JP6516861B2 - 有機電界発光材料 - Google Patents
有機電界発光材料 Download PDFInfo
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- JP6516861B2 JP6516861B2 JP2017547496A JP2017547496A JP6516861B2 JP 6516861 B2 JP6516861 B2 JP 6516861B2 JP 2017547496 A JP2017547496 A JP 2017547496A JP 2017547496 A JP2017547496 A JP 2017547496A JP 6516861 B2 JP6516861 B2 JP 6516861B2
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- organic electroluminescent
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- organic
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- 239000000463 material Substances 0.000 title claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
- 125000003944 tolyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 239000010410 layer Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- -1 diphenylphenyl group Chemical group 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000012776 electronic material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 150000002168 ethanoic acid esters Chemical class 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 2
- 150000002987 phenanthrenes Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- WYSBZCPNRXECEW-UHFFFAOYSA-N 1-diazo-2H-anthracene Chemical class C1=CC=C2C=C3C(=[N+]=[N-])CC=CC3=CC2=C1 WYSBZCPNRXECEW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 1
- QBAUOLJAIYOPRQ-UHFFFAOYSA-N C(#N)C1(C(C(N=NN1)(C#N)C#N)(C#N)C#N)C#N Chemical compound C(#N)C1(C(C(N=NN1)(C#N)C#N)(C#N)C#N)C#N QBAUOLJAIYOPRQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JORPCVUCPCOQHW-UHFFFAOYSA-N N1=NN=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1 Chemical compound N1=NN=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1.NC1=CC=CC=C1 JORPCVUCPCOQHW-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- OAKHTDMWGKZKOT-UHFFFAOYSA-N O1C=CC=C1.C1=CC=CC=2SC3=C(C21)C=CC=C3 Chemical group O1C=CC=C1.C1=CC=CC=2SC3=C(C21)C=CC=C3 OAKHTDMWGKZKOT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
(その中で下記の化合物1a、1b、1e、1h、3a、89aは市販の常用材料である)
反応フラスコ内にそれぞれ化合物1a(240.00g、0.88mol)、化合物1b(496.32g、1.76mol)、Pd(PPh3)4(20.35g、17.60mmol)、炭酸カリウム(302.52g、2.20mol)、トルエン(2400mL)、純水(1200mL)を投入する。窒素ガスを三回で抽出した後、加熱し始め、反応液温度が95-105℃に達し、この温度での反応を8-12h保持し、TLC及びHPLCをサンプリングして原料反応を完了する。加熱を停止し、温度が20-30℃に下降したところで抽出してろ過し、ろ過液が有機層と水層とに分けられた後、酢酸エチルで抽出し、有機層を合併し、水洗し、無水硫酸マグネシウムで乾燥し、抽出してろ過し、ろ過液を濃縮して暗い黄色の固体粗生成物を取得する。石油エーテルを再結晶化させ、灰白色の固体産物を取得した。収量が90%、純度が95%であった。
反応フラスコに相応して比例する化合物1c(302g、0.78mol)、B(OEt)3(142g、0.97mol)、n-BuLi/THF(1.6M、600mL)、無水THF(3000mL)を投入し、窒素ガスを三回で抽出した後、反応液を冷却して-75〜-65℃に下降させ、緩やかにn-BuLi/THF溶液を滴下して入れ、反応液温度を-75〜-65℃に制御し、滴下が完了した後、引き続いてこの温度反応を0.5-1h保持する。その後、所定量のB(OEt)3を滴下して入れ、反応液温度を-75〜-65℃に制御し、滴下が完了した後、引き続いてこの温度反応を0.5-1h保持した後、反応液を室温に移して自然加温で4-6h反応し、そうして2M稀塩酸を投入し、pH値を2-3に調節し、約1h攪拌した後、反応を停止する。酢酸エステルを投入して、水層を抽出してEAで抽出し、有機層を合併し、無水硫酸マグネシウムで乾燥し、抽出してろ過し、ろ過液を濃縮して灰白色の固体産物を取得した。純度が95%、収量が62.5%であった。
反応フラスコ内に化合物1d(150g、0.43mol)、化合物1e(500g、0.86mol)、Pd(PPh3)4(5.0g、0.44mmol)、炭酸カリウム(130g、0.92mol)、トルエン(1000mL)、純水(500mL)を投入し、窒素ガスを三回で抽出した後、加熱し始め、反応液温度が95-105℃に達した時、この温度反応を8-12h保持し、TLC及びHPLCをサンプリングし、原料反応を完了する。加熱を停止し、温度が20-30℃に下降したところで抽出してろ過し、ろ過液が有機層と水層に分けられた後、酢酸エステルで抽出し、有機層を合併し、無水硫酸マグネシウムで乾燥し、抽出してろ過し、ろ過液を濃縮して暗い黄色の固体の粗生成物を取得する。純度が80%、収量が78.1%であった。
反応フラスコ内に化合物1f(210g、0.42mol)、NBS(135g、0.71mol)、DMF(5L)を投入する。窒素ガスを三回で抽出した後、加熱し始め、反応液温度が60-65℃に達した時、この温度反応を6-8h保持し、TLC及びHPLCをサンプリングし、原料反応を完了する。加熱を停止し、温度が20-30℃に下降したところで反応液を氷水に入れ、暗い黄色の固体を析出させて、抽出しろ過して黄色の固体が得られ、火干で1gの粗生成物を取得する。粗生成物にDCM/MeOHを投入し、溶液が略混濁した後、引き続いて約30min攪拌し、大量の固体を析出し抽出してろ過し、浅黄色の固体産物を取得した。収量が約54.05%、純度が98.5%であった。
500ml三口フラスコ内に、化合物1g(9.5g、16.92mmol)、化合物1h(6.41g、30.51mmol)、Pd(PPh3)4(1.5g、1.3mmol)、炭酸カリウム(5.84g、42.3mmol)、トルエン(150mL)、純水(75mL)を順次投入する。窒素ガスを三回で抽出した後、105℃で反応する。液相を検出して、反応時間を約12h程度とする。反応の開始時、反応液が触媒剤のカーキとなった後、次第に黄色の溶液に変わり、反応を停止した後、上層液が澄明な浅黄色で下層液が水となる。反応の停止後、濾過して、酢酸エステルで生成物がなくなるまでろ滓を洗浄し、ろ過液を収集し、回転乾燥し、大量の灰白色の固体を析出させ、ろ滓を収集して乾燥し、目的産物を取得する。純度が98%であった。真空で昇華させることで純度99.5%の灰白色の固体粉末を取得した。
[実施例2]
[化合物3の合成]
[化合物89の合成]
[有機電界発光素子1の調製]
[本発明の有機電子材料によるOLED調製]
先ず、透明導電ITOガラス基板10(上面に陽極20を有する)が洗浄溶液及び脱イオン水、アルコール、アセトン及び脱イオン水により順次洗浄した後、酸素等のイオンで30秒処理した。
また、ITOで厚さ10nmのHAT-CN6を正孔注入層30として蒸発コーティングした。
更に、正孔伝送層の上には、30nmの厚さの化合物3を発光層50として蒸発コーティングした。
最後に、それぞれ15nmのBPhen:Liを電子注入層70として、150nmのAlを素子陰極80として蒸発コーティングした。
調製された素子は、20mA/cm2の作動電流密度での電圧が3.58Vであり、電流効率が3.21cd/Aに達し、1000cd/m2の輝度でCIEy座標が0.0853となり、青色光を発射した。
[有機電界発光素子2の調製]
その調製方法は、実施例4と同様に、化合物3を化合物89に変換することで、有機電界発光素子を調製した。
調製した素子は、20mA/cm2の作動電流密度での電圧が3.84Vであり、電流効率が2.83cd/Aに達し、1000cd/m2の輝度でCIEy座標が0.0888となり、青色光を発射した。
その方法は、実施例4と同様に、化合物3を以下の化合物TATに変換し、比較用有機電場発光素子を作製した。
[有機電界発光素子8の調製]
その調製方法は、実施例6と同様に、化合物3を化合物MADNに変換することで、有機電界発光素子を調製した。
調製の素子は、20mA/cm2の作動電流密度での電圧が5.18Vであり、電流効率が4.79cd/Aに達し、発射青色光のピーク値が460nmであり、1000cd/m2の輝度でCIEyが0.161であった。
TAT構造式
Claims (6)
- 以下の式(I)で表される構造式を備えることを特徴とする有機電界発光材料。
- R1-R2が、水素、C1-C4のアルキル基、C1-C4アルキル基置換又は非置換のフェニル基、或は結合して成るC1-C4アルキル基置換又は非置換のフルオレニル基をそれぞれ独立して表し、式中、R3-R17が水素をそれぞれ独立して表し、Ar1-Ar3がフェニル基、トルエン基、tert-ブチル基フェニル基、をそれぞれ独立して表すことを特徴する請求項1に記載の有機電界発光材料。
- R3-R17が水素を表し、R1、R2が水素、メチル基、プロピル基、エチル基、イソプロピル基、tert-ブチル基、フェニル基、或は結合して成るフルオレニル基をそれぞれ独立して表し、Ar1-Ar3がフェニル基、トルエン基をそれぞれ独立して表すことを特徴する請求項2に記載の有機電界発光材料。
- R3-R17が水素を表し、R1、R2が水素、メチル基、或は結合して成るフルオレニル基をそれぞれ独立して表し、Ar1、Ar2、Ar3がフェニル基をそれぞれ独立して表すことを特徴する請求項3に記載の有機電界発光材料。
- 以下の化合物とすることを特徴する請求項1に記載の有機電界発光材料。
- 以下の構成の化合物とすることを特徴する請求項5に記載の有機電界発光材料。
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JP4080213B2 (ja) * | 2002-02-01 | 2008-04-23 | 三井化学株式会社 | 有機電界発光素子 |
JP4067414B2 (ja) * | 2003-01-22 | 2008-03-26 | 三井化学株式会社 | 非対称置換アントラセン化合物、および該非対称置換アントラセン化合物を含有する有機電界発光素子 |
KR100857023B1 (ko) * | 2007-05-21 | 2008-09-05 | (주)그라쎌 | 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
KR100948965B1 (ko) | 2007-10-25 | 2010-03-23 | 주식회사 하나화인켐 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
KR100987822B1 (ko) | 2007-12-17 | 2010-10-13 | (주)씨에스엘쏠라 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
KR100910150B1 (ko) * | 2008-04-02 | 2009-08-03 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
JP5676454B2 (ja) * | 2008-09-25 | 2015-02-25 | ユニバーサル ディスプレイ コーポレイション | 有機セレン材料および有機発光デバイス内でのその使用 |
KR20100109293A (ko) * | 2009-03-31 | 2010-10-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
KR101427605B1 (ko) * | 2009-03-31 | 2014-08-07 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
US8642190B2 (en) * | 2009-10-22 | 2014-02-04 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene derivative, light-emitting element, light-emitting device, electronic device, and lighting device |
KR101681214B1 (ko) * | 2010-01-08 | 2016-12-01 | 에스에프씨 주식회사 | 호스트 화합물 및 이를 이용한 유기전계발광소자 |
US10026905B2 (en) * | 2012-01-18 | 2018-07-17 | Duk San Neolux Co., Ltd. | Compound, organic electric element using the same, and an electronic device thereof |
CN103456897B (zh) * | 2012-05-30 | 2016-03-09 | 京东方科技集团股份有限公司 | 有机电致发光器件 |
EP2933228A1 (en) * | 2014-04-15 | 2015-10-21 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Process for preparing single wall carbon nanotubes of pre-defined chirality |
JP2019503072A (ja) * | 2015-12-18 | 2019-01-31 | ザ トラスティーズ オブ プリンストン ユニバーシティ | 高い開路電圧を有する単接合有機光電池デバイスとそのアプリケーション |
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2015
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- 2015-09-01 DE DE112015006276.9T patent/DE112015006276B4/de active Active
- 2015-09-01 JP JP2017547496A patent/JP6516861B2/ja active Active
- 2015-09-01 KR KR1020177025531A patent/KR101992318B1/ko active IP Right Grant
- 2015-09-01 WO PCT/CN2015/088709 patent/WO2016141691A1/zh active Application Filing
- 2015-09-01 US US15/557,097 patent/US10347843B2/en not_active Expired - Fee Related
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DE112015006276B4 (de) | 2022-08-25 |
CN106032350B (zh) | 2019-03-01 |
CN106032350A (zh) | 2016-10-19 |
JP2018513884A (ja) | 2018-05-31 |
KR101992318B1 (ko) | 2019-06-24 |
DE112015006276T5 (de) | 2018-01-25 |
WO2016141691A1 (zh) | 2016-09-15 |
KR20170117482A (ko) | 2017-10-23 |
US20180047909A1 (en) | 2018-02-15 |
TWI561498B (en) | 2016-12-11 |
TW201632486A (zh) | 2016-09-16 |
US10347843B2 (en) | 2019-07-09 |
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