JP6894245B2 - 成形品製造用組成物、前記組成物から得られる成形品、および前記成形品を含むディスプレイ装置 - Google Patents
成形品製造用組成物、前記組成物から得られる成形品、および前記成形品を含むディスプレイ装置 Download PDFInfo
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- JP6894245B2 JP6894245B2 JP2017013479A JP2017013479A JP6894245B2 JP 6894245 B2 JP6894245 B2 JP 6894245B2 JP 2017013479 A JP2017013479 A JP 2017013479A JP 2017013479 A JP2017013479 A JP 2017013479A JP 6894245 B2 JP6894245 B2 JP 6894245B2
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- 239000000203 mixture Substances 0.000 title claims description 61
- 239000000126 substance Substances 0.000 claims description 127
- 229910052751 metal Inorganic materials 0.000 claims description 92
- 239000002184 metal Substances 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 75
- 229920001577 copolymer Polymers 0.000 claims description 62
- -1 Halogen ion Chemical class 0.000 claims description 30
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 101710134784 Agnoprotein Proteins 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 239000004262 Ethyl gallate Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001768 cations Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000005567 fluorenylene group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 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 43
- 150000001408 amides Chemical class 0.000 description 23
- 239000000047 product Substances 0.000 description 22
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- 150000003949 imides Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 14
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- 239000002253 acid Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 10
- 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 7
- 230000009975 flexible effect Effects 0.000 description 7
- 238000002834 transmittance Methods 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
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 229920005575 poly(amic acid) Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- GNIZQCLFRCBEGE-UHFFFAOYSA-N 3-phenylbenzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(Cl)=O GNIZQCLFRCBEGE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- XMXCPDQUXVZBGQ-UHFFFAOYSA-N 2,3,6,7-tetrachloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound ClC1=C(Cl)C(C(O)=O)=C2C(C(=O)O)=C(Cl)C(Cl)=C(C(O)=O)C2=C1C(O)=O XMXCPDQUXVZBGQ-UHFFFAOYSA-N 0.000 description 1
- SDWGBHZZXPDKDZ-UHFFFAOYSA-N 2,6-dichloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=C(Cl)C(C(O)=O)=C2C(C(=O)O)=CC(Cl)=C(C(O)=O)C2=C1C(O)=O SDWGBHZZXPDKDZ-UHFFFAOYSA-N 0.000 description 1
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- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 1
- QQHCDNARIZUFGB-UHFFFAOYSA-N 2-fluorobenzene-1,4-dicarbonyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC=C1C(Cl)=O QQHCDNARIZUFGB-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- SMDGQEQWSSYZKX-UHFFFAOYSA-N 3-(2,3-dicarboxyphenoxy)phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O SMDGQEQWSSYZKX-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- NDXGRHCEHPFUSU-UHFFFAOYSA-N 3-(3-aminophenyl)aniline Chemical group NC1=CC=CC(C=2C=C(N)C=CC=2)=C1 NDXGRHCEHPFUSU-UHFFFAOYSA-N 0.000 description 1
- UCFMKTNJZCYBBJ-UHFFFAOYSA-N 3-[1-(2,3-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)C1=CC=CC(C(O)=O)=C1C(O)=O UCFMKTNJZCYBBJ-UHFFFAOYSA-N 0.000 description 1
- KHDSXXRHWXXXBY-UHFFFAOYSA-N 3-[4-(2,3-dicarboxyphenoxy)phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O KHDSXXRHWXXXBY-UHFFFAOYSA-N 0.000 description 1
- VILWHDNLOJCHNJ-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfanylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1SC1=CC=C(C(O)=O)C(C(O)=O)=C1 VILWHDNLOJCHNJ-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- PTWQVOITXCIGEB-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)-2,2,2-trifluoro-1-phenylethyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C=1C=C(C(C(O)=O)=CC=1)C(O)=O)C1=CC=CC=C1 PTWQVOITXCIGEB-UHFFFAOYSA-N 0.000 description 1
- IJJNNSUCZDJDLP-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJJNNSUCZDJDLP-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 description 1
- YQRHQSXYASUCQL-UHFFFAOYSA-N 4-[3-(3,4-dicarboxyphenyl)-1,1,2,2,3,3-hexafluoropropyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(F)(F)C(F)(F)C(F)(F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 YQRHQSXYASUCQL-UHFFFAOYSA-N 0.000 description 1
- NJWZAJNQKJUEKC-UHFFFAOYSA-N 4-[4-[2-[4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C=1C=C(OC=2C=3C(=O)OC(=O)C=3C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC2=C1C(=O)OC2=O NJWZAJNQKJUEKC-UHFFFAOYSA-N 0.000 description 1
- GAUNIEOSKKZOPV-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)benzoyl]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C=C(C(C(O)=O)=CC=3)C(O)=O)=CC=2)C=C1 GAUNIEOSKKZOPV-UHFFFAOYSA-N 0.000 description 1
- MRTAEHMRKDVKMS-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)phenyl]sulfanylphenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 MRTAEHMRKDVKMS-UHFFFAOYSA-N 0.000 description 1
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- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 1
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- RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 1
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- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- LUEGQDUCMILDOJ-UHFFFAOYSA-N thiophene-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C=1SC(C(O)=O)=C(C(O)=O)C=1C(O)=O LUEGQDUCMILDOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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- Manufacture Of Macromolecular Shaped Articles (AREA)
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Description
Dは、置換もしくは非置換の4価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基、または置換もしくは非置換の4価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、前記芳香族環基、または前記ヘテロ芳香族環基は単環、縮合環(2個以上の環が互いに縮合して形成されたものを指し、以下同様)、または2個以上の前記単環もしくは単独縮合環が単結合、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10脂肪族炭化水素基、6〜C20芳香族炭化水素基、またはC6〜C20脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されてなるものであり、
Eは、電子吸引基(electronwithdrawing group)で置換されたまたは非置換のビフェニレン(biphenylene)基である。
Aは、置換もしくは非置換の2価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基または置換もしくは非置換の2価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、芳香族環基、またはヘテロ芳香族環基は、単独で存在するか、または2つ以上の環が互いに接合して縮合環を形成するか、または前記単独で存在するか互いに接合して縮合環を形成した2以上が単結合、フルオレニレン基、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10炭化水素基、C6〜C20芳香族炭化水素基、またはC6〜C20脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されており、
Bは、電子吸引基(electronwithdrawing group)で置換されたまたは非置換のビフェニレン(biphenylene)基である。
Z1およびZ2は、それぞれ同一であるか異なり、独立して−N=または−C(R100)=であって、R100は水素またはC1〜C5アルキル基であり、Z1およびZ2が同時に−C(R100)=ではなく、
Z3は、−O−、−S−、または−N(R101)−であり、R101は水素またはC1〜C5アルキル基である。
R18〜R29は、同一であるか互いに異なり、それぞれ独立して重水素、ハロゲン、置換もしくは非置換のC1〜C10脂肪族有機基、または置換もしくは非置換のC6〜C20芳香族有機基であり、
n11およびn14〜n20は、それぞれ独立して0〜4の整数であり、
n12およびn13は、それぞれ独立して0〜3の整数である。
Dは、置換もしくは非置換の4価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基、または置換もしくは非置換の4価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、前記芳香族環基、または前記ヘテロ芳香族環基は単環、縮合環、または2個以上の前記単環もしくは縮合環が単結合、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10脂肪族炭化水素基、C6〜20芳香族炭化水素基、またはC6〜C20脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されてなるものであり、
Eは、電子吸引基で置換されたまたは非置換のビフェニレン基である。
Aは、それぞれ独立して置換もしくは非置換の2価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基または置換もしくは非置換の2価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、芳香族環基、またはヘテロ芳香族環基は、単環、縮合環、または2個以上の前記単環もしくは縮合環が単結合、フルオレニレン基、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10脂肪族炭化水素基、C6〜C20芳香族炭化水素基、またはC6〜C20脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されてなるものであり、
Bは、電子吸引基で置換されたまたは非置換のビフェニレン基である。
前記組成物で、イミド構造単位およびアミド酸構造単位を示す前記化学式1および化学式2のDは、下記グループ1の化学式から選択されてもよい。
Z1およびZ2は、それぞれ同一であるか異なり、独立して−N=または−C(R100)=であって、R100は水素またはC1〜C5アルキル基であり、Z1およびZ2が同時に−C(R100)=ではなく、
Z3は、−O−、−S−、または−N(R101)−であり、R101は水素またはC1〜C5アルキル基である。
R18〜R29は、同一であるか互いに異なり、それぞれ独立して重水素、ハロゲン、置換もしくは非置換のC1〜C10脂肪族有機基、または置換もしくは非置換のC6〜C20芳香族有機基であり、
n11およびn14〜n20は、それぞれ独立して0〜4の整数(好ましくは0〜2の整数)であり、
n12およびn13はそれぞれ独立して0〜3の整数である。
窒素雰囲気下で、反応器に8169gのN,N−ジメチルアセトアミドを入れ、ピリジン276gを投入する。前記反応器に2,2’−ビス(トリフルオロメチル)ベンジジン(TFDB)400gを入れて溶解させてTFDB溶液を製造する。前記TFDB溶液にテレフタロイルクロライド(TPCL)178gを添加し、30℃で3時間攪拌してアミドオリゴマー溶液を得る。得られた溶液は水を利用して沈澱を起こした後、80℃で48時間乾燥してアミドオリゴマーパウダを得る。前記で製造されたアミドオリゴマーパウダ59.2gと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(6FDA)9.55gおよび3,3’,4,4’−ビフェニルテトラカルボン酸二無水物(BPDA)6.33gをN,N−ジメチルアセトアミド425gに添加し、30℃で48時間反応を行いポリ(アミド酸−アミド)コポリマー溶液を得る。
合成例1で製造されたポリ(イミド−アミド)コポリマー溶液に、前記コポリマーの重量および添加される金属塩の重量の和を基準に下記表1に記載された含有量で金属塩LiClを添加した溶液を製造する。具体的には、N,N−ジメチルアセトアミドにLiClを溶解させて1重量%溶液を製造し、この溶液を前記ポリ(イミド−アミド)コポリマーが含まれている溶液に下記表1に記載された含有量になるようにそれぞれ添加して24時間攪拌することにより、実施例1〜実施例3によるポリ(イミド−アミド)コポリマーとLiClを含む溶液を得る。このとき、溶液内に含まれているLiイオンの含有量は下記表1にppm単位で表した。
Micrometer(ミツトヨ社)を利用して厚さを測定する。
インストロン(Instron)装備を利用してASTM D882により測定する。幅1cm、長さ5cmのフィルム試片を準備し、常温で延伸速度50mm/minで測定する。
UV分光計(Spectrophotometer、コニカミノルタ社、cm−3600d)を利用してASTM E313規格で測定する。
フィルムをUVB波長領域の紫外線ランプに72時間露出した(200mJ/cm2以上)前後の黄色度値(UV照射後、−UV照射前)の差ΔYIを測定する。
金属塩を含まない点を除いては前記実施例1〜実施例3と同様の方法により、合成例1で製造されたポリ(イミド−アミド)コポリマー溶液を使用してフィルムを製造し、製造されたフィルムの引張弾性率、黄色度(YI)、ΔYI、および全光線(370nm〜740nm)透過率を測定して下記表1に記載する。
金属塩の含有量を異なるようにした点を除いては実施例1〜実施例3と同様の方法により、ポリ(アミド−イミド)コポリマーおよび金属塩(LiCl)を含む比較例2および比較例3によるフィルムを製造し、製造されたフィルムの引張弾性率、黄色度(YI)、ΔYI、および全光線(370nm〜740nm)透過率を測定して下記表1に記載する。
Claims (20)
- (1)(i)下記化学式1で表される構造単位および下記化学式2で表される構造単位のうち一つ以上を含むポリマーならびに(ii)下記化学式1で表される構造単位および下記化学式2で表される構造単位のうち一つ以上と、下記化学式3で表される構造単位と、を含むコポリマーのうち一つ以上を含む溶液と、
(2)前記溶液に溶解する金属塩(この際、前記金属は1族、11族、13族、または14族に属する金属から選択される)と、
を含み、
前記金属塩は、前記組成物内の前記ポリマーおよびコポリマーのうち一つ以上の重量と前記金属塩の重量との和を基準に2.5重量%未満で含まれる、成形品製造用組成物:
前記化学式1および化学式2において、
Dは、置換もしくは非置換の4価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基、または置換もしくは非置換の4価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、前記芳香族環基、または前記ヘテロ芳香族環基は単環、縮合環、または2個以上の前記単環もしくは縮合環が単結合、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して、水素、C1〜C10脂肪族炭化水素基、C6〜C20芳香族炭化水素基、またはC6〜C20脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されてなるものであり、
Eは、電子吸引基(electronwithdrawing group)で置換されたまたは非置換のビフェニレン(biphenylene)基である。
前記化学式3において、
Aは、それぞれ独立して置換もしくは非置換の2価のC6〜C24脂肪族環基、置換もしくは非置換のC6〜C24芳香族環基または置換もしくは非置換の2価のC4〜C24ヘテロ芳香族環基であり、前記脂肪族環基、芳香族環基、またはヘテロ芳香族環基は単環、縮合環、または2個以上の前記単環もしくは縮合環が単結合、フルオレニレン基、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、−(CF2)q−(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10の脂肪族炭化水素基、C6〜C20の芳香族炭化水素基、またはC6〜C20の脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−により連結されてなるものであり、
Bは、電子吸引基(electronwithdrawing group)で置換されたまたは非置換のビフェニレン(biphenylene)基である。 - 前記金属は、リチウム(Li)、ナトリウム(Na)、アルミニウム(Al)、銀(Ag)、および錫(Sn)からなる群より選択され、かつ、前記金属塩は、前記金属の陽イオンと、ハロゲンイオン、アセチルアセトネートイオン、ClO−、SO4 2−、PO4
3−、およびNO3 −からなる群より選択される陰イオンと、を含む、請求項1に記載の組成物。 - 前記金属塩は、LiCl、NaCl、AgBr、AgNO3、SnCl2、およびアルミニウムアセチルアセトネートからなる群より選択される一つ以上である、請求項1または2に記載の組成物。
- 前記金属塩は、前記組成物内の前記ポリマーおよびコポリマーのうち一つ以上の重量と前記金属塩の重量との和を基準に0.1重量%〜2重量%で含まれる、請求項1〜3のいずれか1項に記載の組成物。
- 前記化学式1および前記化学式2のDは、それぞれ独立して下記グループ1の化学式から選択されるものである、請求項1〜4のいずれか1項に記載の組成物:
上記式において、それぞれの残基は、置換もしくは非置換のものであり、それぞれのLは、同一であるか異なり、それぞれ独立して単結合、−O−、−S−、−C(=O)−、−CH(OH)−、−S(=O)2−、−Si(CH3)2−、−(CH2)p−(この際、1≦p≦10)、(CF2)q(この際、1≦q≦10)、−CR’R”−(この際、R’およびR”は、それぞれ独立して水素、C1〜C10の脂肪族炭化水素基、C6〜C20の芳香族炭化水素基、C6〜C20の脂環族炭化水素基であり、この際R’およびR”は同時に水素ではない)、−C(CF3)2−、−C(CF3)(C6H5)−、または−C(=O)NH−であり、*は隣接した原子に連結される部分であり、
Z1およびZ2は、それぞれ同一であるか異なり、独立して−N=または−C(R100)=であって、R100は水素またはC1〜C5アルキル基であり、Z1およびZ2が
同時に−C(R100)=ではなく、
Z3は、−O−、−S−、または−N(R101)−であり、R101は水素、またはC1〜C5アルキル基である。 - 前記化学式1および前記化学式2のEは、それぞれのフェニレン基が−CF3、−CCl3、−CBr3、−CI3、−F、−Cl、−Br、−I、−NO2、−CN、−COCH3または−CO2C2H5からなる群より選択される電子吸引基で置換されたビフェニレン基である、請求項1〜7のいずれか1項に記載の組成物。
- 前記化学式3のBは、それぞれのフェニレン基が−CF3、−CCl3、−CBr3、−CI3、−F、−Cl、−Br、−I、−NO2、−CN、−COCH3または−CO2C2H5からなる群より選択される電子吸引基で置換されたビフェニレン基である、請求項1〜10のいずれか1項に記載の組成物。
- 前記コポリマーにおいて、前記化学式4で表される構造単位の含有量および前記化学式5で表される構造単位の含有量の和と、前記化学式6で表される構造単位の含有量とのモル比は、20:80〜50:50である、請求項14に記載の組成物。
- 前記金属塩は、前記コポリマーの重量と前記金属塩の重量との和を基準に0.1重量%〜2.0重量%含まれる、請求項14または15に記載の組成物。
- 請求項1〜16のいずれか1項に記載の組成物から製造される成形品。
- 前記成形品はフィルムであり、UV分光計(Spectrophotometer、コニカミノルタ社、cm−3600d)を利用してASTM E313で測定した黄色指数(YI:Yellowness Index)が3.5未満であり、ASTM D882で測定した引張弾性率は6.7GPa超である、請求項17に記載の成形品。
- 前記フィルムの厚さは、10μm〜100μmである、請求項18に記載の成形品。
- 請求項17〜19のいずれか1項に記載の成形品を含む、ディスプレイ装置。
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US10689513B2 (en) | 2020-06-23 |
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