JP2023522232A - エトキシ/プロポキシ変性ピラゾリン有機物、その使用、光硬化性組成物及びフォトレジスト - Google Patents
エトキシ/プロポキシ変性ピラゾリン有機物、その使用、光硬化性組成物及びフォトレジスト Download PDFInfo
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- JP2023522232A JP2023522232A JP2022563920A JP2022563920A JP2023522232A JP 2023522232 A JP2023522232 A JP 2023522232A JP 2022563920 A JP2022563920 A JP 2022563920A JP 2022563920 A JP2022563920 A JP 2022563920A JP 2023522232 A JP2023522232 A JP 2023522232A
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- meth
- pyrazoline
- modified
- acrylate
- Prior art date
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- 150000003219 pyrazolines Chemical class 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 28
- 238000000016 photochemical curing Methods 0.000 claims abstract description 8
- -1 acrylate compound Chemical class 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 38
- 239000011347 resin Substances 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 19
- 238000000576 coating method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 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 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 11
- 229920000058 polyacrylate Polymers 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000012752 auxiliary agent Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- 239000000852 hydrogen donor Substances 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000006737 (C6-C20) arylalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229920000180 alkyd Polymers 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 229920001568 phenolic resin Polymers 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 16
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 abstract description 7
- 239000007787 solid Substances 0.000 abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 90
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 45
- 238000000034 method Methods 0.000 description 35
- 239000010408 film Substances 0.000 description 31
- 239000011342 resin composition Substances 0.000 description 27
- 239000001294 propane Substances 0.000 description 25
- 239000010410 layer Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000758 substrate Substances 0.000 description 21
- 230000008569 process Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000007747 plating Methods 0.000 description 17
- 238000011161 development Methods 0.000 description 16
- 230000018109 developmental process Effects 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000000178 monomer Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000004020 conductor Substances 0.000 description 11
- 239000012634 fragment Substances 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 238000004949 mass spectrometry Methods 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 238000005530 etching Methods 0.000 description 8
- 238000003475 lamination Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 244000028419 Styrax benzoin Species 0.000 description 6
- 235000000126 Styrax benzoin Nutrition 0.000 description 6
- 235000008411 Sumatra benzointree Nutrition 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 229960002130 benzoin Drugs 0.000 description 6
- 235000019382 gum benzoic Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000012369 In process control Methods 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000010965 in-process control Methods 0.000 description 5
- 238000012423 maintenance Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- XZWYAMYRMMMHKM-UHFFFAOYSA-N 1-(2-phenylphenyl)ethanone Chemical group CC(=O)C1=CC=CC=C1C1=CC=CC=C1 XZWYAMYRMMMHKM-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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- 229920001451 polypropylene glycol Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
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- 239000004698 Polyethylene Substances 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007772 electroless plating Methods 0.000 description 3
- 238000007667 floating Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- 229910000679 solder Inorganic materials 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- SUDVPELGFZKOMD-UHFFFAOYSA-N 1,2-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)C)C(C(C)C)=CC=C3SC2=C1 SUDVPELGFZKOMD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
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- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 238000010345 tape casting Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
Description
[式中、X及びYは、それぞれ独立に-CH2-CH2-又は-CH(CH3)-CH2-を表す。p及びqは、それぞれ独立に0~9の整数を表し、かつ、両者は同時に0ではない。R1は、ピラゾール環と共役する構造を有する置換基を表す。R2は、水素、C1~C10の直鎖又は分岐鎖のアルキル基、C4~C10のアルキルシクロアルキル基又はシクロアルキルアルキル基を表す。R3は、水素、C1~C20の炭化水素基、又はC6~C20のアリールアルキル基を表す。
[式中、X及びYは、それぞれ独立に-CH2-CH2-又は-CH(CH3)-CH2-を表す。p及びqは、それぞれ独立に0~9の整数を表し、かつ、両者は同時に0ではない。R1は、ピラゾール環と共役する構造を有する置換基を表す。R2は、水素、C1~C10の直鎖又は分岐鎖のアルキル基、C4~C10のアルキルシクロアルキル基又はシクロアルキルアルキル基を表す。R3は、水素、C1~C20の炭化水素基、又はC6~C20のアリールアルキル基を表す。]
-CH2-CH2-O(EO)及び/又は-CH(CH3)-CH2-O(PO)の導入により、上記EO/PO変性ピラゾリン類有機物は、優れた水溶性又は水乳化性能を有することとなり、かつ固体であり、添加及び使用が便利である。同時に、式(I)で示される構造の吸収波長帯域が360~400nm間であり、増感剤として光硬化系(例えばビスイミダゾール類光開始剤を含有する系)へ使用されることが特に好適であり、光硬化系の感度を大幅に向上させることができる。これに加えて、上記構造を有するEO/PO変性ピラゾリン類有機物は、高い感度向上性を有し、使用量が少なく、かつ添加及び使用が便利である。
アルカリ可溶性重合体は、感光性樹脂組成物に成膜機能を付与することができる。アルカリ可溶性重合体として、このような特性を有する重合体であれば適用可能であり、特に限定されない。
エチレン性不飽和二重結合を有する化合物は、感光性樹脂組成物の成膜を促進することができる。エチレン性不飽和二重結合を有する化合物については特に限定されず、分子内に少なくとも1つのエチレン性不飽和結合を有する光重合性化合物であれば使用可能である。好ましくは、エチレン性不飽和二重結合を有する化合物としては、α,β-不飽和カルボン酸と多価アルコールとを反応させて得られる化合物、ビスフェノールA系(メタ)アクリレート化合物、α,β-不飽和カルボン酸とグリシジル基含有化合物とを反応させて得られる化合物、分子内にウレタン結合を有する(メタ)アクリレート化合物等のウレタンモノマー、ノニルフェノキシポリエチレンオキシアクリレート、γ-クロロ-β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、β-ヒドロキシエチル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、フタル酸系化合物、アルキル(メタ)アクリレートからなる群より選ばれる1種又は2種以上であるが、これらに限られない。他の種類のエチレン性不飽和二重結合を有する化合物と比べて、上記のようなものを選択、使用することで感光性樹脂の成膜性の更なる向上、コスト低下に有利である。
上記第1の増感剤(C)は、上記EO/PO変性ピラゾリン類増感剤のうちの1種又は2種以上であり、構造は前述した通りである。
上記感光性組成物において、上記EO/PO変性ピラゾリン類増感剤に加えて、光開始剤および他の種類の増感剤をさらに含んでもよく、光開始剤は、本分野で常用される種類を用いることもできる。上記光開始剤及び/又は第2の増感剤としては、ビスイミダゾール類有機物、アクリジン類有機物、芳香族ケトン類有機物、アントラキノン類有機物、ベンゾイン及びベンゾインアルキルエーテル類有機物、オキシムエステル類有機物、トリアジン類有機物、クマリン類有機物、チオキサントン類有機物のうちの1種又は2種以上が挙げられるが、これらに限られない。
上記の各成分に加えて、任意選択として、本発明の感光性樹脂組成物には、さらに必要に応じてその他の助剤を適量で含有してもよい。1つの好適な実施例において、助剤としては、水素供与体、染料、顔料、光発色剤、充填剤、可塑剤、安定化剤、塗布助剤、剥離促進剤のうちの1種又は2種以上が挙げられるが、これらに限られない。
本発明の感光性樹脂組成物は、ドライフィルム、即ち、感光性樹脂積層体に製造して、さらにプリント基板、保護パターン、導体パターン、リードフレーム、半導体パッケージの製造へ応用し、異なる工程を経て異なる基材上に所望のパターンを形成することができる。
本発明のドライフィルム、即ち、感光性樹脂積層体は、感光性樹脂組成物により形成された感光性樹脂層と、当該感光性樹脂層を支持する支持体と、を含む。
感光性樹脂積層体を基板上に積層する。
感光性樹脂積層体における感光性樹脂層を露光し、活性光線をパターン状に照射して露光部分を光硬化させる。
感光性樹脂層の未露光部分を現像液で除去し、保護パターンを形成する。
銅張積層板又はフレキシブル基板表面の、保護パターンで被覆されていない部分をエッチング又はめっきする。
保護パターンを当該銅張積層板又はフレキシブル基板から剥離する。
本発明の感光性樹脂組成物は、プリント基板、保護パターン、導体パターン、リードフレーム、半導体パッケージなどの製造に用いるように、ウェットフィルム方式で基板上に直接に塗布して使用してもよい。
以下、具体的な実施例を参照しながら本願をさらに詳しく説明し、これらの実施例は、本願の保護範囲を制限するものではないと理解され得る。
1.1 生成物C1の製造
1.1.1 中間体Aの製造
4つ口フラスコに183.1gのp-ヒドロキシベンズアルデヒドと、5.0gのピリジニウム-p-トルエンスルホナートと、300.0mLのジクロロエタンとをこの順に投入し、温度を45±5℃に制御して126.0gのジヒドロピランを滴下し、滴下時間が約1hであり、滴下終了後、引き続き2h撹拌した。HPLCによりインプロセス制御を行いp-ヒドロキシベンズアルデヒドの残量が1%未満となったときに、温度維持を終了した。反応系に52.0gの30%水酸化ナトリウム水溶液をゆっくり滴下し、水層を分離し、下層の有機層を100.0gの純水で1回洗浄し、回転蒸発によりジクロロメタンを除去し、275.2gの中間体Aを得、純度が98.12%であり、そのまま次工程の反応に用いる。
4つ口フラスコに247.1gの中間体Aと、235.2gのアセチルビフェニルと、300.0mLのメタノールとをこの順に投入し、温度を25±5℃に制御して80.0gの40%水酸化ナトリウム水溶液を滴下し、滴下時間が約2hであり、滴下終了後、引き続き6h撹拌した。HPLCによりインプロセス制御を行い、アセチルビフェニルの残量が1%未満となったときに、温度維持を終了した。ろ過して415.6gの中間体Bを得、純度が93.65%であり、そのまま次工程の反応に用いる。
4つ口フラスコに384.4gの中間体Bと、50.0gの37%の濃塩酸と、500.0mLのジクロロエタンとをこの順に投入し、温度を25±5℃に制御して引き続き6h撹拌した。HPLCによりインプロセス制御を行い、中間体Bの残量が1%未満となったときに、温度維持を終了した。ろ過、乾燥して210.5gの中間体Cを得、純度が98.95%である。
4つ口フラスコに180.0gの中間体Cと、500.0mLの氷酢酸とをこの順に投入し、温度を50±5℃に制御して108.0gのフェニルヒドラジンを滴下し、滴下時間が約2hであり、滴下終了後、引き続き8h撹拌した。ろ過して、メタノールで再結晶させ、乾燥して214.5gの中間体Dを得、純度が99.65%である。
4つ口フラスコに56.1gのp-トルエンスルホニルクロリドと、50.0gのトリエチレングリコールモノメチルエーテルと、200.0gのジクロロメタンと、0.5gの4-ジメチルアミノピリジンとをこの順に投入し、30℃に昇温した後、34.0gのトリエチルアミンを滴下し、約30min後に滴下終了し、その後、温度を維持しながら反応させた。HPLCによりインプロセス制御を行い、p-トルエンスルホニルクロリドの残量が1%未満となったときに、温度維持を終了した。反応液を吸引ろ過した後、ろ過液を100gの純水で3回洗浄し、無水硫酸ナトリウムで乾燥した後、ろ過、濃縮して、80.3gの中間体Eを得、純度が96.51%である。更なる精製を行う必要がなく、そのまま次工程の反応に用いた。
4つ口フラスコに68.0gの中間体Eと、250.0gのアセトニトリルと、73.6gの中間体Dと、49.1gの炭酸カリウムとをこの順に投入し、撹拌を開始し、80℃に昇温し、温度を維持しながら反応させた。HPLCによりインプロセス制御を行い、中間体Dの残量が1%未満となったときに、温度維持を終了した。300gの純水と300gの酢酸エチルとを添加し、水層を分離し、上層の有機層を水で2回洗浄し、酢酸エチルを一倍量となるように減圧蒸留した後、100mLのメタノールを添加し、ろ過、乾燥した後に92.2gの生成物C1を得、純度が99.12%である。
生成物C1の合成方法を参照して、原料fであるトリエチレングリコールモノメチルエーテルをトリプロピレングリコールモノメチルエーテルに置き換え、生成物C2を得、純度が99.28%である。
生成物C1の合成方法を参照して、原料fであるトリエチレングリコールモノメチルエーテルをトリエチレングリコールモノベンジルエーテルに置き換え、生成物C3を得、純度が99.54%である。
表1に示す配合成分を参照して、各成分を均一に混合して感光性樹脂組成物を製造した。別途説明がない限り、表1に示す部数がいずれも重量部である。
3.1 評価方式
<ドライフィルムの作製>
感光性樹脂組成物を十分に撹拌し、支持体としての厚さ25μmのポリエチレンテレフタレートフィルムの表面上にバーコーターを用いて均一に塗布し、95℃の乾燥機中で5分間乾燥して厚さ40μmの感光性樹脂層を形成し、その後、感光性樹脂層の、ポリエチレンテレフタレートフィルムが積層されていない表面に、保護層としての厚さ15μmのポリエチレンフィルムを貼り合わせ、ドライフィルムを得る。
基板として、厚さ35μmの圧延銅箔を積層した厚さ1.2mmの銅張積層板を用いて、表面を湿式ポリシングロール研磨[3M社製のScotch-Brite(登録商標)HD#600、2回通し]した。
ポリエチレンフィルム保護層をドライフィルムから剥離し、その後、ホットロールラミネーター(旭化成製のAL-70)を用いて、ロール温度105℃で、60℃に予め加熱した銅張積層板上に積層した。気体圧力が0.35MPaであり、積層速度が1.5m/minであった。
マスクを、支持体としてのポリエチレンテレフタレートフィルム上に放置し、超高圧水銀灯(オーク製作所製、HMW-201KB)を用いて、60mJ/cm2の照射エネルギーで感光層を露光した。
ポリエチレンテレフタレートフィルムを剥離し、アルカリ現像機(富士機工製のドライフィルム用現像機)を用いて、30℃の1質量%Na2CO3水溶液を感光性樹脂層上にスプレーし、最小現像時間の2倍の時間で感光性樹脂層の未露光部分を溶解、除去した。未露光部分の感光性樹脂層が完全に溶解するのに必要な最短時間を最小現像時間とした。
(1)相溶性評価
表1に示す組成を有する感光性樹脂組成物を十分に撹拌、混合し、支持体としての厚さ19μmのポリエチレンテレフタレート薄膜の表面にバーコーダを用いて均一に塗布した。95℃の乾燥機中で4min乾燥し、感光性樹脂層を形成した。その後、塗布表面を目視により観察し、以下の方式でランク分けした。
●:塗布面上に未溶解物が析出
透明から黒色に21段階で明度が変化しているStouffer製21段ステップタブレットを用いて、ラミネート後の基板を15min露光し、その感度を評価した。露光後、最小現像時間の2倍の時間で現像し、フォトレジスト膜が完全に残存しているステップタブレット段数が8である露光量に応じて、以下のようにランク分けした。
◎:露光量が20mJ/cm2~50mJ/cm2(上下限値を含まない)
●:露光量が50mJ/cm2以上。
露光部と未露光部の幅が1:1の比率のラインパターンマスクにより、ラミネート後の基板を15min露光し、その後、最小現像時間の2倍の現像時間で現像し、硬化フォトレジストラインが正常に形成されている最小マスクライン幅を解像度の値とした。以下のようにランク分けした。
◎:解像度値が30μm~50μm(上下限値を含まない)
●:解像度値が50μm以上。
感光性樹脂積層体中の厚さ40μm、面積0.16m2の感光層(フォトレジスト層)を、200mlの1質量%Na2CO3水溶液に溶解させ、循環式スプレー装置を用いてスプレー圧0.1MPa、3時間スプレーを行った。その後、現像液を1日放置し、凝集物の発生を観察した。凝集物が多量に発生するとスプレー装置の底部又は側面に粉状のもの又は油状のものが観察される。また、現像液に凝集物が浮遊することもある。現像液凝集性が良好な組成はこれら凝集物が全く発生しないか、もしくは発生しても極微量で水洗で簡単に洗い流すことが可能である。凝集物の発生状態については目視観察により以下のようにランク分けした。
◎:スプレー装置の底部もしくは側面の一部及び現像液に凝集物が浮遊している。水洗してもすべてを洗い流すことはできない。
●:スプレー装置全体に凝集物が見られ且つ現像液に凝集物が浮遊している。水洗でもすべてを洗い流すことは不可能でほとんどが残留する。
露光部と未露光部の幅が1:100の比率のラインパターンマスクにより、ラミネート後の基板を15min露光し、その後、最小現像時間の2倍の現像時間で現像し、硬化フォトレジストラインが正常に形成されている最小マスク幅を付着力の値とした。
◎:付着力値が30μm~50μm(上下限値を含まない)
●:付着力値が50μm以上。
評価結果を表3-1に示す。
本発明のEO/PO変性ピラゾリン類増感剤は、感光性樹脂組成物に適用される際に、生成物の相溶性が良く、感度が高く、解像度が高く、溶解性が高く、付着力が高く、現像性に優れ、現像時の親水性に優れ、循環使用時の現像液中のスラッジ量を明らかに低減し、現像液を複数回繰り返し、有効に使用することができる。当該感光性樹脂組成物は、ドライフィルム及びウェットフィルムの方式でプリント基板、保護パターン、導体パターン、リードフレーム、半導体パッケージ等の製造において広く使用される。
Claims (13)
- p+q≦9、好ましくはp+q≦6であることを特徴とする請求項1に記載のエトキシ/プロポキシ変性ピラゾリン有機物。
- 前記R1は、フェニル基、ナフチル基、ピロリル基、イミダゾリル基、カルバゾリル基、インドリル基、C2~C10のアルケニル基、C4~C8のシクロアルカジェニル基から選ばれるか、あるいは、前記基における水素原子は、それぞれ独立にC1~C10の直鎖又は分岐鎖のアルキル基、C4~C10のアルキルシクロアルキル基又はシクロアルキルアルキル基、C3~C10のシクロアルキル基、C6~C15のアリール基、C6~C12のアルキルアリール基、C6~C12のアリールアルキル基、C2~C20のヘテロアリールにより置換されてもよく、
前記R2は、水素、C1~C6の直鎖又は分岐鎖のアルキル基から選ばれ、
前記R3は、水素、C1~C6の直鎖又は分岐鎖のアルキル基、ベンジル基から選ばれることを特徴とする請求項1又は2に記載のエトキシ/プロポキシ変性ピラゾリン有機物。 - 前記R1は、フェニル基、ナフチル基、ピロリル基、イミダゾリル基、カルバゾリル基、インドリル基、C2~C6のアルケニル基、C4~C6のシクロアルカジェニル基、C1~C5のアルキル基で置換されたフェニル基、C3~C6のシクロアルキル基で置換されたフェニル基、C6~C10のアリール基で置換されたアルケニル基、C6~C10のアルキルアリール基で置換されたアルケニル基、C6~C10のアリールアルキル基で置換されたアルケニル基から選ばれることを特徴とする請求項3に記載のエトキシ/プロポキシ変性ピラゾリン有機物。
- 前記R2は、水素、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、t-ブチル基又はCH3C(CH2CH3)2-から選ばれることを特徴とする請求項2~5のいずれか1項に記載のエトキシ/プロポキシ変性ピラゾリン有機物。
- (A)アルカリ可溶性重合体と、(B)エチレン性不飽和二重結合を有する化合物と、(C)第1の増感剤と、(D)光開始剤及び/又は第2の増感剤と、(E)その他の任意の助剤と、を含み、前記第1の増感剤が請求項1~7のいずれか1項に記載のエトキシ/プロポキシ変性ピラゾリン有機物であり、前記第2の増感剤が前記第1の増感剤と異なることを特徴とする光硬化性組成物。
- 前記アルカリ可溶性重合体は、(メタ)アクリル系重合体、スチレン系重合体、エポキシ系重合体、脂肪族ウレタン(メタ)アクリレート重合体、芳香族ウレタン(メタ)アクリレート重合体、アミド系樹脂、アミドエポキシ系樹脂、アルキッド系樹脂及びフェノール系樹脂からなる群より選ばれる1種又は2種以上であることを特徴とする請求項8に記載の光硬化性組成物。
- 前記エチレン性不飽和二重結合を有する化合物は、α,β-不飽和カルボン酸と多価アルコールとを反応させて得られる化合物、ビスフェノールA系(メタ)アクリレート化合物、α,β-不飽和カルボン酸とグリシジル基含有化合物とを反応させて得られる化合物、分子内にウレタン結合を有する(メタ)アクリレート化合物、ノニルフェノキシポリエチレンオキシアクリレート、γ-クロロ-β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、β-ヒドロキシエチル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-o-フタレート、フタル酸系化合物、アルキル(メタ)アクリレートからなる群より選ばれる1種又は2種以上であることを特徴とする請求項9に記載の光硬化性組成物。
- 前記助剤は、水素供与体、染料、顔料、光発色剤、充填剤、可塑剤、安定化剤、塗布助剤及び剥離促進剤からなる群より選ばれる1種又は2種以上であることを特徴とする請求項9又は10に記載の光硬化性組成物。
- 請求項1~7のいずれか1項に記載のエトキシ/プロポキシ変性ピラゾリン有機物の、光硬化分野への使用。
- 請求項8~11のいずれか1項に記載の光硬化性組成物を含むことを特徴とするフォトレジスト。
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