JP7310802B2 - 感光性樹脂組成物、硬化物、絶縁材料、ソルダーレジスト用樹脂材料及びレジスト部材 - Google Patents
感光性樹脂組成物、硬化物、絶縁材料、ソルダーレジスト用樹脂材料及びレジスト部材 Download PDFInfo
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- JP7310802B2 JP7310802B2 JP2020513173A JP2020513173A JP7310802B2 JP 7310802 B2 JP7310802 B2 JP 7310802B2 JP 2020513173 A JP2020513173 A JP 2020513173A JP 2020513173 A JP2020513173 A JP 2020513173A JP 7310802 B2 JP7310802 B2 JP 7310802B2
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- 239000000047 product Substances 0.000 title claims description 64
- 239000011342 resin composition Substances 0.000 title claims description 55
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 192
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- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 239000004925 Acrylic resin Substances 0.000 claims description 64
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 239000003999 initiator Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
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- 239000007795 chemical reaction product Substances 0.000 claims description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 90
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
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- 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 14
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 150000003335 secondary amines Chemical class 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
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- 239000007809 chemical reaction catalyst Substances 0.000 description 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- NLWBJPPMPLPZIE-UHFFFAOYSA-N methyl 4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1 NLWBJPPMPLPZIE-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- HYSQEYLBJYFNMH-UHFFFAOYSA-N n'-(2-aminoethyl)-n'-methylethane-1,2-diamine Chemical compound NCCN(C)CCN HYSQEYLBJYFNMH-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- PYNVYLAZKQQFLK-UHFFFAOYSA-N naphthalene-1,2,3,4-tetrol Chemical compound C1=CC=CC2=C(O)C(O)=C(O)C(O)=C21 PYNVYLAZKQQFLK-UHFFFAOYSA-N 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical compound C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000000016 photochemical curing Methods 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
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 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
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical group COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Chemical group COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
- UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- BCMKHWMDTMUUSI-UHFFFAOYSA-N tetrahydroxynaphthalene Natural products OC1=CC(O)=CC2=CC(O)=CC(O)=C21 BCMKHWMDTMUUSI-UHFFFAOYSA-N 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
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 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
Classifications
-
- 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
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
R1は炭素原子数1~10のアルキル基を表し、
R2は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、炭素原子数1または2のアルコキシ基で置換された炭素原子数2~4のアルキル基のいずれかを表し、
R3は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、メトキシエチル基、またはエトキシエチル基を表し、
またR2とR3とが一体となって窒素原子と共に環構造を形成するアルキレン基、R2とR3とが一体となって窒素原子と共にモルホリン骨格、N-メチルピペラジン骨格、または2,6-ジメチルモルホリン骨格を形成する環構形成部位であってもよく、
R4~R7は、それぞれ独立して水素原子、炭素原子数1~8のアルキル基、またはフェニル基を表し、
Y1は、置換基を有しないか、またはハロゲン原子若しくは水酸基を置換基として有する炭素原子数3~19のアルキル基(y1-1)、炭素原子数7~19のアラルキル基(y1-2)、または下記構造式(y1-3)で表される構造部位(y1-3)、
R1は炭素原子数1~10のアルキル基を表し、
R2は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、炭素原子数1または2のアルコキシ基で置換された炭素原子数2~4のアルキル基のいずれかを表し、
R3は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、メトキシエチル基、またはエトキシエチル基を表し、
またR2とR3とが一体となって窒素原子と共に環構造を形成するアルキレン基、R2とR3とが一体となって窒素原子と共にモルホリン骨格、N-メチルピペラジン骨格、または2,6-ジメチルモルホリン骨格を形成する環構形成部位であってもよく、
R4~R7は、それぞれ独立して水素原子、炭素原子数1~8のアルキル基、またはフェニル基を表し、
Y1は、置換基を有しないか、またはハロゲン原子若しくは水酸基を置換基として有する炭素原子数3~19のアルキル基(y1-1)、炭素原子数7~19のアラルキル基(y1-2)、または下記構造式(y1-3)で表される構造部位(y1-3)、
メトキシエチル基;エトキシエチル基;R2及びR3が一体となって窒素原子と共に環構造を形成するアルキレン基、即ち
イソプロピル基、n-ブチル基、イソブチル基、t-ブチル基、s-ブチル基、ペンチル基、ヘキシル基、2-エチルブチル基、イソペンチル基、1-メチルペンチル基、1,3-ジメチルブチル基等が挙げられ、ハロゲン原子としては、臭素原子、塩素原子、フッ素原子が挙げられる。
ハロゲン化ベンゼンと、α位にハライド原子を有する酸ハライド化合物とを反応させて、カルボニルのα炭素原子上にハロゲン原子を持つアルキルアセトフェノン誘導体を合成する。[工程I]の反応は無水塩化アルミの存在下でフリーデルクラフト-アシル化反応によって行うことができる。 ここで、前記ハロゲン化ベンゼンとしては、フッ化ベンゼン、クロロベンゼン、ブロモベンゼン等が挙げられる。また、前記したα位にハライド原子を有する酸ハライド化合物としては、 2-ブロモプロピオン酸ブロミド、2-ブロモプロピオン酸クロリド、2-ブロモ吉草酸ブロミド、2-ブロモ吉草酸クロリド、2-ブロモヘキサン酸ブロミド、2-ブロモオクタン酸ブロミド等が挙げられる。
次いで、2級モノアミン化合物(HN(R2)(R3))を反応させてα位をアミノ基に変換する。ここで使用する2級モノアミン化合物(HN(R2)(R3))としては、ジメチルアミン、ジエチルアミン、メチルブチルアミン、メチルオクチルアミン、メチルドデシルアミン、エチルヘキシルアミン、ジエタノールアミン、ジイソプロパノールアミン、ジイソブタノールアミン、2,2’-ジエトキシジエチルアミン、2,2’-ジメトキシジエチルアミン、モルホリン、ピロリジン、ピペリジン、N-メチルピペラジン、2,6-ジメチルモルホリン等が挙げられる。反応条件は、例えば炭酸カルシウム、炭酸カリウム、炭酸ナトリウム等の炭酸塩や、トリエチルアミン、ジイソプロピルエチルアミン等の三級アミン等の塩基の存在下、0℃~80℃の温度条件にて行うことができる。また、2級アミンを塩基として作用させる場合には過剰量用いて製造することができる。
次いで、置換基(-Y3-C(=O)-OR)を芳香核上の置換基として有するベンジルブロミド(ここで、Rはアルキル基または水素原子である)をアセトフェノン誘導体の三級アミンに反応させて四級アンモニウム塩に導き、その後、アルカリ処理によって、1.2-転位反応(スティーブンス転移)を行い、一般式3で表されるα―アミノアセトフェノン中間体化合物A(一般式3)を合成する。こうして得られたα―アミノアセトフェノン中間化合物(一般式3)はアセトフェノン部の芳香環上にハロゲン原子を有し、かつ、α位に置換したベンジル基の芳香環上にカルボキシル基を有するものとなる。
次に、前記α―アミノアセトフェノン中間化合物(一般式3)のカルボキシル基と二官能以上の1級または2級アミンまたは二官能以上のアルコール(一般式4)を縮合反応させ、それぞれポリアミド化合物およびポリエステル化合物である中間体化合物Bへ誘導する。
その後、中間体化合物Bの分子の末端部分のアリールハロゲン部を、一般式5で表される二官能性の環状アミンで置換して、分子の末端が二級アミンである中間生成物Cを合成する。
次いで、最終の反応として、[工程V]で得られた中間体化合物Cの構造末端に位置する二級アミンに対して、(メタ)アクリル酸エステル化合物化合物、イソシアン酸エステル、グリシジルエーテル、又はアルキルハライドと反応させることにより前記一般式(1)で表される化合物を製造することができる。具体的には、[工程VI]は、中間体化合物Cに反応させる化合物により以下の(工程VI-1)~(工程VI-9)に分類することができる。
前記中間体化合物C中の構造末端に位置する二級アミンに対して、下記反応式中、Hal-R’で表される、炭素原子数3~18のハロゲン化アルカンを反応させることにより(なお、該アルカンは反応に関与しないハロゲン原子又は水酸基を有していてもよい。)、Y1が、置換基を有しないか、又はハロゲン原子若しくは水酸基を置換基として有する炭素原子数3~18のアルキル基(y1-1)である、下記一般式1-1で表される化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記反応式中、Hal-Aralで表されるハロゲン化芳香族化合物と反応させることにより、Y1が、アラルキル基(y1-2)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-3r)で表されるハロゲン化ポリエーテル化合物と反応させることにより、Y1が、構造式(y1-3)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-4r)で表される化合物の(メタ)アクリロイル基とマイケル付加反応させることにより、前記一般式(1)中のY1が、構造式(y1-4)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-5r)で表される化合物の(メタ)アクリロイル基と反応させることにより、前記一般式(1)中のY1が、構造式(y1-5)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-6r)で表されるエポキシ化合物のエポキシ基と反応させることにより、Y1が、構造式(y1-6)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-7r)で表されるエポキシ化合物のエポキシ基と反応させることにより、Y1が、構造式(y1-7)である化合物を製造することができる。
前記中間体化合物C中の構造末端に位置する二級アミンを、下記構造式(y1-9r)で表されるイソシアネート化合物のイソシアネート基と反応させることにより、Y1が、構造式(y1-9)である化合物を製造することができる。
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ジエチレングリコールモノメチルエーテルアセテート101質量部を入れ、オルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」、エポキシ当量;214g/eq)428質量部を溶解し、酸化防止剤としてジブチルヒドロキシトルエン4質量部、熱重合禁止剤としてメトキノン0.4質量部加えた後、アクリル酸144質量部、トリフェニルホスフィン1.6質量部を添加し、空気を吹き込みながら120℃で10時間エステル化反応を行なった。その後、ジエチレングリコールモノメチルエーテルアセテート311質量部、テトラヒドロ無水フタル酸160質量部を加え110℃で2.5時間反応させて、酸基含有(メタ)アクリレート樹脂(1)を得た。この酸基含有(メタ)アクリレート樹脂(1)の固形分酸価は85mgKOH/gであった。
温度計、攪拌器、及び還流冷却器を備えたフラスコに、ジエチレングリコールモノメチルエーテルアセテート379質量部、イソホロンジイソシアネートのイソシアヌレート変性体(EVONIK社製「VESTANAT T-1890/100」、イソシアネート基含有量17.2質量%)185質量部、無水トリメリット酸146質量部、ジブチルヒドロキシトルエン1.6質量部を加えて溶解させた。窒素雰囲気下、160℃で5時間反応させ、イソシアネート基含有量が0.1質量%以下となっていることを確認した。次いで、メトキノン0.3質量部、ペンタエリスリトールポリアクリレート混合物(東亜合成株式会社製「アロニックスM-306」、ペンタエリスリトールトリアクリレート含有量約67%、水酸基価159.7mgKOH/g)112質量部及びトリフェニルホスフィン3.1質量部を添加し、空気を吹き込みながら110℃で5時間反応させた。次いで、グリシジルメタクリレート125質量部を添加し、110℃で5時間反応させた。更に、無水コハク酸87質量部を加えて110℃で5時間反応させて、酸基含有(メタ)アクリレート樹脂(A-2)を得た。この酸基含有(メタ)アクリレート樹脂(A-2)の固形分酸価は80mgKOH/gであった。
合成例1で得た酸基含有(メタ)アクリレート樹脂(A-1)100質量部、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」)24.6質量部、ジペンタエリスリトールヘキサアクリレート6.3質量部、合成例3で得た光重合開始剤(M31)10質量部、ジエチレングリコールモノメチルエーテルアセテート13.3質量部、2-エチル-4-メチルイミダゾール0.5質量部、フタロシアニングリーン0.7質量部を配合し、ロールミルにより混錬して感光性樹脂組成物(1)を得た。
実施例1で用いた酸基含有(メタ)アクリレート樹脂(A-1)及び光重合開始剤(M31)を、表13に示した組成に代えた以外は、実施例1と同様にして感光性樹脂組成物(2)及び(3)を得た。
実施例1で用いた光重合開始剤(M31)の代わりに、2-メチル-1-(4-メチルチオフェニル)-2-モルフォリノプロパン-1-オン(IGM社製「Omnirad907」)、または2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-1-ブタノン(IGM社製「Omnirad369」)を表13に示した配合量で用いた以外は、実施例1と同様にして感光性樹脂組成物(C1)及び(C2)を得た。
各実施例及び比較例で得られた感光性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布し、80℃で30分乾燥させた。次いで、乾燥させた塗膜上にコダック社製「ステップタブレットNo.2」を乗せ、メタルハライドランプを用いて500mJ/cm2の紫外線を照射した。これを1%の炭酸ナトリウム水溶液で30℃180秒間現像し、ステップタブレット法に基づきステップタブレットの残存段数にて評価した。なお、残存段数が多いほど光感度が高いことを示す。
各実施例及び比較例で得られた感光性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布した後、80℃でそれぞれ30分間、40分間、50分間、60分間、70分間、80分間、90分間、100分間乾燥させ、乾燥時間が異なるサンプルを作成した。これらを1%炭酸ナトリウム水溶液で30℃180秒間現像し、基板上に残渣が残らなかったサンプルの80℃での乾燥時間を乾燥管理幅として下記の評価基準で評価した。なお、乾燥管理幅が長いほどアルカリ現像性が優れていることを示す。
×:乾燥管理幅が、60分未満であった。
合成例1で得た酸基含有(メタ)アクリレート樹脂(A-1)100質量部、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N-680」)24.6質量部、合成例3で得た光重合開始剤(M31)10質量部、ジエチレングリコールモノメチルエーテルアセテート13.3質量部を配合して感光性樹脂組成物(4)を得た。
実施例4で用いた酸基含有(メタ)アクリレート樹脂(A-1)及び光重合開始剤(M31)を、表14に示した組成に代えた以外は、実施例4と同様にして感光性樹脂組成物(5)及び(6)を得た。
実施例4で用いた光重合開始剤(M31)の代わりに、2-メチル-1-(4-メチルチオフェニル)-2-モルフォリノプロパン-1-オン(IGM社製「Omnirad907」)、または2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-1-ブタノン(IGM社製「Omnirad369」)を表14に示した配合量で用いた以外は、実施例4と同様にして感光性樹脂組成物(C3)及び(C4)を得た。
各実施例及び比較例で得られた感光性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布し、80℃で30分乾燥させた。次いで、メタルハライドランプを用いて500mJ/cm2の紫外線を照射した後、200℃で1時間加熱して、硬化物をガラス基材から剥離し、硬化物を得た。前記硬化物から6mm×35mmの試験片を切り出し、粘弾性測定装置(DMA:レオメトリック社製固体粘弾性測定装置「RSAII」、引張り法:周波数1Hz、昇温速度3℃/分)を用いて、弾性率変化が最大となる温度をガラス転移温度として評価した。なお、ガラス転移温度が高いほど耐熱性に優れていることを示す。
各実施例及び比較例で得られた感光性樹脂組成物を、アプリケーターを用いてガラス基材上に膜厚50μmとなるように塗布し、80℃で30分乾燥させた。次いで、メタルハライドランプを用いて500mJ/cm2の紫外線を照射した後、200℃で1時間加熱して、硬化物をガラス基材から剥離し、硬化物を得た。前記硬化物より粉末サンプルを採取し、ゲステル社製加熱脱着装置(TDU)に入れた。その後(1)150℃の熱抽出温度で10分間アウトガス成分を、(2)260℃の熱抽出温度で10分間アウトガス成分を、それぞれ液体窒素を用いて-60℃で捕集した。捕集したアウトガス成分は、アジレントテクノロジー社製ガスクロマトグラフィー質量分析装置(6890N/5973N)で分離分析を行い、n-ドデカン換算で定量し、以下の評価基準で評価した。
○:アウトガス成分が少し確認された。
△:アウトガス成分が確認された。
×:多量のアウトガス成分が確認された。
Claims (4)
- 酸基含有(メタ)アクリレート樹脂(A)と、光重合開始剤(B)とを含有する感光性樹脂組成物の硬化反応物からなる硬化物であって、
前記光重合開始剤(B)が、下記一般式(1)で表される化合物であることを特徴とする感光性樹脂組成物の硬化反応物からなる硬化物。
R1は炭素原子数1~10のアルキル基を表し、
R2は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、炭素原子数1または2のアルコキシ基で置換された炭素原子数2~4のアルキル基のいずれかを表し、
R3は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、メトキシエチル基、またはエトキシエチル基を表し、
R4~R7は、それぞれ独立して水素原子、炭素原子数1~8のアルキル基、またはフェニル基を表し、
Y1は、下記構造式(y1-8)で表される構造部位(y1-8)
X1はエチレン基を、X2及びX3が破線部にて共有結合を形成しつつ一体的にエチレン基を表し、Y2は、下記構造式
で表される構造部位(y2-3)であり、
Y3は、単結合、炭素原子数1~3のアルキレン基、又は炭素原子数1~3のアルキリデン基を表し、かつ、nは1を表す。] - 酸基含有(メタ)アクリレート樹脂(A)と、光重合開始剤(B)とを含有する感光性樹脂組成物からなる絶縁材料であって、
前記光重合開始剤(B)が、下記一般式(1)で表される化合物であることを特徴とする感光性樹脂組成物からなる絶縁材料。
R1は炭素原子数1~10のアルキル基を表し、
R2は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、炭素原子数1または2のアルコキシ基で置換された炭素原子数2~4のアルキル基のいずれかを表し、
R3は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、メトキシエチル基、またはエトキシエチル基を表し、
R4~R7は、それぞれ独立して水素原子、炭素原子数1~8のアルキル基、またはフェニル基を表し、
Y1は、下記構造式(y1-8)で表される構造部位(y1-8)
X1はエチレン基を、X2及びX3が破線部にて共有結合を形成しつつ一体的にエチレン基を表し、Y2は、下記構造式
で表される構造部位(y2-3)であり、
Y3は、単結合、炭素原子数1~3のアルキレン基、又は炭素原子数1~3のアルキリデン基を表し、かつ、nは1を表す。] - 酸基含有(メタ)アクリレート樹脂(A)と、光重合開始剤(B)とを含有する感光性樹脂組成物からなるソルダーレジスト用樹脂材料であって、
前記光重合開始剤(B)が、下記一般式(1)で表される化合物であることを特徴とする感光性樹脂組成物からなるソルダーレジスト用樹脂材料。
R1は炭素原子数1~10のアルキル基を表し、
R2は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、炭素原子数1または2のアルコキシ基で置換された炭素原子数2~4のアルキル基のいずれかを表し、
R3は炭素原子数1~12のアルキル基、炭素原子数2~4のヒドロキシアルキル基、メトキシエチル基、またはエトキシエチル基を表し、
R4~R7は、それぞれ独立して水素原子、炭素原子数1~8のアルキル基、またはフェニル基を表し、
Y1は、下記構造式(y1-8)で表される構造部位(y1-8)
X1はエチレン基を、X2及びX3が破線部にて共有結合を形成しつつ一体的にエチレン基を表し、Y2は、下記構造式
で表される構造部位(y2-3)であり、
Y3は、単結合、炭素原子数1~3のアルキレン基、又は炭素原子数1~3のアルキリデン基を表し、かつ、nは1を表す。] - 請求項3記載のソルダーレジスト用樹脂材料からなることを特徴とするレジスト部材。
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WO2016181784A1 (ja) * | 2015-05-13 | 2016-11-17 | Dic株式会社 | (メタ)アクリレート樹脂及び光学部材 |
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JP2005314634A (ja) | 2004-03-30 | 2005-11-10 | Dainippon Printing Co Ltd | 光ラジカル重合開始剤、感光性樹脂組成物及び、物品 |
WO2012023164A1 (ja) | 2010-08-20 | 2012-02-23 | 太陽油墨(蘇州)有限公司 | アルカリ現像型感光性樹脂組成物 |
WO2017195428A1 (ja) | 2016-05-13 | 2017-11-16 | Dic株式会社 | 新規化合物、光硬化性組成物、その硬化物、印刷インキ及び該印刷インキを用いた印刷物 |
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