CN116023411A - Preparation method of organic phosphorus compound, epoxy plastic packaging material and application thereof - Google Patents
Preparation method of organic phosphorus compound, epoxy plastic packaging material and application thereof Download PDFInfo
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- CN116023411A CN116023411A CN202211713296.2A CN202211713296A CN116023411A CN 116023411 A CN116023411 A CN 116023411A CN 202211713296 A CN202211713296 A CN 202211713296A CN 116023411 A CN116023411 A CN 116023411A
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Abstract
The invention relates to the technical field of epoxy plastic packaging materials, in particular to a preparation method of an organic phosphorus compound, an epoxy plastic packaging material and application thereof. The method comprises the following steps: under the existence of alkaline solution and organic solvent, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene undergo complex reaction to obtain an organic phosphorus compound. The obtained organic phosphorus compound is used as a curing accelerator to be added into a raw material composition, and the epoxy plastic package material is prepared by adding a mercapto-free coupling agent and controlling the proportion of raw material components. The epoxy plastic packaging material prepared by the method is odorless and environment-friendly, has higher copper adhesion and higher reliability in the application process of semiconductors.
Description
Technical Field
The invention relates to the technical field of epoxy plastic packaging materials, in particular to a preparation method of an organic phosphorus compound, an epoxy plastic packaging material and application thereof.
Background
The epoxy plastic packaging material is widely applied to the semiconductor packaging industry by virtue of the advantages of low shrinkage, excellent electrical insulation performance, chemical resistance, easy processing, low cost, convenient mass production and the like, and occupies 97% of the market of the whole microelectronic packaging material.
Along with the development of the times, the requirements of people on production and packaging environments are higher and higher, and the environmental awareness is stronger and stronger. Some raw material compositions used for preparing the epoxy plastic package material are prepared through chemical synthesis of different organic matters, the raw material compositions can have the taste of organic matters such as byproducts, solvents and the like generated in the reaction process, the raw material compositions are mixed together in a mechanical blending mode, the epoxy plastic package material is prepared through a melt extrusion mode, and generally, the melting temperature is high, so that some volatile matters in the raw material compositions are volatilized to the greatest extent, and a series of physical burdens are caused on the bodies of related workers.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art, and provides a preparation method of an organic phosphorus compound, an epoxy plastic package material and application thereof. The invention firstly reacts tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene under a certain condition to generate an organic phosphorus compound, then the obtained organic phosphorus compound is used as a curing accelerator to be added into a raw material composition, and the epoxy plastic package material prepared by adding a mercapto-free coupling agent and controlling the proportion of raw material components is odorless and environment-friendly, has higher copper adhesion and higher reliability in the application process of semiconductors.
In order to achieve the above object, the first aspect of the present invention provides a process for producing an organic phosphorus compound, the process comprising: under the existence of alkaline solution and organic solvent, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene undergo complexation reaction.
Preferably, the molar ratio of the tetraphenylphosphine bromide to the amount of the 2, 3-dihydroxynaphthalene is 1 to 5:2-8.
Preferably, the conditions of the complexation reaction include: the reaction temperature is 5-20 ℃ and the reaction time is 1-4h.
In a second aspect, the invention provides an epoxy molding compound, which is prepared from a raw material composition containing 3-15 wt% of epoxy resin, 2-10 wt% of phenolic resin, 0.05-2.0 wt% of curing accelerator, 70-90 wt% of filler, 0.1-1.2 wt% of mold release agent, 0.2-1.4 wt% of toughening agent, 0.3-2 wt% of coupling agent and 0-2 wt% of colorant, based on 100 wt% of the total weight of the raw material composition for preparing the epoxy molding compound,
wherein the coupling agent is a mercapto-free coupling agent, and the curing accelerator contains the organic phosphorus compound A and optionally one or more than two of tertiary amine compounds, organic phosphorus compounds B and imidazole compounds.
Preferably, the content of the organic phosphorus compound a is 5 to 100% by weight based on 100% by weight of the total weight of the curing accelerator.
Preferably, the tertiary amine compound is selected from one or more of 2,4, 6-tris (dimethylaminomethyl) phenol, 1, 8-diazabicyclo (5, 4, 0) undec-7-ene and triethylamine benzyl dimethylamine.
Preferably, the organic phosphorus compound B is selected from one or two or more of triphenylphosphine, triethylphosphine, trimethylphosphine, tributylphosphine, and tri (p-tolyl) phosphine.
Preferably, the imidazole compound is selected from one or more than two of 2-methylimidazole, 2, 4-dimethylimidazole, 2-ethyl 4-methylimidazole, 2-phenyl-4, 5-dihydroxymethylimidazole, 2-heptadecylimidazole and 3-amino-1, 2, 4-triazole.
Preferably, the mercapto-free coupling agent is selected from one or more of gamma-glycidoxypropyl trimethoxysilane, gamma-epoxypropyl propyl ether trimethoxysilane, gamma-aminopropyl triethoxysilane, gamma-aminopropyl trimethoxysilane, 2- (3, 4-epoxycyclohexane) ethyl trimethoxysilane and N-phenyl-3-aminopropyl trimethoxysiloxane.
Preferably, the toughening agent is selected from one or more than two of methyl methacrylate-butadiene-styrene terpolymer, acrylonitrile-butadiene-styrene copolymer, chlorinated polyethylene and ethylene-vinyl acetate copolymer.
Preferably, the median diameter of the filler is from 5 to 80. Mu.m.
The third aspect of the invention provides an application of the epoxy plastic packaging material as a semiconductor packaging material.
According to the technical scheme, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene react under certain conditions to generate an organophosphorus compound, the obtained organophosphorus compound is used as a curing accelerator to be added into a raw material composition, and the thiol-free coupling agent is added and the proportion of raw material components is controlled, so that the prepared epoxy plastic package material is odorless and environment-friendly, has higher copper adhesion and higher reliability in the application process of a semiconductor.
Detailed Description
The following describes specific embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
The inventor finds that tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene react under certain conditions to generate an organophosphorus compound, the obtained organophosphorus compound is used as a curing accelerator to be added into a raw material composition, and the prepared epoxy molding compound is odorless and environment-friendly, has higher copper adhesion force and has higher reliability in the application process of semiconductors by adding a mercapto-free coupling agent and controlling the proportion of raw material components.
In a first aspect, the present invention provides a process for preparing an organophosphorus compound, which comprises: under the existence of alkaline solution and organic solvent, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene undergo complexation reaction.
In the method of the present invention, in a specific embodiment, the alkaline solution may be one or more of sodium hydroxide, potassium hydroxide, calcium hydroxide and sodium carbonate.
In the method of the present invention, in a specific embodiment, the organic solvent may be one or more of methanol, toluene, methylene chloride and methyltetrahydrofuran.
In the method of the present invention, in a specific embodiment, the molar ratio of the tetraphenylphosphine bromide to the amount of the 2, 3-dihydroxynaphthalene is 1 to 5:2-8, for example, can be 1: 2. 3: 4. 3: 5. 4:7 or 5:8.
in the method of the present invention, in a specific embodiment, the conditions of the complexation reaction include: the reaction temperature is 5-20deg.C, for example, 5 deg.C, 8 deg.C, 10 deg.C, 13 deg.C, 16 deg.C or 20deg.C, and the reaction time is 1-4h, for example, 1h, 1.5h, 2h, 3h or 4h.
In a specific embodiment of the method of the present invention, the reaction formula for preparing the organophosphorus compound includes:
in a second aspect, the present invention provides an epoxy molding compound prepared from a raw material composition comprising 3 to 15% by weight of an epoxy resin, 2 to 10% by weight of a phenolic resin (curing agent), 0.05 to 2.0% by weight of a curing accelerator, 70 to 90% by weight of a filler, 0.1 to 1.2% by weight of a mold release agent, 0.2 to 1.4% by weight of a toughening agent, 0.3 to 2% by weight of a coupling agent and 0 to 2% by weight of a colorant, based on 100% by weight of the total weight of the raw material composition for preparing the epoxy molding compound,
wherein the coupling agent is a mercapto-free coupling agent, and the curing accelerator contains the organic phosphorus compound A and optionally one or more than two of tertiary amine compounds, organic phosphorus compounds B and imidazole compounds.
In the epoxy molding compound of the invention, in a specific embodiment, the organic phosphorus compound A is a compound shown in a formula (1),
wherein, the liquid crystal display device comprises a liquid crystal display device,
is ligand (L)>
Is a central ion.
In a specific embodiment, the content of the organic phosphorus compound a is 5 to 100 wt%, for example, may be 5 wt%, 10.5 wt%, 17 wt%, 24 wt%, 31 wt%, 40 wt%, 50 wt%, 64 wt%, 80 wt%, 90 wt%, or 100 wt%, based on 100 wt% of the total weight of the curing accelerator.
In the epoxy molding compound according to the present invention, in a preferred embodiment, the tertiary amine compound is selected from one or more of 2,4, 6-tris (dimethylaminomethyl) phenol, 1, 8-diazabicyclo (5, 4, 0) undec-7-ene and triethylamine benzyl dimethylamine.
In the epoxy molding compound of the present invention, in a preferred embodiment, the organic phosphorus compound B is selected from one or more of triphenylphosphine, triethylphosphine, trimethylphosphine, tributylphosphine, and tri (p-tolyl) phosphine.
In the epoxy molding compound, in a preferred embodiment, the imidazole compound is selected from one or more of 2-methylimidazole, 2, 4-dimethylimidazole, 2-ethyl 4-methylimidazole, 2-phenyl-4, 5-dihydroxymethylimidazole, 2-heptadecylimidazole and 3-amino-1, 2, 4-triazole.
In the epoxy molding compound, in the specific embodiment, the mercapto-free coupling agent is selected from one or more than two of gamma-glycidyl ether oxypropyl trimethoxy silane, gamma-glycidyl ether trimethoxy silane, gamma-aminopropyl triethoxy silane, gamma-aminopropyl trimethoxy silane, 2- (3, 4-epoxycyclohexane) ethyl trimethoxy silane and N-phenyl-3-aminopropyl trimethoxy siloxane.
In the epoxy molding compound, in a specific embodiment, the toughening agent is selected from one or more than two of methyl methacrylate-butadiene-styrene terpolymer, acrylonitrile-butadiene-styrene copolymer, chlorinated polyethylene and ethylene-vinyl acetate copolymer.
In the epoxy molding compound of the present invention, the epoxy resin is a conventional choice in the art. In a preferred embodiment, the epoxy resin is one or two or more selected from the group consisting of o-cresol formaldehyde epoxy resin, bisphenol a type epoxy resin, bisphenol F type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, aliphatic glycidyl ether epoxy resin and heterocyclic epoxy resin.
In the epoxy molding compound of the present invention, the phenolic resin is a conventional choice in the art. In a preferred embodiment, the phenolic resin is selected from one or more of phenol novolac resin and its derivatives, a condensate of para-xylene and phenol, a condensate of para-xylene and naphthol, a copolymer of dicyclopentadiene and phenol, cresol novolac resin and its derivatives, and monohydroxy or dihydroxynaphthalene novolac resin and its derivatives.
In the epoxy molding compound of the present invention, the filler is a conventional choice in the art. In a preferred embodiment, the filler is selected from one or more of alumina, titania, silicon nitride and silica. In a more preferred embodiment, the median diameter of the filler is from 5 to 80 μm. In a further preferred embodiment, the silica is crystalline silica and/or fused silica.
In the epoxy molding compound of the present invention, the release agent is a conventional choice in the art. In a preferred embodiment, the release agent is selected from one or more of polyethylene wax, carnauba wax, synthetic wax, and mineral wax.
In the epoxy molding compound of the present invention, the colorant is a conventional choice in the art. In a preferred embodiment, the colorant is selected from one or more of titanium dioxide, zinc oxide and carbon black.
The preparation method of the epoxy plastic packaging material is a conventional choice in the field, and the specific preparation method can comprise the following steps: all the components weighed according to the specific proportion are crushed and uniformly mixed at room temperature, then are melted and mixed, crushed and mixed to obtain the epoxy resin composition.
In the present invention, the apparatus used for the melt-kneading may be selected conventionally in the art, and may be, for example, a twin-roll mill, a single-screw extruder, a twin-screw extruder, a kneader or a stirrer.
The present invention will be described in detail by way of examples, but the scope of the present invention is not limited thereto.
The reagents used in the examples and comparative examples of the present invention were all commercially available products unless otherwise specified.
A1 epoxy resin: biphenol epoxy resin, manufacturer: nippon Kayaku co.ltd., brand: NC3000;
b1 phenolic resin: biphenyl type aralkyl phenolic resin, manufacturer: (Meiwa Plastic Industries, ltd.,. Trade name.: MEH-7851ss;
c1 curing accelerator: the organic phosphorus compound has a chemical formula shown in a formula (1),
c2 cure accelerator: 3-amino-1, 2, 4-triazole, manufacturer: aladin, brand: ATA;
d, filling: silica, manufacturer: jiangsu bian Rui, d50 is 22 μm;
e release agent: carnauba wax, manufacturer: shanghai Yiba chemical raw materials Co., ltd., brand: t3;
f toughening agent: methyl methacrylate-butadiene-styrene terpolymer, manufacturer: shenzhen City win plastic raw materials Co., ltd., brand: MBS;
g1 coupling agent: gamma-glycidoxypropyl trimethoxysilane, manufacturer: daokanning, brand: z-6040;
g2 coupling agent: n-phenyl-3-aminopropyl trimethoxysiloxane, manufacturer: daokanning, brand: y-9669;
g3 coupling agent: 2- (3, 4-epoxycyclohexane) ethyltrimethoxysilane, manufacturer: nanjing energy de chemical Co., ltd., brand: KH566;
h colorant: carbon black, manufacturer: hengde chemical Co., ltd.
Examples C1 and comparative examples C1-1 to C1-2 illustrate the preparation of the organophosphorus compounds
Example C1
The preparation process of the organic phosphorus compound comprises the following steps: in the presence of sodium hydroxide and methanol, 1moL of tetraphenylphosphine bromide and 2moL of 2, 3-dihydroxynaphthalene are subjected to complexation reaction to generate an organophosphorus compound C1.
Comparative example C1-1
1moL of tetraphenylphosphine bromide and 2moL of 2, 3-dihydroxynaphthalene are subjected to complexation reaction in the presence of sodium hydroxide to generate an organic phosphorus compound C1-1.
Comparative examples C1-2
Tetraphenylphosphine bromide was used directly as C1-2.
Examples 1 to 11 and comparative examples 1 to 11 are for explaining the preparation process of the epoxy molding compound
The raw material components of examples 1 to 11 and comparative examples 1 to 11 were compounded according to tables 1 and 2, respectively, and were carried out according to the following methods:
(1) Weighing the raw material components, mixing the raw material compositions, and carrying out melt mixing on the mixed materials on an open mixer with a main roller at 80 ℃ and a secondary roller at 100 ℃ for 10min;
(2) And (3) cooling and crushing the melt-mixed material obtained in the step (1), and preforming the melt-mixed material into a cake material to obtain the epoxy molding compound.
TABLE 1 raw material ratios of examples 1-11
Table 2 raw material ratios of comparative examples 1 to 8
Comparative example 9
The raw material formulation and preparation method were carried out according to example 1, except that the coupling agent was replaced with 0.75g of 3-mercaptopropyl trimethoxysilane.
Comparative example 10
The raw material mixture ratio and the preparation method of example 1 were carried out except that all C1 was replaced by C1-1.
Comparative example 11
The raw material formulation and preparation method of example 1 were followed except that all C1 was replaced with C1-2.
Test case
Copper adhesion before post-cure and copper adhesion after post-cure:
using a low pressure transfer molding machine at a mold temperature of 175℃and an injection pressure of 60bar and a curing time of 110sThen, the obtained epoxy molding compound is molded on a copper sheet to form a contact area of 176mm 2 And (3) carrying out post-curing on the half-molded epoxy molding compound. Copper adhesion (N) without post-cure and after-cure was tested using a microcomputer controlled electronic universal tester.
The post-curing copper adhesion and post-curing copper adhesion of the epoxy molding compounds prepared in examples 1 to 11 and comparative examples 1 to 11 were tested and the results are shown in Table 3.
TABLE 3 Table 3
As can be seen from the test results of examples 1 to 11 and comparative examples 1 to 11, the epoxy molding compound prepared by using the mercapto-free coupling agent has no pungent smell, and simultaneously, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene are reacted under certain conditions to generate an organic phosphorus compound as a curing accelerator to be added into the raw material composition, and the proportion among the raw material components is controlled, so that the prepared epoxy molding compound has higher copper adhesion and higher reliability in the application process of a semiconductor.
The foregoing is merely exemplary embodiments of the present invention and are not intended to limit the scope of the present invention, and all equivalent modifications made by the present invention or direct or indirect application in other related technical fields are included in the scope of the present invention.
Claims (10)
1. A method of preparing an organophosphorus compound, said method comprising: under the existence of alkaline solution and organic solvent, tetraphenylphosphine bromide and 2, 3-dihydroxynaphthalene undergo complexation reaction.
2. The method according to claim 1, wherein the molar ratio of tetraphenylphosphine bromide to the amount of 2, 3-dihydroxynaphthalene used is from 1 to 5:2-8.
3. The method according to claim 1 or 2, wherein the conditions of the complexation reaction comprise: the reaction temperature is 5-20 ℃ and the reaction time is 1-4h.
4. An epoxy molding compound is characterized in that the epoxy molding compound is prepared from a raw material composition containing 3-15 wt% of epoxy resin, 2-10 wt% of phenolic resin, 0.05-2.0 wt% of curing accelerator, 70-90 wt% of filler, 0.1-1.2 wt% of release agent, 0.2-1.4 wt% of toughening agent, 0.3-2 wt% of coupling agent and 0-2 wt% of colorant based on 100 wt% of the total weight of the raw material composition for preparing the epoxy molding compound,
wherein the coupling agent is a mercapto-free coupling agent, and the curing accelerator contains an organic phosphorus compound A prepared by the method of claims 1-3 and one or more than two selected from a tertiary amine compound, an organic phosphorus compound B and an imidazole compound.
5. The epoxy molding compound according to claim 4, wherein the content of the organic phosphorus compound A is 5 to 100% by weight based on 100% by weight of the total weight of the curing accelerator.
6. The epoxy molding compound according to claim 4 or 5, wherein the tertiary amine compound is one or more selected from the group consisting of 2,4, 6-tris (dimethylaminomethyl) phenol, 1, 8-diazabicyclo (5, 4, 0) undec-7-ene and triethylamine benzyl dimethylamine;
preferably, the organophosphorus compound B is selected from one or more of triphenylphosphine, triethylphosphine, trimethylphosphine, tributylphosphine and tri (p-tolyl) phosphine;
preferably, the imidazole compound is selected from one or more than two of 2-methylimidazole, 2, 4-dimethylimidazole, 2-ethyl 4-methylimidazole, 2-phenyl-4, 5-dihydroxymethylimidazole, 2-heptadecylimidazole and 3-amino-1, 2, 4-triazole.
7. The epoxy molding compound according to claim 4 or 6, wherein the mercapto-free coupling agent is one or more selected from the group consisting of gamma-glycidoxypropyl trimethoxysilane, gamma-glycidoxypropyl ether trimethoxysilane, gamma-aminopropyl triethoxysilane, gamma-aminopropyl trimethoxysilane, 2- (3, 4-epoxycyclohexane) ethyl trimethoxysilane and N-phenyl-3-aminopropyl trimethoxysiloxane.
8. The epoxy molding compound of claim 4 or 6, wherein the toughening agent is one or more selected from the group consisting of methyl methacrylate-butadiene-styrene terpolymer, acrylonitrile-butadiene-styrene copolymer, chlorinated polyethylene and ethylene-vinyl acetate copolymer.
9. The epoxy molding compound according to claim 4 or 6, wherein the filler has a median diameter of 5 to 80 μm.
10. Use of the epoxy molding compound of claims 4-9 as a semiconductor packaging material.
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| CN202211713296.2A CN116023411A (en) | 2022-12-29 | 2022-12-29 | Preparation method of organic phosphorus compound, epoxy plastic packaging material and application thereof |
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| CN202211713296.2A CN116023411A (en) | 2022-12-29 | 2022-12-29 | Preparation method of organic phosphorus compound, epoxy plastic packaging material and application thereof |
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