JP7290150B2 - 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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- JP7290150B2 JP7290150B2 JP2020513172A JP2020513172A JP7290150B2 JP 7290150 B2 JP7290150 B2 JP 7290150B2 JP 2020513172 A JP2020513172 A JP 2020513172A JP 2020513172 A JP2020513172 A JP 2020513172A JP 7290150 B2 JP7290150 B2 JP 7290150B2
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- 239000000047 product Substances 0.000 title claims description 56
- 239000011342 resin composition Substances 0.000 title claims description 53
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- 239000011347 resin Substances 0.000 title claims description 50
- 239000000463 material Substances 0.000 title claims description 14
- 229910000679 solder Inorganic materials 0.000 title claims description 11
- 239000011810 insulating material Substances 0.000 title claims description 5
- -1 acrylate compound Chemical class 0.000 claims description 189
- 150000001875 compounds Chemical class 0.000 claims description 117
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- 239000004925 Acrylic resin Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000001931 aliphatic group Chemical group 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 239000003999 initiator Substances 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 238000006845 Michael addition reaction Methods 0.000 claims description 18
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 14
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical group NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
- 230000009257 reactivity Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 82
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 43
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- 125000000217 alkyl group Chemical group 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 20
- 238000001723 curing Methods 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 206010034972 Photosensitivity reaction Diseases 0.000 description 16
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 239000003795 chemical substances by application Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000007809 chemical reaction catalyst Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 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 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 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 9
- 238000001035 drying Methods 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 150000002763 monocarboxylic acids Chemical class 0.000 description 9
- 125000004193 piperazinyl group Chemical group 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000010943 off-gassing Methods 0.000 description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 7
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- 239000002904 solvent 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
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
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- 150000001346 alkyl aryl ethers Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
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- 150000002596 lactones Chemical class 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000006353 oxyethylene group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 4
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- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 150000003512 tertiary amines Chemical class 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
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- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 3
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-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
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 3
- SVNWKKJQEFIURY-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1C SVNWKKJQEFIURY-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 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
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 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
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 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
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- 238000012360 testing method Methods 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 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
- 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
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-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
- 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
- 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
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
-
- 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
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Polymerisation Methods In General (AREA)
Description
R1は脂肪族基またはアリール基を表し、
R2及びR3はそれぞれ独立して脂肪族基またはアリール基を表し、
またR2とR3とはそれぞれ一体となって環を形成してもよく、
R4~R7はそれぞれ独立して水素原子、脂肪族基またはアリール基を表し、
X1は単結合または炭素原子数1~6の直鎖状若しくは分岐状のアルキレン基を表し、
X2はカルボニル基またはチオカルボニル基を表し、
Y1は下記一般式(2)、下記一般式(3)または下記一般式(4)で表される基を表し、
Y2は下記一般式(2)または下記一般式(3)で表される基を表す。但し、Y1及びY2が共に下記一般式(2)で表される構造を有する場合は、その少なくとも一方のX5は-NH-である。
nは、0または1である。)
R1は脂肪族基またはアリール基を表し、
R2及びR3はそれぞれ独立して脂肪族基またはアリール基を表し、
またR2とR3とはそれぞれ一体となって環を形成してもよく、
R4~R7はそれぞれ独立して水素原子、脂肪族基またはアリール基を表し、
X1は単結合または炭素原子数1~6の直鎖状若しくは分岐状のアルキレン基を表し、
X2はカルボニル基またはチオカルボニル基を表し、
Y1は下記一般式(2)、下記一般式(3)または下記一般式(4)で表される基を表し、
Y2は下記一般式(2)または下記一般式(3)で表される基を表す。但し、Y1及びY2が共に下記一般式(2)で表される構造を有する場合は、その少なくとも一方のX5は-NH-である。
nは、0または1である。)
前記α-アミノアセトフェノン骨格含有化合物(b1)は、ピペラジニル基、メチルアミノ基、エチルアミノ基、ベンジルアミノ基等の二級アミノ基に代表されるマイケル付加供与機能を有する官能基を分子構造中に持つものであり、具体的には、下記一般式(1)で表される。
R1は脂肪族基またはアリール基を表し、
R2~R3はそれぞれ独立して脂肪族基またはアリール基を表し、
またR2とR3とはそれぞれ一体となって環を形成してもよく、
R4~R7はそれぞれ独立して水素原子または脂肪族基またはアリール基を表し、
X1は単結合または炭素原子数1~6の直鎖状若しくは分岐状のアルキレン基を表し、
X2はカルボニル基、チオカルボニル基を表し、
Y1は下記一般式(2)、一般式(3)または一般式(4)で表される基を表し、
Y2は下記一般式(2)または一般式(3)で表される基を表す。但し、Y1及びY2が共に一般式(2)で表される構造を有する場合は、その少なくとも一方のX5は-NH-である。
nは、0または1である。)
方法1は、芳香核上にハロゲン原子を持つアルキルアセトフェノンを、2級アミノ基含有化合物(Y1-H)と反応させ、次いでカルボニル基のα位に臭素原子を導入し、次いで、2級モノアミン化合物(HN(R2)(R3))を反応させ、次いで、置換基(-X1-X2-OR)nを芳香核上の置換基として有するベンジルブロミドを反応させる。ここで、Rはアルキル基であり、nは0または1である。次いで、これをアルカリで処理して末端に水酸基(またはチオール基)を持つ中間体である化合物(P)を製造する。更に、これに2級アミノ基含有化合物(Y2-H)を反応させ、目的とするα-アミノアセトフェノン骨格含有化合物(b1)を製造することができる。この際、中間体である化合物(P)と2級アミノ基含有化合物(Y2-H)との反応において、2級アミノ基含有化合物(Y2-H)が活性水素を持つジアミン化合物である場合には、該化合物の一方のアミノ基を、オキシカルボニル基等で保護した化合物を用い、次いで、酸で処理して保護基を除去する方法を用いてもよい。
前記マイケル受容体としての機能を有する反応性化合物(b2)としては、光照射により硬化に寄与する反応性基(以下、「光硬化性基」と略記する。)を有する化合物をいい、前記光硬化性基を複数有する多官能性の反応性化合物が、光硬化機能が特に良好となることから、好ましい。
本発明において、前記α-アミノアセトフェノン骨格含有化合物(b1)と、前記マイケル受容体としての機能を有する反応性化合物(b2)とのマイケル付加反応は、特に限定されることなく、公知慣用の反応条件で行うことができる。一般的な方法としては、前記α-アミノアセトフェノン骨格含有化合物(b1)と前記マイケル受容体としての機能を有する反応性化合物(b2)とを、反応容器中、0~150℃で混合する方法が挙げられる。この際、触媒や有機溶媒を使用することもできる。
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(A-1)を得た。この酸基含有(メタ)アクリレート樹脂(A-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。
光重合開始剤(M18)は、特表2008-519760号公報の実施例3に記載の化合物5の合成例に従って合成し、下記構造式で表されるマイケル付加反応物(M18)を得た。
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(M17)8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(M17)を、表1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)~(5)を得た。
実施例1で用いた光重合開始剤(M17)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1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(M17)8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(6)を得た。
実施例6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(M17)を、表2に示した組成に代えた以外は、実施例6と同様にして感光性樹脂組成物(7)~(10)を得た。
実施例6で用いた光重合開始剤(M17)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2に示した配合量で用いた以外は、実施例6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 (5)
- 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)で表されるマイケル付加供与体として機能するα-アミノアセトフェノン骨格含有化合物(b1)と、マイケル受容体としての機能を有する反応性化合物(b2)とのマイケル付加反応物であり、
前記マイケル受容体としての機能を有する反応性化合物(b2)が、多官能型(メタ)アクリレート化合物であり、
前記マイケル付加反応物が下記一般式(1)で表されるマイケル付加供与体として機能するα-アミノアセトフェノン骨格含有化合物(b1)由来の構造を1種とマイケル受容体としての機能を有する反応性化合物(b2)由来の構造を1種又は2種有することを特徴とする感光性樹脂組成物。
R1は脂肪族基またはアリール基を表し、
R2及びR3はそれぞれ独立して脂肪族基またはアリール基を表し、
またR2とR3とはそれぞれ一体となって環を形成してもよく、
R4~R7はそれぞれ独立して水素原子、脂肪族基またはアリール基を表し、
X1は単結合または炭素原子数1~6の直鎖状若しくは分岐状のアルキレン基を表し、
X2はカルボニル基またはチオカルボニル基を表し、
Y1は下記一般式(2)、下記一般式(3)または下記一般式(4)で表される基を表し、
Y2は下記一般式(2)または下記一般式(3)で表される基を表す。但し、Y1及びY2が共に下記一般式(2)で表される構造を有する場合は、その少なくとも一方のX5は-NH-である。
nは、0または1である。)
- 請求項1記載の感光性樹脂組成物の硬化反応物であることを特徴とする硬化物。
- 請求項1または2記載の感光性樹脂組成物からなることを特徴とする絶縁材料。
- 請求項1または2記載の感光性樹脂組成物からなることを特徴とするソルダーレジスト用樹脂材料。
- 請求項4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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