JP7395279B2 - 電子素子のための材料 - Google Patents
電子素子のための材料 Download PDFInfo
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- JP7395279B2 JP7395279B2 JP2019143169A JP2019143169A JP7395279B2 JP 7395279 B2 JP7395279 B2 JP 7395279B2 JP 2019143169 A JP2019143169 A JP 2019143169A JP 2019143169 A JP2019143169 A JP 2019143169A JP 7395279 B2 JP7395279 B2 JP 7395279B2
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- 239000000463 material Substances 0.000 title claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000003118 aryl group Chemical group 0.000 claims description 89
- 239000011159 matrix material Substances 0.000 claims description 47
- -1 indolocarbazolyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 230000002950 deficient Effects 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000004986 diarylamino group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000001126 phototherapy Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 3
- 238000007740 vapor deposition Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
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- 125000000962 organic group Chemical group 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
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- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 claims 1
- 238000004246 ligand exchange chromatography Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 98
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- 239000002019 doping agent Substances 0.000 description 24
- 229910052717 sulfur Inorganic materials 0.000 description 23
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 12
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- 239000002184 metal Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 10
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000006069 Suzuki reaction reaction Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 125000006836 terphenylene group Chemical group 0.000 description 7
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical class C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 150000003918 triazines Chemical class 0.000 description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic 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
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical group C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
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- 238000007639 printing Methods 0.000 description 4
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
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- 208000002874 Acne Vulgaris Diseases 0.000 description 3
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- MJDJKAFECGWQRB-UHFFFAOYSA-N [6-(1-phenyl-9H-carbazol-3-yl)dibenzofuran-4-yl]boronic acid Chemical compound C1(=CC=CC=C1)C1=CC(=CC=2C3=CC=CC=C3NC1=2)C1=CC=CC=2C3=C(OC=21)C(=CC=C3)B(O)O MJDJKAFECGWQRB-UHFFFAOYSA-N 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- CNLVLSQUPFGERC-UHFFFAOYSA-N (6-boronodibenzofuran-4-yl)boronic acid Chemical compound C12=CC=CC(B(O)O)=C2OC2=C1C=CC=C2B(O)O CNLVLSQUPFGERC-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
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- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical compound C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 2
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229940078162 triadine Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
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- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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Description
入手可能な改善されたホスト材料を有することが高付加価値用途に望ましい。
AおよびA'は、同一であるか異なり、互いに独立であってよい1以上のR1基により置換されてよい5もしくは6個の環原子を有する芳香族もしくは複素環式芳香族環構造であり;
G1、G2は、出現毎に同一であるか異なり、電子不足複素環式芳香族基の群から選ばれる有機電子輸送基(ETG)であり、ETGは、好ましくは、5~60個の芳香族環原子を有するヘテロアリール基であり、N含有ヘテロアリール基が、非常に好ましいヘテロアリール基であり、もっとも好ましいETGは、トリアジン、ピリミジン、ピラジンおよびピリジンの基から選ばれるか;
または、正孔を伝導する電子リッチ有機基(LTG)であり、LTGは、好ましくは、アリールアミン、トリアリールアミン、架橋アミンの基から選ばれ、好ましい架橋アミンは、ジヒドロアクリジン、ジヒドロフェナジン、フェノキサジンとフェノチアジン、カルバゾール、架橋カルバゾール、ビスカルバゾール、インデノカルバゾールとインドロカルバゾールであり;
ここで、G1およびG2基の少なくとも一つは、電子輸送基(ETG)であらねばならず、ここで、G1およびG2基は、1以上の独立したR1基により置換されてよく;
Ar1は、G1が電子輸送基である場合は、5~60個の環原子を有する2価の芳香族または複素環式芳香族、好ましくは、芳香族の、環もしくは環構造であり、ここで、環もしくは環構造は、AおよびA'環を含む環構造とも、ETGともブリッジせず、Ar1が、ピリジレン、ピリミジレン、フェニレン、ビフェニレンもしくはフルオレン、スピロ、テルフェニレン、チオフェンもしくはフラン基であることが好ましく、好ましくは、特に、フェニレン、ビフェニレンもしくはテルフェニレン基であり、非常に特に、フェニレン基であり;
または、G1が正孔輸送基である場合は、5~60個の環原子を有する芳香族環もしくは環構造であり、ここで、環もしくは環構造は、AおよびA'環を含む環構造とも、LTGともブリッジせず、Ar1がフェニレン、ビフェニレンもしくはテルフェニレン基であることが好ましく、特に好ましくは、フェニレン基であり;
Ar2は、G2が電子輸送基である場合は、5~60個の環原子を有する2価の芳香族または複素環式芳香族環もしくは環構造であり、ここで、環もしくは環構造は、AおよびA'環を含む環構造とも、ETGともブリッジせず、Ar2が、ピリジレン、ピリミジレン、フェニレン、ビフェニレンもしくはフルオレン、スピロ、テルフェニレン、チオフェンもしくはフラン基であることが好ましく、好ましくは、特に、フェニレン、ビフェニレンもしくはテルフェニレン基であり、非常に特には、フェニレン基であり;
または、G2が正孔輸送基である場合は、5~60個の環原子を有する芳香族環もしくは環構造であり、ここで、環もしくは環構造は、AおよびA'環を含む環構造とも、LTGともブリッジせず、Ar2がフェニレン、ビフェニレンもしくはテルフェニレン基であることが好ましく、特に好ましくは、フェニレン基であり;
Vは、単結合、C=O、C(R1)2、NAr3、O、S、Si(R1)2、BR1、PR1、P(=O)R1、SOもしくはSO2であり、単結合の場合には、AおよびA'環の炭素原子は、単結合により互いに直接結合し、好ましくは、単結合、C(R1)2、NAr3、OおよびSであり、特に好ましくは、単結合、C(R1)2、OおよびSであり、非常に特に好ましくは、OおよびSであり、特別に好ましくは、Oであり;
Wは、単結合、C=O、C(R1)2、NR1、O、S、Si(R1)2、BR1、PR1、P(=O)R1、SOもしくはSO2であり、単結合の場合には、AおよびA'環の炭素原子は、単結合により互いに直接結合し、好ましくは、単結合、C(R1)2、NR1、OおよびSであり、特に好ましくは、単結合、C(R1)2、OおよびSであり、非常に特に好ましくは、OおよびSであり、特別に好ましくは、Oであり;
Wが単結合でない場合には、Vは単結合であり、Vが単結合でない場合には、Wは単結合であることが、さらに好ましく;
WがOもしくはSである場合には、Vは単結合であり、VがOもしくはSである場合にはWは単結合であることが、さらに非常に好ましく;
WがOである場合には、Vは単結合であり、VがOである場合にはWは単結合であることが、さらに非常に特に好ましく;
mは、0もしくは1の何れかであり;
nは、0もしくは1の何れかであり;
ここで、m=nであり;
pは、0もしくは1の何れかであり;
qは、0もしくは1の何れかであり、ここで、p+qは、1もしくは2の何れかであり;
Ar3は、1以上のR3基により置換されてよい1以上のR2基によりそれぞれ置換されてよい5~30個の環原子を有する芳香族または複素環式芳香族環もしくは環構造であり、ここで、2以上のR2基は一緒に環を形成してよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1~40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2~40個の炭素原子を有する直鎖アルケニルもしくはアルキニル基、3~40個の炭素原子を有する分岐あるいは環式アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々、1以上のR2基により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上のR2基により置換されてよい5~60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR2基により置換されてよい5~60個の芳香族環原子を有するアリールオキシ、アリールアルコキシもしくはヘテロアリールオキシ基、1以上のR2基により置換されてよい10~40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせ、または架橋可能Q基であり;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1~40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2~40個の炭素原子を有する直鎖アルケニルもしくはアルキニル基、3~40個の炭素原子を有する分岐あるいは環式アルキル、アルケニル、アルキニル、アルコキシ、アルキルアルコキシもしくはチオアルコキシ基(夫々、1以上のR3基により置換されてよく、1以上の隣接しないCH2基は、R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、SもしくはCONR3で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)、各場合に、1以上のR3基により置換されてよい5~60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR3基により置換されてよい5~60個の芳香族環原子を有するアリールオキシ、アリールアルコキシもしくはヘテロアリールオキシ基、1以上のR3基により置換されてよい10~40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基または2個以上のこれらの基の組み合わせであり;同時に、2個以上の隣接するR2基は、一緒に、単環式あるいは多環式の脂肪族もしくは芳香族環構造を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1~20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族ヒドロカルビル基であって、ここで、1以上の水素原子は、Fで置き代えられてよく、同時に、2個以上のR3置換基は、一緒に単環式あるいは多環式の脂肪族もしくは芳香族環構造を形成してもよく;
ただし、A環中の1個を超えないR1置換基とA'環中の1個を超えないR1置換基は、5~30個の環原子を含む芳香族もしくは複素環式芳香族基を含む。
これは、たとえば、G1がETGならば、G1は正孔伝導性である如何なる基も含むことができないことを意味する。
Xは、出現毎に同一であるか異なり、NまたはCR1であり;
Qは、出現毎に同一であるか異なり、X=X、S、OまたはNR1、好ましくは、X=X、SおよびO、非常に好ましくは、X=XおよびS、最も好ましくは、X=Xである。
Q'は、出現毎に同一であるか異なり、CR1またはNであり;
Q"は、NR1、OまたはSであり;
ここで、少なくとも一つのQ'は、Nであり、および/または少なくとも一つのQ"は、NR1である。
HOMO(eV)=((HEh*27.212)-0.9899)/1.1206
LUMO(eV)=((LEh*27.212)-2.0041)/1.385
これらの値は、本願の文脈で、材料のHOMOおよびLUMOエネルギー準位としてみなすべきである。
使用されるアノードが、-5eV以下の電子仕事関数を有すると、正孔輸送基のHOMOエネルギーは、-3.5eV未満(すなわち、-3.5eVより負である。)である。
正孔輸送基が、アノードの電子仕事関数以下の、最も好ましくは、未満のHOMOエネルギーを有することが、非常に好ましい。
Ar4は、出現毎に同一であるか異なり、1以上のR1基により置換されてよい6~13個の芳香族環原子を有するアリールもしくはヘテロアリール基から選ばれ;
Ar5は、出現毎に同一であるか異なり、1以上のR1基により置換されてよい6~13個の芳香族環原子を有するアリールもしくはヘテロアリール基から選ばれ;
X2は、出現毎に同一であるか異なり、C(R2)2、Si(R2)3、C=O、O、S、S=O、SO2およびNR2から選ばれ;
Yは、単結合であり;
nは、出現毎に同一であるか異なり、0、1、2、3もしくは4であり;
iは、出現毎に同一であるか異なり、0もしくは1であり;
kは、出現毎に同一であるか異なり、0もしくは1であり、ここで、環毎の少なくとも一つの添え字kは、1であらねばならず;
その他について、上記定義があてはまる。
以下のスキームは、より特別な場合を使用する例により、言及したプロセスの適用を例示し、上記定義が使用する記号と添え字に適用される。以下のスキーム中でAr基は、出現毎に同一であるか異なり、ETG、LTGと式(1)の一般的なそれに対する上記定義が満足されるように選択されてよい芳香族もしくは複素環式芳香族基である。
多くの2ハロゲン化物と2ボロン酸が、市販されているか、またはスキーム6で特定されるとおりに合成することができる。それらは、引き続き、スズキカップリングにより所望の生成物に変換することができる。
本発明の化合物の調製のためのさらなる選択肢は、カルバゾール誘導体の変換と、引き続くウルマンもしくはブッフバルトカップリングである。
高い溶解性は、化合物の適切な置換により成し遂げることができる。
本発明で開示された各特長は、明確に除外されなければ、同じか、等価か、類似する目的に役立つ代替的特徴により置き代えられてよい。したがって、特に断らなければ、本発明で開示された各特長は、一般的な一連の例としてか、等価か類似する特長とみなされなければならない。
以下の合成を、別段の指定がない限り、無水溶媒中で保護ガス雰囲気下で実施する。溶媒及び試薬を、たとえば、Sigma-ALDRICHまたはABCRから購入することができる。文献から公知の化合物に対して示されている角括弧中の数字は、CAS番号である。
3-ジベンゾフラン-4-イル-9-フェニル-9H-カルバゾールの合成
ビス(ビフェニル-4-イル)ジベンゾフラン-4-イルアミンの合成
9-フェニル-3-(6-トリメチルシラニルジベンゾフラン-4-イル)-9H-カルバゾールの合成
収率:34g(72ミリモル)、理論値の60%。
B-[6-(フェニル-9H-カルバゾール-3-イル)-4-ジベンゾフラニル]ボロン酸の合成
B-[6-(フェニル-9H-カルバゾール-3-イル)-4-ジベンゾフラニル]ボロン酸の合成
3-(6-ブロモジベンゾフラン-4-イル)-9-フェニル-9H-カルバゾールの合成
3-{6-[3-(4,6-ジフェニル-[1,3,5]トリアジン-2-イル)フェニル]ジベンゾフラン-4-イル}-9-フェニル-9H-カルバゾールの合成
残留物をトルエンから再結晶化させ、最後に高真空下(p=5×10-5ミリバール)で昇華させる。純度は99.9%である。
9,9’-ジフェニル-8-(3-{4-フェニル-6-[(E)-((Z)-1-プロペニル)-ブタ-1,3-ジエニル] -[1,3,5]トリアジン-2-イル}-フェニル)-9H,9’H-[1,2’]ビカルバゾリルの合成
B(活性レベル1)を通して濾過し、水で洗浄し、乾燥させ、濃縮させる。収率は42g(53ミリモル)であり、理論値の77%に対応する。残留物をトルエンから再結晶化させ、最後的に高真空下(p=5×10-5ミリバール)で昇華させる。純度は99.9%である。
2-{6-[4-(2,6-ジフェニルピリジン-4-イル)フェニル]ジベンゾフラン-4-イル}-4,6-ジフェニル[1,3,5]トリアジンの合成
対称化合物の場合、最初の0.5当量の反応物2と、次いで0.5当量の反応物3とを添加する。
2-{6-[4-(2,6-ジフェニル-[1,3,4]トリアジン-4-イル)フェニル]-ジベンゾフラン-4-イル}-4,6-ジフェニル-[1,3,5]トリアジンの合成
a) 2-(6-ブロモジベンゾフラン-4-イル)-4,6-ジフェニル-[1,3,5]トリアジンの調製
2-(4-ジベンゾフラン-3-イル-フェニル)-4,6-ジフェニル-[1,3,5]トリアジンの調製
2,4-ジフェニル-6-[4-(6-トリメチルシラニル-ジベンゾフラン-3-イル)フェニル]- [1, 3,5]トリアジンの調製
3-[4-(4,6-ジフェニル-[1,3,5]トリアジン-2-イル)フェニル]-ジベンゾフラン-6-ボロン酸の調製
3-{7-[4-(4,6-ジフェニル-[1,3,5]トリアジン-2-イル)フェニル]-ジベンゾフラン-4-イル}-9-フェニル-9H-カルバゾールの調製
OLEDの製造および特性決定
以下の例C1~I22(表1と2を参照)では、種々のOLEDのデータが提示されている。厚さ50nmの構造化されたITO(インジウム錫酸化物)で被覆された、清浄にした(研究室の食器洗浄機、Merck Extran洗浄剤で洗浄した)ガラス薄板が、改善された加工のために、20nmのPEDOT:PSS(ポリ(3, 4-エチレンジオキシチオフェン)ポリ(スチレン・スルホン酸)で水溶液からのスピン、Heraeus Clevios Metals GmbH独国からCLEVIOS(登録商標)P VP AI 4083として購入)で被覆される。これらの被覆されたガラス薄板はOLEDが適用される基板を形成する。
先行技術による材料VG-6がETLで使用されるOLEDと比べて、本発明の材料INV-5、INV-7、INV-15、INV-21、INV-20を使用するとき、電圧と効率の著しい改善が観察される。特に、物質INV-5を使用するとき、VG-6と比べて、1.5Vまでの改善された電圧が得られ、たとえば35%のより良好な外部量子効率と、二倍を超える電力効率が得られる(例C6、I5)。
ピリミジンとジベンゾフランとの間にフェニル環を挿入することによって、15%までのEQEの改善と、0.1Vまでの電圧の改善が可能である(例C1、I1)。このことはトリアジンを含む化合物の同じような方法にもあてはまる(例C2、I2、I3)。
Claims (14)
- 一般式(8)の化合物:
Xは、出現毎に同一であるか異なり、CR1であり;
AおよびA'は、同一であるか異なり、6個の環原子を有する芳香族環構造であり;
G1は、出現毎に同一であるか異なり、正孔を伝導する電子リッチ有機基(LTG)であり、LTGは、1以上のR1で置換されてよいカルバゾリル基、ビスカルバゾリル基、インデノカルバゾリル基とインドロカルバゾリル基であり;
G2は、出現毎に同一であるか異なり、電子不足複素環式芳香族基の群から選ばれる有機電子輸送基(ETG)であり、ETGは、ピリミジル基、1,2,4-トリアジニル基もしくは1,3,5-トリアジニル基であり、それぞれ、1以上のR1で置換されてよく、または式(E-9)もしくは(E-10)であり;
Q'は、出現毎に同一であるか異なり、CR1またはNであり;
ここで、少なくとも一つのQ'は、Nであり;
Ar1は、フェニレンであり、AおよびA'環を含む環構造とも、ETGともブリッジせず;
Ar2は、フェニレンであり、AおよびA'環を含む環構造とも、ETGともブリッジせず;
pは、0もしくは1の何れかであり;
qは、0もしくは1の何れかであり、ここで、p+qは、1もしくは2の何れかであり;
R1は、出現毎に同一であるか異なり、H、D、F、1~40個の炭素原子を有する直鎖アルキル基、3~40個の炭素原子を有する分岐あるいは環式アルキル基(夫々の基は、1以上のR 2 により置換されてよい。)、各場合に、1以上のR 2 により置換されてよい6~60個の芳香族環原子を有する芳香族環構造であり;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、N(R3)2、CN、NO2、Si(R3)3、B(OR3)2、C(=O)R3、P(=O)(R3)2、S(=O)R3、S(=O)2R3、OSO2R3、1~40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2~40個の炭素原子を有する直鎖アルケニルもしくはアルキニル基、3~40個の炭素原子を有する分岐あるいは環式アルキル、アルケニル、アルキニル、もしくはチオアルコキシ基(夫々の基は、1以上のR 3 により置換されてよい。)、各場合に、1以上のR 3 により置換されてよい5~60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上のR 3 により置換されてよい5~60個の芳香族環原子を有するアリールオキシ、アリールアルコキシもしくはヘテロアリールオキシ基、1以上のR 3 により置換されてよい10~40個の芳香族環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基であり;
R3は、出現毎に同一であるか異なり、H、D、F、1~20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族ヒドロカルビル基であって、ここで、1以上の水素原子は、Fで置き代えられてよく;
ただし、A環中の1個を超えないR 1 とA'環中の1個を超えないR 1 は、6~30個の環原子を含む芳香族基を含む。 - pは0であり、qは1であることを特徴とする、請求項1記載の化合物。
- 請求項1~5何れか1項記載の少なくとも一つの化合物と、蛍光エミッター、燐光エミッター、ホスト材料、マトリックス材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、電子ブロック材料および正孔ブロック材料より成る群から選ばれる少なくとも一つのさらなる化合物を含む組成物。
- さらなる化合物が、ホストまたはマトリックス材料であることを特徴とする、請求項6記載の組成物。
- さらなる化合物が、2.5eV以上のバンドギャップを有することを特徴とする、請求項6または7記載の組成物。
- 請求項1~5何れか1項記載の少なくとも一つの化合物または請求項6~8何れか1項記載の少なくとも一つの組成物と少なくとも一つの溶媒とを含む電子素子用調合物。
- 請求項1~5何れか1項記載の少なくとも一つの化合物または請求項6~8何れか1項記載の少なくとも一つの組成物を含む電子素子。
- 有機集積回路(O-IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機エレクトロルミッセンス素子、有機太陽電池(O-SC)、有機光学検査素子、有機光受容体から選ばれる、請求項10記載の電子素子。
- 有機エレクトロルミッセンス素子が、有機発光トランジスタ(OLET)、有機電場消光素子(OFQD)、有機発光電子化学電池(OLEC、LEEC、LEC)、有機レーザーダイオード(O-laser)および有機発光ダイオード(OLED)より成る群から選ばれる、請求項11記載の電子素子。
- 少なくとも一つの有機層が、気相堆積によりまたは溶液から適用されることを特徴とする、請求項10~12何れか1項記載の電子素子の製造方法。
- 光治療のための医療用途での使用のための請求項10~12何れか1項記載の電子素子。
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CN105408448A (zh) | 2016-03-16 |
KR101925192B1 (ko) | 2018-12-04 |
JP2022000427A (ja) | 2022-01-04 |
US20160181548A1 (en) | 2016-06-23 |
JP2016534095A (ja) | 2016-11-04 |
US11588117B2 (en) | 2023-02-21 |
KR20160038006A (ko) | 2016-04-06 |
KR102202756B1 (ko) | 2021-01-13 |
EP3027707B1 (de) | 2019-12-11 |
JP6961345B2 (ja) | 2021-11-05 |
JP7395544B2 (ja) | 2023-12-11 |
KR20180129977A (ko) | 2018-12-05 |
CN109666026A (zh) | 2019-04-23 |
US20230210004A1 (en) | 2023-06-29 |
WO2015014434A1 (de) | 2015-02-05 |
EP3647393A1 (de) | 2020-05-06 |
CN105408448B (zh) | 2018-11-02 |
EP3027707A1 (de) | 2016-06-08 |
KR20200017003A (ko) | 2020-02-17 |
JP2020015727A (ja) | 2020-01-30 |
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