CN116262849A - Epoxy plastic package material with low dielectric constant and preparation method and application thereof - Google Patents

Epoxy plastic package material with low dielectric constant and preparation method and application thereof Download PDF

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CN116262849A
CN116262849A CN202111515115.0A CN202111515115A CN116262849A CN 116262849 A CN116262849 A CN 116262849A CN 202111515115 A CN202111515115 A CN 202111515115A CN 116262849 A CN116262849 A CN 116262849A
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epoxy
mass
epoxy resin
inorganic filler
resin
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付可欣
朱朋莉
张未浩
艾文季
罗延杰
谢鑫
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Shenzhen Institute of Advanced Electronic Materials
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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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/295—Organic, e.g. plastic containing a filler
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

The invention discloses an epoxy plastic package material with low dielectric constant, a preparation method and application thereof, wherein the epoxy plastic package material comprises the following components: an epoxy resin; a phenolic resin; an inorganic filler; a silane coupling agent; a release agent comprising at least one of the following (α) and (β): (a) a linear saturated carboxylic acid having a number average molecular weight of 550 to 800, (β) an oxidized polyethylene wax; a curing accelerator; a flame retardant; vapor phase silicon; the epoxy resin in the composition comprises a fluorine-containing epoxy resin and/or the inorganic filler comprises a fluorinated modified inorganic filler. The epoxy plastic package material has low dielectric constant and good manufacturability, and can be used for packaging semiconductor devices.

Description

Epoxy plastic package material with low dielectric constant and preparation method and application thereof
Technical Field
The invention belongs to the technical field of electronic packaging materials, and relates to an epoxy plastic packaging material with a low dielectric constant, and a preparation method and application thereof.
Background
The epoxy plastic packaging material is widely applied to the fields of semiconductor devices, integrated circuits, consumer electronics and the like due to the characteristics of high reliability, low cost, simple production process and the like, and occupies more than 97% of the market of the whole microelectronic packaging material. In recent years, electronic packaging technology has been developed toward miniaturization and weight saving of components, and packaging forms are gradually changed from QFP (quad flat package) technology, SOP (small-size package) technology to high-density pins, high-precision packaging technology with high I/O numbers, such as: BGA (ball grid array), CSP (chip size package), etc. The updating iteration of the packaging technology has higher requirements on the performances of fluidity, heat dissipation, dielectric property, warping and the like of the epoxy plastic packaging material.
The epoxy plastic package material is one of the key materials for microelectronic package, and has the main functions of protecting high-density arranged solder balls and chips, and ensuring the processability, safety and weather resistance of the chips. However, from the aspect of dielectric performance, most of epoxy plastic packaging materials currently have high dielectric constants, so that leakage current of the whole component is increased and a capacitance effect is generated. Therefore, the performance of the existing epoxy plastic packaging material can not meet the high-speed development of the packaging technology.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide an epoxy molding compound with low dielectric constant, and a preparation method and application thereof. In order to reduce the dielectric constant of the epoxy molding compound, the invention selects the fluorine-containing epoxy resin with low viscosity and low water absorption as a resin system component and/or selects the fluorinated modified inorganic filler as a main filler. The epoxy plastic packaging material has the advantages of low dielectric constant, low water absorption, high fluidity and the like, so that the packaging components have higher electrical insulation property and structural reliability.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: an epoxy molding compound with low dielectric constant comprises the following components:
(A) An epoxy resin;
(B) A phenolic resin;
(C) An inorganic filler;
(D) A silane coupling agent;
(E) A release agent comprising at least one of the following (α) and (β): (a) a linear saturated carboxylic acid having a number average molecular weight of 550 to 800, (β) an oxidized polyethylene wax;
(F) A curing accelerator;
(G) A flame retardant;
(H) Vapor phase silicon;
the epoxy resin in the composition comprises a fluorine-containing epoxy resin and/or the inorganic filler comprises a fluorinated modified inorganic filler.
Further, the content of the epoxy resin is 4% -25% of the weight of the epoxy plastic packaging material; when the epoxy resin contains fluorine-containing epoxy resin, the content of the fluorine-containing epoxy resin is 0.5-6.5% of the weight of the epoxy molding compound;
preferably, the content of the phenolic resin is 3-15% of the weight of the epoxy plastic packaging material;
preferably, the content of the inorganic filler is 60% -93% of the weight of the epoxy plastic packaging material, and preferably 70% -92%; (in the case of too small inorganic filler content, the viscosity of the epoxy molding compound is too low, voids are easy to generate during molding, and the improvement of dielectric constant and thermal expansion coefficient is small, in contrast, in the case of too large inorganic filler content, the fluidity of the epoxy molding compound is poor, and defects such as incomplete filling are easy to form);
preferably, the content of the silane coupling agent is 0.05% -0.5% by weight of the inorganic filler, preferably 0.1% -2.5%;
preferably, the content of the release agent is 0.005% -2% of the weight of the epoxy plastic packaging material;
preferably, the content of the curing accelerator is 0.005-2% of the weight of the epoxy plastic packaging material, and preferably 0.01-0.5%; (if the amount of the curing accelerator is less than 0.005%, the curability tends to be poor in a short time, and if it exceeds 2%, the curing speed is too high, and it is difficult to obtain a molded article of a good shape);
preferably, the flame retardant is an ester of a compound of phosphoric acid and alcohol or a compound of phenol, and the content of the flame retardant is calculated as phosphorus atoms to be 0.2-0.5% of the weight of the epoxy plastic package material; (if it is less than 0.2%, problems such as wire sweep, molding cavity and the like tend to occur, and if it is more than 0.5%, moldability and moisture resistance tend to be lowered)
Preferably, the content of the gas phase silicon is 0.2% -0.5% of the weight of the epoxy plastic packaging material.
Further, the epoxy resin includes at least one of an epoxy resin A1 and a fluorine-containing epoxy resin A2. When the epoxy resin includes A1 and A2, the mass of A2 is 0.05 to 0.85, preferably 0.05 to 0.7, and more preferably 0.3 to 0.7 of the total mass of the epoxy resin.
Further, the molecular structural formula of the fluorine-containing epoxy resin A2 is shown as a formula (1), wherein R is an F-containing structure:
Figure BDA0003406603110000021
preferably, the fluorine-containing epoxy resin A2 is selected from at least one of the formula (1-1) preparation method references "Ding J P, tao Z Q, fan L, et al Synthesis and properties of fluorinated biphenyl-type epoxy resin [ J ]. Journal of Applied Polymer Science,2009,113 (3)", formula (1-2) preparation method references "Ge, Z.Y., et al Synthesis and properties of novel fluorinated epoxy resins [ J ]. Journal of Applied Polymer Science,2011,120 (1)", formula (1-3) preparation method references "Jiang, J., et al Portous Epoxy Film for Low Dielectric Constant Chip Substrates and Board s.2018." and formula (1-4) preparation method references "Tian M A, jm A, jz A, et al Curing behaviors and properties of epoxy resins with para-hexatomic ring blocks: excellent comprehensive performances of tetrafluorophenyl [ J ]. Polymer, 206.".
Figure BDA0003406603110000031
Further, the epoxy resin A1 is a commonly used encapsulating epoxy resin molding compound, and is not particularly limited; the epoxy resin A1 comprises phenol, cresol, xylenol, resorcinol, catechol, bisphenol A, bisphenol F and other phenols and/or alpha-naphthol, beta-naphthol, dihydroxynaphthalene and other naphthols, formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, salicylaldehyde and other aldehyde-containing compounds, and is obtained by condensation or co-condensation of the phenol-formaldehyde resin with an acidic catalyst; alkyl substituted or unsubstituted diglycidyl ether type epoxy resin; 1, 2-stilbene type epoxy resin; an epoxy resin containing sulfur atoms; hydroquinone-type epoxy resins; glycidyl ester type epoxy resins obtained by reacting polybasic acids such as phthalic acid and dimer acid with epichlorohydrin; glycidylamine type epoxy resin obtained by reacting polyamine such as diaminodiphenylmethane and isocyanic acid with epichlorohydrin; epoxide of dicyclopentadiene and phenol and/or naphthol co-condensation resin; an epoxy resin containing naphthalene ring; phenol-aralkyl resins; epoxides of aralkyl phenol resins such as naphthol-aralkyl resins; trimethylolpropane type epoxy resin; an alicyclic epoxy resin, etc., which may be used alone or in combination of 2 or more kinds thereof;
preferably, a difunctional epoxy resin, preferably an epoxy resin having biphenyl groups represented by the following general formula (2):
Figure BDA0003406603110000041
in the formula (2), R 1 To R 8 Each independently selected from a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having a carbon number of 1 to 10, n represents an integer of 0 to 3;
in the above general formula, the substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms may be a saturated or unsaturated hydrocarbon group, and in addition, the substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms may be linear, branched or cyclic, but is particularly preferably a methyl group or an ethyl group.
Further, the phenolic resin has a function as a curing agent for the epoxy resin. The phenolic resin comprises one or more of phenol novolac resin, biphenyl aralkyl type phenolic resin, cresol novolac type epoxy resin, biphenyl type phenolic resin, triphenylmethane type phenolic resin, naphthol phenolic resin and aralkyl phenolic resin; preferably, the phenolic resin comprises a low moisture absorption resin such as one or both of a biphenyl aralkyl type phenolic resin and a phenol novolac resin.
Further, the equivalent ratio of the epoxy resin to the phenolic resin, that is, the ratio of the number of epoxy groups in the epoxy resin to the number of hydroxyl groups in the phenolic resin is not particularly limited, and is preferably set in the range of 0.5 to 2, more preferably in the range of 0.6 to 1.3, in order to suppress the respective unreacted portions to a small extent. In order to obtain an encapsulating epoxy resin molding compound excellent in moldability and reflow resistance, the molding compound is more preferably set in the range of 0.8 to 1.0.
Further, the inorganic filler includes one or more of a fluorinated modified inorganic filler (the inorganic filler is fluorinated modified to lower the dielectric constant), an unmodified inorganic filler; the inorganic filler may be used in any form such as a crushed form, a spherical form or a ground form;
preferably, the inorganic filler includes a fluorinated modified inorganic filler and an unmodified inorganic filler; more preferably, the inorganic filler includes fluorinated modified silica and silica;
preferably, the average particle diameter of the inorganic filler is 0.1 to 45 μm, preferably 0.1 to 10 μm, from the viewpoint of fluidity.
Further, the fluorinated modifier used by the fluorinated modified inorganic filler is a fluorinated silane coupling agent, and the general formula is shown in formula (3), wherein R is a fluorinated structure:
Figure BDA0003406603110000042
preferably, the fluorinated modifier comprises one or more of heptadecafluorodecyl trimethoxysilane, perfluorooctyl triethoxysilane, tridecafluorooctyl trimethoxysilane, pentafluorophenyl triethoxysilane, 3- (heptafluoroisopropoxy) propyl triethoxysilane, monofluorotriethoxysilane, methyl (3, 3-trifluoropropyl) diethoxysilane, 3-trifluoroacetoxypropyl trimethoxysilane;
more preferably, the fluorinated modifier comprises pentafluorophenyl triethoxysilane
Figure BDA0003406603110000051
Methyl (3, 3-trifluoropropyl) diethoxysilane->
Figure BDA0003406603110000052
3- (heptafluoroisopropoxy) propyltriethoxysilane->
Figure BDA0003406603110000053
One or more of the following.
Further, the preparation method 1 of the fluorinated modified inorganic filler comprises the following steps: uniformly mixing inorganic filler and fluorine-containing silane coupling agent by using magnetic stirring, heating the mixed solution, continuing to magnetically stir for a period of time, washing the filler, and drying the filler in an oven to obtain fluorine-containing silane coupling agent modified inorganic filler for later use; preferably, the mass ratio of the fluorine-containing silane coupling agent to the inorganic filler is 0.02-0.08:1.
the preparation method 2 of the fluorinated modified inorganic filler comprises the following steps: adding inorganic filler into a heating mixer, adding the fluorine-containing silane coupling agent into the mixer in the stirring process at a certain frequency and content, and stirring for a period of time by the mixer to obtain fluorine-containing silane coupling agent modified inorganic filler for later use; preferably, the mass ratio of the fluorine-containing silane coupling agent to the inorganic filler is 0.02-0.08:1.
the preparation method 3 of the fluorinated modified inorganic filler comprises the following steps: adding inorganic filler into a reaction kettle, carrying the prepared fluorine-containing silane coupling agent into the reaction kettle through a gas circuit, and generating plasma in a dielectric barrier discharge mode to obtain fluorine-containing silane coupling agent modified inorganic filler for later use; preferably, the mass ratio of the fluorine-containing silane coupling agent to the inorganic filler is 0.02-0.08:1.
further, the general formula of the silane coupling agent is shown as formula (4):
Figure BDA0003406603110000061
in the formula (4): m is an integer of 1 to 3; n is an integer of 0 to 3; r is R 1 Selected from:
Figure BDA0003406603110000062
H 2 N-、/>
Figure BDA0003406603110000063
Figure BDA0003406603110000064
HS-/>
Figure BDA0003406603110000065
wherein, (X) j Selected from hydrogen atoms and alkyl groups with 1-6 carbon atoms; r is R 2 、R 3 Each independently selected from methyl or ethyl, and at R 2 OR 3 In the case where a plurality of the above-mentioned materials are present, they may be the same or different from each other;
in some specific embodiments, the silane coupling agent having the formula (4) may be exemplified by: one or more of gamma- (2, 3-glycidoxypropoxy) propyltrimethoxysilane, trimethyloxyphenyl silane, 3-aminopropyl triethoxysilane, 3- (methacryloyloxy) propyltrimethoxysilane, vinyltrimethoxysilane, (3-aminopropyl) triethoxysilane, gamma-mercaptopropyltrimethoxysilane, gamma-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyl trimethoxysilane, gamma-anilinopropyl triethoxysilane, gamma-anilinopropyl methyldimethoxysilane, gamma-anilinopropyl methyldiethoxysilane, gamma-anilinopropyl ethyldiethoxysilane, gamma-anilinopropyl ethyldimethoxysilane, gamma-anilinopropyl trimethoxysilane, gamma-anilinopropyl triethoxysilane, gamma-anilinomethyl dimethoxysilane, gamma-anilinomethyl diethoxysilane;
preferably, from the aspect of fluidity, the silane coupling agent is selected from one or more of amino organosilane coupling agents represented by formula (4-1);
Figure BDA0003406603110000066
in the formula (4-1): m is an integer of 1 to 3; n is an integer of 0 to 3; (X) j Selected from hydrogen atoms and alkyl groups with 1-6 carbon atoms; r is R 2 、R 3 Each independently selected from methyl or ethyl, and at R 2 OR 3 In the case where a plurality of the above-mentioned materials are present, they may be the same or different from each other;
the amino organosilane coupling agent represented by the formula (4-1) may be: gamma-anilinopropyl trimethoxysilane, gamma-anilinopropyl triethoxysilane, gamma-anilinopropyl methyl dimethoxysilane, gamma-anilinopropyl methyl diethoxysilane, gamma-anilinopropyl ethyl dimethoxysilane, etc.;
more preferably, the silane coupling agent is gamma-anilinopropyl trimethoxysilane;
when the amino organosilane coupling agent is mixed into the epoxy resin composition, the cohesiveness of the filler and the resin can be improved, and the bulk performance of the filler can be better exerted.
Further, the linear saturated carboxylic acid having a number average molecular weight of 550 to 800 in the mold release agent is a compound represented by the formula (5):
Figure BDA0003406603110000071
more preferably, the linear saturated carboxylic acid has a number average molecular weight of 600 to 800.
Further, in view of the hardenability of the epoxy molding compound, a curing accelerator is further added in the present invention. The curing accelerator used in the invention is a substance commonly used in epoxy resin molding compounds for encapsulation, and is not particularly limited; the curing accelerator includes cyclic amidine compounds such as 1, 8-diaza-bicyclo [5.4.0] undecene-7, imidazolines such as 1, 5-diaza-bicyclo [4.3.0] nonene, 5, 6-dibutylamino-1, 8-diaza-bicyclo [5.4.0] undecene-7, and the like, and organic phosphines such as tributylphosphine, methyl diphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, phenylphosphine, and the like, and compounds having pi-polar bonds such as maleic anhydride, the above quinone compounds, phenylazomethane, phenol resins, and the like added thereto, and intramolecular compounds such as polar compounds such as maleic anhydride, 1, 4-benzoquinone, 2, 5-dimethylbenzoquinone, 2, 3-dimethylbenzoquinone, 2, 6-dimethylbenzoquinone, 2, 3-dimethoxy-5-methyl-1, and the like, 2-methylimidazoline, 2-phenylimidazoline, 2-phenyl-4-methylimidazoline, and the like, and derivatives thereof.
Further, the flame retardant used in the present invention is not particularly limited as long as it is an esterified compound of phosphoric acid with an alcohol or with a phenol. The flame retardant includes trimethyl phosphate, triethyl phosphate, triphenyl phosphate, dihydroxytolyl phosphate, xylyl phosphate, and the like. Wherein from the viewpoint of hydrolysis resistance, it is preferable to use an aromatic condensed phosphoric ester represented by the formula (6) wherein R represents a reactive group having affinity or reactivity with the epoxy resin, and R is selected from any one of mercapto group, vinyl group, epoxy group, amide group, aminophenyl group, amino group, epoxy group, cyano group or methacryloxy group, and may be the same as or different from each other;
Figure BDA0003406603110000072
further, the fumed silica used in the present invention is fumed silica generally used in an encapsulating epoxy resin composition, and is not particularly limited. Preferably, the average particle size of the vapor phase silicon is in the range of 5 to 40 nm.
On the other hand, the invention provides a preparation method of the low-dielectric-constant epoxy molding compound, which is characterized in that epoxy resin, phenolic resin, inorganic filler, silane coupling agent, release agent, curing accelerator, flame retardant and gas-phase silicon are mixed, and the mixture is kneaded and mixed, cooled and finely crushed under the condition that the extrusion temperature is 80-110 ℃ to obtain the low-dielectric-constant epoxy molding compound.
In another aspect, the present invention provides an application of any one of the low dielectric constant epoxy molding compound described above in packaging of semiconductor devices.
The beneficial effects of this application are: the conventional resin system and the filler modification method can not keep low dielectric while meeting high filling, and the invention selects the fluorine-containing epoxy resin as a resin system component and/or selects the fluorinated modified inorganic filler as a main filler, thereby realizing that the epoxy plastic package material keeps low dielectric while finishing high filling.
Detailed Description
In order that the contents of the present invention may be better understood, the present invention will be described below with reference to the following examples and comparative examples, but the present invention should not be construed as being limited to these examples.
The epoxy resins used in the following examples and comparative examples are listed below:
epoxy resin 1: by the general formula
Figure BDA0003406603110000081
Represented by formula (I), wherein R is 1 To R 8 Methyl, and n is 0 (epoxy equivalent: 192, melting point: 105 ℃, available from Mitsubishi chemical corporation under the trade designation YX 4000K).
Epoxy resin 2: fluorine-containing epoxy resin
Figure BDA0003406603110000082
(epoxy equivalent: 181, melting point: 34 ℃ C., homemade).
The phenolic resins used in the following examples and comparative examples are listed below:
phenolic resin 1: biphenyl aralkyl phenol resin (hydroxyl equivalent: 203, softening point: 65 ℃, available from Ming and Chemie Co., ltd., trade name: MEH-7851 SS).
Phenolic resin 2: phenol novolac resin (hydroxyl equivalent: 104, softening point: 60 ℃, trade name PR-HF-3, available from Kagaku Co., ltd.).
The fillers used in the following examples and comparative examples are listed below: fluorinated modified SiO 2 Powder and SiO 2 The average particle size of the powder is 5-8 μm, and the particle size of the cutting point is 45 μm.
Fluorinated modifier 1: pentafluorophenyl triethoxysilane
Figure BDA0003406603110000091
Fluorinated modifier 2: methyl (3, 3-trifluoropropyl) diethoxysilane
Figure BDA0003406603110000092
Fluorinated modifier 3:3- (heptafluoroisopropoxy) propyltriethoxysilane
Figure BDA0003406603110000093
The silane coupling agents used in the following examples and comparative examples are listed below:
silane coupling agent 1: gamma-anilinopropyl trimethoxysilane.
The release agents used in the following examples and comparative examples are listed below: CH (CH) 3 -(CH 2 ) n -COOH(n=24), nikko Carnauba, available from Nikko Fine corporation.
The curing accelerators used in the following examples and comparative examples were: triphenylphosphine.
The flame retardants used in the following examples and comparative examples are: trimethyl phosphate.
The vapor phase silicon used in the following examples and comparative examples was: the average grain diameter of the nano silicon dioxide is 5-40 nm, and the specific surface area is 300+/-30 m 2 /g。
The colorants used in the following examples and comparative examples were: black organic dye.
Example 1
6.02 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.81 parts by mass of silicon dioxide, 0.3 part by mass of gas phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition of extrusion temperature of 110 ℃, cooled and finely crushed, and finally the epoxy molding compound for low dielectric constant is obtained.
Example 2
500 parts by mass of silicon dioxide and 25 parts by mass of pentafluorophenyl triethoxysilane are poured into a three-neck flask; stirring for 20min at normal temperature by using a magnetic rotor, heating the mixed solution to 80 ℃ by using an oil bath, continuing to magnetically stir and react for 30min, washing the redundant silane coupling agent for 3-5 times by using 98% ethanol after the reaction is finished, and finally drying for 24h at 80 ℃ in a drying oven to obtain the fluorinated modified filler 1.
6.02 parts by mass of epoxy resin 1,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.61 parts by mass of fluorinated modified filler 1,0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed at an extrusion temperature of 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 3
6.02 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.81 fluorinated modified silica filler 1,0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition of extrusion temperature of 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 4
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 40 parts by mass of fluorinated modified filler 1, 47.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 5
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 50 parts by mass of fluorinated modified filler 1, 37.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 6
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 60 parts by mass of fluorinated modified filler 1, 27.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 7
500 parts by mass of silica and 25 parts by mass of methyl (3, 3-trifluoropropyl) diethoxysilane are poured into a three-necked flask; stirring for 20min at normal temperature by using a magnetic rotor, heating the mixed solution to 80 ℃ by using an oil bath, continuing to magnetically stir and react for 30min, washing the redundant silane coupling agent for 3-5 times by using 98% ethanol after the reaction is finished, and finally drying for 24h at 80 ℃ in a drying oven to obtain the fluorinated modified filler 2.
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 2,0.25 parts by mass of release agent, 40 parts by mass of fluorinated modified filler 2, 47.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 8
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 2,0.25 parts by mass of release agent, 50 parts by mass of fluorinated modified filler 2, 37.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 9
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 2,0.25 parts by mass of release agent, 60 parts by mass of fluorinated modified filler 2, 27.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 10
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 3,0.25 parts by mass of release agent, 40 parts by mass of fluorinated modified filler 3, 47.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 11
500 parts by mass of silica and 25 parts by mass of 3- (heptafluoroisopropoxy) propyltriethoxysilane are poured into a three-necked flask; stirring for 20min at normal temperature by using a magnetic rotor, heating the mixed solution to 80 ℃ by using an oil bath, continuing to magnetically stir and react for 30min, washing the redundant silane coupling agent for 3-5 times by using 98% ethanol after the reaction is finished, and finally drying for 24h at 80 ℃ in a drying oven to obtain the fluorinated modified filler 3.
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 3,0.25 parts by mass of release agent, 50 parts by mass of fluorinated modified filler 3, 37.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Example 12
2.107 parts by mass of epoxy resin 1,3.913 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 3,0.25 parts by mass of release agent, 60 parts by mass of fluorinated modified filler 3, 27.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed under the condition that the extrusion temperature is 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Comparative example 1
6.02 parts by mass of epoxy resin 1,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.81 parts by mass of modified silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, and kneading, cooling and fine crushing are carried out under the condition that the extrusion temperature is 80 ℃, so that the epoxy molding compound with low dielectric constant is obtained.
Comparative example 2
5.418 parts by mass of epoxy resin 1,0.602 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed at an extrusion temperature of 80 ℃, cooled and finely crushed, and finally the epoxy plastic package material with low dielectric constant is obtained.
Comparative example 3
5.719 parts by mass of epoxy resin 1,0.301 parts by mass of epoxy resin 2,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 87.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, kneaded and mixed at an extrusion temperature of 80 ℃, cooled and finely crushed, and finally the epoxy molding compound with low dielectric constant is obtained.
Comparative example 4
6.02 parts by mass of epoxy resin 1,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 10 parts by mass of fluorinated modified filler 1, 77.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, and kneading, cooling and fine crushing are carried out under the condition that the extrusion temperature is 80 ℃, so that the epoxy molding compound with low dielectric constant is obtained.
Comparative example 5
6.02 parts by mass of epoxy resin 1,2.78 parts by mass of phenolic resin 1,1.19 parts by mass of phenolic resin 2,0.28 parts by mass of curing accelerator, 0.41 part by mass of flame retardant, 0.15 part by mass of silane coupling agent 1,0.25 parts by mass of release agent, 20 parts by mass of fluorinated modified filler 1, 67.81 parts by mass of silicon dioxide, 0.3 part by mass of gas-phase silicon and 0.2 part by mass of colorant are mixed, and kneading, cooling and fine crushing are carried out under the condition that the extrusion temperature is 80 ℃, so that the epoxy molding compound with low dielectric constant is obtained.
Test method
Spiral flow: the epoxy resin composition was molded by transfer molding under the structural conditions of a mold temperature of 175℃and a molding pressure of 6.9MPa and a curing time of 90s using a mold for spiral flow measurement according to EMMI-1-66, to obtain a flow distance (cm).
Gelation time: the epoxy resin composition was placed on a curing plate heated to 175℃and the sample was stirred uniformly using a spatula in the front section, and the time was stopped when the sample gel, which was the gelation time, was counted by a stopwatch.
Viscosity measurement: the measurement was carried out by using an Shimadzu capillary rheometer at 175℃under a load of 10Kgf and a viscosity unit Pa.s.
Dielectric constant measurement: using radio-frequency impedance materialMaterial analyzer, test frequency 10 6 The samples of the above examples were tested for dielectric constant at Hz according to GB/T1409-2006 test standard.
Dielectric loss tangent measurement: testing frequency 10 using a radio frequency impedance material analyzer 6 The samples of the above examples were subjected to the dielectric loss tangent test at Hz according to the GB/T1409-2006 test standard.
The contents of the components and the sample performance parameters of the above examples and comparative examples are shown in Table 1:
TABLE 1
Figure BDA0003406603110000141
Figure BDA0003406603110000142
/>
Figure BDA0003406603110000151
Figure BDA0003406603110000152
Figure BDA0003406603110000161
/>
By way of example, it has been found that the introduction of fluorine-containing resins and fluorine-containing fillers can reduce the dielectric constant and dielectric loss of the molding compound, and that the increase in fluorine-containing chain length and fluorine element content of the fluorinated modifier is more effective in reducing the dielectric constant, but at some sacrifice in viscosity and flowability. It is evident from examples 1-3 that the introduction of a low viscosity fluorine-containing resin can reduce the viscosity of the system, increase the flow length, reduce the viscosity sacrifice of the fluorine-containing filler, and reduce the dielectric properties. Wherein the benzene ring-containing fluorinated modifier reduces the same dielectric constant as compared with a long-chain fluorinated modifier, and has less viscosity sacrifice. This is mainly related to the unique electronic effect of the fluorine-containing phenyl group, and the dielectric constant and dielectric loss reduction similar to those of the system with a larger fluorine content can be obtained with a smaller fluorine content.
In conclusion, the epoxy resin molding compound provided by the invention can realize high filling and low dielectric property.
The foregoing is merely a specific embodiment of the present invention and not all embodiments, and any equivalent modifications of the technical solution of the present invention that will be obvious to those skilled in the art from reading the present specification are intended to be encompassed by the claims of the present invention.

Claims (10)

1. The epoxy molding compound with low dielectric constant is characterized by comprising the following components:
(A) An epoxy resin;
(B) A phenolic resin;
(C) An inorganic filler;
(D) A silane coupling agent;
(E) A release agent comprising at least one of the following (α) and (β);
(a) a linear saturated carboxylic acid having a number average molecular weight of 550 to 800, (β) an oxidized polyethylene wax;
(F) A curing accelerator;
(G) A flame retardant;
(H) Vapor phase silicon;
the epoxy resin in the composition comprises a fluorine-containing epoxy resin and/or the inorganic filler comprises a fluorinated modified inorganic filler.
2. The low dielectric constant epoxy molding compound according to claim 1, wherein the content of the epoxy resin is 4% -25% of the weight of the epoxy molding compound; when the epoxy resin contains fluorine-containing epoxy resin, the content of the fluorine-containing epoxy resin is 0.5-6.5% of the weight of the epoxy molding compound;
preferably, the content of the phenolic resin is 3-15% of the weight of the epoxy plastic packaging material;
preferably, the content of the inorganic filler is 60% -93% of the weight of the epoxy plastic packaging material, and preferably 70% -92%;
preferably, the content of the silane coupling agent is 0.05% -0.5% by weight of the inorganic filler, preferably 0.1% -2.5%;
preferably, the content of the release agent is 0.005% -2% of the weight of the epoxy plastic packaging material;
preferably, the content of the curing accelerator is 0.005-2% of the weight of the epoxy plastic packaging material, and preferably 0.01-0.5%;
preferably, the flame retardant is an ester of a compound of phosphoric acid and alcohol or a compound of phenol, and the content of the flame retardant is calculated as the content of phosphorus atoms and is 0.2-0.5% of the weight of the epoxy plastic package material except the inorganic filler;
preferably, the content of the gas phase silicon is 0.2% -0.5% of the weight of the epoxy plastic packaging material.
3. The low dielectric constant epoxy molding compound according to claim 1, wherein the epoxy resin comprises at least one of epoxy resin A1 and fluorine-containing epoxy resin A2;
preferably, the molecular structural formula of the fluorine-containing epoxy resin A2 is shown as a formula (1), wherein R is an F-containing structure:
Figure FDA0003406603100000011
preferably, the fluorine-containing epoxy resin A2 is selected from at least one of epoxy resins represented by formula (1-1), formula (1-2), formula (1-3) and formula (1-4);
Figure FDA0003406603100000021
4. the low dielectric constant epoxy molding compound according to claim 3, wherein the epoxy resin A1 is selected from one or more of epoxy resins represented by formula (2);
Figure FDA0003406603100000022
in the formula (2), the R 1 To R 8 Each independently selected from a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having a carbon number of 1 to 10, n represents an integer of 0 to 3; preferably, the substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms is a methyl group or an ethyl group;
preferably, the epoxy resin includes a fluorine-containing epoxy resin A2 represented by formula (1) and an epoxy resin A1 represented by formula (2); when the epoxy resin includes A1 and A2, the mass of A2 is 0.05 to 0.85, preferably 0.05 to 0.7, and more preferably 0.3 to 0.7 of the total mass of the epoxy resin.
5. The low dielectric constant epoxy molding compound of claim 1, wherein the phenolic resin comprises one or more of phenol novolac resin, biphenyl aralkyl type phenolic resin, cresol novolac type epoxy resin, biphenyl type phenolic resin, triphenylmethane type phenolic resin, naphthol novolac resin, aralkyl phenolic resin;
preferably, the phenolic resin comprises one or more of a biphenyl aralkyl type phenolic resin and a phenol novolac resin.
6. The low dielectric constant epoxy molding compound according to claim 1, wherein the inorganic filler comprises one or more of a fluorinated modified inorganic filler and an unmodified inorganic filler;
preferably, the inorganic filler includes a fluorinated modified inorganic filler and an unmodified inorganic filler; more preferably, the inorganic filler includes fluorinated modified silica and silica;
preferably, the inorganic filler has an average particle diameter of 0.1 to 45 μm, preferably 0.1 to 10 μm;
preferably, the fluorinated modifier used in the fluorinated modified inorganic filler is a fluorinated silane coupling agent, and the general formula is shown in formula (3), wherein R is a fluorinated structure:
Figure FDA0003406603100000031
preferably, the fluorinated modifier comprises one or more of heptadecafluorodecyl trimethoxysilane, perfluorooctyl triethoxysilane, tridecafluorooctyl trimethoxysilane, pentafluorophenyl triethoxysilane, 3- (heptafluoroisopropoxy) propyl triethoxysilane, monofluorotriethoxysilane, methyl (3, 3-trifluoropropyl) diethoxysilane, 3-trifluoroacetoxypropyl trimethoxysilane;
more preferably, the fluorinated modifier comprises one or more of pentafluorophenyl triethoxysilane, methyl (3, 3-trifluoropropyl) diethoxysilane, 3- (heptafluoroisopropoxy) propyl triethoxysilane.
7. The low dielectric constant epoxy molding compound according to claim 1, wherein the silane coupling agent is one or more selected from the group consisting of silane coupling agents represented by formula (4):
Figure FDA0003406603100000032
in the formula (4): m is an integer of 1 to 3; n is an integer of 0 to 3; r1 is selected from:
Figure FDA0003406603100000033
H 2 N-、/>
Figure FDA0003406603100000034
Figure FDA0003406603100000035
HS-/>
Figure FDA0003406603100000036
wherein, (X) j Selected from hydrogen atoms and alkyl groups with 1-6 carbon atoms; r is R 2 、R 3 Each independently selected from methyl or ethyl, and at R 2 OR 3 In the case where a plurality of the above-mentioned materials are present, they may be the same or different from each other;
preferably, the silane coupling agent is one or more of amino organosilane coupling agents represented by formula (4-1);
Figure FDA0003406603100000041
in the formula (4-1): m is an integer of 1 to 3; n is an integer of 0 to 3; (X) j Selected from hydrogen atoms and alkyl groups with 1-6 carbon atoms; r is R 2 、R 3 Each independently selected from methyl or ethyl, and at R 2 OR 3 In the case where a plurality of the above-mentioned materials are present, they may be the same or different from each other;
more preferably, the silane coupling agent is gamma-anilinopropyl trimethoxysilane.
8. The low dielectric constant epoxy molding compound according to claim 1, wherein the linear saturated carboxylic acid having a number average molecular weight of 550 to 800 in the mold release agent is a compound represented by formula (5):
Figure FDA0003406603100000042
preferably, the linear saturated carboxylic acid has a number average molecular weight of 600 to 800.
9. The method for preparing the low-dielectric-constant epoxy molding compound according to any one of claims 1 to 8, wherein epoxy resin, phenolic resin, inorganic filler, silane coupling agent, release agent, curing accelerator, flame retardant and gas-phase silicon are mixed, kneaded and mixed under the condition that the extrusion temperature is 80-110 ℃, cooled and finely crushed to obtain the low-dielectric-constant epoxy molding compound.
10. Use of the low dielectric constant epoxy molding compound of any one of claims 1-8 in semiconductor device packaging.
CN202111515115.0A 2021-12-13 2021-12-13 Epoxy plastic package material with low dielectric constant and preparation method and application thereof Pending CN116262849A (en)

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