CN111868887A - Reflow corresponding cutting crystal belt - Google Patents
Reflow corresponding cutting crystal belt Download PDFInfo
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- CN111868887A CN111868887A CN201980020184.9A CN201980020184A CN111868887A CN 111868887 A CN111868887 A CN 111868887A CN 201980020184 A CN201980020184 A CN 201980020184A CN 111868887 A CN111868887 A CN 111868887A
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- 238000005520 cutting process Methods 0.000 title claims abstract description 6
- 239000013078 crystal Substances 0.000 title description 6
- 239000012790 adhesive layer Substances 0.000 claims abstract description 53
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 27
- 239000010703 silicon Substances 0.000 claims abstract description 27
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 230000005855 radiation Effects 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000010410 layer Substances 0.000 claims abstract description 16
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 82
- -1 oxime ester compound Chemical class 0.000 claims description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 54
- 239000000853 adhesive Substances 0.000 claims description 40
- 230000001070 adhesive effect Effects 0.000 claims description 39
- 239000003999 initiator Substances 0.000 claims description 28
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 12
- 238000011109 contamination Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 272
- 125000000217 alkyl group Chemical group 0.000 description 111
- 125000005843 halogen group Chemical group 0.000 description 86
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 76
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 70
- 125000000623 heterocyclic group Chemical group 0.000 description 67
- 125000003710 aryl alkyl group Chemical group 0.000 description 66
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 61
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 59
- 125000004093 cyano group Chemical group *C#N 0.000 description 59
- 125000003118 aryl group Chemical group 0.000 description 41
- 239000004593 Epoxy Substances 0.000 description 32
- 125000002947 alkylene group Chemical group 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 24
- 150000002430 hydrocarbons Chemical group 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
- 125000004430 oxygen atom Chemical group O* 0.000 description 13
- 150000007519 polyprotic acids Polymers 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003342 alkenyl group Chemical group 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
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052711 selenium Inorganic materials 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000010943 off-gassing Methods 0.000 description 7
- 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
- 150000001721 carbon Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229920002530 polyetherether ketone Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 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
- 239000011976 maleic acid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-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
- 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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-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
- 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
- 239000004697 Polyetherimide Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000003855 acyl compounds Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-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
- 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
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 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
- 239000006185 dispersion Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 229960005237 etoglucid Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-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
- 125000002560 nitrile group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 125000005591 trimellitate group Chemical group 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- 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
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004021 humic acid Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 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
- 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
- 239000011159 matrix material Substances 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
- 229940095102 methyl benzoate Drugs 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
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-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
- 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
- SPIGUVVOJXSWNX-UHFFFAOYSA-N n-(oxomethylidene)thiohydroxylamine Chemical compound SN=C=O SPIGUVVOJXSWNX-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
- 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
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 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
- 238000006146 oximation reaction Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols 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
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide 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
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 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
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000013076 target substance Substances 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
- 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
- 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
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical class NC(=O)OC=C LVLANIHJQRZTPY-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
- 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]
- 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
- 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
- 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
Abstract
The invention aims to provide a reflow die-cutting tape which can prevent the generation of outgas from a radiation-curable adhesive layer and has excellent contamination resistance. A reflow die-cut tape comprising a base material layer and a radiation-curable adhesive layer provided on the base material layer, wherein a silicon wafer is bonded to the radiation-curable adhesive layer, then irradiated with a radiation, and then subjected to a heat treatment at 210 ℃ for 10 minutes, and the silicon wafer is peeled from the radiation-curable adhesive layer after the heat treatment, and wherein the amount of carbon at the bonded surface of the silicon wafer is 30 mol% or less as measured by X-ray photoelectron spectroscopy.
Description
Technical Field
The present invention relates to a reflow-aligned dicing tape used in a semiconductor manufacturing process.
Background
In recent years, with the improvement of performance in semiconductor structures, the density of chips and electrical connection points has been increased. Conventionally, electric wires are used for electrical connection, but in order to improve connection reliability, connection with solder is advanced, and a step of melting solder balls (reflow step) is used in the connection step. Since the chip is subjected to a high temperature exceeding 200 ℃ in the reflow step, the dicing tape as the support is also required to have heat resistance capable of withstanding a high temperature exceeding 200 ℃.
As a dicing tape that can cope with a high temperature exceeding 200 ℃, for example, patent document 1 discloses a tape using a heat-resistant adhesive layer, which is cured by a crosslinking reaction induced by irradiation with an energy ray. As shown in patent document 1, by irradiating energy rays before the reflow step, a crosslinking reaction of the resin component of the adhesive layer occurs, so-called adhesive residue in which adhesive (adhesive) remains on the bonding surface of the silicon wafer as the adherend can be improved.
However, when the resin component of the adhesive layer is crosslinked by irradiation with an energy ray, the photopolymerization initiator contained in the adhesive layer is broken to reduce the molecular weight, and outgassing is caused. If the dicing step of singulating the silicon wafer is performed after the energy ray irradiation through the reflow step, a problem of so-called chip scattering, in which the chips are not fixed and are peeled off from the dicing tape, may occur due to the floating caused by the outgassing generated by the adhesive.
Thus, the tape subjected to the reflow step is peeled off from the silicon wafer before the dicing step, and the other dicing step tape is bonded to the silicon wafer. Such replacement and attachment of the tape leads to deterioration in productivity and increase in waste, and therefore improvement is desired.
Documents of the prior art
Patent document
Patent document 1: japanese Kokai publication No. 2009-538389
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of the above problems, and an object of the present invention is to provide a reflow die-cutting tape which can suppress the generation of outgas from a radiation-curable adhesive layer and has excellent contamination resistance.
Means for solving the problems
The present inventors have made intensive studies on physical properties, materials, and the like of a heat-resistant adhesive tape in order to achieve the above object. As a result, the present inventors have found that the following radiation-curable adhesive agent layer can achieve the above object, and have completed the present invention. The radiation-curable adhesive layer is a tape comprising a radiation-curable adhesive, and the amount of carbon at the bonded surface of the silicon wafer is 30 mol% or less as measured by X-ray photoelectron spectroscopy when a silicon wafer as an adherend is bonded to the radiation-curable adhesive layer, irradiated with radiation, and then subjected to heat treatment at 210 ℃ for 10 minutes to peel the silicon wafer from the radiation-curable adhesive layer.
The gist of the configuration of the present invention is as follows.
[1] A reflow die-cutting tape comprises a substrate layer and a radiation-curable adhesive layer disposed on the substrate layer,
And a step of bonding a silicon wafer to the radiation-curable adhesive layer, irradiating the silicon wafer with a radiation, and then performing a heat treatment at 210 ℃ for 10 minutes, wherein the silicon wafer is peeled from the radiation-curable adhesive layer after the heat treatment, and wherein the amount of carbon in the bonded surface of the silicon wafer is 30 mol% or less as measured by an X-ray photoelectron spectroscopy.
[2] The reflow die-cut tape according to [1], wherein the radiation-curable adhesive layer comprises: a polymerizable compound having an ethylenically unsaturated bond, 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 an anion, and a photopolymerization initiator.
[3] The reflow-compatible dicing tape according to [2], wherein the polymer of the polymerizable compound having an ethylenically unsaturated bond comprises a (meth) acrylic polymer, and the (meth) acrylic polymer is a polymer of a monomer containing (meth) acrylic acid and/or a (meth) acrylate.
[4] The reflow-aligned sliced ribbon according to [2] or [3], wherein the photopolymerization initiator is an oxime ester compound.
[5] The reflow-compatible sliced ribbon 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]Such as [1]]～[6]The reflow-processed crystal slicing tape of any one of the above items, wherein the thickness is 1000mJ/cm2The radiation curable adhesive layer is irradiated with a radiation ray having a wavelength of 350nm, and then subjected to a heat treatment at 210 ℃ for 10 minutes, and then the adhesive force measured according to JIS Z0237 is 0.3N/25mm width or more and 2.0N/25mm width or less.
In the present invention, the radiation-curable adhesive layer of the sliced tape bonded to the silicon wafer before the reflow step is irradiated with radiation in advance, and the molecular weight of the main component constituting the radiation-curable adhesive layer is increased by a crosslinking reaction or the like. Even if the sliced tape contains a low-molecular component, the low-molecular component is incorporated into the main skeleton when the molecular weight of the main component constituting the radiation-curable adhesive layer increases, and the volatile component can be reduced. Therefore, outgas components can be reduced in the reflow-aligned sliced ribbon of the present invention.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the aspect of the present invention, when the silicon wafer is peeled off from the dicing tape after the reflow step, so-called adhesive residue in which the adhesive of the radiation-curable adhesive layer remains on the silicon wafer can be prevented, and also, the silicon wafer can be prevented from floating from the dicing tape due to the outgas generated from the radiation-curable adhesive layer, and thus, the chips can be prevented from scattering.
Detailed Description
The reflow of the present invention is described below with respect to the sliced ribbon. The reflow die-cut tape of the present invention includes a base material layer and a radiation-curable adhesive layer provided on the base material layer. The radiation-curable adhesive layer can be formed by coating a radiation-curable adhesive onto a base material layer.
The radiation-curable adhesive layer for reflow-to-dicing tape of the present invention was formed at 1000mJ/cm2Irradiated with a radiation having a wavelength of 350nm, and subjected to a heat treatment at 210 ℃ for 10 minutes, and then subjected to a thermal treatmentThe adhesive force measured by IS Z0237 IS not particularly limited, and the lower limit value thereof IS preferably 0.3N/25mm wide or more, and particularly preferably 0.5N/25mm wide or more, from the viewpoint of reliably preventing so-called chip scattering in which chips are scattered because chips cannot be fixed in the dicing step, and peeling occurs in the step including transportation. In addition, the upper limit value of the adhesive force is preferably 2.0N/25mm wide or less, and particularly preferably 1.5N/25mm wide or less, from the viewpoint of reliably preventing so-called adhesive residue in which a part of the radiation-curable adhesive layer adheres to an adherend when peeling off the reflow-compatible dicing tape.
The material of the base layer is not particularly limited. However, the base material layer is heated to 210 ℃ or higher together with the radiation-curable adhesive layer. Therefore, the substrate layer needs to have sufficient heat resistance against the heating conditions. Thus, examples of preferable base material layers include a polyethylene terephthalate (PET) film, a polyethylene naphthalate (PEN) film, a polyether sulfone (PES) film, a polyether imide (PEI) film, a Polysulfone (PSF) film, a polyphenylene sulfide (PPS) film, a polyether ether ketone (PEEK) film, a Polyarylate (PAR) film, an aramid film, a polyimide film, a liquid crystal polymer (PCP) film, and the like. Among these, a Polyetheretherketone (PEEK) film is particularly preferable in terms of grippability in the dicing step.
The thickness of the base material layer may be appropriately selected depending on the use conditions and the like, and is preferably in the range of 5 to 250 μm, for example. By setting the thickness of the base material layer within the above numerical range, breakage or breakage of the reflow-corresponding dicing tape can be prevented, and excellent handleability can be obtained.
In the radiation-curable adhesive layer, an adherend is bonded to the radiation-curable adhesive layer, then radiation irradiation is performed, then heating treatment is performed at 210 ℃ for 10 minutes, and after the heating treatment, the adherend is peeled off from the radiation-curable adhesive layer, and in this case, the amount of carbon at the bonded surface of the adherend is 30 mol% or less as measured by an X-ray photoelectron spectroscopy method. The conditions for the irradiation of radiation include 1000mJ/cm2Radiation having a wavelength of 350nm is irradiated.
The radiation-curable adhesive layer reduces the amount of carbon on the release surface of the adherend to 30 mol% or less even when subjected to a heat treatment at 210 ℃ for 10 minutes after radiation irradiation. Therefore, the adhesive of the radiation-curable adhesive layer can be prevented from remaining on the adherend, and the adherend can be prevented from floating from the dicing tape. The amount of carbon on the release surface of the adherend is not particularly limited as long as it is 30 mol% or less, and is particularly preferably 25 mol% or less.
The amount of carbon on the release surface of the adherend is the ratio of the total amount of components adhering to the release surface of the adherend.
The radiation-curable adhesive layer contains an adhesive as an adhesive component. The adhesive comprises: a polymerizable compound having an ethylenically unsaturated bond, 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 an anion, and a photopolymerization initiator as main components.
Polymerizable compound having ethylenically unsaturated bond
The polymerizable compound having an ethylenically unsaturated bond to be blended as the main component of the adhesive is not particularly limited, and a compound blended in a conventional photosensitive composition can be used. Examples of the polymerizable compound having an ethylenically unsaturated bond include: unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene fluoride, and tetrafluoroethylene; carboxylic acids having an ethylenically unsaturated bond such as (meth) acrylic acid, α -chloro (meth) acrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, humic acid, crotonic acid, methacrylic acid, vinylacetic acid, allylacetic acid, cinnamic acid, sorbic acid, mesaconic acid, and the like; mono (meth) acrylates of polymers having carboxyl groups and hydroxyl groups at both ends, such as succinic acid mono [2- (meth) acryloyloxyethyl ester ], phthalic acid mono [2- (meth) acryloyloxyethyl ester ], and ω -carboxy polycaprolactone mono (meth) acrylate; unsaturated polybasic acids such as hydroxyethyl (meth) acrylate-maleic acid ester, hydroxypropyl (meth) acrylate-maleic acid ester, dicyclopentadiene-maleic acid ester, and polyfunctional (meth) acrylate having 1 carboxyl group and 2 or more (meth) acryloyl groups; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, the following compounds No. A1 to 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, dimethylaminoethyl (meth) acrylate, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, poly (meth) acrylate, Butoxyethoxyethyl (meth) acrylate, ethylhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (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, and mixtures thereof, (meth) acrylates as esters of (meth) acrylic acid with alcohols or phenols, such as pentaerythritol tri (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, tris [ (meth) acryloylethyl ] isocyanurate, and polyester (meth) acrylate oligomers.
[ CHEM 1 ]
Compound No. A1
[ CHEM 2 ]
Compound No. A2
[ CHEM 3 ]
Compound No. a3
[ CHEM 4 ]
Compound No. A4
Examples of other polymerizable compounds having an ethylenically unsaturated bond include: metal salts of (meth) acrylic acid such as zinc (meth) acrylate and magnesium (meth) acrylate; anhydrides of unsaturated polybasic acids such as maleic anhydride, itaconic anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2, 5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adducts, dodecenylsuccinic anhydride, and methylhumic anhydride; amides of (meth) acrylic acid and amine compounds such as (meth) acrylamide, methylenebis (meth) acrylamide, diethylenetriamine tri (meth) acrylamide, xylylenebis (meth) acrylamide, α -chloro (meth) acrylamide, and N-2-hydroxyethyl (meth) acrylamide; unsaturated aldehydes such as acrolein; unsaturated nitriles such as (meth) acrylonitrile, α -chloroacrylonitrile, vinylidene cyanide, and allylnitrile; unsaturated aromatic compounds such as styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether, and vinylbenzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone and vinylpiperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, and allyl glycidyl ether; unsaturated imides such as maleimide, N-phenylmaleimide and N-cyclohexylmaleimide; indenes such as indene and 1-methylindene; aliphatic conjugated dienes such as 1, 3-butadiene, isoprene and chloroprene; macromonomers having a mono (meth) acryloyl group at the terminal of the polymer molecular chain, such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane; vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphate, isocyanurate triallyl ester, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, vinyl carbamate compounds of hydroxyl group-containing vinyl monomers and polyisocyanate compounds, vinyl epoxy compounds of hydroxyl group-containing vinyl monomers and polyepoxides. 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.
Examples of other polymerizable compounds having an ethylenically unsaturated bond include: a polybasic acid-modified unsaturated monocarboxylic acid-based epoxy compound obtained by reacting an unsaturated monocarboxylic acid with an epoxy compound and reacting the resulting hydroxyl group with a polybasic acid and/or a polybasic acid anhydride.
Examples of the epoxy compound that can be used for producing the polyacid-modified unsaturated monocarboxylic acid epoxy compound include epoxy compounds that are the compounds having a cyclic structure that reacts with a cation and/or an anion as described above. Examples of the unsaturated monocarboxylic acid that can be used for the preparation of the polybasic acid-modified unsaturated monocarboxylic acid epoxy compound include (meth) acrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl (meth) acrylate-maleic acid ester, hydroxypropyl (meth) acrylate-maleic acid ester, and dicyclopentadiene-maleic acid ester.
Examples of the polybasic acid that can be used for producing the polybasic acid-modified unsaturated monocarboxylic epoxy compound include biphenyltetracarboxylic acid, tetrahydrophthalic acid, succinic acid, diphthalic 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-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic acid, trialkyltetrahydrophthalic acid-maleic acid adduct, dodecenylsuccinic acid, and methylhumic acid. Examples of the polybasic acid anhydride include anhydrides of the above polybasic acids, ethylene glycol dianhydro trimellitate, and glycerol dianhydro trimellitate.
The molar ratio of the epoxy compound, the unsaturated monocarboxylic acid, the polybasic acid and/or the polybasic acid anhydride in the reaction for producing the polybasic acid-modified unsaturated monocarboxylic acid epoxy compound is, for example, preferably 0.1 to 1.0 number of the polybasic acid and/or the polybasic acid anhydride per 1 hydroxyl group of the epoxy adduct in the epoxy adduct having a structure in which 0.1 to 1.0 number of the carboxyl group of the unsaturated monocarboxylic acid is added to 1 epoxy group of the epoxy compound. The reaction of the epoxy compound, the unsaturated monocarboxylic acid, the polybasic acid and/or the polybasic acid anhydride may be carried out according to a conventional method.
Polymer of polymerizable compound having ethylenically unsaturated bond
Examples of the polymer of the polymerizable compound having an ethylenically unsaturated bond to be blended as the main component of the adhesive include a polymer or a copolymer of the polymerizable compound having an ethylenically unsaturated bond. Among them, a (meth) acrylic polymer is preferable in that the control of the molecular weight is easy and the adjustment of the adhesive force is easy, and the (meth) acrylic polymer is a polymer of a monomer containing (meth) acrylic acid and/or the above (meth) acrylic acid ester.
Compounds having cyclic structure reactive with cation and/or anion
Examples of the compound having a cyclic structure which reacts with a cation and/or an anion and is blended as a main component of the adhesive include compounds having a 3-membered ring structure containing an oxygen atom such as epoxy compounds and glycidyl ethers. Examples of the epoxy compound include: novolac-type epoxy compounds such as phenol novolac-type epoxy compounds, biphenol novolac-type epoxy compounds, cresol novolac-type epoxy compounds, bisphenol a novolac-type epoxy compounds, dicyclopentadiene novolac-type epoxy compounds, and the like; epoxy compounds such as bisphenol type epoxy compounds and polyphenylmethane type epoxy compounds having a polyfunctional epoxy group, and alicyclic epoxy compounds such as 3, 4-epoxy-6-methylcyclohexylmethyl-3, 4-epoxy-6-methylcyclohexanecarboxylate, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexylcarboxylate, and 1-epoxyethyl-3, 4-epoxycyclohexane; glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, and glycidyl dimer acid; glycidyl amines such as tetraglycidyl diaminodiphenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1, 3-diglycidyl-5, 5-dimethylhydantoin and triglycidyl isocyanurate; dioxide compounds such as dicyclopentadiene dioxide; a naphthalene type epoxy compound; triphenylmethane-type epoxy compounds; dicyclopentadiene type epoxy compounds, and the like.
Examples of the glycidyl ether 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-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-tris (glycidoxymethyl) propane, 1,1, 1-tris (glycidoxymethyl) ethane, 1,1, 1-tris (glycidoxymethyl) methane, 1, 4-butanediol diglycidyl ether, 1, 2-dimethyl-1, 3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, 1, 4-cyclohexanedimethanol diglycidyl ether, 1,1,1,1, 1,1, 1-tetrakis (glycidoxymethyl) methane, and the like.
Examples of the compound having a cyclic structure which reacts with a cation and/or an anion and is blended as a main component of the adhesive include a compound having a 4-membered ring structure containing an oxygen atom such as oxetane. These compounds may be used alone or in combination of two or more.
Photopolymerization initiator
When the active energy ray is irradiated to the polymerizable compound having an ethylenically unsaturated bond to cause photocuring of the polymerizable compound having an ethylenically unsaturated bond, the photopolymerization initiator exerts an effect of promoting photocuring.
As the photopolymerization initiator, known polymerization initiators can be appropriately selected, and examples thereof include α -hydroxyacetophenone, α -aminoalkylphenone, benzophenone, phenylbiphenylketone, 1-hydroxy-1-benzoylcyclohexane, benzoin bismethyl ether, 1-benzyl-1-dimethylamino-1- (4' -morpholinobenzoyl) propane, 2-morpholino-2- (4' -methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethylanthraquinone, 4-benzoyl-4 ' -methylbenzophenone, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, and mixtures thereof, 2-hydroxy-2- (4 '-isopropyl) benzoylpropane, 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyl dichloromethane, methyl benzoylformate, 1, 7-bis (9' -acridinyl) heptane, 9-n-butyl-3, 6-bis (2 '-morpholinoisobutyryl) carbazole, 2-methyl-4, 6-bis (trichloromethyl) s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) s-triazine, 2-naphthyl-4, 6-bis (trichloromethyl) s-triazine, 2-bis (2-chlorophenyl) -4,5, 4', 5 '-tetraphenyl-1-2' -biimidazole, 4-azobisisobutyronitrile, methyl benzoate, Triphenylphosphine, benzoyl peroxide, and the like. Among them, preferred are α -hydroxyacetophenone and α -aminoalkylphenone.
Examples of the α -aminoalkylphenones include: a compound of the formula,
[ CHEM 5 ]
(in the formula, R1And R2Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is 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; alkenyl group having 2 to 12 carbon atoms, R1And R2May be linked to form a 3-to 6-membered ring,
R3and R4Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group or a nitro group; alkenyl group having 2 to 12 carbon atoms, R 3And R4Cyclic alkanes capable of being linked to form 3 to 6-membered rings,
R5、R6、R7and R8Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group; an alkyl group having 1 to 8 carbon atoms which is substituted or unsubstituted with a halogen atom; an aralkyl group having 7 to 30 carbon atoms which is 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,
R9、R10、R11、R12and R13Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group; an alkyl group having 1 to 8 carbon atoms which is substituted or unsubstituted with a halogen atom; aralkyl having 7 to 30 carbon atoms which is 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, -OR14、-O-CO-O-R15、-NR16R17、-SR18And R is9、R10、R11、R12And R13At least 1 of which is selected from nitro, -OR14、-O-CO-O-R15、-NR16R17、-SR18A group of (a) or (b),
R14、R15、R16、R17and R18Represents an alkyl group having 1 to 12 carbon atoms which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted with hydroxyl, carboxyl, halogen, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group or a nitro group; an alkenyl group having 2 to 12 carbon atoms; a heterocyclic group having 2 to 12 carbon atoms, a trialkylsilyl group or a triarylsilyl group, and the methylene chain in the alkyl group or aralkyl group may be replaced by-O-, -S-, -NR- 19-, -CO-O-, -O-CO-or-O-CO-O-, which alkyl may be terminated with an unsaturated bond,
R19represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is 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; an alkenyl group having 2 to 12 carbon atoms. )
A compound of the formula
[ CHEM 6 ]
(in the formula, R1And R2Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; quiltAn alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group-substituted or unsubstituted phenyl group; an aralkyl group having 7 to 30 carbon atoms which is 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; alkenyl group having 2 to 12 carbon atoms, R1And R2May be connected to form a 3-to 6-membered heterocyclic ring,
R3And R4Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl 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; an aralkyl group having 7 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group or a nitro group; alkenyl group having 2 to 12 carbon atoms, R3And R4Cyclic alkanes capable of being linked to form 3 to 6-membered rings,
R5、R6、R7、R8、R9、R10、R11and R12Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; an alkyl group having 1 to 8 carbon atoms which is substituted or unsubstituted with a halogen atom; an aralkyl group having 7 to 30 carbon atoms which is 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,
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 of 2 to 6, and n groups are the same. )
A compound of the formula.
[ CHEM 7 ]
(in the formula, R1And R2Each independently represents a hydrogen atom; by hydroxy, carboxyl, halogen, cyano or Nitro-substituted or unsubstituted alkyl with 1-12 carbon atoms; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is 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; alkenyl group having 2 to 12 carbon atoms, R1And R2May be connected to form a 3-to 6-membered heterocyclic ring,
R3and R4Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group or a nitro group; an alkenyl group having 2 to 12 carbon atoms; r3And R4Cyclic alkanes capable of being linked to form 3 to 6-membered rings,
R5、R6、R7and R8Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; an alkyl group having 1 to 8 carbon atoms which is substituted or unsubstituted with a halogen atom; an aralkyl group having 7 to 30 carbon atoms which is 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,
R9And R10Each independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a halogen atom or an alkyl group having 1 to 4 carbon atoms, and the same or different when n is 2 or more,
n represents a number of 1 to 12,
x is a divalent organic group, and 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 and aralkyl groups, and alkylene groups, may be replaced with-O-, -S-, -CO-O-, -O-CO-or-O-CO-O-. )
[ CHEM 8 ]
(in the formula, R1’And R2’Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is 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; alkenyl group having 2 to 12 carbon atoms, R1’And R2’May be connected to form a 3-to 6-membered heterocyclic ring,
R3’and R4’Each independently represents a hydrogen atom; an alkyl group having 1 to 12 carbon atoms, which is substituted or unsubstituted with a hydroxyl group, a carboxyl group, a halogen atom, a cyano group or a nitro group; phenyl substituted or unsubstituted by alkyl having 1 to 4 carbon atoms, hydroxyl, carboxyl, halogen atom, cyano or nitro; an aralkyl group having 7 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group, an alkylthio group having 1 to 4 carbon atoms, a carboxyl group, a halogen atom, a cyano group or a nitro group; alkenyl group having 2 to 12 carbon atoms, R 3’And R4’Cyclic alkanes capable of being linked to form 3 to 6-membered rings,
R5’、R6’、R7’and R8’Each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group; an alkyl group having 1 to 8 carbon atoms which is substituted or unsubstituted with a halogen atom; an aralkyl group having 7 to 30 carbon atoms which is 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,
the methylene chain in the above alkyl and aralkyl groups, and alkylene groups, may be replaced with-O-, -S-, -CO-O-, -O-CO-or-O-CO-O-. )
[ CHEM 9 ]
(in the formula, R12And R13Each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R14、R15、R16、R17、R18、R19、R20and R21Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or R22、OR23、SR24、NR25R26、COR27、SOR28、SO2R29Or CONR30R31，R16And R18May be bonded to each other to form a ring,
R22、R23、R24、R25、R26、R27、R28、R29、R30and R31Each independently represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
X2represents a single bond or CO, or a salt thereof,
X3represents an oxygen atom, a sulfur atom, a selenium atom, CR 32R33、CO、NR34Or PR35，
R32、R33、R34And R35Each independently represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R12、R13、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34and R35Wherein the methylene group in the alkyl group having 1 to 20 carbon atoms or the aralkyl group having 7 to 30 carbon atoms may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, and the methylene chain in the alkyl group or the aralkyl group may be interrupted by-O-. )
In addition, as the photopolymerization initiator, an oxime ester compound can be used. By using an oxime ester compound as the photopolymerization initiator, the occurrence of outgas can be reliably reduced.
Examples of the oxime ester compound include compounds of the following formula,
[ CHEM 10 ]
(in the formula, R1And R2Each independently represents R11、OR11、COR11、SR11、CONR12R13Or the CN group is selected from the group consisting of,
R11、R12and R13Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12and R13The hydrogen atoms of the substituents shown may further be OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22CN, halogen atom, or COOR21The substitution is carried out by the following steps,
R21、R22and R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R21、R22And R23The hydrogen atom of the substituent may be further substituted by CN,A halogen atom, a hydroxyl group or a carboxyl group,
R11、R12、R13、R21、R22and R23The alkylene moiety of the substituents shown may be replaced by-O-, -S-, -COO-, -OCO-, -NR-24-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-is interrupted 1 to 5 times,
R24represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12、R13、R21、R22and R23The alkyl moiety of the substituent may have a branched side chain or may be a cyclic alkyl group, and R is12And R13And R22And R23Each of which may together form a ring,
R3and R4Each independently represents R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11CN or a halogen atom,
a and b each independently represent an integer of 0 to 4,
x represents oxygen atom, sulfur atom, selenium atom, CR31R32、CO、NR33Or PR34，
R31、R32、R33And R34Each 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 aralkyl group having 7 to 30 carbon atoms,
R31、R32、R33and R34The alkyl moiety of the substituent may have a branched side chain or may be a cyclic alkyl group, R31、R32、R33And R34May each independently form a ring together with any adjacent benzene ring,
R5represents OH, COOH or a group represented by the following general formula (II).
[ CHEM 11 ]
(in the formula, Z1Is a bond representing-O-, -S-, -NR22-、-NR22CO-、-SO2-, -CS-, -OCO-or-COO-,
Z2is a bond represented by 1 to 3R6A substituted alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
Z2the alkylene moiety of the bond shown may be replaced by-O-, -S-, -COO-, -OCO-, -NR22-、-NR22COO-、-OCONR22-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times, Z2The alkylene moiety of the bond may have a branched side chain or may be a cyclic alkylene group,
R6is represented by OR41、SR41、CONR42R43、NR42COR43、OCOR41、COOR41、SCOR41、OCSR41、COSR41、CSOR41CN or a halogen atom,
R41、R42and R43Each 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 aralkyl group having 7 to 30 carbon atoms, R41、R42And R43The alkyl moiety of the substituent may have a branched side chain or may be a cyclic alkyl group, R42And R43May be formed together into a ring,
c represents an integer of 1 to 3. ))
A compound of the formula,
[ CHEM 12 ]
(in the formula, R1、R2And R3Each independently represents R11、OR11、COR11、SR11、CONR12R13Or CN, R11、R12And R13Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms OR a heterocyclic group having 2 to 20 carbon atoms, and the hydrogen atoms of the alkyl group, the aryl group, the aralkyl group and the heterocyclic group may be further OR-bonded 21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22CN, halogen atom, -CR21＝CR22R23、-CO-CR21＝CR22R23Carboxy, epoxy substituted, R21、R22And R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, wherein R is as defined above11、R12、R13、R21、R22And R23The methylene group of the alkylene portion of the substituent may be interrupted 1 to 5 times by an unsaturated bond, an ether bond, a thioether bond, an ester bond, a thioester bond, an amide bond or a urethane bond, the alkyl portion of the substituent may have a branched side chain or may be a cyclic alkyl group, the alkyl terminal of the substituent may be an unsaturated bond, and R may be R12And R13And R22And R23Each of which may together form a ring, R3May form a ring together with an adjacent benzene ring. R4And R5Each independently represents R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11CN, a halogen atom or a hydroxyl group, and a and b each independently represent 0 to 3. )
A compound of the formula
[ CHEM 13 ]
(in the formula, R1And R2Each independently represents R11、OR11、COR11、SR11、CONR12R13Or CN, R11、R12And R13Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms OR a heterocyclic group having 2 to 20 carbon atoms, and the hydrogen atoms of the alkyl group, the aryl group, the aralkyl group and the heterocyclic group may be further OR-bonded 21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22CN, halogen atom, -CR21＝CR22R23、-CO-CR21＝CR22R23Carboxy, epoxy substituted, R21、R22And R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, wherein R is as defined above11、R12、R13、R21、R22And R23The methylene group of the alkylene portion of the substituent may be interrupted 1 to 5 times by an unsaturated bond, an ether bond, a thioether bond, an ester bond, a thioester bond, an amide bond or a urethane bond, the alkyl portion of the substituent may have a branched side chain or may be a cyclic alkyl group, the alkyl terminal of the substituent may be an unsaturated bond, and R may be R12And R13And R22And R23Each may together form a ring. R3And R4Each independent earth surfaceShown as R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11CN, a halogen atom or a hydroxyl group, and a and b each independently represent 0 to 4. X represents oxygen atom, sulfur atom, selenium atom, CR31R32、CO、NR33Or PR34，R31、R32、R33And R34Each independently represents R11、OR11、COR11、SR11、CONR12R13Or CN, R3May form a ring structure by bonding-X-to 1 carbon atom of an adjacent benzene ring, or R3And R4May together form a ring, R31、R33And R34Each independently may form a ring together with any adjacent benzene ring. )
A compound of the formula,
[ CHEM 14 ]
(in the formula, R1And R2Each independently represents R 11、OR11、COR11、SR11、CONR12R13Or the CN group is selected from the group consisting of,
R11、R12and R13Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12and R13The hydrogen atoms of the indicated radicals may be further substituted by R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21A hydroxyl group, a nitro group, CN, a halogen atom, or COOR21The substitution is carried out by the following steps,
R21、R22and R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R21、R22and R23The hydrogen atoms of the indicated groups may be further substituted by hydroxyl, nitro, CN, halogen, hydroxyl or carboxyl groups,
R11、R12、R13、R21、R22and R23The alkylene moiety of the group shown may be substituted by-O-, -S-, -COO-, -OCO-, -NR24-、-NR24CO-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times under the condition that oxygen atoms are not adjacent,
R24represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12、R13、R21、R22、R23and R24The alkyl portion of the groups shown may have a branched side chain or may be a cyclic alkyl group,
R3represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R 3The alkyl moiety of the group may have a branched side chain or may be a cyclic alkyl group, and R is3And R7、R3And R8、R4And R5、R5And R6And R6And R7Each of which may together form a ring,
R3the hydrogen atoms of the indicated radicals may be further substituted by R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21A hydroxyl group, a nitro group, CN, a halogen atom, or COOR21The substitution is carried out by the following steps,
R4、R5、R6and R7Each independently represents R11、OR11、SR11、COR14、CONR15R16、NR12COR11、OCOR11、COOR14、SCOR11、OCSR11、COSR14、CSOR11A hydroxyl group, CN or halogen atom, R4And R5、R5And R6And R6And R7Each of which may together form a ring,
R14、R15and R16R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms14、R15And R16The alkyl part of the group may be a branched side chain or a cyclic alkyl group, R8Represents R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11A hydroxyl group, CN or a halogen atom,
n represents 0 or 1. )
A compound of the formula,
[ CHEM 15 ]
(in the formula, R1And R2R, OR, COR, SR, CONR 'R' OR CN, R 'and R' represent an alkyl group, an aryl group, an aralkyl group OR a heterocyclic group, which may be substituted with a halogen atom OR a heterocyclic group, among them, an alkyl group and an aralkyl groupThe alkylene moiety of (a) may be interrupted by an unsaturated bond, an ether bond, a thioether bond or an ester bond, and in addition, R 'and R' may together form a ring. R3And R4Each independently represents R, OR, SR, cyano, a halogen atom OR hydroxyl, and a and b each independently represents 0 to 4. X represents oxygen atom, sulfur atom, selenium atom, carbon atom, N-R 5Or P-R12，R5And R12Represents an alkyl group which may be interrupted by-O-, -S-, -CO-O-, -O-CO-, -CO-S-or-S-CO-, and R is R when X is a carbon atom3And R4Together form a ring, or R3Form a ring structure by bonding-X-to 1 carbon atom of an adjacent benzene ring, X is an oxygen atom, a sulfur atom, a selenium atom or P-R12When R is3May form a ring structure by bonding-X-to 1 carbon atom of an adjacent benzene ring, R3And R4Or may together form a ring R5And R12Each independently may form a ring together with an adjacent benzene ring. )
A compound of the formula,
[ CHEM 16 ]
(wherein X represents a halogen atom or an alkyl group, R1、R2And R3Each independently represents R, OR, COR, SR, CONRR ' OR CN, R and R ' represent an alkyl group, an aryl group, an aralkyl group OR a heterocyclic group, which may be substituted with a halogen atom and/OR a heterocyclic group, in which the alkylene moiety of the alkyl group and the aralkyl group may be interrupted by an unsaturated bond, an ether bond, a thioether bond, an ester bond, and R ' may together form a ring. Y is1Represents an oxygen atom, a sulfur atom or a selenium atom, A represents a heterocyclic group, m represents an integer of 0 to 4, p represents an integer of 0 to 5, and q represents 0 or 1. )
A compound of the formula,
[ CHEM 17 ]
(in the formula, R1And R2Each independently represents R 11、OR11、COR11、SR11、CONR12R13Or CN, R11、R12And R13Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R11、R12And R13The hydrogen atoms of the substituents shown are sometimes OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22CN, halogen atom, or COOR21The substitution is carried out by the following steps,
R21、R22and R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R21、R22And R23The hydrogen atom of the substituent shown is sometimes substituted by CN, a halogen atom, a hydroxyl group or a carboxyl group,
R11、R12、R13、R21、R22and R23The alkylene moiety of the substituent shown is sometimes substituted by-O-, -S-, -COO-, -OCO-, -NR-24-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times, R24Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R11、R12、R13、R21、R22And R23In the case where the alkyl moiety of the substituent shown above has a branched side chain or is a cyclic alkyl group, and R is12And R13And R22And R23Each of which sometimes also together form a ring,
R3、L1、L2and L3Represents R11、OR11、SR11、COR14、CONR15R16、NR12COR11、OCOR11、COOR14、SCOR11、OCSR11、COSR14、CSOR11Hydroxy, nitro, CN or halogen atom, L 1And R3、R3And L2And L2And L3Each of which may together form a ring, R14、R15And R16Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R4Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R4In the case where the alkyl moiety of the group shown is present with a branched side chain or is a cyclic alkyl group, R4The hydrogen atoms of the groups shown are sometimes further substituted by R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、NR22COR21、OCOR21、COOR21、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22、SCOR21、OCSR21、COSR21、CSOR21A hydroxyl group, a nitro group, CN, a halogen atom, or COOR21And X represents a direct bond, CO or a group represented by the following general formula (I-A).
[ CHEM 18 ]
(in the formula, Z1And Z2A bond which is a single bond, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
Z1and Z2The alkylene moiety of the bond shown is sometimes also replaced by-O-, -S-, -COO-, -OCO-, -NR-24-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times, Z2The alkylene moiety of the bond shown may have a branched side chain or may be a cyclic alkylene group.
R5Represents R11、OR11、COR11、SR11、CONR12R13Or CN, R11、R12And R13The same as the above general formula (I). ))
[ CHEM 19 ]
(in the formula, R6、R7And R8Each independently represents R11、OR11、COR11、SR11、CONR12R13Or CN, R11、R12And R13In the same manner as in the above-mentioned general formula (I),
R9represents OH, COOH or a group represented by the following general formula (II-A),
y represents an oxygen atom, a sulfur atom, a selenium atom, CR31R32、CO、NR33Or PR34，
Alpha represents an integer of 1 to 10, R31、R32、R33And R34Each 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 aralkyl group having 7 to 30 carbon atoms,
R31、R32、R33and R34The alkyl moiety of the substituent shown may have a branched side chain or may be a cyclic alkylene group, R31、R32、R33And R34Each independently may form a ring together with any adjacent benzene ring.
[ CHEM 20 ]
(in the formula, Z3Is a bond representing-O-, -S-, -NR22-、-NR22CO-、-SO2-, -CS-, -OCO-or-COO-,
Z4is a bond represented by 1 to 3R10A substituted alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
Z4the alkylene moiety of the bond shown may also be replaced by-O-, -S-, -COO-, -OCO, -NR24-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times, Z4The alkylene moiety of the bond also may have a branched side chain or be a cyclic alkylene group, R 10Is represented by OR41、SR41、CONR42R43、NR42COR43、OCOR41、COOR41、SCOR41、OCSR41、COSR41、CSOR41CN or halogen atom, R41、R42And R43Each 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 aralkyl group having 7 to 30 carbon atoms, R41、R42And R43The alkyl moiety of the substituent shown may have a branched side chain or may be a cyclic alkylene group, R42And R43Sometimes they may form a ring together, and a represents an integer of 1 to 3. R22And R24The same as the above general formula (I). ))
A compound of the formula,
[ CHEM 21 ]
(in the formula, R1And R2Each independently represents a hydrogen atom, a halogen atom, or nitroA cyano group, a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R3、R4、R5、R6、R7、R8and R9(hereinafter, also referred to as R)3～R9) Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, or R10、OR10、SR10、NR11R12、COR10、SOR10、SO2R10Or CONR11R12，
R10、R11And R12Each independently represents a C1-20 hydrocarbon group or a C2-20 heterocyclic group, R11And R12Sometimes they are bonded to form a ring,
R1、R2、R10、R11and R12The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be substituted by a halogen atom, a nitro group, a cyano group, a hydroxyl group, or NR11R12A carboxyl group, (meth) acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group, carboxyl group or heterocyclic group-containing group, and methylene group in the hydrocarbon group having 2 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be replaced by-O-, -CO-, -COO-, -OCO-, -NR- 13-、-NR13CO-、-S-、-SO2-, -SCO-or-COS-substitution,
R13represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, R3And R4、R4And R5、R5And R6、R6And R7、R7And R8And R8And R9Sometimes they are bonded to form a ring. )
A compound of the formula,
[ CHEM 22 ]
(in the formula, R1、R2And R3Represents R, OR, COR, SR, CONRR' OR CN, R4And R ' represent a hydrogen atom or a methyl group, and R ' represent an alkyl group, an aryl group, an aralkyl group or a heterocyclic group, which may be substituted with a halogen atom or a heterocyclic group, wherein the alkylene portion of the alkyl group and the aralkyl group may be interrupted by an unsaturated bond, an ether bond, a thioether bond or an ester bond, and R ' may form a ring together. X represents identical or different halogen atoms or alkyl groups, Y1Represents an oxygen atom, a sulfur atom or a selenium atom, Y2Represents an alkanediyl group in which a carbon atom in the main chain thereof may be substituted by an oxygen atom, a represents an integer of 0 to 4, and q represents 0 or 1. )
A compound of the formula,
[ CHEM 23 ]
(in the formula, R1And R2Each independently represents R11、OR11、COR11、SR11、CONR12R13Or the CN group is selected from the group consisting of,
R11、R12and R13Each independently represents 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 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12And R13The hydrogen atom of the substituent may be further OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-NCOR22-OCOR23、-C(＝N-OR21)-R22、-C(＝N-OCOR21)-R22CN, halogen atom, or COOR21The substitution is carried out by the following steps,
R21、R22and R23Each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a carbon atom6 to 30 aryl groups, 7 to 30 aralkyl groups or 2 to 20 heterocyclic groups,
R21、R22and R23The hydrogen atom of the substituent shown may be further substituted with CN, a halogen atom, a hydroxyl group or a carboxyl group,
R11、R12、R13、R21、R22and R23The alkylene moiety of the substituent shown may be replaced by-O-, -S-, -COO-, -OCO-, -NR24-、-NR24COO-、-OCONR24-, -SCO-, -COS-, -OCS-or-CSO-is interrupted 1 to 5 times,
R24represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11、R12、R13、R21、R22and R23The alkyl moiety of the substituent may have a branched side chain or a cyclic alkyl group, and R is12And R13And R22And R23Each of which sometimes together form a ring,
Z1is a bond, represents a single bond, -O-, -S-, -NR-22-、-NR22CO-、-SO2-, -CS-, -OCO-or-COO-,
Z2a bond which is a single bond, an alkanediyl group having 1 to 20 carbon atoms, an aryldiyl group having 6 to 30 carbon atoms, an aralkyldiyl group having 7 to 30 carbon atoms or a 2-valent heterocyclic group having 2 to 20 carbon atoms,
Z2The alkylene moiety of the bond shown is sometimes replaced by-O-, -S-, -COO-, -OCO-, -NR-22-、-NR22COO-、-OCONR22-, -SCO-, -COS-, -OCS-or-CSO-are interrupted 1 to 5 times, Z2The alkylene portion of the bond shown may have a branched side chain, and may be a cyclic alkylene,
x represents a bond represented by the following chemical formula (I-A) or (I-B). )
[ CHEM 24 ]
(in the formulae (I-A) and (I-B),. phi.
A compound of the formula,
[ CHEM 25 ]
(in the formula, R1And R2Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R1and R2The alkyl or R having 1 to 20 carbon atoms1And R2The hydrogen atom of the heterocyclic group having 2 to 20 carbon atoms may be a halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl group, or CH2Substituted by CH-O-, mercapto, isocyanate or heterocyclic group, R1And R2The alkyl or R having 1 to 20 carbon atoms1And R2The methylene group in the group containing 2 to 20 carbon atoms of the heterocycle may be-O-, -CO-, -COO-, -OCO-, -NR-3-、-NR3CO-、-S-、-CS-、-SO2-, -SCO-, -COS-, -OCS-or CSO-,
R3Represents 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. )
A compound of the formula,
[ CHEM 26 ]
(in the formula, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11And R12(hereinafter, also referred to as R)1～R12) Each independently represents a group represented by the following general formula (II), a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group, R13、OR13、SR13、NR14R15、COR13、SOR13、SO2R13Or CONR14R15，R13、R14And R15Each independently represents 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, an aralkyl group having 7 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R13、R14and R15The hydrogen atom of the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group having 3 to 20 carbon atoms, the cycloalkylalkyl group having 4 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the aralkyl group having 7 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be substituted with 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 ether group, a mercapto group, an isocyanate group or a heterocyclic group, and R is a group represented by13、R14And R15The methylene group in the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group having 3 to 20 carbon atoms, the cycloalkylalkyl group having 4 to 20 carbon atoms, the aralkyl group having 7 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be-O-, -CO-, -COO-, -OCO-, -NR-or 16-、-NR16CO-、-S-、-CS-、-SO2-, -SCO-, -COS-, -OCS-or CSO-,
R16represents 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 an aralkyl group having 7 to 20 carbon atoms,
ring A1And ring A2Condensed to form an aromatic ring having 30 or less carbon atoms,
R1、R2、R3、R4、R5、R6、R7、R8、R9and R10(hereinafter, also referred to as R)1～R10) At least one of which is a group represented by the following general formula (II),
m is A1The number of desirable substituents is a positive integer below,
when m.gtoreq.2, there are a plurality of R11Sometimes it is different from each other in that,
n is A2The number of desirable substituents is a positive integer below,
when n.gtoreq.2, there are a plurality of R12Sometimes it is different from each other in that,
R1and R2、R2And R3、R3And R4、R4And R5、R6And R7、R7And R8、R8And R9、R9And R10、R11And R12May be bonded to form a ring, and when m.gtoreq.2, R11And R11May be bonded to form a ring, and when n.gtoreq.2, R12And R12Sometimes they are bonded to form a ring.
[ CHEM 27 ]
(in the formula, R17And R18Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, 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, an aralkyl group having 7 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R17And R18The alkyl group having 1 to 20 carbon atoms, the cycloalkyl group having 3 to 20 carbon atoms, the cycloalkylalkyl group having 4 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, the aralkyl group having 7 to 20 carbon atoms or the aralkyl group having 2 to 20 carbon atoms is describedThe hydrogen atom of the heterocyclic group-containing group is sometimes substituted with a halogen atom, nitro group, cyano group, hydroxyl group, amino group, carboxyl group, methacryloyl group, acryloyl group, epoxy group, vinyl ether group, mercapto group, isocyanate group or heterocyclic group-containing group, R17And R18The methylene group in the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group having 3 to 20 carbon atoms, the cycloalkylalkyl group having 4 to 20 carbon atoms, the aralkyl group having 7 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be-O-, -CO-, -COO-, -OCO-, -NR-or19-、-NR19CO-、-S-、-CS-、-SO2-, -SCO-, -COS-, -OCS-or CSO-,
R19represents 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 an aralkyl group having 7 to 20 carbon atoms, and k represents 0 or 1. ))
A compound of the formula and the like.
[ CHEM 28 ]
(in the formula, R1、R2、R3、R4、R5、R6、R7、R8、R9And R10(hereinafter, also referred to as R) 1～R10) Each independently represents a group represented by the following general formula (II), a hydrogen atom, a halogen atom, a nitro group, a nitrile group, a cyano group, a hydroxyl group, a carboxyl group, a formyl group, a sulfo group, R13、OR13、SR13、NR14R15、COR13、SOR13、SO2R13Or CONR14R15，
R13、R14And R15Each independently represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R13、R14and R15The alkyl group or carbon having 1 to 20 carbon atomsThe hydrogen atom of the heterocyclic group having 2 to 20 atoms may be substituted by a group represented by the following general formula (II), 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 ether group, a mercapto group, an isocyanate group or a heterocyclic group13、R14And R15The methylene group in the hydrocarbon group having 2 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be-O-, -CO-, -COO-, -OCO-, -NR16-、-NR16CO-、-S-、-SO2-, -SCO-or-COS-substitution,
R16represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
R11and R12Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R11and R12The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be substituted with 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 ether group, a mercapto group, an isocyanate group or a heterocyclic group, and R is 11And R12The methylene group in the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be-O-, -CO-, -COO-, -OCO-, -NR17-、-NR17CO-、-S-、-SO2-, -SCO-or-COS-substitution,
R17represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
R1～R10at least one of which is a group represented by the following general formula (II),
R2and R3、R3And R4、R4And R5、R6And R7、R7And R8、R8And R9And R9And R10Sometimes they are bonded to form a ring,
m represents 0 or 1.
[ CHEM 29 ]
(in the formula, R21And R22Each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,
R21and R22The hydrogen atom of the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be substituted with 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 ether group, a mercapto group, an isocyanate group or a heterocyclic group, and R is21And R22The methylene group in the hydrocarbon group having 1 to 20 carbon atoms or the heterocyclic group having 2 to 20 carbon atoms may be-O-, -CO-, -COO-, -OCO-, -NR23-、-NR23CO-、-S-、-SO2-, -SCO-or-COS-substituted, R23Represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms,
n represents 0 or 1. ))
Among the above photopolymerization initiators, a photopolymerization initiator having a high molecular weight is preferable, specifically, a photopolymerization initiator having a molecular weight of 400 or more is preferable, and a photopolymerization initiator having a molecular weight of 500 or more is particularly preferable, from the viewpoint of preventing the occurrence of outgas by preventing the outgas even if the photopolymerization initiator is cleaved, and reliably suppressing the occurrence of outgas. The upper limit of the molecular weight of the photopolymerization initiator is not particularly limited, and examples thereof include 10000 or less.
The amount of the photopolymerization initiator to be blended is not particularly limited, and may be appropriately selected, and is, for example, preferably 0.1 to 10% by mass, and particularly preferably 1 to 5% by mass, based on 100% by mass of the adhesive.
As required, various additives such as a plasticizer, a pigment, a dye, an antioxidant, an antistatic agent, and a filler added to improve the physical properties of the adhesive layer such as the elastic modulus may be added to the adhesive as optional components.
The thickness of the radiation-curable adhesive layer is not particularly limited, but is preferably 1 to 50 μm, and particularly preferably 5 to 25 μm. When the thickness of the radiation curable adhesive layer is less than 1 μm, the followability to an adherend is impaired, and the adhesive force in the dicing after the reflow step may be reduced. On the other hand, when the thickness of the radiation-curable adhesive layer exceeds 50 μm, the adhesive itself is broken, and adhesive residue may be generated in which a defective adhesive is attached to an adherend.
The type of radiation is appropriately set according to the type of adhesive included in the radiation-curable adhesive layer. Examples of the radiation include ultraviolet rays and electron beams. The reflow of the present invention is particularly preferably applied to the sliced ribbon, and the ultraviolet rays among these radiation rays are particularly preferable. That is, as the radiation curable adhesive layer, an ultraviolet curable adhesive layer is particularly preferable; as the adhesive, an ultraviolet-curable adhesive is particularly preferable.
The method of generating ultraviolet rays is not particularly limited, and conventionally known methods of generating ultraviolet rays can be suitably employed. Specific examples of the ultraviolet ray generation system include a discharge lamp system (arc lamp), a flash system, and a laser system. Among these, the discharge lamp system is preferred from the viewpoint of industrial production, and among the discharge lamp systems, the irradiation method using a high-pressure mercury lamp or a metal halide lamp is particularly preferred from the viewpoint of irradiation efficiency of ultraviolet rays.
The wavelength of the ultraviolet light is not particularly limited, and is preferably within a range of 250nm to 400nm in terms of the wavelength used for general photocuring and the wavelength of the ultraviolet light generating source used in the irradiation method.
The irradiation amount of ultraviolet rays is not particularly limited as long as the effect of the photopolymerization initiator can be produced by ultraviolet rays. Specifically, for example, it is preferably 10 to 3000mJ/cm2Particularly preferably 50 to 2000mJ/cm2. The ultraviolet irradiation amount is less than 10mJ/cm2In the case of (3), the adhesive may not be sufficiently cured. Further, the dose of ultraviolet irradiation exceeds 3000mJ/cm2In the case of (a) in (b),the photocuring of the adhesive proceeds excessively, and the radiation-curable adhesive layer may be broken.
Examples of the adherend for reflow-supporting dicing tape of the present invention include a silicon wafer.
Examples
The following describes examples of the present invention, but unless otherwise specified, the materials, amounts of mixing, and the like described in the examples are not intended to limit the scope of the present invention, and are merely illustrative examples.
Example 1
As the photopolymerization initiator, α -hydroxyacetophenone (Irugacure 184, manufactured by BASF) was used. An acrylic copolymer (Mw 70 ten thousand) synthesized by blending 5 parts by mass of a (meth) acrylic acid monomer with 100 parts by mass of a butyl (meth) acrylate monomer, α -hydroxyacetophenone: mass ratio of acrylic copolymer 5: 100 to prepare the radiation curing adhesive. The adhesive was applied to a 50 μm PEEK film, and the solvent in the adhesive was evaporated at 120 ℃ to form a radiation-curable adhesive layer (thickness 20 μm) to produce a reflow-compatible dicing tape.
Example 2
As the photopolymerization initiator, an oxime ester compound is used. As the oxime ester compound, the following compound (molecular weight 355) was used.
[ CHEM 30 ]
The oxime ester compound used in example 2 was prepared as follows.
To a solution of 92g of dichloroethane and 21.7g (163mmol) of aluminum chloride was added 20.73g (6.5mmol) of the following alcohol, followed by dropwise addition of 9.0g (97mmol) of propionyl chloride at 6 ℃ or lower. After stirring for 1 hour, the reaction mixture was poured into ice water, ethyl acetate was added to separate the oil and water, and the organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then desolvation was performed to obtain 17.5g of an acyl body a.
[ CHEM 31 ]
Oximation of
To a solution of 13.0g (35mmol) of the obtained acyl compound a, 3.6g (35mmol) of concentrated hydrochloric acid and 30g of dimethylformamide was added 5.4g (52mmol) of isobutyl nitrite, and the mixture was stirred at room temperature for 3.5 hours. After stirring, ethyl acetate and water were added to the reaction solution to conduct oil-water separation, and the organic layer was washed with water. Hexane was added to the organic layer from which the solid was precipitated, followed by filtration. The resulting solid was dried under reduced pressure to obtain 7.8g of oxime a.
[ CHEM 32 ]
Esterification of oximes
A solution of 5.0g (13mmol) of the obtained oxime a, 2.1g (27mmol) of pyridine and 12g of dimethylformamide was allowed to stand at-10 ℃ or lower, and 1.6g (15mmol) of acetic anhydride was added dropwise thereto, followed by stirring at 5 ℃ for 2 hours. After stirring, ethyl acetate and water were added to the reaction solution to conduct oil-water separation, and the organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was removed, whereby 3.5g of the oxime ester compound was obtained.
An acrylic copolymer (Mw 70 ten thousand) synthesized by mixing the oxime ester compound obtained as described above with 5 parts by mass of a (meth) acrylic acid monomer per 100 parts by mass of a butyl (meth) acrylate monomer was synthesized in accordance with the oxime ester compound: mass ratio of acrylic copolymer 5: 100 to prepare the radiation curing adhesive. The adhesive was applied to a 50 μm PEEK film, and the solvent in the adhesive was evaporated at 120 ℃ to form a radiation-curable adhesive layer (thickness 20 μm) to produce a reflow-compatible dicing tape.
Example 3
A reflow-compatible sliced tape was produced in the same manner as in example 2 except that the oxime ester compound of example 2, which was compounded as a photopolymerization initiator, was changed to the oxime ester compound (molecular weight 445, irugature OXE01, BASF) described below.
[ CHEM 33 ]
Example 4
A reflow-compatible sliced crystal tape was produced in the same manner as in example 2 except that the oxime ester compound of example 2, which was compounded as a photopolymerization initiator, was changed to the oxime ester compound (molecular weight 515) described below. In addition, with respect to the oxime ester compound of example 4, 10.4g (78 mmol) of aluminum chloride and 33.0g of dichloroethane were charged under a nitrogen atmosphere, 36 mmol of acid chloride was slowly dropped under ice cooling, 30 mmol of the nitrocarbazole compound and 33.0g of dichloroethane were slowly dropped, and stirring was carried out at 5 ℃ for 30 minutes. Pouring the reaction solution into ice water for oil-water separation. Desolventizing to obtain the acyl matrix. Under a nitrogen stream, 20 mmol of the obtained acyl compound, 2.1g (30 mmol) of hydroxylamine hydrochloride and 16.9g of dimethylformamide were put, and the mixture was stirred at 80 ℃ for 1 hour. Cooling to room temperature, and performing oil-water separation. The solvent was distilled off, and 25.4g of butyl acetate and then 2.45g (24 mmol) of acetic anhydride were added to the residue, and the mixture was stirred at 90 ℃ for 1 hour and cooled to room temperature. The resulting product was neutralized with a 5% aqueous solution of sodium hydroxide, subjected to oil-water separation, desolventization, and recrystallization from ethyl acetate to obtain the following oxime ester compound as a target substance.
[ CHEM 34 ]
Comparative example 1
The blending amount of α -hydroxyacetophenone of example 1 blended as a photopolymerization initiator was made to be α -hydroxyacetophenone: mass ratio of acrylic copolymer 10: 100, a sliced crystal ribbon was produced in the same manner as in example 1 except that.
(1) Carbon content by X-ray photoelectron spectroscopy (XPS)
Bonding the prepared reflow corresponding sliced crystal belt to a silicon wafer at 1000mJ/cm2After irradiation with ultraviolet rays (wavelength: 365nm), heat treatment was carried out at 210 ℃ for 10 minutes. Next, after the reflow-corresponding dicing tape was peeled off from the silicon wafer, the amount of carbon in the total amount of the components attached to the surface of the silicon wafer to which the reflow-corresponding dicing tape was attached was measured by X-ray photoelectron spectroscopy (XPS) and evaluated as follows. The XPS device used PHI Quantes (manufactured by ULVAC-PHI corporation), the excitation X-ray was a monochromatized Al-Ka ray, the emission angle was 45 degrees, and the measurement was performed in a wide scanning range of 1350 to 0 eV. The analysis area is
O: carbon content of 30 mol% or less
X: the carbon content is more than 30 mol%
(2) Reduced outgassing
The presence or absence of outgas generated during the heat treatment at 210 ℃ for 10 minutes was evaluated by observing bubbles generated in the radiation-curable adhesive layer after the heat treatment visually or with an optical microscope.
O: hardly generates bubbles
And (delta): with some bubbles
X: obviously has bubbles
(3) Prevent chip dispersion
The number of chips peeled from the dicing tape was measured in the dicing step of dividing the silicon wafer into individual pieces after the heat treatment at 210 ℃ for 10 minutes, and the evaluation was performed.
Very good: chip without peeling from dicing tape
O: there are chips peeled from the dicing tape, but the proportion is 1% or less
And (delta): the proportion of chips peeled from the dicing tape is more than 1% and 5% or less
X: the proportion of chips peeled from the dicing tape exceeded 5%
The evaluation results are shown in Table 1.
[ TABLE 1 ]
| Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | |
| Carbon content by X-ray photoelectron spectroscopy | ○ | ○ | ○ | ○ | × |
| Reduced outgassing | △ | ○ | ○ | ○ | × |
| Prevent chip dispersion | △ | △ | ○ | ◎ | × |
As is clear from table 1, in examples 1 to 4 in which the amount of carbon was 30 mol% or less as measured by X-ray photoelectron spectroscopy, outgassing reduction was obtained, and the proportion of chips peeled from the dicing tape could be reduced to 5% or less. In particular, as is clear from comparison between example 1 and examples 2 to 4, if an oxime ester compound is used as a photopolymerization initiator, outgassing can be further reduced. Further, as is clear from comparison of example 2 with examples 3 and 4, when the molecular weight is 400 or more and the molecular weight of the oxime ester compound as a photopolymerization initiator is large, the proportion of chips peeled from the sliced ribbon can be further reduced.
On the other hand, in comparative example 1 in which the amount of carbon measured by X-ray photoelectron spectroscopy exceeded 30 mol%, the outgassing reduction was not obtained, and the proportion of chips peeled from the sliced ribbon exceeded 5%.
Claims (7)
1. A reflow die-cutting tape comprises a substrate layer and a radiation-curable adhesive layer disposed on the substrate layer,
and a step of bonding a silicon wafer to the radiation-curable adhesive layer, irradiating the silicon wafer with a radiation, and then performing a heat treatment at 210 ℃ for 10 minutes, wherein the silicon wafer is peeled from the radiation-curable adhesive layer after the heat treatment, and wherein the amount of carbon in the bonded surface of the silicon wafer is 30 mol% or less as measured by an X-ray photoelectron spectroscopy.
2. The reflow die attach tape of claim 1 wherein the radiation curable adhesive layer comprises: a polymerizable compound having an ethylenically unsaturated bond, 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 an anion, and a photopolymerization initiator.
3. The reflow-compatible dicing tape according to claim 2, wherein the polymer of the polymerizable compound having an ethylenically unsaturated bond comprises a (meth) acrylic polymer which is a polymer of a monomer containing (meth) acrylic acid and/or a (meth) acrylate.
4. The reflow-aligned sliced ribbon according to claim 2 or 3, wherein the photopolymerization initiator is an oxime ester compound.
5. The reflow-compatible dicing tape according to any one of claims 2 to 4, wherein the photopolymerization initiator has a molecular weight of 400 or more.
6. The reflow die-cut tape according to any one of claims 1 to 5, wherein the radiation-curable adhesive layer is an ultraviolet-curable adhesive layer.
7. The reflow-corresponding sliced ribbon of any one of claims 1 to 6, wherein the thickness is 1000mJ/cm2The radiation curable adhesive layer is irradiated with a radiation ray having a wavelength of 350nm, and then subjected to a heat treatment at 210 ℃ for 10 minutes, and then the adhesive force measured according to JIS Z0237 is 0.3N/25mm width or more and 2.0N/25mm width or less.
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| PCT/JP2019/047232 WO2020116448A1 (en) | 2018-12-04 | 2019-12-03 | Reflow-compatible dicing tape |
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