JP6705583B2 - ポリイミド、ポリアミド酸、ポリアミド酸溶液、及び、ポリイミドフィルム - Google Patents
ポリイミド、ポリアミド酸、ポリアミド酸溶液、及び、ポリイミドフィルム Download PDFInfo
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- JP6705583B2 JP6705583B2 JP2016155589A JP2016155589A JP6705583B2 JP 6705583 B2 JP6705583 B2 JP 6705583B2 JP 2016155589 A JP2016155589 A JP 2016155589A JP 2016155589 A JP2016155589 A JP 2016155589A JP 6705583 B2 JP6705583 B2 JP 6705583B2
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- Prior art keywords
- polyimide
- repeating unit
- film
- polyamic acid
- general formula
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims description 288
- 239000004642 Polyimide Substances 0.000 title claims description 241
- 229920005575 poly(amic acid) Polymers 0.000 title claims description 138
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000000732 arylene group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- 239000010408 film Substances 0.000 description 140
- 150000001875 compounds Chemical class 0.000 description 112
- 238000000034 method Methods 0.000 description 54
- -1 heptafluoroisopropyl group Chemical group 0.000 description 53
- 238000002834 transmittance Methods 0.000 description 50
- 239000000758 substrate Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 47
- 230000000052 comparative effect Effects 0.000 description 45
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 44
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 43
- 238000011156 evaluation Methods 0.000 description 38
- 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 37
- 238000004519 manufacturing process Methods 0.000 description 31
- 238000010438 heat treatment Methods 0.000 description 30
- 238000005259 measurement Methods 0.000 description 30
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 30
- 239000002904 solvent Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 239000011521 glass Substances 0.000 description 25
- 239000010409 thin film Substances 0.000 description 23
- 238000002329 infrared spectrum Methods 0.000 description 21
- 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 18
- 150000004984 aromatic diamines Chemical class 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000009477 glass transition Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 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 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BZUNJUAMQZRJIP-UHFFFAOYSA-N CPDA Natural products OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 3
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate 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-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- GISJHCLTIVIGLX-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methoxy]pyridin-2-yl]-2-(2,6-difluorophenyl)acetamide Chemical compound FC1=CC=CC(F)=C1CC(=O)NC1=CC(OCC=2C=CC(Cl)=CC=2)=CC=N1 GISJHCLTIVIGLX-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- 230000001681 protective effect Effects 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
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- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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- 125000005562 phenanthrylene group Chemical group 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G73/1075—Partially aromatic polyimides
- C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
-
- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/1075—Partially aromatic polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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| JP2016155589A JP6705583B2 (ja) | 2016-08-08 | 2016-08-08 | ポリイミド、ポリアミド酸、ポリアミド酸溶液、及び、ポリイミドフィルム |
| TW106125449A TWI709591B (zh) | 2016-08-08 | 2017-07-28 | 聚醯亞胺、聚醯胺酸、聚醯胺酸溶液、及聚醯亞胺薄膜 |
| KR1020170098309A KR102338564B1 (ko) | 2016-08-08 | 2017-08-03 | 폴리이미드, 폴리아미드산, 폴리아미드산 용액 및 폴리이미드 필름 |
| CN201710671293.XA CN107698759B (zh) | 2016-08-08 | 2017-08-08 | 聚酰亚胺、聚酰胺酸、聚酰胺酸溶液以及聚酰亚胺膜 |
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| JP6705583B2 true JP6705583B2 (ja) | 2020-06-03 |
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| EP3330320B1 (en) * | 2015-08-07 | 2019-04-24 | Tokyo Ohka Kogyo Co., Ltd. | Polyimide precursor composition |
| JP7203082B2 (ja) * | 2018-02-21 | 2023-01-12 | Ｅｎｅｏｓ株式会社 | ポリイミド前駆体樹脂組成物 |
| KR20210007960A (ko) * | 2018-05-10 | 2021-01-20 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 폴리아미드-이미드 수지, 폴리아미드-이미드 바니시 및 폴리아미드-이미드 필름 |
| JP6503508B2 (ja) * | 2018-08-03 | 2019-04-17 | Ｊｘｔｇエネルギー株式会社 | テトラカルボン酸二無水物、ポリイミド前駆体樹脂、ポリイミド、ポリイミド前駆体樹脂溶液、ポリイミド溶液及びポリイミドフィルム |
| WO2020031932A1 (ja) * | 2018-08-07 | 2020-02-13 | 三菱ケミカル株式会社 | 光学フィルム、フィルム積層体、ディスプレイユニット |
| CN111499893B (zh) * | 2019-01-31 | 2023-12-22 | 住友化学株式会社 | 光学膜、柔性显示装置及树脂组合物 |
| KR102097431B1 (ko) * | 2019-05-13 | 2020-04-07 | 에스케이씨코오롱피아이 주식회사 | 폴리이미드 및 이의 제조 방법 |
| CN112143227A (zh) * | 2019-06-27 | 2020-12-29 | 住友化学株式会社 | 光学膜、柔性显示装置及光学膜的制造方法 |
| CN113372554B (zh) * | 2021-06-10 | 2022-08-16 | 中国科学院宁波材料技术与工程研究所 | 半脂环族聚酰亚胺及其薄膜在气体分离中的应用 |
| CN113429785B (zh) * | 2021-06-16 | 2022-05-20 | 浙江中科玖源新材料有限公司 | 一种低双折射聚酰亚胺薄膜及其制备方法 |
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| CN102906097B (zh) * | 2010-02-09 | 2015-03-04 | 吉坤日矿日石能源株式会社 | 降冰片烷-2-螺-α-环烷酮-α’-螺-2”-降冰片烷-5,5”,6,6”-四羧酸二酐类、降冰片烷-2-螺-α-环烷酮-α’-螺-2”-降冰片烷-5,5”,6,6”-四羧酸及其酯类、降冰片烷-2-螺-α-环烷酮-α’-螺-2”-降冰片烷-5,5”,6,6”-四羧酸二酐类的制造 |
| KR20150021527A (ko) * | 2012-05-28 | 2015-03-02 | 우베 고산 가부시키가이샤 | 폴리이미드 전구체 및 폴리이미드 |
| WO2014038714A1 (ja) * | 2012-09-10 | 2014-03-13 | 宇部興産株式会社 | ポリイミド前駆体、ポリイミド、ワニス、ポリイミドフィルム、および基板 |
| KR101980506B1 (ko) * | 2014-02-14 | 2019-05-20 | 아사히 가세이 가부시키가이샤 | 폴리이미드 전구체 및 그것을 함유하는 수지 조성물 |
| CN110684195B (zh) * | 2014-10-23 | 2022-09-27 | 宇部兴产株式会社 | 聚酰亚胺膜、聚酰亚胺前体和聚酰亚胺 |
| JP2016132686A (ja) * | 2015-01-15 | 2016-07-25 | Ｊｘエネルギー株式会社 | ポリイミド、ポリイミドの製造方法、ポリイミド溶液及びポリイミドフィルム |
| JP6492934B2 (ja) * | 2015-04-27 | 2019-04-03 | 宇部興産株式会社 | ポリアミック酸溶液組成物およびポリイミドフィルム |
| JP6950684B2 (ja) * | 2016-05-06 | 2021-10-13 | 三菱瓦斯化学株式会社 | ポリイミド樹脂 |
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- 2017-08-03 KR KR1020170098309A patent/KR102338564B1/ko active IP Right Grant
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| KR102338564B1 (ko) | 2021-12-14 |
| CN107698759A (zh) | 2018-02-16 |
| CN107698759B (zh) | 2021-09-28 |
| KR20180016950A (ko) | 2018-02-20 |
| JP2018024726A (ja) | 2018-02-15 |
| TW201821482A (zh) | 2018-06-16 |
| TWI709591B (zh) | 2020-11-11 |
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