KR20230172230A - Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive - Google Patents
Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive Download PDFInfo
- Publication number
- KR20230172230A KR20230172230A KR1020220072817A KR20220072817A KR20230172230A KR 20230172230 A KR20230172230 A KR 20230172230A KR 1020220072817 A KR1020220072817 A KR 1020220072817A KR 20220072817 A KR20220072817 A KR 20220072817A KR 20230172230 A KR20230172230 A KR 20230172230A
- Authority
- KR
- South Korea
- Prior art keywords
- adhesive
- meth
- acrylate
- composition
- monomer
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 179
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 179
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 239000002313 adhesive film Substances 0.000 title claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 90
- 239000000178 monomer Substances 0.000 claims description 73
- -1 isocyanate compounds Chemical class 0.000 claims description 48
- 239000012948 isocyanate Substances 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 239000012790 adhesive layer Substances 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 229920006243 acrylic copolymer Polymers 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 claims description 3
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004816 latex Substances 0.000 claims 1
- 229920000126 latex Polymers 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 16
- 230000007423 decrease Effects 0.000 abstract description 15
- 230000008569 process Effects 0.000 abstract description 11
- 239000004065 semiconductor Substances 0.000 abstract description 10
- 230000035939 shock Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000003848 UV Light-Curing Methods 0.000 description 23
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 23
- 230000008859 change Effects 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012858 packaging process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical group C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- GKZPEYIPJQHPNC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GKZPEYIPJQHPNC-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 229940024874 benzophenone Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 208000028659 discharge Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 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
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- 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
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
- C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
본 발명은 광감응성 점착제 제조용 조성물, 이를 이용하여 제조된 광감응성 점착제 및 상기 점착제를 포함하는 점착필름에 관한 것이다.
본 발명을 이용하면 자외선 조사 전 강한 점착력을 유지할 수 있으면서, 자외선 조사 후에는 점착력이 크게 저하되는 점착제를 제조할 수 있다. 따라서, 본 발명을 다이싱용 점착필름에 적용하면 반도체의 다이싱 공정에서 가해지는 충격 및 수압에 의한 칩의 비산을 효과적으로 방지할 수 있고, 자외선 조사 후에는 점착력이 매우 낮아져 박리 후 칩에 잔사가 남지 않으며 칩을 용이하게 픽업할 수 있다. The present invention relates to a composition for producing a photosensitive adhesive, a photosensitive adhesive manufactured using the same, and an adhesive film containing the adhesive.
Using the present invention, it is possible to produce an adhesive that can maintain strong adhesive strength before irradiation with ultraviolet rays, but whose adhesive strength significantly decreases after irradiation with ultraviolet rays. Therefore, applying the present invention to an adhesive film for dicing can effectively prevent chips from scattering due to shock and water pressure applied during the dicing process of semiconductors, and after irradiation with ultraviolet rays, the adhesive strength becomes very low, leaving no residue on the chip after peeling. And chips can be easily picked up.
Description
본 발명은 광감응성 점착제 제조용 조성물, 이를 이용하여 제조된 광감응성 점착제 및 상기 점착제를 포함하는 점착필름에 관한 것으로서, 더욱 상세하게는 자외선 조사 전 강한 점착력을 유지하고 자외선 조사 후에는 매우 낮은 점착력을 나타내는 광감응성 점착제 제조용 조성물, 이를 이용하여 제조된 광감응성 점착제 및 상기 점착제를 포함하는 점착필름에 관한 것이다.The present invention relates to a composition for producing a photosensitive adhesive, a photosensitive adhesive manufactured using the same, and an adhesive film containing the adhesive. More specifically, it relates to a composition that maintains strong adhesiveness before irradiation with ultraviolet rays and exhibits very low adhesiveness after irradiation with ultraviolet rays. It relates to a composition for producing a photosensitive adhesive, a photosensitive adhesive manufactured using the same, and an adhesive film containing the adhesive.
반도체 후공정인 패키징(packaging) 공정은 웨이퍼(wafer)를 개별 반도체 칩(chip)으로 나누고 칩을 기판에 본딩하는 공정이다. 구체적으로, 먼저 다이싱용 점착제를 포함하는 점착제층 및 다이본딩용 접착제를 포함하는 접착제층을 포함하는 필름 상에 웨이퍼를 부착한 상태에서 웨이퍼를 개별 칩으로 나누는 다이싱(dicing) 작업을 수행한다. 그 후, 점착제층의 점착력을 감소시켜 점착제층이 칩에 부착된 접착제층과 박리되도록 한 다음, 지지부재 상에 접착제층을 통해 칩을 부착하는 다이본딩(die bonding) 공정을 수행한다. The packaging process, a semiconductor post-process, is a process of dividing a wafer into individual semiconductor chips and bonding the chips to a substrate. Specifically, first, a dicing operation is performed to divide the wafer into individual chips while the wafer is attached to a film including an adhesive layer containing a dicing adhesive and an adhesive layer containing a die-bonding adhesive. Afterwards, the adhesive force of the adhesive layer is reduced to cause the adhesive layer to peel off from the adhesive layer attached to the chip, and then a die bonding process is performed to attach the chip to the support member through the adhesive layer.
상기 다이싱용 점착제층은 자외선 조사에 의해 점착력이 감소되는 자외선 경화성 점착제를 이용하여 제조된다. 상기 자외선 경화성 점착제는 일반적으로 베이스 수지에 광개시제가 첨가된 것으로, 자외선 조사 전에는 다이싱 공정에서 웨이퍼가 박리되지 않도록 하기 위하여 강한 점착력을 유지해야 하고, 자외선 조사 후에는 칩의 픽업(pick up)을 위해 점착력이 크게 감소되는 특성이 요구된다.The adhesive layer for dicing is manufactured using an ultraviolet curable adhesive whose adhesive strength is reduced by ultraviolet irradiation. The UV-curable adhesive is generally one in which a photoinitiator is added to the base resin, and must maintain strong adhesive strength to prevent the wafer from peeling off during the dicing process before UV irradiation, and to pick up chips after UV irradiation. A characteristic in which adhesion is greatly reduced is required.
관련하여, 일본 등록특허공보 제3483161호에서는 공정의 간략화를 위해 점접착제를 이용하여 점착제층과 접착제층이 일체형으로 구성된 점접착 테이프를 개시하고 있다. 그러나, 상기 일체형 점접착 테이프의 경우 자외선 조사 시 점착제와 접착제의 반응과 자외선의 영향에 의해 픽업성이 떨어질 수 있고, 접착제가 일부 경화되어 다이본딩 시 칩의 접착력이 저하되는 문제가 발생할 수 있다.In relation to this, Japanese Patent Publication No. 3483161 discloses an adhesive tape in which an adhesive layer and an adhesive layer are integrated using an adhesive to simplify the process. However, in the case of the integrated adhesive tape, pick-up performance may be reduced due to the reaction between the adhesive and the adhesive and the influence of ultraviolet rays when irradiated with ultraviolet rays, and the adhesive may partially harden, which may cause a problem in that the adhesive strength of the chip is reduced during die bonding.
또한, 일본 등록특허공보 제4931519호에서는 방사선 경화성 점착제층이 히드록시기를 포함하는 화합물을 포함하여 픽업성이 우수한 점착필름을 개시하고 있다. 그러나, 히드록시기를 포함하는 화합물은 점착 반응에 관여하지 않는 저분자 화합물로서, 표면에 존재하는 히드록시기를 포함하는 화합물로 인해 웨이퍼와 점착필름 간의 점착성이 저하된다는 문제가 있었다.Additionally, Japanese Patent Registration No. 4931519 discloses an adhesive film with excellent pick-up properties in which the radiation-curable adhesive layer contains a compound containing a hydroxy group. However, the compound containing a hydroxy group is a low molecular weight compound that does not participate in the adhesion reaction, and there was a problem that the adhesion between the wafer and the adhesive film was reduced due to the compound containing a hydroxy group present on the surface.
이러한 상황에서, 다이싱 공정에서 강한 점착력을 유지하여 칩의 비산을 방지할 수 있는 특성 및 자외선 조사 후에는 점착력이 크게 저하되어 픽업이 용이하도록 하는 특성을 모두 갖는 점착제의 개발이 필요하다.In this situation, there is a need to develop an adhesive that has both the property of maintaining strong adhesive force during the dicing process to prevent chips from scattering, and the property that the adhesive force is greatly reduced after ultraviolet irradiation to facilitate pick-up.
본 발명의 목적은 자외선 조사 전에는 점착력이 우수하고 자외선 조사 후에는 점착력이 크게 저하되는 광감응성 점착제 제조용 조성물을 제공하는 것이다.The purpose of the present invention is to provide a composition for manufacturing a photosensitive adhesive, which has excellent adhesive strength before UV irradiation and greatly reduces adhesive strength after UV irradiation.
본 발명의 다른 목적은 상기 점착제 제조용 조성물을 이용하여 제조된 점착제를 제공하는 것이다.Another object of the present invention is to provide an adhesive manufactured using the composition for producing the adhesive.
본 발명의 또 다른 목적은 상기 점착제를 포함하는 점착필름을 제공하는 것이다.Another object of the present invention is to provide an adhesive film containing the adhesive.
상기 목적을 달성하기 위해, 본 발명은 히드록시기를 갖는 아크릴계 공중합체 및 탄소-탄소 이중결합을 갖는 이소시아네이트(isocyanate) 화합물을 포함하는 광감응성 점착제 제조용 조성물을 제공한다.To achieve the above object, the present invention provides a composition for producing a photosensitive adhesive containing an acrylic copolymer having a hydroxy group and an isocyanate compound having a carbon-carbon double bond.
본 발명에서, 상기 아크릴계 공중합체는 알킬기를 갖는 (메타)아크릴레이트계 단량체, 히드록시기를 갖는 (메타)아크릴레이트계 단량체 및 불포화 카르복실산 단량체를 포함하는 단량체 조성물을 중합시켜 제조될 수 있다.In the present invention, the acrylic copolymer may be produced by polymerizing a monomer composition containing a (meth)acrylate monomer having an alkyl group, a (meth)acrylate monomer having a hydroxy group, and an unsaturated carboxylic acid monomer.
본 발명에서, 상기 이소시아네이트 화합물은 상기 아크릴계 공중합체 100중량부에 대하여 0.5 내지 15중량부 포함될 수 있다.In the present invention, the isocyanate compound may be included in an amount of 0.5 to 15 parts by weight based on 100 parts by weight of the acrylic copolymer.
본 발명에서, 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시부틸(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 8-히드록시옥틸(메타)아크릴레이트, 1,4-시클로헥산디메탄올모노(메타)아크릴레이트, 클로로-2-히드록시프로필아크릴레이트, 디에틸렌글리콜모노(메타)아크릴레이트 및 프로필렌글리콜(메타)아크릴레이트로 구성된 군에서 선택된 1종 이상을 포함할 수 있다.In the present invention, the (meth)acrylate monomer having the hydroxy group is 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4- Hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 1,4-cyclohexanedimethanol mono (meth)acrylate, chloro-2- It may include one or more selected from the group consisting of hydroxypropyl acrylate, diethylene glycol mono(meth)acrylate, and propylene glycol (meth)acrylate.
본 발명에서, 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체는 상기 단량체 조성물 전체 중량에 대하여 3 내지 30중량% 포함될 수 있다.In the present invention, the (meth)acrylate monomer having the hydroxy group may be included in an amount of 3 to 30% by weight based on the total weight of the monomer composition.
본 발명에서, 상기 단량체 조성물은 시클로알킬기를 갖는 (메타)아크릴레이트 단량체 또는 방향족 (메타)아크릴레이트 단량체를 더 포함할 수 있다.In the present invention, the monomer composition may further include a (meth)acrylate monomer or an aromatic (meth)acrylate monomer having a cycloalkyl group.
본 발명에서, 상기 이소시아네이트 화합물은 (메타)아크릴로일옥시 이소시아네이트, (메타)아크릴로일옥시메틸 이소시아네이트, (메타)아크릴로일옥시에틸 이소시아네이트, (메타)아크릴로일옥시프로필 이소시아네이트 및 (메타)아크릴로일 이소시아네이트로 구성된 군에서 선택된 1종 이상을 포함할 수 있다.In the present invention, the isocyanate compound includes (meth)acryloyloxy isocyanate, (meth)acryloyloxymethyl isocyanate, (meth)acryloyloxyethyl isocyanate, (meth)acryloyloxypropyl isocyanate, and (meth)acryloyloxypropyl isocyanate. It may include one or more types selected from the group consisting of acryloyl isocyanate.
본 발명에서, 상기 이소시아네이트 화합물은 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대해 20 내지 80중량부 포함될 수 있다.In the present invention, the isocyanate compound may be included in an amount of 20 to 80 parts by weight based on 100 parts by weight of the (meth)acrylate monomer having the hydroxy group.
본 발명은 또한, 상기 광감응성 점착제 제조용 조성물을 이용하여 제조된 광감응성 점착제를 제공한다.The present invention also provides a photosensitive adhesive manufactured using the composition for producing the photosensitive adhesive.
본 발명에서, 상기 광감응성 점착제는 상기 광감응성 점착제 제조용 조성물을 반응시켜 제조된 바인더 수지, 및 광개시제를 포함할 수 있다.In the present invention, the photosensitive adhesive may include a binder resin prepared by reacting the composition for producing the photosensitive adhesive, and a photoinitiator.
본 발명에서, 상기 점착제는 2 내지 12관능의 (메타)아크릴레이트 화합물을 1종 이상 포함하는 UV 경화성 올리고머를 더 포함할 수 있다.In the present invention, the adhesive may further include a UV curable oligomer containing one or more types of 2 to 12 functional (meth)acrylate compounds.
본 발명에서, 상기 광개시제는 바인더 수지 100중량부에 대하여 0.1 내지 10중량부 포함될 수 있다.In the present invention, the photoinitiator may be included in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the binder resin.
본 발명은 또한, 상기 점착제를 이용한 점착필름을 제공한다.The present invention also provides an adhesive film using the adhesive.
본 발명에서, 상기 점착필름은 기재, 및 상기 기재 상에 형성되며 상기 광감응성 점착제를 포함하는 점착제층을 포함할 수 있다.In the present invention, the adhesive film may include a substrate and an adhesive layer formed on the substrate and containing the photosensitive adhesive.
본 발명을 이용하면 자외선 조사 전 강한 점착력을 유지할 수 있으면서, 자외선 조사 후에는 점착력이 크게 저하되는 점착제를 제조할 수 있다. 따라서, 본 발명을 다이싱용 점착필름에 적용하면 반도체의 다이싱 공정에서 가해지는 충격 및 수압에 의한 칩의 비산을 효과적으로 방지할 수 있고, 자외선 조사 후에는 점착력이 매우 낮아져 박리 후 칩에 잔사가 남지 않으며 칩을 용이하게 픽업할 수 있다. Using the present invention, it is possible to produce an adhesive that can maintain strong adhesive strength before irradiation with ultraviolet rays, but whose adhesive strength significantly decreases after irradiation with ultraviolet rays. Therefore, applying the present invention to an adhesive film for dicing can effectively prevent chips from scattering due to shock and water pressure applied during the dicing process of semiconductors, and after irradiation with ultraviolet rays, the adhesive strength becomes very low, leaving no residue on the chip after peeling. And chips can be easily picked up.
도 1은 자가 가교형 점착제의 베이스 구조를 개략적으로 나타낸 것이다.
도 2는 자외선 조사에 의한 점착제의 구조 변화를 예시적으로 나타낸 것이다.
도 3은 본 발명의 일 실시예에 따른 점착제의 UV 조사 전후 박리력 측정 결과를 나타낸 것이다.
도 4는 본 발명의 일 실시예에 따른 점착제의 UV 조사 전후 박리력 변화를 그래프로 나타낸 것이다.
도 5는 본 발명의 다른 실시예에 따른 점착제의 UV 조사 전후 박리력 측정 결과를 나타낸 것이다.
도 6은 본 발명의 다른 실시예에 따른 점착제의 UV 조사 전후 박리력 변화를 그래프로 나타낸 것이다.
도 7은 본 발명의 또 다른 실시예에 따른 점착제의 UV 조사 전후 박리력 측정 결과를 나타낸 것이다.
도 8은 본 발명의 또 다른 실시예에 따른 점착제의 UV 조사 전후 박리력 변화를 그래프로 나타낸 것이다.Figure 1 schematically shows the base structure of a self-crosslinking adhesive.
Figure 2 exemplarily shows the structural change of the adhesive due to ultraviolet irradiation.
Figure 3 shows the results of measuring the peeling force of an adhesive before and after UV irradiation according to an embodiment of the present invention.
Figure 4 graphically shows the change in peel strength of the adhesive according to an embodiment of the present invention before and after UV irradiation.
Figure 5 shows the results of measuring the peeling force of an adhesive according to another embodiment of the present invention before and after UV irradiation.
Figure 6 graphically shows the change in peel strength of an adhesive according to another embodiment of the present invention before and after UV irradiation.
Figure 7 shows the results of measuring the peeling force of an adhesive before and after UV irradiation according to another embodiment of the present invention.
Figure 8 is a graph showing the change in peel strength of an adhesive according to another embodiment of the present invention before and after UV irradiation.
이하, 본 발명의 구체적인 구현 형태에 대해서 보다 상세히 설명한다. 다른 식으로 정의되지 않는 한, 본 명세서에서 사용된 모든 기술적 및 과학적 용어들은 본 발명이 속하는 기술 분야에서 숙련된 전문가에 의해서 통상적으로 이해되는 것과 동일한 의미를 갖는다. 일반적으로, 본 명세서에서 사용된 명명법은 본 기술 분야에서 잘 알려져 있고 통상적으로 사용되는 것이다.Hereinafter, specific implementation forms of the present invention will be described in more detail. Unless otherwise defined, all technical and scientific terms used in this specification have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. In general, the nomenclature used herein is well known and commonly used in the art.
본 발명은 자가 가교형 광감응성 점착제 제조용 조성물, 이를 이용하여 제조된 점착제, 및 상기 점착제를 포함하는 점착필름에 관한 것이다. The present invention relates to a composition for producing a self-crosslinking photosensitive adhesive, an adhesive manufactured using the same, and an adhesive film containing the adhesive.
일반적인 점착제는 자외선 조사(UV)에 의한 경화 반응에 직접 참여할 수 없으며, 블렌딩된 올리고머(oligomer)의 반응에 따라 특성이 변화하고 반응 후 잔사 등에도 영향을 미친다. 즉, UV 경화 반응은 올리고머의 결합을 유도하는 것으로, 점착제의 기본 구조가 되는 중합체, 즉 점착제 베이스의 결합을 유도하는 것은 아니기 때문에 베이스의 안정성에는 영향을 미치지 않게 된다. 또한, 베이스가 직접적으로 반응에 참여하지 않으므로 UV 경화 전후 점착력의 변화에도 한계가 있다.General adhesives cannot directly participate in the curing reaction by ultraviolet irradiation (UV), and their properties change depending on the reaction of the blended oligomer and also affect residues after the reaction. In other words, the UV curing reaction induces the bonding of oligomers and does not induce the bonding of the polymer, which is the basic structure of the adhesive, that is, the adhesive base, so it does not affect the stability of the base. Additionally, since the base does not directly participate in the reaction, there are limits to the change in adhesion before and after UV curing.
본 발명에서는 점착제의 베이스가 직접 UV 경화 반응에 참여할 수 있는 자가 가교형(self-crosslinking) 구조를 이용한다. 본 발명에 따르면, 점착제의 베이스가 UV 경화 반응에 직접 참여하도록 하기 위해 곁사슬에 반응기를 유도하여 도 1과 같이 반응기가 내외부로 뻗어 있는 구조를 형성할 수 있다. The present invention uses a self-crosslinking structure in which the base of the adhesive can directly participate in the UV curing reaction. According to the present invention, in order for the base of the adhesive to directly participate in the UV curing reaction, a reactive group can be induced in the side chain to form a structure in which the reactive group extends inside and out as shown in FIG. 1.
도 2는 자외선 조사에 의한 본 발명의 점착제의 구조 변화를 예시적으로 나타낸 것이다. 본 발명의 점착제는 자외선 경화에 의해 가교 결합 외에도 베이스 간 결합을 효과적으로 형성할 수 있으므로, 자외선 조사 후 점착력이 크게 저하될 수 있다.Figure 2 exemplarily shows the structural change of the adhesive of the present invention due to ultraviolet irradiation. Since the adhesive of the present invention can effectively form base-to-base bonds in addition to crosslinking through ultraviolet curing, the adhesive strength may be significantly reduced after irradiation with ultraviolet rays.
본 발명에서는 점착제의 기본 구조로서 히드록시기(hydroxyl group, -OH)를 갖는 공중합체 및 이소시아네이트(isocyanate, -NCO) 화합물을 이용하고, 특히 공중합체에 포함되는 단량체와 이소시아네이트 화합물의 종류 및 함량을 최적화함으로써 자외선 조사 전후 점착력을 효과적으로 조절할 수 있는 자가 가교형 점착제를 설계하였다.In the present invention, a copolymer having a hydroxyl group (-OH) and an isocyanate (-NCO) compound are used as the basic structure of the adhesive, and in particular, by optimizing the type and content of the monomer and isocyanate compound contained in the copolymer. We designed a self-crosslinking adhesive that can effectively control adhesive strength before and after ultraviolet irradiation.
본 발명의 광감응성 점착제 제조용 조성물은 히드록시기(hydroxyl group)를 갖는 아크릴계 공중합체 및 탄소-탄소 이중결합을 갖는 이소시아네이트(isocyanate) 화합물을 포함할 수 있다. The composition for producing a photosensitive adhesive of the present invention may include an acrylic copolymer having a hydroxyl group and an isocyanate compound having a carbon-carbon double bond.
본 발명에서 사용되는 아크릴계 공중합체는 바인더 수지의 골격을 형성하는 것으로서 분자 내 하나 이상의 히드록시기를 포함하고, 상기 히드록시기가 이소시아네이트와 효과적으로 반응하여 가교 구조를 형성하게 된다.The acrylic copolymer used in the present invention forms the skeleton of the binder resin and contains one or more hydroxy groups in the molecule, and the hydroxy groups effectively react with isocyanate to form a cross-linked structure.
본 발명에서, 상기 아크릴계 공중합체는 알킬기를 갖는 (메타)아크릴레이트계 단량체 및 히드록시기를 갖는 (메타)아크릴레이트계 단량체를 포함하는 단량체 조성물을 중합시켜 제조된 것일 수 있다. 본 발명을 설명함에 있어서, 용어 "(메타)아크릴레이트"는 아크릴레이트 또는 메타크릴레이트를 의미하고, 용어 "알킬기"는 직쇄형 또는 분지형 알킬기를 의미하는 것으로 해석된다.In the present invention, the acrylic copolymer may be manufactured by polymerizing a monomer composition containing a (meth)acrylate-based monomer having an alkyl group and a (meth)acrylate-based monomer having a hydroxy group. In describing the present invention, the term "(meth)acrylate" is interpreted to mean acrylate or methacrylate, and the term "alkyl group" is interpreted to mean a straight-chain or branched alkyl group.
구체적으로, 본 발명에서 사용되는 아크릴계 공중합체는 탄소수 1 내지 20의 알킬기를 갖는 (메타)아크릴레이트 단량체, 히드록시기를 갖는 (메타)아크릴레이트 단량체 및 불포화 카르복실산 단량체를 포함하는 단량체 조성물을 중합 반응시켜 제조된 것일 수 있다. Specifically, the acrylic copolymer used in the present invention is a polymerization reaction of a monomer composition containing a (meth)acrylate monomer having an alkyl group having 1 to 20 carbon atoms, a (meth)acrylate monomer having a hydroxy group, and an unsaturated carboxylic acid monomer. It may have been manufactured.
본 발명에서, 상기 탄소수 1 내지 20의 알킬기를 갖는 (메타)아크릴레이트 단량체는, 예를 들어 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, n-프로필(메타)아크릴레이트, 이소프로필(메타)아크릴레이트, n-부틸(메타)아크릴레이트, t-부틸(메타)아크릴레이트, 펜틸(메타)아크릴레이트, n-옥틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 이소노닐(메타)아크릴레이트 등을 1종 이상 포함할 수 있다. 상기 (메타)아크릴레이트 단량체에 포함되는 알킬기의 탄소수가 너무 많으면 점착제의 응집력이 저하될 수 있으므로 탄소수 1 내지 12의 알킬기를 갖는 것이 바람직하게 사용될 수 있으며, 특히 2-에틸헥실(메타)아크릴레이트를 이용함으로써 초기 점착력을 향상시킬 수 있다.In the present invention, the (meth)acrylate monomer having an alkyl group having 1 to 20 carbon atoms is, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl ( meta)acrylate, n-butyl(meth)acrylate, t-butyl(meth)acrylate, pentyl(meth)acrylate, n-octyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, iso It may contain one or more types of nonyl (meth)acrylate, etc. If the alkyl group included in the (meth)acrylate monomer has too many carbon atoms, the cohesion of the adhesive may decrease, so an alkyl group having 1 to 12 carbon atoms can be preferably used, especially 2-ethylhexyl (meth)acrylate. By using it, the initial adhesion can be improved.
상기 알킬기를 갖는 (메타)아크릴레이트 단량체는, 단량체 조성물 전체 중량에 대하여 55 내지 95중량%, 바람직하게는 60 내지 80중량% 포함될 수 있다. 상기 알킬기를 갖는 (메타)아크릴레이트 단량체의 함량이 너무 낮으면 점착제의 초기 점착력이 저하될 수 있고, 함량이 너무 높으면 박리력의 조절이 어려워질 수 있다.The (meth)acrylate monomer having the alkyl group may be included in an amount of 55 to 95% by weight, preferably 60 to 80% by weight, based on the total weight of the monomer composition. If the content of the (meth)acrylate monomer having the alkyl group is too low, the initial adhesive strength of the adhesive may decrease, and if the content is too high, control of the peeling force may become difficult.
본 발명에서, 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체는 후술하는 이소시아네이트 화합물과 반응할 수 있는 히드록시기를 공중합체에 도입하여 점착력 및 응집력을 조절하는 역할을 한다. In the present invention, the (meth)acrylate monomer having the hydroxy group serves to control adhesion and cohesion by introducing a hydroxy group that can react with an isocyanate compound, which will be described later, into the copolymer.
상기 히드록시기를 갖는 (메타)아크릴레이트 단량체는, 예를 들어 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시부틸(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 8-히드록시옥틸(메타)아크릴레이트, 1,4-시클로헥산디메탄올모노(메타)아크릴레이트, 클로로-2-히드록시프로필아크릴레이트, 디에틸렌글리콜모노(메타)아크릴레이트, 프로필렌글리콜(메타)아크릴레이트 등을 1종 이상 포함할 수 있다. The (meth)acrylate monomer having the hydroxy group is, for example, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4- Hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 1,4-cyclohexanedimethanol mono (meth)acrylate, chloro-2- It may include one or more types of hydroxypropyl acrylate, diethylene glycol mono(meth)acrylate, and propylene glycol (meth)acrylate.
본 발명에 따르면, 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체의 히드록시기 위치에 따라 공중합체와 이소시아네이트 화합물 간의 반응성이 달라질 수 있다. 특히, 히드록시기를 갖는 (메타)아크릴레이트 단량체로서 2-히드록시에틸(메타)아크릴레이트 또는 4-히드록시부틸(메타)아크릴레이트를 사용하는 경우, UV 경화 후 점착제의 점착력이 크게 감소할 수 있으므로 바람직하다. According to the present invention, the reactivity between the copolymer and the isocyanate compound may vary depending on the position of the hydroxy group of the (meth)acrylate monomer having the hydroxy group. In particular, when 2-hydroxyethyl (meth)acrylate or 4-hydroxybutyl (meth)acrylate is used as a (meth)acrylate monomer having a hydroxy group, the adhesive strength of the adhesive may be greatly reduced after UV curing. desirable.
그 중에서도, 2-히드록시에틸(메타)아크릴레이트에 비해 2개의 탄소를 더 포함하는 4-히드록시부틸(메타)아크릴레이트를 이용하는 경우 단량체의 유연 효과에 의해 매우 높은 반응성을 나타낼 수 있으므로, UV 경화 후 점착제의 잔사가 남는 매우 효과적으로 개선할 수 있다. 또한, 4-히드록시부틸(메타)아크릴레이트를 이용하면 곁사슬의 길이 증가에 따라 얽힘 효과가 상승하여 자체적인 응집력이 강화될 수 있으므로 바람직하다.Among them, when using 4-hydroxybutyl (meth)acrylate, which contains two more carbons compared to 2-hydroxyethyl (meth)acrylate, it can exhibit very high reactivity due to the softening effect of the monomer, so UV It can be very effective in improving the adhesive residue that remains after curing. In addition, it is preferable to use 4-hydroxybutyl (meth)acrylate because the entanglement effect increases as the length of the side chain increases, thereby strengthening its own cohesion.
상기 히드록시기를 갖는 (메타)아크릴레이트 단량체는 단량체 조성물 전체 중량에 대하여 3 내지 30중량%, 바람직하게 5 내지 15중량% 포함될 수 있다. 특히, 히드록시기를 갖는 (메타)아크릴레이트 단량체가 8 내지 12중량% 포함되는 경우 점착제의 UV 경화 후 점착력을 효과적으로 낮출 수 있다는 측면에서 바람직하다. 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체의 함량이 너무 낮으면 점착제의 잔사가 심하고 코팅이 어려운 문제가 발생할 수 있다. 관련하여, 본 발명의 실시예를 통해, 히드록시기를 갖는 (메타)아크릴레이트 단량체의 함량이 5중량%인 경우에 비해 10중량%일 때 UV 경화 후 점착제의 점착력이 낮은 것을 확인할 수 있다.The (meth)acrylate monomer having the hydroxy group may be included in an amount of 3 to 30% by weight, preferably 5 to 15% by weight, based on the total weight of the monomer composition. In particular, the inclusion of 8 to 12% by weight of a (meth)acrylate monomer having a hydroxy group is preferable in that the adhesive strength can be effectively lowered after UV curing of the adhesive. If the content of the (meth)acrylate monomer having the hydroxy group is too low, adhesive residue may be severe and coating may be difficult. In relation, through examples of the present invention, it can be confirmed that the adhesive strength of the adhesive after UV curing is lower when the content of the (meth)acrylate monomer having a hydroxy group is 10% by weight compared to when the content is 5% by weight.
본 발명에서, 상기 불포화 카르복실산 단량체로는 아크릴산, 메타크릴산, 이타콘산, 말레인산, 말레인산 무수물 등을 사용할 수 있다. 이 중에서도, 아크릴산을 이용하는 경우 초기 점착력을 향상시킬 수 있으므로 바람직하다.In the present invention, acrylic acid, methacrylic acid, itaconic acid, maleic acid, maleic anhydride, etc. can be used as the unsaturated carboxylic acid monomer. Among these, the use of acrylic acid is preferable because it can improve initial adhesive strength.
상기 불포화 카르복실산 단량체는, 단량체 조성물 전체 중량에 대하여 1 내지 20중량%, 바람직하게는 3 내지 15중량% 포함될 수 있다. The unsaturated carboxylic acid monomer may be included in an amount of 1 to 20% by weight, preferably 3 to 15% by weight, based on the total weight of the monomer composition.
본 발명에서, 상기 아크릴계 공중합체는 상기 단량체 외에도 공중합 가능한 다른 단량체, 예를 들어 시클로알킬기를 갖는 (메타)아크릴레이트 단량체, 방향족 (메타)아크릴레이트 단량체 등이 함께 부가되어 중합된 것일 수 있다. In the present invention, the acrylic copolymer may be polymerized by adding other copolymerizable monomers, for example, a (meth)acrylate monomer having a cycloalkyl group, an aromatic (meth)acrylate monomer, etc., in addition to the monomer.
본 발명에서, 상기 시클로알킬기를 갖는 (메타)아크릴레이트 단량체는 탄소수 6 내지 20의 시클로알킬기를 가질 수 있다. 예를 들어, 상기 시클로알킬기를 갖는 (메타)아크릴레이트 단량체는 이소보닐(메타)아크릴레이트, 사이클로헥실(메타)아크릴레이트 등을 1종 이상 포함할 수 있다. In the present invention, the (meth)acrylate monomer having a cycloalkyl group may have a cycloalkyl group having 6 to 20 carbon atoms. For example, the (meth)acrylate monomer having the cycloalkyl group may include one or more types of isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, etc.
상기 시클로알킬기를 갖는 (메타)아크릴레이트는, 공중합체를 구성하는 단량체 전체 중량에 대하여 5 내지 30중량%, 바람직하게는 10 내지 20중량% 포함될 수 있다. The (meth)acrylate having the cycloalkyl group may be included in an amount of 5 to 30% by weight, preferably 10 to 20% by weight, based on the total weight of monomers constituting the copolymer.
상기 단량체 외에도, 필요에 따라 방향족 (메타)아크릴레이트 단량체를 부가하여 중합 반응을 수행할 수 있다.In addition to the above monomers, the polymerization reaction can be performed by adding aromatic (meth)acrylate monomers, if necessary.
본 발명에서, 상기 아크릴계 공중합체는 각 단량체를 혼합하고 중합 반응을 수행하여 제조될 수 있다. 예를 들어, 상기 중합 반응은 고형분 함량이 20 내지 60중량%, 예를 들어 30 내지 50중량%이 될 때까지 수행될 수 있다.In the present invention, the acrylic copolymer can be prepared by mixing each monomer and performing a polymerization reaction. For example, the polymerization reaction may be performed until the solid content is 20 to 60% by weight, for example, 30 to 50% by weight.
상기 중합은 용액 중합법으로 수행될 수 있으며, 중합에 사용되는 용매로는 메틸아세테이트, 에틸아세테이트, 부틸아세테이트, 톨루엔, 크실렌, 벤젠, 아세톤, 메틸에틸케톤 등을 1종 이상 이용할 수 있다.The polymerization can be performed by a solution polymerization method, and one or more solvents used in the polymerization include methyl acetate, ethyl acetate, butylacetate, toluene, xylene, benzene, acetone, and methyl ethyl ketone.
상기 용액 중합은, 용매에 단량체를 투입하고 1 내지 24시간, 예를 들어 3 내지 10시간 동안 교반함으로써 수행될 수 있다. 이 때, 중합 온도는 실온 내지 150℃, 예를 들어 50 내지 120℃의 범위에서 적절하게 선택할 수 있다. 또한, 중합 반응의 개시를 위해 아조계 중합개시제, 과산화물과 같은 중합개시제를 이용할 수 있다.The solution polymerization can be performed by adding monomers to a solvent and stirring for 1 to 24 hours, for example, 3 to 10 hours. At this time, the polymerization temperature can be appropriately selected in the range of room temperature to 150°C, for example, 50 to 120°C. Additionally, a polymerization initiator such as an azo-based polymerization initiator or peroxide can be used to initiate the polymerization reaction.
본 발명에서, 상기 아크릴계 공중합체는 탄소-탄소 이중 결합을 갖는 이소시아네이트 화합물과 반응할 수 있다.In the present invention, the acrylic copolymer can react with an isocyanate compound having a carbon-carbon double bond.
상기 이소시아네이트 화합물은 공중합체에 포함되는 히드록시기와 반응할 수 있는 관능기를 갖는 것으로서, 예를 들어, (메타)아크릴로일옥시 이소시아네이트, (메타)아크릴로일옥시메틸 이소시아네이트, (메타)아크릴로일옥시에틸 이소시아네이트, (메타)아크릴로일옥시프로필 이소시아네이트, (메타)아크릴로일 이소시아네이트 등을 1종 이상 포함할 수 있다.The isocyanate compound has a functional group that can react with the hydroxy group contained in the copolymer, for example, (meth)acryloyloxy isocyanate, (meth)acryloyloxymethyl isocyanate, (meth)acryloyloxy It may include one or more types of ethyl isocyanate, (meth)acryloyloxypropyl isocyanate, (meth)acryloyl isocyanate, etc.
바람직하게, 상기 이소시아네이트 화합물은 아크릴로일옥시에틸 이소시아네이트 및 메타크릴로일옥시에틸 이소시아네이트 중 1종 이상을 포함할 수 있다. 아크릴레이트 구조를 이용하는 경우 UV 경화에 의한 반응 속도가 빠르며, 메타크릴레이트 구조를 이용하는 경우 구조적 안정성을 개선할 수 있다.Preferably, the isocyanate compound may include one or more of acryloyloxyethyl isocyanate and methacryloyloxyethyl isocyanate. When an acrylate structure is used, the reaction rate by UV curing is fast, and when a methacrylate structure is used, structural stability can be improved.
본 발명에서, 이소시아네이트 화합물로서 메타크릴로일옥시에틸 이소시아네이트를 사용하는 경우, 곁사슬의 길이 증가에 따라 점착제가 UV 경화 후 매우 낮은 점착력을 나타낼 수 있고 경화 후 잔사가 남지 않는다는 면에서 바람직하다. In the present invention, when methacryloyloxyethyl isocyanate is used as the isocyanate compound, it is preferable in that the adhesive can exhibit very low adhesive strength after UV curing as the length of the side chain increases and no residue remains after curing.
또한, 공중합체를 구성하는 히드록시기를 갖는 (메타)아크릴레이트 단량체의 종류 및 함량에 따라 상기 이소시아네이트 화합물과의 반응성이 크게 향상될 수 있으며, 이에 따라 UV 경화 전후의 점착력 차이를 극대화시키면서, UV 경화 후 다이싱(dicing)에 이용될 수 있을 정도로 낮은 점착력을 나타내도록 조절할 수 있다.In addition, depending on the type and content of the (meth)acrylate monomer having a hydroxy group constituting the copolymer, the reactivity with the isocyanate compound can be greatly improved, thereby maximizing the difference in adhesion before and after UV curing, and after UV curing. It can be adjusted to exhibit adhesion low enough to be used for dicing.
특히, 본 발명에 따르면 히드록시기를 갖는 (메타)아크릴레이트 단량체가 4-히드록시부틸아크릴레이트이고 이소시아네이트 화합물이 메타크릴로일옥시에틸 이소시아네이트일 때 점착력 조절 효과를 극대화할 수 있다. 이 경우, 긴 곁사슬과 메타크릴레이트 구조의 시너지가 발휘되어 분자내 결합에 비해 분자간 결합이 우세하게 나타나므로, 중합체 구조 자체의 안정성도 우수하면서 UV 경화에 의해 점착제의 점착력이 더욱 민감하게 변화할 수 있다.In particular, according to the present invention, the adhesion control effect can be maximized when the (meth)acrylate monomer having a hydroxy group is 4-hydroxybutylacrylate and the isocyanate compound is methacryloyloxyethyl isocyanate. In this case, the synergy between the long side chain and the methacrylate structure is exerted, and intermolecular bonds are dominant over intramolecular bonds, so the stability of the polymer structure itself is excellent and the adhesive strength of the adhesive can be changed more sensitively by UV curing. there is.
본 발명의 점착제 제조용 조성물에서, 상기 이소시아네이트 화합물은 상기 아크릴계 공중합체 100중량부에 대하여 0.5 내지 15중량부, 바람직하게 1 내지 10중량부, 예를 들어 1.5 내지 8중량부 포함될 수 있다. 상기 함량은 아크릴계 공중합체에 포함되는 히드록시기의 양 및 사슬의 길이에 따라 달라질 수 있으며, 단량체 종류에 따라 1 내지 5중량부, 바람직하게 1.5 내지 4중량부일 때 우수한 점착력 조절 효과가 발휘될 수 있다.In the composition for producing an adhesive of the present invention, the isocyanate compound may be included in an amount of 0.5 to 15 parts by weight, preferably 1 to 10 parts by weight, for example, 1.5 to 8 parts by weight, based on 100 parts by weight of the acrylic copolymer. The content may vary depending on the amount of hydroxy groups included in the acrylic copolymer and the length of the chain, and an excellent adhesion control effect can be achieved when it is 1 to 5 parts by weight, preferably 1.5 to 4 parts by weight, depending on the type of monomer.
또한, 상기 이소시아네이트 화합물은 공중합체에 포함되는 히드록시기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대해 20 내지 80중량부 포함될 수 있다. Additionally, the isocyanate compound may be included in an amount of 20 to 80 parts by weight based on 100 parts by weight of the (meth)acrylate monomer having a hydroxy group included in the copolymer.
본 발명에서, 이소시아네이트 화합물의 함량이 너무 낮으면 반응이 제대로 진행되지 않아 잔사 발생 및 픽업성 저하의 원인이 될 수 있으며, 이소시아네이트 화합물의 함량이 너무 높으면 곁사슬의 길이가 길어짐에 따라 패킹(packing)되는 중합체가 증가하고, 상대적으로 이동성(mobility)이 감소하여 중합체의 젖음 현상(wetting)이 저하되므로 초기 점착력이 감소할 수 있다.In the present invention, if the content of the isocyanate compound is too low, the reaction may not proceed properly, which may cause residue generation and deterioration of pick-up performance, and if the content of the isocyanate compound is too high, the length of the side chain increases, resulting in packing. As the polymer increases and its mobility relatively decreases, the wetting of the polymer decreases, so the initial adhesion may decrease.
본 발명에서, 상기 이소시아네이트 화합물의 바람직한 함량은 이소시아네이트 화합물의 종류와 공중합체에 포함되는 히드록시기를 갖는 (메타)아크릴레이트 단량체의 종류 및 함량에 따라 달라질 수 있다. 예를 들어, 아크릴로일옥시에틸 이소시아네이트를 이용하는 경우 함량에 따른 점착력 차이가 크지 않지만, 메타크릴로일옥시에틸 이소시아네이트를 이용하는 경우 히드록시기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대해 20 내지 60중량부, 바람직하게 25 내지 50중량부, 예를 들어 30 내지 40중량부일 때 초기 점착력 증가 및 UV 경화 후 점착력 감소 효과가 가장 크게 나타날 수 있다.In the present invention, the preferred content of the isocyanate compound may vary depending on the type of the isocyanate compound and the type and content of the (meth)acrylate monomer having a hydroxy group included in the copolymer. For example, when using acryloyloxyethyl isocyanate, the difference in adhesion depending on the content is not large, but when using methacryloyloxyethyl isocyanate, the amount is 20 to 60 parts by weight for 100 parts by weight of (meth)acrylate monomer having a hydroxy group. parts, preferably 25 to 50 parts by weight, for example, 30 to 40 parts by weight, the effect of increasing initial adhesion and reducing adhesion after UV curing may be greatest.
본 발명에서, 상기 아크릴계 공중합체와 이소시아네이트 화합물을 반응시켜 바인더 수지를 제조할 수 있다. In the present invention, a binder resin can be produced by reacting the acrylic copolymer with an isocyanate compound.
상기 아크릴계 공중합체 및 이소시아네이트 화합물의 반응은 실온 내지 90℃, 예를 들어 40 내지 60℃에서, 10분 내지 10시간, 예를 들어 30분 내지 2시간 동안 수행될 수 있다. 상기 반응에 의해 아크릴계 공중합체의 측쇄에 광경화성 관능기를 도입하여 바인더 수지를 제조할 수 있다.The reaction of the acrylic copolymer and the isocyanate compound may be performed at room temperature to 90°C, for example, 40 to 60°C, for 10 minutes to 10 hours, for example, 30 minutes to 2 hours. Through the above reaction, a binder resin can be manufactured by introducing a photocurable functional group into the side chain of the acrylic copolymer.
이에 따라, 본 발명은 또한, 상기 광감응성 점착제 제조용 조성물을 반응시켜 제조된 바인더 수지, 및 광개시제를 포함하는 광반응성 점착제를 제공할 수 있다.Accordingly, the present invention can also provide a photoreactive adhesive containing a binder resin prepared by reacting the composition for producing a photosensitive adhesive, and a photoinitiator.
본 발명에서, 상기 점착제 제조용 조성물을 이용하면 자가 가교 구조를 가지며 자외선 조사에 의한 점착력 저하 효과가 극대화된 바인더 수지를 형성할 수 있으므로, 광반응을 위해 점착제에 포함되는 올리고머의 함량을 최소화할 수 있고, 올리고머에 의한 내구성 변화 및 점착제의 경시변화를 방지할 수 있다.In the present invention, by using the composition for producing an adhesive, it is possible to form a binder resin that has a self-crosslinking structure and maximizes the effect of reducing adhesive strength by ultraviolet irradiation, so that the content of oligomers contained in the adhesive for photoreaction can be minimized. , it can prevent changes in durability caused by oligomers and changes in adhesive over time.
본 발명에서, 광개시제(photoinitiator)는 바인더 수지에 자외선(UV)이 조사되는 경우 라디칼을 형성하여 경화 반응을 개시함으로써 점착제의 박리력을 감소시키는 역할을 한다.In the present invention, the photoinitiator serves to reduce the peeling force of the adhesive by forming radicals and initiating a curing reaction when the binder resin is irradiated with ultraviolet (UV) rays.
본 발명에서, 상기 광개시제로는 벤조인, 벤조인메틸에테르, 벤조인에틸에테르, 벤조인이소프로필에테르, 벤조인-n-부틸에테르, 벤조인이소부틸에테르, 아세토페논, 히드록시디메틸아세토페논, 디메틸아미노아세토페논, 디메톡시-2-페닐아세토페논, 3-메틸아세토페논, 2,2-디메톡시-2-페닐아세토페논, 2,2-디에톡시-2-페닐아세토페논, 4-크로놀로세토페논, 4,4-디메톡시아세토페논, 2-히드록시-2-메틸-1-페닐프로판-1-온, 4-히드록시시클로페닐케톤, 1-히드록시시클로헥실페닐케톤, 2-메틸-1-[4-(메틸티오)페닐]-2-모르폴리노-프로판-1-온, 4-(2-히드록시에톡시)페닐-2-(히드록시-2-프로필)케톤, 벤조페논, p-페닐벤조페논, 4,4-디아미노벤조페논, 4,4'-디에틸아미노벤조페논, 디클로로벤조페논, 안트라퀴논, 2-메틸안트라퀴논, 2-에틸안트라퀴논, 2-t-부틸안트라퀴논, 2-아미노안트라퀴논, 2-메틸티옥산톤, 2-에틸티옥산톤, 2-클로로티옥산톤, 2,4-디메틸티옥산톤, 2,4-디에틸티옥산톤, 벤질디메틸케탈, 디페닐케톤벤질디메틸케탈, 아세토페논디메틸케탈, p-디메틸아미노벤조산에스테르, 2,4,6-트리메틸벤조일-디페닐-포스핀옥사이드, 플루오렌, 트리페닐아민, 카바졸 등을 1종 이상 사용할 수 있다.In the present invention, the photoinitiator includes benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, acetophenone, hydroxydimethylacetophenone, Dimethylaminoacetophenone, dimethoxy-2-phenylacetophenone, 3-methylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 4-chronolo Cetophenone, 4,4-dimethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4-hydroxycyclophenyl ketone, 1-hydroxycyclohexylphenyl ketone, 2-methyl -1-[4-(methylthio)phenyl]-2-morpholino-propan-1-one, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)ketone, benzo Phenone, p-phenylbenzophenone, 4,4-diaminobenzophenone, 4,4'-diethylaminobenzophenone, dichlorobenzophenone, anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-t -Butylanthraquinone, 2-aminoanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone , Benzyl dimethyl ketal, diphenyl ketone benzyl dimethyl ketal, acetophenone dimethyl ketal, p-dimethylaminobenzoic acid ester, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, fluorene, triphenylamine, carbazole, etc. One or more types can be used.
상기 광개시제는 바인더 수지 100중량부에 대하여 0.1 내지 10중량부, 바람직하게는 0.2 내지 5중량부, 더 바람직하게는 0.5 내지 2중량부의 양으로 사용될 수 있다. 광개시제의 함량이 너무 낮으면 자외선에 의한 경화 반응이 제대로 진행되지 않아 픽업성이 저하될 수 있다. 또한, 광개시제의 함량이 너무 높으면, 경화 후 점착제 중 분자량이 낮은 성분이 잔존하여 잔사의 원인이 될 수 있다.The photoinitiator may be used in an amount of 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, and more preferably 0.5 to 2 parts by weight, based on 100 parts by weight of the binder resin. If the photoinitiator content is too low, the curing reaction by ultraviolet rays may not proceed properly and the pick-up performance may be reduced. Additionally, if the photoinitiator content is too high, components with low molecular weight may remain in the adhesive after curing, causing residue.
본 발명의 일 실시 형태에서, 점착제는 UV 경화성 올리고머(oligomer)를 더 포함할 수 있다. 이 경우, 바인더 수지와 UV 경화성 올리고머의 가교반응을 유도하여 자외선 조사 후 점착력이 크게 감소하도록 조절할 수 있다.In one embodiment of the present invention, the adhesive may further include a UV curable oligomer. In this case, by inducing a crosslinking reaction between the binder resin and the UV-curable oligomer, the adhesion can be adjusted to greatly decrease after UV irradiation.
본 발명에서, 상기 UV 경화성 올리고머는 2 내지 12관능의 (메타)아크릴레이트 화합물을 1종 이상 포함할 수 있으며, 바람직하게는 6관능 이상의 (메타)아크릴레이트 화합물 및 2 내지 5관능의 (메타)아크릴레이트 화합물을 포함할 수 있다.In the present invention, the UV curable oligomer may include one or more types of (meth)acrylate compounds having 2 to 12 functionality, preferably 6 or more functional (meth)acrylate compounds and 2 to 5 functional (meth)acrylate compounds. It may contain an acrylate compound.
본 발명에서, 상기 UV 경화성 올리고머는 예를 들어, 트리메틸올프로판 트리아크릴레이트, 테트라메틸올메탄 테트라아크릴레이트, 펜타에리스리톨 헥사아크릴레이트, 펜타에리스리톨 테트라아크릴레이트, 디펜타디에리스 리톨모노히드록시 펜타아크릴레이트, 디펜타에리스리톨 헥사아크릴레이트, 1,4-부틸렌글리콜 디아크릴레이트, 1,6-헥산디올 디아크릴레이트, 폴리에틸렌글리콜 디아크릴레이트 등을 1종 이상 포함할 수 있다.In the present invention, the UV curable oligomer is, for example, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, pentaerythritol hexaacrylate, pentaerythritol tetraacrylate, dipentadierythritol monohydroxy pentaacrylate. It may include one or more types of acid, dipentaerythritol hexaacrylate, 1,4-butylene glycol diacrylate, 1,6-hexanediol diacrylate, and polyethylene glycol diacrylate.
이외에, 본 발명의 점착제는 필요에 따라 점착 부여제, 커플링제, 분산제, 가교제 등의 첨가제를 더 포함할 수 있다.In addition, the adhesive of the present invention may further include additives such as a tackifier, coupling agent, dispersant, and crosslinking agent, if necessary.
본 발명에 따른 점착제는 자가 가교 구조를 가지므로 UV 경화 반응에 의해 중합체의 구조가 크게 변화하여 UV 경화 전후의 높은 점착력 변화를 유도할 수 있으며, 특히 공중합체를 구성하는 단량체와 이소시아네이트 화합물의 종류 및 함량을 조절함으로써 초기 점착력을 극대화하면서 UV 경화 후의 점착력을 최소화할 수 있다. 이에 따라, 본 발명을 반도체 다이싱 테이프로 이용하면 다이싱 공정에서 칩의 비산을 방지하고, 점착제의 잔사를 억제할 수 있으며 칩의 픽업성을 향상시킬 수 있다. Since the adhesive according to the present invention has a self-crosslinking structure, the structure of the polymer changes significantly due to UV curing reaction, which can lead to a high change in adhesive strength before and after UV curing. In particular, the types of monomers and isocyanate compounds that make up the copolymer and By adjusting the content, the initial adhesion can be maximized while the adhesion after UV curing can be minimized. Accordingly, if the present invention is used as a semiconductor dicing tape, scattering of chips can be prevented during the dicing process, adhesive residue can be suppressed, and chip pick-up performance can be improved.
이에 따라, 본 발명은 또한, 상기 점착제 제조용 조성물을 이용하여 제조된 점착필름을 제공할 수 있다.Accordingly, the present invention can also provide an adhesive film manufactured using the composition for producing an adhesive.
본 발명의 점착필름은 기재, 및 본 발명의 점착제 제조용 조성물을 이용하여 제조된 바인더 수지 및 광개시제를 포함하는 점착제층을 포함한다. 상기 점착필름은 초기 점착력이 우수하면서 자외선 조사에 의해 점착력이 크게 감소하므로, 반도체 패키징 공정의 다이싱용 점착필름으로서 효과적으로 사용될 수 있다.The adhesive film of the present invention includes a base material and an adhesive layer containing a binder resin and a photoinitiator prepared using the composition for producing an adhesive of the present invention. The adhesive film has excellent initial adhesive strength and its adhesive strength is greatly reduced by ultraviolet irradiation, so it can be effectively used as an adhesive film for dicing in the semiconductor packaging process.
상기 점착필름에서, 기재는 익스팬딩이 가능하면서 자외선을 투과하는 특성을 갖는 것을 사용할 수 있다. 기재의 소재는 특별히 제한되지 않으며, 예를 들어 폴리에틸렌, 폴리프로필렌과 같은 폴리올레핀계 수지, 에틸렌/프로필렌 공중합체, 에틸렌/(메타)아크릴산 공중합체, 에틸렌/아세트산비닐 공중합체, 에틸렌-부텐 공중합체와 같은 폴리올레핀 공중합체 수지, 폴리에스테르계 수지, 폴리이미드계 수지, 폴리스티렌계 수지, 폴리비닐알콜계 수지, 폴리에테르계 수지 등이 사용될 수 있다. 또한, 상기 기재에는 필요에 따라 방전처리, 매트 처리, 프라이머 처리, 가교 처리 등 공지의 물리적 또는 화학적 처리를 수행할 수 있다.In the adhesive film, a substrate that can expand and has the property of transmitting ultraviolet rays can be used. The material of the base material is not particularly limited and includes, for example, polyolefin resins such as polyethylene and polypropylene, ethylene/propylene copolymer, ethylene/(meth)acrylic acid copolymer, ethylene/vinyl acetate copolymer, ethylene-butene copolymer, and The same polyolefin copolymer resin, polyester resin, polyimide resin, polystyrene resin, polyvinyl alcohol resin, polyether resin, etc. can be used. Additionally, the substrate may be subjected to known physical or chemical treatments such as discharge treatment, mat treatment, primer treatment, and cross-linking treatment, as necessary.
상기 기재의 두께는 특별히 한정되지 않으며, 예를 들어 10 내지 500㎛, 바람직하게 30 내지 300㎛일 수 있다. 기재의 두께가 너무 얇으면 다이싱 공정의 안정성이 떨어질 수 있고, 두께가 너무 두꺼우면 연신율이 떨어지고 공정의 정밀성이 저하될 수 있다.The thickness of the substrate is not particularly limited and may be, for example, 10 to 500 μm, preferably 30 to 300 μm. If the thickness of the substrate is too thin, the stability of the dicing process may decrease, and if the thickness is too thick, the elongation rate may decrease and the precision of the process may decrease.
상기 점착필름에서, 상기 점착제층은 바인더 수지 및 광개시제가 혼합된 점착제를 코팅하여 형성될 수 있다.In the adhesive film, the adhesive layer may be formed by coating an adhesive mixed with a binder resin and a photoinitiator.
상기 점착제층은 자외선 조사 전에는 점착력이 높고, 자외선 조사 후에는 점착력이 크게 감소되는 것이 바람직하다. 본 발명의 점착제층은 자외선 조사 전 600 내지 2,000gf/25mm, 바람직하게 800gf/25mm 이상, 보다 더 바람직하게 1,000gf/25mm 이상의 박리력을 나타낼 수 있으며, 자외선 조사 후 10 내지 400gf/25mm, 바람직하게 300gf/25mm 이하, 보다 더 바람직하게 200gf/25mm 이하의 박리력을 나타낼 수 있다.It is preferable that the adhesive layer has high adhesive strength before irradiation with ultraviolet rays, and that the adhesive strength is greatly reduced after irradiation with ultraviolet rays. The adhesive layer of the present invention may exhibit a peeling force of 600 to 2,000 gf/25mm, preferably 800gf/25mm or more, more preferably 1,000gf/25mm or more before irradiation with ultraviolet rays, and 10 to 400gf/25mm, preferably 10 to 400gf/25mm, after ultraviolet irradiation. It can exhibit a peeling force of 300gf/25mm or less, more preferably 200gf/25mm or less.
상기 점착제층의 두께는 200㎛ 이하, 바람직하게 1 내지 100㎛, 예를 들어 3 내지 50㎛일 수 있다. The thickness of the adhesive layer may be 200 μm or less, preferably 1 to 100 μm, for example, 3 to 50 μm.
상기 점착제층은, 기재 상에 본 발명의 점착제를 코팅하는 방법, 또는 이형 필름 상에 점착제를 코팅하여 점착제층을 형성한 후 기재 상에 전사하는 방법 등을 통해 형성될 수 있다.The adhesive layer may be formed through a method of coating the adhesive of the present invention on a substrate, or a method of coating the adhesive on a release film to form an adhesive layer and then transferring it onto the substrate.
상기 점착제층은 다이 코팅, 그라비아 코팅, 리버스 코팅 등 공지의 코팅 방법으로 점착제를 코팅한 다음 건조시켜 형성될 수 있다. 예를 들어, 점착제 코팅 후 실온 내지 150℃의 온도에서 10초 내지 1시간 동안 건조시킬 수 있다. 또한, 점착제의 가교 반응을 충분히 진행시키기 위한 에이징(aging) 공정을 추가로 수행하는 것도 가능하다.The adhesive layer can be formed by coating the adhesive with a known coating method such as die coating, gravure coating, or reverse coating and then drying it. For example, after coating with the adhesive, it can be dried at a temperature of room temperature to 150°C for 10 seconds to 1 hour. In addition, it is possible to additionally perform an aging process to sufficiently advance the crosslinking reaction of the adhesive.
본 발명의 점착필름은 반도체 패키징 공정에 이용되는 다이싱 테이프로 효과적으로 사용될 수 있다. 본 발명은 또한, 상기 점착필름 상에 접착필름이 형성된 다이싱-다이본딩 필름을 제공할 수 있고, 상기 다이싱-다이본딩 필름을 포함하는 반도체 웨이퍼를 제공할 수 있다. 이 때, 상기 접착필름은 점착제와 달리 자외선 조사에 의해 강한 접착력을 나타내는 접착제를 이용하여 형성될 수 있다.The adhesive film of the present invention can be effectively used as a dicing tape used in the semiconductor packaging process. The present invention can also provide a dicing-die bonding film in which an adhesive film is formed on the adhesive film, and can provide a semiconductor wafer including the dicing-die bonding film. At this time, the adhesive film may be formed using an adhesive that exhibits strong adhesive force when irradiated with ultraviolet rays, unlike an adhesive.
본 발명을 이용하면 자외선 조사 전 강한 점착력을 유지하면서 자외선 조사 후 점착력을 크게 감소시킬 수 있으므로, 반도체 패키징 공정을 매우 효율적으로 수행할 수 있다. 구체적으로, 본 발명의 점착제를 다이싱 테이프의 점착제층에 적용하면 반도체의 다이싱 공정에서 가해지는 충격 및 수압에 의한 칩의 비산을 효과적으로 방지할 수 있고, 자외선 조사 후에는 점착력이 매우 낮아져 박리 후 칩에 잔사가 남지 않으며 칩을 용이하게 픽업할 수 있다. Using the present invention, the adhesive strength can be greatly reduced after UV irradiation while maintaining strong adhesive strength before UV irradiation, so the semiconductor packaging process can be performed very efficiently. Specifically, applying the adhesive of the present invention to the adhesive layer of a dicing tape can effectively prevent chips from scattering due to shock and water pressure applied during the dicing process of a semiconductor, and after irradiation with ultraviolet rays, the adhesive strength becomes very low, causing damage after peeling. There is no residue left on the chips and the chips can be easily picked up.
실시예Example
이하 실시예를 통하여 본 발명을 보다 상세하게 설명한다. 단, 이들 실시예는 본 발명을 예시적으로 설명하기 위하여 일부 실험방법과 조성을 나타낸 것으로, 본 발명의 범위가 이러한 실시예에 제한되는 것은 아니다.The present invention will be described in more detail through examples below. However, these examples show some experimental methods and compositions to illustratively illustrate the present invention, and the scope of the present invention is not limited to these examples.
제조예: 광감응성 점착제 제조Manufacturing example: Manufacturing of light-sensitive adhesive
1차 반응: 아크릴계 공중합체 제조First reaction: Preparation of acrylic copolymer
이소시아네이트(NCO) 아크릴레이트를 반응시키기 위해 히드록시기(-OH)를 갖고 있는 공중합체를 제조하였다. To react isocyanate (NCO) acrylate, a copolymer containing a hydroxy group (-OH) was prepared.
2-에틸헥실아크릴레이트(2-ethylhexyl acrylate, 2-EHA)와 아크릴산(acrylic acid, AA)을 기본 단량체 성분으로 하였으며, 히드록시기를 도입하기 위한 단량체로서 2-히드록시에틸아크릴레이트(2-hydroxyethyl acrylate, 2-HEA) 또는 4-히드록시부틸 아크릴레이트(4-hydroxybutyl acrylate, 4-HBA)를 이용하고, 이소보닐 아크릴레이트(isobornyl acrylate, IBA)를 함께 첨가하여 반응을 수행하였다. 2-ethylhexyl acrylate (2-EHA) and acrylic acid (AA) are used as basic monomer components, and 2-hydroxyethyl acrylate is used as a monomer to introduce a hydroxy group. , 2-HEA) or 4-hydroxybutyl acrylate (4-HBA) was used, and isobornyl acrylate (IBA) was added together to perform the reaction.
상기 단량체들을 에틸 아세테이트(ethyl acetate, EA) 용매에 넣고, 85℃에서 6시간 동안 교반하여 중합 반응을 수행하였다. 상기 중합 반응에서, 전체 고형분은 40%로 설정하였다.The monomers were added to ethyl acetate (EA) solvent and stirred at 85°C for 6 hours to perform a polymerization reaction. In the polymerization reaction, the total solid content was set to 40%.
각 성분의 함량을 아래 표 1과 같이 조절하여 4개의 공중합체 샘플을 제조하였다. 표 1에서, 각 성분의 함량은 중량부 기준으로 나타내었다.Four copolymer samples were prepared by adjusting the content of each component as shown in Table 1 below. In Table 1, the content of each ingredient is expressed in parts by weight.
2차 반응: 광감응성 점착제 제조Secondary reaction: manufacturing photosensitive adhesive
상기 1차 반응을 통해 제조된 공중합체를 기본으로 하여, 이소시아네이트 화합물로 아크릴로일옥시에틸 이소시아네이트(acryloyloxyethyl isocyanate, AOI) 또는 메타크릴로일옥시에틸 이소시아네이트(methacryloyloxyethyl isocyanate, MOI)를 첨가하고, 표 2의 조성으로 바인더 수지를 제조하였다. 표 2에서, 각 성분의 함량은 중량부 기준으로 나타내었다.Based on the copolymer prepared through the first reaction, acryloyloxyethyl isocyanate (AOI) or methacryloyloxyethyl isocyanate (MOI) was added as an isocyanate compound, Table 2 A binder resin was prepared with the composition. In Table 2, the content of each ingredient is expressed in parts by weight.
1차 중합 반응 완료 후 이소시아네이트 화합물을 투입하여 50℃에서 1시간 동안 반응을 수행하고, 점도 및 분자량 변화를 통해 반응 정도를 확인하였다. 광개시제로는 2,4,6-트리메틸벤조일-디페닐-포스핀옥사이드(TPO)를 이용하고, 광개시제의 함량은 1phr (parts per hundred resin)로 하여 점착제를 제조하였다.After completing the first polymerization reaction, the isocyanate compound was added and the reaction was performed at 50°C for 1 hour, and the degree of reaction was confirmed through changes in viscosity and molecular weight. An adhesive was prepared using 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO) as a photoinitiator, and setting the photoinitiator content to 1phr (parts per hundred resin).
실험예: 점착제의 UV 조사 전후 점착력 변화 측정Experimental example: Measurement of change in adhesive strength before and after UV irradiation of adhesive
실험 방법Experimental method
제조예의 방법으로 점착제를 제조하고, 점착제를 건조 후 기준 25㎛ 두께로 PET 필름 위에 코팅하였다. 이후, 120℃에서 5분간 건조시켜 용제를 모두 제거하여 점착제층을 형성한 다음 이형필름을 덮어주어 샘플을 준비하였다. The adhesive was prepared by the method of the manufacturing example, and the adhesive was dried and coated on PET film to a standard thickness of 25㎛. Afterwards, the sample was prepared by drying at 120°C for 5 minutes to remove all solvent to form an adhesive layer and then covering it with a release film.
형성된 점착제층에 대해 박리력(peel strength, gf/25mm)을 측정하여 초기 점착력을 확인하였다. 그 후, 자외선(UV)을 1J/cm2의 광량으로 조사한 다음 동일한 방법으로 박리력을 측정하여 경화 후 점착력을 확인하였다. The initial adhesive strength was confirmed by measuring the peel strength (gf/25mm) of the formed adhesive layer. Afterwards, ultraviolet rays (UV) were irradiated at a light quantity of 1 J/cm 2 and the peeling force was measured in the same manner to confirm the adhesive strength after curing.
초기 점착력 및 경화 후 점착력을 비교하여 UV 경화 전후의 점착력 변화를 확인하고, 표면 잔사를 관찰하여 점착제의 자가 가교 특성을 확인하였다.The initial adhesive strength and the adhesive strength after curing were compared to confirm the change in adhesive strength before and after UV curing, and the self-crosslinking characteristics of the adhesive were confirmed by observing the surface residue.
실험예 1: 공중합체 샘플 1을 이용한 점착제의 UV 경화 전후 점착력 측정Experimental Example 1: Measurement of adhesion before and after UV curing of adhesive using copolymer sample 1
2-HEA 단량체를 5중량% 포함하는 공중합체 샘플 1을 이용하여 제조된 점착제 샘플 1-1 내지 1-4의 경우, 코팅이 어렵고 잔사가 심하여 점착력 측정이 불가능하였다.In the case of adhesive samples 1-1 to 1-4 prepared using copolymer sample 1 containing 5% by weight of 2-HEA monomer, coating was difficult and the residue was so severe that adhesive force measurement was impossible.
실험예 2: 공중합체 샘플 2를 이용한 점착제의 UV 경화 전후 점착력 측정Experimental Example 2: Measurement of adhesion before and after UV curing of adhesive using copolymer sample 2
2-HEA 단량체를 10중량% 포함하는 공중합체 샘플 2를 이용하여 제조된 점착제 샘플 2-1 내지 2-4에 대해 점착제층의 점착력을 평가하였다.The adhesive strength of the adhesive layer was evaluated for adhesive samples 2-1 to 2-4 prepared using copolymer sample 2 containing 10% by weight of 2-HEA monomer.
도 3은 점착제 샘플 2-1 및 2-2의 UV 조사 전후 박리력(a) 및 샘플 2-3 및 2-4의 UV 조사 전후 박리력(b) 측정 결과를 나타낸 것이며, 도 4는 상기 결과를 토대로 UV 조사 전후의 박리력 변화를 그래프로 나타낸 것이다.Figure 3 shows the results of measuring the peeling force (a) before and after UV irradiation of adhesive samples 2-1 and 2-2 and the peeling force (b) before and after UV irradiation of samples 2-3 and 2-4, and Figure 4 shows the results. Based on this, the change in peeling force before and after UV irradiation is shown graphically.
2-HEA를 이용한 공중합체 샘플 2 기반 점착제의 경우, 이소시아네이트 화합물의 함량이 증가함에 따라 점착력이 감소하는 경향이 확인되었다. 상기 결과로부터, UV 반응 전 곁사슬의 길이가 길어짐에 따라 패킹(packing)되는 고분자가 증가하고 이동성(mobility)이 감소하여 점착력이 감소하는 것을 알 수 있었다. 또한, 시스템 내에 관능기의 수 증가에 따라 UV 반응 후 점착력이 감소하는 결과를 확인할 수 있었다.In the case of the adhesive based on copolymer sample 2 using 2-HEA, it was confirmed that the adhesive strength tended to decrease as the content of the isocyanate compound increased. From the above results, it was found that as the length of the side chain before UV reaction increases, the number of polymers packed increases, mobility decreases, and adhesive strength decreases. In addition, it was confirmed that as the number of functional groups in the system increased, the adhesive strength decreased after UV reaction.
실험예 3: 공중합체 샘플 3을 이용한 점착제의 UV 경화 전후 점착력 측정Experimental Example 3: Measurement of adhesion before and after UV curing of adhesive using copolymer sample 3
4-HBA 단량체를 5중량% 포함하는 공중합체 샘플 3을 이용하여 제조된 점착제 샘플 3-1 내지 3-4에 대해 점착제층의 점착력을 평가하였다.The adhesive strength of the adhesive layer was evaluated for adhesive samples 3-1 to 3-4 prepared using copolymer sample 3 containing 5% by weight of 4-HBA monomer.
도 5는 점착제 샘플 3-1 및 3-2의 UV 조사 전후 박리력(a) 및 샘플 3-3 및 3-4의 UV 조사 전후 박리력(b) 측정 결과를 나타낸 것이며, 도 6은 상기 결과를 토대로 UV 조사 전후의 박리력 변화를 그래프로 나타낸 것이다.Figure 5 shows the results of measuring the peeling force (a) before and after UV irradiation of adhesive samples 3-1 and 3-2 and the peeling force (b) before and after UV irradiation of samples 3-3 and 3-4, and Figure 6 shows the results. Based on this, the change in peeling force before and after UV irradiation is shown graphically.
4-HBA를 이용하여 제조된 공중합체 샘플 3 기반의 점착제의 경우, AOI를 이용한 점착제 3-1 및 3-2에 비해 MOI를 1.65중량부 이용한 점착제 3-3에서 점착력의 변화가 더 확실하게 관찰되었다. 다만, MOI의 함량이 3.3중량부로 증가한 점착제 3-4의 경우에는 초기 점착력이 저하되는 결과를 보였다.In the case of the adhesive based on copolymer sample 3 prepared using 4-HBA, changes in adhesion were more clearly observed in adhesive 3-3 using an MOI of 1.65 parts by weight compared to adhesives 3-1 and 3-2 using AOI. It has been done. However, in the case of adhesive 3-4 where the MOI content was increased to 3.3 parts by weight, the initial adhesive strength decreased.
공중합체 샘플 2 기반의 점착제와 비교하면, 공중합체 샘플 3 기반의 점착제에서 잔사가 크게 감소하는 현상을 보였으며, 이를 통해 4-HBA에 의해 충분한 결사슬이 형성되고 얽힘 효과에 의해 응집력이 강화됨을 확인할 수 있었다. Compared to the adhesive based on copolymer sample 2, the adhesive based on copolymer sample 3 showed a significant decrease in residues, showing that sufficient chains were formed by 4-HBA and cohesion was strengthened by the entanglement effect. I was able to confirm.
공중합체 샘플 3 기반의 점착제에 대한 점착력 측정 결과를 참조하면, 재료의 조성에 따라 곁사슬의 구조 길이가 UV 반응에 전혀 다른 영향을 미치게 되는 결과를 확인할 수 있다. 구체적으로, 분자량이 크고 분자간 결합(intermolecular bonding)이 강하게 형성된 구조에서는 사슬의 길이가 짧아 경화 속도가 빠르고 밀도가 증가하는 반면, 분자량이 낮아서 충분한 응집력(cohesion)을 갖지 못하는 경우에는 곁사슬 길이가 충분히 확보되어 분자간 얽힘 구조가 형성되어야 UV에 대한 반응이 가속되는 것을 확인할 수 있다.Referring to the adhesive strength measurement results for the adhesive based on copolymer sample 3, it can be seen that the length of the side chain structure has a completely different effect on the UV response depending on the composition of the material. Specifically, in a structure with a large molecular weight and strong intermolecular bonding, the chain length is short, so the curing speed is fast and the density increases, whereas in the case where the molecular weight is low and sufficient cohesion is not achieved, the side chain length is sufficiently secured. It can be confirmed that the reaction to UV is accelerated only when an intermolecular entanglement structure is formed.
실험예 4: 공중합체 샘플 4를 이용한 점착제의 UV 경화 전후 점착력 측정Experimental Example 4: Measurement of adhesion before and after UV curing of adhesive using copolymer sample 4
4-HBA 단량체를 10중량% 포함하는 공중합체 샘플 4를 이용하여 제조된 점착제 샘플 4-1 내지 4-4에 대해 점착제층의 점착력을 평가하였다.The adhesive strength of the adhesive layer was evaluated for adhesive samples 4-1 to 4-4 prepared using copolymer sample 4 containing 10% by weight of 4-HBA monomer.
도 7은 점착제 샘플 4-1 및 4-2의 UV 조사 전후 박리력(a) 및 샘플 4-3 및 4-4의 UV 조사 전후 박리력(b) 측정 결과를 나타낸 것이며, 도 8은 상기 결과를 토대로 UV 조사 전후의 박리력 변화를 그래프로 나타낸 것이다.Figure 7 shows the results of measuring the peeling force (a) before and after UV irradiation of adhesive samples 4-1 and 4-2 and the peeling force (b) before and after UV irradiation of samples 4-3 and 4-4, and Figure 8 shows the results. Based on this, the change in peeling force before and after UV irradiation is shown graphically.
공중합체 샘플 4 기반의 점착제의 경우, AOI를 이용한 점착제 샘플 4-1 및 4-2에 비해 MOI를 이용하여 제조된 점착제 샘플 4-3 및 4-4의 점착력 변화가 크게 관찰되었으며, 특히 점착제 샘플 4-3의 경우 UV 경화 전 점착력이 매우 높으면서 UV 경화 후에는 매우 낮은 점착력을 확보할 수 있었다. 또한, 해당 샘플들은 경화 이후 잔사가 전혀 남지 않았으며, 피착면에서 완전히 제거되었다.In the case of the adhesive based on copolymer sample 4, a significant change in adhesion was observed for adhesive samples 4-3 and 4-4 prepared using MOI compared to adhesive samples 4-1 and 4-2 using AOI, especially the adhesive samples In the case of 4-3, very high adhesion before UV curing was achieved, but very low adhesion after UV curing. Additionally, the samples did not leave any residue after curing and were completely removed from the adhered surface.
상기 실험 결과로부터, 샘플 4-3의 경우 공중합체, 메타크릴레이트 구조 및 곁사슬의 길이에 의한 효과가 동시에 발현되어, 외부로 뻗어 나가는 형태의 고분자 곁사슬에 의해 분자내 결합(intramolecular bonding)에 비해 분자간 결합(intermolecular bonding)이 우세하게 나타남을 예측할 수 있었다. 이에 따라, 베이스 자체의 안정성도 높으면서 UV 반응에 의해 더욱 민감하게 변화됨을 확인할 수 있었다.From the above experimental results, in the case of Sample 4-3, the effects of copolymer, methacrylate structure, and side chain length were simultaneously expressed, resulting in intermolecular bonding compared to intramolecular bonding due to the outwardly extending polymer side chain. It was predicted that intermolecular bonding appeared predominantly. Accordingly, it was confirmed that the stability of the base itself was high and that it changed more sensitively due to UV reaction.
이상 본 발명의 일부 구현 형태에 대해서 설명하였으나, 본 발명은 상술한 바와 같은 구현형태에 대해서만 한정되는 것이 아니라 본 발명의 요지를 벗어나지 않는 범위 내에서 수정 및 변형하여 실시할 수 있으며, 그러한 수정 및 변형이 가해진 형태 또한 본 발명의 기술적 사상에 속하는 것으로 이해되어야 한다.Although some implementation forms of the present invention have been described above, the present invention is not limited to the above-described implementation forms, but can be implemented with modifications and variations without departing from the gist of the present invention, and such modifications and variations can be made. This added form should also be understood as belonging to the technical idea of the present invention.
Claims (10)
상기 이소시아네이트 화합물이 상기 아크릴계 공중합체 100중량부에 대하여 0.5 내지 15중량부 포함되는, 광감응성 점착제 제조용 조성물.
An acrylic copolymer prepared by polymerizing a monomer composition containing a (meth)acrylate monomer having an alkyl group, a (meth)acrylate monomer having a hydroxy group, and an unsaturated carboxylic acid monomer; and isocyanate compounds having a carbon-carbon double bond,
A composition for producing a photosensitive adhesive, wherein the isocyanate compound is contained in an amount of 0.5 to 15 parts by weight based on 100 parts by weight of the acrylic copolymer.
상기 히드록시기를 갖는 (메타)아크릴레이트 단량체가 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시부틸(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 8-히드록시옥틸(메타)아크릴레이트, 1,4-시클로헥산디메탄올모노(메타)아크릴레이트, 클로로-2-히드록시프로필아크릴레이트, 디에틸렌글리콜모노(메타)아크릴레이트 및 프로필렌글리콜(메타)아크릴레이트로 구성된 군에서 선택된 1종 이상을 포함하는, 광감응성 점착제 제조용 조성물.
According to claim 1,
The (meth)acrylate monomer having the hydroxy group is 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 1,4-cyclohexanedimethanol mono (meth)acrylate, chloro-2-hydroxypropyl acrylate A composition for producing a photosensitive adhesive, comprising at least one member selected from the group consisting of latex, diethylene glycol mono(meth)acrylate, and propylene glycol (meth)acrylate.
상기 히드록시기를 갖는 (메타)아크릴레이트 단량체가 상기 단량체 조성물 전체 중량에 대하여 3 내지 30중량% 포함되는, 광감응성 점착제 제조용 조성물.
According to claim 1,
A composition for producing a photosensitive adhesive, wherein the (meth)acrylate monomer having the hydroxy group is contained in an amount of 3 to 30% by weight based on the total weight of the monomer composition.
상기 단량체 조성물이 시클로알킬기를 갖는 (메타)아크릴레이트 단량체 또는 방향족 (메타)아크릴레이트 단량체를 더 포함하는, 광감응성 점착제 제조용 조성물.
According to claim 1,
A composition for producing a photosensitive adhesive, wherein the monomer composition further includes a (meth)acrylate monomer or an aromatic (meth)acrylate monomer having a cycloalkyl group.
상기 이소시아네이트 화합물이 (메타)아크릴로일옥시 이소시아네이트, (메타)아크릴로일옥시메틸 이소시아네이트, (메타)아크릴로일옥시에틸 이소시아네이트, (메타)아크릴로일옥시프로필 이소시아네이트 및 (메타)아크릴로일 이소시아네이트로 구성된 군에서 선택된 1종 이상을 포함하는, 광감응성 점착제 제조용 조성물.
According to claim 1,
The isocyanate compounds include (meth)acryloyloxy isocyanate, (meth)acryloyloxymethyl isocyanate, (meth)acryloyloxyethyl isocyanate, (meth)acryloyloxypropyl isocyanate, and (meth)acryloyl isocyanate. A composition for producing a photosensitive adhesive, comprising at least one member selected from the group consisting of.
상기 이소시아네이트 화합물이 상기 히드록시기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대해 20 내지 80중량부 포함되는, 광감응성 점착제 제조용 조성물.
According to claim 1,
A composition for producing a photosensitive adhesive, wherein the isocyanate compound is contained in an amount of 20 to 80 parts by weight based on 100 parts by weight of the (meth)acrylate monomer having the hydroxy group.
A photosensitive adhesive comprising a binder resin prepared by reacting the composition for producing the photosensitive adhesive of any one of claims 1 to 6, and a photoinitiator.
상기 광개시제가 바인더 수지 100중량부에 대하여 0.1 내지 10중량부 포함되는, 광감응성 점착제.
According to claim 7,
A photosensitive adhesive containing 0.1 to 10 parts by weight of the photoinitiator based on 100 parts by weight of the binder resin.
상기 점착제가 2 내지 12관능의 (메타)아크릴레이트 화합물을 1종 이상 포함하는 UV 경화성 올리고머를 더 포함하는, 광감응성 점착제.
According to claim 7,
A photosensitive adhesive, wherein the adhesive further includes a UV-curable oligomer containing one or more 2- to 12-functional (meth)acrylate compounds.
상기 기재 상에 형성되며, 제 7 항의 광감응성 점착제를 포함하는 점착제층
을 포함하는, 점착필름.substrate, and
An adhesive layer formed on the substrate and comprising the photosensitive adhesive of claim 7.
Including, adhesive film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220072817A KR20230172230A (en) | 2022-06-15 | 2022-06-15 | Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220072817A KR20230172230A (en) | 2022-06-15 | 2022-06-15 | Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20230172230A true KR20230172230A (en) | 2023-12-22 |
Family
ID=89309649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020220072817A KR20230172230A (en) | 2022-06-15 | 2022-06-15 | Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20230172230A (en) |
-
2022
- 2022-06-15 KR KR1020220072817A patent/KR20230172230A/en not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102399857B1 (en) | Reinforcing film | |
| US9761476B2 (en) | Dicing film and dicing die-bonding film | |
| KR100922684B1 (en) | Photocuring Composition for Adhesive Layer and Dicing Die Bonding Film Comprising the Same | |
| US8722184B2 (en) | Wafer-adhering adhesive tape | |
| JP4954572B2 (en) | Protective sheet for semiconductor wafer processing, and semiconductor wafer processing method using the same | |
| JP5491049B2 (en) | Substrate-less pressure-sensitive adhesive sheet for semiconductor wafer protection, semiconductor wafer back surface grinding method using the pressure-sensitive adhesive sheet, and method for producing the pressure-sensitive adhesive sheet | |
| WO2018066408A1 (en) | Adhesive tape for semiconductor processing, and semiconductor device manufacturing method | |
| JP2001203255A (en) | Semiconductor wafer holding/protecting adhesive sheet | |
| KR100716327B1 (en) | Re-release type adhesive and re-release type adhesive sheet | |
| JP5089358B2 (en) | Wafer processing tape | |
| WO2017149981A1 (en) | Adhesive composition and adhesive sheet | |
| KR20200049698A (en) | Reinforcing film | |
| JP5010800B2 (en) | Manufacturing method of semiconductor device and adhesive tape for dicing | |
| TW202137306A (en) | Protection sheet for semiconductor processing and manufacturing method of semiconductor device can suppress the generation of cracks in the wafer after polishing | |
| JP7381448B2 (en) | Adhesive tape and semiconductor device manufacturing method | |
| TWI721364B (en) | Back grinding tape | |
| KR20230172230A (en) | Composition for Preparing Photosensitive Adhesive, Photosensitive Adhesive Prepared Using Same and Adhesive Film Comprising the Adhesive | |
| JP5291040B2 (en) | Adhesive tape for wafer processing | |
| KR20180113199A (en) | Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and process for producing the same | |
| US11404301B2 (en) | Dicing die-bonding film | |
| TWI822670B (en) | Base material for back grinding tape | |
| JP2004122758A (en) | Multi-layer sheet, its manufacturing method and adhesive sheet using multi-layer sheet | |
| JP7008817B2 (en) | Back grinding tape | |
| KR20200024591A (en) | Back grinding tape | |
| JP2013199580A (en) | Pressure-sensitive adhesive tape for sticking wafer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E902 | Notification of reason for refusal |