JP2021534113A - 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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- JP2021534113A JP2021534113A JP2021506711A JP2021506711A JP2021534113A JP 2021534113 A JP2021534113 A JP 2021534113A JP 2021506711 A JP2021506711 A JP 2021506711A JP 2021506711 A JP2021506711 A JP 2021506711A JP 2021534113 A JP2021534113 A JP 2021534113A
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- 229920000642 polymer Polymers 0.000 title description 27
- 229920000768 polyamine Polymers 0.000 claims abstract description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 26
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 23
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 16
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 16
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract 6
- 229920005575 poly(amic acid) Polymers 0.000 claims description 124
- 229920001721 polyimide Polymers 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 48
- 239000004642 Polyimide Substances 0.000 claims description 39
- 239000007788 liquid Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 238000009835 boiling Methods 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 25
- 150000004985 diamines Chemical class 0.000 claims description 24
- 239000000010 aprotic solvent Substances 0.000 claims description 23
- 125000004427 diamine group Chemical group 0.000 claims description 20
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 125000006157 aromatic diamine group Chemical group 0.000 claims 2
- 239000013039 cover film Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 21
- 238000000034 method Methods 0.000 description 249
- 238000006243 chemical reaction Methods 0.000 description 224
- 230000008569 process Effects 0.000 description 205
- 239000010410 layer Substances 0.000 description 124
- 239000000463 material Substances 0.000 description 105
- 239000000243 solution Substances 0.000 description 79
- 239000010953 base metal Substances 0.000 description 56
- 239000002904 solvent Substances 0.000 description 40
- 150000001875 compounds Chemical class 0.000 description 33
- 230000004048 modification Effects 0.000 description 32
- 238000012986 modification Methods 0.000 description 32
- -1 polyethylene terephthalate Polymers 0.000 description 30
- 239000002245 particle Substances 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 26
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 25
- 239000010408 film Substances 0.000 description 24
- 239000011521 glass Substances 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 238000000576 coating method Methods 0.000 description 19
- 239000011159 matrix material Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 18
- 150000008064 anhydrides Chemical class 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 229920001774 Perfluoroether Polymers 0.000 description 10
- 239000004793 Polystyrene Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 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 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 229920002223 polystyrene Polymers 0.000 description 10
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 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 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 150000004984 aromatic diamines Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000012545 processing 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
- 125000003277 amino group Chemical group 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 6
- BSVCWDYIEZACRZ-UHFFFAOYSA-N 4-[6-[4-amino-2-(trifluoromethyl)phenyl]anthracen-2-yl]-3-(trifluoromethyl)aniline Chemical compound NC1=CC(=C(C=C1)C1=CC2=CC3=CC=C(C=C3C=C2C=C1)C1=C(C=C(C=C1)N)C(F)(F)F)C(F)(F)F BSVCWDYIEZACRZ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 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 compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 0 C[C@]1OC1*(cc(COC1)c1c1)*1C(O)=O Chemical compound C[C@]1OC1*(cc(COC1)c1c1)*1C(O)=O 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 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
- 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
- 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
- 239000002243 precursor Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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
- 238000005160 1H NMR spectroscopy Methods 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
- 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
- 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
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229920002732 Polyanhydride Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000011263 electroactive material Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 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
- 239000000852 hydrogen donor Substances 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 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
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 230000005055 memory storage Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 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
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
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- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
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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
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- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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- 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
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- 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
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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Abstract
【化1】
を有するポリアミンが開示される(式I中:Q1は、H、R1、又はR9であり;Q2は、H、R2、又はR9のものであり;Q3は、R3又はR9であり;Q4は、R4又はR9であり;Q5は、R7又はR9であり;R1及びR2は、出現ごとに同じ又は異なるものであり、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、又は非置換若しくは置換アリールオキシであり;R3、R4、R5、R6、及びR7は、同じ又は異なるものであり、H、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、又は非置換若しくは置換アリールオキシであり;R8は、アルキル、シリル、非置換若しくは置換炭化水素アリール、又は非置換若しくは置換ヘテロアリールであり;R9は、出現ごとに同じ又は異なるものであり、NH2又はArNH2であり;Arは、出現ごとに同じ又は異なるものであり、非置換若しくは置換C6~18炭化水素アリールであり;a及びbは、同じ又は異なるものであり、0〜3の整数である)。式I中、Q1〜Q5の少なくとも2つはR9である。
Description
本出願は、その全体を参照により本明細書に援用される、2018年8月8日出願の、米国仮特許出願第62/715,889号明細書の利益を主張するものである。
Q1は、H、R1、及びR9からなる群から選択され;
Q2は、H、R2、及びR9からなる群から選択され;
Q3は、R3及びR9からなる群から選択され;
Q4は、R4及びR9からなる群から選択され;
Q5は、R7及びR9からなる群から選択され;
R1及びR2は、出現ごとに同じ又は異なるものであり、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R3、R4、R5、R6、及びR7は、同じ又は異なるものであり、H、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R8は、アルキル、シリル、非置換若しくは置換炭化水素アリール、及び非置換若しくは置換ヘテロアリールからなる群から選択され;
R9は、出現ごとに同じ又は異なるものであり、NH2及びArNH2からなる群から選択され;
Arは、出現ごとに同じ又は異なるものであり、非置換若しくは置換C6~18炭化水素アリールであり;
a及びbは、同じ又は異なるものであり、0〜3の整数であり;
但し、Q1〜Q5の少なくとも2つはR9である)
を有するポリアミンが提供される。
Raは、出現ごとに同じ又は異なるものであり、1つ以上のテトラカルボン酸成分残基を表し;
Rbは、出現ごとに同じ又は異なるものであり、1つ以上の芳香族ジアミン残基を表し;
ここで、Rbの10〜100モル%は、式Iを有する1つ以上のジアミンからのジアミン残基である)
の繰り返し単位を有するポリアミド酸が更に提供される。
の構造を有するポリイミドが更に提供される。
下記の実施形態の詳細に取り組む前に、いくつかの用語が定義される又は明確化される。
本明細書に記載されるポリアミンは、式I
Q1は、H、R1、及びR9からなる群から選択され;
Q2は、H、R2、及びR9からなる群から選択され;
Q3は、R3及びR9からなる群から選択され;
Q4は、R4及びR9からなる群から選択され;
Q5は、R7及びR9からなる群から選択され;
R1及びR2は、出現ごとに同じ又は異なるものであり、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R3、R4、R5、R6、及びR7は、同じ又は異なるものであり、H、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R8は、アルキル、シリル、非置換若しくは置換炭化水素アリール、及び非置換若しくは置換ヘテロアリールからなる群から選択され;
R9は、出現ごとに同じ又は異なるものであり、NH2及びArNH2からなる群から選択され;
Arは、出現ごとに同じ又は異なるものであり、非置換若しくは置換C6~18炭化水素アリールであり;
a及びbは、同じ又は異なるものであり、0〜3の整数であり;
但し、Q1〜Q5の少なくとも2つはR9である)
を有する。
R10及びR11は、出現ごとに同じ又は異なるものであり、F、CN、アルキル、フルオロアルキル、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、アルコキシ、フルオロアルコキシ、非置換若しくは置換アリールオキシ、シリル、及びシロキシからなる群から選択され、ここで、隣接するR10及び/又はR11基は、一緒に結合して縮合環を形成し得;
p及びqは、同じ又は異なるものであり、0〜4の整数であり;
sは0〜3の整数であり;
*は結合点を示す)
を有する。
を有する。式Iにおける、R1〜R9、a、及びbについての上記の実施形態の全てが、式IAにおけるR1〜R9、a、及びbに等しく当てはまる。
を有する。式IにおけるR1、R2、R5〜R9、a、及びbについての上記の実施形態の全てが、式IBにおけるR1、R2、R5〜R9、a、及びbに等しく当てはまる。
を有する。式IにおけるR1〜R6、R8、R9、a、及びbについての上記の実施形態の全てが、式ICにおける、R1〜R6、R8、R9、a、及びbに等しく当てはまる。
本明細書に記載されるポリアミド酸は、1つ以上のポリ酸無水物と、1つ以上のポリアミンの10〜100モル%が式Iを有する、1つ以上のポリアミンとの反応生成物である。
Raは、出現ごとに同じ又は異なるものであり、1つ以上のテトラカルボン酸残基を表し;
Rbは、出現ごとに同じ又は異なるものであり、1つ以上のジアミン残基を表し;
ここで、Rbの10〜100モル%は、式Iを有する1つ以上のジアミンからの残基である)
の繰り返し単位構造を有する。
ODPA//Bis−P/TFMB 100///90/10
と表されよう。
(a)ポリアミン成分及びポリ酸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しながら溶媒に少しずつ添加される方法。
(b)溶媒がポリアミン成分とポリ酸無水物成分との撹拌混合物に添加される方法。(上記の(a)とは反対に)
(c)ポリアミンが溶媒に独占的に溶解させられ、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ポリ酸無水物がそれに添加される方法。
(d)ポリ酸無水物成分が溶媒に独占的に溶解させられ、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)成分及びポリ酸無水物成分が溶媒に別々に溶解させられ、次いでこれらの溶液が反応器中で混合される方法。
(f)過剰なポリアミン成分を持ったポリアミド酸及び過剰なポリ酸無水物成分を持った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生み出すような方法で、反応器中で相互に反応させられる方法。
(g)ポリアミン成分及びポリ酸無水物成分の特定部分が最初に反応させられ、次いで残りのポリアミン成分が反応させられるか、又は逆もまた同様である方法。
(h)成分が部分的に又は全体を任意の順序で溶媒の一部か全部かのいずれかに添加され、また任意の成分の一部又は全部が溶媒の一部又は全部中の溶液として添加され得る方法。
(i)ポリ酸無水物成分の1つをポリアミン成分の1つと最初に反応させて第1ポリアミド酸を与える方法。次いで他のポリ酸無水物成分を他のポリアミン成分と反応させて第2ポリアミド酸を与える方法。次いでフィルム形成の前に、多数の方法のいずれか1つでポリアミド酸を組み合わせる方法。
一般的に言えば、ポリアミド酸溶液は、上に開示されたポリアミド酸溶液調製方法のいずれか1つから得ることができる。
上記のポリアミド酸のイミド化から生じるポリイミドが提供される。「イミド化」とは、イミド基を形成するためのアミド酸基の分子内環化を意味する。いくつかの実施形態では、熱イミド化が用いられる。いくつかの実施形態では、化学イミド化が用いられる。いくつかの実施形態では、熱イミド化と化学イミド化との組み合わせが用いられる。
Raは、出現ごとに同じ又は異なるものであり、1つ以上のテトラカルボン酸成分残基を表し;
Rbは、出現ごとに同じ又は異なるものであり、1つ以上の芳香族ジアミン残基を表し;
ここで、Rbの10〜100モル%は、式Iを有する1つ以上のジアミンからの残基である)
の繰り返し単位構造を有する。
一般に、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。いくつかの実施形態では、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るポリイミドフィルムは、OLED及びLCDディスプレイなどの電子ディスプレイデバイスにおける多数の層で使用するのに好適であり得る。そ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、カバーフィルム等が挙げられる。各用途向けの特定の材料の特性要件は、ユニークであり、本明細書に開示されるポリイミドフィルムに対して適切な組成及び加工条件によって対処され得る。
この実施例は、式Iを有するジアミン、化合物4の調製を例示する。
トルエン(400ml)、エタノール(200ml)及び水(80ml)中の2,6−ビス−Bpinアントラセン1(14.5g、33.71mmole)、4−ブロモ−3−(トリフルオロメチル)アニリン2(24.27g、101.13mmole)、Pd(PPh3)4(3.9g、3.37mmole)及び炭酸カリウム(23.29g、169mmole)の混合物をガス抜きし、窒素雰囲気下に85℃で3日間加熱しながら撹拌した。反応混合物から沈澱した生成物3(9.7g)を熱時濾過によって集めた。濾液を冷却し、沈殿物を濾過によって集めてより低い純度の3.2gの生成物を得た。1H−NMR(DMSO−d6,500MHz):5.69(s,4H),6.88(dd,2H,J1=2Hz,J2=8Hz),7.03(d,2H,J=2Hz),7.18(d,2H,J=8Hz),7.40(d,2H,J=9Hz),7.92(s,2H),8.05(d,2H,J=9Hz),8.58(s,2H).
生成物3(7.637g、15.38mmole)、N−フェニルマレイミド(7.96g、45.97mmole)の混合物を、窒素雰囲気下に150℃で1.5時間、1,2−ジクロロベンゼン(100ml)中で加熱した。その後追加量のマレイミド(4.6g)を添加し、混合物を同じ温度で1時間加熱した。反応混合物を冷却し、ロータリーエバポレーターを用いて溶媒を蒸発させ、この残渣を、ジクロロメタン及びジクロロメタン−アセトンの混合物を使った勾配溶出を用いるシリカゲルカラムでのクロマトグラフィー精製にかけた。生成物を含有する分画を集め、溶出液を蒸発させて6.41gのジアミン化合物4を得、それは、ジクロロメタンとヘキサンとの混合物からの結晶化によって更に精製することができる。1H−NMR(DMSO−d6,500MHz):3.41(dd,1H,J1=4Hz,J2=9Hz),3.47(dd,1H,J1=4Hz,J2=9Hz),4.91(t,2H,J=4Hz),5.62(s,4H),6.53−6.55(m,2H),6.78(td,2H,J1=2Hz,J2=8Hz),6.89(d,1H,J= 8Hz),6.95(dd,2H,J1=2Hz,J2=8Hz),7.02(d,1H,J=8Hz),7.06(d,1H,J=8Hz),7.10(d,1H,J=8Hz),7.18(s,1H),7.30(d,1H,J=8Hz),7.32−7.33(m,3H),7.41(s,1H),7.49(d,1H,J=8Hz).13C−NMR(DMSO−d6,125MHz,アトロポ異性体):176.35,176.25,148.83,148.78,141.7,140.7,139.4,139.2,138.9,138.3,133.64,133.6,132.3,129.13,128.9,127.9,127.7,127.5,127.4,127.11,127.0,126.0,125.5,124.7,124.2,123.8,123.7,117.0,110.87,110.83,55.4,47.22,47.17,45.0.19F−NMR(DMSO−d6,470 MHz,アトロポ異性体):55.27,55.35.
この実施例は、式IIを有するポリアミド酸を含む液体組成物の調製を例示する。
この実施例は、ポリイミドが式IIIを有する、ポリイミドフィルムの調製を例示する。
ヘイズ:0.19%
Tg:327℃
CTE(第1測定):34.1ppm/℃
複屈折(633nm):0.042
引張弾性率:4.77GPa
引張強度:198.7MPa
破断伸び:24.6%
1%TGA損失:415℃
光学的遅れ:369
を有した。
Claims (9)
- 式I
Q1は、H、R1、及びR9からなる群から選択され;
Q2は、H、R2、及びR9からなる群から選択され;
Q3は、R3及びR9からなる群から選択され;
Q4は、R4及びR9からなる群から選択され;
Q5は、R7及びR9からなる群から選択され;
R1及びR2は、出現ごとに同じ又は異なるものであり、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R3、R4、R5、R6、及びR7は、同じ又は異なるものであり、H、F、CN、アルキル、フルオロアルキル、アルコキシ、フルオロアルコキシ、シリル、シロキシ、非置換若しくは置換炭化水素アリール、非置換若しくは置換ヘテロアリール、及び非置換若しくは置換アリールオキシからなる群から選択され;
R8は、アルキル、シリル、非置換若しくは置換炭化水素アリール、及び非置換若しくは置換ヘテロアリールからなる群から選択され;
R9は、出現ごとに同じ又は異なるものであり、NH2及びArNH2からなる群から選択され;
Arは、出現ごとに同じ又は異なるものであり、非置換若しくは置換C6~18炭化水素アリールであり;
a及びbは、同じ又は異なるものであり、0〜3の整数であり;
但し、Q1〜Q5の少なくとも2つはR9である)
を有するポリアミン。 - (a)請求項5に記載のポリアミド酸と、(b)高沸点の、非プロトン性溶媒とを含む液体組成物。
- 請求項7に記載の、式III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。
- 前記層が、デバイス基板、カラーフィルターシート用の基板、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部品に使用される、請求項8に記載の電子デバイス。
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JPH07500625A (ja) * | 1991-10-29 | 1995-01-19 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | 改善された伸び率を有する低い熱膨張率のポリイミド |
KR20090036851A (ko) * | 2007-10-10 | 2009-04-15 | 주식회사 엘지화학 | 신규한 폴리아믹산, 폴리이미드, 이를 포함하는 액정배향막및 이를 포함하는 액정디스플레이 |
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KR20090036851A (ko) * | 2007-10-10 | 2009-04-15 | 주식회사 엘지화학 | 신규한 폴리아믹산, 폴리이미드, 이를 포함하는 액정배향막및 이를 포함하는 액정디스플레이 |
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