KR102627771B1 - Silane-based adhesion promoter and adhesion composition comprising the same - Google Patents
Silane-based adhesion promoter and adhesion composition comprising the same Download PDFInfo
- Publication number
- KR102627771B1 KR102627771B1 KR1020200177572A KR20200177572A KR102627771B1 KR 102627771 B1 KR102627771 B1 KR 102627771B1 KR 1020200177572 A KR1020200177572 A KR 1020200177572A KR 20200177572 A KR20200177572 A KR 20200177572A KR 102627771 B1 KR102627771 B1 KR 102627771B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- adhesive composition
- silane
- adhesion promoter
- present
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 29
- 239000002318 adhesion promoter Substances 0.000 title claims abstract description 27
- 239000000853 adhesive Substances 0.000 claims abstract description 64
- 230000001070 adhesive effect Effects 0.000 claims abstract description 64
- 229910021645 metal ion Inorganic materials 0.000 claims description 17
- 125000001033 ether group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 239000003002 pH adjusting agent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000006174 pH buffer Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 33
- 239000002184 metal Substances 0.000 abstract description 33
- 239000011888 foil Substances 0.000 abstract description 30
- 239000000758 substrate Substances 0.000 abstract description 28
- 239000002952 polymeric resin Substances 0.000 abstract description 24
- 229920003002 synthetic resin Polymers 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000005241 heteroarylamino group Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- AZUXKVXMJOIAOF-UHFFFAOYSA-N 1-(2-hydroxypropoxy)propan-2-ol Chemical group CC(O)COCC(C)O AZUXKVXMJOIAOF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000006179 pH buffering agent Substances 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- -1 siloxane structure Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000003746 surface roughness Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical group NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical group CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical group NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- VMKYLARTXWTBPI-UHFFFAOYSA-N copper;dinitrate;hydrate Chemical compound O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O VMKYLARTXWTBPI-UHFFFAOYSA-N 0.000 description 1
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- VWYGTDAUKWEPCZ-UHFFFAOYSA-L dichlorocopper;hydrate Chemical compound O.Cl[Cu]Cl VWYGTDAUKWEPCZ-UHFFFAOYSA-L 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- XBDUTCVQJHJTQZ-UHFFFAOYSA-L iron(2+) sulfate monohydrate Chemical compound O.[Fe+2].[O-]S([O-])(=O)=O XBDUTCVQJHJTQZ-UHFFFAOYSA-L 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
본 발명은 특정 구조를 포함하는 실란계 접착 촉진제 화합물과 이를 포함하는 접착제 조성물에 관한 것이다. 이러한 본 발명에 따른 접착제 조성물은 고분자 수지 기재와 금속박의 결합(접착)에 유용하게 사용될 수 있다.The present invention relates to a silane-based adhesion promoter compound containing a specific structure and an adhesive composition containing the same. The adhesive composition according to the present invention can be usefully used for bonding (adhering) a polymer resin substrate and a metal foil.
Description
본 발명은 서로 상이한 성분으로 이루어진 소재의 접착(결합)을 촉진 및 증진시킬 수 있는 실란계 접착 촉진제 및 이를 포함하는 접착제 조성물에 관한 것이다.The present invention relates to a silane-based adhesion promoter that can promote and enhance the adhesion (bonding) of materials composed of different components and an adhesive composition containing the same.
휴대폰, PDA 등의 이동통신기기, LCD, OLED, QLED 등의 평판디스플레이, 기타 전자소자 등에는 금속배선이 형성된 회로기판이 폭넓게 적용되고 있다. 상기 회로기판은 통상적으로 절연 및 베이스 기재 역할을 하는 고분자 수지 기재와 금속박을 결합시킨 후, 에칭 공정을 통해 금속박에 배선회로를 형성하는 과정으로 제조된다.Circuit boards with metal wiring are widely used in mobile communication devices such as mobile phones and PDAs, flat panel displays such as LCD, OLED, and QLED, and other electronic devices. The circuit board is typically manufactured by combining metal foil with a polymer resin substrate that serves as an insulator and base material, and then forming a wiring circuit on the metal foil through an etching process.
상기 금속박과 고분자 수지 기재 간의 결합(접착)은 일반적으로 조도의 차이에 의한 물리적 결합에 의존해 왔다. 가장 널리 알려진 흑색 산화 공정이 그 예이다. 구체적으로 금속박 표면을 산화시켜 표면에 바늘 모양의 미세한 산화막을 형성하는 것으로, 형성된 산화막은 고분자 수지 기재와의 결합력(접착력)을 향상시켜 금속박과 고분자 수지 기재가 떨어지지 않게 한다. 그러나 이러한 공정은 회로의 미세화, 기판의 소형화가 진행되면서 한계를 드러내고 있다. 즉, 회로가 미세화되면서 산화막에 의한 전송 손실 및 전송 속도가 감소하는 문제가 나타나고 있는 것이다. 이를 해결하기 위해 금속박과 고분자 수지 기재를 에폭시계 접착제, 아크릴계 접착제, 실리콘계 접착제 등으로 접착하는 공정이 제안된 바 있다.The bond (adhesion) between the metal foil and the polymer resin substrate has generally relied on physical bonding due to differences in roughness. The most widely known example is the black oxidation process. Specifically, the surface of the metal foil is oxidized to form a fine needle-shaped oxide film on the surface. The formed oxide film improves the bonding strength (adhesion) with the polymer resin substrate and prevents the metal foil and the polymer resin substrate from separating. However, this process is showing its limitations as circuits become more refined and boards become smaller. In other words, as circuits become more refined, problems such as transmission loss due to the oxide film and transmission speed decrease are emerging. To solve this problem, a process for adhering metal foil and polymer resin substrate using epoxy adhesives, acrylic adhesives, silicone adhesives, etc. has been proposed.
상기 접착제의 구체적인 일례로, 대한민국공개특허공보 제2015-0025319호에는 에폭시 수지 조성물을 이용한 접착시트 및 이를 이용하여 제조된 회로기판에 관한 기술이 개시된 바 있다. 그러나 상기 기술은 에폭시 수지 조성물로 제조된 접착시트를 이용하여 베이스 기판과 금속박막을 결합시키기 때문에 베이스 기판과 금속박막 간에 높은 결합력(접착력)을 나타내는데 한계가 있다.As a specific example of the adhesive, Korea Patent Publication No. 2015-0025319 discloses technology related to an adhesive sheet using an epoxy resin composition and a circuit board manufactured using the same. However, since the above technology bonds the base substrate and the metal thin film using an adhesive sheet made of an epoxy resin composition, there is a limitation in showing high bonding strength (adhesion) between the base substrate and the metal thin film.
따라서 고분자 수지 기재와 금속박 간의 결합력을 높일 수 있는 접착제에 관한 기술이 요구되고 있는 실정이다.Therefore, there is a demand for adhesive technology that can increase the bonding strength between the polymer resin substrate and the metal foil.
본 발명은 고분자 수지 기재와 금속박 간의 결합(접착)을 촉진 및 증진시킬 수 있는 실란계 접착 촉진제를 제공하고자 한다.The present invention seeks to provide a silane-based adhesion promoter that can promote and enhance bonding (adhesion) between a polymer resin substrate and metal foil.
또한 본 발명은 상기 실란계 접착 촉진제를 포함하는 접착제 조성물을 제공하고자 한다.Additionally, the present invention seeks to provide an adhesive composition containing the silane-based adhesion promoter.
상기 과제를 해결하기 위해 본 발명은, 하기 화학식 1 또는 화학식 2로 표시되는 구조를 포함하는 실란계 접착 촉진제를 제공한다.In order to solve the above problems, the present invention provides a silane-based adhesion promoter comprising a structure represented by the following Chemical Formula 1 or Chemical Formula 2.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 및 화학식 2에서,In Formula 1 and Formula 2,
R1은 수소 및 C1 내지 C10의 알킬기로 이루어진 군에서 선택되고, 이때, 복수의 R1은 서로 동일하거나 상이하고,R 1 is selected from the group consisting of hydrogen and an alkyl group of C 1 to C 10 , wherein the plurality of R 1 is the same or different from each other,
R2는 C1 내지 C10의 알킬기, C1 내지 C10의 알콕시기, C6 내지 C20의 아릴기 및 C2 내지 C20의 헤테로아릴기로 이루어진 군에서 선택되고,R 2 is selected from the group consisting of a C 1 to C 10 alkyl group, a C 1 to C 10 alkoxy group, a C 6 to C 20 aryl group, and a C 2 to C 20 heteroaryl group,
A는 C1 내지 C10의 알킬렌기, C1 내지 C10의 하이드록시알킬에테르기, 에테르기, 아민기, 하이드록시아민기, 에스테르기 및 티오에테르기로 이루어진 군에서 선택되고,A is selected from the group consisting of C 1 to C 10 alkylene group, C 1 to C 10 hydroxyalkyl ether group, ether group, amine group, hydroxyamine group, ester group and thioether group,
L은 C1 내지 C10의 알킬렌기, C1 내지 C10의 알킬아민기, C1 내지 C10의 하이드록시알킬에테르기 및 C2 내지 C20의 헤테로아릴아미노기로 이루어진 군에서 선택되고,L is selected from the group consisting of a C 1 to C 10 alkylene group, a C 1 to C 10 alkylamine group, a C 1 to C 10 hydroxyalkyl ether group, and a C 2 to C 20 heteroarylamino group,
상기 R1, R2, A 및 L는 각각 독립적으로, 아미노기, C1 내지 C10의 알킬기, C1 내지 C10의 알킬렌아민기, C6 내지 C20의 아릴기 및 C2 내지 C20의 헤테로아릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환 또는 비치환된다.R 1 , R 2 , A and L are each independently an amino group, a C 1 to C 10 alkyl group, a C 1 to C 10 alkyleneamine group, a C 6 to C 20 aryl group, and a C 2 to C 20 It is substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups.
또한 본 발명은 상기 실란계 접착 촉진제; 금속 이온 공급원; 및 pH 조절제를 포함하는 접착제 조성물을 제공한다.In addition, the present invention provides the silane-based adhesion promoter; metal ion source; and a pH adjuster.
본 발명은 실란계 접착 촉진제를 포함하는 접착제 조성물을 금속박에 도포하여, 금속박 표면이 고분자 수지 기재와 강한 접착(결합)이 이루어질 수 있도록 하는 전처리(활성화) 과정을 거쳐 고분자 수지 기재와 금속박을 결합(접착)시키기 때문에, 고분자 수지 기재와 금속박 간에 높은 결합력(접착력)을 나타내는 회로기판을 제공할 수 있다.In the present invention, an adhesive composition containing a silane-based adhesion promoter is applied to a metal foil, and the polymer resin substrate and the metal foil are bonded ( Because of the adhesion, it is possible to provide a circuit board that exhibits high bonding strength (adhesion) between the polymer resin substrate and the metal foil.
도 1은 본 발명의 일 실시예에 따른 접착제 조성물에 포함되는 실란계 접착 촉진제의 작용기작을 도시한 것이다.
도 2는 본 발명의 일 실시예에 따른 접착제 조성물에 포함되는 실란계 접착 촉진제와 금속 이온 공급원 간의 작용기작을 도시한 것이다.
도 3은 본 발명의 실험예 1에 따른 결과를 도시한 것이다.Figure 1 shows the mechanism of action of a silane-based adhesion promoter included in an adhesive composition according to an embodiment of the present invention.
Figure 2 shows the mechanism of action between a silane-based adhesion promoter and a metal ion source included in an adhesive composition according to an embodiment of the present invention.
Figure 3 shows the results according to Experimental Example 1 of the present invention.
본 발명의 설명 및 청구범위에서 사용된 용어나 단어는, 통상적이거나 사전적인 의미로 한정해서 해석되어서는 아니되며, 발명자는 그 자신의 발명을 가장 최선의 방법으로 설명하기 위해 용어의 개념을 적절하게 정의할 수 있다는 원칙에 입각하여, 본 발명의 기술적 사상에 부합하는 의미와 개념으로 해석되어야만 한다.Terms or words used in the description and claims of the present invention should not be construed as limited to their usual or dictionary meanings, and the inventor should appropriately use the concepts of terms to explain his invention in the best way. Based on the principle of definability, it must be interpreted with meaning and concept consistent with the technical idea of the present invention.
본 발명은 고분자 수지 기재와 금속박 사이에서 가교 역할을 하여 고분자 수지 기재와 금속박 간의 높은 접착력(결합력)을 나타낼 수 있도록 하는 실란계 접착 촉진제 및 이를 포함하는 접착제 조성물에 관한 것으로, 이에 대해 구체적으로 설명하면 다음과 같다.The present invention relates to a silane-based adhesion promoter that acts as a bridge between a polymer resin substrate and a metal foil to exhibit high adhesion (bonding strength) between the polymer resin substrate and the metal foil, and an adhesive composition containing the same. This will be described in detail. As follows.
본 발명에 따른 실란계 접착 촉진제는 하기 화학식 1 또는 화학식 2로 표시되는 구조를 포함한다. 구체적으로 실란계 접착 촉진제를 하기 화학식 1 또는 화학식 2로 표시되는 구조를 분자 내에 포함하는 화합물이거나, 화학식 1 또는 화학식 2로 표시되는 화합물일 수 있다.The silane-based adhesion promoter according to the present invention includes a structure represented by the following formula (1) or formula (2). Specifically, the silane-based adhesion promoter may be a compound containing a structure represented by the following Formula 1 or Formula 2 in the molecule, or it may be a compound represented by Formula 1 or Formula 2.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 및 화학식 2에서,In Formula 1 and Formula 2,
R1은 수소 및 C1 내지 C10의 알킬기로 이루어진 군에서 선택되고, 이때, 복수의 R1은 서로 동일하거나 상이하고,R 1 is selected from the group consisting of hydrogen and an alkyl group of C 1 to C 10 , wherein the plurality of R 1 is the same or different from each other,
R2는 C1 내지 C10의 알킬기, C1 내지 C10의 알콕시기, C6 내지 C20의 아릴기 및 C2 내지 C20의 헤테로아릴기로 이루어진 군에서 선택되고,R 2 is selected from the group consisting of a C 1 to C 10 alkyl group, a C 1 to C 10 alkoxy group, a C 6 to C 20 aryl group, and a C 2 to C 20 heteroaryl group,
A는 C1 내지 C10의 알킬렌기, C1 내지 C10의 하이드록시알킬에테르기, 에테르기(-O-), 아민기(-NH-), 하이드록시아민기(), 에스테르기(-COO-) 및 티오에테르기(-S-)로 이루어진 군에서 선택되고,A is a C 1 to C 10 alkylene group, a C 1 to C 10 hydroxyalkyl ether group, an ether group (-O-), an amine group (-NH-), a hydroxyamine group ( ), ester group (-COO-), and thioether group (-S-),
L은 C1 내지 C10의 알킬렌기, C1 내지 C10의 알킬아민기, C1 내지 C10의 하이드록시알킬에테르기 및 C2 내지 C20의 헤테로아릴아미노기로 이루어진 군에서 선택된다.L is selected from the group consisting of a C 1 to C 10 alkylene group, a C 1 to C 10 alkylamine group, a C 1 to C 10 hydroxyalkyl ether group, and a C 2 to C 20 heteroarylamino group.
구체적으로 상기 R1의 알킬기는 선형, 가지형, 또는 분지형 구조의 알킬기로, 그 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기 등을 들 수 있다. 이러한 R1은 고분자 수지 기재에 결합되는 작용기로, 고분자 수지 기재에 본 발명에 따른 실란계 접착 촉진제가 잘 결합될 수 있도록 바람직하게는 메틸기, 에틸기 또는 프로필기일 수 있고, 더 바람직하게는 에틸기일 수 있다.Specifically, the alkyl group of R 1 is an alkyl group with a linear, branched, or branched structure, such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, etc. can be mentioned. This R 1 is a functional group bonded to the polymer resin substrate, and may preferably be a methyl group, an ethyl group, or a propyl group, and more preferably an ethyl group so that the silane-based adhesion promoter according to the present invention can be well bonded to the polymer resin substrate. there is.
상기 R2의 알킬기는 선형, 가지형, 또는 분지형 구조의 알킬기로, 그 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기 등을 들 수 있다. 또한 R2의 알콕시기의 예로는 메톡시기, 에톡시기, 프로폭시기, 부톡시기, 펜틸옥시기, 헥실옥시기 등을 들 수 있다. 또 R2의 아릴기의 예로는 페닐기, 바이페닐기, 나프틸기, 안트릴기, 페난트릴기 등을 들 수 있다. 또한 R2의 헤테로아릴기는 1종 이상의 헤테로원자(예를 들어, N, O, S, F)를 포함하는 1가 방향족 고리기로, 그 예로는 이미다졸기, 티아졸기, 트리아졸기, 피리딘기, 멜라민기 등을 들 수 있다. 이러한 R2는 금속박의 결합에 영향을 미치는 작용기로, 금속박에 본 발명에 따른 실란계 접착 촉진제가 잘 결합될 수 있도록 바람직하게는 이미다졸기, 티아졸기, 트리아졸기, 피리딘기, 또는 멜라민기일 수 있고, 더 바람직하게는 이미다졸기일 수 있다.The alkyl group of R 2 is an alkyl group with a linear, branched, or branched structure, examples of which include methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, etc. You can. Additionally, examples of the alkoxy group of R 2 include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, and hexyloxy group. Also, examples of the aryl group of R 2 include phenyl group, biphenyl group, naphthyl group, anthryl group, and phenanthryl group. In addition, the heteroaryl group of R 2 is a monovalent aromatic ring group containing one or more heteroatoms (for example, N, O, S, F), examples of which include imidazole group, thiazole group, triazole group, pyridine group, Melamine groups, etc. can be mentioned. This R 2 is a functional group that affects the bonding of the metal foil, and is preferably an imidazole group, a thiazole group, a triazole group, a pyridine group, or a melamine group so that the silane-based adhesion promoter according to the present invention can be well bonded to the metal foil. and, more preferably, it may be an imidazole group.
상기 A의 알킬렌기의 예로는 메틸렌기, 에틸렌기, 프로필렌기, 부틸렌기 등을 들 수 있다. 또한 A의 하이드록시알킬에테르기의 예로는 하이드록시메틸에테르기, 하이드록시에틸에테르기, 2-하이드록시프로필에테르기 등을 들 수 있다. 이러한 A는 실란계 접착 촉진제의 실록산(Si-0) 구조측과 아민 구조측 간에 강한 결합이 유지될 수 있도록 바람직하게는 에테르기(-O-), 아민기(-NH-), 하이드록시에테르기, 하이드록시아민기, 에스테르기(-COO-), 또는 티오에테르기(-S-)일 수 있고, 더 바람직하게는 2-하이드록시프로필에테르기()일 수 있다.Examples of the alkylene group of A include methylene group, ethylene group, propylene group, butylene group, etc. Additionally, examples of the hydroxyalkyl ether group of A include hydroxymethyl ether group, hydroxyethyl ether group, and 2-hydroxypropyl ether group. This A is preferably an ether group (-O-), amine group (-NH-), or hydroxyether so that a strong bond can be maintained between the siloxane (Si-0) structural side and the amine structural side of the silane-based adhesion promoter. group, hydroxyamine group, ester group (-COO-), or thioether group (-S-), more preferably 2-hydroxypropyl ether group ( ) can be.
상기 L의 알킬렌기의 예로는 메틸렌기, 에틸렌기, 프로필렌기, 부틸렌기 등을 들 수 있다. 또 L의 알킬아민기의 예로는 메틸아민기, 에틸아민기, 프로필아민기, 이소프로필아민기, 부틸아민기, 펜틸아민기, 헥실아민기 등을 들 수 있다. 또 L의 하이드록시알킬에테르기의 예로는 하이드록시메틸에테르기, 하이드록시에틸에테르기, 2-하이드록시프로필에테르기 등을 들 수 있다. 상기 L의 헤테로아릴아미노기는 1종 이상의 헤테로원자(예를 들어, N, O, S, F)를 포함하는 방향족 고리기와 아미노기를 포함하는 작용기로, 그 예로는 아미노이미다졸기, 아미노티아졸기 등을 들 수 있다.Examples of the alkylene group of L include methylene group, ethylene group, propylene group, butylene group, etc. Examples of the alkylamine group of L include methylamine group, ethylamine group, propylamine group, isopropylamine group, butylamine group, pentylamine group, and hexylamine group. Additionally, examples of the hydroxyalkyl ether group of L include hydroxymethyl ether group, hydroxyethyl ether group, and 2-hydroxypropyl ether group. The heteroarylamino group of L is a functional group containing an aromatic ring group containing one or more heteroatoms (e.g., N, O, S, F) and an amino group, such as aminoimidazole group, aminothiazole group, etc. can be mentioned.
여기서 상기 R1의 알킬기; R2의 알킬기, 알콕시기, 아릴기, 헤테로아릴기; A의 알킬렌기, 하이드록시알킬에테르기, 아민기, 히드록시아민기; 및 L의 알킬렌기, 알킬아민기, 하이드록시알킬에테르기, 헤테로아릴아미노기(각 작용기에 결합된 수소)는 각각 독립적으로, 아미노기, C1 내지 C10의 알킬기, C1 내지 C10의 알킬렌아민기, C6 내지 C20의 아릴기 및 C2 내지 C20의 헤테로아릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환 또는 비치환될 수 있다.Here, the alkyl group of R 1 ; R 2 alkyl group, alkoxy group, aryl group, heteroaryl group; A alkylene group, hydroxyalkyl ether group, amine group, hydroxyamine group; And the alkylene group, alkylamine group, hydroxyalkyl ether group, and heteroarylamino group (hydrogen bonded to each functional group) of L are each independently an amino group, a C 1 to C 10 alkyl group, and a C 1 to C 10 alkylene group. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group, a C 6 to C 20 aryl group, and a C 2 to C 20 heteroaryl group.
이러한 본 발명에 따른 실란계 접착 촉진제는 고분자 수지 기재에 결합하는 실록산 구조측과, 금속박의 결합에 작용하는 아민 구조측을 포함함에 따라 서로 상이한 성분으로 이루어진 고분자 수지 기재와 금속박을 견고하게 접착시킬 수 있는데, 이에 대한 구체적인 설명은 후술하기로 한다.The silane-based adhesion promoter according to the present invention includes a siloxane structure side that binds to the polymer resin substrate and an amine structure side that acts on the bonding of the metal foil, so it can firmly adhere a polymer resin substrate made of different components and a metal foil. A detailed explanation of this will be provided later.
본 발명에 따른 접착제 조성물은 상술한 실란계 접착 촉진제를 포함한다. 구체적으로 본 발명에 따른 접착제 조성물은 상술한 실란계 접착 촉진제, 금속 이온 공급원 및 pH 조절제를 포함한다. The adhesive composition according to the present invention includes the silane-based adhesion promoter described above. Specifically, the adhesive composition according to the present invention includes the above-described silane-based adhesion promoter, metal ion source, and pH adjuster.
본 발명에 따른 접착제 조성물에 포함되는 실란계 접착 촉진제는 고분자 수지 기재와 금속박 간의 접착(결합)을 촉진 및 증진시키는 역할을 한다. 구체적으로 실란계 접착 촉진제는 고분자 수지 기재와 금속박 사이에서 가교 역할을 하는 것으로, 그 작용기작(mechanism)의 일례를 도 1과 같이 나타낼 수 있다. 구체적으로 도 1을 참조하면, 실란계 접착 촉진제의 실록산 구조측이 고분자 수지 기재에 결합하고 실란계 접착 촉진제의 아민 구조측이 금속박의 표면에 배열된 금속 이온과 결합하는 작용기작으로 인해 고분자 수지 기재와 금속박이 높은 접착력을 나타내도록 결합될 수 있다.The silane-based adhesion promoter included in the adhesive composition according to the present invention serves to promote and enhance adhesion (bonding) between the polymer resin substrate and the metal foil. Specifically, the silane-based adhesion promoter acts as a bridge between the polymer resin substrate and the metal foil, and an example of its mechanism can be shown in Figure 1. Specifically, referring to Figure 1, the siloxane structure side of the silane-based adhesion promoter binds to the polymer resin substrate and the amine structure side of the silane-based adhesion promoter binds to the metal ions arranged on the surface of the metal foil, resulting in the polymer resin substrate. and metal foil can be combined to exhibit high adhesion.
이러한 실란계 접착 촉진제의 함량은 접착제 조성물의 접착성 및 기능성 등을 고려할 때, 접착제 조성물 총 중량%를 기준으로, 0.1 내지 30 중량%, 바람직하게는 1 내지 10 중량%일 수 있다.Considering the adhesion and functionality of the adhesive composition, the content of the silane-based adhesion promoter may be 0.1 to 30% by weight, preferably 1 to 10% by weight, based on the total weight% of the adhesive composition.
본 발명에 따른 접착제 조성물에 포함되는 금속 이온 공급원은 고분자 수지 기재와 금속박의 결합을 위해 금속박 표면에 금속 이온을 공급하는 역할을 한다. 상기 금속 이온 공급원은 금속박에 대응되는 금속 이온을 공급하는 것이라면 특별히 한정되지 않으며, 그 예로는 염화구리, 염화구리 수화물, 황산구리, 황산구리 수화물, 질산구리, 질산구리 수화물 등을 들 수 있다.The metal ion source included in the adhesive composition according to the present invention serves to supply metal ions to the surface of the metal foil for bonding the polymer resin substrate and the metal foil. The metal ion source is not particularly limited as long as it supplies metal ions corresponding to the metal foil, and examples include copper chloride, copper chloride hydrate, copper sulfate, copper sulfate hydrate, copper nitrate, and copper nitrate hydrate.
이러한 금속 이온 공급원의 함량은 접착제 조성물의 접착성 및 기능성 등을 고려할 때, 접착제 조성물 총 중량%를 기준으로, 0.01 내지 10 중량%, 바람직하게는 0.1 내지 0.5 중량%일 수 있다.Considering the adhesiveness and functionality of the adhesive composition, the content of the metal ion source may be 0.01 to 10% by weight, preferably 0.1 to 0.5% by weight, based on the total weight% of the adhesive composition.
본 발명에 따른 접착제 조성물에 포함되는 pH 조절제는 접착제 조성물의 pH를 조절하는 역할을 한다. 상기 pH 조절제는 특별히 한정되지 않으나, 포름산, 아세트산, 프로피온산, 부틸산, 옥탄산, 말론산, 프탈산, 락트산, 글루탐산, 타르타르산, 푸마르산, 시트르산, 글리콘산 또는 숙신산 등을 들 수 있다.The pH adjuster included in the adhesive composition according to the present invention serves to adjust the pH of the adhesive composition. The pH adjuster is not particularly limited, but includes formic acid, acetic acid, propionic acid, butyric acid, octanoic acid, malonic acid, phthalic acid, lactic acid, glutamic acid, tartaric acid, fumaric acid, citric acid, glycolic acid, or succinic acid.
이러한 pH 조절제의 함량은 접착제 조성물의 pH에 따라 적절히 조절될 수 있다.The content of this pH adjuster can be appropriately adjusted depending on the pH of the adhesive composition.
한편 본 발명에 따른 접착제 조성물은 접착제 조성물의 접착성, 기능성 등을 높이기 위해 이온안정제, pH 완충제 및 접착 보조제로 이루어진 군에서 선택되는 1종 이상의 첨가제와 용매를 더 포함할 수 있다.Meanwhile, the adhesive composition according to the present invention may further include one or more additives and solvents selected from the group consisting of ion stabilizers, pH buffers, and adhesive aids in order to increase the adhesiveness and functionality of the adhesive composition.
본 발명에 따른 접착제 조성물에 더 포함되는 이온안정제는 금속 이온 공급원으로부터 유래되는 금속 이온을 안정화시키는 역할을 한다. 상기 이온안정제는 특별히 한정되지 않으며, 그 예로는 에틸렌디아민테트라아세트산디나트륨(EDTA-2Na) 수용액 등을 들 수 있다.The ion stabilizer further included in the adhesive composition according to the present invention serves to stabilize metal ions derived from a metal ion source. The ion stabilizer is not particularly limited, and examples include an aqueous solution of disodium ethylenediaminetetraacetate (EDTA-2Na).
이러한 이온안정제의 함량은 접착제 조성물의 접착성 및 기능성 등을 고려할 때, 접착제 조성물 총 중량%를 기준으로, 0.1 내지 10 중량%, 바람직하게는 1 내지 5 중량%일 수 있다.Considering the adhesiveness and functionality of the adhesive composition, the content of the ion stabilizer may be 0.1 to 10% by weight, preferably 1 to 5% by weight, based on the total weight% of the adhesive composition.
본 발명에 따른 접착제 조성물에 더 포함되는 pH 완충제는 접착제 조성물의 pH를 요구되는 범위 내로 유지시키는 역할을 한다. 상기 pH 완충제는 특별히 한정되지 않으며, 그 예로는 포름산 암모늄, 인산 칼륨, 시트르산 칼륨, 아세트산 칼륨 등을 들 수 있다.The pH buffering agent further included in the adhesive composition according to the present invention serves to maintain the pH of the adhesive composition within a required range. The pH buffering agent is not particularly limited, and examples include ammonium formate, potassium phosphate, potassium citrate, and potassium acetate.
이러한 pH 완충제의 함량은 접착제 조성물의 pH에 따라 적절히 조절될 수 있다.The content of this pH buffering agent can be appropriately adjusted depending on the pH of the adhesive composition.
본 발명에 따른 접착제 조성물에 더 포함되는 접착 보조제는 조성물 내에 환원된 금속 이온을 공급하는 역할을 한다. 상기 공급된 금속 이온에 의해 금속박과 접착제 조성물 간의 가교 반응을 높일 수 있다. 상기 접착 보조제는 특별히 한정되지 않으며, 그 예로는 염화제이철 수화물, 황산철 수화물, 질산제이철 수화물 등을 들 수 있다.The adhesion aid further included in the adhesive composition according to the present invention serves to supply reduced metal ions in the composition. The crosslinking reaction between the metal foil and the adhesive composition can be increased by the supplied metal ions. The adhesion aid is not particularly limited, and examples thereof include ferric chloride hydrate, iron sulfate hydrate, and ferric nitrate hydrate.
이러한 접착 보조제의 함량은 접착제 조성물의 접착성 및 기능성 등을 고려할 때, 접착제 조성물 총 중량%를 기준으로, 0.1 내지 15 중량%, 바람직하게는 0.3 내지 0.5 중량%일 수 있다.Considering the adhesion and functionality of the adhesive composition, the content of the adhesive aid may be 0.1 to 15% by weight, preferably 0.3 to 0.5% by weight, based on the total weight% of the adhesive composition.
본 발명에 따른 접착제 조성물에 더 포함되는 용매는 접착제 조성물의 점도 및 분산성을 제어하는 역할을 한다. 상기 용매는 특별히 한정되지 않으며, 증류수, 탈이온수, 알코올계 용매, 케톤계 용매, 에테르계 용매 등을 들 수 있다.The solvent further included in the adhesive composition according to the present invention serves to control the viscosity and dispersibility of the adhesive composition. The solvent is not particularly limited and includes distilled water, deionized water, alcohol-based solvents, ketone-based solvents, and ether-based solvents.
이러한 용매의 함량은 접착제 조성물의 접착성 및 기능성 등을 고려할 때, 접착제 조성물 총 중량%를 기준으로, 용매 이외의 각 성분들의 함량을 제외한 잔량일 수 있다.Considering the adhesiveness and functionality of the adhesive composition, the content of the solvent may be the remaining amount excluding the contents of each component other than the solvent, based on the total weight% of the adhesive composition.
한편 본 발명에 따른 접착제 조성물은 통상적으로 공지된 첨가제를 더 포함할 수 있다.Meanwhile, the adhesive composition according to the present invention may further include commonly known additives.
이와 같은 본 발명에 따른 접착제 조성물의 pH는 1 내지 6일 수 있다. 상기 접착제 조성물의 pH가 상기 범위를 나타냄에 따라 금속 이온을 안정화시킬 수 있고, 접착제 조성물의 제거가 용이할 수 있다.The pH of the adhesive composition according to the present invention may be 1 to 6. As the pH of the adhesive composition is within the above range, metal ions can be stabilized and the adhesive composition can be easily removed.
본 발명에 따른 접착제 조성물은 상술한 실란계 접착 촉진제를 포함함에 따라 고분자 수지 기재와 금속박 간의 결합력(접착력)을 높일 수 있으며, 고온의 환경에 노출되더라도 내열성, 내구성 등을 확보할 수 있다. 또한 접착제 조성물로 형성된 접착제층의 두께 제어가 자유로우며, 접착제층의 제거가 필요할 경우, 용이하게 제거할 수 있다.The adhesive composition according to the present invention can increase the bonding strength (adhesion) between the polymer resin substrate and the metal foil by containing the above-described silane-based adhesion promoter, and can secure heat resistance and durability even when exposed to a high temperature environment. In addition, the thickness of the adhesive layer formed from the adhesive composition can be freely controlled, and when removal of the adhesive layer is necessary, it can be easily removed.
본 발명에 따른 접착제 조성물로 고분자 수지 기재와 금속박을 접착시키는 방법은 다음과 같은 과정으로 이루어질 수 있다. 구체적으로 금속박을 탈지-수세-산세-수세하는 과정을 거친 후, 금속박에 접착제 조성물을 도포(30℃±5℃, 30초-10분)하고 건조시킨 후, 고분자 수지 기재와 프레스하여 접착시킬 수 있다.The method of bonding a polymer resin substrate and a metal foil with the adhesive composition according to the present invention may be accomplished by the following process. Specifically, after going through the process of degreasing, washing, pickling, and washing the metal foil, the adhesive composition can be applied to the metal foil (30℃±5℃, 30 seconds-10 minutes), dried, and then pressed and bonded to the polymer resin substrate. there is.
이하, 실시예에 의하여 본 발명을 더욱 상세하게 설명하고자 한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것으로 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 통상의 기술자에게 있어서 명백한 것이며, 이들 만으로 본 발명의 범위가 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples. However, the following examples are intended to illustrate the present invention, and it is obvious to those skilled in the art that various changes and modifications are possible within the scope and spirit of the present invention, and the scope of the present invention is not limited to these alone.
[합성예 1][Synthesis Example 1]
100mL 3구 둥근바닥 플라스크에 3-글리시딜옥시프로필 트리메톡시실란 2.717g (11.5mmol)을 담은 후, 이미다졸 0.78g (11.5mmol)을 투입하였다. 다음 플라스크에 증류수 50mL를 첨가한 후, 100℃로 6시간 동안 환류한 다음, 실온에서 추가로 12시간 동안 교반하여 무색의 액체 생성물(화학식 1 구조에 해당하는 화합물)을 얻었다.2.717 g (11.5 mmol) of 3-glycidyloxypropyl trimethoxysilane was placed in a 100 mL three-neck round bottom flask, and then 0.78 g (11.5 mmol) of imidazole was added. Next, 50 mL of distilled water was added to the flask, refluxed at 100°C for 6 hours, and then stirred at room temperature for an additional 12 hours to obtain a colorless liquid product (compound corresponding to the structure of Formula 1).
[실시예 1][Example 1]
하기 표 1의 조성을 갖는 접착제 조성물을 준비하였다.An adhesive composition having the composition shown in Table 1 below was prepared.
[비교예 1][Comparative Example 1]
하기 표 2의 조성을 갖는 접착제 조성물을 준비하였다.An adhesive composition having the composition shown in Table 2 below was prepared.
[제조예 1][Production Example 1]
1 oz 두께이고 표면조도(Ra)가 0.1 ㎛ 이하인 구리박에 실시예 1의 접착제 조성물을 도포하고, 폴리이미드 기재(MGC 830NSF LC)를 적층한 후 220 ℃에서 90 kg/cm2로 2시간 동안 눌러 구리박과 폴리이미드 기재가 결합된 회로기판을 제조하였다.The adhesive composition of Example 1 was applied to a copper foil with a thickness of 1 oz and a surface roughness (Ra) of 0.1 ㎛ or less, laminated with a polyimide base (MGC 830NSF LC), and then incubated at 220°C at 90 kg/cm 2 for 2 hours. A circuit board combining copper foil and polyimide substrate was manufactured by pressing.
[제조예 2][Production Example 2]
1 oz 두께이고 표면조도(Ra)가 0.5-1 ㎛인 구리박에 실시예 1의 접착제 조성물을 도포하고, 폴리이미드 기재(MGC 830NSF LC)를 적층한 후 220℃에서 90kg/cm2로 2시간 동안 눌러 구리박과 폴리이미드 기재가 결합되도록 하였다.The adhesive composition of Example 1 was applied to a copper foil with a thickness of 1 oz and a surface roughness (Ra) of 0.5-1 ㎛, laminated with a polyimide base (MGC 830NSF LC), and incubated at 90 kg/cm 2 at 220°C for 2 hours. Press for a while to bond the copper foil and polyimide substrate.
[비교제조예 1][Comparative Manufacturing Example 1]
실시예 1의 접착제 조성물 대신에 비교예 1의 접착제 조성물을 사용하는 것을 제외하고는 제조예 1과 동일한 조건으로 회로기판을 제조하였다.A circuit board was manufactured under the same conditions as Preparation Example 1, except that the adhesive composition of Comparative Example 1 was used instead of the adhesive composition of Example 1.
[비교제조예 2][Comparative Manufacturing Example 2]
실시예 1의 접착제 조성물 대신에 비교예 1의 접착제 조성물을 사용하는 것을 제외하고는 제조예 2와 동일한 조건으로 회로기판을 제조하였다.A circuit board was manufactured under the same conditions as Preparation Example 2, except that the adhesive composition of Comparative Example 1 was used instead of the adhesive composition of Example 1.
[실험예 1][Experimental Example 1]
제조예 및 비교제조예에서 각각 제조된 회로기판의 박리강도(gf/cm)를 수직이형시험으로(이형속도: 50mm/min) 표준 규격에 의거하여 측정하였으며, 그 결과를 도 3에 나타내었다.The peel strength (g f /cm) of the circuit boards manufactured in each of the manufacturing examples and comparative manufacturing examples was measured according to standard specifications through a vertical release test (release speed: 50 mm/min), and the results are shown in Figure 3. .
도 3을 참조하면, 본 발명에 따른 접착제 조성물인 실시예 1이 적용된 회로기판이 높은 접착력을 나타내는 것을 확인할 수 있었다.Referring to Figure 3, it was confirmed that the circuit board to which Example 1, the adhesive composition according to the present invention, was applied showed high adhesive strength.
Claims (6)
[화학식 1]
(상기 화학식 1에서,
R1은 수소 및 C1 내지 C10의 알킬기로 이루어진 군에서 선택되고, 이때, 복수의 R1은 서로 동일하거나 상이하고,
R2는 이미다졸기이고,
A는 에테르기이고,
상기 R1, R2, A 및 L는 각각 독립적으로, 아미노기, C1 내지 C10의 알킬기, C1 내지 C10의 알킬렌아민기, C6 내지 C20의 아릴기 및 C2 내지 C20의 헤테로아릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환 또는 비치환된다.)
금속 이온 공급원; 및
pH 조절제를 포함하는 접착제 조성물.A silane-based adhesion promoter comprising a structure represented by the following formula (1);
[Formula 1]
(In Formula 1 above,
R1 is selected from the group consisting of hydrogen and C1 to C10 alkyl groups, wherein the plurality of R1 is the same or different from each other,
R2 is an imidazole group,
A is an ether group,
R1, R2, A and L are each independently selected from the group consisting of an amino group, a C1 to C10 alkyl group, a C1 to C10 alkyleneamine group, a C6 to C20 aryl group, and a C2 to C20 heteroaryl group. Substituted or unsubstituted with more than one substituent.)
metal ion source; and
An adhesive composition comprising a pH adjusting agent.
상기 R1은 메틸기, 에틸기 또는 프로필기인 것인 접착제 조성물.In claim 1,
The adhesive composition wherein R 1 is a methyl group, an ethyl group, or a propyl group.
이온안정제, pH 완충제 및 접착 보조제로 이루어진 군에서 선택되는 1종 이상의 첨가제; 및
용매를 더 포함하는 것인 접착제 조성물.In claim 1,
At least one additive selected from the group consisting of ion stabilizers, pH buffers, and adhesion aids; and
An adhesive composition further comprising a solvent.
상기 실란계 접착 촉진제의 함량이 조성물 총 중량%을 기준으로 0.1 내지 30 중량%인 것인 접착제 조성물.
In claim 1,
An adhesive composition wherein the content of the silane-based adhesion promoter is 0.1 to 30% by weight based on the total weight% of the composition.
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