JP2010530463A - ベンゾキサジン含有組成物およびこれを使って製造される硬化性組成物 - Google Patents
ベンゾキサジン含有組成物およびこれを使って製造される硬化性組成物 Download PDFInfo
- Publication number
- JP2010530463A JP2010530463A JP2010513164A JP2010513164A JP2010530463A JP 2010530463 A JP2010530463 A JP 2010530463A JP 2010513164 A JP2010513164 A JP 2010513164A JP 2010513164 A JP2010513164 A JP 2010513164A JP 2010530463 A JP2010530463 A JP 2010530463A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- cyanatephenyl
- bis
- filler
- benzoxazine
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims description 31
- -1 benzoxazine compound Chemical class 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 238000010276 construction Methods 0.000 claims abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000004643 cyanate ester Substances 0.000 claims description 19
- 150000005130 benzoxazines Chemical class 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000945 filler Substances 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- FKAWETHEYBZGSR-UHFFFAOYSA-N 3-methylidenepyrrolidine-2,5-dione Chemical compound C=C1CC(=O)NC1=O FKAWETHEYBZGSR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 150000003553 thiiranes Chemical class 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004809 Teflon Substances 0.000 claims description 2
- 229920006362 Teflon® Polymers 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000002131 composite material Substances 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
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 229920003986 novolac Polymers 0.000 claims description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- 150000004684 trihydrates Chemical class 0.000 claims description 2
- 239000011231 conductive filler Substances 0.000 claims 2
- 238000000465 moulding Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 150000001913 cyanates Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 241001598984 Bromius obscurus Species 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 125000005014 aminoalkynyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- BZOMVTXCLKEFPP-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)butanedioic acid Chemical compound C1=CC=C2SC(C(C(O)=O)CC(=O)O)=NC2=C1 BZOMVTXCLKEFPP-UHFFFAOYSA-N 0.000 description 1
- KRDSXENYLDIORL-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylsulfanyl)butanedioic acid Chemical compound C1=CC=C2SC(SC(CC(=O)O)C(O)=O)=NC2=C1 KRDSXENYLDIORL-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 1
- 235000007911 Anacolosa luzoniensis Nutrition 0.000 description 1
- 244000217177 Anacolosa luzoniensis Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000234295 Musa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005025 alkynylaryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000006294 amino alkylene group Chemical group 0.000 description 1
- 125000005021 aminoalkenyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000005001 aminoaryl group Chemical group 0.000 description 1
- 125000005124 aminocycloalkyl group Chemical group 0.000 description 1
- 125000005214 aminoheteroaryl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000006270 aryl alkenylene group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005015 aryl alkynyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005019 carboxyalkenyl group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000005026 carboxyaryl group Chemical group 0.000 description 1
- 125000005352 carboxycycloalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
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- 125000005000 thioaryl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
- H01L21/563—Encapsulation of active face of flip-chip device, e.g. underfilling or underencapsulation of flip-chip, encapsulation preform on chip or mounting substrate
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
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Abstract
【化】
[構造中、Rは、C1−40アルキル、C2−40アルケニル(これら各々は、任意に、1個以上のO、N、S、C=O、COO、およびNHC=Oによって置換されているか、または割込まれている)、およびC6−20アリールから選択されるものであり、mは、0−4であり、ならびにR1−R5は、独立して、C1−40アルキル、C2−40アルケニル(これら各々は、任意に、1個以上のO、N、S、C=O、COOH、およびNHC=Oによって置換されているか、または割込まれている)、およびC6−20アリールから選択され、R1−R5の少なくとも1個は存在する]によって包含される単官能ベンゾキサジン化合物を含む、50℃以下の温度で液状形態である組成物が提供される。
Description
本発明は、構造:
ベンゾキサジンは公知である。エポキシ樹脂とベンゾキサジンとのブレンドも公知である。例えば、米国特許第4,607,091号(Schreiber)、同5、021,484号(Schreiber)、同5,200,452号(Schreiber)、および同5,445,911号(Schreiber)各公報を参照されたし。これらのブレンドは、電子産業において潜在的に有用であるように思われる。なぜなら、エポキシ樹脂がベンゾキサジンの溶融粘度を低下し、加工できる粘度を維持しながらも高い充填量でフィラーを使うことを可能にするからである。しかしながら、エポキシ樹脂は、ベンゾキサジンが重合する温度を高くすることがよくあり、望ましくない。
(a)典型的には、約6から約500個までの範囲の炭素原子を有するヒドロカルビルまたは置換ヒドロカルビル種であって、このヒドロカルビル種は、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、アリール、アルキルアリール、アリールアルキル、アリールアルケニル、アルケニルアリール、アリールアルキニル、またはアルキニルアリールから選択されるが、しかしながら、Xが2つ以上の異なった種の組合わせを含む場合にだけ、Xはアリールであってもよく、
(b)典型的には、約6から約500個までの範囲の炭素原子を有するヒドロカルビレンまたは置換ヒドロカルビレン種であって、このヒドロカルビレン種は、アルキレン、アルケニレン、アルキニレン、シクロアルキレン、シクロアルケニレン、アリーレン、アルキルアリーレン、アリールアルキレン、アリールアルケニレン、アルケニルアリーレン、アリールアルキニレン、またはアルキニルアリーレンから選択され、
(c)典型的には、約6から約500個までの範囲の炭素原子を有する複素環または置換複素環種、
(d)ポリシロキサン、および
(e)ポリシロキサン−ポリウレタンブロック・コポリマー、
を含む一価基または多価基、ならびに、
共有結合、−O−、−S−、−NR−、−NR−C(O)−、−NR−C(O)−O−、−NR−C(O)−NR−、−S−C(O)−、−S−C(O)−O−、−S−C(O)−NR−、−O−S(O)2−、−O−S(O)2−O−、−O−S(O)2−NR−、−O−S(O)−、−O−S(O)−O−、−O−S(O)−NR−、−O−NR−C(O)−、−O−NR−C(O)−O−、−O−NR−C(O)−NR−、−NR−O−C(O)−、−NR−O−C(O)−O−、−NR−O−C(O)−NR−、−O−NR−C(S)−、−O−NR−C(S)−O−、−O−NR−C(S)−NR−、−NR−O−C(S)−、−NR−O−C(S)−O−、−NR−O−C(S)−NR−、−O−C(S)−、−O−C(S)−O−、−O−C(S)−NR−、−NR−C(S)−、−NR−C(S)−O−、−NR−C(S)−NR−、−S−S(O)2−、−S−S(O)2−O−、−S−S(O)2−NR−、−NR−O−S(O)−、−NR−O−S(O)−O−、−NR−O−S(O)−NR−、−NR−O−S(O)2−、−NR−O−S(O)2−O−、−NR−O−S(O)2−NR−、−O−NR−S(O)−、−O−NR−S(O)−O−、−O−NR−S(O)−NR−、−O−NR−S(O)2−O−、−O−NR−S(O)2−NR−、−O−NR−S(O)2、−O−P(O)R2−、−S−P(O)R2−、または−NR−P(O)R2−、(ここで各々のRは、独立して、水素、アルキルまたは置換アルキルである)から選択されるリンカーを有する上記の1つ以上の組合わせ化合物、
から選択することができる。
本発明に従って液状形態であるベンゾキサジンは、以下のように調製することができる。
本発明の範囲内の組成物を、ベンゾキサジンをシアネートエステルおよびシリカに混合しながら添加することによって、室温で8,000cPsの粘度を有する系を生じさせて調製した。この粘度は、90℃の温度で200cPsに低下し、この組成物は、175℃の温度、2時間で硬化することができる。このような組成物を、各々、重量基準で45.5%のベンゾキサジン#4、4.5%のシアネートエステル(L−10)および50.0%のシリカ(FL−1950)から調製した。
本実施例では、ベンゾキサジン#18を1重量%の濃度のジカルボン酸触媒(IRGACOR LD252)と併用して試料Aを作った。2つの追加試料、試料BおよびCを試料Aから調製し、50%および60%のシリカでそれぞれ充填した。温度165℃で4時間硬化させ、試料A、B、およびCのCTE値が48、25および22であることを認めた。
本実施例では、ベンゾキサジン#12を、1重量%の濃度のIRGACOR LD252と併用して試料Dを作った。温度165℃で4時間硬化させ、試料DのCTE値が47であることを認めた。
Claims (24)
- 構造:
- 室温で液状形態である、請求項1に記載の組成物。
- 室温で10,000cPs未満の粘度を有する、請求項1に記載の組成物。
- 室温で150cPs未満の粘度を有する、請求項1に記載の組成物。
- さらに、シアネートエステル、エポキシ、エピスルフィド、マレイミド、イタコンイミド、ナジミド、オキサゾリン、アリルアミド、アクリレート、メタクリレート、ビニルエーテル、ビニルエステル、およびこれらの組合わせから選択される官能基を有する化合物を含む、請求項1に記載の組成物。
- 前記化合物が、シアネートエステル官能基を有し、および前記シアネートエステルに対する前記ベンゾキサジンの比が2:1から25:1の範囲にある、請求項5に記載の組成物。
- さらに、フィラーを含む、請求項5に記載の組成物。
- 前記フィラーが、無機フィラーである、請求項7に記載の組成物。
- 前記無機フィラーが、シリカである、請求項8に記載の組成物。
- 前記フィラーが、導電性フィラーである、請求項7に記載の組成物。
- 前記フィラーが、非導電性フィラーである、請求項7に記載の組成物。
- 硬化された場合、フィラー濃度50重量%で15から35の範囲の熱膨張係数を有する、請求項5に記載の組成物。
- 175℃の温度に2時間、曝すことによって硬化された場合、直線的測定によって0.1%未満の容積収縮を有する、請求項5に記載の組成物。
- アンダーフィル、カプセルの材料、成形複合物またはダイ接着剤として使用するために硬化性組成物において有用である、請求項1に記載の組成物。
- さらに、多官能ベンゾキサジンを含む、請求項1に記載の組成物。
- 前記多官能ベンゾキサジンが、液状形態である、請求項12に記載の組成物。
- 前記シアネートエステル化合物が、1,3−ジシアネートベンゼン、1,4−ジシアネートベンゼン、1,3,5−トリシアネートベンゼン、1,3−、1,4−、1,6−、1,8−、2,6−または2,7−ジシアネートナフタレン、1,3,6−トリシアネートナフタレン、4,4’−ジシアネート−ビフェニル、ビス(4−シアネートフェニル)メタンおよび3,3’,5,5’−テトラメチル、ビス(4−シアネートフェニル)メタン、2,2−ビス(3,5−ジクロロ−4−シアネートフェニル)プロパン、2,2−ビス(3,5−ジブロモ−4−ジシアネートフェニル)プロパン、ビス(4−シアネートフェニル)エーテル、ビス(4−シアネートフェニル)スルフィド、2,2−ビス(4−シアネートフェニル)プロパン、トリス(4−シアネートフェニル)ホスファイト、トリス(4−シアネートフェニル)ホスフェート、ビス(3−クロロ−4−シアネートフェニル)メタン、シアネート化ノボラック、1,3−ビス[4−シアネートフェニル−1−(メチルエチリデン)]ベンゼンおよびシアネート化、ビスフェノール末端ポリカーボネートまたは他の熱可塑性オリゴマーである、請求項5に記載の組成物。
- 前記フィラーが、アルミナ、窒化アルミニウム、シリカ、窒化ケイ素、窒化ホウ素、およびアルミナ3水和物からなる群より選択されるものである、請求項7に記載の組成物。
- 前記フィラーが、テフロン(登録商標)、(メタ)アクリル粒子、PDMS粒子、ポリオレフィン粒子およびスチレンからなる群より選択されるものである、請求項7に記載の組成物。
- 3、9および11番の2官能ベンゾキサジンの組合わせを含む、請求項1に記載の組成物。
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JP2017526757A (ja) * | 2014-06-19 | 2017-09-14 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | フルオロポリマー組成物 |
JP2018500442A (ja) * | 2014-12-29 | 2018-01-11 | サイテック インダストリーズ インコーポレイテッド | ベンゾオキサジン及びベンゾオキサジンを含有する組成物 |
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JP2018500442A (ja) * | 2014-12-29 | 2018-01-11 | サイテック インダストリーズ インコーポレイテッド | ベンゾオキサジン及びベンゾオキサジンを含有する組成物 |
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WO2008156443A1 (en) | 2008-12-24 |
JP5514719B2 (ja) | 2014-06-04 |
US20100140542A1 (en) | 2010-06-10 |
KR20100038372A (ko) | 2010-04-14 |
EP2167478A4 (en) | 2011-07-27 |
CN101743233A (zh) | 2010-06-16 |
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