JP7407714B2 - Reflow compatible dicing tape - Google Patents
Reflow compatible dicing tape Download PDFInfo
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- JP7407714B2 JP7407714B2 JP2020537799A JP2020537799A JP7407714B2 JP 7407714 B2 JP7407714 B2 JP 7407714B2 JP 2020537799 A JP2020537799 A JP 2020537799A JP 2020537799 A JP2020537799 A JP 2020537799A JP 7407714 B2 JP7407714 B2 JP 7407714B2
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- 150000001875 compounds Chemical class 0.000 claims description 77
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 56
- -1 oxime ester compound Chemical class 0.000 claims description 56
- 239000012790 adhesive layer Substances 0.000 claims description 49
- 239000000853 adhesive Substances 0.000 claims description 39
- 230000001070 adhesive effect Effects 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 239000003999 initiator Substances 0.000 claims description 27
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 22
- 229910052710 silicon Inorganic materials 0.000 claims description 22
- 239000010703 silicon Substances 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 239000010410 layer Substances 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 230000005855 radiation Effects 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 253
- 125000000217 alkyl group Chemical group 0.000 description 107
- 125000005843 halogen group Chemical group 0.000 description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 75
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 72
- 125000000623 heterocyclic group Chemical group 0.000 description 70
- 125000003710 aryl alkyl group Chemical group 0.000 description 64
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 62
- 125000004093 cyano group Chemical group *C#N 0.000 description 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 46
- 125000003118 aryl group Chemical group 0.000 description 39
- 239000004593 Epoxy Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 23
- 150000001721 carbon Chemical group 0.000 description 22
- 150000002430 hydrocarbons Chemical group 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 125000002947 alkylene group Chemical group 0.000 description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
- 150000007519 polyprotic acids Polymers 0.000 description 14
- 125000004430 oxygen atom Chemical group O* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 229910052711 selenium Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 230000001678 irradiating effect Effects 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004696 Poly ether ether ketone Substances 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229920002530 polyetherether ketone Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229920006243 acrylic copolymer Polymers 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- 150000003855 acyl compounds Chemical class 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 229940049920 malate Drugs 0.000 description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004697 Polyetherimide Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
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- 239000005020 polyethylene terephthalate Substances 0.000 description 2
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- IYDQUNGWLDBKOF-UHFFFAOYSA-N 1-(4-butylphenyl)-2,2,2-trichloroethanone Chemical compound CCCCC1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IYDQUNGWLDBKOF-UHFFFAOYSA-N 0.000 description 1
- QPTNWCMSMODKOQ-UHFFFAOYSA-N 1-[9-butyl-6-(2-methyl-2-morpholin-4-ylpropanoyl)carbazol-3-yl]-2-methyl-2-morpholin-4-ylpropan-1-one Chemical compound C=1C=C2N(CCCC)C3=CC=C(C(=O)C(C)(C)N4CCOCC4)C=C3C2=CC=1C(=O)C(C)(C)N1CCOCC1 QPTNWCMSMODKOQ-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
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- 230000001771 impaired effect Effects 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 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
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
- H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Dicing (AREA)
Description
本発明は、半導体製造工程に使用するリフロー対応ダイシングテープに関する。 The present invention relates to a reflow compatible dicing tape used in semiconductor manufacturing processes.
近年、半導体の構造において性能向上に伴い、チップ及び電気的接続点の高密度化が進んでいる。以前は電気的接続にはワイヤーが用いられていたが、接続信頼性向上のために半田による接続が進んでおり、接続工程内に半田ボールを溶かす工程（リフロー工程）が用いられるようになっている。リフロー工程においては、チップに対して２００℃を超える高温がかけられるため、支持体となるダイシングテープにも、２００℃を超える高温に耐えうる耐熱性が必要とされる。 In recent years, as the performance of semiconductor structures has improved, the density of chips and electrical connection points has increased. In the past, wires were used for electrical connections, but in order to improve connection reliability, connections using solder are becoming more common, and a process of melting solder balls during the connection process (reflow process) has come to be used. There is. In the reflow process, a high temperature of over 200°C is applied to the chip, so the dicing tape that serves as a support also needs to have heat resistance that can withstand high temperatures of over 200°C.
２００℃を超える高温にも対応できるダイシングテープとして、例えば、特許文献１では、エネルギー線を照射して架橋反応を誘導することによって硬化された耐熱性を有する粘着剤層を用いたテープが開示されている。特許文献１のように、リフロー工程前にエネルギー線を照射して粘着剤層の樹脂成分を架橋反応させることで、被着体であるシリコンウエハの貼り合わせ面に、糊（粘着剤）が残ってしまう、いわゆる糊残りが改善できる。 As a dicing tape that can handle high temperatures exceeding 200°C, for example, Patent Document 1 discloses a tape using a heat-resistant adhesive layer that is cured by irradiating energy rays to induce a crosslinking reaction. ing. As in Patent Document 1, by irradiating the resin component of the adhesive layer with energy rays before the reflow process to cause a crosslinking reaction, no adhesive (adhesive) remains on the bonding surface of the silicon wafer, which is the adherend. It is possible to improve the so-called adhesive residue that can occur.
しかしながら、エネルギー線を照射して粘着剤層の樹脂成分を架橋反応させると、粘着剤層に含まれる光重合開始剤が分裂して低分子化し、アウトガスの原因となる。エネルギー線照射後にリフロー工程を経てシリコンウエハを個片化するダイシング工程を実施すると、粘着剤から発生したアウトガスによる浮きのため、チップを固定できずにダイシングテープから剥がれてしまうチップ飛びという不良が発生することがある。 However, when the resin component of the adhesive layer is subjected to a crosslinking reaction by irradiation with energy rays, the photopolymerization initiator contained in the adhesive layer is split and becomes low molecular weight, causing outgassing. When performing the dicing process to separate the silicon wafer into individual pieces through the reflow process after irradiation with energy rays, a defect called chip flying occurs where the chips cannot be fixed and come off from the dicing tape due to floating due to outgas generated from the adhesive. There are things to do.
上記から、リフロー工程を経たテープは、ダイシング工程の前にシリコンウエハから剥離されて、別のダイシング工程用テープがシリコンウエハに貼り合わされることも行われている。このようなテープの貼り替えは、スループットの悪化を招き、廃棄物も増えることから改善が望まれている。 From the above, the tape that has undergone the reflow process is sometimes peeled off from the silicon wafer before the dicing process, and another tape for the dicing process is bonded to the silicon wafer. Reapplying tapes like this causes a deterioration in throughput and increases waste, so improvements are desired.
本発明は、前記問題点に基づきなされたものであり、本発明の目的は、放射線硬化型粘着剤層からのアウトガスの発生を抑制して優れた耐汚染性を有するリフロー対応ダイシング用テープを提供することにある。 The present invention has been made based on the above-mentioned problems, and an object of the present invention is to provide a reflow-compatible dicing tape that suppresses the generation of outgas from a radiation-curable adhesive layer and has excellent contamination resistance. It's about doing.
本発明者は、上記目的を達成すべく、耐熱性粘着テープの物性、材料等について鋭意研究した。その結果、放射線硬化型粘着剤を含むテープであって、放射線硬化型粘着剤層に被着体であるシリコンウエハを貼りあわせた後に、放射線照射し、２１０℃、１０分の加熱処理後に、前記シリコンウエハを前記放射線硬化型粘着剤層から剥離させた際における前記シリコンウエハの貼り合わせ面をＸ線光電子分光法にて測定した際の炭素量が、３０ｍｏｌ％以下である放射線硬化型粘着剤層であれば、上記目的を達成できることを見出し、本発明を完成するに至った。 In order to achieve the above object, the present inventor has conducted extensive research on the physical properties, materials, etc. of heat-resistant adhesive tapes. As a result, a tape containing a radiation-curable adhesive was obtained, in which a silicon wafer as an adherend was bonded to the radiation-curable adhesive layer, and then irradiated with radiation and heat-treated at 210°C for 10 minutes. A radiation-curable adhesive layer having a carbon content of 30 mol% or less when the bonded surface of the silicon wafer is measured by X-ray photoelectron spectroscopy when the silicon wafer is peeled from the radiation-curable adhesive layer. The present inventors have discovered that the above object can be achieved if this is the case, and have completed the present invention.
本発明の構成の要旨は、以下の通りである。
［１］基材層と該基材層上に設けられた放射線硬化型粘着剤層を備え、
前記放射線硬化型粘着剤層にシリコンウエハを貼りあわせた後に、放射線照射してから２１０℃にて１０分の加熱処理をし、該加熱処理後に前記放射線硬化型粘着剤層から前記シリコンウエハを剥離させた際における前記シリコンウエハの貼り合わせ面をＸ線光電子分光法にて測定した際の炭素量が、３０ｍｏｌ％以下であるリフロー対応ダイシングテープ。
［２］前記放射線硬化型粘着剤層が、エチレン性不飽和結合を有する重合性化合物、該エチレン性不飽和結合を有する重合性化合物の重合体並びに／またはカチオン及び／若しくはアニオンと反応する環状構造を有する化合物と、光重合開始剤と、を含む［１］に記載のリフロー対応ダイシングテープ。
［３］前記エチレン性不飽和結合を有する重合性化合物の重合体が、（メタ）アクリル酸及び／または（メタ）アクリレートを含むモノマーの重合体である（メタ）アクリル系重合体を含む［２］に記載のリフロー対応ダイシングテープ。
［４］前記光重合開始剤が、オキシムエステル化合物である［２］または［３］に記載のリフロー対応ダイシングテープ。
［５］前記光重合開始剤の分子量が、４００以上である［２］乃至［４］のいずれか１つに記載のリフロー対応ダイシングテープ。
［６］前記放射線硬化型粘着剤層が、紫外線硬化型粘着剤層である［１］乃至［５］のいずれか１つに記載のリフロー対応ダイシングテープ。
［７］前記放射線硬化型粘着剤層の、波長３５０ｎｍの放射線を１０００ｍJ／ｃｍ２照射してから２１０℃にて１０分の加熱処理をした後の、ＪＩＳ Ｚ０２３７に準拠して測定した粘着力が、０．３Ｎ／２５ｍｍ幅以上２．０Ｎ／２５ｍｍ幅以下である［１］乃至［６］のいずれか１つに記載のリフロー対応ダイシングテープ。The gist of the configuration of the present invention is as follows.
[1] Comprising a base layer and a radiation-curable adhesive layer provided on the base layer,
After bonding the silicon wafer to the radiation-curable adhesive layer, heat treatment is performed at 210° C. for 10 minutes after irradiation with radiation, and after the heat treatment, the silicon wafer is peeled from the radiation-curable adhesive layer. A reflow compatible dicing tape having a carbon content of 30 mol% or less when the bonded surface of the silicon wafer is measured by X-ray photoelectron spectroscopy.
[2] The radiation-curable adhesive layer has a cyclic structure that reacts with a polymerizable compound having an ethylenically unsaturated bond, a polymer of the polymerizable compound having an ethylenically unsaturated bond, and/or a cation and/or anion. The reflow compatible dicing tape according to [1], comprising a compound having the following: and a photopolymerization initiator.
[3] The polymer of the polymerizable compound having an ethylenically unsaturated bond includes a (meth)acrylic polymer that is a polymer of a monomer containing (meth)acrylic acid and/or (meth)acrylate [2] ] Reflow compatible dicing tape.
[4] The reflow compatible dicing tape according to [2] or [3], wherein the photopolymerization initiator is an oxime ester compound.
[5] The reflow compatible dicing tape according to any one of [2] to [4], wherein the photopolymerization initiator has a molecular weight of 400 or more.
[6] The reflow-compatible dicing tape according to any one of [1] to [5], wherein the radiation-curable adhesive layer is an ultraviolet-curable adhesive layer.
[7] The adhesive strength of the radiation-curable adhesive layer measured in accordance with JIS Z0237 after irradiation with 1000 mJ/ cm2 of radiation with a wavelength of 350 nm and heat treatment at 210°C for 10 minutes is , the reflow compatible dicing tape according to any one of [1] to [6], which has a width of 0.3 N/25 mm or more and 2.0 N/25 mm width or less.
本発明では、リフロー工程前にシリコンウエハに貼り合わされているダイシングテープの放射線硬化型粘着剤層に、予め放射線を照射することにより、該放射線硬化型粘着剤層を構成する主成分の分子量は架橋反応等により上昇する。ダイシングテープ中に低分子成分が含まれていても、放射線硬化型粘着剤層を構成する主成分の分子量上昇の際に、該低分子成分は主骨格に取り込まれて揮発成分を減らすことができる。従って、本発明のリフロー対応ダイシングテープでは、アウトガス成分を低減することができる。 In the present invention, by irradiating the radiation-curable adhesive layer of the dicing tape bonded to the silicon wafer with radiation in advance before the reflow process, the molecular weight of the main component constituting the radiation-curable adhesive layer is reduced by crosslinking. Increases due to reactions, etc. Even if the dicing tape contains low-molecular components, when the molecular weight of the main components constituting the radiation-curable adhesive layer increases, the low-molecular components are incorporated into the main skeleton and can reduce volatile components. . Therefore, in the reflow compatible dicing tape of the present invention, outgas components can be reduced.
本発明の態様によれば、リフロー工程後にてシリコンウエハをダイシングテープから剥離する際に、放射線硬化型粘着剤層の粘着剤がシリコンウエハに残存する、いわゆる糊残りを防止できつつ、放射線硬化型粘着剤層からのアウトガスの発生によるシリコンウエハのダイシングテープからの浮きも防止できることから、チップ飛びを防止することができる。 According to an aspect of the present invention, when the silicon wafer is peeled off from the dicing tape after the reflow process, it is possible to prevent the adhesive of the radiation-curable adhesive layer from remaining on the silicon wafer, that is, so-called adhesive residue; Since it is also possible to prevent the silicon wafer from floating from the dicing tape due to the generation of outgas from the adhesive layer, chip flying can be prevented.
本発明のリフロー対応ダイシングテープについて、以下に説明する。本発明のリフロー対応ダイシングテープは、基材層と該基材層上に設けられた放射線硬化型粘着剤層を備える。放射線硬化型粘着剤層は、基材層上に放射線硬化型粘着剤を塗工することで形成することができる。 The reflow compatible dicing tape of the present invention will be explained below. The reflow compatible dicing tape of the present invention includes a base layer and a radiation-curable adhesive layer provided on the base layer. The radiation-curable adhesive layer can be formed by coating a radiation-curable adhesive on the base layer.
本発明のリフロー対応ダイシングテープの放射線硬化型粘着剤層は、波長３５０ｎｍの放射線を１０００ｍＪ／ｃｍ２照射してから２１０℃にて１０分の加熱処理をした後の、ＪＩＳ Ｚ０２３７に準拠して測定した粘着力は、特に限定されないが、その下限値は、ダイシング工程中にチップを固定できずチップが飛んでしまういわゆるチップ飛びや、搬送を含む工程中で剥離することを確実に防止する点から、０．３Ｎ／２５ｍｍ幅以上が好ましく、０．５Ｎ／２５ｍｍ幅以上が特に好ましい。また、上記粘着力の上限値は、リフロー対応ダイシングテープの剥離の際に被着体上に放射線硬化型粘着剤層の一部が付着する、いわゆる糊残りを確実に防止する点から、２．０Ｎ／２５ｍｍ以下が好ましく、１．５Ｎ／２５ｍｍ幅以下が特に好ましい。The radiation-curable adhesive layer of the reflow compatible dicing tape of the present invention was measured in accordance with JIS Z0237 after being irradiated with 1000 mJ/ cm2 of radiation with a wavelength of 350 nm and then heat-treated at 210°C for 10 minutes. The adhesive strength is not particularly limited, but the lower limit is determined from the viewpoint of reliably preventing so-called chip flying, where chips cannot be fixed during the dicing process and chips fly off, and from peeling off during processes including transportation. , 0.3N/25mm or more in width is preferred, and 0.5N/25mm or more in width is particularly preferred. In addition, the upper limit value of the adhesive force is set in 2. from the viewpoint of reliably preventing so-called adhesive residue, where a part of the radiation-curable adhesive layer adheres to the adherend when the reflow-compatible dicing tape is peeled off. 0N/25mm or less is preferable, and 1.5N/25mm or less width is particularly preferable.
基材層の材料としては、特に限定されない。しかし、基材層は放射線硬化型粘着剤層と共に加熱されることになるから、２１０℃以上まで加熱されることになる。従って、基材層は、上記加熱条件に対して十分な耐熱性を備えている必要がある。上記から、好ましい基材層としては、例えば、ポリエチレンテレフタレート（ＰＥＴ）フィルム、ポリエチレンナフタレート（ＰＥＮ）フィルム、ポリエーテルサルフオン（ＰＥＳ）フィルム、ポリエーテルイミド（ＰＥＩ）フィルム、ポリサルフオン（ＰＳＦ）フィルム、ポリフェニレンサルファイド（ＰＰＳ）フィルム、ポリエーテルエーテルケトン（ＰＥＥＫ）フィルム、ポリアリレート（ＰＡＲ）フィルム、アラミドフィルム、ポリイミドフィルム、又は液晶ポリマー（ＰＣＰ）フィルム等が挙げられる。このうち、ダイシング工程時のチャック性の点から、ポリエーテルエーテルケトン（ＰＥＥＫ）フィルムが、特に好ましい。 The material for the base layer is not particularly limited. However, since the base material layer is heated together with the radiation-curable adhesive layer, it is heated to 210° C. or higher. Therefore, the base material layer needs to have sufficient heat resistance against the above heating conditions. From the above, preferred base layers include, for example, polyethylene terephthalate (PET) film, polyethylene naphthalate (PEN) film, polyether sulfon (PES) film, polyetherimide (PEI) film, polysulfon (PSF) film, Examples include polyphenylene sulfide (PPS) film, polyetheretherketone (PEEK) film, polyarylate (PAR) film, aramid film, polyimide film, and liquid crystal polymer (PCP) film. Among these, polyetheretherketone (PEEK) film is particularly preferred from the viewpoint of chuckability during the dicing process.
基材層の厚みは、使用条件等により適宜選択可能であり、例えば、５～２５０μｍの範囲内であることが好ましい。基材層の厚みが上記数値範囲内であることにより、リフロー対応ダイシングテープの折れや裂けを防止して、優れたハンドリング性を得ることができる。 The thickness of the base material layer can be appropriately selected depending on the usage conditions, and is preferably within the range of 5 to 250 μm, for example. When the thickness of the base material layer is within the above numerical range, the reflow compatible dicing tape can be prevented from bending or tearing, and excellent handling properties can be obtained.
放射線硬化型粘着剤層は、放射線硬化型粘着剤層に被着体を貼りあわせた後に、放射線照射してから２１０℃にて１０分の加熱処理をし、該加熱処理後に前記放射線硬化型粘着剤層から前記被着体を剥離させた際における前記被着体の貼り合わせ面をＸ線光電子分光法にて測定した際の炭素量が、３０ｍｏｌ％以下となっている。放射線照射の条件としては、波長３５０ｎｍの放射線を１０００ｍＪ／ｃｍ２照射することが挙げられる。The radiation-curable adhesive layer is formed by pasting the adherend onto the radiation-curing adhesive layer, irradiating it with radiation, and then heat-treating it at 210°C for 10 minutes. The amount of carbon when the bonded surface of the adherend was measured by X-ray photoelectron spectroscopy after peeling off the adherend from the agent layer was 30 mol % or less. The conditions for radiation irradiation include irradiating radiation with a wavelength of 350 nm at 1000 mJ/cm 2 .
放射線硬化型粘着剤層は、放射線照射してから２１０℃にて１０分の加熱処理をしても被着体の剥離面の炭素量は３０ｍｏｌ％以下に低減されている。従って、放射線硬化型粘着剤層の粘着剤が被着体に残存することが防止され、被着体のダイシングテープからの浮きも防止されている。被着体の剥離面の炭素量は３０ｍｏｌ％以下であれば、特に限定されないが、２５ｍｏｌ％以下が特に好ましい。 Even if the radiation-curable adhesive layer is heat-treated at 210° C. for 10 minutes after radiation irradiation, the amount of carbon on the peeled surface of the adherend is reduced to 30 mol% or less. Therefore, the adhesive of the radiation-curable adhesive layer is prevented from remaining on the adherend, and the adherend is also prevented from floating from the dicing tape. The carbon content on the peeled surface of the adherend is not particularly limited as long as it is 30 mol% or less, but is particularly preferably 25 mol% or less.
なお、上記被着体の剥離面の炭素量とは、被着体の剥離面に付着している成分全量中における炭素の割合を意味する。 Note that the carbon content on the peeled surface of the adherend means the proportion of carbon in the total amount of components adhering to the peeled surface of the adherend.
放射線硬化型粘着剤層は、粘着成分として粘着剤を含む。粘着剤は、主成分としてエチレン性不飽和結合を有する重合性化合物、エチレン性不飽和結合を有する重合性化合物の重合体並びに／またはカチオン及び／若しくはアニオンと反応する環状構造を有する化合物と、光重合開始剤と、を含む。 The radiation-curable adhesive layer contains an adhesive as an adhesive component. The adhesive contains a polymerizable compound having an ethylenically unsaturated bond as a main component, a polymer of the polymerizable compound having an ethylenically unsaturated bond, and/or a compound having a cyclic structure that reacts with a cation and/or anion, and a photosensitive adhesive. A polymerization initiator.
エチレン性不飽和結合を有する重合性化合物
粘着剤の主成分として配合されるエチレン性不飽和結合を有する重合性化合物は、特に限定されず、従来の感光性組成物に配合されているものを用いることができる。エチレン性不飽和結合を有する重合性化合物としては、例えば、エチレン、プロピレン、ブチレン、イソブチレン、塩化ビニル、塩化ビニリデン、フッ化ビニリデン、テトラフルオロエチレン等の不飽和脂肪族炭化水素；(メタ)アクリル酸、α―クロル（メタ）アクリル酸、イタコン酸、マレイン酸、シトラコン酸、フマル酸、ハイミック酸、クロトン酸、イソクロトン酸、ビニル酢酸、アリル酢酸、桂皮酸、ソルビン酸、メサコン酸等のエチレン性不飽和結合を有するカルボン酸；コハク酸モノ［２－（メタ）アクリロイロキシエチル］、フタル酸モノ［２－（メタ）アクリロイロキシエチル］、ω－カルボキシポリカプロラクトンモノ（メタ）アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ（メタ）アクリレート；ヒドロキシエチル（メタ）アクリレート・マレート、ヒドロキシプロピル（メタ）アクリレート・マレート、ジシクロペンタジエン・マレートまたは１個のカルボキシル基と２個以上の(メタ)アクリロイル基とを有する多官能（メタ）アクリレート等の不飽和多塩基酸；(メタ)アクリル酸－２－ヒドロキシエチル、（メタ）アクリル酸－２－ヒドロキシプロピル、（メタ）アクリル酸グリシジル、下記化合物Ｎｏ．Ａ１～Ｎｏ．Ａ４、（メタ）アクリル酸メチル、（メタ）アクリル酸ブチル、（メタ）アクリル酸イソブチル、（メタ）アクリル酸－ｔ－ブチル、（メタ）アクリル酸シクロヘキシル、（メタ）アクリル酸ｎ－オクチル、（メタ）アクリル酸イソオクチル、（メタ）アクリル酸イソノニル、（メタ）アクリル酸ステアリル、（メタ）アクリル酸ラウリル、（メタ）アクリル酸メトキシエチル、（メタ）アクリル酸ジメチルアミノメチル、（メタ）アクリル酸ジメチルアミノエチル、（メタ）アクリル酸アミノプロピル、（メタ）アクリル酸ジメチルアミノプロピル、（メタ）アクリル酸エトキシエチル、（メタ）アクリル酸ポリ（エトキシ）エチル、（メタ）アクリル酸ブトキシエトキシエチル、（メタ）アクリル酸エチルヘキシル、（メタ）アクリル酸フェノキシエチル、（メタ）アクリル酸テトラヒドロフリル、（メタ）アクリル酸ビニル、（メタ）アクリル酸アリル、（メタ）アクリル酸ベンジル、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、１，４－ブタンジオールジ（メタ）アクリレート、１，６－ヘキサンジオールジ（メタ）アクリレート、トリメチロールエタントリ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、トリシクロデカンジメチロールジ（メタ）アクリレート、トリ［（メタ）アクリロイルエチル］イソシアヌレート、ポリエステル（メタ）アクリレートオリゴマー等の（メタ）アクリル酸とアルコール又はフェノールとのエステルである（メタ）アクリレートが挙げられる。Polymerizable compound having an ethylenically unsaturated bond The polymerizable compound having an ethylenically unsaturated bond blended as the main component of the adhesive is not particularly limited, and those blended in conventional photosensitive compositions are used. be able to. Examples of polymerizable compounds having an ethylenically unsaturated bond include unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, and tetrafluoroethylene; (meth)acrylic acid; , α-chloro(meth)acrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hemic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, etc. Carboxylic acids with saturated bonds; both mono[2-(meth)acryloyloxyethyl] succinate, mono[2-(meth)acryloyloxyethyl] phthalate, ω-carboxypolycaprolactone mono(meth)acrylate, etc. Mono(meth)acrylate of a polymer having a carboxyl group and a hydroxyl group at the end; hydroxyethyl (meth)acrylate maleate, hydroxypropyl (meth)acrylate maleate, dicyclopentadiene maleate or one carboxyl group and two or more Unsaturated polybasic acids such as polyfunctional (meth)acrylates having a (meth)acryloyl group; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, (meth)acrylic acid Glycidyl, the following compound No. A1~No. A4, methyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, ( Isooctyl meth)acrylate, Isononyl (meth)acrylate, Stearyl (meth)acrylate, Lauryl (meth)acrylate, Methoxyethyl (meth)acrylate, Dimethylaminomethyl (meth)acrylate, Dimethyl (meth)acrylate Aminoethyl, aminopropyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, ethoxyethyl (meth)acrylate, poly(ethoxy)ethyl (meth)acrylate, butoxyethoxyethyl (meth)acrylate, (meth)acrylate ) Ethylhexyl acrylate, phenoxyethyl (meth)acrylate, tetrahydrofuryl (meth)acrylate, vinyl (meth)acrylate, allyl (meth)acrylate, benzyl (meth)acrylate, ethylene glycol di(meth)acrylate, Diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol Di(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, pentaerythritol tetra(meth)acrylate, Esters of (meth)acrylic acid and alcohol or phenol, such as pentaerythritol tri(meth)acrylate, tricyclodecane dimethyloldi(meth)acrylate, tri[(meth)acryloylethyl]isocyanurate, polyester(meth)acrylate oligomer, etc. Examples include (meth)acrylates.
また、他のエチレン性不飽和結合を有する重合性化合物としては、例えば、（メタ）アクリル酸亜鉛、（メタ）アクリル酸マグネシウム等の（メタ）アクリル酸の金属塩；マレイン酸無水物、イタコン酸無水物、シトラコン酸無水物、メチルテトラヒドロ無水フタル酸、テトラヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、５－（２，５－ジオキソテトラヒドロフリル）－３－メチル－３－シクロヘキセン－１，２－ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸－無水マレイン酸付加物、ドデセニル無水コハク酸、無水メチルハイミック酸等の不飽和多塩基酸の酸無水物；（メタ）アクリルアミド、メチレンビス－（メタ）アクリルアミド、ジエチレントリアミントリス（メタ）アクリルアミド、キシリレンビス（メタ）アクリルアミド、α－クロロ（メタ）アクリルアミド、Ｎ－２－ヒドロキシエチル（メタ）アクリルアミド等の（メタ）アクリル酸とアミン化合物とのアミド；アクロレイン等の不飽和アルデヒド；（メタ）アクリロニトリル、α－クロロアクリロニトリル、シアン化ビニリデン、シアン化アリル等の不飽和ニトリル；スチレン、４－メチルスチレン、４－エチルスチレン、４－メトキシスチレン、４－ヒドロキシスチレン、４－クロロスチレン、ジビニルベンゼン、ビニルトルエン、ビニル安息香酸、ビニルフェノール、ビニルスルホン酸、４－ビニルベンゼンスルホン酸、ビニルベンジルメチルエーテル、ビニルベンジルグリシジルエーテル等の不飽和芳香族化合物；メチルビニルケトン等の不飽和ケトン；ビニルアミン、アリルアミン、Ｎ－ビニルピロリドン、ビニルピペリジン等の不飽和アミン化合物；アリルアルコール、クロチルアルコール等のビニルアルコール；ビニルメチルエーテル、ビニルエチルエーテル、ｎ－ブチルビニルエーテル、イソブチルビニルエーテル、アリルグリシジルエーテル等のビニルエーテル；マレイミド、Ｎ－フェニルマレイミド、Ｎ－シクロヘキシルマレイミド等の不飽和イミド類；インデン、１－メチルインデン等のインデン類；１，３－ブタジエン、イソプレン、クロロプレン等の脂肪族共役ジエン類；ポリスチレン、ポリメチル（メタ）アクリレート、ポリ－ｎ－ブチル（メタ）アクリレート、ポリシロキサン等の重合体分子鎖の末端にモノ（メタ）アクリロイル基を有するマクロモノマー類；ビニルクロリド、ビニリデンクロリド、ジビニルスクシナート、ジアリルフタラート、トリアリルホスファート、トリアリルイソシアヌラート、ビニルチオエーテル、ビニルイミダゾール、ビニルオキサゾリン、ビニルカルバゾール、ビニルピロリドン、ビニルピリジン、水酸基含有ビニルモノマー及びポリイソシアネート化合物のビニルウレタン化合物、水酸基含有ビニルモノマー及びポリエポキシ化合物のビニルエポキシ化合物が挙げられる。これらの化合物は単独で使用してもよく、２種以上を併用してもよい。なお、「（メタ）アクリル酸」とは、アクリル酸及び／またはメタクリル酸を意味し、「（メタ）アクリレート」とは、アクリレート及び／またはメタクリレートを意味する。 In addition, examples of other polymerizable compounds having ethylenically unsaturated bonds include metal salts of (meth)acrylic acid such as zinc (meth)acrylate and magnesium (meth)acrylate; maleic anhydride, and itaconic acid. Anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2 - Acid anhydrides of unsaturated polybasic acids such as dicarboxylic acid anhydrides, trialkyltetrahydrophthalic anhydride-maleic anhydride adducts, dodecenyl succinic anhydride, methylhimic anhydride; (meth)acrylamide, methylene bis-(meth) ) Amides of (meth)acrylic acid and amine compounds such as acrylamide, diethylenetriamine tris(meth)acrylamide, xylylene bis(meth)acrylamide, α-chloro(meth)acrylamide, and N-2-hydroxyethyl(meth)acrylamide; acrolein, etc. unsaturated aldehydes; unsaturated nitriles such as (meth)acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, Unsaturated aromatic compounds such as 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether, vinylbenzyl glycidyl ether; methyl vinyl ketone, etc. unsaturated ketones; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone, and vinylpiperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, Vinyl ethers such as allyl glycidyl ether; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; indenes such as indene and 1-methylindene; aliphatic conjugates such as 1,3-butadiene, isoprene, and chloroprene. Dienes; Macromonomers having a mono(meth)acryloyl group at the end of the polymer molecular chain such as polystyrene, polymethyl(meth)acrylate, poly-n-butyl(meth)acrylate, polysiloxane; vinyl chloride, vinylidene chloride, Divinyl succinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, vinyl urethane compounds of hydroxyl group-containing vinyl monomers and polyisocyanate compounds , hydroxyl group-containing vinyl monomers, and vinyl epoxy compounds such as polyepoxy compounds. These compounds may be used alone or in combination of two or more. In addition, "(meth)acrylic acid" means acrylic acid and/or methacrylic acid, and "(meth)acrylate" means acrylate and/or methacrylate.
また、他のエチレン性不飽和結合を有する重合性化合物としては、例えば、エポキシ化合物に不飽和モノカルボン酸を反応させて、生成した水酸基に多塩基酸及び／または多塩基酸無水物を反応させて得られる多塩基酸変性不飽和モノカルボン酸化エポキシ化合物を挙げることができる。 In addition, as other polymerizable compounds having ethylenically unsaturated bonds, for example, an epoxy compound is reacted with an unsaturated monocarboxylic acid, and the generated hydroxyl group is reacted with a polybasic acid and/or a polybasic acid anhydride. Polybasic acid-modified unsaturated monocarboxylic oxidized epoxy compounds can be mentioned.
多塩基酸変性不飽和モノカルボン酸化エポキシ化合物の調製に使用できるエポキシ化合物としては、例えば、上記したカチオン及び／またはアニオンと反応する環状構造を有する化合物であるエポキシ化合物を挙げることができる。また、多塩基酸変性不飽和モノカルボン酸化エポキシ化合物の調製に使用できる不飽和モノカルボン酸としては、例えば、（メタ）アクリル酸、クロトン酸、桂皮酸、ソルビン酸、ヒドロキシエチル（メタ）アクリレート・マレート、ヒドロキシエチル（メタ）アクリレート・マレート、ヒドロキシプロピル（メタ）アクリレート・マレート、ヒドロキシプロピル（メタ）アクリレート・マレート、ジシクロペンタジエン・マレート等が挙げられる。 Examples of the epoxy compound that can be used to prepare the polybasic acid-modified unsaturated monocarboxylated epoxy compound include epoxy compounds that are compounds having a cyclic structure that reacts with the above-mentioned cations and/or anions. In addition, examples of unsaturated monocarboxylic acids that can be used to prepare polybasic acid-modified unsaturated monocarboxylated epoxy compounds include (meth)acrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl (meth)acrylate, Maleate, hydroxyethyl (meth)acrylate malate, hydroxypropyl (meth)acrylate malate, hydroxypropyl (meth)acrylate malate, dicyclopentadiene malate, and the like.
多塩基酸変性不飽和モノカルボン酸化エポキシ化合物の調製に使用できる多塩基酸としては、ビフェニルテトラカルボン酸、テトラヒドロフタル酸、コハク酸、ビフタル酸、マレイン酸、トリメリット酸、ピロメリット酸、２，２’－３，３’－ベンゾフェノンテトラカルボン酸、ヘキサヒドロフタル酸、メチルテトラヒドロフタル酸、ナジック酸、メチルナジック酸、トリアルキルテトラヒドロフタル酸、ヘキサヒドロフタル酸、５－（２，５－ジオキソテトラヒドロフリル）－３－メチル－３－シクロヘキセン－１，２－ジカルボン酸、トリアルキルテトラヒドロフタル酸－マレイン酸付加物、ドデセニルコハク酸、メチルハイミック酸等が挙げられる。また、多塩基酸無水物としては、上記した多塩基酸の無水物、エチレングリコールビスアンヒドロトリメリテート、グリセロールトリスアンヒドロトリメリテート等が挙げられる。 Polybasic acids that can be used to prepare polybasic acid-modified unsaturated monocarboxylated epoxy compounds include biphenyltetracarboxylic acid, tetrahydrophthalic acid, succinic acid, biphthalic acid, maleic acid, trimellitic acid, pyromellitic acid, 2'-3,3'-benzophenonetetracarboxylic acid, hexahydrophthalic acid, methyltetrahydrophthalic acid, nadic acid, methylnadic acid, trialkyltetrahydrophthalic acid, hexahydrophthalic acid, 5-(2,5-dioxo Examples thereof include (tetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid, trialkyltetrahydrophthalic acid-maleic acid adduct, dodecenylsuccinic acid, methylhimic acid, and the like. Further, examples of the polybasic acid anhydride include the above-mentioned polybasic acid anhydrides, ethylene glycol bisanhydrotrimellitate, glycerol trisanhydrotrimellitate, and the like.
多塩基酸変性不飽和モノカルボン酸化エポキシ化合物を調製する際における、エポキシ化合物、不飽和モノカルボン酸、多塩基酸及び／または多塩基酸無水物の反応モル比は、例えば、エポキシ化合物のエポキシ基１個に対し、上記不飽和モノカルボン酸のカルボキシル基が０．１～１．０個で付加させた構造を有するエポキシ付加物において、該エポキシ付加物の水酸基１個に対し、上記多塩基酸及び／または多塩基酸無水物が０．１～１．０個となる比率となるようにするのが好ましい。エポキシ化合物、不飽和モノカルボン酸、多塩基酸及び／または多塩基酸無水物の反応は、常法に従って行なうことができる。 When preparing a polybasic acid-modified unsaturated monocarboxylated epoxy compound, the reaction molar ratio of the epoxy compound, unsaturated monocarboxylic acid, polybasic acid and/or polybasic acid anhydride is, for example, the epoxy group of the epoxy compound. In an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monocarboxylic acid are added to one hydroxyl group of the epoxy adduct, the polybasic acid It is preferable to set the ratio such that the number of polybasic acid anhydrides and/or polybasic acid anhydrides is 0.1 to 1.0. The reaction of the epoxy compound, unsaturated monocarboxylic acid, polybasic acid and/or polybasic acid anhydride can be carried out according to a conventional method.
エチレン性不飽和結合を有する重合性化合物の重合体
粘着剤の主成分として配合されるエチレン性不飽和結合を有する重合性化合物の重合体としては、例えば、上記したエチレン性不飽和結合を有する重合性化合物の重合体や共重合体を挙げることができる。このうち、分子量の制御が容易で粘着力の調整が行いやすいという観点から、（メタ）アクリル酸及び／または上記した（メタ）アクリレートを含むモノマーの重合体である（メタ）アクリル系重合体が好ましい。Polymer of a polymerizable compound having an ethylenically unsaturated bond As a polymer of a polymerizable compound having an ethylenically unsaturated bond to be blended as a main component of the adhesive, for example, the above-mentioned polymer having an ethylenically unsaturated bond is used. Polymers and copolymers of chemical compounds can be mentioned. Among these, (meth)acrylic polymers, which are polymers of monomers containing (meth)acrylic acid and/or the above-mentioned (meth)acrylates, are preferred from the viewpoint of easy control of molecular weight and adjustment of adhesive strength. preferable.
カチオン及び／またはアニオンと反応する環状構造を有する化合物
粘着剤の主成分として配合されるカチオン及び／またはアニオンと反応する環状構造を有する化合物としては、例えば、エポキシ化合物、グリシジルエーテル類等の酸素原子を有する３員環構造を有する化合物が挙げられる。エポキシ化合物としては、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールＡノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物；ビスフェノール型エポキシ化合物、多官能エポキシ基を有するポリフェニルメタン型エポキシ化合物等のエポキシ化合物、３，４－エポキシ－６－メチルシクロヘキシルメチル－３，４－エポキシ－６－メチルシクロヘキサンカルボキシレート、３，４－エポキシシクロヘキシルメチル－３，４－エポキシシクロヘキサンカルボキシレート、１－エポキシエチル－３，４－エポキシシクロヘキサン等の脂環式エポキシ化合物；フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類；テトラグリシジルジアミノジフェニルメタン、トリグリシジルＰ－アミノフェノール、Ｎ，Ｎ－ジグリシジルアニリン等のグリシジルアミン類；１，３－ジグリシジル－５，５－ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物；ジシクロペンタジエンジオキシド等のジオキシド化合物；ナフタレン型エポキシ化合物；トリフェニルメタン型エポキシ化合物；ジシクロペンタジエン型エポキシ化合物等が挙げられる。Compounds with a cyclic structure that react with cations and/or anions Compounds with a cyclic structure that react with cations and/or anions that are blended as main components of adhesives include, for example, oxygen atoms such as epoxy compounds and glycidyl ethers. Examples include compounds having a three-membered ring structure. Examples of epoxy compounds include novolac-type epoxy compounds such as phenol novolac-type epoxy compounds, biphenyl novolac-type epoxy compounds, cresol novolac-type epoxy compounds, bisphenol A novolac-type epoxy compounds, and dicyclopentadiene novolac-type epoxy compounds; bisphenol-type epoxy compounds; Epoxy compounds such as polyphenylmethane type epoxy compounds having functional epoxy groups, 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3 , 4-epoxycyclohexane carboxylate, alicyclic epoxy compounds such as 1-epoxyethyl-3,4-epoxycyclohexane; glycidyl esters such as phthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, dimer acid glycidyl ester; Glycidylamines such as tetraglycidyldiaminodiphenylmethane, triglycidyl P-aminophenol, N,N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin, triglycidyl isocyanurate; Dioxide compounds such as dicyclopentadiene dioxide; naphthalene type epoxy compounds; triphenylmethane type epoxy compounds; dicyclopentadiene type epoxy compounds and the like.
グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、１，４－ブタンジオールジグリシジルエーテル、１，６－ヘキサンジオールジグリシジルエーテル、１，８－オクタンジオールジグリシジルエーテル、１，１０－デカンジオールジグリシジルエーテル、２，２－ジメチル－１，３－プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、１，４－シクロヘキサンジメタノールジグリシジルエーテル、１，１，１－トリ（グリシジルオキシメチル）プロパン、１，１，１－トリ（グリシジルオキシメチル）エタン、１，１，１－トリ（グリシジルオキシメチル）メタン、１，１，１，１－テトラ（グリシジルオキシメチル）メタン等が挙げられる。 Examples of glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1, 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri(glycidyloxymethyl)propane, 1,1,1-tri(glycidyloxymethyl)ethane, 1,1,1-tri(glycidyloxymethyl) ) methane, 1,1,1,1-tetra(glycidyloxymethyl)methane, and the like.
また、粘着剤の主成分として配合されるカチオン及び／またはアニオンと反応する環状構造を有する化合物としては、例えば、オキセタン等の酸素原子を有する４員環構造を有する化合物等が挙げられる。これらの化合物は単独で使用してもよく、２種以上を併用してもよい。 Further, examples of compounds having a cyclic structure that react with cations and/or anions that are blended as a main component of the adhesive include compounds having a four-membered ring structure having an oxygen atom such as oxetane. These compounds may be used alone or in combination of two or more.
光重合開始剤
光重合開始剤は、エチレン性不飽和結合を有する重合性化合物に活性エネルギー線を照射することによりエチレン性不飽和結合を有する重合性化合物を光硬化させる際に、光硬化を促進させる効果を発揮する。Photopolymerization initiator A photopolymerization initiator promotes photocuring when a polymerizable compound having an ethylenically unsaturated bond is photocured by irradiating the compound with active energy rays. Demonstrates the effect of
光重合開始剤としては、公知の重合開始剤を適宜選択でき、例えば、α－ヒドロキシアセトフェノン、α－アミノアルキルフェノン、ベンゾフェノン、フェニルビフェニルケトン、１－ヒドロキシ－１－ベンゾイルシクロヘキサン、ベンゾイン、ベンジルジメチルケタール、１－ベンジル－１－ジメチルアミノ－１－（４'－モルホリノベンゾイル）プロパン、２－モルホリル－２－（４'－メチルメルカプト）ベンゾイルプロパン、チオキサントン、１－クロル－４－プロポキシチオキサントン、イソプロピルチオキサントン、ジエチルチオキサントン、エチルアントラキノン、４－ベンゾイル－４'－メチルジフェニルスルフィド、ベンゾインブチルエーテル、２－ヒドロキシ－２－ベンゾイルプロパン、２－ヒドロキシ－２－（４'－イソプロピル）ベンゾイルプロパン、４－ブチルベンゾイルトリクロロメタン、４－フェノキシベンゾイルジクロロメタン、ベンゾイル蟻酸メチル、１，７－ビス（９'－アクリジニル）ヘプタン、９－ｎ－ブチル－３，６－ビス（２'－モルホリノイソブチロイル）カルバゾール、２－メチル－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－フェニル－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２－ナチル－４，６－ビス（トリクロロメチル）－ｓ－トリアジン、２，２－ビス（２－クロロフェニル）－４，５，４’，５’－テトラフェニル－１－２’－ビイミダゾール、４、４－アゾビスイソブチロニトリル、トリフェニルホスフィン、過酸化ベンゾイル等が挙げられる。このうち、α－ヒドロキシアセトフェノン、α－アミノアルキルフェノンが好ましい。 As the photopolymerization initiator, known polymerization initiators can be appropriately selected, such as α-hydroxyacetophenone, α-aminoalkylphenone, benzophenone, phenyl biphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzoin, and benzyl dimethyl ketal. , 1-benzyl-1-dimethylamino-1-(4'-morpholinobenzoyl)propane, 2-morpholyl-2-(4'-methylmercapto)benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone , diethylthioxanthone, ethyl anthraquinone, 4-benzoyl-4'-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4'-isopropyl)benzoylpropane, 4-butylbenzoyltrichloro Methane, 4-phenoxybenzoyldichloromethane, methyl benzoyl formate, 1,7-bis(9'-acridinyl)heptane, 9-n-butyl-3,6-bis(2'-morpholinoisobutyroyl)carbazole, 2-methyl -4,6-bis(trichloromethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-natyl-4,6-bis(trichloromethyl)-s-triazine , 2,2-bis(2-chlorophenyl)-4,5,4',5'-tetraphenyl-1-2'-biimidazole, 4,4-azobisisobutyronitrile, triphenylphosphine, peroxide Examples include benzoyl. Among these, α-hydroxyacetophenone and α-aminoalkylphenone are preferred.
α－アミノアルキルフェノンとしては、例えば、下記式の化合物、
Ｒ３及びＲ４は、それぞれ独立に、水素原子；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、炭素原子数１～４のアルコキシ基、アミノ基、炭素原子数１～４のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素数２～１２のアルケニル基を表し、Ｒ３とＲ４は、連結して３～６員環の環状アルカンを形成してもよく、
Ｒ５、Ｒ６、Ｒ７及びＲ８は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基；ハロゲン原子で置換されている若しくは無置換の炭素原子数１～８のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基を表し、
Ｒ９、Ｒ１０、Ｒ１１、Ｒ１２及びＲ１３は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基；ハロゲン原子で置換されている若しくは無置換の炭素原子数１～８のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基、－ＯＲ１４、－Ｏ－ＣＯ－Ｏ－Ｒ１５、－ＮＲ１６Ｒ１７、－ＳＲ１８を表し、かつ、Ｒ９、Ｒ１０、Ｒ１１、Ｒ１２及びＲ１３のうち少なくとも１つは、ニトロ基、－ＯＲ１４、－Ｏ－ＣＯ－Ｏ－Ｒ１５、－ＮＲ１６Ｒ１７、－ＳＲ１８の群より選ばれる基であり、
Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７及びＲ１８は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、炭素原子数１～４のアルコキシ基、アミノ基、炭素原子数１～４のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素数２～１２のアルケニル基；炭素原子数２～１２の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、 上記アルキル基及びアリールアルキル基中のメチレン鎖は、－Ｏ－、－Ｓ－、－ＮＲ１９－、－ＣＯ－、－ＣＯ－Ｏ－、－Ｏ－ＣＯ－又は－Ｏ－ＣＯ－Ｏ－で置き換えられていてもよく、上記アルキル基の末端は不飽和結合であってもよく、
Ｒ１９は、水素原子；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素数２～１２のアルケニル基を表す。）Examples of α-aminoalkylphenones include compounds of the following formula,
R 3 and R 4 are each independently a hydrogen atom; an alkyl group having 1 to 12 carbon atoms substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or a nitro group; a carbon atom number 1 ~4 alkyl groups, hydroxyl groups, carboxyl groups, halogen atoms, cyano groups, or unsubstituted phenyl groups; C1-4 alkyl groups, hydroxyl groups, C1-4 alkyl groups; Alkoxy group, amino group, alkylthio group having 1 to 4 carbon atoms, carboxyl group, halogen atom, cyano group or nitro group, or unsubstituted arylalkyl group having 7 to 30 carbon atoms; 2 carbon atoms ~12 alkenyl group, R 3 and R 4 may be connected to form a 3- to 6-membered cyclic alkane,
R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group; a halogen atom-substituted or unsubstituted carbon atom number of 1 to 8 alkyl group; represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted arylalkyl group having 7 to 30 carbon atoms;
R 9 , R 10 , R 11 , R 12 and R 13 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group; a carbon atom substituted with a halogen atom or unsubstituted; Alkyl group having 1 to 8 carbon atoms; arylalkyl group having 7 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or a nitro group , -OR 14 , -O-CO-O-R 15 , -NR 16 R 17 , -SR 18 , and at least one of R 9 , R 10 , R 11 , R 12 and R 13 is A group selected from the group of nitro group, -OR 14 , -O-CO-O-R 15 , -NR 16 R 17 , -SR 18 ,
R 14 , R 15 , R 16 , R 17 and R 18 are a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group, or an unsubstituted alkyl group having 1 to 12 carbon atoms; a hydroxyl group; Carboxyl group, halogen atom, cyano group, or unsubstituted phenyl group substituted with cyano group or nitro group; alkyl group having 1 to 4 carbon atoms, hydroxyl group, alkoxy group having 1 to 4 carbon atoms, amino group, carbon atom An alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted arylalkyl group having 7 to 30 carbon atoms; an alkenyl group having 2 to 12 carbon atoms; a carbon atom Represents a heterocyclic group containing from 2 to 12, a trialkylsilyl group, or a triarylsilyl group, and the methylene chain in the alkyl group and arylalkyl group is -O-, -S-, -NR 19 -, -CO -, -CO-O-, -O-CO- or -O-CO-O- may be substituted, and the terminal of the alkyl group may be an unsaturated bond,
R 19 is a hydrogen atom; a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted alkyl group having 1 to 12 carbon atoms; an alkyl group having 1 to 4 carbon atoms, a hydroxyl group , a carboxyl group, a halogen atom, a cyano group, or an unsubstituted phenyl group; a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or a nitro group represents an unsubstituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms; an alkenyl group having 2 to 12 carbon atoms; )
下記式の化合物
Ｒ３及びＲ４は、それぞれ独立に、水素原子；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；炭素子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、炭素原子数１～４のアルコキシ基、アミノ基、炭素原子数１～４のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素原子数２～１２のアルケニル基を表し、Ｒ３とＲ４は、連結して３～６員環の環状アルカンを形成してもよく、
Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｒ１１及びＲ１２は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基；ハロゲン原子で置換されている若しくは無置換の炭素原子数１～８のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基を表し、
Ｘは、単結合又はｎ価の有機基、酸素原子、硫黄原子又は窒素原子を表し、
ｎは、２～６の数であり、ｎ個の基は互いに同じである。）Compound of the following formula
R 3 and R 4 are each independently a hydrogen atom; a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted alkyl group having 1 to 12 carbon atoms; having 1 carbon atom; ~4 alkyl groups, hydroxyl groups, carboxyl groups, halogen atoms, cyano groups, or unsubstituted phenyl groups; C1-4 alkyl groups, hydroxyl groups, C1-4 alkyl groups; Alkoxy group, amino group, alkylthio group having 1 to 4 carbon atoms, carboxyl group, halogen atom, cyano group, or unsubstituted arylalkyl group having 7 to 30 carbon atoms; number of carbon atoms represents an alkenyl group of 2 to 12, and R 3 and R 4 may be linked to form a 3 to 6-membered cyclic alkane;
R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently substituted with a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; a halogen atom or unsubstituted alkyl group having 1 to 8 carbon atoms; substituted with an alkyl group having 1 to 4 carbon atoms, hydroxyl group, carboxyl group, halogen atom, cyano group, or nitro group, or unsubstituted 7 carbon atoms ~30 arylalkyl groups,
X represents a single bond or an n-valent organic group, an oxygen atom, a sulfur atom or a nitrogen atom,
n is a number from 2 to 6, and the n groups are the same. )
下記式の化合物が挙げられる。
Ｒ３及びＲ４は、それぞれ独立に、水素原子；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、炭素原子数１～４のアルコキシ基、アミノ基、炭素原子数１～４のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素原子数２～１２のアルケニル基；Ｒ３とＲ４は、連結して３～６員環の環状アルカンを形成してもよく、
Ｒ５、Ｒ６、Ｒ７及びＲ８は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基；ハロゲン原子で置換されている若しくは無置換の炭素原子数１～８のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基を表し、
Ｒ９及びＲ１０は、それぞれ独立に、水素原子、水酸基、カルボキシル基、ハロゲン原子または炭素原子数１～４のアルキル基を表し、ｎが２以上の場合は同じか又は異なり、
ｎは、１～１２の数を表し、
Ｘは、二価の有機基であり、
Ｙは、下記式（Ｉ－１）又は（Ｉ－２）で表される構造であり、
上記アルキル基及びアリールアルキル基、ならびにアルキレン基中のメチレン鎖は、－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯ－Ｏ－、－Ｏ－ＣＯ－又は－Ｏ－ＣＯ－Ｏ－で置き換えられていてもよい。）
Ｒ３’及びＲ４’は、それぞれ独立に、水素原子；水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数１～１２のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基；炭素原子数１～４のアルキル基、水酸基、炭素原子数１～４のアルコキシ基、アミノ基、炭素原子数１～４のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基；炭素原子数２～１２のアルケニル基を表し、Ｒ３’とＲ４’は、連結して３～６員環の環状アルカンを形成してもよく、
Ｒ５’、Ｒ６’、Ｒ７’及びＲ８’は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基；ハロゲン原子で置換されている若しくは無置換の炭素原子数１～８のアルキル基；炭素原子数１～４のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数７～３０のアリールアルキル基を表し、
上記アルキル基及びアリールアルキル基、ならびにアルキレン基中のメチレン鎖は、－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯ－Ｏ－、－Ｏ－ＣＯ－又は－Ｏ－ＣＯ－Ｏ－で置き換えられていてもよい。）
Ｒ１４、Ｒ１５、Ｒ１６、Ｒ１７、Ｒ１８、Ｒ１９、Ｒ２０及びＲ２１は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、Ｒ２２、ＯＲ２３、ＳＲ２４、ＮＲ２５Ｒ２６、ＣＯＲ２７、ＳＯＲ２８、ＳＯ２Ｒ２９又はＣＯＮＲ３０Ｒ３１を表し、Ｒ１６及びＲ１８は、互いに結合して環を形成していてもよく、
Ｒ２２、Ｒ２３、Ｒ２４、Ｒ２５、Ｒ２６、Ｒ２７、Ｒ２８、Ｒ２９、Ｒ３０及びＲ３１は、それぞれ独立に、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｘ２は、単結合又はＣＯを表し、
Ｘ３は、酸素原子、硫黄原子、セレン原子、ＣＲ３２Ｒ３３、ＣＯ、ＮＲ３４又はＰＲ３５を表し、
Ｒ３２、Ｒ３３、Ｒ３４及びＲ３５は、それぞれ独立に、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１２、Ｒ１３、Ｒ２２、Ｒ２３、Ｒ２４、Ｒ２５、Ｒ２６、Ｒ２７、Ｒ２８、Ｒ２９、Ｒ３０、Ｒ３１、Ｒ３２、Ｒ３３、Ｒ３４及びＲ３５中の炭素原子数１～２０のアルキル基又は炭素原子数７～３０のアリールアルキル基中のメチレン基は、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基又は複素環基で置換されていてもよく、該アルキル基又はアリールアルキル基中のメチレン鎖は－Ｏ－で中断されていてもよい。）Examples include compounds of the following formula.
R 3 and R 4 are each independently a hydrogen atom; an alkyl group having 1 to 12 carbon atoms substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or a nitro group; a carbon atom number 1 ~4 alkyl groups, hydroxyl groups, carboxyl groups, halogen atoms, cyano groups, or unsubstituted phenyl groups; C1-4 alkyl groups, hydroxyl groups, C1-4 alkyl groups; Alkoxy group, amino group, alkylthio group having 1 to 4 carbon atoms, carboxyl group, halogen atom, cyano group, or unsubstituted arylalkyl group having 7 to 30 carbon atoms; number of carbon atoms 2-12 alkenyl group; R 3 and R 4 may be linked to form a 3- to 6-membered cyclic alkane;
R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; a halogen atom-substituted or unsubstituted alkyl having 1 to 8 carbon atoms; Group; represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted arylalkyl group having 7 to 30 carbon atoms, substituted with a cyano group or a nitro group;
R 9 and R 10 each independently represent a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom, or an alkyl group having 1 to 4 carbon atoms, and when n is 2 or more, they are the same or different;
n represents a number from 1 to 12,
X is a divalent organic group,
Y is a structure represented by the following formula (I-1) or (I-2),
The methylene chain in the above alkyl group, arylalkyl group, and alkylene group is replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- It may be. )
R 3' and R 4' are each independently a hydrogen atom; a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted alkyl group having 1 to 12 carbon atoms; a carbon atom; Alkyl group, hydroxyl group, carboxyl group, halogen atom, cyano group, or unsubstituted phenyl group having 1 to 4 carbon atoms; alkyl group having 1 to 4 carbon atoms, hydroxyl group, 1 to 4 carbon atoms; 4 alkoxy group, amino group, alkylthio group having 1 to 4 carbon atoms, carboxyl group, halogen atom, cyano group or nitro group or unsubstituted arylalkyl group having 7 to 30 carbon atoms; carbon represents an alkenyl group having 2 to 12 atoms, and R 3' and R 4' may be connected to form a 3- to 6-membered cyclic alkane;
R 5' , R 6' , R 7' and R 8' each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; a carbon atom number of 1 substituted with a halogen atom or unsubstituted; ~8 alkyl group; represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, or an unsubstituted arylalkyl group having 7 to 30 carbon atoms, substituted with a cyano group, or a nitro group; ,
The methylene chain in the above alkyl group, arylalkyl group, and alkylene group is replaced with -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O- It may be. )
R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and R 21 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R 22 , OR 23 , SR 24 , NR 25 R 26 , COR 27 , SOR 28 , SO 2 R 29 or CONR 30 R 31 , and R 16 and R 18 may be combined with each other to form a ring;
R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 are each independently an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 20 carbon atoms; 30 aryl group, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,
X2 represents a single bond or CO,
X3 represents an oxygen atom, a sulfur atom, a selenium atom, CR 32 R 33 , CO, NR 34 or PR 35 ,
R 32 , R 33 , R 34 and R 35 are each independently an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of number 2 to 20,
Carbon in R 12 , R 13 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 and R 35 The methylene group in the alkyl group having 1 to 20 atoms or the arylalkyl group having 7 to 30 atoms may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, The methylene chain in the alkyl group or arylalkyl group may be interrupted with -O-. )
また、光重合開始剤として、オキシムエステル化合物を使用してもよい。光重合開始剤がオキシムエステル化合物であることにより、アウトガスの発生を確実に低減できる。 Furthermore, an oxime ester compound may be used as a photopolymerization initiator. When the photopolymerization initiator is an oxime ester compound, the generation of outgas can be reliably reduced.
オキシムエステル化合物としては、例えば、下記式の化合物、
Ｒ１１、Ｒ１２及びＲ１３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１１、Ｒ１２及びＲ１３で表わされる置換基の水素原子は、更にＯＲ２１、ＣＯＲ２１、ＳＲ２１、ＮＲ２２Ｒ２３、ＣＯＮＲ２２Ｒ２３、－ＮＲ２２－ＯＲ２３、－ＮＣＯＲ２２－ＯＣＯＲ２３、－Ｃ（＝Ｎ－ＯＲ２１）－Ｒ２２、－Ｃ（＝Ｎ－ＯＣＯＲ２１）－Ｒ２２、ＣＮ、ハロゲン原子、又はＣＯＯＲ２１で置換されていてもよく、
Ｒ２１、Ｒ２２及びＲ２３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ２１、Ｒ２２及びＲ２３で表される置換基の水素原子は、更にＣＮ、ハロゲン原子、水酸基又はカルボキシル基で置換されていてもよく、
Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２４－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断されていてもよく、
Ｒ２４は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキル部分は、分岐側鎖があってもよく、環状アルキルであってもよく、また、Ｒ１２とＲ１３及びＲ２２とＲ２３はそれぞれ一緒になって環を形成していてもよく、
Ｒ３及びＲ４は、それぞれ独立に、Ｒ１１、ＯＲ１１、ＳＲ１１、ＣＯＲ１１、ＣＯＮＲ１２Ｒ１３、ＮＲ１２ＣＯＲ１１、ＯＣＯＲ１１、ＣＯＯＲ１１、ＳＣＯＲ１１、ＯＣＳＲ１１、ＣＯＳＲ１１、ＣＳＯＲ１１、ＣＮ又はハロゲン原子を表し、
ａ及びｂは、それぞれ独立に、０～４の整数を表し、
Ｘは、酸素原子、硫黄原子、セレン原子、ＣＲ３１Ｒ３２、ＣＯ、ＮＲ３３又はＰＲ３４を表し、
Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基又は炭素原子数７～３０のアリールアルキル基を表し、
Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４で表される置換基のアルキル部分は、分岐側鎖があってもよく、環状アルキルであってもよく、Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよく、
Ｒ５はＯＨ、ＣＯＯＨ又は下記一般式（II）で表される基を表す。
Ｚ２は、結合手であって、１～３のＲ６で置換された炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｚ２で表される結合手のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２２－、－ＮＲ２２ＣＯＯ－、－ＯＣＯＮＲ２２－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断されていてもよく、Ｚ２で表される結合手のアルキレン部分は分岐側鎖があってもよく、環状アルキレンであってもよく、
Ｒ６は、ＯＲ４１、ＳＲ４１、ＣＯＮＲ４２Ｒ４３、ＮＲ４２ＣＯＲ４３、ＯＣＯＲ４１、ＣＯＯＲ４１、ＳＣＯＲ４１、ＯＣＳＲ４１、ＣＯＳＲ４１、ＣＳＯＲ４１、ＣＮ又はハロゲン原子を表し、
Ｒ４１、Ｒ４２及びＲ４３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基又は炭素原子数７～３０のアリールアルキル基を表し、Ｒ４１、Ｒ４２及びＲ４３表される置換基のアルキル部分は分岐側鎖があってもよく、環状アルキルであってもよく、Ｒ４２とＲ４３は、一緒になって環を形成していてもよく、
ｃは１～３の整数を表す。））As the oxime ester compound, for example, a compound of the following formula,
R 11 , R 12 and R 13 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of numbers 2 to 20,
The hydrogen atoms of the substituents represented by R 11 , R 12 and R 13 are further represented by OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , may be substituted with CN, a halogen atom, or COOR 21 ,
R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of numbers 2 to 20,
The hydrogen atom of the substituent represented by R 21 , R 22 and R 23 may be further substituted with CN, a halogen atom, a hydroxyl group or a carboxyl group,
The alkylene moiety of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is -O-, -S-, -COO-, -OCO-, -NR 24 -, - NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times,
R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; ,
The alkyl moiety of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 may have a branched side chain or may be a cyclic alkyl, and R 12 and R 13 and R 22 and R 23 may each be taken together to form a ring,
R 3 and R 4 are each independently R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , represents CN or a halogen atom,
a and b each independently represent an integer from 0 to 4,
X represents an oxygen atom, a sulfur atom, a selenium atom, CR 31 R 32 , CO, NR 33 or PR 34 ,
R 31 , R 32 , R 33 and R 34 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms. represents,
The alkyl moiety of the substituent represented by R 31 , R 32 , R 33 and R 34 may have a branched side chain or may be a cyclic alkyl, and R 31 , R 32 , R 33 and R 34 may each independently form a ring together with either adjacent benzene ring,
R 5 represents OH, COOH or a group represented by the following general formula (II).
Z 2 is a bond, and is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, substituted with 1 to 3 R 6 or represents a heterocyclic group having 2 to 20 carbon atoms,
The alkylene moiety of the bond represented by Z 2 is -O-, -S-, -COO-, -OCO-, -NR 22 -, -NR 22 COO-, -OCONR 22 -, -SCO-, - It may be interrupted 1 to 5 times by COS-, -OCS- or -CSO-, and the alkylene moiety of the bond represented by Z 2 may have a branched side chain or may be a cyclic alkylene. ,
R 6 represents OR 41 , SR 41 , CONR 42 R 43 , NR 42 COR 43 , OCOR 41 , COOR 41 , SCOR 41 , OCSR 41 , COSR 41 , CSOR 41 , CN or a halogen atom,
R 41 , R 42 and R 43 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, The alkyl moiety of the substituent represented by R 41 , R 42 and R 43 may have a branched side chain or may be a cyclic alkyl, and R 42 and R 43 together form a ring. It's okay,
c represents an integer from 1 to 3. ))
下記式の化合物、
下記式の化合物
下記式の化合物、
Ｒ１１、Ｒ１２及びＲ１３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１１、Ｒ１２及びＲ１３で表わされる基の水素原子は、更にＲ２1、ＯＲ２1、ＣＯＲ２1、ＳＲ２1、ＮＲ２２Ｒ２３、ＣＯＮＲ２２Ｒ２３、－ＮＲ２２－ＯＲ２３、－ＮＣＯＲ２２－ＯＣＯＲ２３、ＮＲ２２ＣＯＲ２1、ＯＣＯＲ２1、ＣＯＯＲ２1、ＳＣＯＲ２1、ＯＣＳＲ２1、ＣＯＳＲ２1、ＣＳＯＲ２1、水酸基、ニトロ基、ＣＮ、ハロゲン原子、又はＣＯＯＲ２1で置換されていてもよく、
Ｒ２1、Ｒ２２及びＲ２３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ２1、Ｒ２２及びＲ２３で表される基の水素原子は、更に水酸基、ニトロ基、ＣＮ、ハロゲン原子、水酸基又はカルボキシル基で置換されていてもよく、
Ｒ１1、Ｒ１２、Ｒ１３、Ｒ２1、Ｒ２２及びＲ２３で表される基のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２４－、－ＮＲ２４ＣＯ－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により酸素原子が隣り合わない条件で１～５回中断されていてもよく、
Ｒ２４は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１1、Ｒ１２、Ｒ１３、Ｒ２1、Ｒ２２、Ｒ２３及びＲ２４で表される基のアルキル部分は、分岐側鎖があってもよく、環状アルキルであってもよく、
Ｒ３は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、Ｒ３で表される基のアルキル部分は、分岐側鎖があってもよく、環状アルキルであってもよく、また、Ｒ３とＲ７、Ｒ３とＲ８、Ｒ４とＲ５、Ｒ５とＲ６及びＲ６とＲ７はそれぞれ一緒になって環を形成していてもよく、
Ｒ３で表わされる基の水素原子は、更にＲ２1、ＯＲ２1、ＣＯＲ２1、ＳＲ２1、ＮＲ２２Ｒ２３、ＣＯＮＲ２２Ｒ２３、－ＮＲ２２－ＯＲ２３、－ＮＣＯＲ２２－ＯＣＯＲ２３、ＮＲ２２ＣＯＲ２1、ＯＣＯＲ２1、ＣＯＯＲ２1、ＳＣＯＲ２1、ＯＣＳＲ２1、ＣＯＳＲ２1、ＣＳＯＲ２1、水酸基、ニトロ基、ＣＮ、ハロゲン原子、又はＣＯＯＲ２1で置換されていてもよく、
Ｒ４、Ｒ５、Ｒ６及びＲ７は、それぞれ独立に、Ｒ１1、ＯＲ１1、ＳＲ１1、ＣＯＲ１４、ＣＯＮＲ１５Ｒ１６、ＮＲ１２ＣＯＲ１1、ＯＣＯＲ１1、ＣＯＯＲ１４、ＳＣＯＲ１1、ＯＣＳＲ１1、ＣＯＳＲ１４、ＣＳＯＲ１1、水酸基、ＣＮ又はハロゲン原子を表し、Ｒ４とＲ５、Ｒ５とＲ６及びＲ６とＲ７はそれぞれ一緒になって環を形成していてもよく、
Ｒ１４、Ｒ１５及びＲ１６は、水素原子又は炭素原子数１～２０のアルキル基を表し、Ｒ１４、Ｒ１５及びＲ１６で表される基のアルキル部分は、分岐側鎖があってもよく、環状アルキルであってもよく、Ｒ８は、Ｒ１1、ＯＲ１1、ＳＲ１1、ＣＯＲ１1、ＣＯＮＲ１２Ｒ１３、ＮＲ１２ＣＯＲ１1、ＯＣＯＲ１1、ＣＯＯＲ１1、ＳＣＯＲ１1、ＯＣＳＲ１1、ＣＯＳＲ１1、ＣＳＯＲ１1、水酸基、ＣＮ又はハロゲン原子を表し、
ｎは、０又は１を表す。）A compound of the following formula,
R 11 , R 12 and R 13 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of numbers 2 to 20,
The hydrogen atoms of the groups represented by R 11 , R 12 and R 13 are further represented by R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , may be substituted with a hydroxyl group, a nitro group, CN, a halogen atom, or a COOR 21 ,
R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of numbers 2 to 20,
The hydrogen atoms of the groups represented by R 21 , R 22 and R 23 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,
The alkylene moiety of the group represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times under the condition that oxygen atoms are not adjacent to each other,
R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; ,
The alkyl portion of the group represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 may have a branched side chain or may be a cyclic alkyl,
R 3 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; , the alkyl portion of the group represented by R 3 may have a branched side chain or may be a cyclic alkyl, and R 3 and R 7 , R 3 and R 8 , R 4 and R 5 , R 5 and R 6 and R 6 and R 7 may each be taken together to form a ring,
The hydrogen atom of the group represented by R 3 is further R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , NR 22 COR21 , OCOR21 , COOR21 , SCOR21 , OCSR21 , COSR21 , CSOR21 , may be substituted with a hydroxyl group, a nitro group, CN, a halogen atom, or COOR21 ,
R 4 , R 5 , R 6 and R 7 are each independently R 11 , OR 11 , SR 11 , COR 14 , CONR 15 R 16 , NR 12 COR 11 , OCOR 11 , COOR 14 , SCOR 11 , OCSR 11 , COSR 14 , CSOR 11 represent a hydroxyl group, CN or a halogen atom, and R 4 and R 5 , R 5 and R 6 and R 6 and R 7 may each be taken together to form a ring,
R 14 , R 15 and R 16 represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and the alkyl portion of the group represented by R 14 , R 15 and R 16 has a branched side chain. Often, R 8 may be a cyclic alkyl, R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 represents a hydroxyl group, CN or a halogen atom,
n represents 0 or 1. )
下記式の化合物、
下記式の化合物、
下記式の化合物、
Ｒ２１、Ｒ２２及びＲ２３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、Ｒ２１、Ｒ２２及びＲ２３で表される置換基の水素原子は、ＣＮ、ハロゲン原子、水酸基又はカルボキシル基で置換される場合もあり、
Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２４－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断される場合もあり、Ｒ２４は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキル部分は、分岐側鎖がある場合や環状アルキルである場合があり、また、Ｒ１２とＲ１３及びＲ２２とＲ２３はそれぞれ一緒になって環を形成する場合もあり、
Ｒ３、Ｌ１、Ｌ２及びＬ３は、Ｒ１１、ＯＲ１１、ＳＲ１１、ＣＯＲ１４、ＣＯＮＲ１５Ｒ１６、ＮＲ１２ＣＯＲ１１、ＯＣＯＲ１１、ＣＯＯＲ１４、ＳＣＯＲ１１、ＯＣＳＲ１１、ＣＯＳＲ１４、ＣＳＯＲ１１、水酸基、ニトロ基、ＣＮ又はハロゲン原子を表し、Ｌ１とＲ３、Ｒ３とＬ２及びＬ２とＬ３はそれぞれ一緒になって環を形成する場合もあり、Ｒ１４、Ｒ１５及びＲ１６は、水素原子又は炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、Ｒ４は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、Ｒ４で表される基のアルキル部分は、分岐側鎖がある場合や環状アルキルである場合があり、Ｒ４で表わされる基の水素原子は、更にＲ２１、ＯＲ２１、ＣＯＲ２１、ＳＲ２１、ＮＲ２２Ｒ２３、ＣＯＮＲ２２Ｒ２３、－ＮＲ２２－ＯＲ２３、－ＮＣＯＲ２２－ＯＣＯＲ２３、ＮＲ２２ＣＯＲ２１、ＯＣＯＲ２１、ＣＯＯＲ２１、－Ｃ（＝Ｎ－ＯＲ２１）－Ｒ２２、－Ｃ（＝Ｎ－ＯＣＯＲ２１）－Ｒ２２、ＳＣＯＲ２１、ＯＣＳＲ２１、ＣＯＳＲ２１、ＣＳＯＲ２１、水酸基、ニトロ基、ＣＮ、ハロゲン原子、又はＣＯＯＲ２１で置換される場合もあり、Ｘは、直接結合、ＣＯまたは下記一般式（Ｉ－Ａ）で表される基を表す。
Ｚ１及びＺ２で表される結合手のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２４－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断される場合もあり、Ｚ２で表される結合手のアルキレン部分は分岐側鎖がある場合や環状アルキレンである場合もある。
Ｒ５は、Ｒ１１、ＯＲ１１、ＣＯＲ１１、ＳＲ１１、ＣＯＮＲ１２Ｒ１３又はＣＮを表し、Ｒ１１、Ｒ１２及びＲ１３は、上記一般式（Ｉ）と同じである。））
Ｒ９は、ＯＨ、ＣＯＯＨ又は下記一般式（ＩＩ－Ａ）で表される基を表し、
Ｙは、酸素原子、硫黄原子、セレン原子、ＣＲ３１Ｒ３２、ＣＯ、ＮＲ３３又はＰＲ３４を表し、
αは１～１０の整数を表し、Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基又は炭素原子数７～３０のアリールアルキル基を表し、
Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４で表される置換基のアルキル部分は、分岐側鎖がある場合や環状アルキレンである場合もあり、Ｒ３１、Ｒ３２、Ｒ３３及びＲ３４は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成する場合もある。
Ｚ４は、結合手であって、１～３のＲ１０で置換される炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｚ４で表される結合手のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ、－ＮＲ２４－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断される場合もあり、Ｚ４で表される結合手のアルキレン部分は分岐側鎖がある場合や環状アルキレンである場合もあり、Ｒ１０は、ＯＲ４１、ＳＲ４１、ＣＯＮＲ４２Ｒ４３、ＮＲ４２ＣＯＲ４３、ＯＣＯＲ４１、ＣＯＯＲ４１、ＳＣＯＲ４１、ＯＣＳＲ４１、ＣＯＳＲ４１、ＣＳＯＲ４１、ＣＮ又はハロゲン原子を表し、Ｒ４１、Ｒ４２及びＲ４３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基又は炭素原子数７～３０のアリールアルキル基を表し、Ｒ４１、Ｒ４２及びＲ４３で表される置換基のアルキル部分は分岐側鎖がある場合や環状アルキレンである場合もあり、Ｒ４２とＲ４３は、一緒になって環を形成する場合もあり、ａは１～３の整数を表す。Ｒ２２及びＲ２４は、上記一般式（Ｉ）と同じである。））A compound of the following formula,
R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of numbers 2 to 20, and the hydrogen atoms of the substituents represented by R 21 , R 22 and R 23 may be substituted with CN, a halogen atom, a hydroxyl group or a carboxyl group,
The alkylene moiety of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is -O-, -S-, -COO-, -OCO-, -NR 24 -, - NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and R 24 is a hydrogen atom, a carbon atom number of 1 to 20 represents an alkyl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 11 , R 12 , R 13 , R 21 , The alkyl moiety of the substituent represented by R 22 and R 23 may have a branched side chain or be a cyclic alkyl, and R 12 and R 13 and R 22 and R 23 may each be combined together. Sometimes they form a ring,
R 3 , L 1 , L 2 and L 3 are R 11 , OR 11 , SR 11 , COR 14 , CONR 15 R 16 , NR 12 COR 11 , OCOR 11 , COOR 14 , SCOR 11 , OCSR 11 , COSR 14 , CSOR 11 represents a hydroxyl group, a nitro group, CN or a halogen atom; L 1 and R 3 , R 3 and L 2 and L 2 and L 3 may each come together to form a ring; R 14 , R 15 and R 16 are a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. represents a hydrogen atom , an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocycle having 2 to 20 carbon atoms. The alkyl moiety of the group represented by R 4 may have a branched side chain or be a cyclic alkyl, and the hydrogen atom of the group represented by R 4 may further include R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , -C (=N-OR 21 )- R 22 , -C(=N-OCOR 21 )-R 22 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , may be substituted with a hydroxyl group, a nitro group, CN, a halogen atom, or COOR 21 , represents a direct bond, CO, or a group represented by the following general formula (IA).
The alkylene moiety of the bond represented by Z 1 and Z 2 is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 COO-, -OCONR 24 -, -SCO -, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene portion of the bond represented by Z 2 may have a branched side chain or be a cyclic alkylene. be.
R 5 represents R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN, and R 11 , R 12 and R 13 are the same as in the above general formula (I). ))
R 9 represents OH, COOH or a group represented by the following general formula (II-A),
Y represents an oxygen atom, a sulfur atom, a selenium atom, CR 31 R 32 , CO, NR 33 or PR 34 ,
α represents an integer of 1 to 10, and R 31 , R 32 , R 33 and R 34 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or represents an arylalkyl group having 7 to 30 carbon atoms,
The alkyl moiety of the substituent represented by R 31 , R 32 , R 33 and R 34 may have a branched side chain or be a cyclic alkylene, and R 31 , R 32 , R 33 and R 34 are They may each independently form a ring together with either of the adjacent benzene rings.
Z 4 is a bond, and is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, which is substituted with 1 to 3 R 10 or represents a heterocyclic group having 2 to 20 carbon atoms,
The alkylene moiety of the bond represented by Z 4 is -O-, -S-, -COO-, -OCO, -NR 24 -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS -, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene portion of the bond represented by Z 4 may have a branched side chain or be a cyclic alkylene, and R 10 represents OR 41 , SR 41 , CONR 42 R 43 , NR 42 COR 43 , OCOR 41 , COOR 41 , SCOR 41 , OCSR 41 , COSR 41 , CSOR 41 , CN or a halogen atom, and R 41 , R 42 and R 43 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, R 41 , R 42 and R The alkyl moiety of the substituent represented by 43 may have a branched side chain or be a cyclic alkylene, R 42 and R 43 may form a ring together, and a is 1 to 3. represents an integer. R 22 and R 24 are the same as in the above general formula (I). ))
下記式の化合物、
Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８及びＲ９（以下、Ｒ３～Ｒ９とも記載）は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、Ｒ１０、ＯＲ１０、ＳＲ１０、ＮＲ１１Ｒ１２、ＣＯＲ１０、ＳＯＲ１０、ＳＯ２Ｒ１０又はＣＯＮＲ１１Ｒ１２を表し、
Ｒ１０、Ｒ１１及びＲ１２は、それぞれ独立に、炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基を表し、Ｒ１１とＲ１２は、結合して環を形成する場合もあり、
Ｒ１、Ｒ２、Ｒ１０、Ｒ１１及びＲ１２で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、ＮＲ１１Ｒ１２、カルボキシル基、（メタ）アクリロイル基、エポキシ基、ビニル基、メルカプト基、イソシアネート基、カルボキシル基又は複素環含有基で置換される場合があり、炭素原子数２～２０の炭化水素基又は炭素原子数２～２０の複素環含有基中のメチレン基は－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ１３－、－ＮＲ１３ＣＯ－、－Ｓ－、－ＳＯ２－、－ＳＣＯ－又は－ＣＯＳ－により置換される場合もあり、
Ｒ１３は、水素原子、炭素原子数１～２０の炭化水素基を表し、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ５とＲ６、Ｒ６とＲ７、Ｒ７とＲ８及びＲ８とＲ９は結合して環を形成する場合もある。）A compound of the following formula,
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 (hereinafter also referred to as R 3 to R 9 ) each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group. , represents a carboxyl group, R 10 , OR 10 , SR 10 , NR 11 R 12 , COR 10 , SOR 10 , SO 2 R 10 or CONR 11 R 12 ,
R 10 , R 11 and R 12 each independently represent a hydrocarbon group having 1 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms, and R 11 and R 12 are bonded to form a ring. may form,
The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocycle-containing group having 2 to 20 carbon atoms represented by R 1 , R 2 , R 10 , R 11 and R 12 is a halogen atom, a nitro group, It may be substituted with a cyano group, hydroxyl group, NR 11 R 12 , carboxyl group, (meth)acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group, carboxyl group or heterocycle-containing group, and has 2 carbon atoms. The methylene group in the ~20 hydrocarbon group or the heterocycle-containing group having 2 to 20 carbon atoms is -O-, -CO-, -COO-, -OCO-, -NR 13 -, -NR 13 CO-, -S-, -SO 2 -, -SCO- or -COS- may be substituted,
R 13 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 and R 8 and R 9 may be combined to form a ring. )
下記式の化合物、
下記式の化合物、
Ｒ１１、Ｒ１２及びＲ１３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１１、Ｒ１２及びＲ１３で表わされる置換基の水素原子は、更にＯＲ２１、ＣＯＲ２１、ＳＲ２１、ＮＲ２２Ｒ２３、ＣＯＮＲ２２Ｒ２３、－ＮＲ２２－ＯＲ２３、－ＮＣＯＲ２２－ＯＣＯＲ２３、－Ｃ（＝Ｎ－ＯＲ２１）－Ｒ２２、－Ｃ（＝Ｎ－ＯＣＯＲ２１）－Ｒ２２、ＣＮ、ハロゲン原子、又はＣＯＯＲ２１で置換されている場合もあり、
Ｒ２１、Ｒ２２及びＲ２３は、それぞれ独立に、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ２１、Ｒ２２及びＲ２３で表される置換基の水素原子は、更にＣＮ、ハロゲン原子、水酸基又はカルボキシル基で置換されている場合もあり、
Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２４－、－ＮＲ２４ＣＯＯ－、－ＯＣＯＮＲ２４－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断されている場合もあり、
Ｒ２４は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数６～３０のアリール基、炭素原子数７～３０のアリールアルキル基又は炭素原子数２～２０の複素環基を表し、
Ｒ１１、Ｒ１２、Ｒ１３、Ｒ２１、Ｒ２２及びＲ２３で表される置換基のアルキル部分は、分岐側鎖がある場合があり、環状アルキルである場合があり、また、Ｒ１２とＲ１３及びＲ２２とＲ２３はそれぞれ一緒になって環を形成する場合があり、
Ｚ１は、結合手であって、単結合、－Ｏ－、－Ｓ－、－ＮＲ２２－、－ＮＲ２２ＣＯ－、－ＳＯ２－、－ＣＳ－、－ＯＣＯ－又は－ＣＯＯ－を表し、
Ｚ２は、結合手であって、単結合、炭素原子数１～２０のアルカンジイル基、炭素原子数６～３０のアリールジイル基、炭素原子数７～３０のアリールアルキルジイル基又は炭素原子数２～２０の２価の複素環基を表し、
Ｚ２で表される結合手のアルキレン部分は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２２－、－ＮＲ２２ＣＯＯ－、－ＯＣＯＮＲ２２－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又は－ＣＳＯ－により１～５回中断されている場合があり、Ｚ２で表される結合手のアルキレン部分は分岐側鎖がある場合があり、環状アルキレンである場合があり、
Ｘは下記化学式（Ｉ－Ａ）又は（Ｉ－Ｂ）で表される結合手を表す。）
R 11 , R 12 and R 13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, represents an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,
The hydrogen atoms of the substituents represented by R 11 , R 12 and R 13 are further represented by OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , -NR 22 -OR 23 , -NCOR 22 -OCOR 23 , -C(=N-OR 21 )-R 22 , -C(=N-OCOR 21 )-R 22 , CN, a halogen atom, or COOR 21 may be substituted,
R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom Represents a heterocyclic group of number 2 to 20,
The hydrogen atoms of the substituents represented by R 21 , R 22 and R 23 may be further substituted with CN, a halogen atom, a hydroxyl group or a carboxyl group,
The alkylene moiety of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is -O-, -S-, -COO-, -OCO-, -NR 24 -, - It may be interrupted 1 to 5 times by NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-,
R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; ,
The alkyl moiety of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 may have a branched side chain, may be a cyclic alkyl, and R 12 and R 13 and R 22 and R 23 may each be taken together to form a ring,
Z 1 is a bond, and represents a single bond, -O-, -S-, -NR 22 -, -NR 22 CO-, -SO 2 -, -CS-, -OCO- or -COO- ,
Z 2 is a bond, and is a single bond, an alkanediyl group having 1 to 20 carbon atoms, an aryldiyl group having 6 to 30 carbon atoms, an arylalkyldiyl group having 7 to 30 carbon atoms, or 2 carbon atoms. Represents ~20 divalent heterocyclic groups,
The alkylene moiety of the bond represented by Z 2 is -O-, -S-, -COO-, -OCO-, -NR 22 -, -NR 22 COO-, -OCONR 22 -, -SCO-, - It may be interrupted 1 to 5 times by COS-, -OCS- or -CSO-, and the alkylene part of the bond represented by Z 2 may have a branched side chain and may be a cyclic alkylene. can be,
X represents a bond represented by the following chemical formula (IA) or (IB). )
下記式の化合物、
Ｒ１及びＲ２で表される炭素原子数１～２０の炭化水素基又はＲ１及びＲ２で表される複素環を含有する炭素原子数２～２０の基の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ＣＨ２＝ＣＨ－Ｏ－、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ１及びＲ２で表される炭素原子数１～２０の炭化水素基又はＲ１及びＲ２で表される複素環を含有する炭素原子数２～２０の基中のメチレン基は、－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ３－、－ＮＲ３ＣＯ－、－Ｓ－、－ＣＳ－、－ＳＯ２－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又はＣＳＯ－で置換される場合もあり、
Ｒ３は、水素原子又は炭素原子数１～２０の炭化水素基を表し、
ｎは０又は１を表す。式中の＊は、＊部分で、隣接する基と結合することを意味する。）A compound of the following formula,
The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 and R 2 or the group having 2 to 20 carbon atoms containing a heterocycle represented by R 1 and R 2 is a halogen atom, May be substituted with a nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, CH 2 ═CH—O—, mercapto group, isocyanate group, or heterocycle-containing group. The methylene group in the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 and R 2 or the heterocycle-containing group having 2 to 20 carbon atoms represented by R 1 and R 2 is -O-, -CO-, -COO-, -OCO-, -NR 3 -, -NR 3 CO-, -S-, -CS-, -SO 2 -, -SCO-, -COS-, -OCS - or CSO- may be substituted,
R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
n represents 0 or 1. * in the formula means that the * moiety is bonded to an adjacent group. )
下記式の化合物、
Ｒ１３、Ｒ１４及びＲ１５は、それぞれ独立に、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～２０のアリール基、炭素原子数７～２０のアリールアルキル基又は炭素原子数２～２０の複素環含有基を表し、
Ｒ１３、Ｒ１４及びＲ１５で表される、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～２０のアリール基、炭素原子数７～２０のアリールアルキル基又は炭素原子数２～２０の複素環含有基の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ１３、Ｒ１４及びＲ１５で表される、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数７～２０のアリールアルキル基又は炭素原子数２～２０の複素環含有基中のメチレン基は、－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ１６－、－ＮＲ１６ＣＯ－、－Ｓ－、－ＣＳ－、－ＳＯ２－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又はＣＳＯ－で置換される場合もあり、
Ｒ１６は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～２０のアリール基又は炭素原子数７～２０のアリールアルキル基を表し、
環Ａ１及び環Ａ２は、縮合して炭素原子数３０以下の芳香環を形成し、
Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９及びＲ１０（以下、Ｒ１～Ｒ１０とも記載）のうち少なくとも一つが、下記一般式（ＩＩ）で表される基であり、
ｍは、Ａ１が取り得る置換基の数以下の正の整数であり、
ｍ≧２の場合は、複数存在するＲ１１が各々異なる場合があり、
ｎは、Ａ２が取り得る置換基の数以下の正の整数であり、
ｎ≧２の場合は、複数存在するＲ１２が各々異なる場合があり、
Ｒ１とＲ２、Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ７とＲ８、Ｒ８とＲ９、Ｒ９とＲ１０、Ｒ１１とＲ１２が結合して環を形成する場合もあり、ｍ≧２の場合はＲ１１とＲ１１が結合して環を形成する場合もあり、ｎ≧２の場合はＲ１２とＲ１２が結合して環を形成する場合もある。
Ｒ１７及びＲ１８で表される、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～２０のアリール基、炭素原子数７～２０のアリールアルキル基又は炭素原子数２～２０の複素環含有基の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ１７及びＲ１８で表される、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数７～２０のアリールアルキル基又は炭素原子数２～２０の複素環含有基中のメチレン基は－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ１９－、－ＮＲ１９ＣＯ－、－Ｓ－、－ＣＳ－、－ＳＯ２－、－ＳＣＯ－、－ＣＯＳ－、－ＯＣＳ－又はＣＳＯ－で置換される場合もあり、
Ｒ１９は、水素原子、炭素原子数１～２０のアルキル基、炭素原子数３～２０のシクロアルキル基、炭素原子数４～２０のシクロアルキルアルキル基、炭素原子数６～２０のアリール基又は炭素原子数７～２０のアリールアルキル基を表し、
ｋは０又は１を表す。））A compound of the following formula,
R 13 , R 14 and R 15 each independently represent an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, or a cycloalkylalkyl group having 4 to 20 carbon atoms; represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
An alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, and 6 carbon atoms, represented by R 13 , R 14 and R 15 The hydrogen atom of the ~20 aryl group, the arylalkyl group having 7 to 20 carbon atoms, or the heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, 1 carbon atom, which may be substituted with a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocycle-containing group, and is represented by R 13 , R 14 and R 15 ~20 alkyl group, cycloalkyl group having 3 to 20 carbon atoms, cycloalkylalkyl group having 4 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, or heterocycle containing 2 to 20 carbon atoms The methylene group in the group is -O-, -CO-, -COO-, -OCO-, -NR 16 -, -NR 16 CO-, -S-, -CS-, -SO 2 -, -SCO- , -COS-, -OCS- or CSO- may be substituted,
R 16 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or represents an arylalkyl group having 7 to 20 carbon atoms,
Ring A 1 and Ring A 2 are fused to form an aromatic ring having 30 or less carbon atoms,
At least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 (hereinafter also referred to as R 1 to R 10 ) is represented by the following general formula ( II) is a group represented by
m is a positive integer less than or equal to the number of substituents that A1 can have,
When m≧2, multiple R 11s may be different,
n is a positive integer less than or equal to the number of substituents that A2 can have,
When n≧2, multiple R 12s may be different,
R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 and R 12 may combine to form a ring, when m≧2, R 11 and R 11 may combine to form a ring, and when n≧2, R 12 and R 12 may combine to form a ring. Sometimes they combine to form a ring.
An alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, and a cycloalkylalkyl group having 6 to 20 carbon atoms, represented by R 17 and R 18 . The hydrogen atom of the aryl group, arylalkyl group having 7 to 20 carbon atoms, or heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group. an alkyl group having 1 to 20 carbon atoms, which may be substituted with a group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocycle-containing group, and is represented by R 17 and R 18 ; The methylene group in the cycloalkyl group having 3 to 20 atoms, the cycloalkylalkyl group having 4 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, or the heterocycle-containing group having 2 to 20 carbon atoms is - O-, -CO-, -COO-, -OCO-, -NR 19 -, -NR 19 CO-, -S-, -CS-, -SO 2 -, -SCO-, -COS-, -OCS- or may be substituted with CSO-,
R 19 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or represents an arylalkyl group having 7 to 20 carbon atoms,
k represents 0 or 1. ))
下記式の化合物等が挙げられる。
Ｒ１３、Ｒ１４及びＲ１５は、それぞれ独立に、炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基を表し、
Ｒ１３、Ｒ１４及びＲ１５で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基の水素原子は、下記一般式（ＩＩ）で表される基、ニトリル基、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ１３、Ｒ１４及びＲ１５で表される炭素原子数２～２０の炭化水素基又は炭素原子数２～２０の複素環含有基中のメチレン基は－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ１６－、－ＮＲ１６ＣＯ－、－Ｓ－、－ＳＯ２－、－ＳＣＯ－又は－ＣＯＳ－で置換される場合もあり、
Ｒ１６は、水素原子、炭素原子数１～２０の炭化水素基を表し、
Ｒ１１及びＲ１２は、それぞれ独立に水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基を表し、
Ｒ１１及びＲ１２で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ１１及びＲ１２で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基中のメチレン基は－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ１７－、－ＮＲ１７ＣＯ－、－Ｓ－、－ＳＯ２－、－ＳＣＯ－又は－ＣＯＳ－で置換される場合もあり、
Ｒ１７は、水素原子、炭素原子数１～２０の炭化水素基を表し、
Ｒ１～Ｒ１０のうち少なくとも一つが、下記一般式（ＩＩ）で表される基であり、
Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ７とＲ８、Ｒ８とＲ９及びＲ９とＲ１０が結合して環を形成する場合もあり、
ｍは０又は１を表す。
Ｒ２１及びＲ２２で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、Ｒ２１及びＲ２２で表される炭素原子数１～２０の炭化水素基又は炭素原子数２～２０の複素環含有基中のメチレン基は－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＮＲ２３－、－ＮＲ２３ＣＯ－、－Ｓ－、－ＳＯ２－、－ＳＣＯ－又は－ＣＯＳ－で置換される場合もあり、
Ｒ２３は、水素原子、炭素原子数１～２０の炭化水素基を表し、
ｎは０又は１を表す。））Examples include compounds of the following formulas.
R 13 , R 14 and R 15 each independently represent a hydrocarbon group having 1 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms,
The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocycle-containing group having 2 to 20 carbon atoms represented by R 13 , R 14 and R 15 is a group represented by the following general formula (II). , substituted with a nitrile group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocycle-containing group In some cases, the methylene group in the hydrocarbon group having 2 to 20 carbon atoms or the heterocycle-containing group having 2 to 20 carbon atoms represented by R 13 , R 14 and R 15 is -O-, -CO- , -COO-, -OCO-, -NR 16 -, -NR 16 CO-, -S-, -SO 2 -, -SCO- or -COS-,
R 16 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms,
R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms represented by R 11 and R 12 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, or a carboxyl group. may be substituted with a group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group or a heterocycle-containing group, and the number of carbon atoms represented by R 11 and R 12 is 1 to 20 The methylene group in the hydrocarbon group or heterocycle-containing group having 2 to 20 carbon atoms is -O-, -CO-, -COO-, -OCO-, -NR 17 -, -NR 17 CO-, -S -, -SO 2 -, -SCO- or -COS- may be substituted,
R 17 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms,
At least one of R 1 to R 10 is a group represented by the following general formula (II),
When R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 and R 9 and R 10 combine to form a ring There is also
m represents 0 or 1.
The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms represented by R 21 and R 22 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, or a carboxyl group. may be substituted with a group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group or a heterocycle-containing group, and the number of carbon atoms represented by R 21 and R 22 is 1 to 20 The methylene group in the hydrocarbon group or heterocycle-containing group having 2 to 20 carbon atoms is -O-, -CO-, -COO-, -OCO-, -NR 23 -, -NR 23 CO-, -S -, -SO 2 -, -SCO- or -COS- may be substituted,
R 23 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms,
n represents 0 or 1. ))
上記した光重合開始剤のうち、光重合開始剤が分裂してもアウトガスの原因となることを防止することによりアウトガスの発生を確実に抑制する点から、分子量が高い光重合開始剤が好ましく、具体的には分子量が４００以上の光重合開始剤が好ましく、分子量が５００以上の光重合開始剤が特に好ましい。光重合開始剤の分子量の上限値は、特に限定されないが、例えば、１００００以下が挙げられる。 Among the above-mentioned photopolymerization initiators, photopolymerization initiators with a high molecular weight are preferred from the viewpoint of reliably suppressing the generation of outgas by preventing the photopolymerization initiator from causing outgassing even if it splits. Specifically, photopolymerization initiators with a molecular weight of 400 or more are preferred, and photopolymerization initiators with a molecular weight of 500 or more are particularly preferred. The upper limit of the molecular weight of the photopolymerization initiator is not particularly limited, but may be, for example, 10,000 or less.
光重合開始剤の配合量は、特に限定されず、適宜選択可能であるが、例えば、粘着剤１００質量％中に０．１～１０質量％が好ましく、１～５重量％が特に好ましい。 The amount of the photopolymerization initiator is not particularly limited and can be selected as appropriate, but for example, it is preferably 0.1 to 10% by weight, particularly preferably 1 to 5% by weight, based on 100% by weight of the adhesive.
粘着剤には、必要に応じて、任意成分として、可塑剤、顔料、染料、老化防止剤、帯電防止剤、弾性率等の粘着剤層の物性改善のために加えられる充填剤等の各種添加剤を添加することもできる。 The adhesive may optionally contain various additives such as plasticizers, pigments, dyes, anti-aging agents, antistatic agents, and fillers added to improve the physical properties of the adhesive layer such as modulus of elasticity. It is also possible to add agents.
放射線硬化型粘着剤層の厚さは、特に限定されないが、１～５０μｍであることが好ましく、５～２５μｍであることが特に好ましい。放射線硬化型粘着剤層の厚さが１μｍ未満では、被着体への追従性が損なわれてリフロー工程後のダイシングでの固着力が低下することがある。一方で、放射線硬化型粘着剤層の厚さが５０μｍ超では、粘着剤自体が破壊して被着体に欠けた粘着剤が付着する糊残りが生じることがある。 The thickness of the radiation-curable adhesive layer is not particularly limited, but is preferably 1 to 50 μm, particularly preferably 5 to 25 μm. If the thickness of the radiation-curable adhesive layer is less than 1 μm, the followability to the adherend may be impaired and the adhesion strength during dicing after the reflow process may be reduced. On the other hand, if the thickness of the radiation-curable adhesive layer exceeds 50 μm, the adhesive itself may be destroyed, resulting in adhesive residue where the chipped adhesive adheres to the adherend.
放射線の種類としては、放射線硬化型粘着剤層に含まれる粘着剤の種類に応じて適宜設定される。放射線としては、例えば、紫外線、電子線等が挙げられる。本発明のリフロー対応ダイシングテープでは、これらの放射線のうち、紫外線が特に好ましい。すなわち、放射線硬化型粘着剤層としては、紫外線硬化型粘着剤層が特に好ましく、粘着剤としては、紫外線硬化型粘着剤が特に好ましい。 The type of radiation is appropriately set depending on the type of adhesive contained in the radiation-curable adhesive layer. Examples of the radiation include ultraviolet rays and electron beams. Among these radiations, ultraviolet rays are particularly preferred in the reflow compatible dicing tape of the present invention. That is, as the radiation-curable adhesive layer, an ultraviolet-curable adhesive layer is particularly preferable, and as the adhesive, an ultraviolet-curable adhesive is particularly preferable.
紫外線の発生方式は、特に限定はされず、従来公知の発生方式を適宜採用することができる。具体的な紫外線の発生方式としては、例えば、放電ランプ方式（アークランプ）、フラッシュ方式、レーザー方式等が挙げられる。これらの方式のうち、工業的な生産の点から、放電ランプ方式が好ましく、放電ランプ方式の中でも高圧水銀ランプやメタルハライドランプを使用した照射方法が、紫外線の照射効率の点から特に好ましい。 The generation method of ultraviolet rays is not particularly limited, and any conventionally known generation method can be adopted as appropriate. Specific methods for generating ultraviolet rays include, for example, a discharge lamp method (arc lamp), a flash method, a laser method, and the like. Among these methods, the discharge lamp method is preferred from the viewpoint of industrial production, and among the discharge lamp methods, the irradiation method using a high-pressure mercury lamp or metal halide lamp is particularly preferred from the viewpoint of ultraviolet irradiation efficiency.
紫外線の波長について、紫外領域の波長は、特に限定されないが、一般的な光硬化に用いられる波長及び前記照射方法にて使用する紫外線発生源の波長の点から、２５０ｎｍ～４００ｎｍの範囲内であることが好ましい。 Regarding the wavelength of ultraviolet rays, the wavelength in the ultraviolet region is not particularly limited, but is within the range of 250 nm to 400 nm in terms of the wavelength used for general photocuring and the wavelength of the ultraviolet source used in the irradiation method. It is preferable.
紫外線の照射量は、紫外線による光重合開始剤の効果を生じさせることができる照射量であれば、特に限定されない。具体的には、例えば１０～３０００ｍＪ／ｃｍ２が好ましく、５０～２０００ｍＪ／ｃｍ２が特に好ましい。紫外線の照射量が１０ｍＪ／ｃｍ２未満の場合には、粘着剤が十分に硬化しない場合がある。また、紫外線の照射量が３０００ｍＪ／ｃｍ２超の場合には、粘着剤の光硬化が進行し過ぎて、放射線硬化型粘着剤層が割れるおそれがある。The irradiation amount of ultraviolet rays is not particularly limited as long as the irradiation amount can produce the effect of the photopolymerization initiator using ultraviolet rays. Specifically, for example, 10 to 3000 mJ/cm 2 is preferable, and 50 to 2000 mJ/cm 2 is particularly preferable. If the amount of ultraviolet rays is less than 10 mJ/cm 2 , the adhesive may not be sufficiently cured. Furthermore, if the amount of ultraviolet rays is more than 3000 mJ/cm 2 , the photo-curing of the adhesive may proceed too much and the radiation-curable adhesive layer may crack.
本発明のリフロー対応ダイシングテープの被着体としては、例えば、シリコンウエハを挙げることができる。 An example of the adherend of the reflow compatible dicing tape of the present invention is a silicon wafer.
以下に、本発明の実施例を説明するが、実施例に記載されている材料や配合量等は、特に限定的な記載がない限りは、この発明の範囲をそれらのみに限定する趣旨のものではなく、単なる説明例に過ぎない。 Examples of the present invention will be described below, but the materials, compounding amounts, etc. described in the examples are intended to limit the scope of the present invention to only those materials unless otherwise stated. It's just an illustrative example.
実施例１
光重合開始剤として、α－ヒドロキシアセトフェノン（Irugacure 184、BASF社製）を用いた。α－ヒドロキシアセトフェノンと、ブチル（メタ）アクリレートモノマー１００質量部に対して（メタ）アクリル酸モノマーを５質量部配合して合成したアクリル系共重合体（Ｍｗ＝７０万）とを、α－ヒドロキシアセトフェノン：アクリル系共重合体の質量比５：１００にて混合して、放射線硬化型の粘着剤を調製した。この粘着剤を５０μｍのＰＥＥＫフィルムに塗布し、粘着剤中の溶媒を１２０℃で揮発させて放射線硬化型粘着剤層（厚さ２０ｕｍ）としたリフロー対応ダイシングテープを作製した。Example 1
As a photopolymerization initiator, α-hydroxyacetophenone (Irugacure 184, manufactured by BASF) was used. α-hydroxy acetophenone and an acrylic copolymer (Mw = 700,000) synthesized by blending 5 parts by mass of (meth)acrylic acid monomer to 100 parts by mass of butyl (meth)acrylate monomer, A radiation-curable adhesive was prepared by mixing acetophenone and acrylic copolymer at a mass ratio of 5:100. This adhesive was applied to a 50 μm PEEK film, and the solvent in the adhesive was evaporated at 120° C. to produce a reflow-compatible dicing tape with a radiation-curable adhesive layer (20 μm thick).
実施例２
光重合開始剤として、オキシムエステル化合物を用いた。オキシムエステル化合物としては、下記化合物（分子量３５５）を使用した。
An oxime ester compound was used as a photopolymerization initiator. The following compound (molecular weight: 355) was used as the oxime ester compound.
実施例２で使用したオキシムエステル化合物は以下のようにして調製した。
ジクロロエタン９２ｇと塩化アルミ２１．７ｇ（１６３ ｍｍｏｌ）の溶液に、下記アルコール２０．７３ｇ（６．５ｍｍｏｌ）を加え、次いで、６℃以下でプロピオニルクロライド９．０ｇ（９７ｍｍｏｌ）を滴下した。１時間攪拌後、反応液を氷水に注ぎ、酢酸エチルを加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、脱溶媒しアシル体ａを１７．５ｇ得た。
20.73 g (6.5 mmol) of the following alcohol was added to a solution of 92 g of dichloroethane and 21.7 g (163 mmol) of aluminum chloride, and then 9.0 g (97 mmol) of propionyl chloride was added dropwise at 6° C. or lower. After stirring for 1 hour, the reaction solution was poured into ice water, ethyl acetate was added to separate oil and water, and the organic layer was washed with water. After drying the organic layer over anhydrous magnesium sulfate, the solvent was removed to obtain 17.5 g of acyl compound a.
オキシム化
得られたアシル体ａの１３．０ｇ（３５ｍｍｏｌ）と濃塩酸３．６ｇ（３５ｍｍｏｌ）とジメチルホルムアミド３０ｇの溶液に、亜硝酸イソブチル５．４ｇ（５２ｍｍｏｌ）を加え、室温で３．５時間攪拌した。攪拌後、反応液に、酢酸エチルと水を加え油水分離し、有機層を水で洗浄した。固体の析出した有機層にヘキサンを加え、ろ過した。得られた固体を減圧乾燥し、オキシム体ａを７．８ｇ得た。
オキシムエステル化
得られたオキシム体ａの５．０ｇ（１３ｍｍｏｌ）と、ピリジン２．１ｇ（２７ｍｍｏｌ）とジメチルホルムアミド１２ｇの溶液を、－１０℃以下の状態にし、無水酢酸１．６ｇ（１５ｍｍｏｌ）を滴下し、滴下後５℃で２時間攪拌した。攪拌後、反応液に、酢酸エチルと水を加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、脱溶媒し、上記のオキシムエステル化合物を３．５ｇ得た。Oxime esterification A solution of 5.0 g (13 mmol) of the obtained oxime a, 2.1 g (27 mmol) of pyridine, and 12 g of dimethylformamide was brought to a temperature below -10°C, and 1.6 g (15 mmol) of acetic anhydride was added. After the dropwise addition, the mixture was stirred at 5° C. for 2 hours. After stirring, ethyl acetate and water were added to the reaction solution to separate oil and water, and the organic layer was washed with water. After drying the organic layer over anhydrous magnesium sulfate, the solvent was removed to obtain 3.5 g of the above oxime ester compound.
上記のようにして得られたオキシムエステル化合物と、ブチル（メタ）アクリレートモノマー１００質量部に対して（メタ）アクリル酸モノマーを５質量部配合して合成したアクリル系共重合体（Ｍｗ＝７０万）とを、オキシムエステル化合物：アクリル系共重合体の質量比５：１００にて混合して、放射線硬化型の粘着剤を調製した。この粘着剤を５０μｍのＰＥＥＫフィルムに塗布し、粘着剤中の溶媒を１２０℃で揮発させて放射線硬化型粘着剤層（厚さ２０ｕｍ）としたリフロー対応ダイシングテープを作製した。 An acrylic copolymer (Mw = 700,000 ) were mixed at a mass ratio of oxime ester compound:acrylic copolymer of 5:100 to prepare a radiation-curable adhesive. This adhesive was applied to a 50 μm PEEK film, and the solvent in the adhesive was evaporated at 120° C. to produce a reflow-compatible dicing tape with a radiation-curable adhesive layer (thickness: 20 μm).
実施例３
光重合開始剤として配合した実施例２のオキシムエステル化合物を、下記のオキシムエステル化合物（分子量４４５、Irugacure OXE01、BASF社製）に変更した以外は、実施例２と同様にしてリフロー対応ダイシングテープを作製した。
A reflow compatible dicing tape was prepared in the same manner as in Example 2, except that the oxime ester compound of Example 2 blended as a photopolymerization initiator was changed to the following oxime ester compound (molecular weight 445, Irugacure OXE01, manufactured by BASF). Created.
実施例４
光重合開始剤として配合した実施例２のオキシムエステル化合物を、下記のオキシムエステル化合物（分子量５１５）に変更した以外は、実施例２と同様にしてリフロー対応ダイシングテープを作製した。なお、実施例４のオキシムエステル化合物は、窒素雰囲気下、塩化アルミニウム１０．４ｇ（７８ミリモル）及び二塩化エタン３３．０ｇを仕込み、氷冷下で酸クロリド３６ミリモル、続いてニトロカルバゾール化合物３０ミリモル及び二塩化エタン３３．０ｇを徐々に滴下し、５℃で３０分間撹拌した。反応液を氷水にあけ、油水分離を行った。脱溶媒して、アシル体を得た。窒素気流下、得られたアシル体の２０ミリモル、塩酸ヒドロキシルアミン２．１ｇ（３０ミリモル）、及びジメチルホルムアミド１６．９ｇを仕込み、８０℃で１時間撹拌した。室温に冷却して油水分離を行った。溶媒を留去して、残さに酢酸ブチル２５．４ｇ、続いて無水酢酸２．４５ｇ（２４ミリモル）を加えて９０℃で１時間撹拌し、室温に冷却した。５％水酸化ナトリウム水溶液で中和し、油水分離、脱溶媒、酢酸エチルからの再結晶を経て、目的物である下記のオキシムエステル化合物を得た。
A reflow compatible dicing tape was produced in the same manner as in Example 2, except that the oxime ester compound of Example 2 blended as a photopolymerization initiator was changed to the following oxime ester compound (molecular weight 515). The oxime ester compound of Example 4 was prepared by adding 10.4 g (78 mmol) of aluminum chloride and 33.0 g of ethane dichloride under a nitrogen atmosphere, and adding 36 mmol of acid chloride under ice cooling, followed by 30 mmol of a nitrocarbazole compound. Then, 33.0 g of ethane dichloride was gradually added dropwise, and the mixture was stirred at 5° C. for 30 minutes. The reaction solution was poured into ice water to separate oil and water. The acyl compound was obtained by removing the solvent. Under a nitrogen stream, 20 mmol of the obtained acyl compound, 2.1 g (30 mmol) of hydroxylamine hydrochloride, and 16.9 g of dimethylformamide were charged and stirred at 80° C. for 1 hour. The mixture was cooled to room temperature and oil and water were separated. The solvent was distilled off, and to the residue were added 25.4 g of butyl acetate, followed by 2.45 g (24 mmol) of acetic anhydride, stirred at 90° C. for 1 hour, and cooled to room temperature. After neutralization with a 5% aqueous sodium hydroxide solution, oil/water separation, solvent removal, and recrystallization from ethyl acetate, the target oxime ester compound shown below was obtained.
比較例１
光重合開始剤として配合した実施例１のα－ヒドロキシアセトフェノンの配合量を、α－ヒドロキシアセトフェノン：アクリル系共重合体の質量比１０：１００とした以外は、実施例１と同様にしてダイシングテープを作製した。Comparative example 1
A dicing tape was prepared in the same manner as in Example 1, except that the amount of α-hydroxyacetophenone blended as a photopolymerization initiator in Example 1 was changed to a mass ratio of α-hydroxyacetophenone:acrylic copolymer of 10:100. was created.
（１）Ｘ線光電子分光法（ＸＰＳ）にて測定した炭素量
作製したリフロー対応ダイシングテープをシリコンウエハに貼り合わせて紫外線（波長３６５ｎｍ）を１０００ｍＪ／ｃｍ２照射した後、２１０℃にて１０分の熱処理を行った。次に、リフロー対応ダイシングテープをシリコンウエハから剥離後、シリコンウエハのリフロー対応ダイシングテープが貼られていた面について、付着している成分全量中における炭素量をＸ線光電子分光法（ＸＰＳ）にて測定し、以下のように評価した。なお、ＸＰＳの装置はＰＨＩ Ｑｕａｎｔｅｓ（アルバック・ファイ社製）を使用し、励起Ｘ線は単色化Ａｌ－Ｋα線で脱出角度は４５°、ｗｉｄｅ ｓｃａｎ方式で１３５０～０ｅＶの範囲で測定を行った。分析領域は１００μｍφとした。
○：炭素量３０ｍｏｌ％以下
×：炭素量３０ｍｏｌ％超(1) Carbon content measured by X-ray photoelectron spectroscopy (XPS) After pasting the reflow compatible dicing tape prepared on a silicon wafer and irradiating it with ultraviolet rays (wavelength 365 nm) at 1000 mJ/ cm2 , it was heated to 210°C for 10 minutes. heat treatment was performed. Next, after peeling off the reflow compatible dicing tape from the silicon wafer, the amount of carbon in the total amount of components adhered to the side of the silicon wafer where the reflow compatible dicing tape was pasted was measured using X-ray photoelectron spectroscopy (XPS). It was measured and evaluated as follows. The XPS equipment used was PHI Quantes (manufactured by ULVAC-PHI), and the excitation X-rays were monochromatic Al-Kα rays, the escape angle was 45°, and measurements were performed in the range of 1350 to 0 eV using the wide scan method. . The analysis area was 100 μmφ.
○: Carbon content 30 mol% or less ×: Carbon content more than 30 mol%
（２）アウトガス低減性
上記した２１０℃にて１０分の熱処理を行った際におけるアウトガスの発生の有無を、上記熱処理後における放射線硬化型粘着剤層に生じた気泡を目視及び光学顕微鏡にて観察することで評価した。
○：気泡の発生ほとんどなし
△：若干の気泡あり
×：著しく気泡あり(2) Reduction of outgas The presence or absence of outgas during the above-mentioned heat treatment at 210°C for 10 minutes was determined by visually observing and using an optical microscope the bubbles generated in the radiation-curable adhesive layer after the above-mentioned heat treatment. It was evaluated by
○: Almost no air bubbles △: Some air bubbles ×: Significant air bubbles
（３）チップ飛び防止性
上記した２１０℃にて１０分の熱処理を行った後、シリコンウエハを個片化するダイシング工程時においてダイシングテープから剥離したチップの個数を測定し、以下のように評価した。
◎：ダイシングテープから剥離したチップなし
○：ダイシングテープから剥離したチップがあるが、その割合は１％以下
△：ダイシングテープから剥離したチップの割合が１％超５％以下
×：ダイシングテープから剥離したチップの割合が５％超(3) Prevention of chip flying After heat treatment at 210°C for 10 minutes as described above, the number of chips peeled off from the dicing tape during the dicing process to separate the silicon wafer into pieces was measured and evaluated as follows. did.
◎: No chips separated from the dicing tape ○: There are chips separated from the dicing tape, but the percentage is less than 1% △: The percentage of chips separated from the dicing tape is more than 1% and less than 5% ×: Separated from the dicing tape More than 5% of chips
評価結果を表１に示す。 The evaluation results are shown in Table 1.
一方で、Ｘ線光電子分光法にて測定した際の炭素量が３０ｍｏｌ％超である比較例１では、アウトガス低減性が得られず、ダイシングテープから剥離したチップの割合が５％超となってしまった。 On the other hand, in Comparative Example 1, in which the carbon content as measured by X-ray photoelectron spectroscopy was more than 30 mol%, outgas reduction properties were not obtained, and the proportion of chips peeled off from the dicing tape was more than 5%. Oops.
Claims (6)
前記放射線硬化型粘着剤層にシリコンウエハを貼りあわせた後に、放射線照射してから２１０℃にて１０分の加熱処理をし、該加熱処理後に前記放射線硬化型粘着剤層から前記シリコンウエハを剥離させた際における前記シリコンウエハの貼り合わせ面をＸ線光電子分光法にて測定した際の炭素量が、３０ｍｏｌ％以下であり、
前記放射線硬化型粘着剤層が光重合開始剤を含み、前記光重合開始剤がオキシムエステル化合物であるリフロー対応ダイシングテープ。 comprising a base material layer and a radiation-curable adhesive layer provided on the base material layer,
After bonding the silicon wafer to the radiation-curable adhesive layer, heat treatment is performed at 210° C. for 10 minutes after irradiation with radiation, and after the heat treatment, the silicon wafer is peeled from the radiation-curable adhesive layer. The amount of carbon when the bonded surface of the silicon wafer is measured by X-ray photoelectron spectroscopy is 30 mol% or less,
A reflow compatible dicing tape, wherein the radiation-curable adhesive layer contains a photopolymerization initiator, and the photopolymerization initiator is an oxime ester compound .
The adhesive strength of the radiation-curable adhesive layer measured in accordance with JIS Z0237 after being irradiated with 1000 mJ/cm 2 of radiation with a wavelength of 350 nm and then heat-treated at 210°C for 10 minutes is 0. The reflow compatible dicing tape according to any one of claims 1 to 5 , which has a width of 3N/25mm or more and 2.0N/25mm or less.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2018226963 | 2018-12-04 | ||
| JP2018226963 | 2018-12-04 | ||
| PCT/JP2019/047232 WO2020116448A1 (en) | 2018-12-04 | 2019-12-03 | Reflow-compatible dicing tape |
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| JPWO2020116448A1 JPWO2020116448A1 (en) | 2021-10-14 |
| JP7407714B2 true JP7407714B2 (en) | 2024-01-04 |
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| KR (1) | KR102403288B1 (en) |
| CN (1) | CN111868887A (en) |
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| JP7392401B2 (en) | 2018-11-08 | 2023-12-06 | 三菱ケミカル株式会社 | Adhesive resin composition, adhesive sheet, active energy ray-curable adhesive sheet, optical member, laminate for image display device, and image display device |
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| JP2012033636A (en) | 2010-07-29 | 2012-02-16 | Nitto Denko Corp | Thermal peeling sheet integrated film for semiconductor rear face, method of collecting semiconductor element, and method of manufacturing semiconductor device |
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| WO2011058995A1 (en) * | 2009-11-13 | 2011-05-19 | 日立化成工業株式会社 | Semiconductor device, method for manufacturing semiconductor device, and semiconductor wafer provided with adhesive layer |
| KR101143109B1 (en) * | 2010-08-05 | 2012-05-08 | 후루카와 덴키 고교 가부시키가이샤 | Adhesive film and semiconductor wafer processing tape |
| JP5834606B2 (en) * | 2011-08-05 | 2015-12-24 | Dic株式会社 | UV-curable adhesive resin composition, adhesive and laminate |
| JP6391597B2 (en) * | 2014-08-29 | 2018-09-19 | 古河電気工業株式会社 | Conductive adhesive composition |
| JP2016204406A (en) * | 2015-04-15 | 2016-12-08 | 藤森工業株式会社 | Adhesive layer and adhesive film |
| JP6724907B2 (en) * | 2015-05-01 | 2020-07-15 | コニカミノルタ株式会社 | Long gas barrier film and method for producing the same, short gas barrier film and method for producing the same |
| JP2017125093A (en) * | 2016-01-12 | 2017-07-20 | 積水化学工業株式会社 | Processing method of semiconductor protective tape and wafer |
| JP6827877B2 (en) * | 2017-04-28 | 2021-02-10 | サンアロマー株式会社 | Polypropylene resin composition for hollow molding, its manufacturing method and hollow molded product |
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- 2019-12-03 JP JP2020537799A patent/JP7407714B2/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2008027960A (en) | 2006-07-18 | 2008-02-07 | Nitto Denko Corp | Heat-resistance dicing tape or sheet |
| JP2010129701A (en) | 2008-11-26 | 2010-06-10 | Nitto Denko Corp | Dicing die-bonding film and method for producing semiconductor device |
| JP2011054953A (en) | 2009-08-05 | 2011-03-17 | Furukawa Electric Co Ltd:The | Adhesive film, and tape for processing semiconductor wafer |
| JP2012033636A (en) | 2010-07-29 | 2012-02-16 | Nitto Denko Corp | Thermal peeling sheet integrated film for semiconductor rear face, method of collecting semiconductor element, and method of manufacturing semiconductor device |
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| CN111868887A (en) | 2020-10-30 |
| KR20200138374A (en) | 2020-12-09 |
| JPWO2020116448A1 (en) | 2021-10-14 |
| KR102403288B1 (en) | 2022-05-30 |
| WO2020116448A1 (en) | 2020-06-11 |
| TW202028395A (en) | 2020-08-01 |
| TWI753328B (en) | 2022-01-21 |
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