JP6555126B2 - ポリイミド樹脂、これを用いた樹脂組成物および積層フィルム - Google Patents
ポリイミド樹脂、これを用いた樹脂組成物および積層フィルム Download PDFInfo
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- JP6555126B2 JP6555126B2 JP2015524565A JP2015524565A JP6555126B2 JP 6555126 B2 JP6555126 B2 JP 6555126B2 JP 2015524565 A JP2015524565 A JP 2015524565A JP 2015524565 A JP2015524565 A JP 2015524565A JP 6555126 B2 JP6555126 B2 JP 6555126B2
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- diamine
- laminated
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- 229920001721 polyimide Polymers 0.000 title claims description 92
- 239000009719 polyimide resin Substances 0.000 title claims description 47
- 239000011342 resin composition Substances 0.000 title claims description 43
- 239000000758 substrate Substances 0.000 claims description 130
- -1 polysiloxane Polymers 0.000 claims description 64
- 229920006223 adhesive resin Polymers 0.000 claims description 43
- 150000004985 diamines Chemical class 0.000 claims description 35
- 239000004065 semiconductor Substances 0.000 claims description 35
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 239000004840 adhesive resin Substances 0.000 claims description 30
- 229920001296 polysiloxane Polymers 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 229920005575 poly(amic acid) Polymers 0.000 claims description 26
- 125000004427 diamine group Chemical group 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 230000009477 glass transition Effects 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000010030 laminating Methods 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 description 47
- 239000000853 adhesive Substances 0.000 description 46
- 150000003376 silicon Chemical class 0.000 description 39
- 238000010438 heat treatment Methods 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
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- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 27
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 22
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
- 239000010703 silicon Substances 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 13
- 238000005979 thermal decomposition reaction Methods 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 239000004642 Polyimide Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000004984 aromatic diamines Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 7
- 239000005340 laminated glass Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
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- 150000000000 tetracarboxylic acids Chemical class 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- 239000011800 void material Substances 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- WFNVGXBEWXBZPL-UHFFFAOYSA-N 3,5-diaminophenol Chemical compound NC1=CC(N)=CC(O)=C1 WFNVGXBEWXBZPL-UHFFFAOYSA-N 0.000 description 2
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 230000001771 impaired effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 238000006386 neutralization reaction Methods 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
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- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
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- XQRUEDXXCQDNOT-UHFFFAOYSA-N 2,5-diaminophenol Chemical compound NC1=CC=C(N)C(O)=C1 XQRUEDXXCQDNOT-UHFFFAOYSA-N 0.000 description 1
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- YVOGPMNNTMRGFJ-UHFFFAOYSA-N 2-amino-4-[4-[4-(3-amino-4-hydroxyphenoxy)phenyl]sulfonylphenoxy]phenol Chemical compound C1=C(O)C(N)=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C(O)=CC=3)=CC=2)=C1 YVOGPMNNTMRGFJ-UHFFFAOYSA-N 0.000 description 1
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- MESFSCWCECYZNL-UHFFFAOYSA-N 2-amino-5-[3-(4-amino-3-hydroxyphenoxy)phenoxy]phenol Chemical compound C1=C(O)C(N)=CC=C1OC1=CC=CC(OC=2C=C(O)C(N)=CC=2)=C1 MESFSCWCECYZNL-UHFFFAOYSA-N 0.000 description 1
- VFESRTJMKZNUQW-UHFFFAOYSA-N 2-amino-5-[3-(4-amino-3-hydroxyphenyl)phenyl]phenol Chemical compound NC1=C(C=C(C=C1)C1=CC(=CC=C1)C1=CC(=C(C=C1)N)O)O VFESRTJMKZNUQW-UHFFFAOYSA-N 0.000 description 1
- IWSMXNBXLLQTKL-UHFFFAOYSA-N 2-amino-5-[4-[2-[4-(4-amino-3-hydroxyphenoxy)phenyl]propan-2-yl]phenoxy]phenol Chemical compound C=1C=C(OC=2C=C(O)C(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C(O)=C1 IWSMXNBXLLQTKL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
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- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- UMSVUULWTOXCQY-UHFFFAOYSA-N phenanthrene-1,2,7,8-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1C(O)=O UMSVUULWTOXCQY-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
- B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
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- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
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- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
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- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
なお、ここで残基とは、ポリマーなどの化学物質中に存在し、原料由来の化学構造を意味し、ここでは原料の名称またはその略称を付して表現される。
左上:ニカラックMW−30HM、ニカラックMW−100LM
右上:ニカラックMX−270
左下:ニカラックMX−280
右下:ニカラックMX−290
本発明においては、樹脂組成物に一般式(1)で表されるポリシロキサン系ジアミンの残基および水酸基を有するジアミンの残基を有するポリイミド樹脂に、さらにメチロール化合物を含有することで、熱処理工程時の樹脂組成物硬化膜の流動性を強く抑制し、接着力の上昇を抑えることができるため、被着体となる基材の剥離時に室温でより容易に剥離することができる。
下記製造例1〜22に記載のポリアミド酸樹脂溶液(PA−1〜22)、製造例23〜29の粘着剤樹脂溶液を厚さ18μmの電解銅箔の光沢面に厚さ20μmになるようにバーコーターで塗布後、80℃で10分、150℃で10分乾燥し、さらに窒素雰囲気下250℃で10分加熱処理を行って、ポリイミドに変換し、粘着剤樹脂積層銅箔を得た。次に得られた粘着剤樹脂積層銅箔の銅箔を塩化第2鉄溶液で全面エッチングし、粘着剤樹脂の単膜を得た。
上記で得られた粘着剤樹脂の単膜約15mgをアルミ製標準容器に詰め、熱重量分析装置 TGA−50(島津製作所(株)製)を用いて測定した。測定条件は、60℃で30分保持した後、昇温速度5℃/分で500℃まで昇温した。
各実施例および比較例で得られたポリイミドフィルム積層シリコン基板上のポリイミドフィルムを10mm幅に切り目を入れ、10mm幅のポリイミドフィルムをTOYO BOLDWIN社製”テンシロン”UTM−4−100にて引っ張り速度50mm/分、90゜剥離で測定した。
各実施例で得られたガラス基板積層シリコン基板をガラス側から肉眼で観察し、ボイドの有無を評価した。評価基準は下記のとおりである。
A:ボイド無し。
B:100μm以下のサイズのボイド有り。
C:100μm以上のサイズのボイド有り。
試料となるポリシロキサン系ジアミン5gをビーカーに採取し、ここに、IPA:トルエンが1:1の混合溶液を50mL入れ溶解した。次に、京都電子工業(株)製の電位差自動測定装置AT−610を用い、0.1N塩酸水溶液を撹拌しながら滴下し、中和点となる滴下量を求めた。得られた0.1N塩酸水溶液の滴下量から下式(7)を用いて平均分子量を算出した。
2×〔10×36.5×(滴下量(g))〕/5=平均分子量 (7)
次に、用いたポリシロキサン系ジアミンがn=1であった場合およびn=10であった場合の分子量を化学構造式から計算し、nの数値と分子量の関係を一次関数の関係式として求めた。この関係式に上記平均分子量をあてはめ、nの平均値を求めた。
BPDA:3,3’,4,4’−ビフェニルテトラカルボン酸二無水物
ODPA:3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物
BTDA:3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物
APPS1:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:860、式(1)においてn=9)
APPS2:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:3000、式(1)においてn=37)
APPS3:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:3700、式(1)においてn=47)
APPS4:α,ω−ビス(3−アミノプロピル)ポリジメチルシロキサン(平均分子量:4400、式(1)においてn=57)
44DAE:4,4’−ジアミノジフェニルエーテル
APB:1,3−ビス(3−アミノフェノキシ)ベンゼン
35DAP:3,5−ジアミノフェノール
BAP:4,4’−ジヒドロキシ―3,3’―ジアミノフェニルプロパン
DABS:4,4’−ジヒドロキシ―3,3’―ジアミノフェニルスルホン
AHPB:1,3−ビス(4−アミノ−3−ヒドロキシフェニル)ベンゼン
BAHF:4,4’−ジヒドロキシ―3,3’―ジアミノフェニルヘキサフルオロプロパン
BAHPS:ビス(4−(3−アミノ−4−ヒドロキシフェノキシ)ベンゼン)スルホン
100LM:ニカラック(登録商標)MW−100LM(三和ケミカル(株)製)
MX270:ニカラック(登録商標)MX−270(三和ケミカル(株)製)
CCH:シクロヘキサノン 。
温度計、乾燥窒素導入口、温水・冷却水による加熱・冷却装置、および、撹拌装置を付した反応釜に、APPS1 688g(0.8mol)、44DAE 20g(0.1mol)、BAP 25.8g(0.1mol)をCCH 1566gと共に仕込み、溶解させた後、ODPA 310.2g(1mol)を添加し、室温で1時間、続いて60℃で5時間反応させて、40質量%のポリアミド酸樹脂溶液(PA1)を得た。
酸二無水物、ジアミンの種類と仕込量を表1、表2のように変えた以外は製造例1と同様の操作を行い、40質量%のポリアミド酸樹脂溶液(PA2〜PA22)を得た。
撹拌装置を付した反応釜に、製造例15で得たポリアミド酸溶液(PA15) 100g、メチロール系化合物である100LM 0.08gをCCH 0.12gと共に仕込み、室温で2時間撹拌して、40質量%の粘着剤樹脂溶液(AH1)を得た。
メチロール系化合物の種類と仕込量を表3のように変えた以外は製造例23と同様の操作を行い、40質量%の粘着剤樹脂溶液(AH2〜7)を得た。
厚さ0.75mmの8インチシリコンウエハ(信越化学工業(株)社製)上に、製造例3で得られたポリアミド酸樹脂溶液(PA3)を乾燥、イミド化後の厚みが20μmになるようにスピンコーターで回転数を調製して塗布し、120℃で10分熱処理して乾燥した後、250℃で10分熱処理して完全にイミド化を行い、粘着剤樹脂積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表4のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層ガラス基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表4のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層ガラス基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表5のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表5のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表6のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表6のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
ポリアミド酸樹脂溶液を表7のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
粘着剤酸樹脂溶液を表8のごとく変えた以外は、実施例1と同様の操作を行い、ポリイミドフィルム積層シリコン基板、および、ガラス基板積層シリコン基板を得た。
シリコーン樹脂で離型処理した厚み100μm、幅250mmのポリイミドフィルム(“カプトン”300H 東レ・デュポン(株)製)に、製造例26で得られた粘着剤樹脂溶液(AH4)を、乾燥、イミド化後の膜厚が20μmになるようにコンマコーターで塗工後、120℃で1分、続いて250℃で1分熱処理し、片面に粘着剤樹脂層を有する粘着剤樹脂積層フィルムを得た。次に、粘着剤樹脂層上にシリコーン樹脂で離型処理した厚み38μm、幅250mmのPETフィルムを25℃でラミネートし、保護フィルム付き粘着剤樹脂積層フィルムを得た。
厚さ0.75mmの8インチシリコンウエハ(信越化学工業(株)社製)に、製造例26で得られた粘着剤樹脂溶液(AH4)を、乾燥、イミド化後の膜厚が20μmになるようにスピンコーターで塗布後、140℃で10分、続いて250℃で30分熱処理し、粘着剤樹脂積層支持基板を得た。
実施例26で作製した保護フィルム付き粘着剤樹脂積層フィルムの保護フィルムであるPETフィルムを剥がした後、ホットプレート表面温度を120℃に設定したホットプレート上に厚さ0.75mmの8インチシリコンウエハ(信越化学工業(株)社製)を置き、ハンドロールで粘着剤樹脂積層フィルムを圧着した。次に、ポリイミドフィルムを剥がし、250℃で30分熱処理し、粘着剤樹脂積層支持基板を得た。
Claims (15)
- 全ジアミン残基中、水酸基を有するジアミンの残基を0.1〜40モル%含む請求項1記載のポリイミド樹脂。
- ガラス転移温度が30℃以下である請求項1記載のポリイミド樹脂。
- 請求項1〜3のいずれかに記載のポリイミド樹脂、又は該ポリイミド樹脂の前駆体であるポリアミド酸樹脂を含む樹脂組成物。
- メチロール化合物を含む請求項4記載の樹脂組成物。
- メチロール化合物の含有量がポリイミド樹脂、又は、該ポリイミド樹脂の前駆体であるポリアミド酸樹脂に対して0.1〜20質量%である請求項5または6記載の樹脂組成物。
- 請求項4〜7いずれかに記載の樹脂組成物を硬化した硬化膜。
- 耐熱性絶縁フィルムの少なくとも片面に、請求項4〜7いずれかに記載の樹脂組成物を積層した積層フィルム。
- 樹脂組成物を積層する耐熱性絶縁フィルムの表面が離型処理されている請求項9記載の積層フィルム。
- 前記耐熱性絶縁フィルム上に積層された樹脂組成物の表面に、さらに離型処理されたフィルムを積層した請求項9または10記載の積層フィルム。
- 請求項4〜7いずれかに記載の樹脂組成物を用いる半導体装置の製造方法。
- 半導体回路形成用基板と支持基板とが少なくとも1層の粘着剤樹脂層を介して接合され、該粘着剤樹脂層が前記樹脂組成物を用いたものであり、少なくとも、半導体回路形成用基板を薄く加工する工程、半導体回路形成用基板をデバイス加工する工程、および半導体回路形成基板を支持基板から剥離する工程を含む請求項12に記載の半導体装置の製造方法。
- 請求項9〜11いずれかに記載の積層フィルムを用いた半導体装置の製造方法。
- 半導体回路形成用基板と支持基板とが少なくとも1層の粘着剤樹脂層を介して接合され、該粘着剤樹脂層が前記積層フィルムを用いたものであり、少なくとも、半導体回路形成用基板を薄く加工する工程、半導体回路形成用基板をデバイス加工する工程、および半導体回路形成基板を支持基板から剥離する工程を含む請求項14に記載の半導体装置の製造方法。
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