WO2023190555A1 - ポリイミド前駆体組成物、ポリイミドフィルムおよびポリイミドフィルム/基材積層体 - Google Patents
ポリイミド前駆体組成物、ポリイミドフィルムおよびポリイミドフィルム/基材積層体 Download PDFInfo
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- WO2023190555A1 WO2023190555A1 PCT/JP2023/012587 JP2023012587W WO2023190555A1 WO 2023190555 A1 WO2023190555 A1 WO 2023190555A1 JP 2023012587 W JP2023012587 W JP 2023012587W WO 2023190555 A1 WO2023190555 A1 WO 2023190555A1
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- Prior art keywords
- polyimide
- formula
- polyimide film
- polyimide precursor
- mol
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 285
- 239000004642 Polyimide Substances 0.000 title claims abstract description 141
- 239000002243 precursor Substances 0.000 title claims abstract description 118
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 239000000758 substrate Substances 0.000 title claims abstract description 74
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 94
- -1 imidazole compound Chemical class 0.000 claims abstract description 65
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 239000011521 glass Substances 0.000 claims description 27
- 239000010409 thin film Substances 0.000 claims description 22
- 239000004065 semiconductor Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004020 conductor Substances 0.000 claims description 8
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 6
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 230000005540 biological transmission Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 49
- 150000004985 diamines Chemical class 0.000 description 35
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 28
- 239000002904 solvent Substances 0.000 description 22
- 238000002834 transmittance Methods 0.000 description 19
- 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 17
- 239000000178 monomer Substances 0.000 description 17
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 229920005575 poly(amic acid) Polymers 0.000 description 12
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
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- 230000000052 comparative effect Effects 0.000 description 8
- 125000000962 organic group Chemical group 0.000 description 8
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- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 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 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 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 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 230000004888 barrier function Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 238000000137 annealing Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PJWQLRKRVISYPL-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 PJWQLRKRVISYPL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UIZIZIPEEWDBCL-UHFFFAOYSA-N (4-aminophenyl) 4-[4-(4-aminophenoxy)carbonylphenyl]benzoate Chemical compound C1=CC(N)=CC=C1OC(=O)C1=CC=C(C=2C=CC(=CC=2)C(=O)OC=2C=CC(N)=CC=2)C=C1 UIZIZIPEEWDBCL-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
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- BKQWDTFZUNGWNV-UHFFFAOYSA-N 4-(3,4-dicarboxycyclohexyl)cyclohexane-1,2-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(=O)O)CCC1C1CC(C(O)=O)C(C(O)=O)CC1 BKQWDTFZUNGWNV-UHFFFAOYSA-N 0.000 description 2
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 2
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 2
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 2
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 2
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- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 2
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- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
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- 125000006267 biphenyl group Chemical group 0.000 description 2
- 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 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
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- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 2
- UGCMFUQMPWJOON-UHFFFAOYSA-N (1-cycloheptylcycloheptyl)methanediamine Chemical compound C1CCCCCC1C1(C(N)N)CCCCCC1 UGCMFUQMPWJOON-UHFFFAOYSA-N 0.000 description 1
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- SPJXZYLLLWOSLQ-UHFFFAOYSA-N 1-[(1-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CCCCC1(N)CC1(N)CCCCC1 SPJXZYLLLWOSLQ-UHFFFAOYSA-N 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- CJYIPJMCGHGFNN-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic acid Chemical compound C1C2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O CJYIPJMCGHGFNN-UHFFFAOYSA-N 0.000 description 1
- BKDVBBSUAGJUBA-UHFFFAOYSA-N bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid Chemical compound C1=CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O BKDVBBSUAGJUBA-UHFFFAOYSA-N 0.000 description 1
- XQBSPQLKNWMPMG-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O XQBSPQLKNWMPMG-UHFFFAOYSA-N 0.000 description 1
- CFTXGNJIXHFHTH-UHFFFAOYSA-N bis(4-aminophenyl) benzene-1,4-dicarboxylate Chemical compound C1=CC(N)=CC=C1OC(=O)C1=CC=C(C(=O)OC=2C=CC(N)=CC=2)C=C1 CFTXGNJIXHFHTH-UHFFFAOYSA-N 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical compound OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- UYLSVYARXBFEKV-UHFFFAOYSA-N cyclobutane-1,3-diamine Chemical compound NC1CC(N)C1 UYLSVYARXBFEKV-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- CZRKJHRIILZWRC-UHFFFAOYSA-N methyl acetate;propane-1,2-diol Chemical compound COC(C)=O.CC(O)CO CZRKJHRIILZWRC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Definitions
- the present invention relates to a polyimide precursor composition, a polyimide film, and a polyimide film/substrate laminate that are suitably used for electronic device applications such as flexible device substrates.
- Polyimide film has been widely used in fields such as electrical and electronic devices and semiconductors because it has excellent heat resistance, chemical resistance, mechanical strength, electrical properties, and dimensional stability.
- optical materials such as optical fibers and optical waveguides in the field of optical communications, liquid crystal alignment films and protective films for color filters in the field of display devices has progressed.
- lightweight and flexible plastic substrates are being actively investigated as an alternative to glass substrates, and displays that can be bent or rolled are being actively developed.
- TFTs thin film transistors
- the substrate is required to have heat resistance and dimensional stability.
- Polyimide films are promising as substrates for display applications because they have excellent heat resistance, chemical resistance, mechanical strength, electrical properties, and dimensional stability.
- Patent Document 1 describes the process of forming a solid polyimide resin film by coating a specific precursor resin composition on a carrier substrate, and forming a circuit on the resin film.
- a method for manufacturing a flexible device which is a display device or a light receiving device, including the steps of forming a solid resin film on the surface of which the circuit is formed, and peeling off the solid resin film on the surface of which the circuit is formed from the carrier substrate.
- Patent Document 2 describes a method for manufacturing a flexible device in which elements and circuits necessary for the device are formed on a polyimide film/glass substrate laminate obtained by forming a polyimide film on a glass substrate.
- a method is disclosed that includes irradiating a laser beam from the glass substrate side to peel off the glass substrate.
- Polyimide is generally colored yellow-brown, which has limited its use in transmissive devices such as backlit liquid crystal displays, but in recent years polyimide has improved in addition to its mechanical and thermal properties.
- Polyimide films with excellent light transmittance have been developed and are expected to be used as substrates for display applications.
- Patent Documents 4 to 6 describe semi-alicyclic polyimides that have excellent mechanical properties, heat resistance, etc. in addition to optical transparency.
- Patent Document 7 describes a mixture of a fluorine-containing aromatic diamine such as 2,2'-bis(trifluoromethyl)benzidine (TFMB) and trans-1,4-cyclohexyldiamine as a diamine component, and as a tetracarboxylic acid component.
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- trans-1,4-cyclohexyldiamine as a diamine component
- tetracarboxylic acid component a mixture of aliphatic and aromatic tetracarboxylic dianhydrides is disclosed.
- Patent Document 8 also states that ⁇ the diamine includes 2,2'-bistrifluoromethylbenzidine, and the tetracarboxylic dianhydride includes 3,3',4,4'-biphenyltetracarboxylic dianhydride, and 9,9'-(3,4'-dicarboxyphenyl)fluorene dianhydride is included, and 9,9'-(3,4'-dicarboxyphenyl)fluorene dianhydride is based on the total amount of tetracarboxylic anhydride.
- "polyamic acid” in which the amount of is 0.5 mol% or more and 10 mol% or less.
- Aromatic polyimides have problems with coloration, but they generally have excellent heat resistance, so if coloration is reduced as much as possible, they may be used as substrates for display applications.
- Patent Documents 7 and 8 disclose examples of the use of 2,2'-bis(trifluoromethyl)benzidine (TFMB), but the present inventor's investigation revealed that TFMB could be used as a monomer component.
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- the present invention provides a method for producing a polyimide film that has improved light transmittance and adhesion in a polyimide film/substrate laminate while taking advantage of the advantages of aromatic polyimide films such as heat resistance and coefficient of linear thermal expansion.
- the present invention aims to provide a polyimide precursor composition.
- a further object of the present invention is to provide a polyimide film and a polyimide film/substrate laminate obtained from this polyimide precursor.
- one aspect of the present invention aims to provide a polyimide precursor composition with more stable viscosity.
- imidazole compound A polyimide precursor composition comprising:
- X 1 is a tetravalent aliphatic group or aromatic group
- Y 1 is a divalent aliphatic group or aromatic group
- R 1 and R 2 are independently , a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkylsilyl group having 3 to 9 carbon atoms, where: 60 mol% to 90 mol% of X 1 has the formula (1-1):
- At least one type selected from the structures represented by 70 mol% or more of Y 1 is of formula (B):
- Claim 1 wherein 90 mol% or more of X 1 has a structure selected from formula (1-1), formula (1-2), formula (1-3), and formula (1-4).
- imidazole compound is at least one selected from the group consisting of 1,2-dimethylimidazole, 1-methylimidazole, 2-methylimidazole, 2-phenylimidazole, imidazole, and benzimidazole.
- step (b) The method for producing a laminate according to item 10, further comprising the step of (c) forming an inorganic thin film layer on the polyimide film of the laminate.
- a method for manufacturing a flexible electronic device including a step of peeling.
- a polyimide precursor composition can be provided. Furthermore, the present invention can provide a polyimide film and a polyimide film/substrate laminate obtained from this polyimide precursor.
- a polyimide precursor composition with more stable viscosity can be provided.
- a polyimide film and a polyimide film/substrate laminate obtained using the polyimide precursor composition Furthermore, according to another aspect of the present invention, it is possible to provide a method for manufacturing a flexible electronic device using the polyimide precursor composition, and a flexible electronic device.
- the term "flexible (electronic) device” means that the device itself is flexible, and the device is usually completed by forming a semiconductor layer (such as a transistor or diode as an element) on a substrate.
- a “flexible (electronic) device” is distinguished from a device such as a COF (Chip On Film) in which a "hard” semiconductor element such as an IC chip is mounted on a conventional FPC (Flexible Printed Wiring Board).
- “hard” semiconductor elements such as IC chips may be mounted on a flexible substrate or electrically connected and used in combination. There is no problem in doing so.
- Flexible (electronic) devices that are preferably used include display devices such as liquid crystal displays, organic EL displays, and electronic paper, solar cells, and light receiving devices such as CMOS.
- a polyimide precursor composition for forming a polyimide film contains a polyimide precursor and an imidazole compound.
- the polyimide precursor composition further contains a solvent, and both the polyimide precursor and the imidazole compound are dissolved in the solvent.
- the polyimide precursor has the following general formula (I):
- X 1 is a tetravalent aliphatic group or aromatic group
- Y 1 is a divalent aliphatic group or aromatic group
- R 1 and R 2 are independently , a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkylsilyl group having 3 to 9 carbon atoms.
- It has a repeating unit represented by Particularly preferred is a polyamic acid in which R 1 and R 2 are hydrogen atoms.
- the aliphatic group preferably has an alicyclic structure.
- repeating units in the polyimide precursor preferably 60 mol% to 90 mol% of This is a structure derived from
- X 1 preferably 10 to 40 mol% of X 1 is represented by the following formulas (1-2), (1-3) and (1-4):
- ODPA 4,4'-oxydiphthalic dianhydride
- a-BPDA 2,3,3',4'-biphenyltetracarboxylic dianhydride
- BPAF 9,9-bis(3,4-
- BPAF dicarboxyphenyl)fluorene dianhydride
- polyimide film By using a composition containing such a polyimide precursor, it is possible to produce a polyimide film with improved light transmittance and adhesion in the polyimide film/substrate laminate.
- the obtained polyimide film also has excellent properties such as heat resistance and low coefficient of linear thermal expansion, which are advantages of wholly aromatic polyimide films.
- the polyimide precursor will be explained using monomers (tetracarboxylic acid component, diamine component, and other components) that provide X 1 and Y 1 in general formula (I), and then the manufacturing method will be explained.
- the tetracarboxylic acid component refers to tetracarboxylic acid, tetracarboxylic dianhydride, other tetracarboxylic acid silyl esters, tetracarboxylic acid esters, tetracarboxylic acid chlorides, etc. used as raw materials for producing polyimide.
- tetracarboxylic dianhydride it is convenient to use tetracarboxylic dianhydride for production purposes, and in the following description, an example will be described in which tetracarboxylic dianhydride is used as the tetracarboxylic acid component.
- the diamine component is a diamine compound having two amino groups (-NH 2 ), which is used as a raw material for producing polyimide.
- the polyimide film refers to both a film formed on a (carrier) base material and present in a laminate, and a film after the base material is peeled off.
- a material constituting a polyimide film that is, a material obtained by heat-treating (imidizing) a polyimide precursor composition is sometimes referred to as a "polyimide material.”
- X 1 contains 60 mol% to 90 mol% of the structure of formula (1-1) (derived from PMDA), the structure of formula (1-2) (derived from ODPA), and the structure of formula (1-3). Contains 10 to 40 mol% of at least one structure selected from the structure of formula (1-4) (derived from a-BPDA) and the structure of formula (1-4) (derived from BPAF).
- the structure of formula (1-1) is present in a proportion of 70 mol% to 90 mol% in X 1 , and is preferable when a low coefficient of linear thermal expansion is desired.
- the structures of formula (1-2), formula (1-3) and formula (1-4) may include two or more types. Among these structures, the structures of formula (1-2) and/or formula (1-3) are preferred, and the structure of formula (1-2) and/or formula (1-3) accounts for 10 mol% to 40 mol%. % range is also preferred.
- the structure of formula (1-4) is preferably present in an amount of 20 mol% or less, more preferably 10 mol% or less, and when contained, it is combined with the structure of formula (1-2) and/or formula (1-3). It is preferable to use them together.
- the total of the structures represented by formula (1-1), formula (1-2), formula (1-3) and formula (1-4) is preferably 80 mol% or more of X 1 , more preferably is 90 mol% or more, even more preferably 95 mol% or more, and in one particularly preferred embodiment 100 mol%.
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- X 1 is a tetravalent aliphatic group or aromatic group other than the structures represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4).
- the group (abbreviated as "other X 1 ") can be contained in an amount within a range that does not impair the effects of the present invention.
- the aliphatic group is preferably a tetravalent group having an alicyclic structure.
- the tetracarboxylic acid component contains "other tetracarboxylic acid derivatives" other than PMDA, ODPA, a-BPDA and BPAF at 30 mol% or less, more preferably 20 mol% or less, based on 100 mol% of the tetracarboxylic acid component. %, even more preferably 10 mol % or less, even more preferably 5 mol % or less (0 mol % in one particularly preferred embodiment).
- “Other X 1 ” is preferably a tetravalent group having an aromatic ring, and preferably a tetravalent group having an aromatic ring having 6 to 40 carbon atoms.
- “other X 1 " is preferably an aromatic group.
- Examples of the tetravalent group having an aromatic ring include the following. However, groups corresponding to formulas (1-2) and (1-3) are excluded.
- Z 1 is a direct bond or the following divalent group:
- Z 2 in the formula is a divalent organic group
- Z 3 and Z 4 are each independently an amide bond, an ester bond, and a carbonyl bond
- Z 5 is an organic group containing an aromatic ring.
- Z 2 include aliphatic hydrocarbon groups having 2 to 24 carbon atoms and aromatic hydrocarbon groups having 6 to 24 carbon atoms.
- Z 5 include aromatic hydrocarbon groups having 6 to 24 carbon atoms.
- the tetravalent group having an aromatic ring the following are particularly preferable because they can achieve both high heat resistance and high light transmittance of the resulting polyimide film.
- Z 1 is a direct bond or a hexafluoroisopropylidene bond.
- Z1 be a direct bond, since the resulting polyimide film can achieve both high heat resistance, high light transmittance, and a low coefficient of linear thermal expansion.
- Z 1 is the following formula (3A):
- Examples include compounds that are fluorenyl-containing groups represented by: However, groups corresponding to formula (1-4) are excluded.
- Z 11 and Z 12 are each independently, preferably the same, a single bond or a divalent organic group.
- Z 11 and Z 12 are preferably organic groups containing an aromatic ring, for example, formula (3A1):
- Z 13 and Z 14 are each independently a single bond, -COO-, -OCO- or -O-, where Z 14 is bonded to a fluorenyl group, Z 13 is -COO-, -OCO- or -O- with a structure in which Z 14 is a single bond;
- R 91 is an alkyl group having 1 to 4 carbon atoms or a phenyl group, preferably methyl, and n is an integer of 0 to 4, preferably 1.
- a structure represented by is preferable.
- Examples of the tetracarboxylic acid component that provides the repeating unit of general formula (I) in which X 1 is a tetravalent group having an aromatic ring include 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane.
- Examples of the tetracarboxylic acid component providing the repeating unit of general formula (I) in which X 1 is a tetravalent group having an aromatic ring containing a fluorine atom include 2,2-bis(3,4-dicarboxylic acid). (phenyl)hexafluoropropane, and its derivatives such as tetracarboxylic dianhydride, tetracarboxylic acid silyl ester, tetracarboxylic acid ester, and tetracarboxylic acid chloride.
- (9H-fluorene-9,9-diyl)bis(2-methyl-4,1-phenylene)bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylate) can be mentioned.
- the tetracarboxylic acid component may be used alone or in combination.
- Examples of the tetracarboxylic acid component providing the repeating unit of formula (I) in which X 1 is a tetravalent group having an alicyclic structure include 1,2,3,4-cyclobutanetetracarboxylic acid, isopropylidene diphenoxybis Phthalic acid, cyclohexane-1,2,4,5-tetracarboxylic acid, [1,1'-bi(cyclohexane)]-3,3',4,4'-tetracarboxylic acid, [1,1'-bi(cyclohexane)]-3,3',4,4'-tetracarboxylic acid, (cyclohexane)]-2,3,3',4'-tetracarboxylic acid, [1,1'-bi(cyclohexane)]-2,2',3,3'-tetracarboxylic acid, 4,4'- Methylenebis(cyclohexane-1,2-dicarboxylic acid), 4,
- Y 1 contains a structure derived from 2,2'-bis(trifluoromethyl)benzidine (TFMB) in an amount of 70 mol% or more, and the preferable amount is as described above.
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- Y 1 a divalent aliphatic group or aromatic group other than the structure represented by formula (B) (abbreviated as “other Y 1 ”) may be used within the range that does not impair the effects of the present invention. It can be contained in any amount. That is, the diamine component contains other diamine compounds in addition to TFMB, based on 100 mol% of the diamine component, 30 mol% or less, more preferably 20 mol% or less, even more preferably 10 mol% or less, and even more preferably may be present in an amount of up to 5 mol% (0 mol% in one particularly preferred embodiment).
- Y 1 is a divalent group having an aromatic ring, it is preferably a divalent group having an aromatic ring having 6 to 40 carbon atoms, more preferably 6 to 20 carbon atoms.
- Examples of the divalent group having an aromatic ring include the following.
- W 1 is a direct bond or a divalent organic group
- n 11 to n 13 each independently represents an integer of 0 to 4
- R 51 , R 52 , and R 53 each independently is an alkyl group having 1 to 6 carbon atoms, a halogen group, a hydroxyl group, a carboxyl group, or a trifluoromethyl group.
- W 1 examples include a direct bond, a divalent group represented by the following formula (5), and a divalent group represented by the following formula (6).
- R 61 to R 68 in formula (6) each independently represent either a direct bond or a divalent group represented by formula (5) above.
- W 1 is a direct bond or a formula: -NHCO-, -CONH-, -COO-, -OCO-, since the resulting polyimide can achieve both high heat resistance, high light transmittance, and low coefficient of linear thermal expansion. Particularly preferred is one selected from the group consisting of the groups represented by the following. Further, W 1 is one type selected from the group consisting of a direct bond or a group represented by the formula: -NHCO-, -CONH-, -COO- , -OCO-; Particularly preferred is any of the divalent groups represented by formula (6).
- W 1 is the following formula (3B):
- Z 11 and Z 12 are each independently, preferably the same, a single bond or a divalent organic group.
- Z 11 and Z 12 are preferably organic groups containing an aromatic ring, for example, formula (3B1):
- Z 13 and Z 14 are each independently a single bond, -COO-, -OCO- or -O-, where Z 14 is bonded to a fluorenyl group, Z 13 is -COO-, -OCO- or a structure in which Z 14 is a single bond in -O-;
- R 91 is an alkyl group having 1 to 4 carbon atoms or a phenyl group, preferably phenyl, and n is an integer of 0 to 4, preferably 1.
- a structure represented by is preferable.
- Another preferable group includes a compound in which W 1 is a phenylene group in the above formula (4), that is, a terphenyldiamine compound, and a compound in which all of the groups are para bonds is particularly preferable.
- Another preferred group includes a compound in which, in the above formula (4), W 1 is the first phenyl ring of formula (6), and R 61 and R 62 are 2,2-propylidene groups.
- W 1 is the following formula (3B2):
- Examples include compounds represented by:
- Examples of the diamine component that provides Y 1 which is a divalent group having an aromatic ring, include p-phenylenediamine, m-phenylenediamine, benzidine, 3,3'-diamino-biphenyl, 3,3'-bis( trifluoromethyl)benzidine, m-tolidine, 3,4'-diaminobenzanilide, N,N'-bis(4-aminophenyl)terephthalamide, N,N'-p-phenylenebis(p-aminobenzamide), 4-aminophenoxy-4-diaminobenzoate, bis(4-aminophenyl) terephthalate, biphenyl-4,4'-dicarboxylic acid bis(4-aminophenyl) ester, p-phenylene bis(p-aminobenzoate), bis( 4-aminophenyl)-[1,1'-biphenyl]-4,4'-dicarboxy
- Examples of the diamine component providing the repeating unit of general formula (I) in which Y 1 is a divalent group having an aromatic ring containing a fluorine atom include 2,2'-bis(trifluoromethyl)benzidine, 3 , 3'-bis(trifluoromethyl)benzidine, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2 '-bis(3-amino-4-hydroxyphenyl)hexafluoropropane.
- preferred diamine compounds include 9,9-bis(4-aminophenyl)fluorene, 4,4'-(((9H-fluorene-9,9-diyl)bis([1,1'-biphenyl]-5 ,2-diyl))bis(oxy))diamine, [1,1':4',1"-terphenyl]-4,4"-diamine, 4,4'-([1,1'-binaphthalene] -2,2'-diylbis(oxy))diamine is mentioned.
- the diamine component may be used alone or in combination.
- Y 1 is a divalent group having an alicyclic structure, it is preferably a divalent group having an alicyclic structure having 4 to 40 carbon atoms, at least one aliphatic 4 to 12-membered ring, More preferably, it has an aliphatic 6-membered ring.
- divalent group having an alicyclic structure examples include the following.
- V 1 and V 2 are each independently a direct bond or a divalent organic group
- n 21 to n 26 each independently represent an integer of 0 to 4
- R 81 to R 86 are each independently an alkyl group having 1 to 6 carbon atoms, a halogen group, a hydroxyl group, a carboxyl group, or a trifluoromethyl group
- V 1 and V 2 include a direct bond and a divalent group represented by the above formula (5).
- Examples of the diamine component that provides Y 1 which is a divalent group having an alicyclic structure, include 1,4-diaminocyclohexane, 1,4-diamino-2-methylcyclohexane, and 1,4-diamino-2- Ethylcyclohexane, 1,4-diamino-2-n-propylcyclohexane, 1,4-diamino-2-isopropylcyclohexane, 1,4-diamino-2-n-butylcyclohexane, 1,4-diamino-2-isobutylcyclohexane , 1,4-diamino-2-sec-butylcyclohexane, 1,4-diamino-2-tert-butylcyclohexane, 1,2-diaminocyclohexane, 1,3-diaminocyclobutane, 1,4-bis(amino a
- any of aliphatic tetracarboxylic acids (especially dianhydrides) other than alicyclic type and/or aliphatic diamines are used.
- the content thereof is preferably less than 30 mol%, more preferably less than 20 mol%, even more preferably less than 10 mol% ( (including 0%) is preferable.
- Y 1 the structure represented by formula (3B)
- specific compounds include diamine compounds such as 9,9-bis(4-aminophenyl)fluorene, which can improve Tg and It may be possible to reduce the phase difference (retardation) in the film thickness direction.
- the polyimide precursor can be produced from the above tetracarboxylic acid component and diamine component.
- the polyimide precursor (polyimide precursor containing at least one type of repeating unit represented by the above formula (I)) used in the present invention has the following chemical structure, depending on the chemical structure taken by R 1 and R 2 : 1) polyamic acid (R 1 and R 2 are hydrogen), 2) polyamic acid ester (at least a portion of R 1 and R 2 is an alkyl group), 3) 4) Polyamic acid silyl ester (at least a portion of R 1 and R 2 is an alkylsilyl group), It can be classified into The polyimide precursor can be easily manufactured by the following manufacturing method for each category. However, the method for producing the polyimide precursor used in the present invention is not limited to the following production method.
- the polyimide precursor contains approximately equal moles of tetracarboxylic dianhydride as a tetracarboxylic acid component and a diamine component in a solvent, preferably at a molar ratio of the diamine component to the tetracarboxylic acid component [mole of the diamine component]. number/number of moles of tetracarboxylic acid component] is preferably 0.90 to 1.10, more preferably 0.95 to 1.05, and imidization is suppressed at a relatively low temperature of, for example, 120 ° C. or less.
- a polyimide precursor solution can be suitably obtained by reacting the polyimide precursor solution.
- diamine is dissolved in an organic solvent or water, and tetracarboxylic dianhydride is gradually added to this solution while stirring, and the temperature is 0 to 120°C, preferably 5°C.
- a polyimide precursor can be obtained by stirring at a temperature of ⁇ 80°C for 1 to 72 hours.
- the reaction is carried out at 80° C. or higher, the molecular weight varies depending on the temperature history during polymerization, and imidization progresses due to heat, so there is a possibility that the polyimide precursor cannot be stably produced.
- the order of addition of diamine and tetracarboxylic dianhydride in the above production method is preferable because the molecular weight of the polyimide precursor tends to increase.
- the amount of imidazole such as 1,2-dimethylimidazole or a base such as triethylamine is preferably 0.8 times equivalent to the carboxyl group of the polyamic acid (polyimide precursor) to be produced. It is preferable to add the above amount.
- a polyimide precursor is obtained by stirring this diesterdicarboxylic acid chloride and diamine at a temperature of -20 to 120°C, preferably -5 to 80°C for 1 to 72 hours.
- the reaction is carried out at 80° C. or higher, the molecular weight varies depending on the temperature history during polymerization, and imidization progresses due to heat, so there is a possibility that the polyimide precursor cannot be stably produced.
- a polyimide precursor can be easily obtained by dehydrating and condensing a diester dicarboxylic acid and a diamine using a phosphorus condensing agent, a carbodiimide condensing agent, or the like.
- the polyimide precursor obtained by this method is stable, it can also be purified by reprecipitation by adding a solvent such as water or alcohol.
- a polyimide precursor is obtained by mixing the polyamic acid solution obtained by method 1) with a silylating agent and stirring at a temperature of 0 to 120°C, preferably 5 to 80°C for 1 to 72 hours.
- a silylating agent preferably 5 to 80°C for 1 to 72 hours.
- the reaction is carried out at 80° C. or higher, the molecular weight varies depending on the temperature history during polymerization, and imidization progresses due to heat, so there is a possibility that the polyimide precursor cannot be stably produced.
- silylating agent that does not contain chlorine as the silylating agent used in the methods 3) and 4) eliminates the need to purify the silylated polyamic acid or the obtained polyimide.
- the silylating agent that does not contain a chlorine atom include N,O-bis(trimethylsilyl)trifluoroacetamide, N,O-bis(trimethylsilyl)acetamide, and hexamethyldisilazane. N,O-bis(trimethylsilyl)acetamide and hexamethyldisilazane are particularly preferred because they do not contain fluorine atoms and are low cost.
- an amine catalyst such as pyridine, piperidine, or triethylamine can be used to promote the reaction.
- This catalyst can be used as it is as a polymerization catalyst for polyimide precursors.
- Solvents used in preparing the polyimide precursor include water, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, 1,3 -Aprotic solvents such as dimethyl-2-imidazolidinone and dimethyl sulfoxide are preferred; any type of solvent can be used without any problem as long as it dissolves the raw material monomer component and the polyimide precursor to be produced; It is not limited to that structure.
- an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethyl-2-pyrrolidone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone.
- cyclic ester solvents such as ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -butyrolactone, carbonate solvents such as ethylene carbonate and propylene carbonate, glycol solvents such as triethylene glycol, m-cresol, p-cresol, 3 Phenolic solvents such as -chlorophenol and 4-chlorophenol, acetophenone, 1,3-dimethyl-2-imidazolidinone, sulfolane, and dimethyl sulfoxide are preferably employed.
- the reaction is carried out by charging monomers and a solvent at a concentration such that the solid content concentration (polyimide equivalent mass concentration) of the polyimide precursor is, for example, 5 to 45% by mass, although it is not particularly limited.
- the logarithmic viscosity of the polyimide precursor is not particularly limited, but the logarithmic viscosity in an N-methyl-2-pyrrolidone solution with a concentration of 0.5 g/dL at 30°C is 0.2 dL/g or more, more preferably 0.3 dL/ It is preferably at least 0.4 dL/g, particularly preferably at least 0.4 dL/g.
- the logarithmic viscosity is 0.2 dL/g or more, the molecular weight of the polyimide precursor is high, and the resulting polyimide has excellent mechanical strength and heat resistance.
- the polyimide precursor composition contains at least one imidazole compound.
- the imidazole compound is not particularly limited as long as it has an imidazole skeleton, and examples thereof include 1,2-dimethylimidazole, 1-methylimidazole, 2-methylimidazole, 2-phenylimidazole, imidazole, and benzimidazole. A plurality of imidazole compounds may be used in combination.
- the content of the imidazole compound in the polyimide precursor composition can be appropriately selected in consideration of the balance between the effect of addition and the stability of the polyimide precursor composition.
- the amount of imidazole compound (total content) is preferably in the range of 0.05 mol to 2 mol per mol of repeating unit of the polyimide precursor. Addition of an imidazole compound is effective in improving the adhesion between the polyimide film and the base material (increasing the peel strength) in the polyimide film/base material laminate, and is also effective in improving the transmittance. Furthermore, a tendency for the coefficient of linear thermal expansion to decrease is also observed.
- the monomer composition of the present invention it has been found that addition of an appropriate amount of an imidazole compound is effective in stabilizing the viscosity of the polyimide precursor composition.
- the viscosity of a polyimide precursor solution having the same monomer composition as that of the present invention increases slowly and requires a long period of time to reach the maximum value when no imidazole compound is added or when a small amount is added.
- the amount of imidazole compound is excessive, the viscosity decreases rapidly after reaching its maximum value.
- the content of the imidazole compound is more preferably 0.08 mol or more, even more preferably 0.1 mol or more, even more preferably 0.4 mol or more, and even more preferably It is 1.8 mol or less, even more preferably 1.5 mol or less.
- the polyimide precursor composition used in the present invention comprises at least one polyimide precursor, at least one imidazole compound as described above, and preferably a solvent.
- the solvent those described above as solvents used when preparing the polyimide precursor can be used.
- the solvent used when preparing the polyimide precursor can be used as it is, that is, as the polyimide precursor solution, but it may be diluted or concentrated if necessary.
- the imidazole compound is present in solution in the polyimide precursor composition.
- the concentration of the polyimide precursor is not particularly limited, but is usually 5 to 45% by mass in polyimide equivalent mass concentration (solid content concentration).
- the polyimide equivalent mass is the mass when all of the repeating units are completely imidized.
- the viscosity (rotational viscosity ) of the polyimide precursor composition of the present invention is not particularly limited; ⁇ sec is preferable, and 0.1 to 100 Pa ⁇ sec is more preferable. Additionally, thixotropy can be imparted if necessary. When the viscosity is in the above range, it is easy to handle when coating or forming a film, and since repelling is suppressed and the leveling property is excellent, a good film can be obtained.
- the polyimide precursor composition of the present invention may contain chemical imidizing agents (acid anhydrides such as acetic anhydride, amine compounds such as pyridine and isoquinoline), antioxidants, ultraviolet absorbers, fillers (silica, etc.), as necessary. (inorganic particles, etc.), dyes, pigments, coupling agents such as silane coupling agents, primers, flame retardants, antifoaming agents, leveling agents, rheology control agents (flow aids), etc.
- chemical imidizing agents as acid anhydrides such as acetic anhydride, amine compounds such as pyridine and isoquinoline
- antioxidants antioxidants
- ultraviolet absorbers fillers (silica, etc.)
- fillers silicon, etc.
- the polyimide precursor composition can be prepared by adding and mixing an imidazole compound or a solution of an imidazole compound to the polyimide precursor solution obtained by the method described above.
- the tetracarboxylic acid component and the diamine component may be reacted in the presence of an imidazole compound.
- a polyimide film/substrate laminate can be manufactured using the polyimide precursor composition of the present invention.
- the polyimide film/substrate laminate includes (a) applying a polyimide precursor composition onto a substrate, (b) heat-treating the polyimide precursor on the substrate, and applying polyimide onto the substrate. It can be manufactured by a process of manufacturing a laminate (polyimide film/base material laminate) in which films are laminated.
- the method for producing a flexible electronic device of the present invention uses the polyimide film/substrate laminate produced in the steps (a) and (b) (preferably further step (b2)), and further steps ( c) forming at least one layer selected from a conductor layer and a semiconductor layer on the polyimide film of the laminate; and (d) peeling off the base material and the polyimide film.
- step (a) a polyimide precursor composition is cast onto a base material, imidized and solvent removed by heat treatment to form a polyimide film, and a laminate of the base material and polyimide film (polyimide A film/substrate laminate) is obtained.
- heat-resistant materials are used, such as ceramic materials (glass, alumina, etc.), metal materials (iron, stainless steel, copper, aluminum, etc.), semiconductor materials (silicon, compound semiconductors, etc.), etc.
- a sheet-like base material or a film or sheet-like base material such as a heat-resistant plastic material (polyimide, etc.) is used.
- glass substrates such as soda lime glass, borosilicate glass, alkali-free glass, and sapphire glass
- semiconductor (including compound semiconductor) substrates such as silicon, GaAs, InP, and GaN
- Metal substrates such as iron, stainless steel, copper, and aluminum are used.
- a glass substrate is particularly preferred as the base material. Glass substrates that are flat, smooth, and have a large area have been developed and are easily available.
- the thickness of the plate-like substrate such as a glass substrate is not limited, but from the viewpoint of ease of handling, it is, for example, 20 ⁇ m to 4 mm, preferably 100 ⁇ m to 2 mm.
- the size of the plate-shaped base material is not particularly limited, but one side (the long side in the case of a rectangle) is, for example, about 100 mm to about 4000 mm, preferably about 200 mm to about 3000 mm, more preferably about 300 mm to 2500 mm. It is.
- These base materials such as glass substrates may have an inorganic thin film (for example, a silicon oxide film) or a resin thin film formed on the surface.
- an inorganic thin film for example, a silicon oxide film
- a resin thin film formed on the surface.
- the method for casting the polyimide precursor composition onto the base material is not particularly limited, but includes, for example, slit coating, die coating, blade coating, spray coating, inkjet coating, nozzle coating, spin coating, and screen printing. Conventionally known methods such as a method, a bar coater method, and an electrodeposition method can be used.
- step (b) the polyimide precursor composition is heat-treated on the substrate to convert it into a polyimide film, and a polyimide film/substrate laminate is obtained.
- the heat treatment conditions are not particularly limited, but for example, after drying at a temperature range of 50°C to 150°C, the maximum heating temperature is, for example, 150°C to 600°C, preferably 200°C to 550°C, more preferably 250°C.
- the treatment is carried out at a temperature of ⁇ 500°C.
- the thickness of the polyimide film is preferably 1 ⁇ m or more, more preferably 2 ⁇ m or more, and still more preferably 5 ⁇ m or more. When the thickness is less than 1 ⁇ m, the polyimide film cannot maintain sufficient mechanical strength, and when used, for example, as a flexible electronic device substrate, may not be able to withstand stress and may be destroyed. Moreover, the thickness of the polyimide film is preferably 100 ⁇ m or less, more preferably 50 ⁇ m or less, and still more preferably 20 ⁇ m or less. When the thickness of the polyimide film becomes thick, it may become difficult to make the flexible device thinner. In order to make the polyimide film thinner while maintaining sufficient durability as a flexible device, the thickness of the polyimide film is preferably 2 to 50 ⁇ m.
- the polyimide film/substrate laminate has small warpage. Details of the measurement are described in Japanese Patent No. 6798633.
- the residual stress is preferably less than 27 MPa.
- the polyimide film is placed in a dry state at 23°C.
- the polyimide film in the polyimide film/substrate laminate may have a second layer such as an inorganic thin film on the surface. It is preferable to include a step of forming a thin film.
- the inorganic thin film is preferably one that functions as a barrier layer against water vapor, oxygen (air), and the like.
- the water vapor barrier layer include silicon nitride (SiN x ), silicon oxide (SiO x ), silicon oxynitride (SiO x N y ), aluminum oxide (Al 2 O 3 ), titanium oxide (TiO 2 ), and zirconium oxide.
- Examples include inorganic thin films containing an inorganic substance selected from the group consisting of metal oxides, metal nitrides, and metal oxynitrides such as (ZrO 2 ).
- methods for forming these thin films include physical vapor deposition methods such as vacuum evaporation, sputtering, and ion plating, and chemical vapor deposition such as plasma CVD and catalytic chemical vapor deposition (Cat-CVD). (CVD: chemical vapor deposition method) and the like are known.
- CVD chemical vapor deposition method
- the film is densified by performing high temperature annealing at, for example, 350° C. to 450° C. after film forming.
- inorganic thin film refers to both before and after annealing. If only one or the other is meant, it will be explicitly indicated or clear from the context. Similarly, “polyimide film/substrate laminate” means both those with and without “inorganic thin films”.
- This second layer can also be made into multiple layers.
- different types of inorganic thin films may be formed, or a resin film and an inorganic thin film may be combined.
- An example of the latter is, for example, an example in which a three-layer structure of barrier layer/polyimide layer/barrier layer is formed on a polyimide film in a polyimide film/substrate laminate.
- step (c) the polyimide/substrate laminate obtained in step (b) is used to coat a polyimide film (including one in which a second layer such as an inorganic thin film is laminated on the surface of the polyimide film). At least one layer selected from a conductor layer and a semiconductor layer is formed. These layers may be formed directly on the polyimide film (including a second layer laminated) or indirectly, on top of other layers necessary for the device. good.
- step (c) of the present invention when forming at least one of the conductor layer and the semiconductor layer, it is also preferable to form at least one of the conductor layer and the semiconductor layer on a polyimide film on which an inorganic film is formed.
- the conductive layer and the semiconductor layer include both those formed on the entire surface of the polyimide film and those formed on a portion of the polyimide film.
- the present invention may proceed to step (d) immediately after step (c), or after forming at least one layer selected from a conductor layer and a semiconductor layer in step (c), the device structure may be further formed. After the formation, the process may proceed to step (d).
- TFT liquid crystal display device When manufacturing a TFT liquid crystal display device as a flexible device, for example, metal wiring, TFTs made of amorphous silicon or polysilicon, and transparent pixel electrodes are formed on a polyimide film on which an inorganic film is formed on the entire surface if necessary.
- a TFT includes, for example, a gate metal layer, a semiconductor layer such as an amorphous silicon film, a gate insulating layer, a wiring connected to a pixel electrode, and the like.
- structures necessary for a liquid crystal display can also be formed by known methods.
- a transparent electrode and a color filter may be formed on the polyimide film.
- a TFT is formed as necessary on a polyimide film on which an inorganic film is formed on the entire surface, if necessary. can do.
- the polyimide film preferred in the present invention has excellent properties such as heat resistance and toughness, there are no particular restrictions on the method of forming circuits, elements, and other structures necessary for devices.
- the peeling method may be a mechanical peeling method in which physical peeling is performed by applying external force, but since the polyimide film/substrate laminate of the present invention has excellent adhesion, it can be peeled by irradiating laser light from the substrate surface. It is particularly preferable to perform the peeling by a so-called laser peeling method.
- structures or parts necessary for the device are further formed or incorporated into the (semi-)product using the polyimide film as the substrate to complete the device.
- the polyimide film is peeled off, and a conductive layer is formed on the polyimide film as in the above step (c). It is also possible to manufacture a (semi-)product using a polyimide film as a substrate by forming at least one layer selected from semiconductor layers and a necessary structure.
- polyimide film/base material laminate As described above is produced from the polyimide precursor composition of the present invention, it is particularly preferably used for this purpose because it has excellent adhesion between the polyimide film and the base material.
- the polyimide film produced from the polyimide precursor composition of the present invention has excellent light transmittance, thermal properties, and heat resistance, as well as excellent adhesion to substrates such as glass substrates.
- Adhesion can be evaluated by peel strength.
- the peel strength between the polyimide film and the base material in the polyimide film/base material laminate is preferably 20 gf/cm when measured in accordance with JIS K6854-1, for example, in a 90° peel test at a tensile rate of 2 mm/min. (0.196 N/cm) or more, more preferably 22 gf/cm (0.216 N/cm) or more. Further, the upper limit is usually 1 kgf/cm or less, preferably 800 gf/cm or less. Peel strength is usually measured in air or atmosphere.
- the monomer composition of the present invention had poor adhesion (low peel strength), it was found that the peel strength was improved by adding an imidazole compound.
- compositions containing an alicyclic monomer as the main component as the tetracarboxylic acid component do not have the problem of poor adhesion (low peel strength), and when an imidazole compound is added, the peel strength actually decreases.
- the tetracarboxylic acid component is aromatic, if the composition is outside the scope of the present invention, there are cases in which the peel strength is not improved even when an imidazole compound is added.
- the 450 nm light transmittance of the polyimide film is preferably 80% or more, more preferably 81% or more, and even more preferably 83% or more, when measured with a 10 ⁇ m thick film.
- the yellowness index (YI) of the polyimide film is preferably 9.0 or less, more preferably 8.5 or less, even more preferably 8.0 or less, and even more preferably It is 7.5 or less, even more preferably 7.0 or less, and most preferably 6.0 or less.
- the polyimide film of the present invention has an extremely low coefficient of linear thermal expansion.
- the coefficient of linear thermal expansion (CTE) of the polyimide film from 150°C to 250°C is preferably 25 ppm/K or less, more preferably 20 ppm/K when measured on a 10 ⁇ m thick film. It is still more preferably less than 20 ppm, even more preferably 15 ppm/K or less, even more preferably 11 ppm/K or less, and most preferably 10 ppm/K or less.
- the polyimide film of the present invention (or the polyimide constituting it) has excellent heat resistance, and the temperature at which it loses weight by 1% is preferably 520°C or higher, more preferably 530°C or higher, and even more preferably 540°C or higher. .
- the glass transition temperature (Tg) of the polyimide film is preferably 350°C or higher, more preferably 370°C or higher, even more preferably 390°C or higher, and The temperature is more preferably 400°C or higher, even more preferably 410°C or higher, even more preferably 420°C or higher, even more preferably 430°C or higher, even more preferably 435°C or higher, and most preferably 440°C or higher.
- the elongation at break of the polyimide film is preferably 4% or more, more preferably 7% or more when measured on a 10 ⁇ m thick film.
- the breaking strength of the polyimide film is preferably 150 MPa or more, more preferably 170 MPa or more, even more preferably 180 MPa or more, even more preferably 200 MPa or more, and even more preferably 210 MPa or more. It is.
- the breaking strength a value obtained from a film having a thickness of about 5 to 100 ⁇ m, for example, can be used.
- the adhesion, light transmittance, coefficient of linear thermal expansion, and 1% weight loss temperature be satisfied at the same time.
- polyimide and single polyimide films can also be produced using the polyimide precursor composition of the present invention.
- the manufacturing method is not particularly limited, and any known imidization method can be suitably applied.
- Preferred forms of the polyimide obtained include films, coatings, powders, beads, molded bodies, and foamed bodies.
- a single polyimide film can be manufactured by a known method.
- a typical method is to cast a polyimide precursor composition onto a substrate, heat imidize it on the substrate, and then peel off the polyimide film.
- the self-supporting film is peeled off from the base material and, for example, the film is held with a tenter and both sides of the film are exposed.
- a polyimide film can also be obtained by thermal imidization in a degassable state.
- the thickness of a single polyimide film depends on the application, but is preferably 1 ⁇ m or more, more preferably 2 ⁇ m or more, even more preferably 5 ⁇ m or more, and, for example, 250 ⁇ m or less, preferably 150 ⁇ m or less, more preferably 100 ⁇ m or less, and More preferably, it is 50 ⁇ m or less.
- the viscosity decreases after reaching the maximum viscosity, but the ratio of the viscosity 14 days after reaching the maximum viscosity to the maximum viscosity is defined as the "maximum viscosity retention rate".
- the case where the viscosity was less than 50% was evaluated as "x”.
- the viscosity was measured using an E-type viscometer TVE-25 manufactured by Toki Sangyo Co., Ltd. at a measurement temperature of 25°C.
- CTE Coefficient of linear thermal expansion
- Table 1-1 shows the tetracarboxylic acid component and diamine component
- Table 1-2 shows the structural formula of the imidazole compound.
- 2-phenylimidazole as an imidazole compound was dissolved in 4 times the weight of N-methyl-2-pyrrolidone to obtain a homogeneous solution with a solid concentration of 2-phenylimidazole of 20% by weight.
- a solution of the imidazole compound and the polyimide precursor solution synthesized above were mixed so that the amount of the imidazole compound was 0.5 mol per mol of the repeating unit of the polyimide precursor, and the mixture was stirred at room temperature for 3 hours. A uniform and viscous polyimide precursor composition was obtained.
- polyimide film/base material laminate As a glass substrate, a 6-inch Eagle-XG (registered trademark) manufactured by Corning (500 ⁇ m thick) was used. A polyimide precursor composition is applied onto a glass substrate using a spin coater, and thermally imidized by heating from room temperature to 420°C on the glass substrate in a nitrogen atmosphere (oxygen concentration 200 ppm or less) to form a polyimide film. /A base material laminate was obtained. Peel strength was measured by creating test samples with a width of 5 mm from the obtained polyimide film/glass laminate.
- the polyimide film was peeled off from the glass substrate by soaking the laminate in water at 40°C (for example, in a temperature range of 20°C to 100°C), and after drying, the properties of the polyimide film were evaluated.
- the thickness of the polyimide film is approximately 10 ⁇ m. The evaluation results are shown in Table 2.
- Examples 2 to 22 A polyimide precursor composition was prepared in the same manner as in Example 1, except that the tetracarboxylic acid component, diamine component, and imidazole compound were changed to the compounds and amounts (molar ratios) shown in Tables 2 and 3. Obtained. Thereafter, a polyimide film was produced in the same manner as in Example 1, and the physical properties of the film were evaluated.
- a polyimide precursor composition was obtained in the same manner as in Example 1, except that the tetracarboxylic acid component, diamine component, and imidazole compound were changed to the compounds and amounts (molar ratios) shown in Tables 4 to 7. Ta. Thereafter, a polyimide film was produced in the same manner as in Example 1, and the physical properties of the film were evaluated.
- eq represents the number of moles per mole of repeating unit. (Same for other tables)
- ⁇ Viscosity stabilization evaluation> The number of days for viscosity stabilization of polyimide precursor compositions having the monomer composition and the amount of imidazole compound added shown in Table 8 was evaluated. After polymerization, when the polyimide precursor composition is stored at 23° C., the viscosity increases, reaches a maximum value, and then begins to decrease. When the maximum value was reached, it was evaluated that "the viscosity was stabilized.” Table 8 shows the results.
- the present invention can be suitably applied to the production of flexible electronic devices, such as display devices such as liquid crystal displays, organic EL displays, and electronic paper, and light receiving devices such as solar cells and CMOS.
- display devices such as liquid crystal displays, organic EL displays, and electronic paper
- light receiving devices such as solar cells and CMOS.
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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JP2022007960A (ja) * | 2020-01-31 | 2022-01-13 | 宇部興産株式会社 | ポリイミド前駆体組成物およびポリイミドフィルム/基材積層体 |
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JPH10182820A (ja) * | 1996-10-29 | 1998-07-07 | Ube Ind Ltd | ポリイミド前駆体組成物及びポリイミド膜 |
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