JP7414013B2 - ポリイミド系樹脂フィルム、およびこれを利用したディスプレイ装置用基板ならびに光学装置 - Google Patents
ポリイミド系樹脂フィルム、およびこれを利用したディスプレイ装置用基板ならびに光学装置 Download PDFInfo
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- JP7414013B2 JP7414013B2 JP2020566235A JP2020566235A JP7414013B2 JP 7414013 B2 JP7414013 B2 JP 7414013B2 JP 2020566235 A JP2020566235 A JP 2020566235A JP 2020566235 A JP2020566235 A JP 2020566235A JP 7414013 B2 JP7414013 B2 JP 7414013B2
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- polyimide resin
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- resin film
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- 229920001721 polyimide Polymers 0.000 title claims description 213
- 239000009719 polyimide resin Substances 0.000 title claims description 125
- 239000000758 substrate Substances 0.000 title claims description 60
- 230000003287 optical effect Effects 0.000 title claims description 17
- 239000000126 substance Substances 0.000 claims description 101
- 125000000524 functional group Chemical group 0.000 claims description 78
- 239000004642 Polyimide Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 28
- 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 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005567 fluorenylene group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000010408 film Substances 0.000 description 109
- -1 1-methylpentyl Chemical group 0.000 description 23
- 239000011521 glass Substances 0.000 description 22
- 239000010410 layer Substances 0.000 description 22
- 238000001723 curing Methods 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 19
- 238000005452 bending Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 238000005259 measurement Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000011342 resin composition Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000002243 precursor Substances 0.000 description 9
- 230000008859 change Effects 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 229920005575 poly(amic acid) Polymers 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 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 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052814 silicon oxide Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 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 5
- 150000004985 diamines Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FMACFWAQBPYRFO-UHFFFAOYSA-N 5-[9-(1,3-dioxo-2-benzofuran-5-yl)fluoren-9-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 FMACFWAQBPYRFO-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001709 polysilazane Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-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
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical group CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- HCDJVEYJSSTYSW-UHFFFAOYSA-N 2-propan-2-yloxyethyl acetate Chemical compound CC(C)OCCOC(C)=O HCDJVEYJSSTYSW-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 1
- LVYXPOCADCXMLP-UHFFFAOYSA-N 3-butoxy-n,n-dimethylpropanamide Chemical compound CCCCOCCC(=O)N(C)C LVYXPOCADCXMLP-UHFFFAOYSA-N 0.000 description 1
- PVKDNXFNSSLPRN-UHFFFAOYSA-N 3-ethoxy-n,n-dimethylpropanamide Chemical compound CCOCCC(=O)N(C)C PVKDNXFNSSLPRN-UHFFFAOYSA-N 0.000 description 1
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- WHZMNADTAVKJBU-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)-9H-fluoren-2-yl]phthalic acid Chemical compound C(=O)(O)C=1C=C(C=CC=1C(=O)O)C1=C(C=2CC3=CC=CC=C3C=2C=C1)C1=CC(=C(C=C1)C(=O)O)C(=O)O WHZMNADTAVKJBU-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000006001 Methyl nonyl ketone Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N Undecanal Natural products CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 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 1
- 230000005484 gravity Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Description
本出願は、2019年2月1日付の韓国特許出願第10-2019-0013486号、2019年9月30日付の韓国特許出願第10-2019-0121176号、2019年9月30日付の韓国特許出願第10-2019-0121177号、2019年9月30日付の韓国特許出願第10-2019-0121178号、2019年12月6日付の韓国特許出願第10-2019-0161494号、および2019年12月6日付の韓国特許出願第10-2019-0161495号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
[化学式1]
[化学式2]
2)4n+2個の電子は平面形態異性体を構成しなければならないし、環構造をなさなければならない。
3)環のすべての原子がコンジュゲーションに参加しなければならない。
本発明の一実施形態によれば、前記化学式1で表されるポリイミド繰り返し単位を含むポリイミド系樹脂を含み、Bowが40μm以下であるポリイミド系樹脂フィルムが提供され得る。
[化学式3]
[化学式4]
[化学式5]
[化学式6]
[化学式6-1]
[化学式5-1]
[化学式5-2]
[化学式5-3]
Bow=(基材フィルムおよび前記基材フィルム上にコーティングされたポリイミド系樹脂フィルムを含む積層体に対するBow)-(基材フィルムのBow)
Bow変化量(μm)=Bowf-Bow
Bowf=(追加の熱処理後に基材フィルムおよび前記基材フィルム上にコーティングされたポリイミド系樹脂フィルムを含む積層体に対するBow)-(基材フィルムのBow)
また、本発明のさらに他の実施形態によれば、前記他の実施形態のポリイミド系樹脂フィルムを含むディスプレイ装置用基板が提供される。前記ポリイミド系樹脂フィルムに関する内容は前記一実施形態で上述した内容を全て含み得る。
また、本発明のさらに他の実施形態によれば、前記他の実施形態のポリイミド系樹脂フィルムを含む光学装置が提供される。前記ポリイミド系樹脂フィルムに関する内容は前記一実施形態で上述した内容を全て含み得る。
窒素気流が流れる攪拌機内に有機溶媒DEAcを満たした後、反応器の温度を25℃に維持した状態で下記化学式aで表されるジアミン0.735molを同じ温度で添加して溶解させた。下記化学式aで表されるジアミンが添加された溶液に、酸二無水物として下記化学式bで表される9,9-ビス(3,4-ジカルボキシフェニル)フルオレン二無水物(9,9-Bis(3,4-dicarboxyphenyl)fluorene Dianhydride、BPAF)0.3675molおよび3,3',4,4'-ビフェニルテトラカルボン酸二無水物(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)0.3675molを同じ温度で添加して24時間攪拌して、ポリイミド前駆体組成物を得た。
[化学式a]
前記ポリイミド前駆体組成物をガラス基板上にスピンコーティングした。ポリイミド前駆体組成物が塗布されたガラス基板をオーブンに入れて5℃/minの速度で加熱し、80℃で20分、450℃で70分を維持して硬化工程を行い、ポリイミドフィルム(厚さ:10μm)を製造した。
酸二無水物として、3,3',4,4'-ビフェニルテトラカルボン酸二無水物(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)の代わりに4,4'-(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(4,4'-(Hexafluoroisopropylidene)diphthalic anhydride、6-FDA)を使用したことを除いては、前記実施例1と同様の方法でポリイミドフィルムを製造した。
酸二無水物として、3,3',4,4'-ビフェニルテトラカルボン酸二無水物(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)の代わりにピロメリット酸無水物(pyromellitic dianhydride、PMDA)を使用したことを除いては、前記実施例1と同様の方法でポリイミドフィルムを製造した。
窒素気流が流れる攪拌機内に有機溶媒DEAcを満たした後、反応器の温度を25℃に維持した状態で2,2'-ビス(トリフルオロメチル)ベンジジン)(2,2'-bis(trifluoromethyl)benzidine)、TFMB)0.735molを同じ温度で添加して溶解させた。2,2'-ビス(トリフルオロメチル)ベンジジン)(2,2'-bis(trifluoromethyl)benzidine)、TFMB)が添加された溶液に、酸二無水物として下記化学式bで表される3,3',4,4'-ビフェニルテトラカルボン酸二無水物(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)0.735molを同じ温度で添加して24時間攪拌して、ポリイミド前駆体組成物を得た。
前記ポリイミド前駆体組成物をガラス基板上にスピンコーティングした。ポリイミド前駆体組成物が塗布されたガラス基板をオーブンに入れて5℃/minの速度で加熱し、80℃で20分、450℃で70分を維持して硬化工程を行い、ポリイミドフィルム(厚さ:10μm)を製造した。
酸二無水物として、3,3',4,4'-ビフェニルテトラカルボン酸二無水物(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)0.3675mol、4,4'-(ヘキサフルオロイソプロピリデン)ジフタル酸無水物(4,4'-(Hexafluoroisopropylidene)diphthalic anhydride、6-FDA)0.3675molを添加したことを除いては、前記比較例1と同様の方法でポリイミドフィルムを製造した。
前記実施例および比較例で得られたポリイミドフィルムから物性を下記方法で測定し、その結果を表1および表2に示す。
実施例および比較例で得られたガラス基板上にコーティングされたポリイミドフィルム積層体(ガラス基板+ポリイミドフィルム)に対するBow値と、ガラス基板のみのBow値を測定して、下記数式によってポリイミドフィルムのBow(曲げ)を計算して下記表1に記載した。
ポリイミドフィルムのBow(曲げ)=(ガラス基板上にコーティングされたポリイミドフィルム積層体に対するBow)-(ガラス基板のみのBow)
実施例および比較例で得られたガラス基板上にコーティングされたポリイミドフィルム積層体(ガラス基板+ポリイミドフィルム)を410℃で60分間さらに硬化した後、445℃で60分間さらに硬化した後に測定したBow値と、ガラス基板のみのBow値を測定して、下記数式によってポリイミドフィルムの最終曲げ(Bowf)を求め、これを利用して下記数式によってポリイミドフィルムのBow変化量(△Bow)を計算して下記表1の耐熱曲げ(△Bow)に記載した。Bow測定方法は、前記実験例1と同様である。
実施例および比較例で得られたガラス基板上にコーティングされたポリイミドフィルム積層体(ガラス基板+ポリイミドフィルム)を445℃で20分間さらに硬化した後、410℃で60分間さらに硬化した後に測定したBow値と、ガラス基板のみのBow値を測定して、下記数式によってポリイミドフィルムの最終曲げ(Bowf)を求め、これを利用して下記数式によってポリイミドフィルムのBow変化量(△Bow)を計算して下記表1の耐熱曲げ(△Bow)に記載した。Bow測定方法は、前記実験例1と同様である。
実施例および比較例で得られたガラス基板上にコーティングされたポリイミドフィルム積層体(ガラス基板+ポリイミドフィルム)を445℃で20分間さらに硬化した後、445℃で20分間さらに硬化した後、410℃で60分間さらに硬化した後、445℃で60分間硬化した後に測定したBow値と、ガラス基板のみのBow値を測定して、下記数式によってポリイミドフィルムの最終曲げ(Bowf)を求め、これを利用して下記数式によってポリイミドフィルムのBow変化量(△Bow)を計算して下記表1の耐熱曲げ(△Bow)に記載した。Bow測定方法は、前記実験例1と同様である。
ポリイミドフィルムの最終曲げ(Bowf)=(追加の熱処理後にガラス基板上にコーティングされたポリイミドフィルム積層体に対するBow)-(ガラス基板のBow)
ポリイミドフィルムのBow変化量(△Bow)=(実験例2で得られたポリイミドフィルムの最終曲げ(Bowf))-(実験例1で得られたポリイミドフィルムの曲げ(Bow))
2 基準面(reference plane(Best fit plane of thickness central plane))
3 中心軸
4 Bow
Claims (17)
- 下記化学式1で表されるポリイミド繰り返し単位を含むポリイミド系樹脂を含み、
Bowが40μm以下である、ポリイミド系樹脂フィルム:
[化学式1]
X1は下記化学式2で表される4価の官能基であり、
Y1は電子求引性基が少なくとも1以上置換された炭素数15以上の芳香族2価官能基であり、
[化学式2]
前記化学式2のAr中、多環芳香族2価官能基はフルオレニレン基を含み、
前記Y 1 の電子求引性基が少なくとも1以上置換された炭素数15以上の芳香族2価官能基は、下記化学式3で表される官能基を含み、
[化学式3]
T 1 ~T 3 は互いに同一または異なり、それぞれ独立して電子求引性基であり、
m1~m3は互いに同一または異なり、m1~m3のうちの少なくとも一つは1~4の整数であり、残りは0~4の整数であり、
nは1~10の整数である。 - 下記数式1によって得られる前記ポリイミド系樹脂フィルムのBow変化量が5μm以下である、請求項1に記載のポリイミド系樹脂フィルム:
[数式1]
Bow変化量(μm)=Bowf-Bow
前記数式1中、
Bowfは、前記ポリイミド系樹脂フィルムを400℃~450℃の温度で50分~200分間さらに熱処理した後に得られるフィルムの最終Bow値であり、
Bowは、前記ポリイミド系樹脂フィルムのBow値である。 - 前記Bowは、ポリイミド系樹脂フィルムの厚さ中心面と基準面の間の中心軸上の距離で定義される、請求項1または2に記載のポリイミド系樹脂フィルム。
- 前記Bowは、5μm以上30μm以下の厚さを有するポリイミド系樹脂フィルム試料に対して測定される、請求項1から3のいずれか一項に記載のポリイミド系樹脂フィルム。
- 前記Bowは下記数式2によって得られる、請求項1から4のいずれか一項に記載のポリイミド系樹脂フィルム:
[数式2]
Bow=(基材フィルムおよび前記基材フィルム上にコーティングされたポリイミド系樹脂フィルムを含む積層体に対するBow)-(基材フィルムのBow) - 前記化学式2のAr中、多環芳香族2価官能基は、
少なくとも2以上の芳香族環化合物が含まれている縮環型2価の官能基を含む、請求項1から5のいずれか一項に記載のポリイミド系樹脂フィルム。 - 前記化学式2で表される4価の官能基は、下記化学式2-1で表される官能基を含む、請求項1から6のいずれか一項に記載のポリイミド系樹脂フィルム:
[化学式2-1]
- 前記Y1中の炭素数15以上の芳香族2価官能基は芳香族環化合物を3個以上含む、請求項1から7のいずれか一項に記載のポリイミド系樹脂フィルム。
- 前記炭素数15以上の芳香族2価官能基はトリフェニレン基、クォーターフェニレン基、およびペンタフェニレン基からなる群より選択される1種以上を含む、請求項8に記載のポリイミド系樹脂フィルム。
- 前記電子求引性基はハロアルキル基、ハロゲン基、シアノ基、ニトロ基、スルホン酸基、カルボニル基およびスルホニル基からなる群より選択される1種以上を含む、請求項1から9のいずれか一項に記載のポリイミド系樹脂フィルム。
- 前記Y1の電子求引性基が少なくとも1以上置換された炭素数15以上の芳香族2価官能基は、下記化学式3-1で表される官能基を含む、請求項1から10のいずれか一項に記載のポリイミド系樹脂フィルム:
[化学式3-1]
- 前記ポリイミド系樹脂は、下記化学式4で表されるテトラカルボン酸二無水物および電子求引性基が少なくとも1以上置換された炭素数15以上の芳香族ジアミンの結合物を含む、請求項1から11のいずれか一項に記載のポリイミド系樹脂フィルム:
[化学式4]
- 前記ポリイミド系樹脂は、下記化学式5で表されるポリイミド繰り返し単位をさらに含む、請求項1から12のいずれか一項に記載のポリイミド系樹脂フィルム:
[化学式5]
X2は下記化学式6で表される4価の官能基のうちの一つであり、
Y2は電子求引性基が少なくとも1以上置換された炭素数15以上の芳香族2価官能基であり、
[化学式6]
- 前記化学式5で表されるポリイミド繰り返し単位と化学式1で表されるポリイミド繰り返し単位は、ポリイミド系樹脂に含まれている全繰り返し単位に対して70モル%以上含まれる、請求項13に記載のポリイミド系樹脂フィルム。
- 前記ポリイミド系樹脂フィルムは、前記ポリイミド系樹脂が400℃以上の温度で硬化した硬化物を含む、請求項1から14のいずれか一項に記載のポリイミド系樹脂フィルム。
- 請求項1から15のいずれか一項に記載のポリイミド系樹脂フィルムを含む、ディスプレイ装置用基板。
- 請求項1から15のいずれか一項に記載のポリイミド系樹脂フィルムを含む、光学装置。
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JP2019503412A (ja) | 2016-09-23 | 2019-02-07 | エルジー・ケム・リミテッド | ポリイミド前駆体溶液及びその製造方法 |
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US20210230368A1 (en) | 2021-07-29 |
US20210214501A1 (en) | 2021-07-15 |
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JP2022518985A (ja) | 2022-03-18 |
US20210206921A1 (en) | 2021-07-08 |
TW202035523A (zh) | 2020-10-01 |
JP2022518984A (ja) | 2022-03-18 |
JP7414010B2 (ja) | 2024-01-16 |
TWI747146B (zh) | 2021-11-21 |
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