JPWO2019130735A1 - ポリフェニレンエーテル樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 - Google Patents
ポリフェニレンエーテル樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 Download PDFInfo
- Publication number
- JPWO2019130735A1 JPWO2019130735A1 JP2019562777A JP2019562777A JPWO2019130735A1 JP WO2019130735 A1 JPWO2019130735 A1 JP WO2019130735A1 JP 2019562777 A JP2019562777 A JP 2019562777A JP 2019562777 A JP2019562777 A JP 2019562777A JP WO2019130735 A1 JPWO2019130735 A1 JP WO2019130735A1
- Authority
- JP
- Japan
- Prior art keywords
- polyphenylene ether
- resin composition
- group
- modified polyphenylene
- resin
- 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
- 229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 178
- 239000011342 resin composition Substances 0.000 title claims abstract description 129
- 229920005989 resin Polymers 0.000 title claims description 70
- 239000011347 resin Substances 0.000 title claims description 70
- 229910052751 metal Inorganic materials 0.000 title claims description 53
- 239000002184 metal Substances 0.000 title claims description 53
- 239000011888 foil Substances 0.000 title claims description 44
- -1 and prepreg using it Substances 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 54
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 20
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 239000000463 material Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005641 methacryl group Chemical group 0.000 claims description 3
- 239000000047 product Substances 0.000 description 40
- 239000010408 film Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000002585 base Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000002966 varnish Substances 0.000 description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 14
- 239000011889 copper foil Substances 0.000 description 14
- 239000003063 flame retardant Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000007423 decrease Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000003444 phase transfer catalyst Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 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 5
- 0 C*Oc(c(*)c1*)c(*)c(*)c1-c(c(*)c1*)c(*)c(*)c1OB* Chemical compound C*Oc(c(*)c1*)c(*)c(*)c1-c(c(*)c1*)c(*)c(*)c1OB* 0.000 description 5
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- CWJHMZONBMHMEI-UHFFFAOYSA-N 1-tert-butylperoxy-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1 CWJHMZONBMHMEI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 4
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000013039 cover film Substances 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000003044 adaptive effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008054 signal transmission Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- KCQLGLQQAZLWTF-FMIVXFBMSA-N (e)-3-[4-(2-phenylprop-2-enoyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(=O)C(=C)C1=CC=CC=C1 KCQLGLQQAZLWTF-FMIVXFBMSA-N 0.000 description 1
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
- ORYGKUIDIMIRNN-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenoxy)benzene Chemical compound BrC1=C(Br)C(Br)=CC(OC=2C(=C(Br)C(Br)=C(Br)C=2)Br)=C1Br ORYGKUIDIMIRNN-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- YZGJLGUCTISYPI-UHFFFAOYSA-N 1,3-bis(2-butylperoxypropan-2-yl)benzene Chemical compound CCCCOOC(C)(C)C1=CC=CC(C(C)(C)OOCCCC)=C1 YZGJLGUCTISYPI-UHFFFAOYSA-N 0.000 description 1
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- 101001134276 Homo sapiens S-methyl-5'-thioadenosine phosphorylase Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 102100022050 Protein canopy homolog 2 Human genes 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Inorganic materials [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
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Abstract
Description
(B)炭素−炭素不飽和二重結合を分子中に2個以上有する架橋型硬化剤とを含有するポリフェニレンエーテル樹脂組成物であって、
前記(A)変性ポリフェニレンエーテル化合物は、下記式(1)で示される(A−1)変性ポリフェニレンエーテル化合物と、下記式(2)で示される(A−2)変性ポリフェニレンエーテル化合物とを含むことを特徴とする。
(B)炭素−炭素不飽和二重結合を分子中に2個以上有する架橋型硬化剤とを含有するポリフェニレンエーテル樹脂組成物であって、
前記(A)変性ポリフェニレンエーテル化合物は、下記式(1)で示される(A−1)変性ポリフェニレンエーテル化合物と、下記式(2)で示される(A−2)変性ポリフェニレンエーテル化合物とを含むことを特徴とする。
(A−1)
・OPE−2St 1200:末端ビニルベンジル変性PPE(Mw:約1600、三菱瓦斯化学株式会社製)、上記式(9)で表される変性ポリフェニレンエーテル化合物である。
・変性PPE−1:2官能ビニルベンジル変性PPE(Mw:1900)
ここで、εは、吸光係数を示し、4700L/mol・cmである。また、OPLは、セル光路長であり、1cmである。
・TR2003:スチレン−ブタジエン−スチレン共重合体(Mw:10万、JSR株式会社製)
・BI−3000:水素化ポリブタジエン(Mn:3300、日本曹達株式会社製)
・DCP:ジシクロペンタジエン型メタクリレート(新中村化学工業株式会社製、分子量332、末端二重結合数2個)
・DVB810:ジビニルベンゼン(新日鐵住金株式会社製、分子量130、末端二重結合数2個
・B−1000:ポリブタジエンオリゴマー(日本曹達株式会社製、重量平均分子量Mw1100、末端二重結合数15個)
・FA−513M:ジシクロペンタニルメタクリレート(日立化成株式会社製、分子量220、末端二重結合数1個)
(反応開始剤)
・パーブチルP:1,3−ビス(ブチルパーオキシイソプロピル)ベンゼン(日本油脂株式会社製)
(無機充填材)
・SC2500−SXJ:フェニルアミノシラン表面処理球状シリカ(株式会社アドマテックス製)
[調製方法]
(樹脂ワニス)
まず、各成分を表1および2に記載の配合割合で、固形分濃度が60質量%となるように、トルエンに添加し、混合させた。その混合物を、60分間攪拌することによって、ワニス状の樹脂組成物(ワニス)が得られた。
各実施例および比較例の樹脂ワニスをガラスクロス(旭化成株式会社製、♯2116タイプ、Eガラス)に含浸させた後、100〜170℃で約3〜6分間加熱乾燥することによりプリプレグを得た。その際、プリプレグの重量に対する樹脂組成物の含有量(レジンコンテント)が約45質量%となるように調整した。
上記のプリプレグ1枚を、その両側に厚さ12μmの銅箔(古河電気工業株式会社製GT−MP)を配置して被圧体とし、真空条件下、温度200℃、圧力40kgf/cm2の条件で120分加熱・加圧して両面に銅箔が接着された、厚み0.1mmの銅張積層板−Iを得た。また、上記プリプレグ8枚を重ね、同様の方法で厚み0.8mmの銅張積層板−IIを得た。
(ガラス転移温度(Tg))
上記銅張積層板−Iの外層銅箔を全面エッチングし、得られたサンプルについて、セイコーインスツルメンツ株式会社製の粘弾性スペクトロメータ「DMS100」を用いて、Tgを測定した。このとき、引張モジュールで周波数を10Hzとして動的粘弾性測定(DMA)を行い、昇温速度5℃/分の条件で室温から280℃まで昇温した際のtanδが極大を示す温度をTgとした。
JIS C 6481(1996)の規格に準じて耐熱性を評価した。所定の大きさに切り出した上記銅張積層板−Iを280℃および290℃に設定した恒温槽に1時間放置した後、取り出した。そして熱処理された試験片を目視で観察し、290℃でフクレが発生しなかったときを◎、290℃でフクレが発生し280℃でフクレが発生しなかったときを○、280℃フクレが発生したときを×として評価した。
上記の銅箔積層板−IIの銅箔を除去したものを試験片とし、樹脂硬化物のガラス転移温度未満の温度における、Z軸方向の熱膨張係数を、JIS C 6481に従ってTMA法(Thermo−mechanical analysis)により測定した。測定には、TMA装置(エスアイアイ・ナノテクノロジー株式会社製「TMA6000」)を用い、30〜300℃の範囲で測定した。測定単位はppm/℃である。
銅箔張積層板−Iにおいて、絶縁層からの銅箔の引き剥がし強さをJIS C 6481に準拠して測定した。幅10mm、長さ100mmのパターンを形成し、引っ張り試験機により50mm/分の速度で引き剥がし、その時の引き剥がし強さ(ピール強度)を測定し、得られたピール強度を、銅箔密着強度とした。測定単位はkN/mである。
上記銅張積層板−IIから銅箔を除去した積層板を評価基板として用い、誘電正接(Df)を空洞共振器摂動法で測定した。具体的には、ネットワーク・アナライザ(アジレント・テクノロジー株式会社製のN5230A)を用い、10GHzにおける評価基板の誘電正接を測定した。
表1〜3に示す結果から明らかなように、本発明により、低誘電特性に加えて、高い耐熱性、高Tg(220℃以上)及び優れた密着性(ピール0.5kN/m以上)を兼ね備えたポリフェニレンエーテル樹脂組成物を提供できることが示された。さらにいずれの実施例においても、熱膨張率(CTE)は40℃/ppm以下と低めであった。
Claims (11)
- (A)炭素−炭素不飽和二重結合を有する置換基により末端変性された変性ポリフェニレンエーテル化合物と、
(B)炭素−炭素不飽和二重結合を分子中に2個以上有する架橋型硬化剤とを含有するポリフェニレンエーテル樹脂組成物であって、
前記(A)変性ポリフェニレンエーテル化合物は、下記式(1)で示される(A−1)変性ポリフェニレンエーテル化合物と、下記式(2)で示される(A−2)変性ポリフェニレンエーテル化合物とを含むことを特徴とする、ポリフェニレンエーテル樹脂組成物。
また、AおよびBはそれぞれ下記式(3)及び(4)で示される構造である:
- 前記(B)架橋型硬化剤が、トリアルケニルイソシアヌレート化合物、分子中にアクリル基を2個以上有する多官能アクリレート化合物、分子中にメタクリル基を2個以上有する多官能メタクリレート化合物、及び、分子中にビニル基を2個以上有する多官能ビニル化合物からなる群から選ばれる少なくとも1種であることを特徴とする、請求項1〜3いずれかに記載のポリフェニレンエーテル樹脂組成物。
- 前記(A)変性ポリフェニレンエーテル化合物と前記(B)架橋型硬化剤の合計量に対して、前記(A−1)変性ポリフェニレンエーテル化合物及び前記(A−2)変性ポリフェニレンエーテル化合物が、20〜95質量%の含有量で含まれていることを特徴とする、請求項1〜4のいずれかに記載のポリフェニレンエーテル樹脂組成物。
- 前記(A)変性ポリフェニレンエーテル化合物において、前記(A−1)変性ポリフェニレンエーテル化合物と前記(A−2)変性ポリフェニレンエーテル化合物の含有比が、質量比で(A−1):(A−2)=5:95〜95:5であることを特徴とする、請求項1〜5のいずれかに記載のポリフェニレンエーテル樹脂組成物。
- 請求項1〜6のいずれかに記載のポリフェニレンエーテル樹脂組成物又は前記樹脂組成物の半硬化物と繊維質基材とを有するプリプレグ。
- 請求項1〜6のいずれかに記載のポリフェニレンエーテル樹脂組成物又は前記樹脂組成物の半硬化物を含む樹脂層と、支持フィルムとを有する樹脂付きフィルム。
- 請求項1〜6のいずれかに記載のポリフェニレンエーテル樹脂組成物又は前記樹脂組成物の半硬化物を含む樹脂層と、金属箔とを有する、樹脂付き金属箔。
- 請求項1〜6のいずれかに記載のポリフェニレンエーテル樹脂組成物の硬化物又は前記請求項7に記載のプリプレグの硬化物を含む絶縁層と、金属箔とを有する、金属張積層板。
- 請求項1〜6のいずれかに記載のポリフェニレンエーテル樹脂組成物の硬化物又は前記請求項7に記載のプリプレグの硬化物を含む絶縁層と、配線とを有する、配線基板。
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