JP5390693B2 - 有機電子素子及びその化合物、端末 - Google Patents
有機電子素子及びその化合物、端末 Download PDFInfo
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- JP5390693B2 JP5390693B2 JP2012501944A JP2012501944A JP5390693B2 JP 5390693 B2 JP5390693 B2 JP 5390693B2 JP 2012501944 A JP2012501944 A JP 2012501944A JP 2012501944 A JP2012501944 A JP 2012501944A JP 5390693 B2 JP5390693 B2 JP 5390693B2
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- 150000001875 compounds Chemical class 0.000 title claims description 87
- 239000010410 layer Substances 0.000 claims description 127
- 239000000126 substance Substances 0.000 claims description 61
- 239000000463 material Substances 0.000 claims description 59
- 238000002347 injection Methods 0.000 claims description 46
- 239000007924 injection Substances 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 42
- 230000005525 hole transport Effects 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000011368 organic material Substances 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 65
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 44
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 41
- 230000002194 synthesizing effect Effects 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 20
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- 238000001308 synthesis method Methods 0.000 description 17
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- 230000015572 biosynthetic process Effects 0.000 description 14
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- 229910052751 metal Inorganic materials 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940049964 oleate Drugs 0.000 description 4
- 239000007774 positive electrode material Substances 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
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- 239000000470 constituent Substances 0.000 description 3
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- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- 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 2
- 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 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
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- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
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- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 208000006930 Pseudomyxoma Peritonei Diseases 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- OQNXPQOQCWVVHP-UHFFFAOYSA-N [Si].O=[Ge] Chemical class [Si].O=[Ge] OQNXPQOQCWVVHP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- APLQAVQJYBLXDR-UHFFFAOYSA-N aluminum quinoline Chemical compound [Al+3].N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12.N1=CC=CC2=CC=CC=C12 APLQAVQJYBLXDR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- HXWWMGJBPGRWRS-UHFFFAOYSA-N b2738 Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-UHFFFAOYSA-N 0.000 description 1
- PPYIVKOTTQCYIV-UHFFFAOYSA-L beryllium;selenate Chemical compound [Be+2].[O-][Se]([O-])(=O)=O PPYIVKOTTQCYIV-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 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 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010345 tape casting 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
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 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
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Description
以下、製造例及び実験例を通じて本発明をより詳細に説明する。しかしながら、以下の製造例及び実験例は本発明を例示するためのものであり、本発明の範囲がこれらにより限定されるものではない。
以下、<化学式8>乃至<化学式10>に属するアリールまたはヘテロアリールにインデンとインドルが縮合した化合物に対する製造例または合成例を説明する。但し、<化学式8>乃至<化学式10>に属するアリールまたはヘテロアリールにインデンとインドルが縮合した化合物の数が多いので、<化学式8>乃至<化学式10>に属するアリールまたはヘテロアリールにインデンとインドルが縮合した化合物のうち、1つまたは2つずつだけを例示的に説明する。本発明が属する技術分野の通常の知識を有する者、即ち当業者であれば、下記に説明した製造例を通じて例示しない本発明に属するアリールまたはヘテロアリールにインデンとインドルが縮合した化合物を製造することができる。
アルゴン雰囲気下で1−ブロモ−2−ナイトロベンゼン(12.12g、60mmol)、中間体1(11.90g、50mmol)、テトラキストリフェニルホスフィンパラジウム(0.5g、4.32mmol)をTHF 500ml、水250mlにK2CO3を入れて24時間加熱還流する。収得した固体を水及びメタノールで洗浄した後、シリカゲルコラムクロマトグラフィーで分離して中間体2を78%の収率で収得した。
オルソダイクロロベンゼンに溶かした化合物2(1.89g、5.98mmol)とトリフェニルホスフィンパラジウム(3.92g、14.85mmol)を2−neckに入れて還流して24時間攪拌すれば、黄色から褐色に溶媒色が変わる。その後、常温まで温度を上げて濃縮し、シリカゲルコラムクロマトグラフィーで分離して中間体3aと3bを各々45%、45%の収率で収得した。
1000mLの二口丸い底フラスコに1-iodo-2-nitrobenzene(102.74mmol、25.58g)、2-bromophenylboronic acid(102.74mmol、20.63g)、tetrakistriphenylphosphine palla dium(0)(3.08mmol、3.56g)、potassium cabonate(308.21mmol、42.60g)を入れて、溶媒として300mLのTetrahydrofuran(THF)と100mLの水を入れて、80℃で攪拌する。反応溶液の温度を常温に下げ、ダイクロロメタンで抽出した。得られた抽出液を無水硫酸マグネシウムで乾燥し、濃縮した。得られた混合物をシリカゲル管クロマトグラフィーで分離して白色固体の表題化合物20.00gを得た(収率:70%)。
オルソダイクロロベンゼンに溶かした化合物5とトリフェニルホスフィンパラジウムを2−neckに入れて還流して24時間攪拌すれば、黄色から褐色に溶媒色が変わる。その後、常温まで温度を上げて濃縮し、シリカゲルコラムクロマトグラフィーで分離して中間体6を75%の収率で収得した。
500mLの二口丸い底フラスコに4-bromo-9H-carbazole(67.19mmol、16.53g)を入れて、窒素を充填する。そして、300mLの無水Tetrahydrofuran(THF)を入れて、溶かした後、−78℃でn-Butyllithium in Hexane 2.5M(70.55mmol、28.22mL)をゆっくりいれる。そして、温度を常温にし、30分攪拌後、また温度を−78℃にし、2-bromo benzoyl chloride(67.19mmol、14.74g)を無水Tetrahydrofuran(THF)にゆるくしてゆっくり入れる。温度を常温にし、攪拌し、反応が終わると、ダイクロロメタンで抽出し、得られた抽出液を無水硫酸マグネシウムで乾燥し、濃縮する。得られた混合物をシリカゲル管クロマトグラフィーで分離して、黄色固体の中間体7の18.02gを77%の収率で得た。
1000mLの二口丸い底フラスコに(2-bromophenyl)(9H-carbazol-4-yl)methanone(85.66mmol、27.77g)、Pd(OAc)2(0.86mmol、0.19g)を入れて、窒素を充填した。ここに、溶媒として500mLのDimethyformamideを入れて、P(o-tol)3(1.71mmol、0.52g)を入れた後、90℃で攪拌した。反応が終わると、反応溶液の温度を常温に下げ、エタンオールを加えて沈殿物をフィルターした。得られた混合物をシリカゲル管クロマトグラフィー(溶離液−ダイクロロメタン:n−ヘキサン=3:7)に分離して、白色固体の表題化合物15.0gを50%の収率で得た。
500mLの二口丸い底フラスコに中間体8を入れて、窒素を充填する。そして、300mLの無水THFを入れて溶かした後、−78℃でMethylmagnesium bromide 3M(63.03mmol、25.32mL)をゆっくりいれる。そして、ゆっくり温度を常温にし、攪拌し、反応が終わると、ダイクロロメタンで抽出し、得られた抽出液を無水硫酸マグネシウムで乾燥し、濃縮する。得られた混合物をシリカゲル管クロマトグラフィーで分離して、黄色固体の中間体3cを80%の収率で得た。
250mLの二口フラスコに化合物3aの0.48g(1.70mmol)、4−ブロモバイフェニル0.40g(1.70mmol)を入れた後、Pd2(dba)3 0.078g(0.085mmol)、(t-Bu)3P 0.34g(1.70mmol)、t-BuONa 0.36g(3.70mmol)、トルエン150mLを入れた後、還流させながら攪拌する。
水とMCを入れて抽出した後、MgSO4で乾燥してMC/ヘキサン(Hexane)(3:7)に、シリカゲルコラムクロマトグラフィーで分離した後、ヘキサン(Hexane)で再結晶し、フィルターして、中間体Aを収得した。
二口フラスコに化合物A(2g、4.59mmol)をMCに溶かした後、0℃でNBS(1.65g、9.20mmol)を入れる。30分後に常温に上げて、6時間攪拌する。反応終結後、ソディウムバイカーボネートを溶かした水溶液とMCで抽出し、再度水で数回抽出して濃縮した後、MgSO4で乾燥し、フィルターする。受けた濾液を濃縮してアセトン/ヘキサン(1:3)の溶液で洗浄した後、乾燥して中間体Bを得た。
1−ブロモ−2−ナイトロベンゼンの代りに中間体Bを、中間体1の代りにバイフェニル−4−イルボロニックアシッドを使用したことを除いては、全ての合成工程のような方式により化合物を合成した。
化合物3aの代りに化合物3bを、4−ブロモバイフェニルの代りにブロモバイフェニルを使用したことを除いては、全ての合成工程のような方式により化合物を合成した。
化合物Aの代りに化合物A’を使用したことを除いては、全ての合成工程のような方式により化合物を合成した。
1−ブロモ−2−ナイトロベンゼンの代りに中間体B’、中間体1の代りに9, 9−ダイメチル−9H−フルオレン−2−イルボロニックアシッドを使用したことを除いては、全ての合成工程のような方式により化合物を合成した。
上記中間体A’合成方法において、化合物3bの代りに化合物3cを、ブロモバイフェニルの代りに4-chloro-2,6-diphenylpyrimidineを使用したことを除いては、全ての合成工程のような方式により化合物を合成した。
N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amineと1-Bromo-4-iodobenzene、Pd2(dba)3、Triphenylphosphine、Sodium tert-butoxideをtoluene溶媒に入れて130度で24時間還流攪拌する。反応終結後、MCと水で抽出し、MgSO4で乾燥して濃縮した後、生成された化合物をコラムクロマトグラフィーを用いて分離して希望の化合物である中間体aを68%の収率で得た。
中間体aをTHFに溶かした後、−78度でn−BuLiをゆっくり滴下した後、1時間程度攪拌する。その後、Triisopropylborateを−78度でゆっくり滴下して攪拌した後、1NHClでacid処理して、水とEAで抽出した後、MgSO4で乾燥してヘキサンで再結晶して中間体bを54%収率で得た。
二口フラスコに化合物AをMCに溶かした後、0℃でNBSを入れる。30分後、常温に上げて、6時間攪拌する。反応終結後、ソディウムバイカーボネートを溶かした水溶液とMCで抽出し、再度水で数回抽出して濃縮した後、MgSO4で乾燥し、フィルターする。受けた濾液を濃縮してアセトン/ヘキサン(1:3)の溶液で洗浄した後、乾燥して中間体cを得た。
中間体bと中間体c、Pd(PPh3)4をTHF 500ml、水250mlにK2CO3を入れて、24時間加熱還流する。収得した固体を水及びメタノールで洗浄した後、シリカゲルコラムクロマトグラフィーで分離して白色固体である生成物B−20を71%収率で収得した。
中間体aの合成法で、N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amineの代わりにDibiphenyl-4-ylamineを入れることを除いては、中間体aの合成方法と同一である。
中間体bの合成法で、中間体aの代わりに中間体eを入れることを除いては、中間体bの合成方法と同一である。
中間体cの合成法で、化合物Aの代わりに化合物A’を入れることを除いては、中間体cの合成方法と同一である。
中間体A−14の合成法で、中間体cの代わりに中間体fを、中間体bの代わりに中間体eを入れることを除いては化合物A−14の合成方法と同一である。
中間体Aの合成法で、3aの代わりに3cを入れることを除いては、中間体Aの合成方法と同一である。
中間体cの合成法で、中間体Aの代わりに中間体gを入れることを除いては、中間体cの合成方法と同一である。
中間体A−14の合成法で、中間体cの代わりに中間体hを入れることを除いては、化合物A−14の合成方法と同一である。
合成により得た化合物A−9、B−10、C−6の各々を発光層の発光ホスト物質に使用して通常的な方法により有機電界発光素子を製作した。
比較のために、本発明の化合物の代りに下記の式で表示される化合物(以下、CBPと略記する)を発光ホスト物質に使用して試験例と同一な構造の有機電界発光素子を製作した。
合成を通じて得た化合物A−14、B−12、C−13の各々を正孔輸送層に使用して、通常的な方法により有機電界発光素子を製作した。
本発明の化合物を正孔輸送層に測定した場合、比較のために、本発明の化合物の代りに下記の式で表示される化合物(以下、NPBと略記する)を正孔輸送物質に使用して、実験例と同一な構造の有機電界発光素子を製作した。
Claims (10)
- 下記化学式で表現される化合物であって、
Yは、CR’を表し、前記R’は、水素又は核炭素数1乃至6のアルキル基(C 1 〜C 6 アルキル基)であり、
R1及びR2は、各々独立的に、水素、核炭素数1乃至6のアルキル基(C 1 〜C 6 アルキル基)及び核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)からなる群から選択され、
R3は、独立的に、水素;非置換又は-NR a R b (R a 及びR b は、各々独立的に水素、核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)及び非置換又は核炭素数1乃至6のアルキル基(C 1 〜C 6 アルキル基)で置換されたフルオレニル基からなる群から選択される)で置換された核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基);非置換又は核炭素数1乃至6のアリール基(C 6 〜C 20 アリール基)で置換された少なくとも1つの窒素原子を有する核炭素数4乃至20のヘテロアリール基(C 4 〜C 20 ヘテロアリール基);非置換又は核炭素数1乃至6のアルキル基(C 1 〜C 6 アルキル基)で置換されたフルオレニル基;または、-NR c R d (R c 及びR d は、各々独立的に、水素及び核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)からなる群から選択される)であり、
R4は、非置換又は少なくとも1つの窒素原子を有する核炭素数4乃至20のヘテロアリール基(C 4 〜C 20 ヘテロアリール基、当該C 4 〜C 20 ヘテロアリール基は、非置換又は核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)でさらに置換されている)で置換された核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基);もしくは、非置換又は核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)で置換された少なくとも1つの窒素原子を有する核炭素数4乃至20のヘテロアリール基(C 4 〜C 20 ヘテロアリール基)であり、
R 5 は、水素又は核炭素数6乃至20のアリール基(C 6 〜C 20 アリール基)である。 - 請求項1又は請求項2の化合物を含む1層以上の有機物層を含むことを特徴とする、有機電子素子。
- 前記化合物を溶液工程(soluble process)により前記有機物層を形成することを特徴とする、請求項3に記載の有機電子素子。
- 前記有機電子素子は、第1電極、前記1層以上の有機物層及び第2電極を順次に積層された形態に含む有機電界発光素子であることを特徴とする、請求項3に記載の有機電子素子。
- 前記有機物層は発光層を含み、前記化合物が前記発光層の発光ホスト物質に使われることを特徴とする、請求項5に記載の有機電子素子。
- 前記有機物層は正孔輸送層を含み、前記化合物が前記正孔輸送層に使われることを特徴とする、請求項5に記載の有機電子素子。
- 前記有機物層は正孔注入層を含み、前記化合物が前記正孔注入層に使われることを特徴とする、請求項5に記載の有機電子素子。
- 請求項3の有機電子素子を含むディスプレイ装置と、
前記ディスプレイ装置を駆動する制御部と、を含むことを特徴とする、端末。
- 前記有機電子素子は、有機電界発光素子(OLED)、有機太陽電池、有機感光体(OPC)ドラム、有機トランジスタ(有機TFT)、フォトダイオード(photodiode)、有機レーザー(organic laser)、レーザーダイオード(laser diode)のうちの1つであることを特徴とする、請求項9に記載の端末。
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KR102622167B1 (ko) * | 2018-12-26 | 2024-01-08 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
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JP2002184581A (ja) * | 2000-12-13 | 2002-06-28 | Sanyo Electric Co Ltd | 有機発光素子 |
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DE102005023437A1 (de) * | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
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KR20080047209A (ko) * | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
DE102008017591A1 (de) | 2008-04-07 | 2009-10-08 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8057919B2 (en) * | 2008-06-05 | 2011-11-15 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
DE102009005288A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP5390693B2 (ja) * | 2009-03-30 | 2014-01-15 | ドゥクサン ハイ メタル カンパニー リミテッド | 有機電子素子及びその化合物、端末 |
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EP2415773A2 (en) | 2012-02-08 |
US20120018717A1 (en) | 2012-01-26 |
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