CN114231221B - Insulating adhesive film and preparation method and application thereof - Google Patents
Insulating adhesive film and preparation method and application thereof Download PDFInfo
- Publication number
- CN114231221B CN114231221B CN202111638251.9A CN202111638251A CN114231221B CN 114231221 B CN114231221 B CN 114231221B CN 202111638251 A CN202111638251 A CN 202111638251A CN 114231221 B CN114231221 B CN 114231221B
- Authority
- CN
- China
- Prior art keywords
- parts
- resin
- benzocyclobutene
- adhesive film
- insulating adhesive
- Prior art date
- 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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- 239000002313 adhesive film Substances 0.000 title claims abstract description 103
- 238000002360 preparation method Methods 0.000 title abstract description 30
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical class C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims abstract description 86
- 229920005989 resin Polymers 0.000 claims abstract description 69
- 239000011347 resin Substances 0.000 claims abstract description 69
- -1 polycyclic modified benzocyclobutene Chemical class 0.000 claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 27
- 239000011737 fluorine Substances 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 24
- 150000003254 radicals Chemical class 0.000 claims abstract description 11
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 7
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract description 6
- 238000011049 filling Methods 0.000 claims abstract description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000003822 epoxy resin Substances 0.000 claims description 18
- 229920000647 polyepoxide Polymers 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 13
- 229920000090 poly(aryl ether) Polymers 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012621 metal-organic framework Substances 0.000 claims description 12
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 150000001718 carbodiimides Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- XXZOEDQFGXTEAD-UHFFFAOYSA-N 1,2-bis(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1C(F)(F)F XXZOEDQFGXTEAD-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004962 Polyamide-imide Substances 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 229920006287 phenoxy resin Polymers 0.000 claims description 6
- 239000013034 phenoxy resin Substances 0.000 claims description 6
- 229920002312 polyamide-imide Polymers 0.000 claims description 6
- 229920005990 polystyrene resin Polymers 0.000 claims description 6
- 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 description 5
- 239000011256 inorganic filler Substances 0.000 claims description 5
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 5
- 229920005668 polycarbonate resin Polymers 0.000 claims description 5
- 239000004431 polycarbonate resin Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 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
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
- DJOYTAUERRJRAT-UHFFFAOYSA-N 2-(n-methyl-4-nitroanilino)acetonitrile Chemical compound N#CCN(C)C1=CC=C([N+]([O-])=O)C=C1 DJOYTAUERRJRAT-UHFFFAOYSA-N 0.000 claims description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 2
- 239000004695 Polyether sulfone Substances 0.000 claims description 2
- 239000004697 Polyetherimide Substances 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 239000011354 acetal resin Substances 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 claims description 2
- RRZKHZBOZDIQJG-UHFFFAOYSA-N azane;manganese Chemical compound N.[Mn] RRZKHZBOZDIQJG-UHFFFAOYSA-N 0.000 claims description 2
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002113 barium titanate Inorganic materials 0.000 claims description 2
- 229910021523 barium zirconate Inorganic materials 0.000 claims description 2
- DQBAOWPVHRWLJC-UHFFFAOYSA-N barium(2+);dioxido(oxo)zirconium Chemical compound [Ba+2].[O-][Zr]([O-])=O DQBAOWPVHRWLJC-UHFFFAOYSA-N 0.000 claims description 2
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 claims description 2
- 229910002115 bismuth titanate Inorganic materials 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
- 229910001593 boehmite Inorganic materials 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 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
- 229910052878 cordierite Inorganic materials 0.000 claims description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 2
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 2
- 229960001545 hydrotalcite Drugs 0.000 claims description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 2
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 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
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920001225 polyester resin Polymers 0.000 claims description 2
- 239000004645 polyester resin Substances 0.000 claims description 2
- 229920006393 polyether sulfone Polymers 0.000 claims description 2
- 229920002530 polyetherether ketone Polymers 0.000 claims description 2
- 229920001601 polyetherimide Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 239000009719 polyimide resin Substances 0.000 claims description 2
- 229920005672 polyolefin resin Polymers 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910000018 strontium carbonate Inorganic materials 0.000 claims description 2
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000013086 titanium-based metal-organic framework Substances 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 239000013094 zinc-based metal-organic framework Substances 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 229910000166 zirconium phosphate Inorganic materials 0.000 claims description 2
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 claims description 2
- 239000013096 zirconium-based metal-organic framework Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000004643 cyanate ester Substances 0.000 claims 1
- 238000011161 development Methods 0.000 abstract description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000003989 dielectric material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 239000013154 zeolitic imidazolate framework-8 Substances 0.000 description 6
- MFLKDEMTKSVIBK-UHFFFAOYSA-N zinc;2-methylimidazol-3-ide Chemical compound [Zn+2].CC1=NC=C[N-]1.CC1=NC=C[N-]1 MFLKDEMTKSVIBK-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000013461 design Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229920006389 polyphenyl polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000008054 signal transmission Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000013207 UiO-66 Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 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 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/24—Homopolymers or copolymers of amides or imides
-
- 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
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
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- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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- C09J2433/00—Presence of (meth)acrylic polymer
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Abstract
The invention provides an insulating adhesive film, and a preparation method and application thereof. The insulating adhesive film comprises the following components in parts by weight: 20-50 parts of modified benzocyclobutene, 30-60 parts of free radical polymer, 120-150 parts of inorganic filling material, 3-5 parts of thermoplastic resin and 10-30 parts of thermosetting resin; the modified benzocyclobutene is selected from fluorine-containing modified benzocyclobutene and/or polycyclic modified benzocyclobutene. The insulating adhesive film provided by the invention has excellent dielectric property and lower dielectric loss, and can meet the requirements of high-speed and high-integration development of electronic components.
Description
Technical Field
The invention belongs to the technical field of resin composite materials, and particularly relates to an insulating adhesive film, a preparation method and application thereof.
Background
With the advent of the 5G communications era, electronic components have rapidly evolved toward higher speeds and higher integration levels. However, with the increase of the wiring density of the very large scale integrated circuit, the resistance of the metal interconnection wires and the capacitance of the interlayer dielectric in the electronic component easily form RC delay (resistance-capacitance delay) effect, thereby causing adverse effects such as signal transmission delay, noise interference and power loss. In the high-speed and high-frequency transmission technology, the signal transmission speed (v) and the signal propagation loss rate (α) of the dielectric material are two key performance indexes, and the v value and the α value are closely related to the dielectric constant (Dk) of the dielectric material, and in general, the v value of the high-frequency circuit board is inversely proportional to the Dk of the dielectric material, and the α value is directly proportional to the dielectric constant (Dk) and the dielectric loss (Df) of the dielectric material. Therefore, developing insulating dielectric materials with low Dk and low Df is of great value to reduce interconnect delay, power consumption, and cross-talk.
CN113185940a discloses an insulating film composition and its application in printed circuit boards. The insulating adhesive film composition comprises, by mass, 0.5-5 parts of polystyrene resin, 5-50 parts of epoxy resin, 2-20 parts of curing agent, 0.01-1 part of curing accelerator and 1-100 parts of inorganic filler; the polystyrene resin is a polystyrene resin with oxazoline skeletons. According to the technical scheme, the oxazoline skeleton polystyrene resin is introduced into the epoxy resin composition, so that the effect of low dielectric property is achieved, and the better binding force is obtained with lower surface roughness. These two improvements, while providing low loss insulation effects to accommodate high performance printed circuit board applications, still result in greater dielectric losses in the resulting insulation film compositions.
CN111806016a discloses an insulating adhesive film and a preparation method thereof. The insulating adhesive film is composed of a three-layer structure, the insulating adhesive film is sequentially composed of a supporting film, a dielectric film and a covering film from bottom to top, the dielectric film is arranged in the middle to form a sandwich structure, the dielectric film comprises an upper dielectric layer structure, a middle dielectric layer structure and a lower dielectric layer structure, the upper dielectric layer material and the lower dielectric layer material are made of epoxy resin compound electronic paste, the filler content in the epoxy resin compound electronic paste is 8-40 wt%, the middle dielectric layer material is made of epoxy resin compound electronic paste, and the filler content in the epoxy resin compound electronic paste is 40-90 wt%. The insulating adhesive film provided by the technical scheme balances the relationship among the thermal expansion coefficient, the mechanical strength and the binding force, can be applied to dielectric layers in the semiconductor electronic packaging fields such as packaging substrates, packaging carrier plates, fan-out type plate level packaging rewiring and the like, has high peeling strength (more than 0.8N/mm) and low thermal expansion coefficient (less than 30 ppm/K), but the dielectric loss of the insulating adhesive film composition prepared by the insulating adhesive film is larger.
CN108440903a discloses a halogen-free resin composition and a low-fluidity prepreg thereof. The halogen-free resin composition comprises the following components in parts by weight: 20-80 parts of epoxy resin composition, 10-50 parts of phenol-oxygen resin, 10-50 parts of flame retardant, 3-30 parts of flexibilizer, 10-80 parts of inorganic filler, 1-10 parts of curing agent, 0-5 parts of accelerator and 0-80 parts of additive. The epoxy resin prepared by the technical proposal has lower viscosity and better wettability, but has higher dielectric loss and poorer electrochemical performance,
although the insulating adhesive film is widely applied to the fields of printed circuit boards, chip packaging and the like, the existing insulating adhesive film material has insufficient dielectric property and seriously affects the application of the insulating adhesive film material in integrated circuits. The insulating film product with good dielectric properties can meet the requirements of high-speed and high-integration development of electronic components, so that how to improve the dielectric properties of the insulating film, reduce the dielectric loss of the insulating film and increase the signal transmission speed and circuit density becomes a technical problem to be solved urgently by those skilled in the art.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an insulating adhesive film, and a preparation method and application thereof. According to the invention, through the design of the components of the insulating adhesive film, the specific modified benzocyclobutene is further used, so that the prepared insulating adhesive film has excellent dielectric property and lower dielectric loss, and can meet the requirements of high-speed and high-integration development of electronic components.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the invention provides an insulating adhesive film, which comprises the following components in parts by weight:
20-50 parts of modified benzocyclobutene, 30-60 parts of free radical polymer, 120-150 parts of inorganic filling material, 3-5 parts of thermoplastic resin and 10-30 parts of thermosetting resin;
the modified benzocyclobutene is selected from fluorine-containing modified benzocyclobutene and/or polycyclic modified benzocyclobutene.
In the invention, fluorine atoms can be introduced into the insulating adhesive film by using fluorine-containing modified benzocyclobutene, and the fluorine atoms have strong electron-withdrawing capability and better fixing effect on electrons, so that the doping of the fluorine atoms can reduce the regularity of molecular chains, and the molecular chains of the polymer are stacked more irregularly, thereby reducing the electron and ion polarizability of the polymer; in addition, since the C-F bond has a smaller polarizability than the C-H bond, the introduction of the C-F bond into the polymer, particularly the introduction of bulky side-CF having a low molar polarizability into the polymer 3 The electron and ion polarizability of the polymer can be further reduced. The prepared insulating adhesive film has lower dielectric constant and dielectric loss through the use of fluorine-containing modified benzocyclobutene.
Meanwhile, the chemical bond polarization rate in the large-volume functional group is low, and the free volume of the polymer can be increased due to the large-volume structure contained in the functional group, so that the low-polarity large-volume rigid functional group can be introduced into the insulating adhesive film through the use of the polycyclic modified benzocyclobutene, and further the dielectric property, the thermal stability and the like of the insulating adhesive film can be improved.
In the present invention, the weight part of the modified benzocyclobutene may be 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, or the like.
The weight parts of the radical polymer may be 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, 55 parts, 60 parts, or the like.
The inorganic filler may be 120 parts, 123 parts, 125 parts, 127 parts, 130 parts, 133 parts, 136 parts, 139 parts, 142 parts, 146 parts, 150 parts, or the like.
The thermoplastic resin may be 3 parts, 3.2 parts, 3.4 parts, 3.6 parts, 3.8 parts, 4 parts, 4.2 parts, 4.4 parts, 4.6 parts, 4.8 parts, 5 parts, etc. by weight.
The weight parts of the thermosetting resin may be 10 parts, 12 parts, 14 parts, 16 parts, 18 parts, 20 parts, 22 parts, 24 parts, 26 parts, 28 parts, 30 parts, or the like.
The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention.
As a preferable technical scheme of the invention, the modified benzocyclobutene is fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene.
Preferably, the mass ratio of the fluorine-containing modified benzocyclobutene to the polycyclic modified benzocyclobutene is 1 (1.5-2.4), for example, 1:1.5, 1:1.6, 1:1.7, 1:1.8, 1:1.9, 1:2, 1:2.1, 1:2.2, 1:2.3, 1:2.4 or the like can be adopted.
According to the invention, through the cooperation of the fluorine-containing modified benzocyclobutene and the polycyclic modified benzocyclobutene, the dielectric loss of the insulating adhesive film can be further reduced through the synergistic effect of the fluorine-containing modified benzocyclobutene and the polycyclic modified benzocyclobutene, and the prepared insulating adhesive film with excellent dielectric performance can meet the requirements of high-speed and high-integration development of electronic components.
Meanwhile, the excessive addition of the fluorine-containing modified benzocyclobutene can cause poor compatibility with other components of the insulating adhesive film, so that the mass ratio of the fluorine-containing modified benzocyclobutene to the polycyclic modified benzocyclobutene is controlled within a specific range, the fluorine-containing modified benzocyclobutene and the other components of the insulating adhesive film have better compatibility, and the insulating adhesive film with excellent dielectric property can be prepared. If the mass ratio of the two is too small, the dielectric loss of the prepared insulating adhesive film is larger; if the mass ratio of the fluorine element and the fluorine element is too large, the compatibility among the components of the insulating adhesive film is poor, and the prepared insulating adhesive film is poor in dielectric property and mechanical property, and is not friendly to the environment because the fluorine element is easy to pollute.
Preferably, the fluorine-containing modified benzocyclobutene is selected from any one or a combination of at least two of hexafluorocyclobutane benzocyclobutene, octafluorocyclopentenyl benzocyclobutene, benzocyclobutene containing a bis (trifluoromethyl) benzene ring structure or benzocyclobutene containing a fluorinated polyarylether structure.
In the present invention, the specific structure and preparation method of benzocyclobutene containing bis (trifluoromethyl) benzene ring structure or benzocyclobutene containing fluorinated polyarylether structure are not limited in any way, and only the benzocyclobutene containing bis (trifluoromethyl) benzene ring structure is needed to contain corresponding structure, and the benzocyclobutene containing bis (trifluoromethyl) benzene ring structure used in the present invention is prepared by the following steps of' A new low dielectric material with high thermostability based on a thermosetting trifluoromethyl substituted aromatic molecule [ J ], RSC Adv,2013,4:23128-23132", benzocyclobutene containing fluorinated polyarylether structures is prepared by the method described in" Postpolymerization of a Fluorinated and Reactive Poly (aryl ether): an Efficient Way To Balance the Solubility and Solvent Resistance of the Polymer [ J ], ACS appl. Mater. Interfaces 2014,6:20437-20443 ".
Preferably, the polycyclic modified benzocyclobutene is selected from benzocyclobutene containing a fluorenyl structure and/or benzocyclobutene containing adamantane.
In the invention, the specific structure and preparation method of benzocyclobutene containing fluorenyl structure and/or benzocyclobutene containing adamantane are not limited in any way, and the benzocyclobutene containing fluorenyl structure is prepared by the method described in 'Benzocyclobutene resin with fluorene backbone: a novel thermosetting material with high thermostability and low dielectric constant [ J ], RSC adv, 2014,4,39884-39888'; the benzocyclobutene containing adamantane is prepared by the method described in "Adamantyl-based benzocyclobutene low-k polymers with good physical properties and excellent planarity [ J ], J.Mater.chem.C., 2015,3,3364-3370".
As a preferable embodiment of the present invention, the radical polymer is selected from any one or a combination of at least two of a maleimide-containing radical polymer, a vinylphenyl radical polymer, a (meth) acrylic radical polymer, an allylic radical polymer, and a butadiene radical polymer.
Preferably, the radical polymer is selected from any one or a combination of at least two of biphenyl aralkyl type maleimide resin, liquid bismaleimide resin, low polyphenylene ether-styrene resin or (meth) acrylic radical polymer.
The low polyphenylene ether-styrene resin in the present invention was OPE-2St 1200 produced by Mitsubishi gas chemical corporation, and the (meth) acrylic acid-based free radical polymer was NK Ester A-DOG produced by Xinzhou chemical industry Co.
Preferably, the inorganic filler material is selected from any one or a combination of at least two of silica, alumina, glass, cordierite, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate, calcium zirconate, or zirconium phosphate.
As a preferable embodiment of the present invention, the thermoplastic resin is selected from any one or a combination of at least two of polyimide resin, polycarbonate resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyetheretherketone resin, polystyrene resin, polyester resin, or bisphenol ether resin.
Preferably, the thermosetting resin is selected from any one or a combination of at least two of epoxy resin, phenol resin, naphthol resin, benzoxazine resin, active ester resin, cyanate resin, carbodiimide resin, amine resin or anhydride resin.
As a preferable technical scheme of the invention, the insulating adhesive film further comprises 1-3 parts of MOFs material, for example, 1 part, 1.2 parts, 1.4 parts, 1.6 parts, 1.8 parts, 2 parts, 2.2 parts, 2.4 parts, 2.6 parts, 2.8 parts or 3 parts, etc.
The MOFs material has a hollow structure, an air medium can be introduced into the resin, and the dielectric constant and dielectric loss of the insulating adhesive film can be further reduced by using the MOFs with low addition amount in the invention, so that the insulating adhesive film with excellent dielectric property is prepared.
Preferably, the MOFs material is selected from any one or a combination of at least two of zeolite imidazole type zinc-based MOFs, amino-functionalized titanium-based MOFs or fluorine-functionalized zirconium-based MOFs.
In the invention, the MOFs material is more preferably ZIF-8 or NH 2 -any one or a combination of at least two of MILs-125 (Ti) or F4-UiO-66 (Zr).
As a preferable embodiment of the present invention, the insulating film further includes 1 to 1.5 parts of a curing accelerator, for example, 1 part, 1.1 parts, 1.2 parts, 1.3 parts, 1.4 parts, or 1.5 parts.
Preferably, the curing accelerator is selected from any one or a combination of at least two of a phosphorus-based curing accelerator, an amine-based curing accelerator, an imidazole-based curing accelerator, a guanidine-based curing accelerator, and a metal-based curing accelerator.
Preferably, the insulating film further includes 100-300 parts of an organic solvent, for example, 100 parts, 120 parts, 140 parts, 160 parts, 180 parts, 200 parts, 220 parts, 240 parts, 260 parts, 280 parts or 300 parts, etc.
Preferably, the organic solvent is selected from any one or a combination of at least two of toluene, xylene, butanone, methyl ethyl ketone, cyclohexanone, ethyl acetate or N, N-dimethylformamide.
In the present invention, according to actual production requirements, the insulating adhesive film further includes other additives, which illustratively include, but are not limited to: thickening agents, defoaming agents, leveling agents, adhesion imparting agents, coloring agents, and the like.
The thickness of the insulating film is 10 to 100. Mu.m, for example, 10. Mu.m, 20. Mu.m, 30. Mu.m, 40. Mu.m, 50. Mu.m, 60. Mu.m, 70. Mu.m, 80. Mu.m, 90. Mu.m, 100. Mu.m, etc. as a preferable embodiment of the present invention.
In a second aspect, the present invention provides a method for preparing the insulating film according to the first aspect, the method comprising the steps of:
and uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a substrate, and drying to obtain the insulating adhesive film.
In a preferred embodiment of the present invention, the thickness of the base material is 10 to 150 μm (for example, 10 μm, 20 μm, 25 μm, 30 μm, 40 μm, 50 μm, 60 μm, 70 μm, 80 μm, 90 μm, 100 μm, 110 μm, 120 μm, 130 μm, 140 μm, 150 μm, etc.), and more preferably 25 to 50 μm.
It should be noted that the present invention is not limited to the choice of the substrate, and any substrate commonly used in the art may be used, and examples include, but are not limited to: PET release film, polyethylene film, polypropylene film or polyvinyl chloride film. Meanwhile, in order to facilitate the subsequent removal of the base material, the polyethylene film, the polypropylene film or the polyvinyl chloride film can be subjected to corona treatment in advance before use.
Preferably, the drying temperature is 80 to 130 ℃, and may be 80 ℃, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃, 110 ℃, 115 ℃, 120 ℃, 125 ℃, 130 ℃ or the like, for example.
Preferably, the drying time is 3 to 10min, for example, 3min, 4min, 5min, 6min, 7min, 8min, 9min or 10min, etc.
Preferably, the drying further comprises a post-treatment step.
Preferably, the post-treatment is performed by removing the substrate.
In a third aspect, the present invention provides an application of the insulating film according to the first aspect in printed circuit board and chip packaging.
Compared with the prior art, the invention has the following beneficial effects:
according to the invention, through the design of the components of the insulating adhesive film, the modified benzocyclobutene and MOFs material are further used, so that the prepared insulating adhesive film has excellent dielectric properties, the dielectric constant is 2.6-2.8, the dielectric loss tangent is 0.0016-0.0021, and the requirements of high-speed and high-integration development of electronic components can be met.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Some of the component sources in the examples and comparative examples are as follows:
biphenyl aralkyl maleimide resin: MIR-3000-70MT of Japanese chemical Co., ltd;
liquid bismaleimide resin: DESIGNER MOLECULES company, BMI689;
low polyphenylene ether-styrene resin: mitsubishi gas chemical company, OPE-2St 1200;
(meth) acrylic radical polymer: NK Ester A-DOG, new Medium chemical industry Co;
polyamide imide resin: DIC, UNICIC V-8000;
phenoxy resin: mitsubishi chemical corporation, YX7553BH30;
polycarbonate resin: mitsubishi gas chemical corporation, FPC2136;
naphthalene type epoxy resin: DIC, inc., HP4032H;
carbodiimide resin: japanese spinning chemical Co., ltd., V-03;
active ester resin: DIC company, HPC-8000-65T;
curing accelerator: PERHEXYL D, a company of solar oil;
PET release film: and 3-15N/25mm (7475 adhesive tape) without silicon and fluorine release force.
Example 1
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
20 parts of hexafluorocyclobutane benzocyclobutene, 50 parts of biphenyl aralkyl type maleimide resin, 10 parts of liquid bismaleimide resin, 150 parts of silicon dioxide, 5 parts of polyamide imide resin, 10 parts of naphthalene type epoxy resin, 1 part of ZIF-8 1 parts of curing accelerator and 300 parts of cyclohexanone.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a PET release film, drying the PET release film at 80 ℃ for 10min, and removing the PET release film to obtain the insulating adhesive film with the thickness of 100 mu m.
Example 2
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
50 parts of benzocyclobutene containing fluorenyl structure, 30 parts of biphenyl aralkyl maleimide resin, 130 parts of silicon dioxide, 3 parts of phenoxy resin, 10 parts of naphthalene type epoxy resin, 5 parts of carbodiimide resin, 13 parts of active ester resin, 1 part of curing accelerator, 0.1 part of 4-Dimethylaminopyridine (DMAP), 8 1 parts of ZIF-and 100 parts of toluene.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a PET release film, drying the PET release film at 130 ℃ for 3min, and removing the PET release film to obtain the insulating adhesive film with the thickness of 10 mu m.
Example 3
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
20 parts of hexafluorocyclobutane benzocyclobutene, 30 parts of benzocyclobutene containing fluorenyl structure, 39 parts of low polyphenyl ether-styrene resin, 5 parts of (methyl) acrylic radical polymer, 120 parts of silicon dioxide, 5 parts of polycarbonate resin, 10 parts of naphthalene type epoxy resin, 8 1 parts of ZIF-8 1 parts, 1.5 parts of curing accelerator and 300 parts of cyclohexanone.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a PET release film, drying the PET release film at 110 ℃ for 5min, and removing the PET release film to obtain the insulating adhesive film with the thickness of 60 mu m.
Example 4
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
40 parts of octafluorocyclopentenyl benzocyclobutene, 50 parts of biphenyl aralkyl type maleimide resin, 10 parts of liquid bismaleimide, 150 parts of silicon dioxide, 5 parts of polyamide imide resin, 10 parts of naphthalene type epoxy resin, 1 part of curing accelerator and NH 2 2 parts of MIL-125 (Ti) and 300 parts of cyclohexanone.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a PET release film, drying the PET release film at 80 ℃ for 10min, and removing the PET release film to obtain the insulating adhesive film with the thickness of 100 mu m.
Example 5
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
40 parts of adamantane-containing benzocyclobutene, 30 parts of biphenyl aralkyl maleimide resin, 130 parts of silicon dioxide, 3 parts of phenoxy resin, 10 parts of naphthalene type epoxy resin, 5 parts of carbodiimide resin, 13 parts of active ester resin, 1 part of curing accelerator, 0.1 part of 4-dimethylaminopyridine and NH 2 2 parts of MIL-125 (Ti) and 300 parts of cyclohexanone.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a PET release film, drying the PET release film at 130 ℃ for 3min, and removing the PET release film to obtain the insulating adhesive film with the thickness of 10-100 mu m.
Example 6
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
15 parts of octafluorocyclopentenyl benzocyclobutene, 30 parts of adamantane-containing benzocyclobutene, 39 parts of low-polyphenyl ether-styrene resin, 5 parts of methacrylic acid free radical polymer, 120 parts of silicon dioxide, 5 parts of polycarbonate resin, 10 parts of naphthalene type epoxy resin, 1.5 parts of curing accelerator and NH 2 2 parts of MIL-125 (Ti) and 100 parts of methyl ethyl ketone
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a substrate, drying the substrate at 130 ℃ for 3min, and removing the substrate to obtain the insulating adhesive film with the thickness of 10 mu m.
Example 7
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
8 parts of benzocyclobutene containing a bis (trifluoromethyl) benzene ring structure, 8 parts of benzocyclobutene containing a fluorinated polyarylether structure, 35 parts of benzocyclobutene containing a fluorenyl structure, 30 parts of biphenyl aralkyl maleimide resin, 130 parts of silicon dioxide, 3 parts of phenoxy resin, 10 parts of naphthalene type epoxy resin, 5 parts of carbodiimide resin, 13 parts of active ester resin, 1 part of curing accelerator, 0.1 part of 4-dimethylaminopyridine, 3 parts of F4-UiO-66 (Zr) and 150 parts of toluene.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a substrate, drying the substrate at 100 ℃ for 7min, and removing the substrate to obtain the insulating adhesive film with the thickness of 50 mu m.
Example 8
The embodiment provides an insulating adhesive film and a preparation method thereof, wherein the insulating adhesive film comprises the following components in parts by weight:
10 parts of benzocyclobutene containing fluorinated polyarylether structure, 20 parts of benzocyclobutene containing fluorenyl structure, 30 parts of biphenyl aralkyl maleimide resin, 20 parts of low polyphenyl ether-styrene resin, 130 parts of silicon dioxide, 4 parts of polyamide imide resin, 15 parts of carbodiimide resin, 15 parts of active ester resin and NH 2 3 parts of MIL-125 (Ti), 1.2 parts of a curing accelerator and 200 parts of N, N-dimethylformamide.
The preparation method of the insulating adhesive film comprises the following steps:
and (3) uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a substrate, drying the substrate at 120 ℃ for 5min, and removing the substrate to obtain the insulating adhesive film with the thickness of 60 mu m.
Example 9
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that, in the insulating film, 12 parts by weight of benzocyclobutene containing fluorinated polyarylether structure and 18 parts by weight of benzocyclobutene containing fluorenyl structure are provided; other conditions were the same as in example 8.
Example 10
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that in the insulating film, 9 parts by weight of benzocyclobutene containing fluorinated polyarylether structure and 21 parts by weight of benzocyclobutene containing fluorenyl structure are provided; other conditions were the same as in example 8.
Example 11
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that, in the insulating film, 15 parts by weight of benzocyclobutene containing fluorinated polyarylether structure and 15 parts by weight of benzocyclobutene containing fluorenyl structure are provided; other conditions were the same as in example 8.
Example 12
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that in the insulating film, 7 parts by weight of benzocyclobutene containing fluorinated polyarylether structure and 23 parts by weight of benzocyclobutene containing fluorenyl structure are provided; other conditions were the same as in example 8.
Example 13
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that benzocyclobutene containing fluorinated polyarylether structure is not added in the insulating film, and the weight part of benzocyclobutene containing fluorenyl structure is 30 parts; other conditions were the same as in example 8.
Example 14
The embodiment provides an insulating film and a preparation method thereof, which are different from embodiment 8 only in that benzocyclobutene containing fluorenyl structure is not added in the insulating film, and the weight part of benzocyclobutene containing fluorinated polyarylether structure is 30 parts; other conditions were the same as in example 8.
Example 15
The present embodiment provides an insulating film and a method for preparing the same, which are different from embodiment 8 only in that no NH is added to the insulating film 2 MIL-125 (Ti), other conditions were the same as in example 8.
Comparative example 1
This comparative example provides an insulating film and a method for preparing the same, differing from example 1 only in that hexafluorocyclobutane benzocyclobutene and ZIF-8 are not added to the insulating film, and other conditions are the same as in example 1.
Comparative example 2
This comparative example provides an insulating film and a method for preparing the same, differing from example 2 only in that benzocyclobutene having a fluorenyl structure and ZIF-8 are not added thereto, and the other conditions are the same as example 2.
Comparative example 3
This comparative example provides an insulating film and a method for producing the same, differing from example 3 only in that hexafluorocyclobutane benzocyclobutene, benzocyclobutene having a fluorenyl structure, and ZIF-8 are not added thereto, and the other conditions are the same as in example 3.
The performance of the insulating film provided in the above examples and comparative examples was tested as follows:
dielectric constant and dielectric loss tangent: placing the insulating adhesive films provided in the above examples and comparative examples on a PET film, curing at 180 ℃ for 30min, and then peeling off the PET film, thereby obtaining a pre-cured insulating adhesive film; the pre-cured insulating film was cut into test pieces (3 pieces) of 2mm×80mm, and then the dielectric constant and dielectric loss tangent of each test piece were measured by a cavity resonance perturbation method under the conditions of a measurement frequency of 5.8GHz and a measurement temperature of 23 ℃, and the average value of the dielectric constants and dielectric loss tangents of the 3 test pieces was calculated as the dielectric constant and dielectric loss tangents obtained by the final test, using "HP8362B" of agilent technologies, inc.
The performance test results of the insulating films provided in the above examples and comparative examples are shown in table 1 below:
TABLE 1
As can be seen from the contents of Table 1, the insulating adhesive film prepared by designing the components of the insulating adhesive film and using MOFs material has excellent dielectric properties, the dielectric constant is 2.6-2.8, the dielectric loss tangent is 0.0016-0.0021, and the insulating adhesive film prepared by further using fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene and controlling the mass ratio of the fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene within a specific proportion range has excellent dielectric properties, the dielectric constant is 2.6-2.7, and the dielectric loss tangent is 0.0016-0.0018, so that the requirements of high-speed and high-integration development of electronic components can be met.
Compared with the embodiment 8, if the mass ratio of the fluorine-containing modified benzocyclobutene to the polycyclic modified benzocyclobutene is too large (embodiment 11), the compatibility among the components of the insulating adhesive film is poor, and the prepared insulating adhesive film is poor in dielectric property and mechanical property and is not friendly to the environment; if the mass ratio of fluorine-containing modified benzocyclobutene to polycyclic modified benzocyclobutene is too small (example 12), the dielectric loss of the prepared insulating film is large.
Compared with example 8, if the modified benzocyclobutene is only fluorine-containing modified benzocyclobutene (example 13) or if the modified benzocyclobutene is only polycyclic modified benzocyclobutene (example 14), the dielectric loss of the prepared insulating film is larger. Meanwhile, as shown in examples 1-2 and examples 4-5 of the present invention, if the modified benzocyclobutene is only fluorine-containing modified benzocyclobutene or if the modified benzocyclobutene is only polycyclic modified benzocyclobutene, the dielectric loss of the prepared insulating film is larger.
Compared with example 8, if MOFs material is not contained in the insulating film (example 15), the dielectric loss of the prepared insulating film is larger. Compared with examples 1-3, if the insulating film does not contain modified benzocyclobutene and MOFs (comparative examples 1-3), the dielectric constant and dielectric loss tangent of the prepared insulating film are both large.
In summary, through the design of the components of the insulating adhesive film, the invention further uses fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene, and controls the mass ratio of the fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene within a specific proportion range, and meanwhile, through the use of MOFs materials, the prepared insulating adhesive film has excellent dielectric properties, and can meet the requirements of development of high speed and high integration of electronic components.
The applicant states that the detailed process flow of the present invention is illustrated by the above examples, but the present invention is not limited to the above detailed process flow, i.e. it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (20)
1. The insulating adhesive film is characterized by comprising the following components in parts by weight:
20-50 parts of modified benzocyclobutene, 30-60 parts of free radical polymer, 120-150 parts of inorganic filling material, 3-5 parts of thermoplastic resin and 10-30 parts of thermosetting resin;
the modified benzocyclobutene is selected from fluorine-containing modified benzocyclobutene and polycyclic modified benzocyclobutene;
the mass ratio of the fluorine-containing modified benzocyclobutene to the polycyclic modified benzocyclobutene is 1 (1.5-2.4);
the fluorine-containing modified benzocyclobutene is selected from any one or a combination of at least two of hexafluorocyclobutane benzocyclobutene, octafluorocyclopentenyl benzocyclobutene, benzocyclobutene containing a bis (trifluoromethyl) benzene ring structure or benzocyclobutene containing a fluorinated polyarylether structure;
the polycyclic modified benzocyclobutene is selected from benzocyclobutene containing fluorenyl structure and/or benzocyclobutene containing adamantane;
the insulating adhesive film also comprises 1-3 parts of MOFs material.
2. The insulating film according to claim 1, wherein the radical polymer is selected from any one or a combination of at least two of a maleimide-containing radical polymer, a vinylphenyl radical polymer, a (meth) acrylic radical polymer, an allylic radical polymer, and a butadiene radical polymer.
3. The insulating film according to claim 1, wherein the radical polymer is selected from any one or a combination of at least two of a biphenyl aralkyl type maleimide resin, a liquid bismaleimide resin, a low polyphenylene ether-styrene resin, or a (meth) acrylic radical polymer.
4. The insulating film of claim 1, wherein the inorganic filler material is selected from any one or a combination of at least two of silica, alumina, glass, cordierite, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate, calcium zirconate, or zirconium phosphate.
5. The insulating film according to claim 1, wherein the thermoplastic resin is selected from any one or a combination of at least two of polyimide resin, polycarbonate resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyetheretherketone resin, polystyrene resin, polyester resin, or bisphenol ether resin.
6. The insulating film according to claim 1, wherein the thermosetting resin is selected from any one or a combination of at least two of epoxy resin, phenol resin, naphthol resin, benzoxazine resin, active ester resin, cyanate ester resin, carbodiimide resin, amine resin, or acid anhydride resin.
7. The insulating film according to claim 1, wherein the MOFs material is selected from any one or a combination of at least two of zeolite imidazole-based zinc-based MOFs, amino-functionalized titanium-based MOFs, or fluorine-functionalized zirconium-based MOFs.
8. The insulating film according to claim 1, further comprising 1 to 1.5 parts of a curing accelerator.
9. The insulating film according to claim 8, wherein the curing accelerator is selected from any one or a combination of at least two of a phosphorus-based curing accelerator, an amine-based curing accelerator, an imidazole-based curing accelerator, a guanidine-based curing accelerator and a metal-based curing accelerator.
10. The insulating film according to claim 1, further comprising 100 to 300 parts of an organic solvent.
11. The insulating film of claim 10, wherein the organic solvent is selected from any one or a combination of at least two of toluene, xylene, butanone, methyl ethyl ketone, cyclohexanone, ethyl acetate, or N, N-dimethylformamide.
12. The insulating film according to claim 1, wherein the thickness of the insulating film is 10 to 100 μm.
13. A method for preparing the insulating film according to any one of claims 1 to 12, comprising the steps of:
and uniformly mixing the components of the insulating adhesive film, coating the insulating adhesive film on a substrate, and drying to obtain the insulating adhesive film.
14. The method of claim 13, wherein the substrate has a thickness of 10 to 150 μm.
15. The method of claim 14, wherein the substrate has a thickness of 25 to 50 μm.
16. The method of claim 13, wherein the drying temperature is 80-130 ℃.
17. The method of claim 13, wherein the drying time is 3 to 10 minutes.
18. The method of claim 13, wherein the drying further comprises a post-treatment step.
19. The method of claim 18, wherein the post-treatment is removal of the substrate.
20. Use of an insulating film according to any one of claims 1-12 in printed circuit board and chip packaging.
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| CN113185940A (en) * | 2021-06-17 | 2021-07-30 | 广东中晨电子新材料有限公司 | Insulating glue film composition and application thereof in printed circuit board |
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| CN103086851B (en) * | 2013-01-31 | 2015-12-23 | 中国科学院上海有机化学研究所 | Containing simple thermosetting resin, the preparation method and application of fluorenes and benzocyclobutene structural unit |
| CN103665025B (en) * | 2013-12-31 | 2016-07-06 | 复旦大学 | The synthetic method of adamantyl benzocyclobutene monomer and polymer thereof |
| CN105152881B (en) * | 2015-06-23 | 2018-06-29 | 复旦大学 | Benzocyclobutene monomer, preparation method and application containing adamantane Yu trans-1,1,2,2,3,4-Hexafluorocyclobutane structure |
| JP6996808B2 (en) * | 2016-11-09 | 2022-01-17 | 花王株式会社 | Resin composition for forming an insulating film |
| CN113461484A (en) * | 2021-06-29 | 2021-10-01 | 天诺光电材料股份有限公司 | Fluorine-containing benzocyclobutene monomer and preparation method of resin thereof |
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