JP2010132614A - 新規なスルホニウムボレート錯体 - Google Patents
新規なスルホニウムボレート錯体 Download PDFInfo
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- JP2010132614A JP2010132614A JP2008310827A JP2008310827A JP2010132614A JP 2010132614 A JP2010132614 A JP 2010132614A JP 2008310827 A JP2008310827 A JP 2008310827A JP 2008310827 A JP2008310827 A JP 2008310827A JP 2010132614 A JP2010132614 A JP 2010132614A
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- sulfonium borate
- borate complex
- sulfonium
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- PSBPNWBGNOWCCU-UHFFFAOYSA-N OB(O)O.S.S.S Chemical compound OB(O)O.S.S.S PSBPNWBGNOWCCU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 229920000647 polyepoxide Polymers 0.000 claims description 42
- 239000003822 epoxy resin Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 31
- -1 o-methylbenzyl group Chemical group 0.000 claims description 17
- 239000003505 polymerization initiator Substances 0.000 claims description 17
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000011342 resin composition Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 12
- 230000001070 adhesive effect Effects 0.000 abstract description 12
- 125000002091 cationic group Chemical group 0.000 abstract description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 11
- 238000005260 corrosion Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000020169 heat generation Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000012663 cationic photopolymerization Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 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 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- NBADVBNRRHVIAO-UHFFFAOYSA-N phenylsulfanol Chemical compound OSC1=CC=CC=C1 NBADVBNRRHVIAO-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
式(2)のスルホニウムアンチモネート錯体に、式(3)のナトリウムボレート塩を反応させることにより式(1)のスルホニウムボレート錯体を得る製造方法を提供する。
式(2a)〜(2d)のスルホニウムアンチモネート錯体(合成方法は特開平10−245378号公報、特開2006−96742号公報参照)を酢酸エチルに溶解し、当該錯体の10質量%酢酸エチル溶液をそれぞれ調製した。これらとは別に式(3)のナトリウムボレート塩(合成方法は特開平10−310587号公報参照)の10質量%水溶液を調製した。
M+=289(スルホニウム残基)
M+=679(ボレート残基)
実測値が理論値に合致していた。
測定結果のIRチャートを図1に示す。実施例1の式(1A)のスルホニウムボレート錯体の結合のIR特性吸収は、図1のIRチャートにおいて観察された。
測定結果の1H−NMRチャートを図2Aに示し、対照となる溶媒のTHFの1H−NMRチャートを図2Bに示す。図2Aの1H−NMRチャートにおいて、以下のプロトンが帰属できた。
M+=281(スルホニウム残基)
M+=679(ボレート残基)
実測値 C;52.51 H;1.89
理論値 C;52.52 H;1.78
662(C−S)、776、980、1088、1276(Ar−F)、1300、1374、1464、1514、1583、1643、2881(C−H)、2981(C−H)、3107(O−H)
2.6(1H、(d))、3.3(3H、(a))、5.3(2H、(e))、6.9(2H、(c))、7.6(2H、(b))、7.2〜8.1(7H、(f),(g),(h),(i),(j),(k),(l))
M+=245(スルホニウム残基)
M+=679(ボレート残基)
実測値 C;50.39 H;1.77
理論値 C;50.60 H;1.80
662(C−S)、773、980、1088、1276(Ar−F)、1463、1514、1583、1644、2882(C−H)、2983(C−H)、3109(O−H)
2.3(3H、(j))、2.4(1H、(d))、3.3(3H、(a))、4.8(2H、(e))、7.0(2H、(c))、7.6(2H、(b))、7.0〜7.4(4H、(f),(g),(h),(i))
実施例1、比較例1〜3の各スルホニウムボレート錯体(1A)、(1a)、(1b)、(1c)、及び参考例1〜4としてそれらで使用したスルホニウムアンチモネート錯体(2a)〜(2d)のそれぞれについて、以下に説明するように、熱カチオン重合時の温度条件下でのフッ素イオン濃度を測定した。
錯体0.2gを純水10mLに投入し、100℃で10時間加温した後、上澄み液のフッ素イオン濃度を、イオンクロマトグラフィ分析(ダイオニクス社)により測定した。得られた結果を表1に示す。実用上、10ppm未満であることが望まれる。
表2の組成の成分を均一に混合することによりエポキシ樹脂組成物を調製した。更に、各エポキシ樹脂組成物について、以下に説明するように示差熱分析測定(DSC測定)を行い、また、耐電食性試験を行った。なお、使用した液状エポキシ樹脂は、ジャパンエポキシレジン社のエピコート828であり、シランカップリング剤は、γ−グリシドキシプロピルトリメトキシシラン(信越化学工業社)であり、充填材は、球状溶融シリカ(EB−6D、電気化学工業社)である。
エポキシ樹脂組成物について、熱分析装置(DSC 5100、セイコーインスツル社)を用いて昇温速度10℃/分で示差熱分析(発熱開始温度、ピーク温度、発熱量)を行った。得られた結果を表2に示す。
ガラス基板上にAl/Cr/ITO電極もしくはMo/ITO電極とを20μmギャップで櫛歯状に設けてなるガラス配線基板に、試験すべきエポキシ樹脂組成物を20μm厚となるように塗布し、200℃で10分間加熱して硬化させ、試験片を得た。得られた試験片を、85℃、85%RHの恒温槽中に入れ、電極間に30Vの電圧を印加した状態で12時間放置した。その後、電極に変色や欠陥、断線等が発生したか否かを、ガラス配線基板の表面及び裏面から光学顕微鏡を用いて観察し、以下の基準に従って評価した。得られた結果を表2に示す。
G:変色・欠陥・断線等が認められる場合
NG:変色・欠陥・断線等が認められない場合
Claims (9)
- R1がo−メチルベンジル基又は(1−ナフチル)メチル基である請求項1記載のスルホニウムボレート錯体。
- R2がメチル基である請求項1又は2記載のスルホニウムボレート錯体。
- nが1であり、R3O基がフェニル基の4位に結合している請求項1〜3のいずれかに記載のスルホニウムボレート錯体。
- R3がメトキシカルボニル基である請求項1〜4のいずれかに記載のスルホニウムボレート錯体。
- Xがフッ素原子である請求項1〜5のいずれかに記載のスルホニウムボレート錯体。
- エポキシ樹脂と熱カチオン重合開始剤とを含有するエポキシ樹脂組成物であって、該熱カチオン重合開始剤が、請求項1〜6のいずれかに記載のスルホニウムボレート錯体であることを特徴とするエポキシ樹脂組成物。
- 配線基板上に電子部品が請求項8記載のエポキシ樹脂組成物の熱硬化物により接合されていることを特徴とする接続構造体。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008310827A JP5444702B2 (ja) | 2008-12-05 | 2008-12-05 | 新規なスルホニウムボレート錯体 |
EP09830414.0A EP2354123B1 (en) | 2008-12-05 | 2009-12-02 | Novel sulfonium borate complex |
CN200980149017.0A CN102239144B (zh) | 2008-12-05 | 2009-12-02 | 新型硼酸锍络合物 |
PCT/JP2009/070222 WO2010064648A1 (ja) | 2008-12-05 | 2009-12-02 | 新規なスルホニウムボレート錯体 |
CN201610328587.8A CN105859763B (zh) | 2008-12-05 | 2009-12-02 | 新型硼酸锍络合物 |
US13/123,369 US8877878B2 (en) | 2008-12-05 | 2009-12-02 | Epoxy resin composition with sulfonium borate complex |
KR1020117012736A KR101689899B1 (ko) | 2008-12-05 | 2009-12-02 | 신규 술포늄보레이트 착체 |
CN201410523745.6A CN104277205B (zh) | 2008-12-05 | 2009-12-02 | 硼酸锍络合物 |
TW98141469A TWI434851B (zh) | 2008-12-05 | 2009-12-04 | Epoxy resin composition |
HK15106577.1A HK1206047A1 (en) | 2008-12-05 | 2015-07-10 | Novel sulfonium borate complex |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008310827A JP5444702B2 (ja) | 2008-12-05 | 2008-12-05 | 新規なスルホニウムボレート錯体 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2013269032A Division JP2014131997A (ja) | 2013-12-26 | 2013-12-26 | 新規なスルホニウムボレート錯体 |
Publications (2)
Publication Number | Publication Date |
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JP2010132614A true JP2010132614A (ja) | 2010-06-17 |
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JP2016108512A (ja) * | 2014-12-10 | 2016-06-20 | 日本化薬株式会社 | 有機el素子用樹脂組成物、面封止剤、及びこれを用いた有機el装置 |
JP2016117830A (ja) * | 2014-12-22 | 2016-06-30 | デクセリアルズ株式会社 | 化合物、熱硬化性樹脂組成物、及び熱硬化性シート |
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EP3260444A4 (en) * | 2015-02-16 | 2018-09-26 | San-Apro Ltd. | Sulfonium borate salt, acid generating agent and curable composition |
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CN104277205B (zh) | 2017-01-11 |
TW201026711A (en) | 2010-07-16 |
CN105859763A (zh) | 2016-08-17 |
CN102239144B (zh) | 2016-06-08 |
WO2010064648A1 (ja) | 2010-06-10 |
EP2354123A1 (en) | 2011-08-10 |
US20110192639A1 (en) | 2011-08-11 |
JP5444702B2 (ja) | 2014-03-19 |
CN105859763B (zh) | 2019-03-08 |
TWI434851B (zh) | 2014-04-21 |
CN102239144A (zh) | 2011-11-09 |
KR20110091864A (ko) | 2011-08-16 |
KR101689899B1 (ko) | 2016-12-26 |
CN104277205A (zh) | 2015-01-14 |
HK1206047A1 (en) | 2015-12-31 |
EP2354123A4 (en) | 2013-02-13 |
US8877878B2 (en) | 2014-11-04 |
EP2354123B1 (en) | 2015-02-25 |
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