, the curing agent may include a repeating unit represented by the following chemical formula 5.

[0110] [Chemical Formula 5]

[0111]

[0112] In some embodiments, the curing agent may further include an acid anhydride including maleic anhydride or phthalic anhydride, an aromatic amine such as metaphenylenediamine, diaminodiphenylmethane, or diaminodiphenylsulfone.

[0113] The content of the above-mentioned curing agent may be 1 wt% to 15 wt%, preferably 1 wt% to 10 wt%, and more preferably 3 wt% to 8 wt% of the solid content of the above-mentioned resin composition. Within the above range, sufficient cross-linking properties with the above-mentioned epoxy resin can be secured while maintaining appropriate flowability and molding properties.

[0114] In one embodiment, the additive may include a coupling agent. For example, the coupling agent may improve the interfacial compatibility between the resin component and the inorganic filler.

[0115] The coupling agent may include a silane coupling agent. For example, the coupling agent may include an epoxy silane compound, an amino silane compound, an alkyl silane compound, etc.

[0116] In one embodiment, the additive may include a release agent. For example, the release agent may promote mold separation. The release agent may include a wax such as a paraffin wax or an ester wax, a fatty acid compound such as a higher fatty acid, a higher fatty acid metal salt, a natural fatty acid, or a natural fatty acid metal salt.

[0117] In one embodiment, the additive may include a colorant to impart color to the sealant. For example, the colorant may include carbon black or the like.

[0118] The content of the above additive can be appropriately adjusted within a range that does not inhibit the action of the above-described epoxy compound, ascorbic acid or its derivative, catalyst, and inorganic filler.

[0119] For example, the content of the additive may be 0.01 wt% to 2 wt%, preferably 0.05 wt% to 1.5 wt%, and more preferably 0.1 wt% to 1 wt% of the solid content of the resin composition.

[0120] Electronic Devices

[0121] FIG. 1 is a schematic cross-sectional view illustrating a semiconductor package using a resin composition for sealing an electronic device according to exemplary embodiments. For example, the electronic device may include a semiconductor package.

[0122] Referring to FIG. 1, the electronic device includes a circuit board (100) and a semiconductor chip (130), and may include a sealant (150) that fills and bonds between the semiconductor chip (130) and the circuit board (100).

[0123] The circuit board (100) may include, for example, a rigid printed circuit board (rigid PCB), a main board, an interposer, etc. The circuit board (100) may include internal wiring (110).

[0124] A semiconductor chip (130) can be mounted on a circuit board (100) through surface mount technology (SMT). The semiconductor chip (130) can include an AP chip, a logic device, a memory device, etc.

[0125] A semiconductor chip (130) can be electrically connected to internal wiring of a circuit board (100) through a conductive intermediary structure (120). The conductive intermediary structure (120) can include solder, bumps, ball grid array (BGA), etc.

[0126] The sealant (150) is formed using a resin composition according to exemplary embodiments, fills the space between the semiconductor chip (130) and the circuit board (100), and can bond the semiconductor chip (130) and the circuit board (100) to each other. For example, the sealant can be formed by curing and molding the resin composition through injection molding, casting molding, or the like.

[0127] Hereinafter, embodiments of the present invention will be further described with reference to specific experimental examples. The examples and comparative examples included in the experimental examples are merely illustrative of the present invention and do not limit the scope of the appended claims. It will be apparent to those skilled in the art that various modifications and variations of the examples are possible within the scope and technical spirit of the present invention, and it is also natural that such modifications and variations fall within the scope of the appended claims.

[0128] Examples and Comparative Examples

[0129] The ingredients shown in Table 1 below were ground and mixed for 5 minutes using a super mixer according to the contents in Table 1. The mixture was extruded in a twin-screw extruder with a cylinder inner diameter of 65 mm at a rotation speed of 60 rpm to 200 rpm, 100 o A resin composition was prepared by melting and kneading at a temperature of C. Thereafter, a pulverized epoxy resin composition was prepared through a cooling and pulverizing process. The content of each component listed in Table 1 represents the weight % of the total weight of the composition.

[0130] Example Comparative Example 12345612345A-13.0182.9662.8962.8962.7583.0523.0692.9662.9662.9662.9662.966A-21.2931.2711.2411.2411.1821.3081.3151.2711.2711.2711.271B-10.2370.2330.228- 0.2170.2400.2410.2330.2330.233-B-2---0.228--0.2410.233---C-10.1500.3000.5000 .5000.9000.050----0.300C-2-------0.300---C-3--------0.300--C-4---------0.300 -D9090909090909090909090E4.1624.0913.9953.9953.8044.2104.2344.0914.0914.0914 .091F0.3000.3000.3000.3000.3000.3000.3000.3000.3000.3000.300G0.2700.2700.270 0.2700.2700.2700.2700.2700.2700.2700.270H0.2700.2700.2700.2700.2700.2700.270 0.2700.2700.2700.270I0.3000.3000.3000.3000.3000.3000.3000.3000.3000.3000.300

[0131] (A) Epoxy compound A-1: ​​Biphenyl epoxy compound (YX-4000H, Mitsubishi Chemical, chemical formula 2-1 structure)

[0132] [Chemical Formula 2-1]

[0133]

[0134] A-2: Biphenyl-aralkyl epoxy compound (NC3000, Nippon Gunpowder, chemical formula 3-1 structure)

[0135] [Chemical Formula 3-1]

[0136]

[0137] (B) Catalyst

[0138] B-1: Bis(tetra-n-butylphosphonium)pyromellitate (Hokko)

[0139] B-2: Bis(tetra-n-ethylphosphonium)pyromellitate

[0140] B-2 was synthesized by the following method.

[0141] Synthesis Example B-2

[0142] After adding 55 g of pyromellitic anhydride to 1 L of water, 1026 g of an 8 wt% aqueous solution of tetraethylphosphonium hydroxide was slowly added to the solution, and the mixture was heated and stirred at 70°C for 2 hours. Impurities in the precipitated crystals were removed to obtain 164 g (yield 85%) of bis(tetra-n-ethylphosphonium)pyromellitic acid.

[0143] (C) organic compounds

[0144] C-1: L-ascorbic acid (Sigma Aldrich)

[0145] C-2: Oleylamine (Sigma-Aldrich)

[0146] C-3: Pamoic Acid (Sigma-Aldrich) of the following chemical formula 6

[0147] [Chemical Formula 6]

[0148]

[0149] C-4: Barbituric acid (Sigma-Aldrich)

[0150] (D) Inorganic filler: Alumina particles (DAW03, Denka Korea, D50: 3㎛)

[0151] (E) Curing agent: Biphenyl aralkyl type compound (MEH-7851SS, Meiwa, containing repeating units of chemical formula 5)

[0152] (F) Lithium-ion battery: wax (Licowax, Clariant)

[0153] (G) Coupling agent: N-phenyl-γ-aminopropyltrimethoxy silane (Y9669, Momentive)

[0154] (H) Stress reliever: Silicone oil (SF-8421EG, DOWSIL)

[0155] (I) Colorant: Carbon black (MA-600, Mitsubishi)

[0156] Experimental example

[0157] The experiment was conducted according to the following method, and the measurement and evaluation results are shown in Table 2 below.

[0158] (1) Spiral flow assessment (liquidity assessment)

[0159] Using a spiral flow evaluation mold manufactured based on the EMMI-1-66 standard, the molding temperature was 175℃, and 70 kgf / cm 2 The flow length of the resin compositions of the examples and comparative examples was measured for 120 seconds using a transfer molding press. If the measured flow length was 55 inches or more, it was evaluated as good, and if it was less than 55 inches, it was evaluated as poor.

[0160] (2) Evaluation of dysmorphism

[0161] After the spiral flow evaluation of (1) above, the sample was removed and the occurrence of residue in the mold was observed and evaluated according to the following criteria.

[0162] <Evaluation Criteria>

[0163] O: No residue

[0164] △: Local residue occurrence

[0165] X: Residue occurs throughout the mold

[0166] Example Comparative Example 1 2 3 4 5 6 1 2 3 4 5 Fluidity (inch) 5 5 5 8 6 2 5 1 5 5 5 1 4 8 4 7 4 1 3 9 0 Good Good Good Good Good Good Bad Bad Bad Bad Bad Formability OOOOOO△O△△△

[0167] Referring to Table 1, the compositions of the examples exhibited improved fluidity and enhanced molding properties. Additionally, in the examples, the compositions did not remain on the mold surface, and the releasability of the compositions was also improved.

[0168] In Example 5, which contained an excessive amount of ascorbic acid, the heteromorphism was somewhat reduced compared to other examples.

[0169] In Comparative Examples 1 to 4 that did not contain ascorbic acid, the fluidity of the composition was reduced. In Comparative Example 5 that did not contain a catalyst, the curing speed of the composition was reduced, resulting in reduced fluidity and release properties.

Claims

1. Epoxy compound; Weapon filler; ascorbic acid or a derivative thereof; and A resin composition for sealing an electronic device, comprising a catalyst comprising a bis(tetraalkylphosphonium) pyromellitate compound.

2. In the first paragraph, the bis(tetraalkylphosphonium) pyromellitate compound is a resin composition for sealing an electronic device represented by the following chemical formula 1. [Chemical Formula 1] (In the above chemical formula 1, R1 to R4 are each independently a linear alkyl group having C2 to C5 or a branched alkyl group having C3 to C5).

3. A resin composition for sealing an electronic device, wherein the bis(tetraalkylphosphonium) pyromellitate compound in the first paragraph comprises bis(tetrabutylphosphonium) pyromellitate or bis(tetrapropylphosphonium) pyromellitate.

4. A resin composition for sealing an electronic device, wherein the content of the catalyst in the first paragraph is 0.01 wt% to 2 wt% of the total weight of the composition.

5. A resin composition for sealing an electronic device, wherein the content of the ascorbic acid or its derivative in the first paragraph is 0.01 wt% to 2 wt% of the total weight of the composition.

6. A resin composition for sealing an electronic device, wherein the ratio of the content of the catalyst to the content of the ascorbic acid or its derivative in the total weight of the composition is 0.1 to 2.

7. A resin composition for sealing an electronic device, wherein the epoxy compound in the first paragraph comprises a biphenyl epoxy compound and a biphenyl-aralkyl epoxy compound.

8. In the 7th paragraph, the biphenyl-based epoxy compound is a resin composition for sealing an electronic device represented by the following chemical formula 2: [Chemical Formula 2] (In the above chemical formula 2, R5, R6, R7 and R8 are each independently hydrogen or a C1 to C5 alkyl group).

9. In the 7th paragraph, the biphenyl-aralkyl epoxy compound is a resin composition for sealing an electronic device represented by the following chemical formula 3: [Chemical Formula 3] (In the above chemical formula 3, R9 and R 10 are each a C1 to C5 alkylene group, and R 11 is hydrogen, or an alkyl group of C1 to C5, and n is an integer from 1 to 10).

10. A resin composition for sealing an electronic device, wherein, in the 7th paragraph, the weight ratio of the biphenyl-aralkyl epoxy compound to the biphenyl-aralkyl epoxy compound among the epoxy compounds is greater than 1 and less than or equal to 8.

11. A resin composition for sealing an electronic device, wherein the content of the inorganic filler in the first paragraph is 70 wt% to 95 wt% of the total weight of the composition.

12. A resin composition for sealing an electronic device, further comprising an additive comprising at least one selected from the group consisting of a stress relaxant, a coupling agent, a colorant, a curing agent, and a release agent, in the first paragraph.

13. An electronic device comprising a sealant formed from the resin composition for sealing an electronic device of claim 1.

14. In the 13th paragraph, further comprising a circuit board and a semiconductor chip mounted on the circuit board, An electronic device in which the sealant fills the space between the circuit board and the semiconductor chip.

Citation Information

Patent Citations

  • Phosphonium compound, epoxy resin composition comprising the same and semiconductor device prepared from using the same

    KR101768305B1

  • Epoxy resin composition for encapsulating semiconductor device and semiconductor device prepared from using the same

    KR101835937B1

  • Curable epoxy-based compositions

    KR1020010034183A

  • A conjugate, composition and method for noncovalent antibody catenation that increases antigen-binding avidity of an antibody in proportion to the density of a target antigen

    KR1020240015006A

  • Built-up Safe Scaffold for High Place Work

    KR102229567B1