CN113025037A - Thermosetting resin composition and preparation method and application thereof - Google Patents
Thermosetting resin composition and preparation method and application thereof Download PDFInfo
- Publication number
- CN113025037A CN113025037A CN202110173482.0A CN202110173482A CN113025037A CN 113025037 A CN113025037 A CN 113025037A CN 202110173482 A CN202110173482 A CN 202110173482A CN 113025037 A CN113025037 A CN 113025037A
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- China
- Prior art keywords
- parts
- resin
- epoxy resin
- halogen
- copper
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 24
- 239000011342 resin composition Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 80
- 239000011347 resin Substances 0.000 claims abstract description 80
- 239000003822 epoxy resin Substances 0.000 claims abstract description 40
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 40
- 239000004793 Polystyrene Substances 0.000 claims abstract description 33
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229920002223 polystyrene Polymers 0.000 claims abstract description 26
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 23
- 239000004643 cyanate ester Substances 0.000 claims abstract description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011574 phosphorus Substances 0.000 claims abstract description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 18
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 14
- 239000005011 phenolic resin Substances 0.000 claims abstract description 14
- 239000003292 glue Substances 0.000 claims description 46
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 20
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 18
- 239000003063 flame retardant Substances 0.000 claims description 18
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 17
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 239000011889 copper foil Substances 0.000 claims description 7
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 5
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 5
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 claims description 2
- LOOCNDFTHKSTFY-UHFFFAOYSA-N 1,1,2-trichloropropyl dihydrogen phosphate Chemical compound CC(Cl)C(Cl)(Cl)OP(O)(O)=O LOOCNDFTHKSTFY-UHFFFAOYSA-N 0.000 claims description 2
- PAPPEKHULAQSEJ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)propanenitrile Chemical compound N#CC(C)C1=NC=CN1 PAPPEKHULAQSEJ-UHFFFAOYSA-N 0.000 claims description 2
- QKVROWZQJVDFSO-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethanamine Chemical compound CC1=NC=CN1CCN QKVROWZQJVDFSO-UHFFFAOYSA-N 0.000 claims description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 2
- IMKCTLWSQVQFHW-UHFFFAOYSA-N C(C)C=1NC=CN1.C(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)C=1NC=CN1.C(C1=CC=CC=C1)C1=CC=CC=C1 IMKCTLWSQVQFHW-UHFFFAOYSA-N 0.000 claims description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- SMYKVLBUSSNXMV-UHFFFAOYSA-K aluminum;trihydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[Al+3] SMYKVLBUSSNXMV-UHFFFAOYSA-K 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 239000005350 fused silica glass Substances 0.000 claims description 2
- 239000011874 heated mixture Substances 0.000 claims description 2
- 239000011256 inorganic filler Substances 0.000 claims description 2
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 2
- 238000010030 laminating Methods 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004843 novolac epoxy resin Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- MNXMYPGMDRJENK-UHFFFAOYSA-N P1(=O)(OC2=CC(=CC=C2)O1)OC1=C(C=CC=C1C)C Chemical compound P1(=O)(OC2=CC(=CC=C2)O1)OC1=C(C=CC=C1C)C MNXMYPGMDRJENK-UHFFFAOYSA-N 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 description 21
- 238000001514 detection method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000003825 pressing Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 4
- 239000000805 composite resin Substances 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 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 description 2
- 230000007547 defect Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 238000013517 stratification Methods 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- -1 2, 6-xylenyl-1, 3-phenylene phosphate Chemical compound 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012536 packaging technology Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/082—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising vinyl resins; comprising acrylic resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
- B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/302—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L79/085—Unsaturated polyimide precursors
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a thermosetting resin composition, a preparation method and application thereof. The thermosetting resin composition comprises the following components in parts by weight: 5-15 parts of epoxy resin, 10-30 parts of polystyrene allyl glycidyl ether resin, 10-35 parts of cyanate ester resin, 15-25 parts of bismaleimide resin and 5-10 parts of phosphorus-containing phenolic resin. The thermosetting resin composition has the advantages of low expansion coefficient, Tg up to 250 ℃, good heat resistance and dielectric property, low dielectric loss and the like, and can be well applied to a printed circuit board of a packaging carrier plate.
Description
Technical Field
The invention relates to the technical field of copper-clad plates, in particular to a thermosetting resin composition and a preparation method and application thereof.
Background
With the development of electronic products gradually towards the directions of lightness, thinness, high speed, high frequency and the like, the products provide more severe requirements for the innovation of the upstream copper-clad plate industry in the aspects of heat dissipation, precise layout, packaging design and the like. IC packaging technology requires that the substrate of the package have high heat resistance, moisture resistance, and rigidity (Low CTE), while having very little loss for signal transmission (i.e., Low dielectric loss); however, the thermosetting material used in the conventional FR-4 material has the disadvantages of high expansion coefficient, large dielectric loss, and the like, and thus cannot satisfy the above requirements.
The bismaleimide resin has the excellent characteristics of low thermal expansion coefficient, small dielectric loss, high glass transition temperature and the like, and can meet the requirements, but has the problems of poor solubility, harsh process conditions, high crosslinking density, high brittleness and the like, and the service performance of the bismaleimide resin is seriously influenced. In addition, the composite resin system of bismaleimide and cyanate has the problems that good polymerization cannot be performed between cyanate and bismaleimide, and the like, so that the heat resistance of the cured resin is not high, and the overall performance of the resin is not good. Therefore, how to develop a thermosetting resin with low dielectric loss and high heat resistance by using a bismaleimide resin is a problem to be solved.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a thermosetting resin composition, a preparation method and application thereof, and the thermosetting resin composition has the advantages of low expansion coefficient, high Tg (glass transition temperature) up to 250 ℃, low heat resistance and dielectric constant, low dielectric loss and the like.
The invention provides a thermosetting resin composition which comprises the following components in parts by weight: 5-15 parts of epoxy resin, 10-30 parts of polystyrene allyl glycidyl ether resin, 10-35 parts of cyanate ester resin, 15-25 parts of bismaleimide resin and 5-10 parts of phosphorus-containing phenolic resin.
In the present invention, the epoxy resin is at least one selected from the group consisting of bisphenol a type epoxy resin, bisphenol F type novolac epoxy resin, novolac type epoxy resin, o-cresol novolac type epoxy resin, DCPD type epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, and biphenyl type epoxy resin.
Preferably, the epoxy resin comprises o-cresol formaldehyde type epoxy resin and trifunctional epoxy resin, and the mass ratio of the o-cresol formaldehyde type epoxy resin to the trifunctional epoxy resin is (6-10): (4-5), more preferably 8: 5.
in the present invention, the preparation method of the polystyrene allyl glycidyl ether resin may include:
uniformly mixing 75-85 parts of cyclohexanone, 200-215 parts of styrene and 110-120 parts of allyl glycidyl ether, heating to 80-90 ℃, adding 0.02-0.04 part of tert-butyl peroxybenzoate and 0.004-0.006 part of hydroquinone into the heated mixture, uniformly mixing, continuously heating to 90-100 ℃, and carrying out heat preservation reaction for 2.5-3.5 hours to obtain the polystyrene allyl glycidyl ether resin.
The polystyrene allyl glycidyl ether resin prepared by the method has nonpolar styrene units, and provides excellent low dielectric property and heat resistance; the thermosetting resin composition containing the polystyrene allyl glycidyl ether resin has the advantages of low expansion coefficient, Tg as high as 250 ℃, low heat resistance, low dielectric constant, low dielectric loss and the like.
In the present invention, the cyanate ester resin is selected from at least one of bisphenol A type cyanate ester resin and phenol type cyanate ester resin, for example, of Lonza, Switzerland
BA-230S、
PT-30S, Yangzhou Tianqi C01PS and the like. Preferably, the cyanate ester resin is a bisphenol a type cyanate ester resin.
In the present invention, the bismaleimide resin and the phosphorus-containing phenolic resin can adopt the conventional resin in the field, for example, the bismaleimide resin can adopt BMI-5100, BMI-4000 and the like in Japan and chemical industry, and the phosphorus-containing phenolic resin can adopt LC-950PM60, XZ92741, TPH890M60 and the like.
The invention also provides glue solution for the halogen-free low-loss copper-clad plate, which comprises the following components in parts by weight: 70-100 parts of thermosetting resin composition, 0.05-0.15 part of catalyst, 3-15 parts of flame retardant, 45-65 parts of filler and 60-80 parts of organic solvent.
In the present invention, the curing agent may be at least one selected from the group consisting of 1-benzylbenzene-2-ethylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-aminoethyl-2-methylimidazole and 1-cyanoethylimidazole.
In the present invention, the flame retardant may be selected from at least one of a phosphorus-based flame retardant and a nitrogen-based flame retardant, wherein the phosphorus-based flame retardant may be selected from at least one of cresyldiphenyl phosphate, trichloropropyl phosphate, DOPO, hexaphenoxycyclotriphosphazene and 2, 6-xylenyl-1, 3-phenylene phosphate tetraester, and the nitrogen-based flame retardant may be selected from at least one of melamine and melamine phosphate.
In the present invention, the inorganic filler may be at least one selected from the group consisting of magnesium hydroxide, aluminum hydroxide monohydrate, fine fused silica powder, talc and barium sulfate.
In the present invention, the solvent may be at least one selected from the group consisting of propylene glycol methyl ether, propylene glycol methyl ether acetate, cyclohexanone, methyl ethyl ketone, acetone, methanol and xylene.
The preparation method of the glue solution for the halogen-free low-loss copper-clad plate can comprise the following steps:
according to the weight parts, adding epoxy resin, polystyrene allyl glycidyl ether resin, cyanate ester resin, bismaleimide resin and phosphorus-containing phenolic resin into a solvent, stirring for 1-3h at 1400-1600r/min, then adding a catalyst, a flame retardant and a filler, stirring for 2-4h at 800-1200r/min, and then stirring for 1-3h at 400-600r/min to prepare the glue solution for the halogen-free low-loss copper-clad plate.
The invention also provides a preparation method of the halogen-free low-loss copper-clad plate, which comprises the following steps:
s1: preparing the glue solution for the halogen-free low-loss copper-clad plate into a prepreg;
s2: and laminating the prepreg and the copper foil after overlapping to obtain the halogen-free low-loss copper-clad plate.
Specifically, when the prepreg is prepared, the glue content can be controlled to be 40-50%, the fluidity is 15-50%, and the gelling time is 140-; during lamination, the temperature can be controlled to be 220-240 ℃, the pressure can be controlled to be 410-430psi, and the lamination time can be 3.5-4.5 h.
The invention also provides a halogen-free low-loss copper-clad plate which is prepared according to the preparation method.
The resin system disclosed by the invention well overcomes the inherent defects of the existing bismaleimide resin and a bismaleimide and cyanate ester composite resin system, and realizes the advantages of low expansion coefficient, high Tg (glass transition temperature) up to 250 ℃, good heat resistance and dielectric property, low dielectric loss and the like, so that the resin system can be well applied to a printed circuit board of a packaging carrier plate.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms also include the plural forms unless the context clearly dictates otherwise, and further, it is understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of the stated features, steps, operations, devices, components, and/or combinations thereof.
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be understood that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparation of polystyrene allyl glycidyl ether resin
Adding 80 parts of cyclohexanone, 208 parts of styrene and 114 parts of allyl glycidyl ether into a four-neck flask with a stirrer and a thermometer, and starting stirring; when the temperature is raised to about 85 ℃, 0.03 part of tert-butyl peroxybenzoate and 0.005 part of hydroquinone are added, then the temperature is slowly raised to 95 ℃, and the reaction is carried out for 3 hours under the condition of heat preservation, thus obtaining the yellow polystyrene allyl glycidyl ether resin.
Secondly, preparing glue solution for halogen-free low-loss copper-clad plate
The glue solution for the halogen-free low-loss copper-clad plate comprises the following components:
o-cresol type epoxy resin: 8 portions of
Trifunctional epoxy resin: 5 portions of
Polystyrene allyl glycidyl ether resin: 10 portions of
Bisphenol a type cyanate ester resin C01 PS: 30 portions of
Bismaleimide resin BMI-5100: 15 portions of
Phosphorus-containing phenolic resin LC-950PM 60: 7 portions of
2-ethyl-4-methylimidazole (2-E4 MZ): 0.05 part
Flame retardant DOPO: 15 portions of
Talc powder: 65 portions of
Propylene glycol methyl ether: 70 portions of
Cleaning a glue mixing tank by using acetone, adding the propylene glycol methyl ether solvent according to the weight part, adding resin components, stirring for 2 hours at 1500r/min to uniformly mix the resin, then adding the rest components, stirring for 3 hours at the rotating speed of 1000r/min, stirring for 2 hours at the rotating speed of 500r/min, and testing the gelation time of the glue to be qualified to obtain the glue solution.
Thirdly, preparing the halogen-free low-loss copper-clad plate
Preparing the prepared glue solution into a prepreg according to a conventional mode; wherein the content of the rubber is controlled to be 50%, the fluidity is controlled to be 38%, the gelling time is 150s, and the volatile matter is less than 0.5%.
And (3) taking 2 prepregs, covering a copper foil on each prepreg to form a combined stack, putting the stack into a hot press, and pressing for 4 hours under the conditions that the temperature is 230 ℃ and the pressure is 420psi to obtain the halogen-free low-loss copper-clad plate.
The halogen-free low-loss copper-clad plate is detected by the following method:
glass transition temperature (Tg): measured by Differential Scanning Calorimetry (DSC) according to the DSC method defined by IPC-TM-6502.4.25;
thermal stratification time T-288: measured according to the IPC-TM-6502.4.24.1 method;
thermal cracking temperature (Td): measured according to the method specified in IPC-TM-6502.4.25.6;
flame retardancy: measured according to the UL94 vertical burning method;
PCT + wicking: and (4) steaming the substrate for 2h in a PCT, and then placing the substrate into a tin furnace at 288 ℃ to test whether the substrate has white spots, delamination and foaming.
The performance test results of the halogen-free low-loss copper-clad plate are shown in table 1.
Example 2
First, glue solution for preparing halogen-free low-loss copper-clad plate
The glue solution for the halogen-free low-loss copper-clad plate comprises the following components, wherein the polystyrene allyl glycidyl ether resin prepared in the embodiment 1 is adopted as the polystyrene allyl glycidyl ether resin:
o-cresol type epoxy resin: 6 portions of
Trifunctional epoxy resin: 4 portions of
Polystyrene allyl glycidyl ether resin: 15 portions of
Bisphenol a type cyanate ester resin C01 PS: 25 portions of
Bismaleimide resin BMI-5100: 20 portions of
Phosphorus-containing phenolic resin LC-950PM 60: 5 portions of
2-ethyl-4-methylimidazole (2-E4 MZ): 0.1 part
Flame retardant DOPO: 10 portions of
Talc powder: 60 portions of
Propylene glycol methyl ether: 65 portions of
Cleaning a glue mixing tank by using acetone, adding the propylene glycol methyl ether solvent according to the weight part, adding resin components, stirring for 1h at 1600r/min to uniformly mix the resin, then adding the rest components, stirring for 2h at the rotating speed of 1200r/min, stirring for 3h at the rotating speed of 600r/min, and testing the gelation time of the glue to be qualified to obtain the glue solution.
Secondly, preparing the halogen-free low-loss copper-clad plate
Preparing the prepared glue solution into a prepreg according to a conventional mode; wherein, the content of the glue is controlled to be 45 percent, the fluidity is controlled to be 35 percent, the gelling time is 140s, and the volatile matter is less than 0.5 percent.
And (3) taking 2 prepregs, covering a copper foil on each prepreg to form a combined stack, putting the stack into a hot press, and pressing for 4.5 hours under the conditions that the temperature is 220 ℃ and the pressure is 430psi to obtain the halogen-free low-loss copper-clad plate.
The performance of the halogen-free low-loss copper-clad plate is detected by the detection method in the embodiment 1, and the performance detection result is shown in the table 1.
Example 3
Preparation of polystyrene allyl glycidyl ether resin
Adding 85 parts of cyclohexanone, 215 parts of styrene and 110 parts of allyl glycidyl ether into a four-neck flask with a stirrer and a thermometer, and starting stirring; when the temperature is raised to about 80 ℃, 0.02 part of tert-butyl peroxybenzoate and 0.006 part of hydroquinone are added, then the temperature is slowly raised to 90 ℃, and the heat preservation reaction is carried out for 3.5 hours, thus obtaining the yellow polystyrene allyl glycidyl ether resin.
Secondly, preparing glue solution for halogen-free low-loss copper-clad plate
The glue solution for the halogen-free low-loss copper-clad plate comprises the following components:
o-cresol type epoxy resin: 10 portions of
Trifunctional epoxy resin: 5 portions of
Polystyrene allyl glycidyl ether resin: 20 portions of
Bisphenol a type cyanate ester resin C01 PS: 35 portions of
Bismaleimide resin BMI-4000: 25 portions of
Phosphorus-containing phenolic resin XZ 92741: 5 portions of
2-methylimidazole: 0.15 part
Flame retardant tolyldiphenyl phosphate: 5 portions of
Aluminum hydroxide: 50 portions of
Cyclohexanone: 60 portions of
Cleaning a glue mixing tank by using acetone, adding the solvent cyclohexanone according to the weight part, adding all resin components, stirring for 3 hours at 1400r/min to uniformly mix the resin, then adding the rest components, stirring for 4 hours at the rotating speed of 800r/min, stirring for 3 hours at the rotating speed of 400r/min, and testing the gelation time of the glue to be qualified to obtain the glue solution.
Thirdly, preparing the halogen-free low-loss copper-clad plate
Preparing the prepared glue solution into a prepreg according to a conventional mode; wherein, the content of the glue is controlled to be 40 percent, the fluidity is controlled to be 30 percent, the gelling time is 160s, and the volatile matter is less than 0.5 percent.
And (3) taking 2 prepregs, covering a copper foil on each prepreg to form a combined stack, putting the stack into a hot press, and pressing for 3.5 hours under the conditions that the temperature is 240 ℃ and the pressure is 410psi to obtain the halogen-free low-loss copper-clad plate.
The performance of the halogen-free low-loss copper-clad plate is detected by the detection method in the embodiment 1, and the performance detection result is shown in the table 1.
Example 4
Preparation of polystyrene allyl glycidyl ether resin
Adding 75 parts of cyclohexanone into a four-neck flask with a stirrer and a thermometer, adding 200 parts of styrene and 120 parts of allyl glycidyl ether, and starting stirring; when the temperature is raised to about 90 ℃, 0.04 part of tert-butyl peroxybenzoate and 0.004 part of hydroquinone are added, then the temperature is slowly raised to 100 ℃, and the reaction is carried out for 2.5 hours under the condition of heat preservation, thus obtaining the yellow polystyrene allyl glycidyl ether resin.
Secondly, preparing glue solution for halogen-free low-loss copper-clad plate
The glue solution for the halogen-free low-loss copper-clad plate comprises the following components:
o-cresol type epoxy resin: 8 portions of
Trifunctional epoxy resin: 5 portions of
Polystyrene allyl glycidyl ether resin: 25 portions of
Bisphenol a type cyanate ester resin C01 PS: 15 portions of
Bismaleimide resin BMI-4000: 15 portions of
Phosphorus-containing phenolic resin XZ 92741: 10 portions of
2-ethyl-4-methylimidazole: 0.08 portion of
Flame retardant hexaphenoxycyclotriphosphazene: 3 portions of
Melting the silicon micro powder: 45 portions of
Xylene: 80 portions
Cleaning a glue mixing tank by using acetone, adding the solvent xylene according to the weight part, adding all resin components, stirring for 2 hours at 1500r/min to uniformly mix the resin, then adding the rest components, stirring for 3 hours at the rotating speed of 1000r/min, stirring for 2 hours at the rotating speed of 500r/min, and testing the gelation time of the glue to be qualified to obtain the glue solution.
Thirdly, preparing the halogen-free low-loss copper-clad plate
Preparing the prepared glue solution into a prepreg according to a conventional mode; wherein the content of the rubber is controlled to be 50%, the fluidity is controlled to be 38%, the gelling time is 150s, and the volatile matter is less than 0.5%.
And (3) taking 2 prepregs, covering a copper foil on each prepreg to form a combined stack, putting the stack into a hot press, and pressing for 4 hours under the conditions that the temperature is 230 ℃ and the pressure is 420psi to obtain the halogen-free low-loss copper-clad plate.
The performance of the halogen-free low-loss copper-clad plate is detected by the detection method in the embodiment 1, and the performance detection result is shown in the table 1.
Example 5
First, glue solution for preparing halogen-free low-loss copper-clad plate
The glue solution for the halogen-free low-loss copper-clad plate comprises the following components, wherein the polystyrene allyl glycidyl ether resin prepared in the embodiment 1 is adopted as the polystyrene allyl glycidyl ether resin:
o-cresol type epoxy resin: 5 portions of
Polystyrene allyl glycidyl ether resin: 30 portions of
Bisphenol a type cyanate ester resin C01 PS: 10 portions of
Bismaleimide BMI-5100: 20 portions of
Phosphorus-containing phenolic resin LC-950PM 60: 10 portions of
2-ethyl-4-methylimidazole (2-E4 MZ): 0.05 part
Flame retardant DOPO: 8 portions of
Talc powder: 55 portions of
Propylene glycol methyl ether: 75 portions of
Cleaning a glue mixing tank by using acetone, adding the propylene glycol methyl ether solvent according to the weight part, adding resin components, stirring for 1h at 1600r/min to uniformly mix the resin, then adding the rest components, stirring for 2h at the rotating speed of 1200r/min, stirring for 3h at the rotating speed of 600r/min, and testing the gelation time of the glue to be qualified to obtain the glue solution.
Secondly, preparing the halogen-free low-loss copper-clad plate
Preparing the prepared glue solution into a prepreg according to a conventional mode; wherein, the content of the glue is controlled to be 45 percent, the fluidity is controlled to be 35 percent, the gelling time is 140s, and the volatile matter is less than 0.5 percent.
And (3) taking 2 prepregs, covering a copper foil on each prepreg to form a combined stack, putting the stack into a hot press, and pressing for 4.5 hours under the conditions that the temperature is 220 ℃ and the pressure is 430psi to obtain the halogen-free low-loss copper-clad plate.
The performance of the halogen-free low-loss copper-clad plate is detected by the detection method in the embodiment 1, and the performance detection result is shown in the table 1.
Comparative example 1
The glue solution for copper-clad plates of the comparative example is basically the same as that of example 1 except that the composition of the thermosetting resin composition used is different from that of example 1.
The composition of the thermosetting resin composition of this comparative example was as follows:
o-cresol type epoxy resin: 13 portions of
Trifunctional epoxy resin: 10 portions of
Bisphenol a type cyanate ester resin C01 PS: 30 portions of
Bismaleimide BMI-5100: 15 portions of
Phosphorus-containing phenolic resin LC-950: 7 portions of
The performance of the copper-clad plate is detected by the detection method of the embodiment 1, and the performance detection result is shown in a table 2.
Comparative example 2
The glue solution for copper-clad plates of the comparative example is basically the same as that of example 1 except that the composition of the thermosetting resin composition used is different from that of example 1.
The composition of the thermosetting resin composition of this comparative example was as follows:
o-cresol type epoxy resin: 8 portions of
Trifunctional epoxy resin: 5 portions of
Polystyrene allyl glycidyl ether resin: 40 portions of
Bismaleimide resin BMI-5100: 15 portions of
Phosphorus-containing phenolic resin LC-950PM 60: 7 portions of
The performance of the copper-clad plate is detected by the detection method of the embodiment 1, and the performance detection result is shown in a table 2.
Comparative example 3
The glue solution for copper-clad plates of the comparative example is basically the same as that of example 1 except that the composition of the thermosetting resin composition used is different from that of example 1.
The composition of the thermosetting resin composition of this comparative example was as follows:
o-cresol type epoxy resin: 8 portions of
Trifunctional epoxy resin: 5 portions of
SMA resin: 10 portions of
Bisphenol a type cyanate ester resin C01 PS: 30 portions of
Bismaleimide resin BMI-5100: 15 portions of
Phosphorus-containing phenolic resin LC-950PM 60: 7 portions of
The performance of the copper-clad plate is detected by the detection method of the embodiment 1, and the performance detection result is shown in a table 2.
Table 1 performance test results of halogen-free low-loss copper-clad plate in each example
| Test items | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Tg(DSC)/℃ | 271 | 267 | 262 | 259 | 256 |
| Thermal stratification time T288(TMA) | ＞60 | ＞60 | ＞60 | ＞60 | ＞60 |
| Thermal cracking temperature Td (5%/TGA) | 450 | 430 | 420 | 400 | 390 |
| CTE(50-260℃) | 1.81 | 1.83 | 1.82 | 1.79 | 1.80 |
| Flame retardancy (UL94) | V-0 | V-0 | V-0 | V-0 | V-0 |
| Peel strength (lb/in)1OZ | 6.6 | 6.5 | 6.2 | 5.9 | 5.9 |
| Solder heat resistance (288 ℃ C.) 10 s/time | ＞15 | ＞15 | ＞15 | ＞15 | ＞15 |
| Solder heat resistance (288 ℃ C.) 60 s/time | ＞5 | ＞5 | ＞5 | ＞5 | ＞5 |
| Dielectric constant (RC: 50%, Dk,10G) | 4.06 | 3.98 | 3.87 | 4.02 | 3.78 |
| Dielectric loss (RC: 50%, Df,10G) | 0.011 | 0.009 | 0.0087 | 0.0084 | 0.0073 |
| PCT (PCT120 x 2h) + tin immersion (20s) | √ | √ | √ | √ | √ |
Table 2 comparison of performance test results of copper-clad plates of example 1 and comparative examples 1 to 3
As can be seen from tables 1 and 2:
the specific resin system of the invention well solves the defects of the prior bismaleimide resin and the composite resin system of bismaleimide and cyanate, realizes the advantages of low expansion coefficient, high heat resistance with the glass transition temperature of 250 ℃, low dielectric constant, low dielectric loss, stable size stability and the like, and can be well applied to the printed circuit board of the packaging carrier plate.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. The thermosetting resin composition is characterized by comprising the following components in parts by weight: 5-15 parts of epoxy resin, 10-30 parts of polystyrene allyl glycidyl ether resin, 10-35 parts of cyanate ester resin, 15-25 parts of bismaleimide resin and 5-10 parts of phosphorus-containing phenolic resin.
2. The thermosetting resin composition claimed in claim 1, wherein the epoxy resin is at least one selected from the group consisting of bisphenol a type epoxy resin, bisphenol F type novolac epoxy resin, novolac type epoxy resin, o-cresol novolac type epoxy resin, DCPD type epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin and biphenyl type epoxy resin.
3. The thermosetting resin composition of claim 1, wherein the polystyrene allyl glycidyl ether resin is prepared by a method comprising:
uniformly mixing 75-85 parts of cyclohexanone, 200-215 parts of styrene and 110-120 parts of allyl glycidyl ether, heating to 80-90 ℃, adding 0.02-0.04 part of tert-butyl peroxybenzoate and 0.004-0.006 part of hydroquinone into the heated mixture, uniformly mixing, continuously heating to 90-100 ℃, and carrying out heat preservation reaction for 2.5-3.5 hours to obtain the polystyrene allyl glycidyl ether resin.
4. The thermosetting resin composition according to claim 1, wherein the cyanate ester resin is at least one selected from the group consisting of bisphenol a type cyanate ester resins and phenol type cyanate ester resins.
5. The glue solution for the halogen-free low-loss copper-clad plate is characterized by comprising the following components in parts by weight: 70 to 100 parts of the thermosetting resin composition according to any one of claims 1 to 4, 0.05 to 0.15 part of a catalyst, 3 to 15 parts of a flame retardant, 45 to 65 parts of a filler and 60 to 80 parts of an organic solvent.
6. The glue solution for halogen-free low-loss copper-clad plates according to claim 5, wherein the catalyst is at least one selected from 1-benzyl benzene-2-ethylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-aminoethyl-2-methylimidazole and 1-cyanoethylimidazole.
7. The glue solution for halogen-free low-loss copper-clad plates according to claim 5, wherein the flame retardant is at least one selected from phosphorus flame retardants and nitrogen flame retardants, wherein the phosphorus flame retardants are at least one selected from diphenyl cresyl phosphate, trichloropropyl phosphate, DOPO, hexaphenoxycyclotriphosphazene and 2, 6-xylenyl 1, 3-phenylene phosphate tetraester, and the nitrogen flame retardants are at least one selected from melamine and melamine phosphate.
8. The glue solution for the halogen-free low-loss copper-clad plate according to claim 5, wherein the inorganic filler is at least one selected from magnesium hydroxide, aluminum hydroxide monohydrate, fused silica micropowder, talcum powder and barium sulfate; the solvent is at least one selected from propylene glycol methyl ether, propylene glycol methyl ether acetate, cyclohexanone, butanone, acetone, methanol and xylene.
9. The preparation method of the halogen-free low-loss copper-clad plate is characterized by comprising the following steps of:
s1: preparing the glue solution for the copper-clad plate according to any one of claims 5 to 8 into a prepreg;
s3: and laminating the prepreg and the copper foil after overlapping to obtain the halogen-free low-loss copper-clad plate.
10. A halogen-free low-loss copper-clad plate, which is characterized by being prepared according to the preparation method of claim 9.
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Application publication date: 20210625 |