CN115466486A - Epoxy resin composition and preparation method thereof - Google Patents
Epoxy resin composition and preparation method thereof Download PDFInfo
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- CN115466486A CN115466486A CN202210798377.0A CN202210798377A CN115466486A CN 115466486 A CN115466486 A CN 115466486A CN 202210798377 A CN202210798377 A CN 202210798377A CN 115466486 A CN115466486 A CN 115466486A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/16—Solid spheres
- C08K7/18—Solid spheres inorganic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
The invention relates to the field of C08L63/00, in particular to an epoxy resin composition and a preparation method thereof, and the epoxy resin composition is provided by adopting 4-14 parts of epoxy resin, 2-9 parts of curing agent, 78-92 parts of inorganic filler, 0.05-1 part of catalyst and 0-6 parts of additive. The epoxy resin composition provided by the invention can be used for improving the glass transition temperature (Tg) of the packaging material to meet the requirement of high-temperature application, and simultaneously, the internal stress of a device is reduced by adding a novel structural resin or adding a flexible resin, so that the delamination resistance and the reliability are improved, and the epoxy resin composition is effectively applied to the field of electronic packaging.
Description
Technical Field
The invention relates to the field of C08L63/00, in particular to an epoxy resin composition and a preparation method thereof.
Background
The third generation semiconductor SiC device can obviously reduce the power loss of motor control systems of pure electric vehicles and hybrid electric vehicles, and realize low power consumption; the power device produced by the SiC process has lower on-resistance, smaller chip size and higher working frequency, and can tolerate higher environmental temperature; the high integration of power modules also places new demands on the stress of the packaging material.
Chinese patent CN109486100A discloses an epoxy resin composition for electronic packaging and a preparation method thereof, which uses epoxy resin, phenolic resin, curing accelerator, inorganic filler and the like as main raw materials, so that the provided epoxy resin composition for electronic packaging has low warpage, high fluidity and high bonding performance, but can not meet the use requirement under the condition of high temperature; chinese patent CN 10124173B discloses an epoxy resin electronic packaging material and an electronic component encapsulated by the same, which uses epoxy resin, nano silica, curing agent, inorganic filler and auxiliary agent as raw materials to improve the heat resistance and water absorption resistance of the epoxy resin electronic packaging material, but fails to effectively reduce the internal stress of the packaging material, and the delamination resistance and reliability need to be further improved.
Therefore, in order to solve the above problems, the present invention provides an epoxy resin composition and a method for preparing the same, which can improve the glass transition temperature (Tg) of an encapsulating material to meet high temperature applications by optimizing the formulation and process, and reduce the flexural modulus of the material by adding a novel structural resin or adding a flexible resin to reduce the internal stress of a device, thereby improving delamination resistance and reliability.
Disclosure of Invention
The invention provides an epoxy resin composition, which at least comprises the following raw materials in parts by weight: 4-14 parts of epoxy resin, 2-9 parts of curing agent, 78-92 parts of inorganic filler, 0.05-1 part of catalyst and 0-6 parts of additive.
As a preferred embodiment, the epoxy resin comprises at least two epoxy groups; preferably, the epoxy resin is selected from the group consisting of multifunctional structures, novel multifunctional structures, polyaromatic ring structures, o-cresol structure epoxy resins, and combinations thereof.
Preferably, the epoxy resin comprises one or a combination of the following formulas (I), (II), (III), (IV), (V) and (VI):
a compound of formula (I):
formula (II):
formula (III):
formula (IV):
formula (V):
formula (VI):
as a preferable technical scheme, n1-n6 in the formula (I), the formula (II), the formula (III), the formula (IV) and the formula (V) are respectively 1, 2 or 3.
Preferably, the epoxy equivalent of the epoxy resin shown in formula (I), formula (II), formula (III), formula (IV) and formula (V) is 160-300g/eq;
preferably, the epoxy resin has an epoxy equivalent weight of 163 to 175g/eq of formula (I); the epoxy equivalent of the epoxy resin formula (II) is 200-220g/eq; the epoxy equivalent of the epoxy resin formula (III) is 270-284g/eq; the epoxy equivalent of the epoxy resin formula (IV) is 194-204g/eq; the epoxy equivalent of the epoxy resin formula (V) is 250-280g/eq; the epoxy equivalent of the epoxy resin formula (VI) is 187-197g/eq; the epoxy resin formula (I), the epoxy resin formula (II), the epoxy resin formula (III), the epoxy resin formula (IV), the epoxy resin formula (V) and the epoxy resin formula (VI) are from Shanghai Dai semiconductor materials GmbH.
Based on the system, the epoxy resin with the specific structure (I), the formula (II), the formula (III), the formula (IV) and the formula (V) is adopted, so that the glass transition temperature of the epoxy resin composition is improved, and the characteristics of good heat resistance and flexibility of the product are simultaneously achieved. In addition, the inventor finds that the introduction of the epoxy resin with the specific structure is beneficial to reducing the flexural modulus of the epoxy resin composition, absorbing thermal stress, improving the delamination resistance and reliability and ensuring the subsequent practical application effect in the research process. The reason the inventor analyzes may be: the epoxy groups in the multifunctional epoxy resin formula (I) and the novel epoxy resin formula (II) have high density, and react with a curing agent in a system to obtain a high crosslinking density product, so that the glass transition temperature (Tg) is effectively increased; meanwhile, the polyaromatic ring type epoxy resin formula (III) and the dicyclopentadiene epoxy resin formula (V) are favorable for reducing flexural modulus and absorbing thermal stress after being added due to special molecular structures.
As a preferable technical solution, the curing agent is a phenolic resin curing agent.
Preferably, the phenolic resin curing agent is selected from a multifunctional group structure, a polyaromatic ring structure, a phenolic resin and a combination thereof, wherein the multifunctional group structure is represented by formula (VII), the polyaromatic ring structure is represented by formula (VIII), and the phenolic resin is represented by formula (IX):
formula (VII):
formula (VIII):
formula (IX):
preferably, n7-n9 in the formula (VII), the formula (VIII) and the formula (IX) are respectively 1, 2 or 3.
Preferably, the phenolic resin curing agent has a hydroxyl equivalent weight of 90-210g/eq in the formula (VII), the formula (VIII) and the formula (IX);
preferably, the phenolic resin curing agent has a hydroxyl equivalent weight of 96-106g/eq; the hydroxyl equivalent weight of the phenolic resin curing agent formula (VIII) is 190-210g/eq; the phenolic resin curing agent has the formula (IX) hydroxyl equivalent of 104-108g/eq; the phenolic resin curing agent has the formula (VII), the formula (VIII) and the formula (IX) which are from Shanghai Dai semiconductor materials Co.
Based on the epoxy resin in the system, the multifunctional junction type phenolic resin curing agent is adopted, and the hydroxyl group density in the curing agent is high, so that the cured epoxy resin composition has high crosslinking density, the glass transition temperature of the epoxy resin composition is effectively improved, and the epoxy resin composition has low viscosity and is easy to produce and process. And the adoption of the polyaromatic ring type phenolic resin curing agent helps to reduce the flexural modulus, so that the provided epoxy resin composition has excellent flexibility and adhesive property.
As a preferable technical scheme, the mass ratio of the epoxy resin to the inorganic filler is (4-14): (80-88); preferably, the inorganic filler is selected from the group consisting of crystalline silica, angular silica, spherical silica, alumina, and combinations thereof. Preferably, the inorganic filler is spherical silica; preferably, the particle size of the spherical silicon dioxide is less than or equal to 75um; the spherical silica has a median particle diameter (D50) of 20um and a Specific Surface Area (SSA) of 2.5m 2 Perg, purchased from Ribes New materials, inc.
As a preferred technical scheme, the catalyst is selected from imidazoles, triphenylphosphine-benzoquinone adducts and combinations thereof; preferably, the catalyst is selected from the group consisting of triphenylphosphine, triphenylphosphine-benzoquinone adducts, and combinations thereof.
As a preferred technical solution, the additive is selected from one or more of the following: coupling agents, colorants, mold release agents; preferably, the coupling agent is selected from the group consisting of 3- (glycidoxypropyl) trimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane and combinations thereof; preferably, the coupling agent is a combination of 3- (glycidoxypropyl) trimethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-aminopropyltrimethoxysilane.
Preferably, the colorant is carbon black; preferably, the release agent is natural wax or synthetic wax; preferably, the release agent is carnauba wax.
As a preferred technical solution, the epoxy resin composition has one or more of the following properties:
A. curing at 175 + -2 deg.C for 90 seconds with a spiral flow length of 25-55 inches;
B. gelation time at 175 + -2 deg.C is 25-55 s;
C. the glass transition temperature is 175-225 ℃ at 175 +/-2 ℃;
D. the flexural modulus is 25MPa or less at 25 ℃.
The invention also provides a preparation method of the epoxy resin composition, which at least comprises the following steps:
(1) Respectively crushing the epoxy resin and the curing agent to obtain powder, subpackaging, sealing and storing at low temperature for later use;
(2) Adding the inorganic filler, the catalyst and the additive into a high-speed stirrer in batches, stirring and mixing, and adding the epoxy resin and the curing agent which are crushed in the step (1) for mixing;
(3) And pouring the uniformly mixed mixture into an extruder for mixing, cooling and crushing to obtain the composite material.
Preferably, the crushing instrument in the step (1) is a resin crusher, and the crushing temperature is less than or equal to 25 ℃;
preferably, the stirring and mixing temperature of the high-speed stirrer in the step (2) is less than or equal to 25 ℃;
preferably, the extruder in the step (3) is a single-screw extruder or a double-screw extruder; preferably, the extrusion temperature of the extruder in the step (3) is 90-120 ℃.
The epoxy resin composition product is sealed and stored in a low-temperature environment; the temperature of the low temperature environment is less than 5 ℃.
The third aspect of the invention provides an application of the epoxy resin composition in electronic packaging.
Advantageous effects
1. The invention provides an epoxy resin composition and a preparation method thereof, wherein the glass transition temperature (Tg) of a packaging material is improved through the design of a formula and the optimization of a process so as to meet the requirement of high-temperature application, and meanwhile, the bending modulus of the material is reduced through adding a novel structural resin or adding a flexible resin so as to reduce the internal stress of a device and improve the delamination resistance and the reliability.
2. Based on the system, the epoxy resins with specific structures (I), (II), (III), (IV) and (V) are introduced into the system, so that the glass transition temperature of the epoxy resin composition is improved, and the product has the characteristics of good heat resistance and flexibility.
3. By introducing the epoxy resin with a specific structure, the invention is beneficial to reducing the flexural modulus of the epoxy resin composition, absorbing the thermal stress, improving the delamination resistance and reliability and ensuring the subsequent practical application effect.
4. Based on the epoxy resin in the system, the multifunctional junction type phenolic resin curing agent is adopted, and the hydroxyl group density in the curing agent is high, so that the cured epoxy resin composition has high crosslinking density, the glass transition temperature of the epoxy resin composition is effectively improved, and the epoxy resin composition has low viscosity and is easy to produce and process.
Detailed Description
Examples
Examples 1-10 of the present invention provide, in one aspect, an epoxy resin composition, the raw materials for which are specifically shown in Table 1.
Embodiments 1 to 10 of the present invention also provide a method for preparing an epoxy resin composition, comprising the steps of:
(1) Respectively crushing the epoxy resin and the curing agent to obtain powder, subpackaging, sealing and storing at low temperature for later use;
(2) Adding inorganic filler, catalyst and additive into a high-speed stirrer in batches, stirring and mixing, and adding the epoxy resin and the curing agent which are crushed in the step (1) for mixing;
(3) And pouring the uniformly mixed mixture into an extruder for mixing, cooling and crushing to obtain the composite material.
The crushing instrument in the step (1) is a resin crusher, and the crushing temperature is 20 ℃;
the stirring and mixing temperature of the high-speed stirrer in the step (2) is 20 ℃;
the extruder in the step (3) is a double-screw extruder; the extrusion temperature of the extruder in the step (3) is 100 ℃.
The epoxy resin composition product is sealed and stored in a low-temperature environment; the temperature of the low temperature environment is 4 ℃.
TABLE 1,
Wherein: the epoxy resin has an epoxy equivalent of 163 to 175g/eq (manufacturer: nippon chemical Co., ltd.: EPPN-501 HY); the epoxy equivalent of the epoxy resin formula (II) is 200-220g/eq (manufacturer: nippon chemical Co., ltd.: NC-3500); the epoxy resin formula (III) has an epoxy equivalent of 270 to 284g/eq (manufacturer: nippon chemical Co., ltd.: NC-3000); the epoxy equivalent of the epoxy resin formula (IV) is 194-204g/eq (manufacturer: changchun artificial resin factory brand: CNE-195 LL); the Epoxy equivalent of the Epoxy resin formula (V) is 250-280g/eq (manufacturer: DIC Epoxy (Malaysia) Sdn. Bhd. Trade name: HP-7200); the epoxy equivalent of the epoxy resin of formula (VI) is 187 to 197g/eq (manufacturer: mitsubishi chemical corporation brand: jER YX 4000).
The phenolic resin curing agent has a hydroxyl equivalent weight of 96-106g/eq (manufacturer: evort Kagaku K.K.: HE 910-09); the hydroxyl equivalent weight of the phenolic resin curing agent formula (VIII) is 190-210g/eq (manufacturer: trade name of Jiansheng Material science and technology Limited in Hunan: BPNH 9781S); the phenolic resin curing agent has a formula (IX) hydroxyl equivalent of 104-108g/eq (manufacturer: shandong Shengquan New Material Co., ltd.: PF 8011).
Comparative example 1
Comparative example 1 of the present invention provides an epoxy resin composition, which was prepared by the same method as examples 1 to 10, with specific reference to Table 1.
Comparative example 2
Comparative example 2 of the present invention provides an epoxy resin composition, which was prepared by the same method as examples 1 to 10, with specific reference to Table 1.
Performance test method
1. The gelation times of examples 1-10 and comparative examples 1-2 were tested with reference to GB/T33316-2016, and the results are shown in Table 2.
2. The spiral flow lengths of examples 1-10 and comparative examples 1-2 were tested with reference to ASTM D3123-09, and the test results are shown in Table 2.
3. The glass transition temperatures of examples 1-10 and comparative examples 1-2 were tested with reference to GB/T22567-2008, and the test results are shown in Table 2.
4. The flexural modulus of examples 1-10 and comparative examples 1-2 were tested in accordance with ASTM 790D-17, and the test results are shown in Table 2.
Claims (10)
1. The epoxy resin composition is characterized by comprising the following raw materials in parts by weight: 4-14 parts of epoxy resin, 2-9 parts of curing agent, 78-92 parts of inorganic filler, 0.05-1 part of catalyst and 0-6 parts of additive.
2. The epoxy resin composition of claim 1, wherein the epoxy resin comprises at least two epoxy groups.
3. The epoxy resin composition as claimed in claim 1 or 2, wherein the epoxy resin is selected from the group consisting of multifunctional structure, novel multifunctional structure, polyaromatic ring structure, o-cresol structure epoxy resin and combinations thereof.
4. The epoxy resin composition as claimed in claim 1, wherein the epoxy resin comprises one or a combination of the following formulas (I), (II), (III), (IV), (V) and (VI):
formula (I):
formula (II):
formula (III):
formula (IV):
formula (V):
formula (VI):
5. the epoxy resin composition as claimed in claim 4, wherein the epoxy resin has an epoxy equivalent of 160-300g/eq in formula (I), formula (II), formula (III), formula (IV) or formula (V).
6. The epoxy resin composition according to claim 1, wherein the curing agent is a phenolic resin-based curing agent; the phenolic resin curing agent is selected from a multifunctional group structure, a multi-aromatic ring structure, phenolic resin and a combination thereof, wherein the multifunctional group structure is shown as a formula (VII), the multi-aromatic ring structure is shown as a formula (VIII), and the phenolic resin is shown as a formula (IX):
formula (VII):
formula (VIII):
formula (IX):
7. the epoxy resin composition as claimed in claim 6, wherein the phenolic resin curing agent has a hydroxyl group equivalent weight of 90 to 210g/eq in the formulae (VII), (VIII) and (IX).
8. An epoxy resin composition according to any one of claims 1 to 7, characterized by one or more of the following properties:
A. curing at 175 + -2 deg.C for 90 seconds with a spiral flow length of 25-55 inches;
B. gelation time at 175 + -2 deg.C is 25-55 s;
C. the glass transition temperature is 175-225 ℃ at 175 +/-2 ℃;
D. the flexural modulus is 25MPa or less at 25 ℃.
9. A process for the preparation of an epoxy resin composition according to any one of claims 1 to 8, comprising at least the following steps:
(1) Respectively crushing the epoxy resin and the curing agent to obtain powder, subpackaging, sealing and storing at low temperature for later use;
(2) Adding the inorganic filler, the catalyst and the additive into a high-speed stirrer in batches, stirring and mixing, and adding the epoxy resin and the curing agent which are crushed in the step (1) for mixing;
(3) And pouring the uniformly mixed mixture into an extruder for mixing, cooling and crushing to obtain the composite material.
10. Use of an epoxy resin composition according to any one of claims 1 to 8 in electronic packaging.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116970262A (en) * | 2023-04-24 | 2023-10-31 | 上海道宜半导体材料有限公司 | Epoxy resin composition for large-size QFN (quad Flat No-lead) product and preparation method thereof |
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| CN115466486B (en) | 2023-07-28 |
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