CN115216264A - Preparation method of polyamide acid coating adhesive for power semiconductor packaging - Google Patents
Preparation method of polyamide acid coating adhesive for power semiconductor packaging Download PDFInfo
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- CN115216264A CN115216264A CN202210987718.9A CN202210987718A CN115216264A CN 115216264 A CN115216264 A CN 115216264A CN 202210987718 A CN202210987718 A CN 202210987718A CN 115216264 A CN115216264 A CN 115216264A
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- polyamic acid
- power semiconductor
- aromatic diamine
- acid coating
- diamine containing
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 78
- 239000011248 coating agent Substances 0.000 title claims abstract description 71
- 238000000576 coating method Methods 0.000 title claims abstract description 71
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 51
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 49
- 239000000853 adhesive Substances 0.000 title claims abstract description 45
- 239000004952 Polyamide Substances 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 title claims abstract description 15
- 229920002647 polyamide Polymers 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 86
- 239000000758 substrate Substances 0.000 claims abstract description 40
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 35
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000080 wetting agent Substances 0.000 claims abstract description 33
- -1 siloxane chain Chemical group 0.000 claims abstract description 23
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- 239000012046 mixed solvent Substances 0.000 claims description 18
- 239000003292 glue Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000005538 encapsulation Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 238000010292 electrical insulation Methods 0.000 abstract description 2
- 239000011241 protective layer Substances 0.000 abstract description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 9
- 239000004642 Polyimide Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 229920001721 polyimide Polymers 0.000 description 9
- RTJIRNGSUCHETG-UHFFFAOYSA-N 4-[(4-aminophenoxy)-diphenylsilyl]oxyaniline Chemical compound C1=CC(N)=CC=C1O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)OC1=CC=C(N)C=C1 RTJIRNGSUCHETG-UHFFFAOYSA-N 0.000 description 8
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000004100 electronic packaging Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical class C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- IYTXQZMZTQHONB-UHFFFAOYSA-N 4-[(4-aminophenoxy)-dimethylsilyl]oxyaniline Chemical compound C=1C=C(N)C=CC=1O[Si](C)(C)OC1=CC=C(N)C=C1 IYTXQZMZTQHONB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 238000007719 peel strength test Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
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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
- C08G2170/00—Compositions for adhesives
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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
- C08G2190/00—Compositions for sealing or packing joints
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Electromagnetism (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
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Abstract
A polyamide acid coating adhesive for power semiconductor packaging and a preparation method thereof, raw materials comprise aromatic diamine containing siloxane chain segments, aromatic diamine containing amide bonds, aliphatic ring dianhydride and substrate wetting agent, wherein the molar ratio of the aromatic diamine containing siloxane chain segments to the aromatic diamine containing amide bonds is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane chain segment and the aromatic diamine containing the amide bond to the aliphatic cyclic dianhydride is 1.00 (0.98-1.00). The polyamic acid coating adhesive for packaging the power semiconductor is mainly formed by copolymerizing aromatic diamine containing siloxane chain segments, aromatic diamine containing amide bonds and aliphatic cyclic dianhydride, and the aromatic diamine ensures that a protective layer obtained after the polyamic acid is thermally imidized has better mechanical strength, heat resistance and electrical insulation performance.
Description
Technical Field
The invention belongs to the technical field of coating adhesives, and particularly relates to a preparation method of a polyamide acid coating adhesive for power semiconductor packaging.
Background
The polyamic acid coating glue for packaging the power semiconductor has excellent physical and chemical properties of polyimide after thermal imidization, has good bonding property for materials such as silicon wafers, aluminum, copper, glass or ceramics and the like, can be coated on the surface of an electronic component to be used as a protective coating, and can be bonded with a composite material and common metal materials such as aluminum alloy, stainless steel and the like. However, the polyamic acid coating adhesive for power semiconductor packaging produced in China at present has certain defects in heat resistance, adhesive property and long-term reliability guarantee of electronic devices.
In the patent with the application number of 201210548934, a preparation method of a polyimide adhesive is provided, wherein aromatic diamine BAPP, ODA and aromatic dianhydride alpha-ODPA are selected to react to generate a polyamic acid solution, and PI powder is prepared through chemical imidization. The PI powder greatly reduces the curing temperature (only 170-200 ℃), improves the temperature resistance level (210-230 ℃), and is not easy to generate bubbles or form gaps in the adhesive layer. However, the test results show that the adhesive strength of the adhesive is relatively general with copper, aluminum, platinum, stainless steel and the like, and the adhesive can be initially used and popularized in the microelectronic field with low requirements on the adhesive property, but is difficult to be applied in the microelectronic field with more strict requirements on the adhesive property.
Patent application No. 201210191649 provides an adhesive film for a semiconductor that can be attached to a semiconductor wafer at low temperature, can sufficiently suppress the occurrence of chip cracks or burrs, and can produce semiconductor chips from the semiconductor wafer at a good yield. In this document, the polyamic acid resin contained in the adhesive film for a semiconductor is obtained by reacting s-ODPA and other tetracarboxylic dianhydrides with a siloxane diamine. The glass transition temperature of the polyamic acid resin is within the range of 30-80 ℃, the low-temperature attaching process can be well realized, but the polyamic acid resin has poor heat resistance and is limited in application in the high-temperature process stage of processing a subsequent chip into a device.
In patent application No. 200810135764, there is concerned a resin for optical semiconductor element encapsulation comprising a polyimide obtained by imidizing a polyimide precursor obtained by polycondensing a fatty acid dianhydride with an aliphatic or aromatic diamine compound; and to an optical semiconductor device comprising the resin and an optical semiconductor element encapsulated with the resin. The resin for optical semiconductor element encapsulation according to the present invention has high light transmission characteristics, excellent heat resistance, and excellent light resistance even with short-wavelength light, but the adhesive properties of the resin are general, and the range of application thereof is limited.
The patent with the application number of 201010561806 discloses a polyimide electronic packaging material and a synthesis method thereof, wherein the polyimide electronic packaging material is prepared by dissolving 2, 3',4' -biphenyltetracarboxylic dianhydride and 2,2' -bis (trifluoromethyl) -4, 4-diaminodiphenyl sulfide in an aprotic polar solvent in an equimolar ratio and reacting at the temperature of 10-20 ℃ to prepare polyamic acid; and then putting the prepared polyamic acid into an oven to perform imidization according to the following procedures: and (3) cooling at 80 ℃/3h, 150 ℃/1h, 180 ℃/1h, 250 ℃/1h, 300 ℃/1h and 350 ℃/15min naturally to obtain the electronic packaging polyimide material. The material has the properties of high light transmittance, low water absorption, excellent mechanical property, high temperature resistance and the like, but the glass transition temperature of the material is generally higher than 280 ℃, and the problem of incomplete thermal imidization possibly exists in the process of an electronic packaging process, so that the yield and the production efficiency of electronic devices are influenced.
Disclosure of Invention
The technical problem to be solved by the present invention is to provide a method for preparing polyamic acid coating glue for power semiconductor package, which overcomes the disadvantages and shortcomings mentioned in the background art.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the polyamide acid coating adhesive for power semiconductor packaging comprises raw materials of aromatic diamine containing siloxane chain segments, aromatic diamine containing amide bonds and aliphatic cyclic dianhydride, wherein the molar ratio of the aromatic diamine containing siloxane chain segments to the aromatic diamine containing amide bonds is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane chain segment and the aromatic diamine containing the amide bond to the aliphatic cyclic dianhydride is 1.00 (0.98-1.00).
Preferably, the siloxane segment-containing aromatic diamine comprises one or more of the following:
preferably, the aromatic diamine containing an amide bond includes one or more of:
preferably, the aliphatic cyclic dianhydride comprises one or more of the following:
under the same inventive concept, the invention also provides a preparation method of the polyamic acid coating adhesive for packaging the power semiconductor, which comprises the following steps:
(1) Dissolving aromatic diamine containing siloxane chain segments and aromatic diamine containing amide bonds in a mixed solvent;
(2) Adding aliphatic cyclic dianhydride into the system obtained in the step (1) for reaction at the temperature of 30-45 ℃ for 6-8h to obtain polyamic acid resin;
(3) And (3) after the reaction in the step (2) is finished, adding a substrate wetting agent into the reaction product, and stirring for 0.5-1.0 h to uniformly disperse the substrate wetting agent in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Preferably, in the step (1), the solvent is dissolved in the mixed solvent under an inert gas atmosphere.
Preferably, in the step (1), the mixed solvent is a mixed solvent of a polar aprotic solvent and a ketone solvent in a mass ratio of (2.0 to 8.0): 1.0.
Preferably, the polar aprotic solvent is selected from one or more of dimethylformamide, dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide, and the ketone solvent is selected from one or more of methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and isophorone.
Preferably, the addition amount of the mixed solvent accounts for 80.0-90.0% of the mass of the polyamic acid coating glue for power semiconductor packaging; the total adding amount of the diamine monomer and the dianhydride monomer accounts for 10.0-20.0% of the mass of the polyamic acid coating adhesive for power semiconductor packaging.
Preferably, in the step (3), the substrate wetting agent is selected from one or more of TEGO Wet 245, TEGO Wet 270, TEGO Wet280, TEGO Wet500, TEGO Twin 4000, TEGO Twin 4100 and TEGO Twin 4200, and the addition amount is 0.1-2.0% of the mass of the polyamic acid coating glue for power semiconductor packaging.
The substrate wetting agent can further improve the bonding strength between the polyamide acid coating adhesive for packaging the power semiconductor and the substrate, remarkably improve the yield of electrical devices and reduce the production cost.
Compared with the prior art, the invention has the following beneficial effects:
(1) The polyamic acid coating adhesive for packaging the power semiconductor is mainly formed by copolymerizing aromatic diamine containing siloxane chain segments, aromatic diamine containing amide bonds and aliphatic cyclic dianhydride, wherein the aromatic diamine ensures that a protective layer obtained after the polyamic acid is thermally imidized has better mechanical strength, heat resistance and electrical insulation performance; the aliphatic cyclic dianhydride and the aromatic diamine monomer containing the siloxane chain segment have side group structures, and under the combined action of the aliphatic cyclic dianhydride and the aromatic diamine monomer, the stacking regularity among polyamic acid molecular chains can be weakened to a certain extent, so that the glass transition temperature of the obtained polyamic acid coating adhesive for power semiconductor packaging can be reduced, the complete curing at a lower temperature (240-280 ℃) is realized, the complete thermal imidization of the polyamic acid coating adhesive for power semiconductor device packaging is ensured, and the yield and the production efficiency of the power semiconductor device are ensured;
(2) The main chain of the polyamide acid coating adhesive molecule obtained by random copolymerization of different diamines and dianhydrides contains a large amount of ketone groups and siloxane groups, so that the polyamide acid coating adhesive has good bonding strength with different substrate materials such as nickel, aluminum nitride, silicon carbide and the like on the molecular level;
(3) The polyamic acid coating adhesive for power semiconductor packaging can be completely cured at a lower temperature (240-280 ℃), and simultaneously shows excellent mechanical strength, heat resistance, electric insulation performance and substrate adhesion performance after being cured, thereby realizing good packaging of a power semiconductor, protecting the interconnection in a device, preventing the device from mechanical and chemical damage, and improving the long-term operation reliability and stability of the power semiconductor device.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a schematic diagram of tensile shear strength test of a polyamic acid coating paste for power semiconductor packaging;
fig. 2 is a schematic diagram of a T peel strength test of the polyamic acid coating paste for power semiconductor packaging.
Detailed Description
In order to facilitate an understanding of the invention, reference will now be made in detail to the present preferred embodiments of the invention, examples of which are illustrated in the accompanying drawings, and the scope of the invention is not limited to the following specific embodiments.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present invention.
Unless otherwise specifically indicated, various raw materials, reagents, instruments, equipment and the like used in the present invention are commercially available or can be prepared by existing methods.
Example 1:
a polyamic acid coating adhesive for power semiconductor packaging comprises raw materials of bis (4-aminophenoxy) dimethylsilane, 4' -diaminobenzanilide, cyclobutane dianhydride and a substrate wetting agent.
A preparation method of polyamic acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.37 g) of bis (4-aminophenoxy) dimethylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (106.53g of DMF +26.63g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (10.78 g) of cyclobutane dianhydride is added into the system obtained after the step (1) for reaction, and the reaction time is 6 hours, so that polyamic acid resin is obtained;
(3) After the reaction in the step (2) is finished, adding 1.50g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Twin in the polyamic acid resin, thereby obtaining the polyamic acid coating adhesive for packaging the power semiconductor.
Example 2:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) diisopropylsilane, 4' -diaminobenzanilide, cyclobutane dianhydride and a substrate wetting agent.
A preparation method of polyamide acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.53 g) of bis (4-aminophenoxy) diisopropylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (107.26gDMF +26.81g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (10.78 g) of cyclobutane dianhydride is added into the system obtained after the step (1) for reaction, and the reaction time is 6 hours, so that polyamic acid resin is obtained;
(3) After the reaction in the step (2) is finished, adding 1.50g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Twin in the polyamic acid resin, thereby obtaining the polyamic acid coating adhesive for packaging the power semiconductor.
Example 3:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) di-tert-butyl silane, 4' -diaminobenzanilide, cyclobutane dianhydride and a substrate wetting agent.
A preparation method of polyamide acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.67 g) of bis (4-aminophenoxy) di-tert-butylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (107.89g of DMF +26.97g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (10.78 g) of cyclobutane dianhydride is added into the system after the step (1) for reaction, and the reaction time is 6h, so that polyamic acid resin is obtained;
(3) After the reaction in the step (2) is finished, adding 1.50g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Twin in the polyamic acid resin, thereby obtaining the polyamic acid coating adhesive for packaging the power semiconductor.
Example 4:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) dicyclopentylsilane, 4' -diaminobenzanilide, methyl isobutyl ketone and a substrate wetting agent.
A preparation method of polyamic acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.91 g) of bis (4-aminophenoxy) dicyclopentylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (108.98g of DMF +27.25g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (10.78 g) of cyclobutane dianhydride is added into the system after the step (1) for reaction, and the reaction time is 6h, so that polyamic acid resin is obtained;
(3) After the reaction in the step (2) is finished, adding 1.50g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Twin in the polyamic acid resin, thereby obtaining the polyamic acid coating adhesive for packaging the power semiconductor.
Example 5:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) diphenylsilane, 4' -diaminobenzanilide, cyclobutane dianhydride and a substrate wetting agent.
A preparation method of polyamic acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (109.34g of DMF +27.34g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (10.78 g) of cyclobutane dianhydride is added into the system obtained after the step (1) for reaction, and the reaction time is 6 hours, so that polyamic acid resin is obtained;
(3) After the reaction in the step (2) is finished, 1.50g of substrate wetting agent TEGO Twin 4000 is added into the reaction product, and then the mixture is stirred for 1.0h to be uniformly dispersed in the polyamic acid resin, so that the polyamic acid coating adhesive for power semiconductor packaging is obtained.
Example 6:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) diphenylsilane, 4' -diaminobenzanilide, cyclohexane dianhydride and a substrate wetting agent.
A preparation method of polyamic acid coating glue for power semiconductor packaging comprises the following steps:
(1) Under the nitrogen atmosphere, 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide are dissolved in a mixed solvent (116.33g of DMF +29.08g of methyl isobutyl ketone);
(2) The reaction temperature is 35 ℃, 0.055mol (12.32 g) of cyclohexane dianhydride is added into the system obtained after the step (1) for reaction, and the reaction time is 6 hours, so that polyamide acid resin is obtained;
(3) After the reaction in the step (2) is finished, adding 1.50g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Twin in the polyamic acid resin, thereby obtaining the polyamic acid coating adhesive for packaging the power semiconductor.
Example 7:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) diphenylsilane, 4' -diaminobenzanilide, cyclohexane dianhydride and a substrate wetting agent.
A preparation method of polyamide acid coating glue for power semiconductor packaging comprises the following steps:
(1) Dissolving 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide in a mixed solvent (116.33gDMF +29.08g of methyl isobutyl ketone) under a nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.055mol (12.32 g) of cyclohexane dianhydride is added into the system after the step (1) for reaction, and the reaction time is 6h, so that the polyamic acid resin is obtained;
(3) And (3) after the reaction in the step (2) is finished, adding 2..00g of substrate wetting agent TEGO Twin 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the mixture in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 8:
a polyamic acid coating adhesive for packaging a power semiconductor comprises raw materials of bis (4-aminophenoxy) diphenylsilane, 4' -diaminobenzanilide, cyclohexane dianhydride and a substrate wetting agent.
A preparation method of polyamide acid coating glue for power semiconductor packaging comprises the following steps:
(1) Under the nitrogen atmosphere, 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane and 0.05mol (11.35 g) of 4,4' -diaminobenzanilide are dissolved in a mixed solvent (116.33g of DMF +29.08g of methyl isobutyl ketone);
(2) The reaction temperature is 35 ℃, 0.055mol (12.32 g) of cyclohexane dianhydride is added into the system obtained after the step (1) for reaction, and the reaction time is 6 hours, so that polyamide acid resin is obtained;
(3) After the reaction in the step (2) is finished, 1.50g of substrate wetting agent TEGO Wet 245 is added into the reaction product, and then stirring is carried out for 1.0h, so that the substrate wetting agent TEGO is uniformly dispersed in the polyamic acid resin, and the polyamic acid coating adhesive for power semiconductor packaging is obtained.
Comparative example 1:
preparation of a PMDA/ODA series polyamic acid resin, comprising the following steps:
(1) Dissolving 0.10mol (20.02 g) of ODA in a mixed solvent (189.63g DMF +47.41g methyl isobutyl ketone) under nitrogen atmosphere;
(2) At the reaction temperature of 35 ℃, adding 0.10mol (21.81 g) of PMDA into the system obtained in the step (1) for reaction for 6 hours to obtain polyamic acid resin;
(3) After the reaction in the step (2) is finished, 1.50g of substrate wetting agent TEGO Wet 245 is added into the reaction product, and then stirred for 1.0h to uniformly disperse the substrate wetting agent TEGO Wet in the polyamic acid resin, so that the PMDA/ODA series polyamic acid resin is obtained.
The method shown in figure 1 is adopted to carry out tensile shear strength test of the polyamic acid coating adhesive for power semiconductor packaging, and the tensile property of two substrates after the two substrates are partially bonded through the polyimide coating adhesive is detected; the T peel strength test of the polyamic acid coating adhesive for power semiconductor encapsulation was performed by the method shown in fig. 2, and the peel strength of two substrates bonded by the polyimide coating adhesive was examined, and the test results are shown in the following table.
Table 1 shows the viscosity test results of the polyamic acid coating pastes for power semiconductor packages prepared in examples 1 to 8, and it can be seen from table 1 that the polyamic acid coating pastes for power semiconductor packages prepared according to the present invention have suitable viscosity, good fluidity, and good leveling property, and are not likely to generate bubbles when coated on a substrate or a product.
Table 2 shows the performance data of films having a thickness of 20 to 25 μm, which were obtained by thermal imidization of the polyamic acid coating paste for power semiconductor packages prepared in examples 1 to 8.
Table 1 polyamic acid coating paste viscosity test method for power semiconductor package: tested according to GB/T2794-1995 standard.
The film-related property test methods in table 2:
T g : tested according to HB 7655-1999;
insulating strength: testing according to GB/T1408.1-2016;
tensile strength and elongation: testing according to GB/T1040.3-2006 standard;
tensile shear strength: testing according to GB/T7124-2008 standard;
t peel strength: tested according to GB/T2791-1995 standard.
TABLE 1 viscosity of polyamic acid coating paste for power semiconductor encapsulation
TABLE 2 film related Performance data
Claims (10)
1. The polyamide acid coating adhesive for packaging the power semiconductor is characterized in that raw materials comprise aromatic diamine containing siloxane chain segments, aromatic diamine containing amide bonds, aliphatic ring dianhydride and a substrate wetting agent, wherein the molar ratio of the aromatic diamine containing the siloxane chain segments to the aromatic diamine containing the amide bonds is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane chain segment and the aromatic diamine containing the amide bond to the aliphatic cyclic dianhydride is 1.00 (0.98-1.00).
2. The polyamic acid coating paste for power semiconductor encapsulation according to claim 1, wherein the aromatic diamine containing a siloxane segment comprises one or more of the following:
3. the polyamic acid coating paste for power semiconductor encapsulation according to claim 1, wherein the aromatic diamine containing amide bond comprises one or more of:
4. the polyamic acid coating paste for power semiconductor encapsulation according to claim 1, wherein the aliphatic cyclic dianhydride comprises one or more of the following:
5. a method for preparing polyamic acid coating glue for power semiconductor package according to any one of claims 1 to 4, comprising the steps of:
(1) Dissolving aromatic diamine containing siloxane chain segments and aromatic diamine containing amide bonds in a mixed solvent;
(2) Adding alicyclic dianhydride into the system obtained in the step (1) for reaction at the temperature of 30-45 ℃ for 6-8 hours to obtain polyamic acid resin;
(3) And (3) after the reaction in the step (2) is finished, adding a substrate wetting agent into the reaction product, and stirring for 0.5-1.0 h to uniformly disperse the substrate wetting agent in the polyamic acid resin to obtain the polyamic acid coating adhesive for power semiconductor packaging.
6. The method of preparing polyamic acid coating paste for power semiconductor package according to claim 5, wherein in step (1), the solvent mixture is in inert gas atmosphere.
7. The method for preparing polyamic acid coating paste for power semiconductor encapsulation according to claim 5, wherein in step (1), the mixed solvent is a mixed solvent of polar aprotic solvent and ketone solvent in a mass ratio of (2.0-8.0): 1.0.
8. The method for preparing polyamic acid coating paste for power semiconductor encapsulation according to claim 7, wherein said polar aprotic solvent is selected from one or more of dimethylformamide, dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide, and said ketone solvent is selected from one or more of methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and isophorone.
9. The method for preparing polyamic acid coating glue for power semiconductor package according to claim 7 or 8, wherein the addition amount of the mixed solvent accounts for 80.0-90.0% of the mass of polyamic acid coating glue for power semiconductor package; the total adding amount of the diamine monomer and the dianhydride monomer accounts for 10.0-20.0% of the mass of the polyamic acid coating adhesive for packaging the power semiconductor.
10. The method for preparing polyamic acid coating paste for power semiconductor packaging according to claim 5, wherein in step (3), the substrate wetting agent is selected from one or more of TEGO Wet 245, TEGO Wet 270, TEGO Wet280, TEGO Wet500, TEGO Twin 4000, TEGO Twin 4100, and TEGO Twin 4200, and the addition amount is 0.1-2.0% of the mass of polyamic acid coating paste for power semiconductor packaging.
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