TW202411390A

TW202411390A - 黏著劑組成物、黏合薄膜、附有黏著劑組成物層的積層體、積層體、及電磁波屏蔽薄膜

黏著劑組成物、黏合薄膜、附有黏著劑組成物層的積層體、積層體、及電磁波屏蔽薄膜 Download PDF

Info

Publication number: TW202411390A
Authority: TW; Taiwan
Prior art keywords: adhesive composition; polyester; acid; carbon atoms; resin
Prior art date: 2022-07-06

Application number

TW112125058A

Other languages

English (en)

Chinese (zh)

Inventor

安藤勝

鳥居雅弘

岩田愛

平川真

Original Assignee

日商東亞合成股份有限公司

Priority date

2022-07-06

Filing date

2023-07-05

Publication date

2024-03-16

2023-07-05 Application filed by 日商東亞合成股份有限公司 filed Critical 日商東亞合成股份有限公司

2024-03-16 Publication of TW202411390A publication Critical patent/TW202411390A/zh

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239000000853 adhesive Substances 0.000 title claims abstract description 252
230000001070 adhesive effect Effects 0.000 title claims abstract description 252
239000000203 mixture Substances 0.000 title claims abstract description 228
229920000728 polyester Polymers 0.000 claims abstract description 184
229920006122 polyamide resin Polymers 0.000 claims abstract description 85
239000003822 epoxy resin Substances 0.000 claims abstract description 75
229920000647 polyepoxide Polymers 0.000 claims abstract description 75
239000004952 Polyamide Substances 0.000 claims abstract description 24
229920002647 polyamide Polymers 0.000 claims abstract description 24
-1 aromatic diol Chemical class 0.000 claims description 172
125000004432 carbon atom Chemical group C* 0.000 claims description 106
229920005749 polyurethane resin Polymers 0.000 claims description 67
229920005989 resin Polymers 0.000 claims description 53
239000011347 resin Substances 0.000 claims description 53
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 47
125000001931 aliphatic group Chemical group 0.000 claims description 36
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 35
239000000047 product Substances 0.000 claims description 26
125000002723 alicyclic group Chemical group 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 24
239000011256 inorganic filler Substances 0.000 claims description 24
229910003475 inorganic filler Inorganic materials 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
150000001412 amines Chemical class 0.000 claims description 20
239000000758 substrate Substances 0.000 claims description 20
239000011231 conductive filler Substances 0.000 claims description 19
239000012766 organic filler Substances 0.000 claims description 19
239000000463 material Substances 0.000 claims description 15
238000010521 absorption reaction Methods 0.000 claims description 13
239000002313 adhesive film Substances 0.000 claims description 12
150000004985 diamines Chemical class 0.000 claims description 10
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
125000005370 alkoxysilyl group Chemical group 0.000 claims description 6
239000007859 condensation product Substances 0.000 claims description 5
238000007654 immersion Methods 0.000 claims description 5
239000010410 layer Substances 0.000 description 90
239000002253 acid Substances 0.000 description 87
239000010408 film Substances 0.000 description 62
239000002245 particle Substances 0.000 description 56
238000012360 testing method Methods 0.000 description 50
229910000679 solder Inorganic materials 0.000 description 43
150000001875 compounds Chemical class 0.000 description 34
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 33
239000004848 polyfunctional curative Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 29
229920001721 polyimide Polymers 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 26
239000011889 copper foil Substances 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
230000007774 longterm Effects 0.000 description 21
238000000034 method Methods 0.000 description 20
229920005862 polyol Polymers 0.000 description 20
239000012790 adhesive layer Substances 0.000 description 19
150000003077 polyols Chemical class 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000003063 flame retardant Substances 0.000 description 16
229910052751 metal Inorganic materials 0.000 description 16
239000002184 metal Substances 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
150000008064 anhydrides Chemical class 0.000 description 14
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 14
238000003860 storage Methods 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
125000000217 alkyl group Chemical group 0.000 description 13
238000000576 coating method Methods 0.000 description 13
238000005259 measurement Methods 0.000 description 13
238000005476 soldering Methods 0.000 description 13
239000007787 solid Substances 0.000 description 13
239000004970 Chain extender Substances 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
239000011248 coating agent Substances 0.000 description 12
125000002883 imidazolyl group Chemical group 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
239000011241 protective layer Substances 0.000 description 11
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
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SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
150000002009 diols Chemical class 0.000 description 9
238000011156 evaluation Methods 0.000 description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 8
BCJIMAHNJOIWKQ-UHFFFAOYSA-N 4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]-2-benzofuran-1,3-dione Chemical compound O=C1OC(=O)C2=C1C=CC=C2OC1=CC=CC2=C1C(=O)OC2=O BCJIMAHNJOIWKQ-UHFFFAOYSA-N 0.000 description 8
125000005442 diisocyanate group Chemical group 0.000 description 8
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
229920000768 polyamine Polymers 0.000 description 8
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 8
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 7
229920002799 BoPET Polymers 0.000 description 7
125000002947 alkylene group Chemical group 0.000 description 7
238000001035 drying Methods 0.000 description 7
125000003700 epoxy group Chemical group 0.000 description 7
150000002148 esters Chemical group 0.000 description 7
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000008065 acid anhydrides Chemical class 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000011247 coating layer Substances 0.000 description 6
239000010949 copper Substances 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
230000009477 glass transition Effects 0.000 description 6
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
238000010030 laminating Methods 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
239000002994 raw material Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
229910052623 talc Inorganic materials 0.000 description 6
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
239000007822 coupling agent Substances 0.000 description 5
239000013039 cover film Substances 0.000 description 5
230000018044 dehydration Effects 0.000 description 5
238000006297 dehydration reaction Methods 0.000 description 5
238000001879 gelation Methods 0.000 description 5
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
239000005011 phenolic resin Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
229920005906 polyester polyol Polymers 0.000 description 5
239000005056 polyisocyanate Substances 0.000 description 5
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239000001294 propane Substances 0.000 description 5
239000000454 talc Substances 0.000 description 5
238000005382 thermal cycling Methods 0.000 description 5
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 4
VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 4
ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 4
QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 4
QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 4
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125000000524 functional group Chemical group 0.000 description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
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239000011572 manganese Substances 0.000 description 4
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125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
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XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 3
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229920001971 elastomer Polymers 0.000 description 3
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238000005886 esterification reaction Methods 0.000 description 3
239000011888 foil Substances 0.000 description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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239000013638 trimer Substances 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
YNOWBNNLZSSIHM-UHFFFAOYSA-N tris(oxiran-2-ylmethyl) benzene-1,2,4-tricarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 YNOWBNNLZSSIHM-UHFFFAOYSA-N 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1
239000011667 zinc carbonate Substances 0.000 description 1
229910000010 zinc carbonate Inorganic materials 0.000 description 1
235000004416 zinc carbonate Nutrition 0.000 description 1
DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
GYKKGOMJFMCRIN-UHFFFAOYSA-L zinc;ethyl(methyl)phosphinate Chemical compound [Zn+2].CCP(C)([O-])=O.CCP(C)([O-])=O GYKKGOMJFMCRIN-UHFFFAOYSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1