JP5439765B2 - 新規なポリイミド樹脂及び感光性ポリイミド樹脂組成物 - Google Patents
新規なポリイミド樹脂及び感光性ポリイミド樹脂組成物 Download PDFInfo
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- JP5439765B2 JP5439765B2 JP2008211393A JP2008211393A JP5439765B2 JP 5439765 B2 JP5439765 B2 JP 5439765B2 JP 2008211393 A JP2008211393 A JP 2008211393A JP 2008211393 A JP2008211393 A JP 2008211393A JP 5439765 B2 JP5439765 B2 JP 5439765B2
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- Prior art keywords
- polyimide resin
- dianhydride
- formula
- photosensitive
- resin composition
- 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.)
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- 229920001721 polyimide Polymers 0.000 title claims description 135
- 239000009719 polyimide resin Substances 0.000 title claims description 109
- 239000000203 mixture Substances 0.000 title claims description 50
- -1 siloxane diamine compound Chemical class 0.000 claims description 84
- 125000003368 amide group Chemical group 0.000 claims description 46
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 40
- 150000004985 diamines Chemical class 0.000 claims description 26
- 239000003431 cross linking reagent Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 claims description 15
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 9
- KECOIASOKMSRFT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(O)=CC=2)=C1 KECOIASOKMSRFT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims 2
- AQVOMFPTJXMAQE-UHFFFAOYSA-N 4-propylphthalic acid Chemical compound CCCC1=CC=C(C(O)=O)C(C(O)=O)=C1 AQVOMFPTJXMAQE-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000004642 Polyimide Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 238000007747 plating Methods 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000010408 film Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000003513 alkali Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010931 gold Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 239000004020 conductor Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000006078 metal deactivator Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 238000007772 electroless plating Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 230000036211 photosensitivity Effects 0.000 description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 3
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 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 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000006713 insertion reaction Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
- UWQPDVZUOZVCBH-UHFFFAOYSA-N 2-diazonio-4-oxo-3h-naphthalen-1-olate Chemical class C1=CC=C2C(=O)C(=[N+]=[N-])CC(=O)C2=C1 UWQPDVZUOZVCBH-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DVEHYHFBRYRCJC-UHFFFAOYSA-N C(=O)(O)C=1C=C(OC2=CC=C(C=C2)C2(C3=CC=CC=C3C=3C=CC=C(C2=3)C(=O)O)C2=CC=C(C=C2)OC2=CC(=C(C=C2)C(=O)O)C(=O)O)C=CC=1C(=O)O Chemical compound C(=O)(O)C=1C=C(OC2=CC=C(C=C2)C2(C3=CC=CC=C3C=3C=CC=C(C2=3)C(=O)O)C2=CC=C(C=C2)OC2=CC(=C(C=C2)C(=O)O)C(=O)O)C=CC=1C(=O)O DVEHYHFBRYRCJC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229920001646 UPILEX Polymers 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 1
- PULOARGYCVHSDH-UHFFFAOYSA-N 2-amino-3,4,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1OC1CC1=C(CC2OC2)C(N)=C(O)C=C1CC1CO1 PULOARGYCVHSDH-UHFFFAOYSA-N 0.000 description 1
- MZZYGYNZAOVRTG-UHFFFAOYSA-N 2-hydroxy-n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=NC=NN1 MZZYGYNZAOVRTG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- PKNQCLIOQMEQOR-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)phenoxy]propane-1,2-diol Chemical compound OCC(O)COC1=CC=CC(OCC(O)CO)=C1 PKNQCLIOQMEQOR-UHFFFAOYSA-N 0.000 description 1
- FMZPVXIKKGVLLV-UHFFFAOYSA-N 3-phenyl-2,4-dihydro-1,3-benzoxazine Chemical compound C1OC2=CC=CC=C2CN1C1=CC=CC=C1 FMZPVXIKKGVLLV-UHFFFAOYSA-N 0.000 description 1
- GQIBNJYPPDPDEU-UHFFFAOYSA-N 3-phenyl-6-[(3-phenyl-2,4-dihydro-1,3-benzoxazin-6-yl)sulfonyl]-2,4-dihydro-1,3-benzoxazine Chemical compound C=1C=C2OCN(C=3C=CC=CC=3)CC2=CC=1S(=O)(=O)C(C=C1C2)=CC=C1OCN2C1=CC=CC=C1 GQIBNJYPPDPDEU-UHFFFAOYSA-N 0.000 description 1
- IXLCLXDFIPWZOF-UHFFFAOYSA-N 4-[9-(3,4-dicarboxyphenyl)fluoren-9-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1(C=2C=C(C(C(O)=O)=CC=2)C(O)=O)C2=CC=CC=C2C2=CC=CC=C21 IXLCLXDFIPWZOF-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- CEPXCCCPSUJYQE-UHFFFAOYSA-N 6-(3,5-ditert-butyl-4-hydroxyphenyl)-2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]-4-oxohexanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)CC(C(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(=O)NN)=C1 CEPXCCCPSUJYQE-UHFFFAOYSA-N 0.000 description 1
- FFZBTLLLUJDPAK-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hept-3-ene-1-carboxylic acid Chemical compound C12(C(CC=CC1)O2)C(=O)O FFZBTLLLUJDPAK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IKWKMCVIIBILCE-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=CC1C(=O)O)C(C(=O)O)C Chemical compound C(=O)(O)C=1C=C(C=CC1C(=O)O)C(C(=O)O)C IKWKMCVIIBILCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229960002050 hydrofluoric acid Drugs 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
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- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
- C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
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- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
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- 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
- G03F7/0387—Polyamides or polyimides
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
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- General Physics & Mathematics (AREA)
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Description
冷却機、温度計、滴下ロート及び撹拌機を備えた2リットルの反応器に、トルエン500g、式(2)のシロキサンジアミン(R1、R2=トリメチレン; 商品名 X−22−9409、信越化学工業株式会社)200g(0.148mmol)、及びトリエチルアミン30g(0.297mol)を投入した。次いで、p−ニトロベンゾイルクロライド54.7g(0.295mol)をトルエン300gに溶解させた溶液を滴下ロートに装入した。反応器内を撹拌しながら50℃まで昇温した後、滴下ロート内の溶液を1時間かけて滴下した。滴下終了後、昇温させ撹拌を6時間行い、還流下で反応させた。反応終了後、30℃に冷却し、800gの水を加えて強撹拌した後、分液ロートに移液し、静置分液した。5%水酸化ナトリウム水溶液300gでの洗浄を3回行い、飽和塩化ナトリウム水溶液300gでの洗浄を2回行った。有機層を硫酸マグネシウムで乾燥、トルエン溶媒を加熱減圧溜去し濃縮後、60℃で1日減圧乾燥した。得られたα−(p−ニトロベンゾイルイミノプロピルジメチルシロキシ)−ω−(p−ニトロベンゾイルイミノプロピルジメチルシリル)オリゴ(ジメチルシロキサン−co−ジフェニルシロキサン)(以下、ジニトロ体)を、収量235g(収率96%)で得た。ジニトロ体は淡黄色のオイル状であった。
3450cm−1(νN−H)、3370cm−1(νN−H)、3340cm−1(νN−H)、3222cm−1(νN−H)、1623cm−1(νC=O)、1260cm−1(νCH3)、1000〜1100cm−1(νsi−o)
1H−NMR(CDCl3,δ):
−0.2〜0.2(m、メチル)、0.4〜0.6(m、4H、メチレン)、1.4〜1.8(m、4H、メチレン)、3.2〜3.5(m、4H、メチレン)、3.9(bs、4H、アミノ基水素)、5.8〜6.3(m、2H、アミド基水素)、6.4(m、4H、アミノ基隣接芳香環水素)、7.1〜7.7(m、芳香環水素)
窒素導入管、撹拌機、及びディーン・スターク・トラップを備えた20リットル反応容器に、シロキサンジアミン化合物(X−22−9409、信越化学工業株式会社)4460.6g(3.30mol)と、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物(DSDA、新日本理化株式会社、純度99.70%)1912.7g(5.34mol)と、γ−ブチロラクトン287gと、参考例1で得た新規なアミド基含有シロキサンジアミン化合物89.0g(54.3mmol、純度97.10%)との混合液、及びトリグライム2870gを投入し、その混合液を撹拌した。更に、トルエン1100gを投入した後、混合液を185℃で2時間加熱還流させ、続いて減圧脱水およびトルエン除去を行い、酸無水物末端オリゴイミドの溶液を得た。
重合例1において、シロキサンジアミン化合物(X−22−9409、信越化学工業株式会社)を4099.8g(3.04mol)、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物(DSDA、新日本理化株式会社、純度99.70%)を1907.0g(5.32mol)、参考例1で得た新規なアミド基含有シロキサンジアミン化合物を443.7g(270.5mmol、純度97.10%)、3,3′−ジアミノ−4,4′−ジヒドロキシジフェニルスルホン(BSDA、小西化学工業株式会社、純度99.70%)を549.5g(1.96mol)と変更した点以外は重合例1と同様の操作を行い、アミド基を有する新規なポリイミド化合物を合成した。得られたポリイミドの実測固形分は47.4%であった。また、GPC(ゲル浸透クロマトグラフィー)によるポリスチレン換算分子量は、重量平均分子量として57000であった。
重合例1において、シロキサンジアミン化合物(X−22−9409、信越化学工業株式会社)を3665.3g(2.72mol)、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物(DSDA、新日本理化株式会社、純度99.70%)を1895.1g(5.29mol)、参考例1で得た新規なアミド基含有シロキサンジアミン化合物を881.9g(537.7mmol、純度97.10%)、3,3′−ジアミノ−4,4′−ジヒドロキシジフェニルスルホン(BSDA、小西化学工業株式会社、純度99.70%)を557.8g(1.99mol)と変更した点以外は重合例1と同様の操作を行い、アミド基を有する新規なポリイミド化合物を合成した。得られたポリイミドの実測固形分は47.7%であった。また、GPC(ゲル浸透クロマトグラフィー)によるポリスチレン換算分子量は、重量平均分子量として77000であった。
重合例1において、シロキサンジアミン化合物(X−22−9409、信越化学工業株式会社)を4550.2g(3.37mol)、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物(DSDA、新日本理化株式会社、純度99.70%)を1914.5g(5.34mol)、3,3′−ジアミノ−4,4′−ジヒドロキシジフェニルスルホン(BSDA、小西化学工業株式会社、純度99.70%)を535.3g(1.91mol)と変更し、参考例1で得た新規なアミド基含有シロキサンジアミン化合物を加えなかった点以外は重合例1と同様の操作を行い、ポリイミド化合物を合成した。得られたポリイミドの実測固形分は47.3%であった。また、GPC(ゲル浸透クロマトグラフィー)によるポリスチレン換算分子量は、重量平均分子量として65000であった。
重合例1において、シロキサンジアミン化合物(X−22−9409、信越化学工業株式会社)を4289.6g(3.18mol)、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物(DSDA、新日本理化株式会社、純度99.70%)を1988.4g(5.62mol)、参考例1で得た新規なアミド基含有シロキサンジアミン化合物を90.5g(54.8mmol)、3,3′−ジアミノ−4,4′−ジヒドロキシジフェニルスルホン(BSDA、小西化学工業株式会社、純度99.70%)を631.5g(2.25mol)と変更した点以外は同様の操作を行い、アミド基を有する新規なポリイミド化合物を合成した。得られたポリイミドの実測固形分は、49.50%であった。また、GPC(ゲル浸透クロマトグラフィー)によるポリスチレン換算分子量は、重量平均分子量として69000であった。
表1に従って、重合例1〜5のいずれかのポリイミド化合物100質量部に対して、感光剤としてジアゾナフトキノン(4NT−300、東洋合成工業株式会社)と、架橋剤としてBis−F型エポキシ樹脂(jER807、ジャパンエポキシレジン株式会社)、テトラグリシジルジアミノジフェニルメタン(jER604、ジャパンエポキシレジン株式会社)と、架橋剤としてオキサジン化合物(6,6′−(1−メチリデン)ビス[3,4−ジヒドロ−3−フェニル−2H−1,3−ベンゾオキサジン])(BF−BXZ、小西化学工業)と、金属不活性化剤(CDA−10、株式会社ADEKA)とを、それぞれ所定の配合量を添加し、十分に均一になるまで混合し、ポリイミド樹脂組成物を調製した。得られたポリイミド樹脂組成物について、以下に説明するように、現像性、無電解Ni/Auメッキ耐性、カール性、難燃性を試験評価し、得られた結果を表1及び表2に示す。
ポリイミド樹脂組成物を、乾燥厚が10μmとなるように、予め0.3μm相当の化学研磨処理を施した銅箔の片面に塗布し、80℃で10分間乾燥し、銅箔の片面にポリイミド樹脂層を形成し、試験片Aを作成した。得られた試験片Aのポリイミド樹脂層に対し、所定のポジパターンの露光マスクを介し、超高圧水銀ランプ(g線、h線、i線の三線混合)を用いて2500mJ/cm2の積算光量で光照射した。その後、試験片Aを40℃の3%水酸化ナトリウム水溶液に浸漬し、続いて40℃の温水に2分間浸漬することによりアルカリ現象を行った。さらに、10%硫酸水溶液に浸漬して中和した後、蒸留水で十分に洗浄し乾燥させ一連の現像プロセスを完結させた。3%水酸化ナトリウム水溶液の浸漬時間が60秒以下であれば、実用的なアルカリ現像性と評価できる。
A: 3%水酸化ナトリウム水溶液(40℃)で現像時間が60秒以下である場合
B: 3%水酸化ナトリウム水溶液(40℃)で現像時間が60秒を超える場合
平坦な25μm厚のポリイミドフィルム(Upilex 25S、宇部興産社)に、ポリイミド樹脂組成物を、乾燥厚が10μmとなるように塗布し、80℃で10分間乾燥した(片面塗布)。続いて、窒素雰囲気下200℃で1時間加熱しポリイミド樹脂層の架橋を完成させ(ポストベーク)、試験片Bを得た。得られた試験片Bを10cm角にカットし、製膜面が天井に向くように平坦な定盤に載置し、四隅の浮きの高さを測定し、それらの平均値を算出した。その平均値が10mm未満であれば、実用的なカール性と評価できる。
AA: 平均値が2mm未満である場合
A: 平均値が2mm以上10mm未満である場合
B: 平均値が10mm以上であるが、円筒状に丸くならない場合
C: 円筒状に丸くなる場合
現像性試験に使用した試験片Aを、窒素雰囲気下200℃で1時間加熱し、ポリイミド樹脂層の架橋を完結させた(ポストベーク)。次に、無電解ニッケルメッキ処理(使用メッキ液:NPR−4、上村工業株式会社)を行い、連続して更に無電解金メッキ処理(使用メッキ液:TKK−51、上村工業株式会社)を行った。無電解Ni/Auメッキ処理後の試験片Aの導体開口部周辺のポリイミド樹脂層端部の変色が、その際から50μm未満であれば実用的な無電解Ni/Auメッキ耐性であると評価できる。
AA: 開口際変色が確認できない場合
A: 開口際変色が20μm以上〜50μm未満である場合
C: 開口際変色が50μm以上である場合
平坦な25μm厚のポリイミドフィルム(Upilex 25S、宇部興産社)に、ポリイミド樹脂組成物を、それぞれの乾燥厚が10μmとなるように両面塗布し、80℃で10分乾燥した。続いて、窒素雰囲気下200℃で1時間加熱し、ポリイミド樹脂層の架橋を完結させ(ポストベーク)、それにより試験片Cを得た。得られた試験片CをUL−94−VTM規格に従って試験し、以下の基準に従って評価した。
A: UL−94−VTM−0を満たす場合
C: UL−94−VTM−0を満たさない場合
Claims (11)
- 式(1)で表されるアミド基含有シロキサンジアミン化合物を含むジアミン成分と、ピロメリットテトラカルボン酸二無水物、3,3′,4,4′−ベンゾフェノンテトラカルボン酸二無水物、3,3′,4,4′−ジフェニルエーテルテトラカルボン酸二無水物、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物、2,2′−ビス(3,4−ジカルボキシフェニル)プロパン酸二無水物、1,4,5,8−ナフタレンテトラカルボン酸二無水物、4,4′−(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物、9,9−ビス(3,4−ジカルボキシフェニル)フルオレン酸二無水物、9,9−ビス[4−(3,4−ジカルボキシフェノキシ)フェニル]フルオレン酸二無水物及び1,2,3,4−シクロブタン酸二無水物からなる群より選択される少なくとも一種の芳香族酸二無水物を含む酸二無水物成分とを、イミド化してなるポリイミド樹脂であって、
該ジアミン成分が、式(1)で表されるアミド基含有シロキサンジアミン化合物を0.1〜20モル%で含有し、且つ式(2)で表されるシロキサンジアミン化合物を、40〜90モル%含有するポリイミド樹脂。
- 式(1)におけるR1及R2が、いずれもトリメチレンである請求項1記載のポリイミド樹脂。
- 式(1)及び式(2)において、mが1〜20である請求項1又は2記載のポリイミド樹脂。
- ジアミン成分が、更に、3,3′−ジアミノ−4,4′−ジヒドロキシジフェニルスルホンを20〜50モル%含有する請求項1〜3のいずれかに記載のポリイミド樹脂。
- 酸二無水物成分が、3,3′,4,4′−ジフェニルスルホンテトラカルボン酸二無水物である請求項1〜4のいずれかに記載のポリイミド樹脂。
- 請求項1〜5のいずれかに記載のポリイミド樹脂及び感光剤を含有する感光性ポリイミド樹脂組成物。
- ポリイミド樹脂100質量部に対し、感光剤を5〜30質量部含有する請求項6記載の感光性ポリイミド樹脂組成物。
- 更に、架橋剤を含有する請求項6又は7記載の感光性ポリイミド樹脂組成物。
- 該架橋剤が、エポキシ系架橋剤であることを特徴とする、請求項8記載の感光性ポリイミド樹脂組成物。
- 該架橋剤が、オキサジン系架橋剤であることを特徴とする、請求項8記載の感光性ポリイミド樹脂組成物。
- ポリイミド樹脂層を有する配線基板において、ポリイミド樹脂層が請求項6〜10のいずれかに記載の感光性ポリイミド樹脂組成物の膜である配線基板。
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