WO2022188504A1 - Adhésif conducteur thermodurci et procédé de préparation associé - Google Patents
Adhésif conducteur thermodurci et procédé de préparation associé Download PDFInfo
- Publication number
- WO2022188504A1 WO2022188504A1 PCT/CN2021/139775 CN2021139775W WO2022188504A1 WO 2022188504 A1 WO2022188504 A1 WO 2022188504A1 CN 2021139775 W CN2021139775 W CN 2021139775W WO 2022188504 A1 WO2022188504 A1 WO 2022188504A1
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- WO
- WIPO (PCT)
- Prior art keywords
- conductive adhesive
- parts
- epoxy resin
- thermally cured
- cured conductive
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 101
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 101
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003822 epoxy resin Substances 0.000 claims abstract description 55
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 55
- 239000002994 raw material Substances 0.000 claims abstract description 51
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000003860 storage Methods 0.000 claims abstract description 17
- 238000001723 curing Methods 0.000 claims abstract description 15
- 239000003085 diluting agent Substances 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 238000013007 heat curing Methods 0.000 claims abstract description 6
- 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 42
- 238000001029 thermal curing Methods 0.000 claims description 35
- -1 1-cyano-2-ethyl Chemical group 0.000 claims description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
- 239000004814 polyurethane Substances 0.000 claims description 19
- 229920002635 polyurethane Polymers 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 12
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000227 grinding Methods 0.000 claims description 9
- YPACMOORZSDQDQ-UHFFFAOYSA-N 3-(4-aminobenzoyl)oxypropyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCCCOC(=O)C1=CC=C(N)C=C1 YPACMOORZSDQDQ-UHFFFAOYSA-N 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 6
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 6
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 6
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- 238000004017 vitrification Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 abstract description 8
- 239000012752 auxiliary agent Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 description 38
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000002313 adhesive film Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- YMJPBYVLNFBSFE-UHFFFAOYSA-N 2-ethyl-4-methylimidazole-1-carbonitrile Chemical compound CCC1=NC(C)=CN1C#N YMJPBYVLNFBSFE-UHFFFAOYSA-N 0.000 description 5
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 5
- 239000000654 additive Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000011231 conductive filler Substances 0.000 description 2
- 238000004100 electronic packaging Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- ALMJNNAHXBQOEW-UHFFFAOYSA-N 2-(4-aminobenzoyl)oxypropyl 4-aminobenzoate Chemical compound C=1C=C(N)C=CC=1C(=O)OC(C)COC(=O)C1=CC=C(N)C=C1 ALMJNNAHXBQOEW-UHFFFAOYSA-N 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
Definitions
- the present application relates to the field of conductive adhesives, and in particular, to a thermally cured conductive adhesive and a preparation method thereof.
- Conductive adhesive is a lead-free, green electronic packaging material suitable for micro-nano electronic packaging and interconnection of semiconductor components.
- the conductive adhesive is mainly composed of conductive fillers, matrix resins, diluents and additives. It is thermally cured to form a conductive colloid with a three-dimensional network structure. It has the advantages of high bonding strength, high thermal stability, and low volume resistivity. However, its impact resistance The performance and crack resistance are low, and it is often difficult to meet the high reliability requirements of electronic products.
- the purpose of the embodiments of the present application is to provide a thermally cured conductive adhesive and a preparation method thereof, which are intended to improve the impact resistance of the conductive adhesive.
- the present application provides a method for preparing a thermally cured conductive adhesive, which mainly includes the following steps: thermally curing raw materials at 150-200° C. for 30-60 minutes; wherein, the raw materials include the following components in parts by weight: epoxy resin 5-14.5 parts of resin, 3-10 parts of diluent, 0.5-1 part of curing agent, 1.5-4.5 parts of flexibility auxiliary and 70-90 parts of micron silver powder.
- the thermally cured conductive adhesive obtained by the above preparation method has better rheological properties and mechanical properties, and also has the advantages of low volume resistance, high bonding strength, high impact strength, low glass transition temperature and low storage modulus.
- the epoxy resin is selected from bisphenol A epoxy resin, bisphenol F epoxy resin, alicyclic epoxy resin, acrylic modified epoxy resin, polyurethane modified epoxy resin, silicone At least one of modified epoxy resin, organic titanium modified epoxy resin and organic boron modified epoxy resin.
- the diluent is selected from the group consisting of hydroxyethyl methacrylate, hydroxypropyl methacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, styrene, At least one of bisphenol A acrylate, ethoxylated bisphenol A diacrylate, and bisphenol A dimethacrylate.
- the curing agent is selected from 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyano-2-ethyl-4-methylimidazole, blocked type At least one of hexafluoroantimonate, triaryliodonium salt, alkyl iodonium salt, and cumene ferrocene hexafluorophosphate.
- the flexibilizer is selected from poly[(4-vinylphenol)-co-(methyl methacrylate)], poly(dimethylsiloxane-diphenylsiloxane) ), at least one of polydimethylsiloxane diglycidyl ether, 1,3-propanediol bis(4-aminobenzoate), and vinyl ether.
- the particle size of the micron silver powder D50 is 3-5 ⁇ m
- the bulk density is 3-5 g ⁇ cm ⁇ 3
- the specific surface area is 0.5-1 m 2 ⁇ g ⁇ 1 .
- the raw material before the raw material is thermally cured at 150-200° C. for 30-60 min, it further includes:
- the raw material is prepared by mixing the epoxy resin, the diluent, the curing agent, the flexibility assistant and the micron silver powder, and then grinding and defoaming.
- the thermal curing temperature of the raw material is 150-175°C.
- the present application also provides a heat-curable conductive adhesive, which is prepared by the above-mentioned preparation method of the heat-curable conductive adhesive.
- the present application also provides a heat-curing conductive adhesive, the volume resistance of the heat-curing conductive adhesive is 9-31 ⁇ cm, the bonding strength is 6.8-9.1 MPa, the impact strength is 2.7-4.0 kJ ⁇ m -2 , and the glass transition temperature is 6.8-9.1 MPa.
- the storage modulus at room temperature is 6.1-7.6GPa, the storage modulus at 175°C is 0.7-2.4GPa, and the storage modulus at 240°C is 0.5-1.1GPa.
- thermally curable conductive adhesive and the preparation method thereof of the embodiments of the present application will be specifically described below.
- a preparation method of a thermally cured conductive adhesive mainly comprises the following steps:
- the raw material includes the following components in parts by weight:
- the raw materials containing the above-mentioned substances are thermally cured at 150-200 ° C for 30-60 minutes to obtain a thermally cured conductive adhesive.
- the conductive adhesive has low volume resistance, high bonding strength, high impact strength, low glass transition temperature and storage. Low energy modulus and other properties.
- the temperature of thermal curing may be 150°C, 152°C, 155°C, 161°C, 165°C, 172°C, 180°C, 191°C, 195°C, or 200°C, and the like.
- the heating method can be, for example, heating with an oven or heating with an infrared furnace, and so on.
- the time of thermal curing can be, for example, 30 min, 32 min, 38 min, 41 min, 47 min, 50 min, 52 min, 59 min or 60 min, and the like.
- the raw materials include epoxy resin, diluent, curing agent, flexibilizer and micron silver powder.
- the epoxy resin accounts for 5-14.5 parts by weight of the raw material, for example, it can be 5 parts, 6 parts, 7 parts, 7.5 parts, 8 parts, 9 parts, 9.5 parts, 10 parts, 11 parts, 12 parts servings, 12.5 servings, 12.7 servings, 13 servings, or 14.5 servings, etc.
- the epoxy resin is selected from the group consisting of bisphenol A epoxy resin, bisphenol F epoxy resin, cycloaliphatic epoxy resin, acrylic modified epoxy resin, polyurethane modified epoxy resin, silicone modified epoxy resin At least one of oxygen resin, organic titanium modified epoxy resin and organic boron modified epoxy resin.
- the epoxy resin is selected from bisphenol A epoxy resin, bisphenol F epoxy resin, alicyclic epoxy resin, acrylic modified epoxy resin or polyurethane Modified epoxy resin. For example, 6 parts by weight of acrylic modified epoxy resin is selected.
- the diluent accounts for 3-10 parts by weight of the raw material, for example, it can be 3 parts, 3.1 parts, 3.5 parts, 3.7 parts, 4 parts, 4.9 parts, 5.5 parts, 5.6 parts, 6 parts, 6.25 parts , 6.8, 7.5, 8, 8.2, 9.1, 9.9, or 10, etc.
- the diluent is selected from the group consisting of hydroxyethyl methacrylate, hydroxypropyl methacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, styrene, bisphenol A At least one of acrylate, ethoxylated bisphenol A diacrylate, and bisphenol A dimethacrylate.
- the diluent is selected from hydroxyethyl methacrylate, hydroxypropyl methacrylate, 1,6-hexanediol diacrylate, trimethylol Propane triacrylate, bisphenol A acrylate or bisphenol A dimethacrylate. For example, 5.5 parts by weight of bisphenol A acrylate is selected.
- the curing agent accounts for 0.5-1 part by weight of the raw material, such as 0.5 part, 0.6 part, 0.7 part, 0.75 part, 0.8 part, 0.9 part or 1.0 part and so on.
- the curing agent is selected from the group consisting of 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyano-2-ethyl-4-methylimidazole, blocked hexafluoroantimonate , one or more of triaryliodonium salts, alkyl iodonium salts, and cumene ferrocene hexafluorophosphate.
- the curing agent is selected from the group consisting of 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyano-2-ethyl-4-methylimidazole, blocked hexafluoroantimonate , one or more of triaryliodonium salts, alkyl iodonium salts, and cumene ferrocene hexafluorophosphate.
- triaryliodonium salt 0.65 parts by weight of triaryliodonium salt is selected.
- the above curing agent is selected from 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyano-2-ethyl-4- Methylimidazole, blocked hexafluoroantimonate, triaryliodonium or cumene ferrocene hexafluorophosphate.
- the weight part of the softening aid is 1.5-4.5 parts of the raw material, for example, it can be 1.5 parts, 1.8 parts, 2 parts, 2.3 parts, 2.6 parts, 3 parts, 3.2 parts, 3.5 parts, 4 parts or 4.5 parts and so on.
- the above-mentioned flexibilizer is a flexibilizer containing a flexible ether bond.
- the -C-C- chemical bond length in the flexible additive is long, the -C-C- chemical bond angle is large, the short-range repulsion inside the molecular chain is small, and the rotation or twist of the main chain of the molecular chain can give the conductive adhesive excellent flexibility; softness in the flexible additive
- the ether bond segment can be grafted into the network structure of the matrix resin cross-linked in the conductive adhesive to form an orderly and spaced network structure to improve the flexibility of the conductive adhesive; when the thermally cured conductive adhesive is used to bond electronic components, it can be Reduce the thermal stress in the bonding of the conductive adhesive and electronic components, and reduce the cracking and delamination of the conductive adhesive and electronic components caused by thermal stress.
- the flexibility assistant is selected from poly[(4-vinylphenol)-co-(methyl methacrylate)], poly(dimethylsilicon) One or more of oxane-diphenylsiloxane), polydimethylsiloxane diglycidyl ether, 1,3-propanediol bis(4-aminobenzoate) and vinyl ether.
- polydimethylsiloxane diglycidyl ether 2.5 parts by weight of polydimethylsiloxane diglycidyl ether is selected.
- the micron silver powder accounts for 70-90 parts by weight of the raw material.
- it can be 70, 72, 75, 80, 82, 85, 86, 89, or 90, and the like.
- the particle size of the micron silver powder D50 is 3-5 ⁇ m
- the bulk density is 3-5 g.cm ⁇ 3
- the specific surface area is 0.5-1 m 2 .g ⁇ 1 .
- the particle size of the micron silver powder D50 may be 3 ⁇ m, 4 ⁇ m, or 5 ⁇ m, and so on.
- the bulk density of the micron silver powder is 3-5 g.cm -3 , for example, it can be 3 g.cm -3 , 4 g.cm -3 or 5 g.cm -3 and so on.
- the specific surface area can be, for example, 0.5m 2 .g -1 , 0.7m 2 .g -1 , 0.8m 2 .g -1 , 0.9m 2 .g -1 , 1m 2 .g -1 , and the like.
- the raw materials are obtained by mixing, grinding and then defoaming of the above-mentioned raw materials in various proportions. After the raw material is obtained, the raw material is thermally cured to obtain a flexible conductive adhesive. While improving the flexibility of the thermally cured conductive adhesive, the rheological properties and mechanical properties of the conductive adhesive are guaranteed, and the micron silver powder is used as a conductive filler to ensure the electrical properties of the conductive adhesive.
- the present application also provides a thermally curable conductive adhesive, which has low volume resistance, high bonding strength, high impact strength, low glass transition temperature and low storage modulus.
- the present application also provides a heat-curable conductive adhesive, the volume resistance of the heat-cured conductive adhesive is 9-31 ⁇ cm, the bonding strength is 6.8-9.1 MPa, the impact strength is 2.7-4.0 kJ ⁇ m -2 , the vitrification
- the transition temperature is 151-161°C
- the storage modulus at room temperature is 6.1-7.6GPa
- the storage modulus at 175°C is 0.7-2.4GPa
- the storage modulus at 240°C is 0.5-1.1GPa.
- room temperature refers to the indoor temperature during measurement, which is usually 20-30°C.
- Example 11 The micron silver powder used in Example 1-Example 11 was purchased from Japan Fukuda Metal Foil Powder Industry Co., Ltd., AgC-201 silver powder: solid density 3.43g ⁇ cm -3 , specific surface area 0.72m 2 ⁇ g -1 , average particle size 4.3 ⁇ m.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 150° C., and the curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 150° C., and the thermal curing time is 60 min.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- Cicyclic epoxy resin (CVC resin Epalloy 5200) 10 parts, 1,6-hexanediol diacrylate (MacLean reagent) 6.25 parts, 1-cyano-2-ethyl-4-methylimidazole (MacLean reagent) Reagent) 0.75 parts, 3 parts of polydimethylsiloxane diglycidyl ether (MacLean reagent), 80 parts of micron silver powder (Foton Metal AgC-201).
- CVC resin Epalloy 5200 10 parts, 1,6-hexanediol diacrylate (MacLean reagent) 6.25 parts, 1-cyano-2-ethyl-4-methylimidazole (MacLean reagent) Reagent) 0.75 parts, 3 parts of polydimethylsiloxane diglycidyl ether (MacLean reagent), 80 parts of micron silver powder (Foton Metal AgC-201).
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 200° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 200° C., and the thermal curing time is 60 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- Cicyclic epoxy resin (CVC resin Epalloy 5200) 9.5 parts, bisphenol A dimethacrylate (MacLean reagent) 6 parts, cumyl ferrocene hexafluorophosphate (MacLean reagent) 0.5 parts, 1,3 - 4 parts of propylene glycol bis(4-aminobenzoate) (MacLean reagent), 80 parts of micron silver powder (Foton Metal AgC-201).
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 60 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- polyurethane modified epoxy resin bisphenol A acrylate, triaryliodonium salt, poly(dimethylsiloxane-diphenylsiloxane), and micron silver powder are fully stirred and dispersed, and then ground and defoamed. , that is, the conductive adhesive raw material is obtained.
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- polyurethane modified epoxy resin bisphenol A acrylate, triaryl iodonium salt, polydimethylsiloxane diglycidyl ether, and micron silver powder are fully stirred and dispersed, and then ground and deaerated to obtain conductive adhesive. raw material.
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- the embodiment provides a thermally cured conductive adhesive, which is mainly prepared by the following steps:
- the above conductive adhesive raw materials are thermally cured by means of oven heating, the thermal curing temperature is 175° C., and the thermal curing time is 30 minutes.
- Volume resistance Print the thermally cured conductive adhesives of Examples 1 to 11 and commercially available products on a glass sheet to obtain a conductive adhesive film with a size of 30mm ⁇ 10mm ⁇ 0.05mm. After thermal curing, use the four-point probe method to test the resistance , and calculate the volume resistance.
- Adhesion strength The thermally cured conductive adhesive of Example 1-Example 11 and commercially available products were printed on the glass sheet to obtain a conductive adhesive film with a size of 5mm ⁇ 5mm ⁇ 0.05mm, and then placed on the glass sheet (5mm ⁇ 5mm ⁇ 1mm) On the conductive adhesive film, two layers of glass sheets and one layer of conductive adhesive film form a "sandwich" structure; after thermal curing, it is tested by a multifunctional mechanical testing machine.
- the thermally cured conductive adhesives of Examples 1 to 11 and commercially available products were printed on glass sheets to obtain a conductive adhesive film with a size of 50 mm ⁇ 3 mm ⁇ 0.7 mm. After thermal curing, a dynamic mechanical thermal analyzer was used. The storage modulus of the conductive adhesive was tested at room temperature (RT), 175°C, and 240°C. During the test, the room temperature (RT) was 26°C.
- Glass transition temperature The thermally cured conductive adhesives of Examples 1 to 11 and commercially available products were printed on the glass sheet to obtain a conductive adhesive film with a size of 50 mm ⁇ 3 mm ⁇ 0.7 mm. After thermal curing, a dynamic mechanical thermal analyzer was used. test.
- the thermally cured conductive adhesive provided by the application has low volume resistance, about 9-31 ⁇ cm, high bonding strength, about 6.8-9.1 MPa, and high impact strength, about 2.7- 4.0kJ ⁇ m -2 , low glass transition temperature, about 151-161°C, low storage modulus, about 6.1-7.6GPa at RT, about 0.7-2.4GPa at 175°C, about 240°C 0.5-1.1GPa, which are better than commercially available products. It is illustrated that the thermally cured conductive adhesive obtained by the preparation method of the thermally cured conductive adhesive provided in the embodiment of the present application has the advantages of low volume resistance, high bonding strength, high impact strength, low glass transition temperature, and low storage modulus.
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- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Abstract
La présente invention concerne le domaine des adhésifs conducteurs et plus précisément, concerne un adhésif conducteur thermodurci et un procédé de préparation associé. Le procédé de préparation de l'adhésif conducteur thermodurci comprend principalement l'étape suivante : thermodurcissement de matières de départ à 150-200 ºC pendant 30-60 min, les matières premières comprenant les constituants suivants, en parties en poids : 5 à 14,5 parties d'une résine époxy, 3 à 10 parties d'un diluant, 0,5 à 1 partie d'un agent durcisseur, 1,5 à 4,5 parties d'un agent auxiliaire souple et 70 à 90 parties d'une poudre d'argent micrométrique. L'adhésif conducteur thermodurci préparé au moyen du procédé de préparation a de bonnes propriétés rhéologiques et mécaniques et présente également les avantages d'une faible résistance volumique, d'une grande force d'adhérence, d'une grande résistance au choc, d'une faible température de transition vitreuse, d'un faible module de conservation, etc.
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CN115141588A (zh) * | 2022-06-29 | 2022-10-04 | 上海回天新材料有限公司 | 一种用于Type C密封的环氧树脂胶粘剂及其制备方法 |
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