CN101303528A - Photocuring resin composition, dry film, and print circuit board - Google Patents
Photocuring resin composition, dry film, and print circuit board Download PDFInfo
- Publication number
- CN101303528A CN101303528A CNA2008100818575A CN200810081857A CN101303528A CN 101303528 A CN101303528 A CN 101303528A CN A2008100818575 A CNA2008100818575 A CN A2008100818575A CN 200810081857 A CN200810081857 A CN 200810081857A CN 101303528 A CN101303528 A CN 101303528A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- photocurable resin
- composition according
- carboxylic acid
- compound
- 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
- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 238000000016 photochemical curing Methods 0.000 title abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 41
- 239000011347 resin Substances 0.000 claims abstract description 41
- 229910000679 solder Inorganic materials 0.000 claims abstract description 41
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052802 copper Inorganic materials 0.000 claims abstract description 32
- 239000010949 copper Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 11
- 239000001060 yellow colorant Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000000038 blue colorant Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 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 claims description 6
- 150000004056 anthraquinones Chemical class 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 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 claims description 5
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 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 claims description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 abstract description 5
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000001062 red colorant Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 description 43
- 229920000647 polyepoxide Polymers 0.000 description 43
- 239000000049 pigment Substances 0.000 description 39
- -1 phthalocyanine compound Chemical class 0.000 description 34
- 239000000126 substance Substances 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000576 coating method Methods 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- 239000003086 colorant Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 229920002120 photoresistant polymer Polymers 0.000 description 10
- 239000005864 Sulphur Substances 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000013007 heat curing Methods 0.000 description 9
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 8
- 229920003319 Araldite® Polymers 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 8
- 239000002966 varnish Substances 0.000 description 8
- 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 7
- 239000002585 base Substances 0.000 description 7
- 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 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000008595 infiltration Effects 0.000 description 5
- 238000001764 infiltration Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 125000003566 oxetanyl group Chemical group 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000001029 thermal curing Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003553 thiiranes Chemical group 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 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 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- 150000001896 cresols Chemical class 0.000 description 2
- 150000004294 cyclic thioethers Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
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- VDOIZUWXKARYAM-UHFFFAOYSA-N 1,3,5-triazinane-2,4,6-trione;1,3,5-triazine Chemical compound C1=NC=NC=N1.O=C1NC(=O)NC(=O)N1 VDOIZUWXKARYAM-UHFFFAOYSA-N 0.000 description 1
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- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229950004616 tribromoethanol Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention provides a coloring photo-curing resin composition and condensate thereof, dry film and printing circuit board, which can form a solder resist layer with excellent concealment of color change caused by oxidation of copper circuit. The photo-curing resin composition can develop through alkali water solution and contains carboxylic acid resin (A), photopolymerization initiator (B), compound (C) with more than two olefinic unsaturated radicals and red colorant (D).
Description
Technical field
The present invention relates to not contain the painted Photocurable resin composition of halogen-containing phthalocyanine green.Say in further detail, the disguised excellent solder mask that can provide the oxidation that utilizes copper circuit to cause variable color, the painted Photocurable resin composition that does not contain halogen-containing phthalocyanine green are provided.
Background technology
Usually, solder resist forms in order to protect copper circuit.Its role is to, can't see by the variable color of the heat of copper circuit, variable color that moisture causes, electricity, such aspects such as flaw, pollution on the copper circuit.
Solder resist is applied on the glass epoxide base material that is formed with copper circuit, forms image by exposure, forms this overlay film pattern by development, heat curing.Owing to be formed with copper circuit on base material, therefore, under the situation to its coating solder resist or lamination solder resist, its resist film thickness is thick on the base material, thin on copper circuit, thinner in the part at the edge of copper circuit.
In the different situation of the thickness of such solder resist, be difficult to from covering copper circuit in appearance.Therefore, in solder resist, cooperate colorant usually, thicken, be difficult for variable color of seeing copper circuit etc. by making its concentration.
From reducing the viewpoint of carrying capacity of environment, replace chlorination phthalocyanine green in the nearest solder resist as the colorant of existing green, the solder resist that uses the yellow colorants do not have the phthalocyanine blue of halogen atom and not have a halogen atom to form green is popularized (for example, with reference to patent documentation 1).
In addition, for from clearly being halogen-free in appearance, can use phthalocyanine blue separately, also can be used as blue solder resist and use.
Yet, from the following description, can be clear and definite: compare with the green that forms by phthalocyanine green, the green solder resist that forms by solder resist, blue colorant and the yellow colorants of blueness disguised weak, less than the function of giving full play to as the colorant of the bad phenomenon that is difficult to see outward appearance.
Promptly, present solder resist is to form image, finally implement heat curing and handle by photocuring.The treatment temperature of this moment is generally 150 ℃ and descended about 30～60 minutes, but according to substrate manufacturer, temperature, time are fixing.Its result: particularly under the long situation of treatment temperature height, processing time, there is the problem of the variable color that the oxidation of the copper circuit on can not hidden substrate causes in the solder resist of disguised bad blueness.Further confirm by the inventor, even use the green solder resist of halogen-free blue colorant and yellow colorants to have this problem too, a little less than phthalocyanine green disguise.
In addition, implementing on the substrate under the situation of marking ink, after the curing of solder resist, further typographic(al) mark and heat curing, so the variable color of copper circuit is quickened, apparent problem becomes more deep.
The further warpage of the substrate that produces when revising the heat curing of solder resist exists substrate integral body is exerted pressure and the situation of heat, and this moment, the variable color of same copper circuit was quickened.
In the variable color of such copper circuit, the worst phenomenon is: though on identical copper circuit also only at the state of the edge of circuit (part of resist attenuation) variable color.Under such situation, when inspection, installation base plate, owing to do not calibrate with checking data, bad even non-defective unit also becomes.On the other hand, though see on the variable color copper circuit equably can with the situation of other parts identifications under do not produce such unfavorable condition.
Such condition of poor is former to be in the news, and particularly used replacing phthalocyanine green under the situation (colorant non-halogen) of the colorants such as phthalocyanine blue with halogen atom and became remarkable.
Patent documentation 1: TOHKEMY 2000-7974 communique (claims, prior art)
Summary of the invention
Invent problem to be solved
Therefore, the object of the present invention is to provide painted Photocurable resin composition, it can form the disguised excellent solder mask that the oxidation by copper circuit is caused variable color etc.
The method that is used to deal with problems
The inventor etc. are through further investigation, found that: by using the painted Photocurable resin composition of red stain at least as colorant, can remove the concealed the problems referred to above in the existing solder resist that uses halogen-free colorant, and then can be by using halogen-free red stain, realize the content of halogen in the reduction solder mask and do not make disguised deterioration, thereby finished the present invention.
That is, the present invention is a Photocurable resin composition, and it can develop and contain compound (C) and the red stain (D) that has 2 above ethylenically unsaturated groups in carboxy resin (A), Photoepolymerizationinitiater initiater (B), the molecule by alkaline aqueous solution.
In the form of above-mentioned Photocurable resin composition of the present invention, except that red stain (D), can contain blue colorant (E1) (for example, phthalocyanine blue) and/or yellow colorants (E2), its tone can be blueness, green, purple or orange.
In addition, in the form of Photocurable resin composition of the present invention, red stain (D) is any one the red stain in the not halogen-containing and azo group.
In addition, in the form of Photocurable resin composition of the present invention, it further contains Thermocurable composition (F).
In addition, in the form of Photocurable resin composition of the present invention, it is applied on the copper and is used.
In addition, other forms of the present invention are the photo-curable dry film, and it is applied to above-mentioned Photocurable resin composition on the carrier film, and are dry and obtain.
In addition, other forms of the present invention be above-mentioned Photocurable resin composition blueness, green, purple or orange solidfied material.
In addition, other forms of the present invention be above-mentioned dry film blueness, green, purple or orange solidfied material.
In addition, other forms of the present invention are for to be formed with the printed circuit board (PCB) that has the solder mask that is formed by above-mentioned solidfied material on the substrate of copper circuit.
The invention effect
By the present invention, can provide disguised excellent blueness, green, purple or the orange painted solder mask of the variable color that the oxidation by copper circuit is caused.Particularly as blue solder resist replace having disguised problem general blue solder resist and effectively.In addition, the halogen gas generation extremely low, when filming burning of the content of halogen by the resulting solder mask of the present invention significantly reduces.
Description of drawings
Fig. 1 is the figure of expression Mang Saier hue circle.
Embodiment
Below, the present invention will be described in detail.
As described above, Photocurable resin composition of the present invention, it is characterized in that, replace existing halogen-containing phthalocyanine green and use red stain (D) at least as colorant, in the form of Photocurable resin composition, except that red stain (D), also contain blue colorant (E1) and/or yellow colorants (E2), its tone can be blueness, green, purple or orange.
Therefore, at first, describe for colorant of the present invention.In the present invention, colorant can use known colorant commonly used, can be any one in pigment, dyestuff, the pigment.But reduce and, preferably do not contain halogen the viewpoint of the influence of human body from carrying capacity of environment.
As red stain (D), monoazo system, bisdiazo system, azo lake system, benzimidazolone Xi, perylene system, pyrrolopyrrole diketone system, condensation azo system, anthraquinone system, quinacridone etc. are arranged, specifically, can list the chromaticity index (C.I. that has as following; The distribution of The Society of Dyers and Colourists company) compound of sequence number.
-monoazo system: paratonere 1,2,3,4,5,6,8,9,12,14,15,16,17,21,22,23,31,32,112,114,146,147,151,170,184,187,188,193,210,245,253,258,266,267,268,269;
-bisdiazo system: pigment red 37,38,41;
-monoazo color lake: pigment red 4 8:1,48:2,48:3,48:4,49:1,49:2,50:1,52:1,52:2,53:1,53:2,57:1,58:4,63:1,63:2,64:1,68;
-benzimidazolone system: paratonere 171,175,176,185,208;
-perylenes system: solvent of red 135,179; Pigment red 123,149,166,178,179,190,194,224;
-pyrrolopyrrole diketone system: paratonere 254,255,264,270,272;
-condensation azo system: paratonere 220,144,166,214,220,221,242;
-anthraquinone system: paratonere 168; 177,216; Solvent red 149,150,52,207;
-quinacridone: pigment red 122,202,206,207,209.
Be not particularly limited, but be fit to the red stain that use does not contain azo group from the viewpoint of security innocuousness.
As blue colorant (E1), phthalocyanine system, anthraquinone system are arranged, pigment system is the compound that is classified as pigment (Pigment), specifically, can list the compound of the chromaticity index sequence number that has as following.
-pigment system: pigment blue 15,15:1,15:2,15:3,15:4,15:6,16,60;
-dyestuff system: solvent blue 35,63,68,70,83,87,94,97,122,136,67,70.
Except above-mentioned, can also use metal to replace or do not have the phthalocyanine compound of replacement.
As yellow colorants (E2), monoazo system, bisdiazo system, condensation azo system, benzimidazolone system, isoindolinone system, anthraquinone system etc. are arranged, specifically, can list the compound of the chromaticity index sequence number that has as following.
-anthraquinone system: solvent yellow 16 3, pigment yellow 24,108,193,147,199,202;
-isoindolinone system: pigment yellow 110,109,139,179,185;
-condensation azo system: pigment yellow 93,94,95,128,155,166,180;
-benzimidazolone system: pigment Yellow 12 0,151,154,156,175,181;
-monoazo system: pigment yellow 1,2,3,4,5,6,9,10,12,61,62,62:1,65,73,74,75,97,100,104,105,111,116,167,168,169,182,183;
-bisdiazo system: pigment Yellow 12,13,14,16,17,55,63,81,83,87,126,127,152,170,172,174,176,188,198.
Be not particularly limited, from the viewpoint of security innocuousness, suitable use does not contain the yellow colorants of azo group.
Among the present invention, the fit rate of red stain and blue colorant and/or yellow colorants can be by the desired tone of the solder mask that resulting Photocurable resin composition, its curing overlay film form, specifically by deciding presenting blueness, green, purple or orange sufficient ratio.
Among the present invention, the blueness that Photocurable resin composition, its curing overlay film of the present invention was, green, purple and orange being meant: have under the with the naked eye observed situation of observer it is identified as the tone of blueness, green, purple and orange degree.Specifically, be meant by the method for JISZ8721 defined measure the expression Photocurable resin composition with and during the outward appearance tone of curing overlay film, (juridical person Japan color research institute edits new 2 Munsell system day of Essential colour watch series true qualities and grinds the distribution of cause Co., Ltd. at the Mang Saier hue circle; With reference to Fig. 1) on, belong to hue range from 5B G to not enough 3P (blueness), from 9Y to not enough 5BG (green), from 3P to not enough 7RP (purple), from 9R to not enough 7YR (orange), and be preferably have chroma 1 above less than 16, lightness is 1 above less than 9, more preferably chroma 2 above less thaies 15, lightness are 2 above less thaies 9.
Concrete cooperation ratio is subjected to the kind of employed colorant, other the influence of kind of adjuvant etc., therefore must not make sweeping generalizations, mass ratio is red stain (D): blue colorant (E1): yellow colorants (E2)=1: 0～50: 0～50 but usually.In addition, painted fully in order to carry out, preferably cooperate as the total amount of red stain (D), blue colorant (E1) and yellow colorants (E2) with the ratio of 0.05～3.0 quality % of total composition.
Among the present invention, except above-mentioned colorant, can also add the purple that is used to adjust tone, orange, dark brown, colorants such as black, specifically, can list pigment violet 19,23,29,32,36,38,42, solvent violet 13,36, C.I. pigment orange 1, C.I. pigment orange 5, C.I. pigment orange 13, C.I. pigment orange 14, C.I. pigment orange 16, C.I. pigment orange 17, C.I. pigment orange 24, C.I. pigment orange 34, C.I. pigment orange 36, C.I. pigment orange 38, C.I. pigment orange 40, C.I. pigment orange 43, C.I. pigment orange 46, C.I. pigment orange 49, C.I. pigment orange 51, C.I. pigment orange 61, C.I. pigment orange 63, C.I. pigment orange 64, C.I. pigment orange 71, C.I. pigment orange 73, C.I. bistre 23, C.I. bistre 25; C.I. pigment black 1, C.I. pigment black 7 etc.
Then, describe for containing carboxylic acid resin (A).
Contain carboxylic acid resin (A) as Photocurable resin composition of the present invention comprises, can use the resin compound known commonly used that contains carboxylic acid in the molecule.Further from photo-curable, anti-development aspect, what more preferably have ethylenical unsaturated double bonds in the molecule contains carboxylic acid photoresist (A ').
Specifically, can list the following resin of enumerating.
(1) in addition the compound with unsaturated double-bond obtains by unsaturated carboxylic acids such as copolymerization (methyl) acrylic acid and more than a kind contain the carboxyl acid copolymer resin,
(2) by (methyl) glycidyl acrylate, (methyl) acrylic acid 3,4-epoxycyclohexyl methyl esters etc. has compound, (methyl) acryloyl chloride of epoxy radicals and unsaturated double-bond etc., ethylenically unsaturated group is added to unsaturated carboxylic acids such as (methyl) acrylic acid as side chain and more than a kind in addition the multipolymer of compound with unsaturated double-bond, obtain thus contain the carboxylic acid photoresist,
(3) make (methyl) glycidyl acrylate, (methyl) acrylic acid 3,4-epoxycyclohexyl methyl esters etc. has the multipolymer of the compound of epoxy radicals and unsaturated double-bond and the compound with unsaturated double-bond in addition, with the reaction of unsaturated carboxylic acid such as (methyl) acrylic acid, secondary hydroxyl and the multi-anhydride that is generated reacted and the photonasty that obtains contain the carboxyl acid copolymer resin,
(4) make multipolymer that maleic anhydride etc. has the acid anhydrides of unsaturated double-bond and in addition a compound with unsaturated double-bond and (methyl) acrylic acid 2-hydroxyl ethyl ester etc. have the compound reaction of hydroxyl and unsaturated double-bond and obtain contain the carboxylic acid photoresist,
(5) make the reaction of multi-group epoxy compound and unsaturated monocarboxylic, the hydroxyl that generated and saturated or unsaturated multi-anhydride are reacted and obtain contain the carboxylic acid photoresist,
(6) make the reaction of hydroxyl polymer-containing such as polyvinyl alcohol derivative and saturated or unsaturated multi-anhydride after, the compound that has epoxy radicals and unsaturated double-bond in the carboxylic acid that generated and a part reacted and the photoresist of the hydroxyl that obtains and carboxylic acid,
(7) make have in multi-group epoxy compound, unsaturated monocarboxylic and a part at least 1 alcoholic extract hydroxyl group and with the alcoholic extract hydroxyl group of epoxy reaction beyond the reaction product of compound of 1 reactive group, obtain with saturated or unsaturated multi-anhydride reaction contain the carboxylic acid photoresist,
(8) make the reaction of the polyfunctional group oxetane compound that has at least two oxetanes rings in a part and unsaturated monocarboxylic, and primary hydroxyl in the modification oxetane resin of gained is reacted with saturated or unsaturated multi-anhydride and obtain contain the carboxylic acid photoresist and
(9) make polyfunctional epoxy resin and unsaturated monocarboxylic the reaction after, obtain containing the carboxylic acid resin with the multi-anhydride reaction, again this is contained the compound reaction that has 1 oxirane ring and 1 above ethylenically unsaturated group in carboxylic acid resin and the molecule and obtain contain carboxylic acid photoresist etc., but be not limited to these.
In the middle of these illustrations preferably above-mentioned (2), (5), (7) contain the carboxylic acid resin, particularly from photo-curable, cured coating film characteristic aspect, preferably above-mentioned (9) contain the carboxylic acid photoresist.
In addition, in this manual, (methyl) acrylate is meant the term of general name acrylate, methacrylate and their potpourri, and other similarly show too.
The carboxylic acid resin of containing as described above (A) has a large amount of free carboxyls at the side chain of trunk polymer, thereby can develop by alkaline aqueous solution.
In addition, the above-mentioned carboxylic acid resin's of containing (A) acid number is preferably the scope of 40～200mgKOH/g, the scope of 45～120mgKOH/g more preferably.When containing carboxylic acid resin's acid number deficiency 40mgKOH/g, alkali develops difficult, on the other hand, when surpassing 200mgKOH/g, developer solution causes the dissolving aggravation of exposure portion, thereby line is thinner than required, according to circumstances, exposure portion and unexposed are developed the liquid dissolving as broad as longly and peel off, and are difficult to describe normal corrosion-resisting pattern, so not preferred.
In addition, the above-mentioned weight-average molecular weight that contains carboxylic acid resin (A) is generally 2000～150000, more preferably 5000～100000 scope because of the resin matrix difference.During weight-average molecular weight less than 2000, the dry to touch degradation, the moisture-proof variation of filming after the exposure, generation film minimizing when developing, resolution is very poor.On the other hand, weight-average molecular weight surpasses at 150000 o'clock, the remarkable variation of development, storage-stable variation.
The fit rate that contains carboxylic acid resin (A) like this is preferably 20～60 quality %, 30～50 quality % more preferably in whole compositions.Under the situation about lacking than above-mentioned scope, coating strength reduces, so not preferred.On the other hand, under the situation of Duoing than above-mentioned scope, viscosity uprises, or reduction such as coating, so not preferred.
Then, describe for Photoepolymerizationinitiater initiater (B).
As Photoepolymerizationinitiater initiater (B), for example can list, acetophenone, 2,2-dimethoxy-2-phenyl acetophenone, 2,2-diethoxy-2-phenyl acetophenone, to dimethylamino propiophenone, dichloroacetophenone, trichloroacetophenone, to tert-butyl group trichloroacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butanone-1, N, acetophenones such as N-dimethylamino benzoylformaldoxime; Benzophenone, methyldiphenyl ketone, 2-chlorobenzophenone, 4,4 '-dichloro benzophenone, 4,4 '-two dimethylamino benzophenone, 4,4 '-two diethylamino benzophenone, Michler's keton, 4-benzoyl-4 '-benzophenones such as methyldiphenyl thioether; Benzil; Benzoin ethers such as benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether, benzoin isobutyl ether; Ketal classes such as acetophenone dimethyl ketal, benzyl dimethyl ketal; Thioxanthones, 2-clopenthixal ketone, 2,4-dimethyl thioxanthones, 2,4-diethyl thioxanthone, 2, thioxanthene ketones such as 4-diisopropyl thioxanthones; 2-methylanthraquinone, 2-EAQ, 2-tert-butyl group anthraquinone, 1-chloroanthraquinone, 2-amino anthraquinones, 2, anthraquinone classes such as 3-diphenyl anthraquinone; Organic peroxide such as benzoyl peroxide, cumene peroxide; 2,4, mercaptan compounds such as 5-triarylimidazoles dipolymer, hibon, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole; 2,4,6-three-s-triazine, 2,2, organic halogen compounds such as 2-ethobrom, trisbromomethyl benzene sulfone; 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, two (2,4, the 6-trimethylbenzoyl) phenyl phosphine oxide etc.These compounds can use separately, in addition, and use more than 2 kinds also capable of being combined.
In addition; above-mentioned Photoepolymerizationinitiater initiater (B) can with being used in combination more than a kind or 2 kinds of following light sensitizer; as N; N-dimethylamino benzoic acid ethyl ester; N; N-dimethylamino benzoic acid isopentyl ester; amyl group-4-dimethylaminobenzoic acid ester; triethylamine; tertiary amines such as triethanolamine; two (η 5-cyclopentadienyl groups)-two (2; 6-two fluoro-3-(1H-pyrroles-1-yl) phenyl) two luxuriant titanium classes such as titanium; 2-(acetoxyl group iminomethyl) thioxanthene-9-one; 1-[4-(thiophenyl)-2-(0-benzoyl oxime)] } and 1, the 2-acetyl caproyl; 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-oxime ester classes such as 1-(O-acetyl oxime) ethyl ketone.
The preferred compositions of aforementioned lights polymerization initiator (B) is that (4-morpholinyl phenyl)-the 1-butanone (for example for 2-benzyl-2-dimethylamino-1-; Ciba SpecialtyChemicals K.K. system; IRGACURE 369:IRGACURE is a registered trademark) and two (η 5-cyclopentadienyl group)-two (2; 6-two fluoro-3-(1H-pyrrole radicals-1-yl) phenyl) titanium (for example; Ciba S pecialty Chemical s K.K. system; IRGACURE 784) combination; 2; 4; 6-trimethylbenzoyl diphenyl phosphine oxide (for example; BASF makes LucirinTPO) and 2-(acetoxyl group iminomethyl) thioxanthene-9-one (for example; Ciba S pecialty Chemicals K.K. system; C GI-325) combination; or 2; 4; 6-trimethylbenzoyl diphenyl phosphine oxide (for example; BASF makes LucirinTPO) and two (2; 4; the 6-trimethylbenzoyl)-phenyl phosphine oxide (for example, Ciba Specialty Chemicals K.K. system; IRGACURE 819) etc. combination.
In addition, the OK range of the use amount of above-mentioned such Photoepolymerizationinitiater initiater (B) is preferably 1～30 mass parts, the ratio of 5～25 mass parts more preferably for contain carboxylic acid resin (A) with respect to 100 mass parts.Under the few situation of the above-mentioned scope of cooperation ratio of Photoepolymerizationinitiater initiater, the photo-curable of resultant composition is bad.On the other hand, under the situation of Duoing than above-mentioned scope, the bad characteristic of resulting cured coating film, in addition, the storage stability of composition is bad, so not preferred.
Then, describe for the compound that has 2 above ethylenically unsaturated groups in the molecule (C).
The compound (C) that has 2 above ethylenically unsaturated groups in the used molecule of Photocurable resin composition of the present invention is as described below: the photocuring by the active energy beam irradiation does not dissolve the aforementioned carboxylic acid resin of containing (A) or helps to make the aforementioned carboxylic acid resin of containing (A) not dissolve in alkaline aqueous solution in alkaline aqueous solution.As such compound, can list the diacrylate class of glycol such as ethylene glycol, methoxyl TEG, polyglycol, propylene glycol; The multicomponent methacrylate class of polyvalent alcohols such as hexanediol, trimethylolpropane, pentaerythrite, dipentaerythritol, tris(2-hydroxy ethyl)isocyanurate or these ethylene oxide adduct or propylene oxide adduct etc.; The multicomponent methacrylate class of the ethylene oxide adduct of acrylic acid benzene oxygen ester, bisphenol a diacrylate and these phenols or propylene oxide adduct etc.; The multicomponent methacrylate class of glycidol ethers such as glycerin diglycidyl ether, T 55, trihydroxymethylpropanyltri diglycidyl ether, triglycidyl group isocyanuric acid ester; And the melamine acrylate and/or with corresponding each methyl acrylic ester of aforesaid propylene acid esters etc.
Further, can enumerate the Epocryl of polyfunctional epoxy resins such as making the cresols phenolic resin varnish type epoxy resin and acrylic acid reaction; Further make epoxy polyurethane acrylate compounds that half urethane compound (half urethanecompound) reaction of diisocyanate such as crylic acid hydroxy ester such as the hydroxyl of this Epocryl and pentaerythritol triacrylate and isophorone diisocyanate obtains etc.Such epoxy acrylate is that resin can improve photo-curable and dry to touch can not reduce.
The fit rate that has the compound (C) of 2 above ethylenically unsaturated groups in such molecule is 5～100 mass parts, the ratio of 1～70 mass parts more preferably with respect to the aforementioned carboxylic acid resin of containing of 100 mass parts (A).Under the situation of aforementioned use level less than 5 mass parts, photo-curable reduces, and develops by the postradiation alkali of active energy beam, is difficult to form pattern, so not preferred.On the other hand, surpass under the situation of 100 mass parts, to the dissolubility of alkaline aqueous solution reduce, filming becomes fragile, so not preferred.
Then, describe for Thermocurable composition (F).
In order to give thermotolerance, can in Photocurable resin composition of the present invention, add Thermocurable composition (F).Be preferably the Thermocurable composition (F) of the ring-type ether that in molecule, has more than 2 and/or cyclic thioether base (below, abbreviate ring-type (sulphur) ether as) especially.
The Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in such molecule is for having 3 more than 2 in molecule, the ring-type ether of 4 or 5 yuan of rings, or in the cyclic thioether base any, or has a compound of 2 kinds of groups, for example can list: the compound that in molecule, has at least 2 above epoxy radicals, be multi-group epoxy compound (F-1), the compound that in molecule, has at least 2 above oxetanyls, be polyfunctional group oxetane compound (F-2), in molecule, have the compound of the thioether group more than 2, it is episulfide resin (F-3) etc.
Aforementioned multi-group epoxy compound (F-1) for example can list: the EPIKOTE 828 of japan epoxy resin corporate system, EPIKOTE 834, EPIKOTE1001, EPIKOTE 1004, the EPICL ON840 of big Japanese ink chemical industrial company system, EPICLON 850, EPICLON 1050, EPICLON 2055, Dongdu changes into the EPOTOTOYD-011 of corporate system, YD-013, YD-127, YD-128, the D.E.R.317 of Dow Chemical Company system, D.E.R.331, D.E.R.661, D.E.R.664, the ARALDITE6071 of Ciba Specialty Chemicals Corporation, ARALDITE 6084, ARALDITE GY250, ARALDITE GY260, the SUMI-EPOXY ESA-011 of Sumitomo Chemical Co. Ltd.'s system, ESA-014, ELA-115, ELA-128, the A.E.R.330 of industrial group of Asahi Chemical Industry system, A.E.R.331, A.E.R.661, A.E.R.664 etc. (any all is a trade name) bisphenol A type epoxy resin; The EPIKOTE YL903 of japan epoxy resin corporate system, the EPICLON152 of big Japanese ink chemical industrial company system, EPICLON165, Dongdu changes into the EPOTOTO YDB-400 of corporate system, YDB-500, the D.E.R.542 of Dow ChemicalCompany system, the ARALDITE 8011 of Ciba Specialty Chemicals Corporation system, the SUMI-EPOXYESB-400 of Sumitomo Chemical Co. Ltd.'s system, ESB-700, the A.E.R.711 of industrial group of Asahi Chemical Industry system, A.E.R.714 etc. (any all is a trade name) brominated epoxy resin; The EPIKOTE 152 of japan epoxy resin corporate system, EPIKOTE 154, the D.E.N.431 of Dow ChemicalCompany system, D.E.N.438, the EPICLON N-730 of big Japanese ink chemical industrial company system, EPICLON N-770, EPICLON N-865, Dongdu changes into the EPOTOTO YDCN-701 of corporate system, YDCN-704, the ARALDITE ECN1235 of CibaSpecialty Chemicals Corporation system, ARALDITE ECN1273, ARALDITE ECN1299, ARALDITEXPY307, the EPPN-201 of Japan's chemical drug corporate system, EOCN-1025, EOCN-1020, EOCN-104S, RE-306, the SUMI-EPOXY ESCN-195X of Sumitomo Chemical Co. Ltd.'s system, ESCN-220, the A.E.R.ECN-235 of industrial group of Asahi Chemical Industry system, ECN-299 etc. (any all is a trade name) phenolic resin varnish type epoxy resin; (any all is a trade name) bisphenol f type epoxy resins such as ARALDITE XPY306 of EPICLON830, the japan epoxy resin corporate system EPIKOTE 807 of big Japanese ink chemical industrial company system, EPOTOTOYDF-170, the YDF-175 that Dongdu changes into corporate system, YDF-2004, Ciba SpecialtyChemicals Corporation system; Dongdu changes into EPOTOTOST-2004, ST-2007, the ST-3000 bisphenol-A epoxy resins such as (trade names) of corporate system; The ARALDITE MY720 of the EPOTOTO YH-434 that the EPIKOTE 604 of japan epoxy resin corporate system, Dongdu change into corporate system, Ciba Specialty Chemicals Corporation system, (any all is a trade name) glycidyl group amine type epoxy resin such as SUMI-EPOXY ELM-120 of Sumitomo Chemical Co. Ltd.'s system; The ARALDITE CY-350 hydantoins type epoxy resin such as (trade names) of CibaSpecialty Chemicals Corporation system; DAICEL CHEMICALINDUSTRIES, (any all is a trade name) alicyclic epoxy resins such as ARALDITE CY175, CY179 of the SEROKISIDE 2021 of LTD. system, Ciba SpecialtyChemicals Corporation system; (any all is a trade name) trihydroxy benzene methylmethane type epoxy resin such as T.E.N., the EPPN-501 of the YL-933 of japan epoxy resin corporate system, Dow Chemical Company system, EPPN-502; The YL-6056 of japan epoxy resin corporate system, YX-4000, YL-6121 di-cresols types such as (any all are a trade name) or connection phenol-type epoxy resin or these potpourri; The EXA-1514 bisphenol-s epoxy resins such as (trade names) of Japan chemical drug corporate system EBPS-200, the system EPX-30 of Asahi Electro-Chemical Co. Ltd, big Japanese ink chemical industrial company system; The EPIKOTE 157S bisphenol-A phenolic varnish type epoxy resin such as (trade names) of japan epoxy resin corporate system; (any all is a trade name) four phenylol ethane type epoxy resin such as ARALDITE163 of the EPIKOTE YL-931 of japan epoxy resin corporate system, Ciba Specialty Chemicals Corporation system; (any all is a trade name) hetero ring type epoxy resin such as TEPIC of the ARALDITE PT810 of Ciba Specialty Chemicals Corporation system, daily output chemical industrial company system; O-phthalic acid diglycidyl ester resins such as the system BLEMMER DGT of Nof Corp.; Dongdu changes into four diglycidyl xylenols ethane resin such as corporate system ZX-1063; Chemical company of Nippon Steel system ESN-190, ESN-360, big Japanese ink chemical industrial company system HP-4032, EXA-4750, EXA-4700 etc. contain naphthyl epoxy resin; Big Japanese ink chemical industrial company makes the epoxy resin with bicyclopentadiene skeleton of HP-7200, HP-7200H etc.; Glycidyl methacrylate copolymerization such as Nof Corp. system CP-50S, CP-50M are epoxy resin; The copolymerization epoxy resin of further cyclohexyl maleimide and glycidyl methacrylate; Epoxide modified polybutadiene rubber derivant (for example, DAICELCHEMICAL INDUSTRIES, LTD. system PB-3600 etc.), CTBN modified epoxy (for example, Dongdu changes into YR-102, the YR-450 etc. of corporate system) etc. are not limited to these.These epoxy resin can be used singly or two or more kinds in combination.Preferred especially phenolic resin varnish type epoxy resin, hetero ring type epoxy resin, bisphenol A type epoxy resin or these potpourri in the middle of these.
As aforementioned polyfunctional group oxetane compound (F-2), can list two [(3-methyl-3-oxetanes ylmethoxy) methyl] ethers, two [(3-ethyl-3-oxetanes ylmethoxy) methyl] ether, 1, two [(3-methyl-3-oxetanes ylmethoxy) methyl] benzene of 4-, 1, two [(3-ethyl-3-oxetanes ylmethoxy) methyl] benzene of 4-, (3-methyl-3-oxetanyl) methacrylate, (3-ethyl-3-oxetanyl) methacrylate, methacrylic acid (3-methyl-3-oxetanyl) methyl esters, methacrylic acid (3-ethyl-3-oxetanyl) methyl esters, polyfunctional group oxetanes classes such as these oligomer or multipolymer, oxetanes alcohol and novolac resin, poly-(para hydroxybenzene ethene), cardo type bisphenols, calixarene kind, resorcinol calixarenes (calixresorcinarene) class, or silsesquioxane (silsesquioxane) etc. has the etherate that the resin of hydroxyl forms etc.Also can list unsaturated monomer with oxetanes ring and multipolymer of alkyl (methyl) acrylate etc. in addition.
As the compound (F-3) that in aforementioned molecule, has 2 above ring-types (sulphur) ether, can list bisphenol A-type episulfide resin YL7000 of japan epoxy resin corporate system for example etc.In addition, also available same synthetic method, and the oxygen atom of the epoxy radicals of use phenolic resin varnish type epoxy resin is replaced as the episulfide resin of sulphur atom etc.
The fit rate of Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in the aforementioned molecule is with respect to the aforementioned carboxylic acid resin's of containing of 1 equivalent (A) carboxyl, is preferably the scope of 0.6～2.5 equivalent, the scope of 0.8～2.0 equivalent more preferably.The fit rate of Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in the molecule is under the situation of less than 0.6, and residual on the solder resist film have reductions such as carboxyl, thermotolerance, alkali resistance, electrical insulating property, so not preferred.On the other hand, surpass under the situation of 2.5 equivalents, low-molecular-weight ring-type (sulphur) ether is residual on dry coating, and so reductions such as the intensity of filming thus are not preferred.
In the light-cured resin of the present invention, use under the situation of the Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in the above-mentioned molecule, preferably contain thermal curing catalyst (G).As such thermal curing catalyst (G), for example can list: the imdazole derivatives of imidazoles, glyoxal ethyline, 2-ethyl imidazol(e), 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole etc.; Dicyandiamide, benzyl dimethyl amine, 4-(dimethylamino)-N, N-dimethyl benzyl amine, 4-methoxyl-N, N-dimethyl benzyl amine, 4-methyl-N, hydrazine compounds such as amines such as N-dimethyl benzyl amine, adipic dihydrazide, sebacic dihydrazide; Phosphorus compounds such as triphenylphosphine etc., in addition, as commercially available material, for example can list 2MZ-A, 2MZ-OK, 2PHZ, 2P4BHZ, 2P4MHZ (any all is the trade name of imidazole compound), SAN-APRO that four countries change into industrial group's system, the U-CAT3503N of Ltd. system, U-CAT3502T (any all is the trade name of the block isocyanate compound of dimethyl amine), DBU, DBN, U-CATSA102, U-CAT5002 (any all be two ring type amidine compounds with and salt) etc.The thermal curing catalyst of epoxy resin, oxetane compound or can promote epoxy radicals and/or oxetanyl and carboxyl reaction just passable is not specially limited in these, so long as can separately or mix more than 2 kinds and use.In addition, can use guanamine, methyl guanamines, benzo guanamine, melamine, 2,4-diamido-6-methacryloxyethyl-s-triazine, 2-vinyl-2,4-diamido-s-triazine, 2-vinyl-4,6-diamido-s-triazine isocyanuric acid addition product, 2,4-diamido-6-methacryloxyethyl-Striazine derivatives such as s-triazine isocyanuric acid addition product, the compound and the aforementioned hot curing catalysts that preferably these are also played the tackifiers effect are used in combination.
The fit rate of these thermal curing catalysts is just enough with the ratio of common amount, for example contain the Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in carboxylic acid resin (A) or the molecule, be preferably 0.1～20 mass parts, 0.5～15.0 mass parts more preferably with respect to 100 mass parts.
For intensity of improving its physics of filming etc., also can in Photocurable resin composition of the present invention, cooperate filler as required.As such filler, can use known inorganic or organic filler commonly used, but especially preferably use barium sulphate, spherical silicon dioxide and talcum.Further, also can use nano silicon is dispersed in the compound with the ethylenically unsaturated group more than 1 or NANOCRYL (trade name) XP 0396, XP 0596, XP 0733, XP 0746, XP 0765, XP0768, XP 0953, XP 0954, XP 1045 (any all is the product hierarchy name), NANOPOX (trade name) XP0516 of Hanse-Chemie corporate system, XP 0525, the XP 0314 (any all is the product hierarchy name) of the Hanse-Chemie corporate system in the aforementioned polyfunctional epoxy resin (F-1).Also can be separately or be used more than 2 kinds with these.
The fit rate of these fillers contains carboxylic acid resin (A) with respect to 100 mass parts are above-mentioned, is preferably below 300 mass parts, and more preferably 0.1～300 mass parts is preferably 0.1～150 mass parts especially.The fit rate of filler is surpassing under the situation of 300 mass parts, and the viscosity of photosensitive composite uprises and the printing reduction, and solidfied material becomes fragile, so not preferred.
Further, contain carboxylic acid resin (A), adjustment composition for synthetic above-mentioned, or in order to adjust the viscosity that is applied on substrate, the carrier film, Photocurable resin composition of the present invention can be with an organic solvent.
As such organic solvent, can list ketone, aromatic hydrocarbon based, glycol ethers, glycol ether acetic acid ester class, ester class, alcohols, aliphatic hydrocarbon, oil series solvent etc.More particularly, ketone such as MEK, cyclohexanone; Toluene, dimethylbenzene, tetramethylbenzene etc. are aromatic hydrocarbon based; Glycol ethers such as cellulose, methylcellulose, butyl cellulose, carbitol, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, DPGME, dipropylene glycol Anaesthetie Ether, Triethylene glycol ethyl ether; Ester classes such as ethyl acetate, butyl acetate, dipropylene glycol methyl ether acetic acid esters, methyl proxitol acetate, propylene glycol ethylether acetic acid esters, propylene glycol butyl ether acetic acid esters; Alcohols such as ethanol, propyl alcohol, ethylene glycol, propylene glycol; Aliphatic hydrocarbon such as octane, decane; Oil series solvents such as sherwood oil, naphtha, hydrogenated naphtha, solvent naphtha etc.Such organic solvent can use separately or as the potpourri more than 2 kinds.
Photocurable resin composition of the present invention also can be as required, cooperates silane coupling agent, antioxidants such as defoamer such as known habitual tackifier such as known hot polymerization inhibitor commonly used, fine particle silica, organobentonite, polynite, silicone-based, fluorine system, macromoleculars such as quinhydrones, hydroquinone monomethyl ether, tert-butyl catechol, pyrogaelol, phenothiazine and/or levelling agent, imidazoles system, thiazole system, triazole system, prevents such additive kind known commonly used such as Qiang agent.
Then, dry film, solidfied material that obtains and the printed circuit board (PCB) with the solder mask that is formed by this solidfied material describe for using Photocurable resin composition of the present invention.
Photocurable resin composition of the present invention is coated with the dry dry film that obtains photo-curable by common method on carrier film.Photocurable resin composition of the present invention or its dry film form solidfied material by photocuring on copper.Photocuring can use ultraviolet exposure apparatus according, but makes its curing by oscillating laser light source, the particularly laser of wavelength 350～410nm.Printed circuit board (PCB) of the present invention is to obtain by carry out heat curing behind such photocuring.
Specifically, can be formed as follows dry film, solidfied material, printed circuit board (PCB).Promptly, for example Photocurable resin composition of the present invention is adjusted to the viscosity that is suitable for coating process with aforementioned organic solvent, be applied on the substrate by methods such as dip coating, flow coat method, rolling method, line rod rubbing method, silk screen print method, curtain-type rubbing methods, the organic solvent volatile dry that under about 60～100 ℃ temperature, makes in the composition to be comprised (temporary transient dry), thus filming of dry to touch can be formed.In addition, above-mentioned composition is coated on the carrier film, makes it dry and, it is fitted on the base material, can form resin insulating barrier as winding film.Thereafter, adopt contact (or noncontact mode), by forming figuratum photomask, optionally by the active energy beam exposure or by the direct exposing patterns of the direct exposure machine of laser, unexposed portion is developed by alkaline aqueous solution (for example 0.3～3% aqueous sodium carbonate), form corrosion-resisting pattern.Further, contain under the situation of composition of heat curing composition (F), for example be heated to about 140～180 ℃ temperature, make its heat curing, thus, the Thermocurable composition (F) that has 2 above ring-types (sulphur) ether in the aforementioned carboxylic acid resin's of containing (A) carboxyl and the molecule reacts, and can form the cured coating film of each excellents such as thermotolerance, chemical proofing, anti-hydroscopicity, adaptation, electrical characteristics.
In addition, even under the situation that does not contain Thermocurable composition (F), by thermal treatment, residual ethylenic unsaturated bond hot radical polymerization under the unreacted situation when exposure, in order to improve coating characteristic, also can heat-treat (heat curing) according to the purpose purposes.
As above-mentioned base material, can enumerate the high-frequency circuit that uses paper phenolics, paper epoxy resin, glass cloth epoxy resin, glass polyimide, glass cloth/nonwoven fabrics epoxy resin, glass cloth/paper epoxy resin, synthon epoxy resin, fluoro-tygon-polyphenylene oxide (PPO)-cyanate etc. copper clad laminate with all models (FR-4 etc.) of materials such as copper clad laminate, and polyimide film, polyethylene terephthalate film (PET film), glass substrate, ceramic substrate, wafer board etc.
Being coated with the volatile dry that carries out behind the Photocurable resin composition of the present invention is undertaken by using heated air circulation type drying oven, IR stove, electric furnace, convective drying case etc. (with the method for the contact of the hot air convection in the dryer and by the mode of nozzle spraying support, wherein the hot blast in the dryer uses the material of the thermal source that possesses the air heat mode by steam).
Behind following coating Photocurable resin composition of the present invention, the volatile dry, for resulting expose (irradiation of active energy beam) of filming.The exposed portion of filming (by the part of active energy beam irradiation) solidifies.
Can use the direct drawing apparatus of UV-lamp such as the exposure machine of the direct drawing apparatus of laser (laser direct imaging device), the exposure machine that carries metal halide lamp, lift-launch (surpassing) high-pressure sodium lamp, the exposure machine that carries mercury shot arc lamp or use (surpassing) high-pressure sodium lamp as the used exposure machine of above-mentioned active energy beam irradiation.As active energy beam, if use the laser of maximum wavelength in the scope of 350～410nm, then gas laser, Solid State Laser any can.In addition, its exposure is according to thickness etc. and different, but is generally 5～200mJ/cm
2, be preferably 5～100mJ/cm
2, 5～50mJ/cm more preferably
2Scope in.As above-mentioned direct drawing apparatus, for example can use the product of Japanese ORBOTECH corporate system, PENTAX corporate system etc., also can use the arbitrary device of maximum wavelength at the device of the oscillating laser of 350～410nm.
As aforementioned developing method, can utilize infusion process, spray process, spray-on process, brushing method etc., as developer solution, can use alkaline aqueous solutions such as potassium hydroxide, NaOH, sodium carbonate, sal tartari, sodium phosphate, sodium silicate, ammonia, amine.
Embodiment
Below, embodiment and comparative example are shown, the present invention is specifically described, the present invention is not limited to following embodiment certainly." part " short of special qualification all is meant " mass parts " in addition, below.
＜contain the synthetic of carboxylic acid resin 〉
According to following synthesis example, make the carboxy resin (A) that contains of the present invention.
With 220 parts of cresols phenolic resin varnish type epoxy resins (big Japanese ink chemical industry (strain) system, " EPICLON " (registered trademark) N-695, epoxide equivalent: 220) put into the four-hole boiling flask that has stirring machine and reflux condenser, add 214 parts of carbitol acetic acid esters, heating for dissolving.Then, add 0.46 part of quinhydrones, 1.38 parts of triphenylphosphines as catalysts as polymerization inhibitor.With this mixture heated to 95～105 ℃, slowly drip 72 parts of acrylic acid, make its reaction 16 hours.This reaction product is cooled to 80～90 ℃, adds 106 parts of tetrabydrophthalic anhydrides, make its reaction 8 hours, after the cooling, take out reaction solution (being called " varnish (A-1) ").The acid number of the solid matter that contains the carboxylic acid photoresist that obtains like this is that 100mgKOH/g, non-volatile content are 65%.
＜embodiment 1～7 and comparative example 1～2 〉
It is mixing with three roller roller mills the varnish (A-1) that obtains in the aforementioned carboxylic acid resin of containing synthetic and the composition shown in the table 1 to be pressed the described cooperation ratio of table 1, obtains Photocurable resin composition.
Table 1
For the Photocurable resin composition of embodiment 1～7 and comparative example 1～2, according to following metewand assess performance and characteristic.The results are shown in table 2.
Performance evaluation:
＜the suitableeest exposure/light sensitivity 〉
The circuit pattern substrate polishing of the thick 35 μ m of copper is ground after washing, drying, and then by silk screen print method whole coating of Photocurable resin composition with embodiment 1～7 and comparative example 1～2, drying is 60 minutes in 80 ℃ heated air circulation type drying oven.After the drying, use the exposure device that carries metal halide lamp, by stage metraster (Kodak No.2) exposure, when the pattern of residual stage metraster is 7 sections when developing (30 ℃, 0.2MPa, 1 quality % aqueous sodium carbonate) 60 seconds as the suitableeest exposure.
＜resolution 〉
The circuit pattern substrate polishing of line/be spaced apart 300/300, the thick 35 μ m of copper is ground after washing, drying, by the Photocurable resin composition coating of silk screen print method with embodiment 1～7 and comparative example 1～2, drying is 30 minutes in 80 ℃ heated air circulation type drying oven then.After the drying, use the exposure device exposure of carrying metal halide lamp.Exposing patterns uses directly retouches the line of describing 20/30/40/50/60/70/80/90/100 μ m with data or photomask in spacer portion.Exposure is shone active energy beam with the suitableeest exposure of photosensitive polymer combination.After the exposure, develop, describe pattern, obtain cured coating film by 150 ℃ * 60 minutes heat curings with 30 ℃ 1 quality % aqueous sodium carbonates.
Use is adjusted to 200 times optical microscope and is obtained the minimum residual wires of resulting solder resist with the cured coating film of photosensitive polymer combination.
Attribute testing:
(estimating the making of substrate)
Be applied on the copper clad laminate that forms pattern, descend dry 20 minutes, cool to room temperature by the whole face of composition of serigraphy at 80 ℃ with embodiment 1～4 and comparative example 1～2.On this substrate, use the exposure device that carries metal halide lamp with the suitableeest exposure exposure solder resist pattern, with expulsion pressure 2kg/cm
2Condition with 1%Na
2CO
3Aqueous solution was developed 60 seconds, obtained corrosion-resisting pattern.By the UV furnace conveyor at accumulated exposure amount 1000mJ/cm
2Condition under this substrate carried out ultraviolet ray irradiation after, 150 ℃ of heating 60 minutes and solidifying down.Estimate following characteristic for resulting printed base plate (evaluation substrate).
＜the color of filming 〉
Judge the solder resist of the foregoing description and comparative example by the color of visual solidfied material.
＜copper circuit variable color 〉
To estimate substrate again and heat 2 hours down, by degree as the variable color on the copper circuit that judges at 150 ℃.
00: do not have variable color fully.
Zero: with prima facies than some variable color a little, but thin part of resist layer and thick part do not have difference fully.
△: confirm variable color, but part that resist layer approaches and thick part do not have difference fully.
*: confirm the variable color of the thin part of resist layer, with the significant difference of thick part.
＜solder heat resistance 〉
The evaluation substrate of coating rosin series solder flux is immersed in the solder bath that is redefined for 260 ℃, behind modification alcohol washing solder flux, peels off by the visual expansion of estimating resist layer.Determinating reference is as follows.
Zero:, also can confirm less than peeling off even flooded for 10 seconds, flood more than 3 times repeatedly at every turn.
△: flooded for 10 seconds at every turn, when flooding more than 3 times repeatedly, peel off a little.
*: flooded for 10 seconds at every turn, flood in 3 times, exist resist layer to expand, peel off.
The gold-plated property of＜chemically-resistant 〉
Use the electroless nickel bath and the chemical gilding of commercially available product to bathe, under the condition of nickel 0.5 μ m, golden 0.03 μ m, carry out plating, by belt stripping test estimate resist layer have or not peel off, plating have or not infiltration after, under the test condition of aforementioned solder heat resistance, be immersed in 10 seconds of solder bath, washing, after the drying, estimate resist layer by belt stripping test and have or not and peel off.Determinating reference is as follows.
Zero: can't see variation fully.
△: see a little infiltration behind the plating, peel off after seeing solder heat resistance.
*: peel off behind the plating.
＜electrochemical corrosion resistant 〉
Use the comb-type electrode B sample Alloy instead of Copper foil substrate of IPC B-25, under above-mentioned condition, make and estimate substrate, this comb-type electrode is applied the bias voltage of DC 100V, confirm in 85 ℃, the constant temperature and humidity cabinet of 85%R.H., to have or not migration after 1000 hours.Determinating reference is as follows.
Zero: full confirmation is less than variation
△: some variation a little
*: move
＜acid resistance 〉
At room temperature at 10vol%H
2SO
4Dipping is estimated substrate 30 minutes in the aqueous solution, and what stripping that affirmation is infiltrated, filmed and tape stripping caused peels off.Determinating reference is as follows.
Zero: do not have infiltration, stripping, peel off.
△: confirm infiltration, stripping a little or peel off.
*: confirm infiltration significantly, stripping or peel off.
Table 2
Claims (17)
1. Photocurable resin composition, it can develop and contain compound (C) and the red stain (D) that has 2 above ethylenically unsaturated groups in carboxylic acid resin (A), Photoepolymerizationinitiater initiater (B), the molecule by alkaline aqueous solution.
2. Photocurable resin composition according to claim 1, the fit rate that contains carboxylic acid resin (A) is 20～60 quality % in whole compositions.
3. Photocurable resin composition according to claim 1, the scope of the use amount of Photoepolymerizationinitiater initiater (B) are that to contain carboxylic acid resin (A) with respect to 100 mass parts be the ratio of 1～30 mass parts.
4. Photocurable resin composition according to claim 1, the fit rate that has the compound (C) of 2 above ethylenically unsaturated groups in the molecule are to be the ratio of 5～100 mass parts with respect to the aforementioned carboxylic acid resin of containing of 100 mass parts (A).
5. Photocurable resin composition according to claim 1, it further contains blue colorant (E1).
6. Photocurable resin composition according to claim 1, it further contains yellow colorants (E2).
7. according to each described Photocurable resin composition of claim 1 to 6, the tone of described Photocurable resin composition is blue, green, purple or orange.
8. Photocurable resin composition according to claim 1, red stain (D) are any the red stain in the not halogen-containing and azo group.
9. Photocurable resin composition according to claim 8, red stain (D) is for being selected from least a in monoazo system, bisdiazo system, azo lake system, benzimidazolone Xi, perylene system, pyrrolopyrrole diketone system, condensation azo system, anthraquinone system, the quinacridone.
10. Photocurable resin composition according to claim 5, blue colorant (E1) is a phthalocyanine blue.
11. Photocurable resin composition according to claim 1, it further contains Thermocurable composition (F).
12. according to claim 1 to 6,11 each described Photocurable resin compositions, it is applied on the copper and is used.
13. the photo-curable dry film, it is applied to claim 1 to 6,11 each described Photocurable resin compositions on the carrier film, and is dry and obtain.
14. the blueness of claim 1 to 6,11 each described Photocurable resin compositions, green, purple or orange solidfied material.
15. the blueness of the described dry film of claim 13, green, purple or orange solidfied material.
16. printed circuit board (PCB), it has the solder mask that is formed by the described solidfied material of claim 14 being formed with on substrate of copper circuit.
17. printed circuit board (PCB), it has the solder mask that is formed by the described solidfied material of claim 15 being formed with on substrate of copper circuit.
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| JP2007123828A JP5291893B2 (en) | 2007-05-08 | 2007-05-08 | Photocurable resin composition and cured product thereof |
| JP2007-123828 | 2007-05-08 |
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| KR (2) | KR101028604B1 (en) |
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Also Published As
| Publication number | Publication date |
|---|---|
| TW200921272A (en) | 2009-05-16 |
| CN102419514B (en) | 2014-05-28 |
| KR101120252B1 (en) | 2012-03-16 |
| TW201333629A (en) | 2013-08-16 |
| KR20080099182A (en) | 2008-11-12 |
| KR101028604B1 (en) | 2011-04-11 |
| CN101303528B (en) | 2013-03-27 |
| TWI401531B (en) | 2013-07-11 |
| CN102419514A (en) | 2012-04-18 |
| TWI486707B (en) | 2015-06-01 |
| JP2008281652A (en) | 2008-11-20 |
| JP5291893B2 (en) | 2013-09-18 |
| KR20110028477A (en) | 2011-03-18 |
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