CN117567746A - Aminosilane coupling agent and application thereof in moisture-heat resistant underfill - Google Patents
Aminosilane coupling agent and application thereof in moisture-heat resistant underfill Download PDFInfo
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- CN117567746A CN117567746A CN202410051036.6A CN202410051036A CN117567746A CN 117567746 A CN117567746 A CN 117567746A CN 202410051036 A CN202410051036 A CN 202410051036A CN 117567746 A CN117567746 A CN 117567746A
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- Prior art keywords
- coupling agent
- parts
- aminosilane coupling
- hydrogen
- epoxy resin
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000007822 coupling agent Substances 0.000 title claims abstract description 47
- -1 polysiloxane Polymers 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- VYFYYTLLBUKUHU-UHFFFAOYSA-N Dopamine Natural products NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 24
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 23
- 239000000047 product Substances 0.000 claims abstract description 22
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 21
- 229960003638 dopamine Drugs 0.000 claims abstract description 18
- 239000007859 condensation product Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- DMZWVCJEOLBQCZ-UHFFFAOYSA-N chloro(ethenyl)silane Chemical compound Cl[SiH2]C=C DMZWVCJEOLBQCZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 8
- 238000006482 condensation reaction Methods 0.000 claims abstract description 6
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 239000003822 epoxy resin Substances 0.000 claims description 29
- 229920000647 polyepoxide Polymers 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- 239000003086 colorant Substances 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007530 organic bases Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- WEOHANUVLKERQI-UHFFFAOYSA-N (2,4-dioxoimidazolidin-1-yl)azanium;chloride Chemical compound Cl.NN1CC(=O)NC1=O WEOHANUVLKERQI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 claims description 3
- QDASGLPLQWLMSJ-UHFFFAOYSA-N dichloro-ethenyl-phenylsilane Chemical compound C=C[Si](Cl)(Cl)C1=CC=CC=C1 QDASGLPLQWLMSJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 3
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005050 vinyl trichlorosilane Substances 0.000 claims description 3
- COMFXXABDQGVSV-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-3-carbaldehyde Chemical compound FC(F)(F)C1=NC=CC=C1C=O COMFXXABDQGVSV-UHFFFAOYSA-N 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- QLMRJHFAGVFUAC-UHFFFAOYSA-N 5-(2-aminoethyl)benzene-1,2,4-triol;hydron;chloride Chemical compound Cl.NCCC1=CC(O)=C(O)C=C1O QLMRJHFAGVFUAC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical group 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 claims description 2
- DEKNNWJXAQTLFA-UHFFFAOYSA-N dopamine 4-O-sulfate Chemical compound NCCC1=CC=C(OS(O)(=O)=O)C(O)=C1 DEKNNWJXAQTLFA-UHFFFAOYSA-N 0.000 claims description 2
- 229960001149 dopamine hydrochloride Drugs 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical group 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 abstract description 10
- 230000006872 improvement Effects 0.000 abstract description 2
- 238000004100 electronic packaging Methods 0.000 abstract 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical group CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- WGHUCJVZWJRELE-UHFFFAOYSA-N CC(C)(C1(N=CNC1(CC)CC)CC)C Chemical group CC(C)(C1(N=CNC1(CC)CC)CC)C WGHUCJVZWJRELE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention belongs to the technical field of electronic packaging, and relates to an aminosilane coupling agent and application thereof in moisture-heat resistant underfill. The aminosilane coupling agent is prepared by the following method: the hydrogen of the hydrogen-containing polysiloxane and the hydroxyl of the dopamine compound are subjected to dehydrogenation condensation reaction to obtain a dehydrogenation condensation product; carrying out alcoholysis reaction on vinyl chlorosilane and alcohol compounds to obtain alcoholysis products; and (3) performing hydrosilylation reaction on the dehydrogenation condensation product and the alcoholysis product to obtain the catalyst. The aminosilane coupling agent prepared by the invention can realize improvement of the adhesive property of the underfill, especially the moisture-heat resistant adhesive property.
Description
Technical Field
The invention belongs to the technical field of semiconductor devices, and particularly relates to an aminosilane coupling agent and application thereof in moisture-heat resistant underfill.
Background
As an important electronic adhesive, the underfill plays an indispensable key role in alleviating the stress concentration problem caused by the mismatch of thermal expansion coefficients between the chip and the substrate and improving the packaging reliability of the device. In advanced packaging, the underfill needs to be in contact with various heterogeneous interfaces such as silicon, copper, polyimide and the like, and if the interface adhesion fails, water vapor, dust, impurities and the like are easy to enter the inside of the chip, so that the reliability of the packaging is subjected to fatal influence. Practical application results show that the wet and hot environment can bring great damage to the interface adhesion of the underfill, so that the wet and hot stability of the underfill becomes an extremely critical factor affecting the reliability of the chip package.
The silane coupling agent is an organosilicon compound with a special structure, and mainly consists of two parts, wherein one part is a group which can react with an organic compound (resin, rubber), such as vinyl, amino, epoxy, mercapto and the like; the other part is a group which can undergo hydrolysis reaction and can generate firm bonding with inorganic substances (glass, silica, clay, etc.), such as alkoxy, acyloxy, halogen, etc., which are linked with silicon element through alkane. Therefore, the silane coupling agent can be used for coupling the interfaces of two materials with very different properties, namely an inorganic material and an organic material, so that satisfactory interface combination is obtained. The research shows that the silane coupling agent plays an extremely critical role in improving the interface adhesion of the underfill and the heterogeneous interface. The traditional silane coupling agent has a certain positive effect on improving the interface performance under the conventional condition of the underfill, but has limited improving effect on the moisture-heat resistant interface adhesion problem, and the main reasons are as follows: firstly, the traditional silane coupling agent has fewer reactive groups and cannot effectively participate in the curing and crosslinking reaction of the epoxy resin; secondly, the compatibility of the traditional silane coupling agent and the epoxy resin system is poor, and the phenomena of delamination, precipitation and the like are easy to occur in the long-term storage and application processes. Therefore, the development of the aminosilane coupling agent for the wet-heat resistant underfill has great significance for the technical field.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide an aminosilane coupling agent and application thereof in moisture-heat resistant underfill.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the invention provides an aminosilane coupling agent, which is prepared by the following steps: the hydrogen of the hydrogen-containing polysiloxane and the hydroxyl of the dopamine compound are subjected to dehydrogenation condensation reaction to obtain a dehydrogenation condensation product; carrying out alcoholysis reaction on vinyl chlorosilane and alcohol compounds to obtain alcoholysis products; and performing hydrosilylation reaction on the dehydrogenation condensation product and the alcoholysis product to obtain the aminosilane coupling agent.
Further, the hydrogen-containing polysiloxane is selected from one or more of terminal hydrogen-containing polysiloxane, side hydrogen-containing polysiloxane and terminal hydrogen-containing polysiloxane;
and/or the dopamine compound is selected from one or a combination of more of dopamine, dopamine hydrochloride, N-biotin dopamine, 6-hydroxy dopamine hydrobromide, 5-hydroxy dopamine hydrochloride, dopamine 4-O-sulfate and 6-hydroxy dopamine hydrochloride;
and/or the vinyl chlorosilane is selected from one or more of vinyl trichlorosilane, vinyl phenyl dichlorosilane, methyl vinyl dichlorosilane and divinyl dichlorosilane;
and/or the alcohol compound is selected from one or more of methanol, ethanol, propanol, butanol and isopropanol;
and/or the viscosity of the hydrogen-containing polysiloxane is 10-200 mpa.s, and the mass ratio of hydrogen is 0.01% -0.80%.
In another aspect, the invention provides the use of the aminosilane coupling agent in the preparation of an underfill.
In another aspect, the invention provides a method for preparing the aminosilane coupling agent, comprising the following steps:
(1) Mixing hydrogen-containing polysiloxane, dopamine compounds and a solvent 1, then dropwise adding a dehydrogenation condensation reaction catalyst, controlling the temperature to be 40-120 ℃, reacting 2-8 h to obtain a primary sample, and then extracting, distilling under reduced pressure to remove the solvent to obtain a dehydrogenation condensation product;
(2) Heating vinyl chlorosilane to 50-100 ℃, dropwise adding alcohol compounds, and reacting 6-8 h to obtain an alcoholysis product;
(3) And (3) uniformly mixing the dehydrogenation condensation product and the alcoholysis product in a solvent 2, heating to 80-150 ℃, dropwise adding a hydrosilylation reaction catalyst, reacting for 4-8 h, extracting, distilling under reduced pressure, and removing the solvent to obtain viscous liquid, namely the aminosilane coupling agent.
Further, the solvent 1 is selected from one or a combination of several of methanol, ethanol, propanol, butanol, ethyl acetate, dimethylacetamide and dimethyl sulfoxide;
and/or, the dehydrogenation condensation catalyst is an organic base catalyst;
and/or the solvent 2 is selected from one or more of benzene, xylene, toluene, butane, pentane, cyclohexane and ethyl acetate;
and/or the hydrosilylation catalyst is a group viii transition element and derivatives thereof;
and/or the mass ratio of the hydrogen-containing polysiloxane to the dopamine compound is (1-5): (3-6);
and/or, the mass ratio of the vinyl chlorosilane to the alcohol compound is (2-10): (5-20);
and/or the mass ratio of the dehydrocondensation product to the alcoholysis product is (1-2): (2-4).
Further, the organic base catalyst is selected from one or a combination of more of sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, sodium tert-butoxide and sodium isopropoxide;
the eighth group transition element and the derivative thereof are selected from one or a combination of a plurality of Pt, pd, rh, ni and complexes thereof.
The invention further provides a damp-heat resistant underfill adhesive, which comprises the following components in parts by mass: 10-40 parts of epoxy resin, 1-10 parts of diluent, 20-70 parts of inorganic filler, 0.1-5 parts of colorant, 0.1-10 parts of curing agent, 1-10 parts of amino silane coupling agent and 0.1-1 part of accelerator.
Further, the viscosity of the epoxy resin is 100-5000 mpa.s;
the diluent is an epoxy reactive diluent;
the inorganic filler is one or a combination of more of silicon dioxide, aluminum oxide, aluminum nitride and boron nitride;
the colorant is one or more of carbon black, titanium dioxide and iron oxide red;
the curing agent is an aromatic amine curing agent;
the accelerator is tertiary amine accelerator.
Further, the epoxy resin is selected from one or more of bisphenol F epoxy resin, bisphenol A epoxy resin, bisphenol S epoxy resin, bisphenol AD epoxy resin, phenolic epoxy resin and other mixed epoxy resin;
the inorganic filler is spherical silica micropowder, and the particle size of the spherical silica micropowder is 0.1-10 mu m.
The invention also provides a preparation method of the wet heat resistant underfill adhesive, which comprises the following steps:
a) Preparing an accelerator auxiliary material: uniformly mixing 0.1-1 part of accelerator with 10-20 parts of epoxy resin for standby;
b) Preparation of the main material of the epoxy resin: sequentially adding 0-20 parts of epoxy resin and 1-10 parts of diluent into a planetary power mixer, dissolving uniformly at 100-200 ℃, then adding 20-70 parts of inorganic filler, controlling the temperature of the material to be 80-100 ℃, stirring at high speed for 30-60 min, grinding by a three-roller grinder to ensure that the filler is more uniformly dispersed, defoaming under the pressure of 0.08-0.1 MPa, and cooling the material to below 20-35 ℃ for later use;
c) Preparation of underfill: sequentially adding 0.1-10 parts of curing agent, prepared accelerator auxiliary materials and 0.1-5 parts of colorant into the epoxy resin main material, stirring 1-10 parts of aminosilane coupling agent in vacuum for 50-70 min, controlling the material temperature in the whole process to be lower than 20-35 ℃, grinding, and finally filtering, discharging and subpackaging by a material pressing machine.
The aminosilane coupling agent has three key points in the aspects of molecular design and preparation: firstly, the silane coupling agent contains amino functional groups, so that the silane coupling agent has proper chemical reaction with epoxy groups in the underfill and active groups (such as hydroxyl, carboxyl and the like) of a heterogeneous interface; secondly, the silane coupling agent has proper hydrolyzable groups, so that the silane coupling agent can perform interfacial bonding action with inorganic compounds at an interface; thirdly, the solubility and the reactivity of raw materials are considered in the preparation of the silane coupling agent, so that the yield and the stability of a synthesized product are ensured.
Compared with the prior art, the invention has the advantages that:
in the molecular design of the aminosilane coupling agent, dopamine and derivatives thereof are selected as donors of amino functional groups, and the interface adhesion of the dopamine can be better improved due to the special amino structure and the polyphenol hydroxyl structure of the dopamine. When the amino-silane coupling agent is used for preparing the underfill, on one hand, the amino structure can have a chemical bonding effect with the epoxy group of the epoxy resin, so that the amino-silane coupling agent is fully combined with the organic compound component, which is the key for ensuring the stability of the amino-silane coupling agent in the underfill; on the other hand, the amino structure and the polyphenol hydroxyl structure can be chemically bonded with the hydroxyl of the silicon substrate, so that the interface chemical bonding between the amino structure and the inorganic compound is improved, and the damage of water vapor and temperature to the interface layer under the condition of damp-heat resistance is weakened through chemical bonding; simultaneously, the amino and polyphenol hydroxyl structure can improve the interface wettability of the underfill, and the interface strength of the underfill is improved from the interface thermodynamics.
Secondly, in order to weaken consumption of amino in the preparation process as much as possible and consider the problem of compatibility difference of raw materials in the molecular design of the amino silane coupling agent, the invention takes hydrogen-containing polysiloxane as a bridge, introduces amino groups into a molecular structure through condensation reaction of the hydrogen-containing polysiloxane and the dopamine phenolic hydroxyl groups, and introduces vinyl silane into the molecular structure of the silane coupling agent through hydrosilylation reaction, thereby finally obtaining the controllable preparation process capable of being industrially applied.
In short, the aminosilane coupling agent prepared by the invention is an additive type auxiliary agent or a modified auxiliary agent which is feasible in industrial application, and the improvement of the adhesive property of the underfill, particularly the moisture-heat resistant adhesive property, is successfully realized, which is incomparable with other inventions.
Drawings
FIG. 1 is a schematic diagram of the synthesis of an aminosilane coupling agent of example 1. Wherein, DA: dopamine; PHMS: a hydrogen-containing siloxane; sodium ethoxide: sodium ethoxide.
Detailed Description
For a clearer understanding of the present invention, the present invention will now be further described with reference to the following examples and drawings. The examples are for illustration only and are not intended to limit the invention in any way. In the examples, each of the starting reagent materials is commercially available, and the experimental methods without specifying the specific conditions are conventional methods and conventional conditions well known in the art, or according to the conditions recommended by the instrument manufacturer.
Example 1:
the embodiment provides an aminosilane coupling agent for a wet-heat resistant underfill, the structure and the preparation flow of the aminosilane coupling agent are shown in figure 1, and the aminosilane coupling agent is mainly prepared by reacting an amino functional group with a silane functional group, and the specific preparation method is as follows:
(1) Mixing 20 g hydrogen-containing polysiloxane (double-end hydrogen-containing polysiloxane with the mass ratio of hydrogen being 0.10 percent, the viscosity being 38 mpa.s), 40g dopamine and 200 ml ethanol/ethyl acetate mixed solvent (volume ratio of 1:1), then dropwise adding 0.1 g sodium ethoxide solution, controlling the temperature to be 100 ℃, reacting 6 h to obtain a primary sample, extracting, decompressing and distilling, and removing the solvent to obtain a dehydrogenation condensation product.
(2) 40g vinyl trichlorosilane is heated to 60 ℃, 88 g ethanol (chemically pure) is added dropwise, byproducts escape through a drying pipe, water is used for absorption, and an alcoholysis product is obtained by reaction 8 h.
(3) Mixing 30 g dehydrogenation condensation product and 80 g alcoholysis product uniformly in dimethylbenzene, heating to 120 ℃, dropwise adding a Karst platinum catalyst (Pt content is 3000 ppm), reacting 6 h, extracting, distilling under reduced pressure, and removing solvent to obtain viscous liquid, namely the aminosilane coupling agent for the damp-heat resistant underfill.
Example 2:
the embodiment provides an aminosilane coupling agent for a damp-heat resistant underfill, which is prepared by the following steps:
(1) 36 g hydrogen-containing polysiloxane (side hydrogen-containing polysiloxane, the mass ratio of hydrogen is 0.28 percent, the viscosity is 45 mpa.s), 40g of 5-hydroxy dopamine hydrochloride and 200 ml dimethyl sulfoxide/ethyl acetate mixed solvent (volume ratio is 2:1) are mixed, then 0.1 g sodium ethoxide solution is dropwise added, the temperature is controlled at 80 ℃, the reaction is carried out for 8 h, a primary sample is obtained, and then extraction and reduced pressure distillation are carried out, and the solvent is removed, so as to obtain a dehydrogenation condensation product.
(2) 40g vinylphenyl dichlorosilane is heated to 80 ℃, 100 g ethanol (chemically pure) is added dropwise, the byproducts escape through a drying tube, are absorbed by water, and react with 7 h to obtain an alcoholysis product.
(3) Uniformly mixing 42 g dehydrogenation condensation product and 96 g alcoholysis product in dimethylbenzene, heating to 110 ℃, dropwise adding a Karst platinum catalyst (Pt content is 5000 ppm), reacting 6 h, extracting, distilling under reduced pressure, and removing a solvent to obtain a viscous liquid, namely the aminosilane coupling agent for the damp-heat resistant underfill.
Example 3:
the embodiment provides an aminosilane coupling agent for a damp-heat resistant underfill, which is prepared by the following steps:
(1) 12 g hydrogen-containing polysiloxane (the mass ratio of hydrogen at the end side is 0.51 percent, the viscosity is 87 mpa.s), 40g dopamine and 200 ml methanol/ethyl acetate mixed solvent (volume ratio is 1:1) are mixed, then 0.1 g sodium methoxide solution is dropwise added, the temperature is controlled to be 100 ℃, the reaction is carried out for 6 h, a preliminary sample is obtained, and then extraction and reduced pressure distillation are carried out, and the solvent is removed, so that a dehydrogenation condensation product is obtained.
(2) 20 g divinyl dichlorosilane is heated to 100 ℃, 100 g ethanol (chemically pure) is added dropwise, byproducts escape through a drying tube, are absorbed by water, and react with 6 h to obtain an alcoholysis product.
(3) Mixing 30 g dehydrogenation condensation product and 60 g alcoholysis product uniformly in dimethylbenzene, heating to 120 ℃, dropwise adding a Karst platinum catalyst (Pt content is 5000 ppm), reacting 4 h, extracting, distilling under reduced pressure, and removing solvent to obtain viscous liquid, namely the aminosilane coupling agent for the damp-heat resistant underfill.
The aminosilane coupling agents prepared in examples 1-3 were tested for performance and the results are shown in Table 1.
TABLE 1 basic Performance test results of aminosilane coupling agent prepared in examples 1-3
As can be seen from the experimental data in Table 1, the aminosilane coupling agent prepared by the invention has lower effective viscosity and higher product yield.
Experimental example:
the aminosilane coupling agent prepared in examples 1-3 was used to prepare an underfill comprising the following components in parts by mass: 35 parts of matrix epoxy resin, 6.8 parts of reactive diluent, 63.2 parts of inorganic filler, 0.2 part of colorant, 0.5 part of accelerator, 8.2 parts of curing agent and the aminosilane coupling agent prepared in example 1, 2 or 3. Wherein the mass percentage of the aminosilane coupling agent in the underfill is 2%; the matrix epoxy is bisphenol F epoxy resin (epoxy value 0.62 eq/100 g) with viscosity of 650 mpa.s; the reactive diluent is Allyl Glycidyl Ether (AGE); the inorganic filler is spherical silica micropowder with the particle size of 2 mu m; the colorant is carbon black, and the accelerator is dimethyl tetraethyl imidazole; the curing agent is m-phenylenediamine.
A method of preparing an underfill comprising the steps of:
a) Preparing an accelerator auxiliary material: uniformly mixing the accelerator with 10 parts of epoxy resin for standby;
b) Preparation of the main material of the epoxy resin: sequentially adding 25 parts of epoxy resin and a diluent into a planetary power mixer, uniformly dissolving at 150 ℃, then adding an inorganic filler, controlling the temperature of the material to be 90 ℃, stirring at a high speed for 60 min, grinding by a three-roller grinder to ensure that the filler is more uniformly dispersed, defoaming under the pressure of 0.09 MPa, and cooling the material to be below 25 ℃ for later use;
c) Preparation of underfill: sequentially adding a curing agent, prepared accelerator auxiliary materials and a coloring agent into the main epoxy resin material, stirring the mixture in vacuum for 50 minutes, controlling the material temperature to be lower than 25 ℃ in the whole process, grinding the mixture, and finally filtering and discharging the mixture by using a material pressing machine to obtain the underfill adhesive.
The underfill with the aminosilane coupling agent (KH 550) added was used as a control, and the remaining components and preparation method were the same as described above.
The underfill adhesives prepared with the aminosilane coupling agents of examples 1-3 and the comparative underfill adhesives were subjected to performance testing and comparison, and the results are shown in Table 2.
TABLE 2 detection of the effect of aminosilane coupling agent prepared in examples 1-3 on the Performance of underfill
From the experimental data in table 2, it can be seen that the aminosilane coupling agent prepared by the invention is added into the underfill, so that various properties of the underfill can be effectively improved, and the addition of the aminosilane coupling agent has no obvious influence on the basic properties of the underfill, but can effectively improve the adhesion between the underfill and the silicon/PI substrate, and especially improve the adhesion property, mechanical property and insulation property after moisture and heat resistance.
The above description of the embodiments is only for aiding in the understanding of the method of the present invention and its core ideas. It should be noted that it will be apparent to those skilled in the art that various changes and modifications can be made herein without departing from the principles of the invention, which are also intended to fall within the scope of the invention as defined in the appended claims.
Claims (10)
1. An aminosilane coupling agent is characterized in that the aminosilane coupling agent is prepared by the following method: the hydrogen of the hydrogen-containing polysiloxane and the hydroxyl of the dopamine compound are subjected to dehydrogenation condensation reaction to obtain a dehydrogenation condensation product; carrying out alcoholysis reaction on vinyl chlorosilane and alcohol compounds to obtain alcoholysis products; and performing hydrosilylation reaction on the dehydrogenation condensation product and the alcoholysis product to obtain the aminosilane coupling agent.
2. The aminosilane coupling agent according to claim 1, wherein the hydrogen-containing polysiloxane is selected from the group consisting of terminal hydrogen-containing polysiloxanes, pendant hydrogen-containing polysiloxanes, and combinations of one or more of terminal hydrogen-containing polysiloxanes;
and/or the dopamine compound is selected from one or a combination of more of dopamine, dopamine hydrochloride, N-biotin dopamine, 6-hydroxy dopamine hydrobromide, 5-hydroxy dopamine hydrochloride, dopamine 4-O-sulfate and 6-hydroxy dopamine hydrochloride;
and/or the vinyl chlorosilane is selected from one or more of vinyl trichlorosilane, vinyl phenyl dichlorosilane, methyl vinyl dichlorosilane and divinyl dichlorosilane;
and/or the alcohol compound is selected from one or more of methanol, ethanol, propanol, butanol and isopropanol;
and/or the viscosity of the hydrogen-containing polysiloxane is 10-200 mpa.s, and the mass ratio of hydrogen is 0.01% -0.80%.
3. The use of an aminosilane coupling agent as defined in claim 1, wherein said use is the use of an aminosilane coupling agent as defined in claim 1 in the preparation of an underfill.
4. A method for preparing the aminosilane coupling agent as defined in claim 1, comprising the steps of:
(1) Mixing hydrogen-containing polysiloxane, dopamine compounds and a solvent 1, then dropwise adding a dehydrogenation condensation reaction catalyst, controlling the temperature to be 40-120 ℃, reacting 2-8 h to obtain a primary sample, and then extracting, distilling under reduced pressure to remove the solvent to obtain a dehydrogenation condensation product;
(2) Heating vinyl chlorosilane to 50-100 ℃, dropwise adding alcohol compounds, and reacting 6-8 h to obtain an alcoholysis product;
(3) And (3) uniformly mixing the dehydrogenation condensation product and the alcoholysis product in a solvent 2, heating to 80-150 ℃, dropwise adding a hydrosilylation reaction catalyst, reacting for 4-8 h, extracting, distilling under reduced pressure, and removing the solvent to obtain viscous liquid, namely the aminosilane coupling agent.
5. The preparation method according to claim 4, wherein the solvent 1 is selected from one or more of methanol, ethanol, propanol, butanol, ethyl acetate, dimethylacetamide and dimethylsulfoxide;
and/or, the dehydrogenation condensation catalyst is an organic base catalyst;
and/or the solvent 2 is selected from one or more of benzene, xylene, toluene, butane, pentane, cyclohexane and ethyl acetate;
and/or the hydrosilylation catalyst is a group viii transition element and derivatives thereof;
and/or the mass ratio of the hydrogen-containing polysiloxane to the dopamine compound is (1-5): (3-6);
and/or, the mass ratio of the vinyl chlorosilane to the alcohol compound is (2-10): (5-20);
and/or the mass ratio of the dehydrocondensation product to the alcoholysis product is (1-2): (2-4).
6. The preparation method according to claim 5, wherein the organic base catalyst is selected from one or more of sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, sodium tert-butoxide, and sodium isopropoxide;
the eighth group transition element and the derivative thereof are selected from one or a combination of a plurality of Pt, pd, rh, ni and complexes thereof.
7. The moisture-heat resistant underfill is characterized by comprising the following components in parts by mass: 10-40 parts of epoxy resin, 1-10 parts of diluent, 20-70 parts of inorganic filler, 0.1-5 parts of colorant, 0.1-10 parts of curing agent, 1-10 parts of aminosilane coupling agent as defined in claim 1 and 0.1-1 part of accelerator.
8. The wet heat resistant underfill of claim 7 wherein the epoxy has a viscosity of 100-5000 mpa.s;
the diluent is an epoxy reactive diluent;
the inorganic filler is one or a combination of more of silicon dioxide, aluminum oxide, aluminum nitride and boron nitride;
the colorant is one or more of carbon black, titanium dioxide and iron oxide red;
the curing agent is an aromatic amine curing agent;
the accelerator is tertiary amine accelerator.
9. The wet heat resistant underfill of claim 8 wherein the epoxy resin is selected from one or more of bisphenol F epoxy resin, bisphenol a epoxy resin, bisphenol S epoxy resin, bisphenol AD epoxy resin, phenolic epoxy resin and other hybrid epoxy resins;
the inorganic filler is spherical silica micropowder, and the particle size of the spherical silica micropowder is 0.1-10 mu m.
10. A method of preparing the wet heat resistant underfill of claim 7, comprising the steps of:
a) Preparing an accelerator auxiliary material: uniformly mixing 0.1-1 part of accelerator with 10-20 parts of epoxy resin for standby;
b) Preparation of the main material of the epoxy resin: sequentially adding 0-20 parts of epoxy resin and 1-10 parts of diluent into a planetary power mixer, dissolving uniformly at 100-200 ℃, then adding 20-70 parts of inorganic filler, controlling the temperature of the material to be 80-100 ℃, stirring at high speed for 30-60 min, grinding by a three-roller grinder to ensure that the filler is more uniformly dispersed, defoaming under the pressure of 0.08-0.1 MPa, and cooling the material to below 20-35 ℃ for later use;
c) Preparation of underfill: sequentially adding 0.1-10 parts of curing agent, prepared accelerator auxiliary materials and 0.1-5 parts of colorant into the epoxy resin main material, stirring 1-10 parts of aminosilane coupling agent in vacuum for 50-70 min, controlling the material temperature in the whole process to be lower than 20-35 ℃, grinding, and finally filtering, discharging and subpackaging by a material pressing machine.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103170258A (en) * | 2012-12-04 | 2013-06-26 | 天津大学 | Polydimethylsiloxane/polydopamine hybrid membrane and preparation method thereof |
| CN103724368A (en) * | 2014-01-09 | 2014-04-16 | 嘉兴学院 | Preparation method of amino polyether-type silanization reagent |
| KR20150118248A (en) * | 2014-04-11 | 2015-10-22 | 가톨릭대학교 산학협력단 | Fabrication of Polydopamine Coated Monodisperse Polydimethylsiloxane Microsphere |
| JP2016117696A (en) * | 2014-12-23 | 2016-06-30 | 東レ・ダウコーニング株式会社 | Silane coupling agent composition, method of producing the same, epoxy resin composition, material for encapsulating semiconductor, and semiconductor device |
| CN106189514A (en) * | 2016-08-04 | 2016-12-07 | 佛山科学技术学院 | Black blue and white coloring material aqueous dispersant and preparation method and application for inkjet printing |
| CN113174048A (en) * | 2021-04-25 | 2021-07-27 | 深圳先进电子材料国际创新研究院 | Macromolecular silane coupling agent and preparation method thereof |
| CN117005200A (en) * | 2023-09-04 | 2023-11-07 | 江苏轩达高分子材料有限公司 | Bio-based fiber for fabric and preparation method thereof |
| US20230407133A1 (en) * | 2020-12-06 | 2023-12-21 | Momentive Performance Materials Inc. | Curable silicone coating comprising a non-organo tin catalyst |
-
2024
- 2024-01-15 CN CN202410051036.6A patent/CN117567746B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103170258A (en) * | 2012-12-04 | 2013-06-26 | 天津大学 | Polydimethylsiloxane/polydopamine hybrid membrane and preparation method thereof |
| CN103724368A (en) * | 2014-01-09 | 2014-04-16 | 嘉兴学院 | Preparation method of amino polyether-type silanization reagent |
| KR20150118248A (en) * | 2014-04-11 | 2015-10-22 | 가톨릭대학교 산학협력단 | Fabrication of Polydopamine Coated Monodisperse Polydimethylsiloxane Microsphere |
| JP2016117696A (en) * | 2014-12-23 | 2016-06-30 | 東レ・ダウコーニング株式会社 | Silane coupling agent composition, method of producing the same, epoxy resin composition, material for encapsulating semiconductor, and semiconductor device |
| CN106189514A (en) * | 2016-08-04 | 2016-12-07 | 佛山科学技术学院 | Black blue and white coloring material aqueous dispersant and preparation method and application for inkjet printing |
| US20230407133A1 (en) * | 2020-12-06 | 2023-12-21 | Momentive Performance Materials Inc. | Curable silicone coating comprising a non-organo tin catalyst |
| CN113174048A (en) * | 2021-04-25 | 2021-07-27 | 深圳先进电子材料国际创新研究院 | Macromolecular silane coupling agent and preparation method thereof |
| CN117005200A (en) * | 2023-09-04 | 2023-11-07 | 江苏轩达高分子材料有限公司 | Bio-based fiber for fabric and preparation method thereof |
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