JP7444851B2 - 電子デバイスで使用するためのポリマー - Google Patents
電子デバイスで使用するためのポリマー Download PDFInfo
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- JP7444851B2 JP7444851B2 JP2021506713A JP2021506713A JP7444851B2 JP 7444851 B2 JP7444851 B2 JP 7444851B2 JP 2021506713 A JP2021506713 A JP 2021506713A JP 2021506713 A JP2021506713 A JP 2021506713A JP 7444851 B2 JP7444851 B2 JP 7444851B2
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- polyamic acid
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- 229920000642 polymer Polymers 0.000 title description 26
- 229920005575 poly(amic acid) Polymers 0.000 claims description 114
- 239000000758 substrate Substances 0.000 claims description 114
- 229920001721 polyimide Polymers 0.000 claims description 96
- 239000000203 mixture Substances 0.000 claims description 49
- 239000007788 liquid Substances 0.000 claims description 34
- 239000004642 Polyimide Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 238000009835 boiling Methods 0.000 claims description 28
- 239000000010 aprotic solvent Substances 0.000 claims description 23
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 18
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 18
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 16
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000006157 aromatic diamine group Chemical group 0.000 claims 2
- 239000013039 cover film Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 238
- 238000006243 chemical reaction Methods 0.000 description 223
- 230000008569 process Effects 0.000 description 199
- 239000010410 layer Substances 0.000 description 132
- 239000000463 material Substances 0.000 description 90
- 239000000243 solution Substances 0.000 description 87
- 239000010408 film Substances 0.000 description 41
- 239000002904 solvent Substances 0.000 description 39
- 239000002245 particle Substances 0.000 description 29
- 230000032258 transport Effects 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 239000011248 coating agent Substances 0.000 description 24
- 238000000576 coating method Methods 0.000 description 24
- -1 polyethylene terephthalate Polymers 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
- 125000004427 diamine group Chemical group 0.000 description 23
- 150000004985 diamines Chemical class 0.000 description 23
- 239000011521 glass Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 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 16
- 230000005525 hole transport Effects 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 235000012431 wafers Nutrition 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 10
- 230000008901 benefit Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229920002223 polystyrene Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 150000004984 aromatic diamines Chemical group 0.000 description 8
- 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 8
- 230000006870 function Effects 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 230000004580 weight loss Effects 0.000 description 7
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 5
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 4
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- WSLASHNMNXHPBQ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC2=C(B3OC(C)(C)C(C)(C)O3)C=CC=C12 WSLASHNMNXHPBQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical class [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IFHGSECJTKJJIJ-UHFFFAOYSA-N [5-(trifluoromethylsulfonyloxy)naphthalen-1-yl] trifluoromethanesulfonate Chemical compound C1=CC=C2C(OS(=O)(=O)C(F)(F)F)=CC=CC2=C1OS(=O)(=O)C(F)(F)F IFHGSECJTKJJIJ-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000005352 clarification Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 229920001577 copolymer Chemical group 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- OJSPYCPPVCMEBS-UHFFFAOYSA-N 2,8-dimethyl-5,5-dioxodibenzothiophene-3,7-diamine Chemical compound C12=CC(C)=C(N)C=C2S(=O)(=O)C2=C1C=C(C)C(N)=C2 OJSPYCPPVCMEBS-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- PMAPIPPKZXGDFA-UHFFFAOYSA-N 2-[(2-carboxyanilino)methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NCNC1=CC=CC=C1C(O)=O PMAPIPPKZXGDFA-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- LIIOFEJBUYPKIV-UHFFFAOYSA-N 4-[5-[4-amino-2-(trifluoromethyl)phenyl]naphthalen-1-yl]-3-(trifluoromethyl)aniline Chemical compound C1(=CC=CC2=C(C=CC=C12)C1=C(C=C(N)C=C1)C(F)(F)F)C1=C(C=C(N)C=C1)C(F)(F)F LIIOFEJBUYPKIV-UHFFFAOYSA-N 0.000 description 2
- YGNISOAUPSJDJE-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C(C(F)(F)F)=C1 YGNISOAUPSJDJE-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
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 2
- RWXZXCZBMQPOBF-UHFFFAOYSA-N 5-methyl-1H-benzimidazole Chemical compound CC1=CC=C2N=CNC2=C1 RWXZXCZBMQPOBF-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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Images
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
本出願は、参照によりその全体が本明細書に組み込まれる2018年8月7日出願の米国仮特許出願第62/715,422号明細書の利益を主張するものである。
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30~100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0~4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)。
後述の実施形態の詳細を扱う前に、いくつかの用語について定義又は明確化する。
α=(ΔL/L0)/ΔT
本明細書に開示される測定されたCTE値は、第1又は第2の加熱スキャン中に既知の方法により作成される。材料の相対膨張/収縮特性についての理解は、電子デバイスの作製及び/又は信頼性における重要な検討すべき事項である可能性がある。
本明細書に記載のポリアミド酸は、式I
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30~100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0~4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)の繰り返し単位を有する。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R3及びR4は、同一であり又は異なり、H、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
*は結合の点を示す)。
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0~4の整数であり、
c及びdは、同一であり又は異なり、1又は2である)。
ODPA//Bis-P/22TFMB 100//90/10。
(a)ジアミン成分及び二無水物成分が事前に一緒に混合され、次いで混合物が撹拌されている間に溶媒に少しずつ添加される方法。
(b)溶媒がジアミン成分及び二無水物成分の撹拌混合物に添加される方法。(上記の(a)とは反対に)
(c)ジアミンが溶媒に排他的に溶解され、次いで反応速度を制御することを可能にするような比で二無水物がそれに添加される方法。
(d)二無水物成分が溶媒に排他的に溶解され、次いで反応速度を制御することを可能にするような比でアミン成分がそれに添加される方法。
(e)ジアミン成分及び二無水物成分が溶媒に別個に溶解され、次いでこれらの溶液が反応器内で混合される方法。
(f)過剰なアミン成分を含むポリアミド酸及び過剰な二無水物成分を含む別のポリアミド酸が事前に形成され、次いで特にノンランダムコポリマー又はブロックコポリマーを作成できるような方法にて反応器内で相互に反応される方法。
(g)アミン成分及び二無水物成分の特定部分が最初に反応され、次いで残留ジアミン成分が反応される又はその逆である方法。
(h)成分が部分的に又は全体として任意の順序で溶媒の一部又は全部のいずれかに添加され、更に任意の成分の一部又は全部が溶媒の一部又は全部の溶液として添加され得る方法。
(i)二無水物成分の1つをジアミン成分の1つと最初に反応させて第1のポリアミド酸を生じさせる方法。次いで、他方の二無水物成分を他方のアミン成分と反応させると、第2のポリアミド酸が生じる。次いで、フィルム形成の前に、いくつかの方法のいずれか1つでポリアミド酸を組み合わせる。
式IVの繰り返し単位構造を有するポリイミドが提供される。
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30~100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、0~4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)。
一般的に、ポリイミドフィルムは、化学又は熱変換によってポリイミド前駆体から調製することができる。一部の実施形態では、フィルムは、化学又は熱変換プロセスによって、対応するポリアミド酸溶液から調製される。本明細書に開示されるポリイミドフィルムは、特に電子デバイスにおけるガラスの柔軟な代替物として使用される場合、熱変換プロセスによって調製される。
本明細書に開示されたポリイミドフィルムは、例えば、OLED及びLCDディスプレイ等の電子ディスプレイデバイス内のいくつかの層で使用するために好適であり得る。このような層の非限定的な例としては、デバイス基板、タッチパネル、カラーフィルターシート用基板、カバーフィルムなどが挙げられる。各用途のための特定の材料の特性要件は、固有であり、本明細書に開示されたポリイミドフィルムのための適切な組成及び加工条件によって対応することができる。
この実施例は、式III、具体的には式IIIA-1を有するジアミン:4,4’-(ナフタレン-2,6-ジイル)ビス(3-(トリフルオロメチル)アニリン)、化合物1の調製を示している。
この実施例は、式Iを有するポリアミド酸を含む液体組成物の調製を示す。ポリアミド酸は、組成物BPDA/PMDA//化合物1 97/3//100を有した。
この実施例は、式IVを有するポリイミドフィルムの調製を示している。
引張り弾性率=10.9GPa
破断伸び=23.4%
CTE(第1の測定)=3.4ppm/℃
CTE(第2の測定)=1.4ppm/℃
492.6℃で1.0%のTGA重量損失
450nmでの透過率=61%
550nmでの透過率=79%
750nmでの透過率=85%
この実施例は、式III、具体的には式IIIB-1を有するジアミン:4,4’-(ナフタレン-1,5-ジイル)ビス(3-(トリフルオロメチル)アニリン)、化合物17の調製を示している。
機械式攪拌機、内部温度計、及び窒素バブラーを備えた20Lの4口丸底フラスコに、室温で、ジクロロメタン(10000mL)におけるナフタレン-1,5-ジオール(500g、3124.0ミリモル)とピリジン(1259mL、15620.0ミリモル)を入れた。トリフルオロメタンスルホン酸無水物(1320mL、7810.0ミリモル)を5~10℃で4時間かけて滴下した。トリフルオロメタンスルホン酸無水物の添加が完了した後、反応混合物を室温で撹拌した。16時間後、反応混合物を10~15℃で水(5000mL)に注ぎ、30分間撹拌した。有機層を分離し、水層をジクロロメタン(2×5000mL)で抽出した。合わせた有機相を1N HCl(7500mL)及び水(5000mL)で洗浄し、無水硫酸ナトリウム(Na2SO4)で乾燥させ、濾過し、減圧下で濃縮した。エタノール(2500mL)を粗固体に加え、室温で30分間撹拌した。固体材料を室温で濾過することにより収集し、真空下で乾燥させて、ナフタレン-1,5-ジイルビス(トリフルオロメタンスルホネート)(1190g、90%)を灰色の固体として得た。1H NMR(400MHz,CDCl3)δ:8.15(d,J=8.8Hz,2H),7.69(t,J=7.6Hz,2H),7.61(dd,J=0.8Hz及び7.6Hz,2H);UPLC:99.24%の純度。
機械式攪拌機、凝縮器、内部温度計、及び窒素バブラーを備えた20Lの4口丸底フラスコに、室温で、1,4-ジオキサン(5470mL)におけるナフタレン-1,5-ジイルビス(トリフルオロメタンスルホネート)(547.0g、1290.2ミリモル)、ビス(ピナコラート)ジボロン(721.0g、2838.5ミリモル)及び酢酸カリウム(760g、7741.5ミリモル)を入れた。反応混合物をアルゴンで15分間パージし、次いでPdCl2(dppf).DCM(53g、64.5ミリモル)を反応混合物に加え、アルゴンで再び10分間パージした。反応混合物を90~95℃に加熱した。4時間後、反応混合物を室温に冷却し、セライト(登録商標)の床(bed)を通して濾過し、床をジクロロメタン(2500mL)で洗浄した。合わせた濾液を無水硫酸ナトリウムで乾燥させ、濾過し、減圧下で濃縮して、黒色の固体を得た。エタノール(2188mL)を固体に加え、室温で30分間撹拌した。固体材料を濾過により収集し、真空下で乾燥させて、1,5-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ナフタレン(402g、82%)を灰色の固体として得た。1H NMR(400MHz,CDCl3)δ:8.89(dd,J=1.2Hz及び8.0Hz,2H),8.07(dd,J=1.2Hz及び6.8Hz,2H),7.53(dd,J=6.8Hz及び8.4Hz,2H),1.42(s,24H);UPLC:97.95%の純度。
機械式攪拌機、内部温度計、及び窒素バブラーを備えた3Lの4口丸底フラスコに、トルエン(800mL)における1,5-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ナフタレン(40.0g、105.2ミリモル)、4-ブロモ-3-(トリフルオロメチル)アニリン(63.1g、263.4ミリモル)、2M炭酸ナトリウム水溶液(480mL)及びAliquat-336(4mL)を入れた。反応混合物をアルゴンで15分間パージし、次いでテトラキス(トリフェニルホスフィン)パラジウム(0)(12.1g、10.5ミリモル)を加え、アルゴンのパージを更に10分間続けた。反応混合物を110~120℃に加熱した。16時間後、反応混合物を室温に冷却し、トルエン(650mL)で希釈し、セライト(登録商標)の床を通して濾過し、床をトルエン(100mL)で洗浄した。有機層を分離し、水(250mL)及びブライン(100mL)で洗浄し、無水硫酸ナトリウムで乾燥し、濾過し、減圧下で濃縮して、粗残留物を得た。粗残留物をシリカゲルカラムクロマトグラフィー(溶離液として10~15%酢酸エチル/ヘキサン)で精製し、その後エタノール-クロロホルム(1:9)を使用して共沈させて固体を得た。固体を1,4-ジオキサン(200mL)に溶解し、
1,4-ジオキサン(100mL)における4N HClを0~5℃で加え、室温で1時間撹拌を続けた。得られた固体を濾過により収集し、エタノール-酢酸エチル(3:7)で洗浄し、真空下で乾燥させて塩酸塩を得た。5%KOH溶液(210mL)を酢酸エチル(500mL)における塩に0~5℃で加え、室温で1時間撹拌を続けた。酢酸エチル層を分離し、水とブラインで洗浄し、無水硫酸ナトリウムで乾燥し、濾過し、減圧下で濃縮して、4,4’-(ナフタレン-1,5)-ジイル)ビス(3-(トリフルオロメチル)アニリン)(15.87g、34%)をオフホワイトの固体として得た。融点:270~273℃、FT-IR:1258.50cm-1(C-F)、 1H NMR(400MHz,CDCl3)δ:7.45(d,J=7.6Hz,2H),7.37-7.30(m,4H),7.20(d,J=8.4Hz,2H),7.12(d,J=2.4Hz,2H),6.92(dd,J=2.4Hz及び8.0Hz,2H),3.94(s,4H);19F NMR(376MHz,CDCl3)δ:-58.78;GCMS:446.2 [M]+ ;UPLC:2つのアトロプ異性体の混合物として99.95%の純度。
Claims (9)
- (a)式I
Raは、出現毎に同一であり又は異なり、1つ以上のテトラカルボン酸成分残基を表し、
Rbは、出現毎に同一であり又は異なり、1つ以上の芳香族ジアミン残基を表し、
30~100モル%のRbは、式II
R1及びR2は、出現毎に同一であり又は異なり、ハロゲン、アルキル、フルオロアルキル、シリル、アルコキシ、フルオロアルコキシ、及びシロキシからなる群から選択され、
a及びbは、同一であり又は異なり、1~4の整数であり、
c及びdは、同一であり又は異なり、1又は2であり、
*は結合の点を示す)を有する)の繰り返し単位構造を有するポリアミド酸と、
(b)130℃より高い沸点を有する高沸点非プロトン性溶媒と、
を含む、液体組成物。 - 請求項4に記載の、式IVの繰り返し単位を含む、ポリイミドフィルム。
- 請求項4に記載の、式IVの繰り返し単位を有する、ポリイミドフィルムを含む少なくとも1つの層を有する、有機電子デバイス。
- 前記層は、デバイス基板、カラーフィルターシート用基板、カバーフィルム、及びタッチスクリーンパネルからなる群から選択されるデバイス構成要素において使用される、請求項8に記載の電子デバイス。
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