JP2010237575A - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JP2010237575A JP2010237575A JP2009087371A JP2009087371A JP2010237575A JP 2010237575 A JP2010237575 A JP 2010237575A JP 2009087371 A JP2009087371 A JP 2009087371A JP 2009087371 A JP2009087371 A JP 2009087371A JP 2010237575 A JP2010237575 A JP 2010237575A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- 229920005989 resin Polymers 0.000 claims abstract description 151
- 239000011347 resin Substances 0.000 claims abstract description 151
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 57
- 239000003822 epoxy resin Substances 0.000 claims abstract description 53
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 103
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 239000000758 substrate Substances 0.000 claims description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 28
- 150000008065 acid anhydrides Chemical class 0.000 claims description 24
- 229920001187 thermosetting polymer Polymers 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 23
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 150000004292 cyclic ethers Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 12
- 239000003086 colorant Substances 0.000 claims description 11
- 150000007519 polyprotic acids Polymers 0.000 claims description 11
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- NCAVPEPBIJTYSO-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.OCCCCOC(=O)C=C NCAVPEPBIJTYSO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
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- 239000004065 semiconductor Substances 0.000 abstract description 9
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- 239000002994 raw material Substances 0.000 abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- -1 cyclic carbonate compound Chemical class 0.000 description 111
- 239000000049 pigment Substances 0.000 description 91
- 239000010408 film Substances 0.000 description 57
- 239000000203 mixture Substances 0.000 description 39
- 239000000126 substance Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 35
- 238000000576 coating method Methods 0.000 description 33
- 239000011248 coating agent Substances 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- 229910000679 solder Inorganic materials 0.000 description 24
- 239000004593 Epoxy Substances 0.000 description 23
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 16
- 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 16
- 239000012948 isocyanate Substances 0.000 description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000002981 blocking agent Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
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- 229920001228 polyisocyanate Polymers 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000013329 compounding Methods 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 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 9
- 239000012535 impurity Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 7
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 7
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 6
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 6
- 238000007650 screen-printing Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 6
- 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 5
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 5
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- 125000002252 acyl group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
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- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
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- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
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Abstract
【解決手段】硬化性樹脂組成物において、エポキシ樹脂を出発原料としないカルボキシル基含有樹脂と、カルボキシル基含有樹脂に1分子中に環状エーテル基とエチレン性不飽和基を併せ持つ化合物を反応させて得られるカルボキシル基含有感光性樹脂と、光重合開始剤と、を含有する。
【選択図】なし
Description
さらに、これらカルボキシル基含有感光性樹脂(A)(B)の合計の酸価が、30〜150mgKOH/gの範囲内にあることが望ましい。カルボキシル基含有感光性樹脂(A)(B)の配合後の酸価が30mgKOH/gよりも低い場合には、アルカリ水溶液に対する溶解性が低下し、形成した塗膜の現像が困難になる。一方、150mgKOH/gよりも高くなると、現像液による露光部の溶解が進むために、必要以上にラインが痩せたり、露光部と未露光部の区別なく現像液で溶解剥離してしまい、正常なレジストパターンの描画が困難となる場合がある。より好ましくは40〜110mgKOH/gである。
下記一般式(VI)で表される化合物
本実施形態において、感度を向上するために、連鎖移動剤として公知のNフェニルグリシン類、フェノキシ酢酸類、チオフェノキシ酢酸類、メルカプトチアゾール等を用いることができる。具体例を挙げると、例えば、メルカプト琥珀酸、メルカプト酢酸、メルカプトプロピオン酸、メチオニン、システイン、チオサリチル酸及びその誘導体等のカルボキシル基を有する連鎖移動剤;メルカプトエタノール、メルカプトプロパノール、メルカプトブタノール、メルカプトプロパンジオール、メルカプトブタンジオール、ヒドロキシベンゼンチオール及びその誘導体等の水酸基を有する連鎖移動剤;1−ブタンチオール、ブチル−3−メルカプトプロピオネート、メチル−3−メルカプトプロピオネート、2,2−(エチレンジオキシ)ジエタンチオール、エタンチオール、4−メチルベンゼンチオール、ドデシルメルカプタン、プロパンチオール、ブタンチオール、ペンタンチオール、1−オクタンチオール、シクロペンタンチオール、シクロヘキサンチオール、チオグリセロール、4,4−チオビスベンゼンチオール等である。
また、活性エネルギー線照射により、光硬化して、カルボキシル基含有樹脂を、アルカリ水溶液に不溶化させる、又は不溶化を助けるために、希釈剤を用いることができる。このような希釈剤としては、エチレングリコール、メトキシテトラエチレングリコール、ポリエチレングリコール、プロピレングリコールなどのグリコールのジアクリレート類;ヘキサンジオール、トリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール、トリス−ヒドロキシエチルイソシアヌレートなどの多価アルコール又はこれらのエチレオキサイド付加物もしくはプロピレンオキサイド付加物などの多価アクリレート類;フェノキシアクリレート、ビスフェノールAジアクリレート、及びこれらのフェノール類のエチレンオキサイド付加物もしくはプロピレンオキサイド付加物などの多価アクリレート類;グリセリンジグリシジルエーテル、グリセリントリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、トリグリシジルイソシアヌレートなどのグリシジルエーテルの多価アクリレート類;及びメラミンアクリレート、及び/又は上記アクリレートに対応する各メタクリレート類などが挙げられる。
耐熱性を付与するために、熱硬化性成分を加えることができる。本実施形態において用いられる熱硬化成分としては、メラミン樹脂、ベンゾグアナミン樹脂などのアミン樹脂、ビスマレイミド、ベンゾオキサジン化合物、オキサゾリン化合物、カルボジイミド樹脂、ブロックイソシアネート化合物、シクロカーボネート化合物、多官能エポキシ化合物、多官能オキセタン化合物、エピスルフィド樹脂、メラミン誘導体などの公知の熱硬化性樹脂を使用することができる。特に好ましいのは、分子中に2個以上の環状エーテル基及び/又は環状チオエーテル基(以下、環状(チオ)エーテル基と略す)である。
このような分子中に2つ以上の環状(チオ)エーテル基を有する熱硬化性成分を使用する場合、熱硬化触媒を含有することが好ましい。そのような熱硬化触媒としては、例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等のイミダゾール誘導体;ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等のアミン化合物、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド等のヒドラジン化合物;トリフェニルホスフィン等のリン化合物など、また市販されているものとしては、例えば四国化成工業社製の2MZ−A、2MZ−OK、2PHZ、2P4BHZ、2P4MHZ(いずれもイミダゾール系化合物の商品名)、サンアプロ社製のU−CAT3503N、U−CAT3502T(いずれもジメチルアミンのブロックイソシアネート化合物の商品名)、DBU、DBN、U−CATSA102、U−CAT5002(いずれも二環式アミジン化合物及びその塩)などが挙げられる。特に、これらに限られるものではなく、エポキシ樹脂やオキセタン化合物の熱硬化触媒、もしくはエポキシ基及び/又はオキセタニル基とカルボキシル基の反応を促進するものであればよい。これらは、単独で又は2種以上を混合して使用してもかまわない。また、グアナミン、アセトグアナミン、ベンゾグアナミン、メラミン、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等のS−トリアジン誘導体を用いることもできる。これら密着性付与剤としても機能する化合物を、熱硬化触媒と併用することがより好ましい。
さらに、本実施形態の硬化性樹脂組成物において、感光性樹脂組成物の硬化性及び得られる硬化膜の強靭性を向上させるために、1分子内に2個以上のイソシアネート基、又はブロック化イソシアネート基を有する化合物を加えることができる。このような1分子内に2個以上のイソシアネート基、又はブロック化イソシアネート基を有する化合物は、1分子内に2個以上のイソシアネート基を有する化合物、すなわちポリイソシアネート化合物、又は1分子内に2個以上のブロック化イソシアネート基を有する化合物、すなわちブロックイソシアネート化合物などが挙げられる。
さらに、本実施形態の硬化性樹脂組成物には、水酸基とイソシアネート基との硬化を促進させるために、ウレタン化触媒を加えることができる。ウレタン化触媒としては、錫系触媒、金属塩化物、金属アセチルアセトネート塩、金属硫酸塩、アミン化合物、又は/及びアミン塩より群から選択される1種以上のウレタン化触媒を使用することが好ましい。
さらに、熱硬化成分としてメラミン誘導体、ベンゾグアナミン誘導体などが挙げられる。例えばメチロールメラミン化合物、メチロールベンゾグアナミン化合物、メチロールグリコールウリル化合物およびメチロール尿素化合物などがある。さらに、アルコキシメチル化メラミン化合物、アルコキシメチル化ベンゾグアナミン化合物、アルコキシメチル化グリコールウリル化合物およびアルコキシメチル化尿素化合物は、それぞれのメチロールメラミン化合物、メチロールベンゾグアナミン化合物、メチロールグリコールウリル化合物およびメチロール尿素化合物のメチロール基をアルコキシメチル基に変換することにより得られる。このアルコキシメチル基の種類については特に限定されるものではなく、例えばメトキシメチル基、エトキシメチル基、プロポキシメチル基、ブトキシメチル基等とすることができる。特に人体や環境に優しいホルマリン濃度が0.2%以下のメラミン誘導体が好ましい。
さらに、本実施形態の硬化性組成物において、層間の密着性、又は基材との密着性を向上させるために、密着付与剤を用いることができる。具体的に例を挙げると、例えば、ベンゾイミダゾール、ベンゾオキサゾール、ベンゾチアゾール、2−メルカプトベンゾイミダゾール、2−メルカプトベンゾオキサゾール、2−メルカプトベンゾチアゾール(商品名:川口化学工業株式会社製 アクセルM)、3−モルホリノメチル−1−フェニル−トリアゾール−2−チオン、5−アミノ−3−モルホリノメチル−チアゾール−2−チオン、2−メルカプト−5−メチルチオ−チアジアゾール、トリアゾール、テトラゾール、ベンゾトリアゾール、カルボキシベンゾトリアゾール、アミノ基含有ベンゾトリアゾール、シランカップリング剤などである。
さらに、着色剤を配合することができる。着色剤としては、赤、青、緑、黄などの慣用公知の着色剤を使用することができ、顔料、染料、色素のいずれでもよい。但し、環境負荷低減並びに人体への影響の観点から、ハロゲンを含有しないことが好ましい。
青色着色剤としては、フタロシアニン系、アントラキノン系を挙げることができる。このうち、顔料系ではピグメント(Pigment)に分類されている化合物、具体的には、以下のようなカラーインデックス(C.I.;(The Society of Dyers and Colourists)発行)番号が付されている、Pigment Blue 15、Pigment Blue 15:1、Pigment Blue 15:2、Pigment Blue 15:3、Pigment Blue 15:4、Pigment Blue 15:6、Pigment Blue 16、Pigment Blue 60等を使用することができる。
緑色着色剤としては、同様にフタロシアニン系、アントラキノン系、ペリレン系が挙げられる。具体的にはPigment Green 7、Pigment Green 36、Solvent Green 3、Solvent Green 5、Solvent Green 20、Solvent Green 28等を使用することができる。これら以外にも、金属置換もしくは無置換のフタロシアニン化合物も使用することができる。
黄色着色剤としては、アントラキノン系、イソインドリノン系、縮合アゾ系、ベンズイミダゾロン系、モノアゾ系、ジスアゾ系等が挙げられる。具体的には、以下のものを使用することができる。
赤色着色剤としては、モノアゾ系、ジスアゾ系、モノアゾレーキ系、ベンズイミダゾロン系、ペリレン系、ジケトピロロピロール系、縮合アゾ系、アントラキノン系、キナクリドン系などが挙げられる。具体的には以下のものを使用することができる。
さらに、その塗膜の物理的強度等を上げるために、必要に応じて、フィラーを配合することができる。このようなフィラーとしては、公知の無機又は有機フィラーが使用できるが、特に硫酸バリウム、球状シリカおよびタルクが好適に用いられる。さらに、白色の外観や難燃性を得るために酸化チタンや金属酸化物、水酸化アルミなどの金属水酸化物を体質顔料フィラーとしても使用することができる。また、1個以上のエチレン性不飽和基を有する化合物や前記多官能エポキシ樹脂(D−1)にナノシリカを分散したHanse−Chemie社製のNANOCRYL(商品名) XP 0396、XP 0596、XP 0733、XP 0746、XP 0765、XP 0768、XP 0953、XP 0954、XP 1045(何れも製品グレード名)や、Hanse−Chemie社製のNANOPOX(商品名) XP 0516、XP 0525、XP 0314(何れも製品グレード名)も使用することができる。これらフィラーは、単独で又は2種以上配合することができる。
さらに、指触乾燥性の改善、ハンドリング性の改善などを目的として、バインダーポリマーを使用することができる。例えば、ポリエステル系ポリマー、ポリウレタン系ポリマー、ポリエステルウレタン系ポリマー、ポリアミド系ポリマー、ポリエステルアミド系ポリマー、アクリル系ポリマー、セルロース系ポリマー、ポリ乳酸系ポリマー、フェノキシ系ポリマーなどを用いることができる。これらのバインダーポリマーは、単独で又は2種類以上の混合物として使用することができる。
さらに、柔軟性の付与、硬化物の脆さを改善することなどを目的として、エラストマーを使用することができる。例えば、ポリエステル系エラストマー、ポリウレタン系エラストマー、ポリエステルウレタン系エラストマー、ポリアミド系エラストマー、ポリエステルアミド系エラストマー、アクリル系エラストマー、オレフィン系エラストマーを用いることができる。また、種々の骨格を有するエポキシ樹脂の一部又は全部のエポキシ基を、両末端カルボン酸変性型ブタジエン−アクリロニトリルゴムで変性した樹脂なども使用できる。さらには、エポキシ含有ポリブタジエン系エラストマー、アクリル含有ポリブタジエン系エラストマー、水酸基含有ポリブタジエン系エラストマー、水酸基含有イソプレン系エラストマーなども使用することができる。これらのエラストマーは、単独で又は2種類以上の混合物として使用することができる。
さらに、カルボキシル基含有感光性樹脂(A)の合成や組成物の調整のため、又は基板やキャリアフィルムに塗布するための粘度調整のため、有機溶剤を使用することができる。
高分子材料の多くは、一度酸化が始まると、次々と連鎖的に酸化劣化が起き、高分子素材の機能低下をもたらすことから、本実施形態の硬化性樹脂組成物において、酸化を防ぐために(1)発生したラジカルを無効化するようなラジカル補足剤または/及び(2)発生した過酸化物を無害な物質に分解し、新たなラジカルが発生しないようにする過酸化物分解剤などの酸化防止剤を添加することができる。
高分子材料は光を吸収し、それにより分解・劣化を起こすことから、本実施形態の硬化性樹脂組成物は、紫外線に対する安定化を図るために、酸化防止剤の他に、紫外線吸収剤を使用することができる。
温度計、窒素導入装置兼アルキレンオキシド導入装置及び撹拌装置を備えたオートクレーブに、ノボラック型クレゾール樹脂(昭和高分子(株)製、商品名「ショーノールC RG951」、OH当量:119.4)119.4g 、水酸化カリウム1.19g及びトルエン119.4gを仕込み、撹拌しつつ系内を窒素置換し、加熱昇温した。次に、プロピレンオキシド63.8gを徐々に滴下し、125〜132℃、0〜4.8kg/cm2で16時間反応させた。
ジエチレングリコールモノエチルエーテルアセテート685gにオルソクレゾールノボラック型エポキシ樹脂〔大日本インキ化学工業株式会社製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6〕1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。
ジエチレングリコールモノエチルエーテルアセテート700gに、オルソクレゾールノボラック型エポキシ樹脂〔大日本インキ化学工業株式会社製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6〕1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。
攪拌機、温度計、環流冷却管、滴下ロート及び窒素導入管を備えた2リットルのセパラブルフラスコに、ジエレングリコールモノエチルエーテルアセテート197gにオルソクレゾールノボラック型エポキシ樹脂「EPICLON N−695」214g(グリシジル基数(芳香環総数):1.0モル)、アクリル酸72g(1.0モル)、及びハイドロキノン0.29gを仕込み、100℃に加熱攪拌し、均一溶解した。次いで、トリフェニルホスフィン0.86g を仕込み、110℃に加熱して2時間反応後、トリフェニルホスフィン0.23gを追加し、120℃に昇温してさらに12時間反応を行った。
ジエチレングリコールモノエチルエーテルアセテート600gに、オルソクレゾールノボラック型エポキシ樹脂〔大日本インキ化学工業株式会社製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6〕1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。
エポキシ当量800、軟化点79℃のビスフェノールF型固型エポキシ樹脂400部を、エピクロルヒドリン925部とジメチルスルホキシド462.5部を溶解させた後、攪拌下70℃で98.5%NaOH 81.2部を100分かけて添加した。添加後さらに70℃で3時間反応を行なった。
(イルガキャア907: チバ・スペシャリティー・ケミカルズ社製)
*2 2,4-ジエチルチオキサントン(KAYACURE DETX-S:日本化薬社製)
*3 2-(アセチルオキシイミノメチル)チオキサンテン-9-オン
*4 エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-, 1-(0-アセチルオキシム) (イルガキュア OXE 02:チバスペシャリティーケミカルズ社製)
*5 ジペンタエリスリトールペンタアクリレート(DPHA: 日本化薬社製)
*6 変性ノボラック型エポキシ樹脂(EPICLON N-865:DIC社製)
*7 ビキシレノール型エポキシ樹脂(YX-4000:ジャパンエポキシレジン(株)製)
*8 メチル化メラミン樹脂((株)三和ケミカル製)
*9 ブロックイソシアネート(旭化成ケミカルズ社製)
*10 C.I.Pigment Blue 15:3
*11 C.I.Pigment Yellow147
*12 2-メルカプトベンゾチアゾール
*13 酸化防止剤(チバ・スペシャリティー・ケミカルズ社製)
*14 B-30 (堺化学(株)製)
*15 ハイドロタルサイト(協和化学工業(株)製)
*16 ジエチレングリコールモノエチルエーテールアセテート
このようにして得られた実施例1〜11および比較例1〜4について、以下のように評価を行った。
〈最適露光量〉
前記実施例及び比較例の硬化性樹脂組成物を、銅厚35μmの回路パターン基板をバフロール研磨後、水洗し、乾燥してからスクリーン印刷法により全面に塗布し、80℃の熱風循環式乾燥炉で60分間乾燥させる。乾燥後、高圧水銀灯搭載の露光装置、及び最大波長355nmの半導体レーザーを搭載した直接描画装置を用いてステップタブレット(KodakNo2)を介して露光し、現像(30℃、0.2MPa、1質量%炭酸ナトリウム水溶液)を60秒で行った際残存するステップタブレットのパターンが7段の時を最適露光量とした。
前記実施例及び比較例の硬化性樹脂組成物を、銅ベタ基板上にスクリーン印刷法により乾燥後、約25μmになるように塗布し、80℃の熱風循環式乾燥炉で30分間乾燥させた。乾燥後、1質量%炭酸ナトリウム水溶液によって現像を行い、乾燥塗膜が除去されるまでの時間をストップウォッチにより計測した。
各実施例及び比較例の組成物を、パターン形成された銅箔基板上にスクリーン印刷で全面塗布し、80℃で乾燥し20分から80分まで10分おきに基板を取り出し室温まで放冷する。この基板に30℃の1質量%炭酸ナトリウム水溶液をスプレー圧0.2MPaの条件で60秒間現像を行い、残渣が残らない最大許容乾燥時間を最大現像ライフとした。
それぞれの光硬化性樹脂組成物をパターン形成された銅箔基板上にスクリーン印刷で全面塗布し、80℃の熱風循環式乾燥炉で30分間乾燥させ、室温まで放冷した。この基板にPET製ネガフィルムを当て、ORC社製(HMW−GW20)で1分間減圧条件下で圧着させ、その後、ネガフィルムを剥がしたときのフィルムの張り付き状態を評価した。
実施例及び比較例の各組成物を、パターン形成された銅箔基板上にスクリーン印刷で全面塗布し、80℃で30分乾燥し、室温まで放冷する。この基板に高圧水銀灯を搭載した露光装置を用いて、最適露光量でソルダーレジストパターンを露光した。そして、30℃の1質量%炭酸ナトリウム水溶液をスプレー圧0.2MPa/cm2の条件で90秒間現像を行い、レジストパターンを得た。この基板を、UVコンベア炉にて積算露光量1000mJ/cm2 の条件で紫外線照射した後、150℃で60分加熱して硬化した。得られたプリント基板(評価基板)に対して、以下のように特性を評価した。
評価基板を、10vol%H2SO4水溶液に室温で30分間浸漬し、染み込みや塗膜の溶け出しを目視にて確認し、さらにテープビールによる剥がれを確認した。
△:ほんの僅か変化しているもの
×:塗膜に膨れあるいは膨潤脱落があるもの
〈耐アルカリ性〉
評価基板を、10vol%NaOH水溶液に室温で30分間浸漬し、染み込みや塗膜の溶け出しを目視にて確認し、さらにテープビールによる剥がれを確認した。
△:ほんの僅か変化しているもの
×:塗膜に膨れあるいは膨潤脱落があるもの
〈はんだ耐熱性〉
ロジン系フラックスを塗布した評価基板を、予め260℃に設定したはんだ槽に浸漬し、変性アルコールでフラックスを洗浄した後、目視によるレジスト層の膨れ・剥がれについて評価した。判定基準は以下のとおりである。
市販品の無電解ニッケルめっき浴及び無電解金めっき浴を用いて、ニッケル5μm、金0.05μmの条件でめっきを行い、テープピーリングにより、レジスト層の剥がれの有無やめっきのしみ込みの有無を評価した後、テープピーリングによりレジスト層の剥がれの有無を評価した。判定基準は以下のとおりである。
ソルダーレジスト硬化塗膜を形成した評価基板を、PCT装置(エスペック株式会社製 HAST SYSTEM TPC−412MD)を用いて、121℃、飽和、0.2MPaの条件で168時間処理し、塗膜の状態を評価した。判定基準は以下の通りである。
△:若干の膨れ、剥がれ、変色、溶出があるもの
×:膨れ、剥がれ、変色、溶出が多く見られるもの
〈冷熱衝撃耐性〉
□抜き、○抜きパターンを形成したソルダーレジスト硬化塗膜を有する評価基板を作製した。得られた評価基板を冷熱衝撃試験器(エタック株式会社製)で−55℃/30分〜150℃/30分を1サイクルとして1000サイクルの耐性試験を行った。試験後、処理後の硬化膜を目視により観察し、クラックの発生状況を下記の基準にて判断した。
△ : クラック発生率30〜50%
× : クラック発生率50%以上
〈HAST特性〉
クシ型電極(ライン/スペース=50ミクロン/50ミクロン)が形成されたBT基板に、ソルダーレジスト硬化塗膜を形成し、評価基板を作成した。この評価基板を、130℃、湿度85%の雰囲気下の高温高湿槽に入れ、電圧5Vを荷電し、168時間、槽内HAST試験を行った。168時間経過時の槽内絶縁抵抗値を下記の判断基準に従い評価した。
表1にて調整した実施例1−5及び比較例1、2をメチルエチルケトンにて希釈し、PETフィルム上に塗布して、80℃で30分乾燥し、厚さ20μmの感光性樹脂組成物層を形成した。さらにその上に、カバーフィルムを貼り合わせてドライフィルムを作製し、それぞれを実施例12−16、及び比較例5、6とした。
Claims (10)
- エポキシ樹脂を出発原料としないカルボキシル基含有樹脂(A)と、
カルボキシル基含有樹脂に1分子中に環状エーテル基とエチレン性不飽和基を併せ持つ化合物を反応させて得られるカルボキシル基含有感光性樹脂(B)と、
光重合開始剤と、
を含有することを特徴とする硬化性樹脂組成物。 - 前記カルボキシル基含有樹脂(A)は、1分子中に2個以上のフェノール性水酸基を有する化合物とアルキレンオキシド又はシクロカーボネート化合物とを反応させて得られる反応生成物に、不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られることを特徴とする請求項1に記載の硬化性樹脂組成物。
- 前記カルボキシル基含有感光性樹脂(B)において、前記1分子中に環状エーテル基とエチレン性不飽和基を併せ持つ化合物が、グリシジル(メタ)アクリレート、4−ヒドロキシブチルアクリレートグリシジルエーテル、あるいは3、4-エポキシシクロヘキシルメチルメタアクリレートあることを特徴とする請求項1又は請求項2に記載の硬化性樹脂組成物。
- 前記カルボキシル基含有樹脂(A)において、カルボキシル基含有樹脂が感光性であることを特徴とする請求項1から請求項3のいずれか1項に記載の硬化性樹脂組成物。
- さらに、熱硬化性成分を含有することを特徴とする請求項1から請求項4のいずれか1項に記載の硬化性樹脂組成物。
- さらに、着色剤を含有することを特徴とする請求項1から請求項5のいずれか1項に記載の硬化性樹脂組成物。
- 請求項1から請求項6のいずれか1項に記載の硬化性樹脂組成物を基材に塗布し、活性エネルギー線照射及び/又は加熱により硬化させて得られることを特徴とする硬化物。
- 請求項1から請求項6のいずれか1項に記載の硬化性樹脂組成物を、キャリアフィルムに塗布・乾燥して得られることを特徴とするドライフィルム。
- 請求項8に記載のドライフィルムを基材に貼り付け、活性エネルギー線照射及び/又は加熱により硬化させて得られることを特徴とする硬化物。
- 請求項8又は請求項9に記載の硬化物を具備することを特徴とするプリント配線板。
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KR101394173B1 (ko) * | 2012-01-20 | 2014-05-14 | 주식회사 케이씨씨 | 강도, 경도 및 밀착성이 우수한 감광성 하이브리드 수지, 및 이것을 함유하는 알칼리현상이 가능한 경화성 조성물 및 그 경화물 |
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