WO2013038650A1 - 縮合複素芳香族誘導体、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
縮合複素芳香族誘導体、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2013038650A1 WO2013038650A1 PCT/JP2012/005734 JP2012005734W WO2013038650A1 WO 2013038650 A1 WO2013038650 A1 WO 2013038650A1 JP 2012005734 W JP2012005734 W JP 2012005734W WO 2013038650 A1 WO2013038650 A1 WO 2013038650A1
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- 238000005401 electroluminescence Methods 0.000 title claims description 122
- 239000000463 material Substances 0.000 title claims description 119
- 125000006615 aromatic heterocyclic group Chemical group 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 147
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 14
- 125000000732 arylene group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 9
- 238000002347 injection Methods 0.000 claims description 63
- 239000007924 injection Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000010409 thin film Substances 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 150000001721 carbon Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000006413 ring segment Chemical group 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005566 carbazolylene group Chemical group 0.000 claims description 5
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 229910052762 osmium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052705 radium Inorganic materials 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 232
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 114
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 230000015572 biosynthetic process Effects 0.000 description 54
- 238000003786 synthesis reaction Methods 0.000 description 47
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000002019 doping agent Substances 0.000 description 33
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 32
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 32
- -1 biphenylyl group Chemical group 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- 230000004888 barrier function Effects 0.000 description 27
- 239000000523 sample Substances 0.000 description 27
- 239000012488 sample solution Substances 0.000 description 26
- 125000001424 substituent group Chemical group 0.000 description 25
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 21
- 125000002524 organometallic group Chemical group 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 238000005259 measurement Methods 0.000 description 16
- 229910000029 sodium carbonate Inorganic materials 0.000 description 16
- 238000004506 ultrasonic cleaning Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000005493 quinolyl group Chemical group 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 230000027756 respiratory electron transport chain Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 0 C*(*(C(*)(*)OC1=C*)OC)C1=C Chemical compound C*(*(C(*)(*)OC1=C*)OC)C1=C 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052788 barium Inorganic materials 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- 238000001296 phosphorescence spectrum Methods 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 4
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 4
- AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 description 3
- 150000008045 alkali metal halides Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000003282 alkyl amino 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
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 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 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000001989 lithium alloy Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000005551 pyridylene group Chemical group 0.000 description 2
- 150000002909 rare earth metal compounds Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 1
- WQBLCGDZYFKINX-UHFFFAOYSA-N (3,5-dibromophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC(Br)=C1 WQBLCGDZYFKINX-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- TWLXDPFBEPBAQB-UHFFFAOYSA-N orthoperiodic acid Chemical compound OI(O)(O)(O)(O)=O TWLXDPFBEPBAQB-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- UFQXGXDIJMBKTC-UHFFFAOYSA-N oxostrontium Chemical compound [Sr]=O UFQXGXDIJMBKTC-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- KELCFVWDYYCEOQ-UHFFFAOYSA-N phenanthridin-1-ol Chemical compound C1=CC=CC2=C3C(O)=CC=CC3=NC=C21 KELCFVWDYYCEOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- 150000004986 phenylenediamines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- OEKDNFRQVZLFBZ-UHFFFAOYSA-K scandium fluoride Chemical compound F[Sc](F)F OEKDNFRQVZLFBZ-UHFFFAOYSA-K 0.000 description 1
- HYXGAEYDKFCVMU-UHFFFAOYSA-N scandium oxide Chemical compound O=[Sc]O[Sc]=O HYXGAEYDKFCVMU-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- LCGWNWAVPULFIF-UHFFFAOYSA-N strontium barium(2+) oxygen(2-) Chemical compound [O--].[O--].[Sr++].[Ba++] LCGWNWAVPULFIF-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- TYIZUJNEZNBXRS-UHFFFAOYSA-K trifluorogadolinium Chemical compound F[Gd](F)F TYIZUJNEZNBXRS-UHFFFAOYSA-K 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- LKNRQYTYDPPUOX-UHFFFAOYSA-K trifluoroterbium Chemical compound F[Tb](F)F LKNRQYTYDPPUOX-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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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Definitions
- the present invention relates to a condensed heteroaromatic derivative, a material for an organic electroluminescence element, and an organic electroluminescence element using the same.
- Organic electroluminescence (EL) elements include a fluorescent type and a phosphorescent type, and an optimum element design has been studied according to each light emission mechanism. With respect to phosphorescent organic EL elements, it is known from their light emission characteristics that high-performance elements cannot be obtained by simple diversion of fluorescent element technology. The reason is generally considered as follows. First, since phosphorescence emission is emission using triplet excitons, the energy gap of the compound used for the light emitting layer must be large. This is because the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).
- a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must first be used for the light emitting layer. I must. Further, it is preferable to provide an electron transport layer and a hole transport layer adjacent to the light emitting layer, and use a compound having a triplet energy higher than that of the phosphorescent dopant material for the electron transport layer and the hole transport layer.
- a compound having a larger energy gap than the compound used for the fluorescent organic EL element is used for the phosphorescent organic EL element. The drive voltage of the entire element increases.
- hydrocarbon compounds having high oxidation resistance and reduction resistance useful for fluorescent elements have a large energy gap due to the large spread of ⁇ electron clouds. Therefore, in a phosphorescent organic EL element, it is difficult to select such a hydrocarbon compound, and an organic compound containing a heteroatom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element.
- the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance. That is, since light emitted from singlet excitons has a high relaxation rate that leads to light emission, it is difficult for excitons to diffuse into the peripheral layer of the light emitting layer (for example, a hole transport layer or an electron transport layer). Light emission is expected. On the other hand, light emission from triplet excitons is spin-forbidden and has a slow relaxation rate, so that excitons are likely to diffuse into the peripheral layer, and thermal energy deactivation occurs from other than specific phosphorescent compounds. End up. That is, control of the recombination region of electrons and holes is more important than the fluorescent organic EL element.
- Patent Document 1 discloses a compound having at least two rings of dibenzothiophene and having an aromatic ring or a heteroaromatic ring as a linker site between the two dibenzothiophenes. In addition, it shows that a light emitting lifetime is long in an element using a compound having carbazole at the linker site as a host compound.
- Patent Document 2 discloses a compound having four or more aromatic rings and heteroaromatic rings, one of which is dibenzofuran or dibenzothiophene.
- an element using a compound having carbazole as a heteroaromatic ring as a host compound or an electron transport material exhibits high performance in terms of light emission efficiency and light emission lifetime.
- An object of the present invention is to provide an organic EL element that can be driven at a low voltage and has a long lifetime, and a material for an organic EL element that realizes the organic EL element.
- the organic compound of the present invention contains three or more specific condensed heteroaromatic rings, so that it is possible to improve the charge transport of the device and drive the device at a low voltage. . Further, by not including carbazole in the specific condensed heteroaromatic ring in the present invention, the ionization potential of the entire compound is increased. By using a compound having a large ionization potential as an electron transporting (hole blocking) layer in this way, it is expected that holes are retained in the light emitting layer and a decrease in light emission efficiency is prevented.
- a compound represented by the following formula (1) each independently represents O or S.
- Y 1 to Y 4 and Y 21 to Y 24 each independently represent C (Ra 1 ) or N.
- Y 5 to Y 12 one of Y 5 to Y 8 and one of Y 9 to Y 12 represent a carbon atom bonded to each other, and the other Y 5 to Y 12 are each independently And C (Ra 1 ) or N.
- Y 13 to Y 16 bonded to A 1 represents a carbon atom, and the other Y 13 to Y 16 each independently represents C (Ra 1 ) or N.
- Y 17 to Y 20 those bonded to A 1 represent a carbon atom, and the other Y 17 to Y 20 each independently represent C (Ra 1 ) or N.
- a 1 represents O, S, Si (Ar 1 ) (Ar 2 ), P ( ⁇ O) (Ar 3 ) (Ar 4 ), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted heteroarylene group having 5 to 30 ring atoms.
- n represents an integer of 1 to 4.
- Ar 1 to Ar 4 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
- Ra 1 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms.
- Rb and Rc are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted Represents an alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms.
- the compound of 1 represented by following formula (2).
- X 1 ⁇ X 3 are the same as X 1 ⁇ X 3 each formula (1).
- Y 1 to Y 4 , Y 9 , Y 10 , Y 12 , Y 13 , Y 15 , Y 16 and Y 21 to Y 24 each independently represent C (Ra 2 ) or N.
- One of Y 5 to Y 8 represents a single-bonded carbon atom, and the other Y 5 to Y 8 each independently represents C (Ra 2 ) or N.
- Y 17 to Y 20 those bonded to A 2 represent a carbon atom, and the other Y 17 to Y 20 each independently represent C (Ra 2 ) or N.
- a 2 represents O, S, Si (Ar 1 ) (Ar 2 ), P ( ⁇ O) (Ar 3 ) (Ar 4 ), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted heteroarylene group excluding a carbazolylene group having 5 to 30 ring-forming atoms.
- Ar 1 ⁇ Ar 4 is, n of each type (1), is the same as Ar 1 ⁇ Ar 4.
- Ra 2 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms other than a carbazole group, substituted or unsubstituted An alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon group having 1 to 30 carbon atoms.
- Rb and Rc are the same as Rb and Rc in formula (1), respectively.
- 3. The compound according to 2, which is represented by the following formula (3). [In Formula (3), Y 1 to Y 5 , Y 7 to Y 10 , Y 12 , Y 13 , Y 15 , Y 16 to Y 18 , Y 20 to Y 24 each independently represent C (Ra 2 ) or N. X 1 ⁇ X 3, A 2 , n, Ra 2 is X 1 ⁇ X 3 respectively formula (2), A 2, n , and Ra 2 same. ] 4). 3. The compound according to 3, which is represented by the following formula (4).
- X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 , and n are X 1 to X 3 and Y 1 in formula (3), respectively.
- Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 and n are the same.
- 5. 5 The compound according to any one of 1 to 4, wherein A 1 or A 2 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. 6). 5.
- a 1 or A 2 is a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms and excluding a carbazolylene group. 7).
- the compound according to 4 which is represented by the following formula (5). [In Formula (5), Z 1 to Z 4 each independently represent C (Ra 2 ) or N.
- X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , and Y 20 to Y 24 are respectively X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , and Y 20 to Y 24 are the same.
- Ra 2 is the same as Ra 2 of the formula (2).
- a material for an organic electroluminescence device comprising the compound according to any one of 1 to 7. 9.
- An organic electroluminescence device comprising one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers contains the material for an organic electroluminescence device according to 8. 10. 10. The organic electroluminescence device according to 9, wherein the light emitting layer contains the material for an organic electroluminescence device. 11. 11. The organic electroluminescence device according to 10, wherein the light emitting layer contains the material for an organic electroluminescence device as a host material of the light emitting layer. 12 12. The organic electroluminescence device according to any one of 9 to 11, which has an electron transport zone between the light emitting layer and the cathode, and the electron transport zone contains the material for an organic electroluminescence device. 13.
- the organic electroluminescent device according to any one of 9 to 12, wherein the light emitting layer contains a phosphorescent material.
- 14 The organic electroluminescence device according to 13, wherein the phosphorescent material is a compound containing a metal selected from iridium (Ir), osmium (Os), and platinum (Pt). 15.
- the organic electroluminescence device which has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer contains a nitrogen-containing heterocyclic derivative.
- the compound of the present invention has a structure in which a condensed heteroaromatic ring is further connected to a structure in which two or more condensed heteroaromatic rings are connected via an aromatic ring or a single atom.
- a condensed heteroaromatic ring By including three or more condensed heteroaromatic rings, the charge transportability is improved, and the device can be driven under a low voltage.
- such a structure has an effect that crystallinity can be reduced while the molecular skeleton is firm, and an element having few pixel defects and a long lifetime can be provided.
- the compound of the present invention is a compound represented by the following formula (1).
- Y 1 to Y 4 and Y 21 to Y 24 each independently represent C (Ra 1 ) or N.
- Y 5 to Y 12 one of Y 5 to Y 8 and one of Y 9 to Y 12 represent a carbon atom bonded to each other, and the other Y 5 to Y 12 are each independently And C (Ra 1 ) or N.
- Y 13 to Y 16 bonded to A 1 represents a carbon atom, and the other Y 13 to Y 16 each independently represents C (Ra 1 ) or N.
- Y 17 to Y 20 those bonded to A 1 represent a carbon atom, and the other Y 17 to Y 20 each independently represent C (Ra 1 ) or N.
- a 1 represents O, S, Si (Ar 1 ) (Ar 2 ), P ( ⁇ O) (Ar 3 ) (Ar 4 ), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted heteroarylene group having 5 to 30 ring atoms.
- n represents an integer of 1 to 4.
- Ar 1 to Ar 4 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
- Ra 1 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms.
- Rb and Rc are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted Represents an alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms.
- the compound of the present invention is preferably a compound represented by the following formula (2).
- X 1 to X 3 and n are as defined in formula (1).
- Y 1 to Y 4 , Y 9 , Y 10 , Y 12 , Y 13 , Y 15 , Y 16 and Y 21 to Y 24 each independently represent C (Ra 2 ) or N.
- One of Y 5 to Y 8 represents a single-bonded carbon atom, and the other Y 5 to Y 8 each independently represents C (Ra 2 ) or N.
- Y 17 to Y 20 those bonded to A 2 represent a carbon atom, and the other Y 17 to Y 20 each independently represent C (Ra 2 ) or N.
- a 2 represents O, S, Si (Ar 1 ) (Ar 2 ), P ( ⁇ O) (Ar 3 ) (Ar 4 ), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted heteroarylene group excluding a carbazolylene group having 5 to 30 ring-forming atoms.
- Ar 1 to Ar 4 are as defined in Formula (1).
- Ra 2 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms other than a carbazole group, substituted or unsubstituted An alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon group having 1 to 30 carbon atoms.
- the compound of the present invention is more preferably a compound represented by the following formula (3).
- Y 1 to Y 5 , Y 7 to Y 10 , Y 12 , Y 13 , Y 15 , Y 16 to Y 18 , and Y 20 to Y 24 are each independently C (Ra 2 ) , Or N.
- X 1 to X 3 , A 2 , n, and Ra 2 are as defined in Formula (2).
- the compound of the present invention is more preferably a compound represented by the following formula (4).
- connection position of the three fused aromatic rings By appropriately selecting the connection position of the three fused aromatic rings, high triplet energy that does not impair the luminous efficiency of the blue phosphorescent complex can be maintained, and a highly efficient organic EL device can be realized.
- X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 , and n are as defined in the formula (3). It is.
- a 1 and A 2 are preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- a 1 and A 2 are preferably substituted or unsubstituted heteroarylene groups having 5 to 20 ring atoms excluding the carbazole group.
- the molecule has a linear structure after having three or more condensed aromatic rings in the molecule, selecting these bonding positions appropriately, and maintaining high triplet energy that does not impair the luminous efficiency of the blue phosphorescent complex. By doing so, the molecular orientation is improved, and as a result, the charge transport property can be improved, and the device can be driven at a low voltage.
- the compound of the present invention is particularly preferably a compound represented by the following formula (5).
- Z 1 to Z 4 each independently represent C (Ra 2 ) or N.
- X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , and Y 20 to Y 24 are as defined in Formula (4).
- Ra 2 is as defined in Formula (2).
- aryl group or arylene group having 6 to 30 ring carbon atoms examples include monovalent groups (aryl groups) and divalent groups (arylene groups) of non-condensed aromatic rings and condensed aromatic rings. More specifically, a phenyl group, a naphthyl group, a phenanthryl group, a biphenylyl group, a terphenylyl group, a fluoranthenyl group, a triphenylenyl group, a phenanthrenyl group, a 9,9-dimethylfluorenyl group, and the like can be given.
- the ring-forming carbon number of the aryl group or arylene group is preferably 6 to 20, and more preferably 6 to 18.
- An aryloxy group having 6 to 30 ring carbon atoms is represented by —OX, and examples of X include the above aromatic hydrocarbon ring groups.
- the aryloxy group is, for example, a phenoxy group.
- heteroaryl group or heteroarylene group having 5 to 30 ring atoms examples include a monovalent group (heteroaryl group) or divalent group (heteroarylene group) of a non-condensed heteroaromatic ring and a condensed heteroaromatic ring.
- heteroaryl groups include pyrrolyl, pyrazinyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuran.
- alkyl group having 1 to 30 carbon atoms examples include linear or branched alkyl groups, and specifically include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec- Examples thereof include a butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, and a trifluoromethyl group, and preferably a methyl group, an ethyl group, a propyl group, and an isopropyl group.
- the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 3 to 6 carbon atoms.
- the alkoxy group having 1 to 30 carbon atoms is represented as —OY, and examples of Y include the above alkyl examples.
- the alkoxy group is, for example, a methoxy group, an ethoxy group, or a trifluoromethoxy group.
- Examples of the fluoroalkyl group having 1 to 30 carbon atoms include groups in which one or more fluorine atoms are substituted on the alkyl group having 1 to 20 carbon atoms described above. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, and a pentafluoroethyl group. Preferably, they are a trifluoromethyl group and a pentafluoroethyl group.
- Examples of the cycloalkyl group having 3 to 30 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Is a cyclopentyl group or a cyclohexyl group.
- the cycloalkyl group preferably has 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.
- Examples of the aralkyl group having 7 to 30 carbon atoms include those in which the above-described aryl group is substituted on the above-described alkyl group.
- the number of carbon atoms in the aralkyl group is preferably 7-20, and more preferably 7-18.
- the three condensed heteroaromatic rings of the formulas (1) to (5) may not be substituted (Ra 1 and Ra 2 are all hydrogen), and may have a substituent such as 1, 2 or 3 .
- examples of the substituent include an alkyl group having 1 to 30 carbon atoms, an alkoxy group or a fluoroalkyl group, an aryl group or aryloxy group having 6 to 30 ring carbon atoms, and a ring forming carbon number. And a heteroaryl group having 3 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, a silyl group, an alkylsilyl group having 1 to 6 carbon atoms, a fluoro group, or a cyano group.
- the organic EL device material of the present invention is characterized by containing the compound of the present invention.
- the organic EL device material of the present invention is useful as a phosphorescent organic EL device material, can be used for all colors of blue, green, and red, and is particularly useful as a blue material.
- the organic EL device material of the present invention is useful as a light emitting layer material, an electron transport material, a hole transport material, a hole barrier material, and the like. By using the organic EL element material of the present invention, an organic EL element having a low voltage and a long life can be obtained.
- Organic EL device of the present invention has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is the organic EL device material of the present invention or It contains the compound of the present invention (hereinafter also simply referred to as “organic EL device material”).
- organic EL device material By providing the organic thin film layer containing the organic EL element material of the present invention, low voltage driving is possible and an organic EL element having a long life can be obtained.
- the light emitting layer preferably contains the organic EL device material of the present invention, and more preferably as the host material of the light emitting layer.
- the organic EL device material of the present invention having high energy that does not impair the luminous efficiency of the phosphorescent complex is contained in the light emitting layer, the efficiency of the device is improved.
- the triplet energy of the host material used for the light emitting layer is preferably 2.9 eV or more.
- a hole barrier layer and an electron transport layer are provided in this order between the light emitting layer and the cathode, and the hole barrier layer between the light emitting layer and the electron transport layer is an organic material of the present invention. It preferably contains an EL element material.
- the organic EL device material of the present invention By including the organic EL device material of the present invention in the hole barrier layer, it becomes possible to improve the injection and transport of electrons to the light emitting layer, thereby obtaining the effect of reducing the drive voltage of the device. It is done. Moreover, as described above, the organic EL device material of the present invention has high energy that does not impair the light emission efficiency of the phosphorescent complex, thereby suppressing energy transfer from the light emitting layer, thereby leading to higher efficiency of the device. Specifically, the triplet energy of the material used for the hole blocking layer is preferably a triplet energy equivalent to that of the host material.
- the light emitting layer preferably contains a phosphorescent material
- the phosphorescent material is a metal selected from iridium (Ir), osmium (Os), and platinum (Pt).
- the compound containing a metal is more preferably an orthometalated metal complex.
- a reducing dopant is contained in the interface region between the cathode and the organic thin film layer. Specific examples of the reducing dopant will be described later.
- an electron injection layer is provided between the light emitting layer and the cathode, and the electron injection layer contains a nitrogen-containing heterocyclic derivative.
- the nitrogen-containing heterocycle will be described later.
- the organic EL device of the present invention has one or more organic thin film layers including a light emitting layer between a cathode and an anode, the light emitting layer contains a phosphorescent material, and at least one of the organic thin film layers.
- One layer contains the material for an organic EL device of the present invention.
- anode / hole transport zone (hole injection layer and / or hole transport layer) / light emitting layer / cathode
- anode / light emitting layer / electron transport zone (barrier layer and And / or electron transport layer and / or electron injection layer) / cathode
- anode / hole transport zone / light emitting layer / electron transport zone / cathode etc.
- the structure of the organic EL element can be a tandem element configuration having at least two organic layer units including a light emitting layer. Examples of the structure of the organic layer unit include a hole transport band / light-emitting layer, a light-emitting layer / electron transport band, and a hole transport band / light-emitting layer / electron transport band.
- An intermediate layer (also referred to as an intermediate conductive layer, a charge generation layer, or CGL) is interposed between the two light emitting layers, and an electron transport band can be provided for each unit.
- at least one light emitting layer is a phosphorescent light emitting layer.
- Examples of the specific stacking order of the tandem device configuration include anode / phosphorescent layer / intermediate layer / phosphorescent layer / electron transport band (preferably including a barrier layer) / cathode, anode / phosphorescent layer / electron transport.
- Band (preferably including a barrier layer) / intermediate layer / phosphorescent layer / cathode, anode / fluorescent layer / intermediate layer / phosphorescent layer / electron transport band (preferably including barrier layer) / cathode, anode / Phosphorescent layer / electron transport zone (preferably including a barrier layer) / intermediate layer / fluorescent layer / cathode, anode / phosphorescent layer / electron transport zone (preferably including barrier layer) / interlayer / phosphorescent layer Layer / electron transport zone (preferably including a barrier layer) / cathode and the like.
- the “hole injection / transport layer” is included in the embodiment of the hole transport layer.
- the light emitting layer may be a stacked body of a plurality of light emitting layers.
- the organic EL device of the present invention has a hole transport zone between the anode and the light emitting layer, and the light emitting layer or the hole transport zone contains the organic EL device material of the present invention.
- it has an electron transport zone between the light emitting layer and the cathode, and the electron transport zone may contain the organic EL device material of the present invention.
- the organic EL device material represented by the formula (1) is obtained by using the light emitting layer, the hole transport zone (hole transport layer, hole injection layer), the electron transport zone (electron transport). Layer, an electron injection layer, or a barrier layer), and more preferably at least in a light emitting layer or an electron transport zone.
- the organic EL device of the present invention preferably contains 50% by volume (v / v) or more of the material in the organic thin film layer containing the material for the organic EL device of the present invention, and 70% by volume (v / v). It is more preferable to contain above, and it is further more preferable to contain 90 volume% (v / v) or more.
- the electron transport band preferably has a barrier layer in a portion adjacent to the light emitting layer.
- the barrier layer prevents diffusion of triplet excitons generated in the light-emitting layer into the electron transport band, and confines the triplet excitons in the light-emitting layer, thereby eliminating the triplet exciton emission dopant.
- the organic EL device material of the present invention is used as a barrier layer in the electron transport zone, so that electrons are efficiently injected into the light emitting layer and triplet excitons are converted into electrons. It is presumed that it is possible to prevent energy deactivation in the transport zone. That is, it is presumed that it becomes easy to control the electron-hole recombination region by using the organic EL device material of the present invention for the barrier layer.
- the organic EL device material of the present invention also has high electrochemical stability with respect to hole injection and hole transport, if the organic EL device material of the present invention is used as a barrier layer, the electrical property of the barrier layer can be reduced. It is presumed that chemical deterioration can be prevented, and it is considered that an organic EL element excellent in durability can be obtained.
- the organic EL device material of the present invention is used as a barrier layer, if the triplet energy of the phosphorescent dopant in the light emitting layer is E T d and the triplet energy of the compound used as the barrier layer is E T TB , E T If the energy relationship of d ⁇ E T TB is satisfied, the energy deactivation route other than the emission of light on the dopant due to the triplet exciton of the phosphorescent dopant being confined (cannot move to other molecules) due to the energy relationship. It is estimated that light can be emitted with high efficiency.
- the energy difference ⁇ E T is preferably as large as possible relative to the thermal energy at room temperature, more preferably 0.1 eV or more, and particularly preferably 0.2 eV or more.
- ⁇ edge means that when the vertical axis represents phosphorescence intensity and the horizontal axis represents wavelength, and represents the phosphorescence spectrum, a tangent line is drawn with respect to the short wavelength side rise of the phosphorescence spectrum, It means the wavelength value (unit: nm) at the intersection of the horizontal axis.
- the host material for the light emitting layer is preferably a material satisfying A b ⁇ A h ⁇ 0.1 eV.
- a b represents the affinity of the barrier layer material
- a h represents the affinity of the light emitting layer host material.
- the affinity Af (electron affinity) in the present invention refers to energy released or absorbed when one electron is given to the molecule of the material, and is defined as positive in the case of emission and negative in the case of absorption.
- the affinity Af is defined as follows by the ionization potential Ip and the optical energy gap Eg (S).
- Af Ip-Eg (S)
- the ionization potential Ip means the energy required to remove and ionize electrons from the compound of each material.
- the ionization potential Ip is a positive value measured with an atmospheric photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). It is a value with the sign of.
- the optical energy gap Eg (S) refers to the difference between the conduction level and the valence level.
- the long wavelength side tangent and the baseline (zero absorption) of the ultraviolet / visible light absorption spectrum of the dilute dichloromethane solution of each material This is a value having a positive sign obtained by converting the wavelength value of the intersection point into energy.
- the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic thin film layer 10 disposed between the anode 3 and the cathode 4.
- the organic thin film layer 10 has a phosphorescent light emitting layer 5 containing a phosphorescent host as a host material and a phosphorescent dopant as a phosphorescent material.
- An electron injection / transport layer 7 or the like may be provided between the light emitting layer 5 and the cathode 4.
- an electron barrier layer may be provided on the phosphorescent light emitting layer 5 on the anode 3 side, and a hole barrier layer may be provided on the phosphorescent light emitting layer 5 on the cathode 4 side.
- the terms fluorescent host and phosphorescent host are referred to as a fluorescent host when combined with a fluorescent dopant, and are referred to as a phosphorescent host when combined with a phosphorescent dopant. It is not limited to fluorescent hosts or phosphorescent hosts.
- the fluorescent host means a material constituting the fluorescent light-emitting layer containing a fluorescent dopant, and does not mean a material that can be used only for the host of the fluorescent light-emitting material.
- the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean a material that can be used only as a host of the phosphorescent material.
- hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”
- electron injection / transport layer means “electron injection layer” And / or “at least one of the electron transport layers”.
- the organic EL device of the present invention is usually produced on a translucent substrate.
- the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
- the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
- the anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
- Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
- the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
- the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
- the cathode a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer, or the light emitting layer.
- the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
- the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
- the aspect which takes out light emission from a cathode side is also employable.
- the light emitting layer of the organic EL element has the following functions. That is, (1) Injection function; a function capable of injecting holes from an anode or a hole injection layer when an electric field is applied, and a function of injecting electrons from a cathode or an electron injection layer; (2) Transport function; function to move injected charges (electrons and holes) by the force of electric field, (3) Luminescent function; a function to provide a field for recombination of electrons and holes and connect this to light emission, There is.
- Injection function a function capable of injecting holes from an anode or a hole injection layer when an electric field is applied, and a function of injecting electrons from a cathode or an electron injection layer
- Transport function function to move injected charges (electrons and holes) by the force of electric field
- Luminescent function a function to provide a field for recombination of electrons and holes and connect this to light emission, There is.
- a known method such as an evaporation method, a spin coating method, or an LB method can be applied.
- the light emitting layer is preferably a molecular deposited film.
- the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Can be classified from a thin film (accumulated film) formed by the LB method according to a difference in an agglomerated structure and a higher-order structure and a functional difference resulting therefrom.
- the light emitting layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution, and then thinning the solution by a spin coating method or the like.
- the organic EL device of the present invention has one or more organic thin film layers including a light emitting layer between the cathode and the anode, and at least one layer of the organic thin film layer contains the organic EL device material of the present invention. .
- a plurality of light emitting layers it is preferable that at least one of the light emitting layers contains the organic EL element material of the present invention and at least one phosphorescent material.
- the organic EL device of the present invention contains an organometallic complex as a phosphorescent material, and the organometallic complex includes a metal atom selected from Ir, Pt, Os, Au, Be, Cu, Re, and Ru, a ligand It is preferable to have.
- the ligand preferably has an ortho metal bond.
- a compound containing a metal atom selected from Ir, Os and Pt is preferable in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved, and an iridium complex, an osmium complex, platinum Metal complexes such as complexes are more preferred, with iridium complexes and platinum complexes being more preferred, and orthometalated iridium complexes being most preferred. Specific examples of preferable organometallic complexes are shown below.
- At least one of the phosphorescent materials included in the light emitting layer has a maximum emission wavelength of 450 nm or more and 750 nm or less.
- the maximum value is 450 nm or more and 495 or less, 495 nm or more and 590 nm or less, and 590 nm or more and 750 nm or less.
- a highly efficient organic EL device can be obtained by forming a light emitting layer by doping a phosphorescent material (phosphorescent dopant) having such an emission wavelength into a specific host material used in the present invention.
- the organic EL device of the present invention preferably has at least one of an electron donating dopant and an organometallic complex in an interface region between the cathode and the organic thin film layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
- the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
- alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
- alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
- a work function of 2.9 eV or less is particularly preferable.
- the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
- alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
- alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
- the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
- the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
- the ligand includes quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- the electron donating dopant and the organometallic complex it is preferable to form a layer or an island in the interface region.
- a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material.
- a method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable.
- the dispersion concentration is usually organic substance: electron donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.
- At least one of the electron donating dopant and the organometallic complex is formed in a layered form
- at least one of the electron donating dopant and the organometallic complex is formed.
- These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
- an electron donating dopant and an organometallic complex is formed in an island shape
- a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
- the ratio of at least one of the main component (light-emitting material or electron injection material), the electron-donating dopant, and the organometallic complex is, as a molar ratio, the main component: the electron-donating dopant.
- / or organometallic complex 5: 1 to 1: 5, preferably 2: 1 to 1: 2.
- the electron injection layer or the electron transport layer is a layer that assists the injection of electrons into the light emitting layer, and has a high electron mobility.
- the electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level.
- the organic EL device of the present invention preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer preferably contains a nitrogen-containing ring derivative as a main component.
- the electron injection layer may be a layer that functions as an electron transport layer. “As a main component” means that the electron injection layer contains 50% by mass or more of a nitrogen-containing ring derivative.
- an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
- the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
- a nitrogen-containing ring metal chelate complex represented by the following formula (A) is preferable.
- R 2 to R 7 in the general formula (A) are each independently a hydrogen atom, a halogen atom, an oxy group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, Or it is an aromatic heterocyclic group, These may be substituted.
- the halogen atom include fluorine, chlorine, bromine, iodine and the like.
- the optionally substituted amino group include an alkylamino group, an arylamino group, and an aralkylamino group.
- the alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group.
- the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 . Specific examples of Q 1 and Q 2 are each independently the same as those described for the alkyl group and the aralkyl group, and preferred examples are also the same.
- the arylamino group is represented by —NAr 1 Ar 2, and specific examples of Ar 1 and Ar 2 are the same as those described for the non-condensed aromatic hydrocarbon group and the condensed aromatic hydrocarbon group, respectively. .
- M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
- L in the above formula (A) is a group represented by the following formula (A ′) or (A ′′).
- R 8 to R 12 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other form a cyclic structure. It may be.
- R 13 to R 27 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other have a cyclic structure. It may be formed. Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) include R 2 to R 7 in the formula (A).
- examples of the divalent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane-2,2
- examples include a '-diyl group, a diphenylethane-3,3'-diyl group, and a diphenylpropane-4,4'-diyl group.
- 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
- a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline) such as tris (8-quinolinol) aluminum is used.
- 8-quinolinol or 8-hydroxyquinoline such as tris (8-quinolinol
- Ar 17, Ar 18, Ar 19, Ar 21, Ar 22 and Ar 25 represents an or without an aromatic hydrocarbon group or fused aromatic hydrocarbon group having a substituent
- Ar 17 Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same as or different from each other.
- the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- substituent for these include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- Ar 20 , Ar 23 and Ar 24 each represent a divalent aromatic hydrocarbon group or a condensed aromatic hydrocarbon group with or without a substituent, and Ar 23 and Ar 24 may be the same or different from each other. Also good.
- the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
- substituent for these include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- electron transfer compounds those having good thin film forming properties are preferably used.
- Specific examples of these electron transfer compounds include the following.
- nitrogen-containing heterocyclic derivative as the electron transfer compound examples include nitrogen-containing compounds that are not metal complexes.
- a 5-membered or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C) can be given.
- X represents a carbon atom or a nitrogen atom.
- Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
- the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.
- the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.
- R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
- preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula.
- HAr-L 1 -Ar 1 -Ar 2 In the above formula, HAr is an optionally substituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms, and L 1 is a single bond or optionally having 6 to 40 carbon atoms. Or an aromatic heterocyclic group having 3 to 40 carbon atoms or a condensed aromatic heterocyclic group which may have a substituent, and Ar 1 represents a substituent.
- HAr is selected from the following group, for example.
- L 1 is selected from the following group, for example.
- Ar 1 is selected from, for example, the following arylanthranyl groups.
- R 1 to R 14 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, An aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms which may have a substituent, or an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, Ar 3 represents an optionally substituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, an aromatic heterocyclic group having 3 to 40 carbon atoms, or a condensed aromatic heterocyclic group. It is.
- Ar 2 is selected from the following group, for example.
- the following compounds are also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron transfer compound.
- R 1 to R 4 each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic cyclic group, or a substituted or unsubstituted carbocyclic aromatic ring group.
- X 1 and X 2 each independently represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.
- the following compounds are also preferably used as the electron transfer compound.
- R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula.
- R 5 , R 6 , R 7 , R 8 and R 9 are the same or different groups, and a hydrogen atom or at least one of them is a saturated or unsaturated alkoxyl group, an alkyl group, an amino group Or an alkylamino group.
- the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
- the electron transporting layer preferably contains at least one of nitrogen-containing heterocyclic derivatives represented by the following formulas (201) to (203).
- R has a hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms, a condensed aromatic hydrocarbon group, or a substituent.
- R 1 has an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, an optionally substituted pyridyl group, and a substituent.
- R 2 and R 3 each independently have a hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms, a condensed aromatic hydrocarbon group, or a substituent.
- An alkoxy group, L is an aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group which may have a substituent, a pyridinylene group which may have a substituent, or a substituent.
- Ar 1 has an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, an optionally substituted pyridinylene group, or a substituent.
- Ar 2 is an optionally substituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 60 carbon atoms, or an optionally substituted pyridyl group.
- Ar 3 has an aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group which may have a substituent, a pyridyl group which may have a substituent, or a substituent.
- R represents a hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms, a condensed aromatic hydrocarbon group, or a substituent.
- the film thickness of the electron injection layer or the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm.
- an insulator or a semiconductor as an inorganic compound as a constituent of the electron injection layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
- preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
- the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced.
- examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
- the preferred thickness of the layer is about 0.1 nm to 15 nm.
- the electron injection layer in this invention contains the above-mentioned reducing dopant, it is preferable.
- an aromatic amine compound for example, an aromatic amine derivative represented by the following general formula (I) is preferably used.
- Ar 1 to Ar 4 represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted nuclear atom number of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups are combined with aromatic heterocyclic groups or condensed aromatic heterocyclic groups .
- Specific examples of the compound of the general formula (I) are described below, but are not limited thereto.
- aromatic amine of the following general formula (II) is also suitably used for formation of a positive hole injection layer or a positive hole transport layer.
- the light emitting layer contains a charge injection auxiliary material.
- a light-emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light-emitting layer. It becomes difficult and the drive voltage for obtaining sufficient luminance may increase.
- by adding a hole injection / transport charge injection auxiliary agent to the light emitting layer hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.
- a general hole injection / transport material or the like can be used as the charge injection auxiliary agent.
- Specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, Examples include hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilanes, aniline copolymers, and conductive polymer oligomers (particularly thiophene oligomers).
- hole-injecting material examples include the above materials, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.
- NPD 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl
- MTDATA triphenylamine 4,4 ′, 4 ′′ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine
- a hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
- each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- the organic thin film layer containing the compound represented by the formula (1) used in the organic EL device of the present invention is prepared by vacuum evaporation, molecular beam evaporation (MBE), solution dipping in a solvent, spin It can be formed by a known method such as a coating method, a casting method, a bar coating method, a roll coating method or the like.
- each organic layer of the organic EL device of the present invention is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high applied voltage is required and the efficiency is deteriorated. Therefore, the range of several nm to 1 ⁇ m is usually preferable.
- hydrogen atoms contained in the compounds include isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
- Synthesis Example 1 (Synthesis of Compound (1)) (1) Synthesis of compound (1-a) In a three-necked flask, 269.1 g (1600 mmol) of dibenzofuran and 1280 mL of dichloromethane were placed, and the reactor was cooled to 0 ° C. under a nitrogen atmosphere. To the reactor, 100 mL of 204.6 g of bromine in dichloromethane was added dropwise over 40 minutes, followed by stirring at room temperature for 12 hours. After completion of the reaction, the reactor was cooled to 0 ° C., 500 mL of water was added, and 100 mL of 20% NaHSO 4 aqueous solution was further added.
- the sample solution was transferred to a separatory funnel and extracted several times with dichloromethane. This was washed with 300 mL of a 1N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated. This was dispersed and washed with hexane to obtain a white solid. The yield was 136 g, and the yield was 55%.
- Synthesis Example 2 (Synthesis of Compound (81)) (1) Synthesis of compound (81-a) Dibenzothiophene 15.0 g (81.4 mmol) and chloroform 90 mL were placed in a three-necked flask, and the reactor was cooled to 0 ° C. under a nitrogen atmosphere. To the reactor, 20 mL of a dichloromethane solution containing 13.1 g of bromine was dropped over 15 minutes, followed by stirring at room temperature for 12 hours. After completion of the reaction, the reactor was cooled to 0 ° C., 100 mL of water was added, and 30 mL of 20% NaHSO 4 aqueous solution was further added.
- the sample solution was transferred to a separatory funnel and extracted several times with dichloromethane. This was washed with 30 mL of 1N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. This was dispersed and washed with hexane and methanol to obtain a white solid. The yield was 10.7 g and the yield was 50%.
- Synthesis Example 3 (Synthesis of Compound (17)) (1) Synthesis of compound (17-a) In a three-necked flask, 100.1 g (575 mmol) of 2-bromo-3-hydroxypyridine, 88.5 g (632.5 mmol) of 2-fluorophenylboronic acid, 88.5 g (2300 mmol) of potassium carbonate, 1150 mL of N, N-dimethylacetamide, Pd (PPh 3 ) 4 13.3 g (11.5 mmol) was added, heated and stirred at 90 ° C. for 12 hours under a nitrogen atmosphere, and then heated and stirred at 160 ° C. for 8 hours.
- Synthesis Example 4 (Synthesis of Compound (129)) (1) Synthesis of compound (129-a) In a three-necked flask, 10.0 g (26.8 mmol) of compound (1-c), 8.62 g (30.8 mmol) of 3,5-dibromophenylboronic acid, 45 mL of 2M aqueous sodium carbonate solution, 90 mL of 1,2-dimethoxyethane, Pd (PPh 3 ) 4 1.55 g (1.34 mmol) was added, and the mixture was refluxed for 16 hours under a nitrogen atmosphere.
- Synthesis Example 5 (Synthesis of Compound (135)) (1) Synthesis of compound (135) In a three-necked flask, 2.50 g (5.20 mmol) of compound (129-a), 6.44 g (21.8 mmol) of compound (17-c), 30 mL of 2M aqueous sodium carbonate solution, 60 mL of 1,2-dimethoxyethane, Pd (PPh 3 ) 4 0.601 g (0.520 mmol) was added and refluxed for 16 hours under a nitrogen atmosphere.
- Synthesis Example 6 (Synthesis of Compound (144)) (1) Synthesis of compound (144-a) In a three-necked flask, 10.0 g (26.8 mmol) of compound (1-c), 6.82 g (32.2 mmol) of 3-bromophenylboronic acid, 50 mL of 2M aqueous sodium carbonate solution, 100 mL of 1,2-dimethoxyethane, Pd (PPh 3 ) 4 1.55 g (1.34 mmol) was added and refluxed for 12 hours under a nitrogen atmosphere. After completion of the reaction, the sample solution was transferred to a separating funnel and extracted several times with ethyl acetate.
- Synthesis Example 7 (Synthesis of Compound (9)) (1) Synthesis of compound (9) In a three-necked flask, 5.00 g (12.1 mmol) of compound (144-a), 4.58 g (12.1 mmol) of compound (144-b), 20 mL of 2M aqueous sodium carbonate, 40 mL of 1,2-dimethoxyethane, Pd (PPh 3 ) 4 1.40 g (1.21 mmol) was added and refluxed for 16 hours under a nitrogen atmosphere.
- Synthesis Example 8 (Synthesis of Compound (140)) (1) Synthesis of compound (140-a) A three-necked flask was charged with 168.1 g (1000 mmol) of dibenzofuran and 1600 ml of dichloromethane, and the reactor was cooled to 0 ° C. under a nitrogen atmosphere. After dropping 125 ml of bromine 255.8 g in dichloromethane into the reactor over 40 minutes, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reactor was cooled to 0 ° C., 500 ml of water was added, and 100 ml of a 20% NaHSO 4 aqueous solution was further added.
- the sample solution was transferred to a separatory funnel and extracted several times with dichloromethane. This was washed with 300 ml of 1N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated. This was dispersed and washed with hexane to obtain a white solid. The yield was 212 g and the yield was 65%.
- Synthesis Example 9 (Synthesis of Compound (145)) (1) Synthesis of compound (145-a) In a three-necked flask, 16.83 g (79.4 mmol) of compound (1-a), 18.81 g (79.4 mmol) of 3,5-dibromopyridine, 119 mL of 2M aqueous sodium carbonate solution, 119 mL of 1,2-dimethoxyethane, 119 mL of toluene, 2.75 g (2.38 mmol) of Pd (PPh 3 ) 4 was added and refluxed for 8 hours under an argon atmosphere. After completion of the reaction, the sample solution was transferred to a separating funnel and extracted several times with ethyl acetate.
- Example 1 A glass substrate with a 130 nm-thick ITO electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes.
- the glass substrate with the ITO electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound (HI1) is first thickened so as to cover the ITO electrode line on the surface on which the ITO electrode line is formed.
- the compound (HT1) was deposited by resistance heating at a thickness of 60 nm at a thickness of 20 nm, and thin films were sequentially formed. The film formation rate was 1 ⁇ / s. These thin films function as a hole injection layer and a hole transport layer, respectively.
- the compound (1) and the compound (BD1) were simultaneously heated by resistance heating to form a thin film having a thickness of 50 nm.
- the compound (BD1) was deposited so as to have a mass ratio of 20% with respect to the total mass of the compound (1) and the compound (BD1).
- the film formation rates were 1.2 ⁇ / s and 0.3 ⁇ / s, respectively.
- This thin film functions as a phosphorescent light emitting layer.
- a thin film having a thickness of 10 nm was formed on the phosphorescent light emitting layer by resistance heating vapor deposition of the compound (H1).
- the film formation rate was 1.2 liter / s. This thin film functions as a barrier layer.
- a thin film having a thickness of 10 nm was formed on this barrier layer by resistance heating vapor deposition of the compound (ET1).
- the film formation rate was 1 ⁇ / s.
- This film functions as an electron injection layer.
- LiF having a film thickness of 1.0 nm was deposited on the electron injection layer at a film formation rate of 0.1 ⁇ / s.
- metallic aluminum was vapor-deposited on the LiF film at a deposition rate of 8.0 ⁇ / s to form a metal cathode with a film thickness of 80 nm to obtain an organic EL element.
- the organic EL device obtained as described above was evaluated by the following method.
- External quantum efficiency (%) The external quantum efficiency at a luminance of 1000 cd / m 2 under a dry nitrogen gas atmosphere at 23 ° C. was measured using a luminance meter (Spectral Luminance Radiometer CS-1000 manufactured by Minolta).
- Half life (hours) A continuous energization test (DC) was performed at an initial luminance of 1000 cd / m 2 and the time until the initial luminance was reduced by half was measured.
- DC continuous energization test
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that the light emitting layer was formed using the compounds shown in Table 1 instead of using the compound (1).
- the obtained organic EL device was evaluated in the same manner as in Example 1, and the results are shown in Table 1.
- Example 6 the compound (H1) was used instead of the compound (1) as the phosphorescent light emitting layer material, and the compounds shown in Table 2 were used as the hole blocking layer material instead of the compound (H1).
- An organic EL device was produced in the same manner as in Example 1 except that the hole barrier layer was formed.
- Table 2 shows that the use of the compound of the present invention for the hole blocking layer of the organic EL device extended the lifetime of the device as compared with Comparative Examples 3 and 4.
- Table 3 shows triplet energies of the organic EL device materials used in Examples and Comparative Examples.
- the organic EL device of the present invention is compound (1), (17), (81), (129), (135), (144), (9) which is the material for the organic EL device of the present invention.
- the present invention is useful as a long-life organic EL element capable of driving an element under a low voltage and having excellent heat resistance, and a material for an organic EL element that realizes it.
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Abstract
Description
まず、燐光発光は、三重項励起子を利用した発光であるため、発光層に用いる化合物のエネルギーギャップが大きくなくてはならない。何故なら、ある化合物のエネルギーギャップ(以下、一重項エネルギーともいう。)の値は、通常、その化合物の三重項エネルギー(本発明では、最低励起三重項状態と基底状態とのエネルギー差をいう。)の値よりも大きいからである。
このように、従来の有機EL素子の素子設計思想に基づく場合、蛍光型の有機EL素子に用いる化合物と比べて大きなエネルギーギャップを有する化合物を燐光型の有機EL素子に用いることにつながり、有機EL素子全体の駆動電圧が上昇する。
特に、青色発光する燐光型の有機EL素子の場合、緑~赤色発光する燐光型の有機EL素子と比べて、発光層やその周辺層に三重項エネルギーが大きい化合物を使用することが好ましい。高い三重項エネルギーを有しながら、その他、有機EL材料として求められる性能を満たす化合物を得るためには、複素環化合物等の三重項エネルギーの高い分子パーツを単純に組み合わせるのではなく、π電子の電子状態を考慮した新たな思想による分子設計が必要になる。
特許文献2では、芳香環,複素芳香環を4環以上有し、そのうち1つの環がジベンゾフラン若しくはジベンゾチオフェンである化合物が示されている。中でも、複素芳香環としてカルバゾールを有する化合物をホスト化合物若しくは電子輸送材料として用いた素子が、発光効率、発光寿命の点において高性能であることを示す。
また、本発明における特定の縮合複素芳香環にカルバゾールを含まないとすることにより、化合物全体のイオン化ポテンシャルが大きくなる。このようにイオン化ポテンシャルの大きい化合物を電子輸送(正孔阻止)層として用いることにより、正孔を発光層に留め、発光効率の低下を防ぐことが期待される。
1.下記式(1)で表される化合物。
X1~X3は、それぞれ独立して、O,又はSを表す。
Y1~Y4及びY21~Y24は、それぞれ独立して、C(Ra1),又はNを表す。
Y5~Y12のうち、Y5~Y8のうち一つと、Y9~Y12のうち一つは、互いに結合する炭素原子を表し、それ以外のY5~Y12は、それぞれ独立して、C(Ra1),又はNを表す。
Y13~Y16のうちA1に結合するものは、炭素原子を表し、それ以外のY13~Y16は、それぞれ独立して、C(Ra1),又はNを表す。
Y17~Y20のうちA1に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra1),又はNを表す。
A1は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリーレン基を表す。
nは、1~4の整数を表す。
Ar1~Ar4は、それぞれ独立して置換若しくは無置換の環形成炭素数6~30のアリール基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリール基を表す。
Ra1は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、それぞれ独立して、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基、置換若しくは無置換の炭素数1~30のアルキル基、又は置換若しくは無置換の炭素数1~30のフルオロアルキル基を表す。]
2.下記式(2)で表される1記載の化合物。
X1~X3は、それぞれ式(1)のX1~X3と同じである。
Y1~Y4、Y9、Y10、Y12、Y13、Y15、Y16及びY21~Y24は、それぞれ独立して、C(Ra2),又はNを表す。
Y5~Y8のうち一つは、単結合する炭素原子を表し、それ以外のY5~Y8は、それぞれ独立して、C(Ra2),又はNを表す。
Y17~Y20のうちA2に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra2),又はNを表す。
A2は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30の、カルバゾリレン基を除くヘテロアリーレン基を表す。
n,Ar1~Ar4は、それぞれ式(1)のn,Ar1~Ar4と同じである。
Ra2は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30の、カルバゾール基を除くヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、それぞれ式(1)のRb,Rcと同じである。]
3.下記式(3)で表される2記載の化合物。
Y1~Y5、Y7~Y10、Y12、Y13、Y15、Y16~Y18、Y20~Y24は、それぞれ独立して、C(Ra2),又はNを表す。
X1~X3、A2、n、Ra2は、それぞれ式(2)のX1~X3、A2、n、Ra2と同じである。]
4.下記式(4)で表される3記載の化合物。
X1~X3、Y1~Y5、Y7、Y8、Y17、Y18、Y20~Y24、A2、nは、それぞれ式(3)のX1~X3、Y1~Y5、Y7、Y8、Y17、Y18、Y20~Y24、A2、nと同じである。]
5.前記A1又はA2が、置換若しくは無置換の環形成炭素数6~30のアリーレン基である1~4のいずれかに記載の化合物。
6.前記A1又はA2が、置換若しくは無置換の環形成原子数5~20の、カルバゾリレン基を除くヘテロアリーレン基である1~4のいずれかに記載の化合物。
7.下記式(5)で表される4記載の化合物。
Z1~Z4は、それぞれ独立して、C(Ra2),又はNを表す。
X1~X3、Y1~Y5、Y7、Y8、Y17、Y18、及びY20~Y24は、それぞれ式(4)のX1~X3、Y1~Y5、Y7、Y8、Y17、Y18、及びY20~Y24と同じである。Ra2は、式(2)のRa2と同じである。]
8.1~7のいずれかに記載の化合物を含む有機エレクトロルミネッセンス素子用材料。
9.陰極と陽極との間に、発光層を含む1以上の有機薄膜層を有し、前記有機薄膜層の少なくとも1層が、8に記載の有機エレクトロルミネッセンス素子用材料を含有する有機エレクトロルミネッセンス素子。
10.前記発光層が、前記有機エレクトロルミネッセンス素子用材料を含有する9に記載の有機エレクトロルミネッセンス素子。
11.前記発光層が、前記有機エレクトロルミネッセンス素子用材料を、発光層のホスト材料として含有する10に記載の有機エレクトロルミネッセンス素子。
12.前記発光層と前記陰極との間に電子輸送帯域を有し、該電子輸送帯域が前記有機エレクトロルミネッセンス素子用材料を含有する9~11のいずれかに記載の有機エレクトロルミネッセンス素子。
13.前記発光層が、燐光発光性材料を含有する9~12のいずれかに記載の有機エレクトロルミネッセンス素子。
14.前記燐光発光性材料が、イリジウム(Ir),オスミウム(Os)及び白金(Pt)から選ばれる金属を含有する化合物である13に記載の有機エレクトロルミネッセンス素子。
15.前記金属を含有する化合物が、オルトメタル化金属錯体である14に記載の有機エレクトロルミネッセンス素子。
16.前記発光層と前記陰極との間に電子注入層を有し、前記電子注入層が含窒素複素環誘導体を含有する9~15のいずれかに記載の有機エレクトロルミネッセンス素子。
本発明の化合物は、下記式(1)で表される化合物である。
Y1~Y4及びY21~Y24は、それぞれ独立して、C(Ra1),又はNを表す。
Y5~Y12のうち、Y5~Y8のうち一つと、Y9~Y12のうち一つは、互いに結合する炭素原子を表し、それ以外のY5~Y12は、それぞれ独立して、C(Ra1),又はNを表す。
Y13~Y16のうちA1に結合するものは、炭素原子を表し、それ以外のY13~Y16は、それぞれ独立して、C(Ra1),又はNを表す。
Y17~Y20のうちA1に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra1),又はNを表す。
A1は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリーレン基を表す。
nは、1~4の整数を表す。
Ar1~Ar4は、それぞれ独立して置換若しくは無置換の環形成炭素数6~30のアリール基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリール基を表す。
Ra1は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、それぞれ独立して、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基、置換若しくは無置換の炭素数1~30のアルキル基、又は置換若しくは無置換の炭素数1~30のフルオロアルキル基を表す。
X1~X3及びnは、式(1)で定義した通りである。
Y1~Y4、Y9、Y10、Y12、Y13、Y15、Y16及びY21~Y24は、それぞれ独立して、C(Ra2),又はNを表す。
Y5~Y8のうち一つは、単結合する炭素原子を表し、それ以外のY5~Y8は、それぞれ独立して、C(Ra2),又はNを表す。
Y17~Y20のうちA2に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra2),又はNを表す。
A2は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30の、カルバゾリレン基を除くヘテロアリーレン基を表す。
Ar1~Ar4は、式(1)で定義した通りである。
Ra2は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30の、カルバゾール基を除くヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、式(1)で定義した通りである。
X1~X3、A2、n、Ra2は、式(2)で定義した通りである。
また、上記式(1)~(4)におけるA1及びA2は、置換若しくは無置換の、カルバゾール基を除く環形成原子数5~20のヘテロアリーレン基であることが好ましい。
X1~X3、Y1~Y5、Y7、Y8、Y17、Y18、及びY20~Y24は、式(4)で定義した通りである。Ra2は、式(2)で定義した通りである。
環形成炭素数6~30のアリール基又はアリーレン基としては、非縮合芳香族環及び縮合芳香族環の1価の基(アリール基)又は2価の基(アリーレン基)が挙げられる。より具体的には、フェニル基、ナフチル基、フェナントリル基、ビフェニリル基、ターフェニリル基、フルオランテニル基、トリフェニレニル基、フェナントレニル基、9,9-ジメチルフルオレニル基等が挙げられる。アリール基又はアリーレン基の環形成炭素数は、6~20であることが好ましく、6~18であることがより好ましい。
本発明の有機EL素子用材料は、発光層材料、電子輸送性材料、正孔輸送性材料、正孔障壁材料等として有用である。
本発明の有機EL素子用材料を用いることにより、低電圧、かつ長寿命な有機EL素子が得られる。
本発明の有機EL素子は、陰極と陽極との間に、発光層を含む1以上の有機薄膜層を有し、前記有機薄膜層の少なくとも1層が、上記本発明の有機EL素子用材料又は本発明の化合物(以下単に「有機EL素子用材料」ともいう)を含有することを特徴とする。
本発明の有機EL素子用材料を含有する有機薄膜層を設けることによって、低電圧駆動が可能であり、長寿命な有機EL素子が得られる。
本発明の有機EL素子は、陰極と陽極との間に、発光層を含む一層以上の有機薄膜層を有し、この発光層が燐光発光性材料を含有し、また、この有機薄膜層の少なくとも一層が、本発明の有機EL素子用材料を含有する。
また、有機EL素子の構造は、発光層を含む有機層ユニットを少なくとも2つ有するタンデム素子構成とすることができる。有機層ユニットの構造としては、正孔輸送帯域/発光層、発光層/電子輸送帯域、正孔輸送帯域/発光層/電子輸送帯域が挙げられる。
本発明の有機EL素子は、上述のように、陽極と発光層との間に正孔輸送帯域を有し、発光層又は正孔輸送帯域が本発明の有機EL素子用材料を含有してもよく、また、発光層と前記陰極との間に電子輸送帯域を有し、電子輸送帯域が本発明の有機EL素子用材料を含有してもよい。
本発明の有機EL素子は、本発明の有機EL素子用材料を含む有機薄膜層において、該材料を50体積%(v/v)以上で含有することが好ましく、70体積%(v/v)以上で含有することがより好ましく、90体積%(v/v)以上で含有することがさらに好ましい。
本発明におけるアフィニティAf(電子親和力)とは、材料の分子に電子を一つ与えた時に放出又は吸収されるエネルギーをいい、放出の場合は正、吸収の場合は負と定義する。アフィニティAfは、イオン化ポテンシャルIpと光学エネルギーギャップEg(S)とにより次のように規定する。
Af=Ip-Eg(S)
ここで、イオン化ポテンシャルIpは、各材料の化合物から電子を取り去ってイオン化するために要するエネルギーを意味し、本発明では大気中光電子分光装置(AC-3、理研計器株式会社製)で測定した正の符号を持つ値である。光学エネルギーギャップEg(S)は、伝導レベルと価電子レベルとの差をいい、本発明では各材料のジクロロメタン希薄溶液の紫外・可視光吸収スペクトルの長波長側接線とベースライン(吸収ゼロ)との交点の波長値をエネルギーに換算して求めた正の符号を持つ値である。
有機EL素子1は、透明な基板2と、陽極3と、陰極4と、陽極3と陰極4との間に配置された有機薄膜層10と、を有する。
有機薄膜層10は、ホスト材料としての燐光ホスト及び燐光材料としての燐光ドーパントを含む燐光発光層5を有するが、燐光発光層5と陽極3との間に正孔注入・輸送層6等、燐光発光層5と陰極4との間に電子注入・輸送層7等を備えていてもよい。
また、燐光発光層5の陽極3側に電子障壁層を、燐光発光層5の陰極4側に正孔障壁層を、それぞれ設けてもよい。
これにより、電子や正孔を燐光発光層5に閉じ込めて、燐光発光層5における励起子の生成確率を高めることができる。
言い換えると、本明細書において、蛍光ホストとは、蛍光ドーパントを含有する蛍光発光層を構成する材料を意味し、蛍光発光材料のホストにしか利用できないものを意味しているわけではない。
同様に燐光ホストとは、燐光ドーパントを含有する燐光発光層を構成する材料を意味し、燐光材料のホストにしか利用できないものを意味しているわけではない。
本発明の有機EL素子は、通常、透光性の基板上に作製する。ここでいう透光性基板は有機EL素子を支持する基板であり、400nm~700nmの可視領域の光の透過率が50%以上で平滑な基板が好ましい。
具体的には、ガラス板、ポリマー板等が挙げられる。
ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を原料として用いてなるものを挙げられる。
またポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を原料として用いてなるものを挙げることができる。
有機EL素子の陽極は、正孔を正孔注入層、正孔輸送層又は発光層に注入する役割を担うものであり、4.5eV以上の仕事関数を有することが効果的である。
陽極材料の具体例としては、酸化インジウム錫合金(ITO)、酸化錫(NESA)、酸化インジウム亜鉛酸化物、金、銀、白金、銅等が挙げられる。
陽極はこれらの電極物質を蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。
発光層からの発光を陽極から取り出す場合、陽極の可視領域の光の透過率を10%より大きくすることが好ましい。また、陽極のシート抵抗は、数百Ω/□以下が好ましい。陽極の膜厚は、材料にもよるが、通常10nm~1μm、好ましくは10nm~200nmの範囲で選択される。
陰極材料は特に限定されないが、具体的にはインジウム、アルミニウム、マグネシウム、マグネシウム-インジウム合金、マグネシウム-アルミニウム合金、アルミニウム-リチウム合金、アルミニウム-スカンジウム-リチウム合金、マグネシウム-銀合金等が使用できる。
陰極も、陽極と同様に、蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。また、陰極側から、発光を取り出す態様を採用することもできる。
有機EL素子の発光層は以下の機能を併せ持つものである。
即ち、
(1)注入機能;電界印加時に陽極又は正孔注入層より正孔を注入することができ、陰極又は電子注入層より電子を注入することができる機能、
(2)輸送機能;注入した電荷(電子と正孔)を電界の力で移動させる機能、
(3)発光機能;電子と正孔の再結合の場を提供し、これを発光につなげる機能、
がある。
この発光層を形成する方法としては、例えば蒸着法、スピンコート法、LB法等の公知の方法を適用することができる。
ここで分子堆積膜とは、気相状態の材料化合物から沈着され形成された薄膜や、溶液状態又は液相状態の材料化合物から固体化され形成された膜のことであり、通常この分子堆積膜は、LB法により形成された薄膜(分子累積膜)とは凝集構造、高次構造の相違や、それに起因する機能的な相違により区分することができる。
また、樹脂等の結着剤と材料化合物とを溶剤に溶かして溶液とした後、これをスピンコート法等により薄膜化することによっても、発光層を形成することができる。
本発明の有機EL素子は、燐光材料として有機金属錯体を含有し、この有機金属錯体は、Ir,Pt,Os,Au,Be,Cu,Re及びRuから選択される金属原子と、配位子と、を有することが好ましい。特に、前記配位子は、オルトメタル結合を有することが好ましい。
燐光量子収率が高く、発光素子の外部量子効率をより向上させることができるという点で、Ir,Os及びPtから選ばれる金属原子を含有する化合物であると好ましく、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体であるとさらに好ましく、中でもイリジウム錯体及び白金錯体がより好ましく、オルトメタル化イリジウム錯体が最も好ましい。
好ましい有機金属錯体の具体例を、以下に示す。
このような発光波長の燐光材料(燐光ドーパント)を、本発明で用いる特定のホスト材料にドープして発光層を構成することにより、高効率な有機EL素子とできる。
本発明の有機EL素子は、陰極と有機薄膜層との界面領域に電子供与性ドーパント及び有機金属錯体の少なくともいずれかを有することも好ましい。
このような構成によれば、有機EL素子における発光輝度の向上や長寿命化が図られる。
電子供与性ドーパントとしては、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属化合物、希土類金属、及び希土類金属化合物などから選ばれた少なくとも一種類が挙げられる。
有機金属錯体としては、アルカリ金属を含む有機金属錯体、アルカリ土類金属を含む有機金属錯体、及び希土類金属を含む有機金属錯体などから選ばれた少なくとも一種類が挙げられる。
アルカリ土類金属としては、カルシウム(Ca)(仕事関数:2.9eV)、ストロンチウム(Sr)(仕事関数:2.0eV以上2.5eV以下)、バリウム(Ba)(仕事関数:2.52eV)などが挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
希土類金属としては、スカンジウム(Sc)、イットリウム(Y)、セリウム(Ce)、テルビウム(Tb)、イッテルビウム(Yb)などが挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
以上の金属のうち好ましい金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子における発光輝度の向上や長寿命化が可能である。
アルカリ土類金属化合物としては、酸化バリウム(BaO)、酸化ストロンチウム(SrO)、酸化カルシウム(CaO)及びこれらを混合したストロンチウム酸バリウム(BaxSr1-xO)(0<x<1)、カルシウム酸バリウム(BaxCa1-xO)(0<x<1)などが挙げられ、BaO、SrO、CaOが好ましい。
希土類金属化合物としては、フッ化イッテルビウム(YbF3)、フッ化スカンジウム(ScF3)、酸化スカンジウム(ScO3)、酸化イットリウム(Y2O3)、酸化セリウム(Ce2O3)、フッ化ガドリニウム(GdF3)、フッ化テルビウム(TbF3)などが挙げられ、YbF3、ScF3、TbF3が好ましい。
電子注入層又は電子輸送層は、発光層への電子の注入を助ける層であって、電子移動度が大きい。電子注入層はエネルギーレベルの急な変化を緩和する等、エネルギーレベルを調整するために設ける。
本発明の有機EL素子は、発光層と陰極との間に電子注入層を有し、前記電子注入層は、含窒素環誘導体を主成分として含有することが好ましい。ここで、電子注入層は電子輸送層として機能する層であってもよい。
尚、「主成分として」とは、電子注入層が50質量%以上の含窒素環誘導体を含有していることを意味する。
この含窒素環誘導体としては、例えば、下記式(A)で表される含窒素環金属キレート錯体が好ましい。
ハロゲン原子としては、例えば、フッ素、塩素、臭素、ヨウ素等が挙げられる。また、置換されていてもよいアミノ基の例としては、アルキルアミノ基、アリールアミノ基、アラルキルアミノ基が挙げられる。
アリールアミノ基は-NAr1Ar2と表され、Ar1及びAr2の具体例としては、それぞれ独立に前記非縮合芳香族炭化水素基及び縮合芳香族炭化水素基で説明した基と同様である。
上記式(A)のLは、下記式(A’)又は(A”)で表される基である。
前記式(A’)及び式(A”)のR8~R12及びR13~R27が示す炭素数1~40の炭化水素基としては、前記式(A)中のR2~R7の具体例と同様のものが挙げられる。
また、R8~R12及びR13~R27の互いに隣接する基が環状構造を形成した場合の2価の基としては、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ジフェニルメタン-2,2’-ジイル基、ジフェニルエタン-3,3’-ジイル基、ジフェニルプロパン-4,4’-ジイル基等が挙げられる。
Ar20、Ar23及びAr24は、それぞれ置換基を有する若しくは有さない2価の芳香族炭化水素基又は縮合芳香族炭化水素基を示し、Ar23とAr24は、互いに同一でも異なっていてもよい。
2価の芳香族炭化水素基又は縮合芳香族炭化水素基としては、フェニレン基、ナフチレン基、ビフェニレン基、アントラニレン基、ペリレニレン基、ピレニレン基等が挙げられる。そして、これらへの置換基としては炭素数1~10のアルキル基、炭素数1~10のアルコキシ基又はシアノ基等が挙げられる。
HAr-L1-Ar1-Ar2
前記式中、HArは、置換基を有していてもよい炭素数3~40の含窒素複素環基であり、L1は単結合、置換基を有していてもよい炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換基を有していてもよい炭素数3~40の芳香族複素環基又は縮合芳香族複素環基であり、Ar1は置換基を有していてもよい炭素数6~40の2価の芳香族炭化水素基であり、Ar2は置換基を有していてもよい炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換基を有していてもよい炭素数3~40の芳香族複素環基又は縮合芳香族複素環基である。
nは0~4の整数であり、
R1は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、又は炭素数1~20のアルコキシ基であり、
R2及びR3は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、又は置換基を有していてもよい炭素数1~20のアルコキシ基であり、
Lは、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジニレン基、置換基を有していてもよいキノリニレン基、又は置換基を有していてもよいフルオレニレン基であり、
Ar1は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジニレン基又は置換基を有していてもよいキノリニレン基であり、Ar2は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、又は置換基を有していてもよい炭素数1~20のアルコキシ基である。
尚、前記式(201)~(203)において、Rは、水素原子、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、又は置換基を有していてもよい炭素数1~20のアルコキシ基である。
また、電子注入層の構成成分として、含窒素環誘導体の他に無機化合物として、絶縁体又は半導体を使用することが好ましい。電子注入層が絶縁体や半導体で構成されていれば、電流のリークを有効に防止して、電子注入性を向上させることができる。
このような絶縁体又は半導体を使用する場合、その層の好ましい厚みは、0.1nm~15nm程度である。また、本発明における電子注入層は、前述の還元性ドーパントを含有していても好ましい。
前記一般式(I)の化合物の具体例を以下に記すが、これらに限定されるものではない。
例えば次のような変更も本発明の好適な変形例である。
エネルギーギャップが広いホスト材料を用いて発光層を形成した場合、ホスト材料のイオン化ポテンシャル(Ip)と正孔注入・輸送層等のIpとの差が大きくなり、発光層への正孔の注入が困難となり、十分な輝度を得るための駆動電圧が上昇するおそれがある。
このような場合、発光層に、正孔注入・輸送性の電荷注入補助剤を含有させることで、発光層への正孔注入を容易にし、駆動電圧を低下させることができる。
具体例としては、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、ポリシラン系、アニリン系共重合体、導電性高分子オリゴマー(特にチオフェンオリゴマー)等を挙げることができる。
また、ヘキサアザトリフェニレン誘導体等も正孔注入性の材料として好適に用いることができる。
本発明の有機EL素子の各層の形成方法は特に限定されない。従来公知の真空蒸着法、スピンコーティング法等による形成方法を用いることができる。本発明の有機EL素子に用いる、前記式(1)で表される化合物を含有する有機薄膜層は、真空蒸着法、分子線蒸着法(MBE法)あるいは溶媒に解かした溶液のディッピング法、スピンコーティング法、キャスティング法、バーコート法、ロールコート法等の塗布法による公知の方法で形成することができる。
(1)化合物(1-a)の合成
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=50:1)で精製し、白色の固体を得た。収量は3.65g、収率は35%であった。
反応終了後、試料反応溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、酢酸エチルを加え分散洗浄を行った。得られた固体をトルエンにて再結晶を行い、白色固体を得た。同定はFD/MSによる分子量測定によって行い、分子量576に対してm/e=576であった。収量は3.06g、収率は61%であった。
(1)化合物(81-a)の合成
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=50:1)で精製し、白色の固体を得た。収量は2.44g、収率は20%であった。
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量624に対してm/e=624であった。収量は1.64g、収率は55%であった。
(1)化合物(17-a)の合成
反応終了後、室温まで冷却した後、試料溶液にトルエン1L、水1Lを加え、分液ロートに移してよく振り、トルエン相を回収し、水相からトルエンで数回抽出した。このトルエン溶液をさらに水で数回洗浄した後、無水硫酸マグネシウムで乾燥し、シリカゲルショートカラムを通し、濃縮した。得られた試料をヘキサン200mLから再結晶して薄く黄色を帯びた固体を得た。
同定は1H-NMRによって行った。収量は54.4g、収率は56%であった。
反応終了後、室温まで冷却した後、試料溶液を氷水浴で冷やしながらチオ硫酸ナトリウム水溶液を加えて残存臭素を失活させ、さらに水酸化ナトリウム水溶液を加えて水相がpH10になるよう調整した。溶液を分液ロートに移し、トルエンにて数回抽出した。これを無水硫酸マグネシウムで乾燥し、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ジクロロメタン:酢酸エチル=8:2)にて精製し、得られた試料をヘキサンで分散洗浄、ろ取、真空乾燥(40℃、6時間)して薄く黄色を帯びた固体を得た。
同定は1H-NMRによって行った。収量は32.1g、収率は42%であった。
反応終了後、セライトろ過を行い、水300mLを加え、試料溶液を分液ロートに移した。トルエンにて数回抽出した後、これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:酢酸エチル=1:5)を行った後、ヘキサンにて再結晶することで白色固体を得た。収量は4.20g、収率は20%であった。
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、酢酸エチルを加え分散洗浄を行い、得られた固体をトルエンにて再結晶を行い、白色固体を得た。同定はFD/MSによる分子量測定によって行い、分子量578に対してm/e=578であった。収量は2.00g、収率は55%であった。
(1)化合物(129-a)の合成
反応終了後、試料溶液にヘキサン50ml,メタノール50mlを加えて、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、酢酸エチルを加え分散洗浄を行い、得られた固体をトルエンにて再結晶を行い、白色固体を得た。同定はFD/MSによる分子量測定によって行った。収量は6.50g、収率は50%であった。
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量742に対してm/e=742であった。収量は1.65g、収率は30%であった。
(1)化合物(135)の合成
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量745に対してm/e=745であった。収量は1.50g、収率は39%であった。
(1)化合物(144-a)の合成
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:酢酸エチル=20:1)で精製し、白色の固体を得た。収量は6.32g、収率は59%であった。
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量742に対してm/e=742であった。収量は1.74g、収率は22%であった。
(1)化合物(9)の合成
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量666に対してm/e=666であった。収量は6.05g、収率は75%であった。
(1) 化合物(140-a)の合成
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン)で精製し、白色の固体を得た。収量は12.0g、収率は60%であった。
反応終了後、試料溶液にメタノール100mLを加え、超音波洗浄を10分間行った後、析出試料をろ取し、メタノール、水、ヘキサンにて洗浄した。試料を乾燥させた後、再度、ヘキサン:酢酸エチル=1:1混合溶媒を加え、超音波洗浄30分間行い、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量728に対してm/e=728であった。収量は1.28g、収率は27%であった。
(1)化合物(145-a)の合成
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=1:5)で精製し、白色の固体を得た。収量は14.62g、収率は56%であった。
反応終了後、試料溶液を分液ロートに移し、酢酸エチルにて数回抽出した。これを無水硫酸マグネシウムで乾燥、ろ過、濃縮した。これをシリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン:酢酸エチル=2:20:1)で精製し、白色の固体を得た。同定はFD/MSによる分子量測定によって行い、分子量577に対してm/e=577であった。収量は1.29g、収率は27%であった。
膜厚130nmのITO電極ライン付きガラス基板(ジオマティック社製)を、イソプロピルアルコール中で5分間、超音波洗浄した後、UVオゾン洗浄を30分間行なった。
洗浄後のITO電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まずITO電極ラインが形成されている側の面上に、ITO電極ラインを覆うようにして化合物(HI1)を厚さ20nmで、次いで化合物(HT1)を厚さ60nmで抵抗加熱蒸着し、順次薄膜を成膜した。成膜レートは1Å/sとした。これらの薄膜は、それぞれ正孔注入層及び正孔輸送層として機能する。
次に、正孔注入・輸送層上に、化合物(1)と化合物(BD1)を同時に抵抗加熱蒸着して膜厚50nmの薄膜を成膜した。このとき、化合物(BD1)を、化合物(1)と化合物(BD1)の総質量に対し質量比で20%になるように蒸着した。成膜レートはそれぞれ1.2Å/s、0.3Å/sとした。この薄膜は、燐光発光層として機能する。
次に、この燐光発光層上に、化合物(H1)を抵抗加熱蒸着して膜厚10nmの薄膜を成膜した。成膜レートは1.2Å/sとした。この薄膜は障壁層として機能する。
次に、この障壁層上に、化合物(ET1)を抵抗加熱蒸着して膜厚10nmの薄膜を成膜した。成膜レートは1Å/sとした。この膜は電子注入層として機能する。
次に、この電子注入層上に膜厚1.0nmのLiFを成膜レート0.1Å/sで蒸着した。
次に、このLiF膜上に金属アルミニウムを成膜レート8.0Å/sにて蒸着し、膜厚80nmの金属陰極を形成して有機EL素子を得た。
(1)外部量子効率(%)
23℃、乾燥窒素ガス雰囲気下で、輝度1000cd/m2時の外部量子効率を輝度計(ミノルタ社製分光輝度放射計CS-1000)を用いて測定した。
(2)半減寿命(時間)
初期輝度1000cd/m2で連続通電試験(直流)を行い、初期輝度が半減するまでの時間を測定した。
(3)電圧(V)
23℃、乾燥窒素ガス雰囲気下で、KEITHLY 236 SOURCE MEASURE UNITを用いて、電気配線された素子に電圧を印加して発光させ、素子以外の配線抵抗にかかる電圧を差し引いて素子印加電圧を測定した。電圧の印加・測定と同時に輝度計(ミノルタ社製分光輝度放射計CS-1000)を用いて輝度測定も行い、これらの測定結果から素子輝度が100cd/m2時の電圧を読み取った。
実施例1において、化合物(1)を用いる代わりに表1に記載の化合物を用いて発光層を形成した以外は実施例1と同様にして有機EL素子を作製した。得られた有機EL素子を実施例1と同様に評価し、結果を表1に示す。
実施例1において、燐光発光層材料として、化合物(1)を用いる代わりに化合物(H1)を用い、正孔障壁層材料として、化合物(H1)の代わりに表2に記載の化合物を用いて正孔障壁層を形成した以外は実施例1と同様にして有機EL素子を作製した。
この明細書に記載の文献及び本願のパリ優先の基礎となる日本出願明細書の内容を全てここに援用する。
Claims (16)
- 下記式(1)で表される化合物。
X1~X3は、それぞれ独立して、O,又はSを表す。
Y1~Y4及びY21~Y24は、それぞれ独立して、C(Ra1),又はNを表す。
Y5~Y12のうち、Y5~Y8のうち一つと、Y9~Y12のうち一つは、互いに結合する炭素原子を表し、それ以外のY5~Y12は、それぞれ独立して、C(Ra1),又はNを表す。
Y13~Y16のうちA1に結合するものは、炭素原子を表し、それ以外のY13~Y16は、それぞれ独立して、C(Ra1),又はNを表す。
Y17~Y20のうちA1に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra1),又はNを表す。
A1は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリーレン基を表す。
nは、1~4の整数を表す。
Ar1~Ar4は、それぞれ独立して置換若しくは無置換の環形成炭素数6~30のアリール基,又は置換若しくは無置換の環形成原子数5~30のヘテロアリール基を表す。
Ra1は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、それぞれ独立して、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30のヘテロアリール基、置換若しくは無置換の炭素数1~30のアルキル基、又は置換若しくは無置換の炭素数1~30のフルオロアルキル基を表す。] - 下記式(2)で表される請求項1記載の化合物。
X1~X3は、それぞれ式(1)のX1~X3と同じである。
Y1~Y4、Y9、Y10、Y12、Y13、Y15、Y16及びY21~Y24は、それぞれ独立して、C(Ra2),又はNを表す。
Y5~Y8のうち一つは、単結合する炭素原子を表し、それ以外のY5~Y8は、それぞれ独立して、C(Ra2),又はNを表す。
Y17~Y20のうちA2に結合するものは、炭素原子を表し、それ以外のY17~Y20は、それぞれ独立して、C(Ra2),又はNを表す。
A2は、O,S,Si(Ar1)(Ar2),P(=O)(Ar3)(Ar4),置換若しくは無置換の環形成炭素数6~30のアリーレン基,又は置換若しくは無置換の環形成原子数5~30の、カルバゾリレン基を除くヘテロアリーレン基を表す。
n,Ar1~Ar4は、それぞれ式(1)のn,Ar1~Ar4と同じである。
Ra2は、水素原子、置換若しくは無置換の環形成炭素数6~30のアリール基、置換若しくは無置換の環形成原子数5~30の、カルバゾール基を除くヘテロアリール基,置換若しくは無置換の炭素数1~30のアルキル基,置換若しくは無置換の炭素数1~30のフルオロアルキル基,置換若しくは無置換の炭素数3~30のシクロアルキル基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のシリル基、シアノ基、置換若しくは無置換の炭素数1~30のアルコキシ基、置換若しくは無置換の環形成炭素数6~30のアリールオキシ基、置換若しくは無置換の炭素数7~30のアラルキル基、ヒドロキシ基、ニトロ基、置換若しくは無置換の炭素数1~30のアルキル基及び/又は無置換の環形成炭素数6~30のアリール基で置換された若しくは無置換のアミノ基、カルボキシ基、又はP(=O)(Rb)(Rc)を表す。
Rb及びRcは、それぞれ式(1)のRb,Rcと同じである。] - 前記A1又はA2が、置換若しくは無置換の環形成炭素数6~30のアリーレン基である請求項1~4のいずれかに記載の化合物。
- 前記A1又はA2が、置換若しくは無置換の環形成原子数5~20の、カルバゾリレン基を除くヘテロアリーレン基である請求項1~4のいずれかに記載の化合物。
- 請求項1~7のいずれかに記載の化合物を含む有機エレクトロルミネッセンス素子用材料。
- 陰極と陽極との間に、発光層を含む1以上の有機薄膜層を有し、前記有機薄膜層の少なくとも1層が、請求項8に記載の有機エレクトロルミネッセンス素子用材料を含有する有機エレクトロルミネッセンス素子。
- 前記発光層が、前記有機エレクトロルミネッセンス素子用材料を含有する請求項9に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、前記有機エレクトロルミネッセンス素子用材料を、発光層のホスト材料として含有する請求項10に記載の有機エレクトロルミネッセンス素子。
- 前記発光層と前記陰極との間に電子輸送帯域を有し、該電子輸送帯域が前記有機エレクトロルミネッセンス素子用材料を含有する請求項9~11のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光層が、燐光発光性材料を含有する請求項9~12のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記燐光発光性材料が、イリジウム(Ir),オスミウム(Os)及び白金(Pt)から選ばれる金属を含有する化合物である請求項13に記載の有機エレクトロルミネッセンス素子。
- 前記金属を含有する化合物が、オルトメタル化金属錯体である請求項14に記載の有機エレクトロルミネッセンス素子。
- 前記発光層と前記陰極との間に電子注入層を有し、前記電子注入層が含窒素複素環誘導体を含有する請求項9~15のいずれかに記載の有機エレクトロルミネッセンス素子。
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GB2548337A (en) * | 2016-03-08 | 2017-09-20 | Cambridge Display Tech Ltd | Compound, composition and organic light-emitting device |
KR102368409B1 (ko) | 2019-05-30 | 2022-02-25 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
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Also Published As
Publication number | Publication date |
---|---|
EP2757101A1 (en) | 2014-07-23 |
CN103649067A (zh) | 2014-03-19 |
TW201313695A (zh) | 2013-04-01 |
JPWO2013038650A1 (ja) | 2015-03-23 |
US20140175419A1 (en) | 2014-06-26 |
US9978952B2 (en) | 2018-05-22 |
KR20140060484A (ko) | 2014-05-20 |
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