CN115216264B - 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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- CN115216264B CN115216264B CN202210987718.9A CN202210987718A CN115216264B CN 115216264 B CN115216264 B CN 115216264B CN 202210987718 A CN202210987718 A CN 202210987718A CN 115216264 B CN115216264 B CN 115216264B
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- power semiconductor
- aromatic diamine
- acid coating
- diamine containing
- polyamide acid
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 75
- 239000011248 coating agent Substances 0.000 title claims abstract description 68
- 238000000576 coating method Methods 0.000 title claims abstract description 68
- 239000004952 Polyamide Substances 0.000 title claims abstract description 59
- 239000002253 acid Substances 0.000 title claims abstract description 59
- 229920002647 polyamide Polymers 0.000 title claims abstract description 59
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 56
- 239000000853 adhesive Substances 0.000 title claims abstract description 54
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title description 15
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 35
- 239000000080 wetting agent Substances 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 34
- 239000000758 substrate Substances 0.000 claims abstract description 34
- -1 siloxane chain Chemical group 0.000 claims abstract description 20
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 12
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 229920005575 poly(amic acid) Polymers 0.000 claims description 38
- 239000011347 resin Substances 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 239000012046 mixed solvent Substances 0.000 claims description 17
- 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
- 238000003756 stirring Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000003292 glue Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 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
- 239000002904 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
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 238000010292 electrical insulation Methods 0.000 abstract description 3
- 239000011241 protective layer Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 11
- 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
- 230000035484 reaction time Effects 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 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
- 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
- 125000001931 aliphatic group Chemical group 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
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007547 defect Effects 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
- 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
- 239000000126 substance Substances 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
- 238000010521 absorption reaction Methods 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 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
- 239000010410 layer Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000012858 packaging process Methods 0.000 description 1
- 238000011056 performance test Methods 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
- 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
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test 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
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- 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)
- Power Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The polyamide acid coating adhesive for packaging the power semiconductor comprises raw materials including aromatic diamine containing a siloxane chain segment, aromatic diamine containing an amide bond, alicyclic dianhydride and a substrate wetting agent, wherein the molar ratio of the aromatic diamine containing the siloxane chain segment to the aromatic diamine containing the amide bond is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane segment and the aromatic diamine containing the amide bond to the alicyclic dianhydride is 1.00 (0.98-1.00). The polyamide 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 alicyclic dianhydride, and the aromatic diamine ensures that a protective layer obtained after polyamide acid thermal imidization has better mechanical strength, heat resistance and electrical insulation property.
Description
Technical Field
The invention belongs to the technical field of coating glue, and particularly relates to a preparation method of polyamide acid coating glue for power semiconductor packaging.
Background
The polyamide acid coating gel for packaging the power semiconductor has excellent physical and chemical properties of polyimide after thermal imidization, and has good bonding performance on materials such as silicon chips, aluminum, copper, glass or ceramics, and the like, can be coated on the surface of electronic components to be used as a protective coating, and can be used for bonding composite materials, aluminum alloy, stainless steel and other common metal materials. However, the polyamic acid coating glue for packaging power semiconductors produced at home at present has certain defects in heat resistance, adhesive property and long-term reliability guarantee for electronic devices.
In the patent with the application number of 201210548934, a preparation method of a polyimide adhesive is provided, 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 ℃) and improves the temperature resistance level (210-230 ℃), and bubbles or gaps are not easy to generate in the rubber layer. However, the test result shows that the adhesive strength of the adhesive with copper, aluminum, platinum, stainless steel and the like is relatively general, and the adhesive can be preliminarily used and popularized in the microelectronic field with low requirements on the adhesive performance, but is difficult to realize application in the microelectronic field with more severe requirements on the adhesive performance.
In the patent application No. 201210191649, an adhesive film for a semiconductor is provided which can be attached to a semiconductor wafer at a low temperature and can produce semiconductor chips from the semiconductor wafer with a good yield while sufficiently suppressing the occurrence of chip cracks or burrs. The polyamic acid resin contained in the adhesive film for a semiconductor in this document is obtained by reacting s-ODPA and other types of tetracarboxylic dianhydrides with siloxane diamine. The glass transition temperature of the polyamide acid resin is in the range of 30-80 ℃, so that the low-temperature attaching process can be well realized, but the heat resistance is poor, and the application of the polyamide acid resin in the high-temperature process stage of processing a subsequent chip into a device is limited.
Patent application No. 200810135764 relates to 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 an optical semiconductor device comprising the resin and an optical semiconductor element encapsulated with the resin. The resin for encapsulating an optical semiconductor element according to the present invention has high light transmission characteristics, excellent heat resistance, and excellent light resistance even for short wavelength light, but the adhesive property of the resin is generally limited in its application range.
The patent with application number 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' -biphenyl tetracarboxylic dianhydride and 2,2' -bis (trifluoromethyl) -4, 4-diamino diphenyl sulfide in an aprotic polar solvent in an equimolar ratio, and reacting at 10-20 ℃; then the prepared polyamic acid is put into an oven for imidization according to the following procedure: and (3) cooling naturally at 80 ℃/3h, 150 ℃/1h, 180 ℃/1h, 250 ℃/1h, 300 ℃/1h and 350 ℃/15min to obtain the electronic packaging polyimide material. The material has the performances of high light transmittance, low water absorption, excellent mechanical property, high temperature resistance and the like, but the glass transition temperature is generally higher than 280 ℃, and the problem of incomplete thermal imidization can exist in the electronic packaging process, so that the yield and the production efficiency of electronic devices are affected.
Disclosure of Invention
The invention aims to solve the technical problems and overcome the defects in the prior art, and provides a preparation method of polyamide acid coating adhesive for packaging a power semiconductor.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the polyamide acid coating adhesive for packaging the power semiconductor comprises raw materials including aromatic diamine containing a siloxane chain segment, aromatic diamine containing an amide bond and alicyclic dianhydride, wherein the molar ratio of the aromatic diamine containing the siloxane chain segment to the aromatic diamine containing the amide bond is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane segment and the aromatic diamine containing the amide bond to the alicyclic dianhydride is 1.00 (0.98-1.00).
Preferably, the aromatic diamine containing a siloxane segment comprises one or more of the following:
preferably, the aromatic diamine containing an amide bond includes one or more of the following:
preferably, the alicyclic 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 segment and aromatic diamine containing amide bond in mixed solvent;
(2) Adding alicyclic dianhydride into the system obtained in the step (1) to react at the temperature of 30-45 ℃ for 6-8 hours to obtain polyamide acid resin;
(3) After the reaction of the step (2), 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 mixture is under 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) of 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 polyamide acid coating adhesive for packaging the power semiconductor; the total addition amount of the diamine monomer and the dianhydride monomer accounts for 10.0-20.0% of the mass of the polyamide acid coating adhesive for packaging the power semiconductor.
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 Tain 4000, TEGO Tain 4100 and TEGO Tain 4200, and the addition amount is 0.1-2.0% of the mass of the polyamide 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, obviously improve the yield of the electrical device and reduce the production cost.
Compared with the prior art, the invention has the beneficial effects that:
(1) The polyamide 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 alicyclic dianhydride, and the aromatic diamine ensures that a protective layer obtained after polyamide acid thermal imidization has good mechanical strength, heat resistance and electrical insulation property; 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 polyamide acid molecular chains can be weakened to a certain extent, the glass transition temperature of the polyamide acid coating adhesive for packaging the power semiconductor can be reduced, the complete solidification at a lower temperature (240-280 ℃) is realized, the complete thermal imidization of the polyamide acid coating adhesive in the packaging process of the power semiconductor device 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 glue molecule obtained by adopting different diamine and dianhydride through random copolymerization contains a large amount of ketone groups and siloxane groups, so that the polyamide acid coating glue has good bonding strength with different substrate materials such as nickel, aluminum nitride, silicon carbide and the like on the molecular level;
(3) The polyamide acid coating adhesive for packaging the power semiconductor can be completely cured at a lower temperature (240-280 ℃), and simultaneously, the polyamide acid coating adhesive for packaging the power semiconductor shows excellent mechanical strength, heat resistance, electrical insulation performance and substrate adhesion performance after being cured, so that the power semiconductor is well packaged, the interconnection inside the device is protected, the device is prevented from being damaged mechanically and chemically, and the long-term operation reliability and stability of the power semiconductor device are improved.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a schematic diagram showing a tensile shear strength test of a polyamic acid coating paste for power semiconductor packaging;
fig. 2 is a schematic diagram showing T-peel strength test of a polyamic acid coating paste for power semiconductor packaging.
Detailed Description
The present invention will be described more fully hereinafter with reference to the accompanying drawings, in which preferred embodiments are shown, for the purpose of illustrating the invention, but the scope of the invention is not limited to the specific embodiments shown.
Unless defined otherwise, all technical and scientific terms used hereinafter have the same meaning as commonly understood by one of ordinary skill in the art. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the scope of the present invention.
Unless otherwise specifically indicated, the various raw materials, reagents, instruments, equipment and the like used in the present invention are commercially available or may be prepared by existing methods.
Example 1:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) dimethyl silane, 4' -diamino benzanilide, cyclobutane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.37 g) of bis (4-aminophenoxy) dimethylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (106.53 g DMF+26.63g methyl isobutyl ketone) under 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 6 hours, thus obtaining polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 2:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) diisopropyl silane, 4' -diamino benzanilide, cyclobutane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.53 g) of bis (4-aminophenoxy) diisopropylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (107.26 g DMF+26.81g methyl isobutyl ketone) under 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 6 hours, thus obtaining polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 3:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) ditertiary butyl silane, 4' -diamino benzanilide, cyclobutane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.67 g) of bis (4-aminophenoxy) di-t-butylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (107.89 g DMF+26.97g methyl isobutyl ketone) under 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 6 hours, thus obtaining polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 4:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) dicyclopentyl silane, 4' -diamino benzanilide, methyl isobutyl ketone and substrate wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.91 g) of bis (4-aminophenoxy) dicyclopentyl silane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (108.98 g DMF+27.25g methyl isobutyl ketone) under 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 6 hours, thus obtaining polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 5:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) diphenyl silane, 4' -diamino benzanilide, cyclobutane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (109.34 g DMF+27.34g methyl isobutyl ketone) under 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 6 hours, thus obtaining polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 6:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) diphenyl silane, 4' -diamino benzanilide, cyclohexane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (116.33 g DMF+29.08g methyl isobutyl ketone) under 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 6 hours, thus obtaining the polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 7:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) diphenyl silane, 4' -diamino benzanilide, cyclohexane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (116.33 g DMF+29.08g methyl isobutyl ketone) under 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 6 hours, thus obtaining the polyamide acid resin;
(3) After the reaction of step (2), adding 2.00 g of a substrate wetting agent TEGO Tain 4000 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Tain 4000 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Example 8:
the polyamide acid coating adhesive for power semiconductor package includes bis (4-aminophenoxy) diphenyl silane, 4' -diamino benzanilide, cyclohexane dianhydride and base material wetting agent.
The preparation method of the polyamide acid coating adhesive for the power semiconductor packaging comprises the following steps:
(1) 0.005mol (1.99 g) of bis (4-aminophenoxy) diphenylsilane, 0.05mol (11.35 g) of 4,4' -diaminobenzanilide were dissolved in a mixed solvent (116.33 g DMF+29.08g methyl isobutyl ketone) under 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 6 hours, thus obtaining the polyamide acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Wet 245 into the reaction product, and stirring for 1.0h to uniformly disperse the substrate wetting agent TEGO Wet 245 in the polyamic acid resin to obtain the polyamic acid coating adhesive for packaging the power semiconductor.
Comparative example 1:
the preparation of PMDA/ODA series polyamide acid resin comprises the following steps:
(1) 0.10mol (20.02 g) of ODA was dissolved in the mixed solvent (189.63 g of DMF+47.41g of methyl isobutyl ketone) under nitrogen atmosphere;
(2) The reaction temperature is 35 ℃, 0.10mol (21.81 g) PMDA is added into the system after the step (1) for reaction, and the reaction time is 6 hours, thus obtaining the polyamic acid resin;
(3) After the reaction in the step (2) is finished, adding 1.50g of a substrate wetting agent TEGO Wet 245 into the reaction product, and stirring for 1.0h to uniformly disperse the mixture in the polyamic acid resin to obtain the PMDA/ODA series polyamic acid resin.
The tensile shear strength test of the polyamide acid coating adhesive for packaging the power semiconductor is carried out by adopting the method shown in the figure 1, and the tensile property of two substrates after being partially bonded by the polyimide coating adhesive is detected; the T-peel strength test of the polyamic acid coating paste for power semiconductor package was performed by the method shown in fig. 2, and the peel strength of two substrates bonded by the polyimide coating paste was measured, and the test results are shown in the following table.
Table 1 shows the results of the viscosity test of the polyamic acid coating adhesive for power semiconductor packages prepared in examples 1 to 8, and it is clear from Table 1 that the polyamic acid coating adhesive for power semiconductor packages prepared in accordance with the present invention has good fluidity, is less likely to generate bubbles when coated on a substrate or a product, and has good leveling property.
Table 2 shows the performance data relating to the thermal imidization of the polyamide acid coating paste for power semiconductor packages prepared in examples 1-8 above to produce films having a thickness of 20-25 microns.
The polyamic acid coating adhesion test method for power semiconductor package in table 1: tested according to GB/T2794-1995 standard.
Film related performance test methods in table 2:
T g : test according to HB 7655-1999 standard;
insulation strength: tested according to GB/T1408.1-2016 standard;
tensile strength and elongation: tested according to GB/T1040.3-2006 standard;
tensile shear strength: tested 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 packaging
TABLE 2 film related Performance data
Claims (7)
1. The polyamide acid coating adhesive for packaging the power semiconductor is characterized in that the raw materials comprise aromatic diamine containing a siloxane chain segment, aromatic diamine containing an amide bond, alicyclic dianhydride and a substrate wetting agent, wherein the molar ratio of the aromatic diamine containing the siloxane chain segment to the aromatic diamine containing the amide bond is 1.00 (10.00-20.00); the molar ratio of the sum of the molar masses of the aromatic diamine containing the siloxane segment and the aromatic diamine containing the amide bond to the alicyclic dianhydride is 1.00 (0.98-1.00);
the aromatic diamine containing a siloxane segment comprises one or more of the following:
the aromatic diamine containing an amide bond comprises one or more of the following:
the alicyclic dianhydride comprises one or more of the following:
2. the method for preparing the polyamic acid coating gum for packaging a power semiconductor according to claim 1, comprising the steps of:
(1) Dissolving aromatic diamine containing siloxane chain segment and aromatic diamine containing amide bond in mixed solvent;
(2) Adding alicyclic dianhydride into the system obtained in the step (1) to react at the temperature of 30-45 ℃ for 6-8 hours to obtain polyamide acid resin;
(3) After the reaction of the step (2), 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.
3. The method for producing a polyamide acid coating paste for power semiconductor packaging according to claim 2, wherein in the step (1), the solvent mixture is in an inert gas atmosphere.
4. The method for producing a polyamide acid coating paste for power semiconductor packaging according to claim 2, wherein 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) to 1.0.
5. The method for producing polyamide acid coating glue for power semiconductor package as claimed in claim 4, wherein the polar aprotic solvent is selected from one or more of dimethylformamide, dimethylacetamide, N-methylpyrrolidone and dimethylsulfoxide, and the ketone solvent is selected from one or more of methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and isophorone.
6. The method for preparing a polyamic acid coating paste for power semiconductor packaging according to claim 4 or 5, wherein the addition amount of the mixed solvent is 80.0 to 90.0% by mass of the polyamic acid coating paste for power semiconductor packaging; the total addition amount of the diamine monomer and the dianhydride monomer accounts for 10.0-20.0% of the mass of the polyamide acid coating adhesive for packaging the power semiconductor.
7. The method of claim 5, wherein in step (3), the substrate wetting agent is one or more selected from the group consisting of TEGO Wet 245, TEGO Wet 270, TEGO Wet280, TEGO Wet500, TEGO Twain 4000, TEGO Twain 4100, and TEGO Twain 4200, and the amount of the substrate wetting agent is 0.1-2.0% of the mass of the polyamide acid coating adhesive for power semiconductor packaging.
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