JP2007073891A - 有機電界発光素子及び錯体化合物 - Google Patents
有機電界発光素子及び錯体化合物 Download PDFInfo
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- JP2007073891A JP2007073891A JP2005262305A JP2005262305A JP2007073891A JP 2007073891 A JP2007073891 A JP 2007073891A JP 2005262305 A JP2005262305 A JP 2005262305A JP 2005262305 A JP2005262305 A JP 2005262305A JP 2007073891 A JP2007073891 A JP 2007073891A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052697 platinum Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
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- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
- 229910001431 copper ion Inorganic materials 0.000 claims description 3
- 239000003446 ligand Substances 0.000 description 131
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- 239000000203 mixture Substances 0.000 description 17
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 125000004076 pyridyl group Chemical group 0.000 description 4
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- 229910000838 Al alloy Inorganic materials 0.000 description 3
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- 229910052693 Europium Inorganic materials 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 125000002252 acyl group Chemical group 0.000 description 3
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- 125000004450 alkenylene group Chemical group 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
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- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
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- 238000010884 ion-beam technique Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
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- 238000010030 laminating Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
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- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical class FN(F)F GVGCUCJTUSOZKP-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 description 1
- MBUJACWWYFPMDK-UHFFFAOYSA-N pentane-2,4-dione;platinum Chemical compound [Pt].CC(=O)CC(C)=O MBUJACWWYFPMDK-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
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- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoric acid amide group Chemical group P(N)(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- KGRJUMGAEQQVFK-UHFFFAOYSA-L platinum(2+);dibromide Chemical compound Br[Pt]Br KGRJUMGAEQQVFK-UHFFFAOYSA-L 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
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- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 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
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- 239000010453 quartz Substances 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
- 229920005604 random copolymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- ZOYIPGHJSALYPY-UHFFFAOYSA-K vanadium(iii) bromide Chemical compound [V+3].[Br-].[Br-].[Br-] ZOYIPGHJSALYPY-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- 239000010457 zeolite 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
- 239000011787 zinc oxide Substances 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
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Abstract
【解決手段】一対の電極間に発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、特定の一般式で表される化合物の少なくとも一種を有機層に含有することを特徴とする有機電界発光素子。
【選択図】なし
Description
ルシリルオキシ、トリフェニルシリルオキシなどが挙げられる。)、カルボニル配位子(例えばケトン配位子、エステル配位子、アミド配位子など)、エーテル配位子(例えばジアルキルエーテル配位子、ジアリールエーテル配位子、フリル配位子など)などが挙げられる。
合がさらに好ましい。L13は単結合、アルキレン基がより好ましく、アルキレン基がさらに好ましい。
バゾリル基であり、より好ましくはナフチル基、フェニル基、ピリジル基、キノリル基であり、特に好ましくはフェニル基である。
、アミノ基が好ましく、水素原子、アルキル基がより好ましく、水素原子がさらに好ましい。
本発明で使用する基板としては、有機層から発せられる光を散乱又は減衰させない基板であることが好ましい。その具体例としては、ジルコニア安定化イットリウム(YSZ)、ガラス等の無機材料、ポリエチレンテレフタレート、ポリブチレンフタレート、ポリエチレンナフタレート等のポリエステル、ポリスチレン、ポリカーボネート、ポリエーテルスルホン、ポリアリレート、ポリイミド、ポリシクロオレフィン、ノルボルネン樹脂、ポリ(クロロトリフルオロエチレン)等の有機材料が挙げられる。
例えば、基板としてガラスを用いる場合、その材質については、ガラスからの溶出イオンを少なくするため、無アルカリガラスを用いることが好ましい。また、ソーダライムガラスを用いる場合には、シリカなどのバリアコートを施したものを使用することが好ましい。有機材料の場合には、耐熱性、寸法安定性、耐溶剤性、電気絶縁性、及び加工性に優れていることが好ましい。
透湿防止層(ガスバリア層)の材料としては、窒化珪素、酸化珪素などの無機物が好適に用いられる。透湿防止層(ガスバリア層)は、例えば、高周波スパッタリング法などにより形成することができる。熱可塑性基板を用いる場合には、更に必要に応じて、ハードコート層、アンダーコート層などを設けてもよい。
陽極は、通常、有機層に正孔を供給する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。前述のごとく、陽極は、通常透明陽極とし
て設けられる。
陰極は、通常、有機層に電子を注入する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。
、K、Cs等)、アルカリ土類金属(たとえばMg、Ca等)、金、銀、鉛、アルミニウム、ナトリウム−カリウム合金、リチウム−アルミニウム合金、マグネシウム−銀合金、インジウム、イッテルビウム等の希土類金属、などが挙げられる。これらは、1種単独で使用してもよいが、安定性と電子注入性とを両立させる観点からは、2種以上を好適に併用することができる。
アルミニウムを主体とする材料とは、アルミニウム単独、アルミニウムと0.01〜10質量%のアルカリ金属又はアルカリ土類金属との合金若しくはこれらの混合物(例えば、リチウム−アルミニウム合金、マグネシウム−アルミニウム合金など)をいう。
また、陰極と前記有機層との間に、アルカリ金属又はアルカリ土類金属のフッ化物、酸化物等による誘電体層を0.1〜5nmの厚みで挿入してもよい。この誘電体層は、一種の電子注入層と見ることもできる。誘電体層は、例えば、真空蒸着法、スパッタリング法、イオンプレーティング法等により形成することができる。
また、陰極は、透明であってもよいし、不透明であってもよい。なお、透明な陰極は、陰極の材料を1〜10nmの厚さに薄く成膜し、更にITOやIZO等の透明な導電性材料を積層することにより形成することができる。
本発明における有機層について説明する。本発明の素子は、発光層を含む少なくとも一層の有機層を有しており、有機発光層以外の他の有機層としては、前述したごとく、正孔輸送層、電子輸送層、正孔ブロック層、電子ブロック層、正孔注入層、電子注入層等の各層が挙げられる。
本発明の有機電界発光素子において、有機層を構成する各層は、蒸着法やスパッタ法等
の乾式製膜法、転写法、印刷法等いずれによっても好適に形成することができる。
発光層は、電界印加時に、陽極、正孔注入層、又は正孔輸送層から正孔を受け取り、陰極、電子注入層、又は電子輸送層から電子を受け取り、正孔と電子の再結合の場を提供して発光させる機能を有する層である。
本発明における発光層は、発光材料のみで構成されていても良く、ホスト材料と発光材料の混合層とした構成でも良い。発光材料は蛍光発光材料でも燐光発光材料であっても良く、ドーパントは一種であっても二種以上であっても良い。ホスト材料は電荷輸送材料であることが好ましい。ホスト材料は一種であっても二種以上であっても良く、例えば、電子輸送性のホスト材料とホール輸送性のホスト材料を混合した構成が挙げられる。さらに、発光層中に電荷輸送性を有さず、発光しない材料を含んでいても良い。発光層としては、発光材料として本発明の錯体を用いたものが好ましく、少なくとも一種のホスト材料と本発明の錯体により構成されていることがより好ましい。
また、発光層は一層であっても二層以上であってもよく、それぞれの層が異なる発光色で発光してもよい。
遷移金属原子としては、特に限定されないが、好ましくは、ルテニウム、ロジウム、パラジウム、タングステン、レニウム、オスミウム、イリジウム、及び白金が挙げられ、より好ましくは、レニウム、イリジウム、及び白金である。
ランタノイド原子としては、ランタン、セリウム、プラセオジム、ネオジム、サマリウム、ユーロピウム、ガドリニウム、テルビウム、ジスプロシウム、ホルミウム、エルビウム、ツリウム、イッテルビウム、ルテシウムが挙げられる。これらのランタノイド原子の中でも、ネオジム、ユーロピウム、及びガドリニウムが好ましい。
具体的な配位子としては、好ましくは、ハロゲン配位子(好ましくは塩素配位子)、含窒素ヘテロ環配位子(例えば、フェニルピリジン、ベンゾキノリン、キノリノール、ビピリジル、フェナントロリンなど)、ジケトン配位子(例えば、アセチルアセトンなど)、カルボン酸配位子(例えば、酢酸配位子など)、一酸化炭素配位子、イソニトリル配位子、シアノ配位子であり、より好ましくは、含窒素ヘテロ環配位子である。上記錯体は、化合物中に遷移金属原子を一つ有してもよいし、また、2つ以上有するいわゆる複核錯体であってもよい。異種の金属原子を同時に含有していてもよい。
正孔注入層、正孔輸送層は、陽極又は陽極側から正孔を受け取り陰極側に輸送する機能を有する層である。正孔注入層、正孔輸送層は、具体的には、カルバゾール誘導体、トリアゾール誘導体、オキサゾール誘導体、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、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、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、芳香族第三級アミン化合物、スチリルアミン化合物、芳香族ジメチリディン系化合物、ポルフィリン系化合物、有機シラン誘導体、カーボン等を含有する層であることが好ましい。
正孔輸送層の厚さとしては、1nm〜500nmであるのが好ましく、5nm〜200nmであるのがより好ましく、10nm〜100nmであるのが更に好ましい。また、正孔注入層の厚さとしては、0.1nm〜200nmであるのが好ましく、0.5nm〜100nmであるのがより好ましく、1nm〜100nmであるのが更に好ましい。
正孔注入層、正孔輸送層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
電子注入層、電子輸送層は、陰極又は陰極側から電子を受け取り陽極側に輸送する機能を有する層である。電子注入層、電子輸送層は、具体的には、トリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、フルオレノン誘導体、アントラキノジメタン誘導体、アントロン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、カルボジイミド誘導体、フルオレニリデンメタン誘導体、ジスチリルピラジン誘導体、ナフタレン、ペリレン等の芳香環テトラカルボン酸無水物、フタロシアニン誘導体、8−キノリノール誘導体の錯体やメタルフタロシアニン、ベンゾオキサゾールやベンゾチアゾールを配位子とする錯体に代表される各種錯体、有機シラン誘導体、等を含有する層であることが好ましい。
電子輸送層の厚さとしては、1nm〜500nmであるのが好ましく、5nm〜200nmであるのがより好ましく、10nm〜100nmであるのが更に好ましい。また、電子注入層の厚さとしては、0.1nm〜200nmであるのが好ましく、0.2nm〜1
00nmであるのがより好ましく、0.5nm〜50nmであるのが更に好ましい。
電子注入層、電子輸送層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
正孔ブロック層は、陽極側から発光層に輸送された正孔が、陰極側に通りぬけることを防止する機能を有する層である。本発明において、発光層と陰極側で隣接する有機層として、正孔ブロック層を設けることができる。
正孔ブロック層を構成する有機化合物の例としては、BAlq等のアルミニウム錯体、トリアゾール誘導体、BCP等のフェナントロリン誘導体、等が挙げられる。
正孔ブロック層の厚さとしては、1nm〜500nmであるのが好ましく、5nm〜200nmであるのがより好ましく、10nm〜100nmであるのが更に好ましい。
正孔ブロック層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
本発明において、有機EL素子全体は、保護層によって保護されていてもよい。
保護層に含まれる材料としては、水分や酸素等の素子劣化を促進するものが素子内に入ることを抑止する機能を有しているものであればよい。
その具体例としては、In、Sn、Pb、Au、Cu、Ag、Al、Ti、Ni等の金属、MgO、SiO、SiO2、Al2O3、GeO、NiO、CaO、BaO、Fe2O3、Y2O3、TiO2等の金属酸化物、SiNx、SiNxOy等の金属窒化物、MgF2、LiF、AlF3、CaF2等の金属フッ化物、ポリエチレン、ポリプロピレン、ポリメチルメタクリレート、ポリイミド、ポリウレア、ポリテトラフルオロエチレン、ポリクロロトリフルオロエチレン、ポリジクロロジフルオロエチレン、クロロトリフルオロエチレンとジクロロジフルオロエチレンとの共重合体、テトラフルオロエチレンと少なくとも1種のコモノマーとを含むモノマー混合物を共重合させて得られる共重合体、共重合主鎖に環状構造を有する含フッ素共重合体、吸水率1%以上の吸水性物質、吸水率0.1%以下の防湿性物質等が挙げられる。
本発明の素子は、封止容器を用いて素子全体を封止してもよい。封止容器と素子の間の空間に水分吸収剤又は不活性液体を封入してもよい。水分吸収剤としては、特に限定されることはないが、例えば、酸化バリウム、酸化ナトリウム、酸化カリウム、酸化カルシウム、硫酸ナトリウム、硫酸カルシウム、硫酸マグネシウム、五酸化燐、塩化カルシウム、塩化マグネシウム、塩化銅、フッ化セシウム、フッ化ニオブ、臭化カルシウム、臭化バナジウム、モレキュラーシーブ、ゼオライト、酸化マグネシウム等を挙げることができる。不活性液体としては、特に限定されることはないが、例えば、パラフィン類、流動パラフィン類、パーフルオロアルカンやパーフルオロアミン、パーフルオロエーテル等のフッ素系溶剤、塩素系溶剤、シリコーンオイル類が挙げられる。
例示化合物1は下記スキームに従って合成した。
窒素気流下、化合物A(5.0g)、酢酸パラジウム(73mg)、ナトリウム−tert−ブトキシド(11.5g)、キシレン(20mL)の混合物に、トリ−tert−ブチルホスフィン(0.3ml)、ブロモベンゼン(9.4ml)を加えて、150℃で3時間加熱した。室温まで冷却後、水を加えて、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=20:1)で精製することにより化合物Bを3.13g(収率32%)得た。
窒素気流下、ドライアイスで冷却したテトラヒドロフラン(5ml)にn−ブチルリチウムの10Mヘキサン溶液(0.36ml)、アセトニトリル(0.21ml)を順次加え、10分間攪拌後、化合物B(0.31g)のテトラヒドロフラン溶液(4ml)を加えて、室温まで昇温した。飽和塩化アンモニウム水溶液を加えて、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=4:1)で精製することにより化合物Cを0.28g(収率87%)得た。
化合物B(0.43g)、化合物C(0.33g)、水酸化カリウム(0.27g)をメチルスルホキシド(4ml)に溶かして、100℃で20分間加熱した。室温まで冷却後、希塩酸を加え、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=10:1〜5:1)で精製することにより化合物Dを0.33g(収率55%)得た。
化合物D(0.33g)を濃塩酸(4ml)、イソプロピルアルコール(4ml)に溶かして、5時間過熱還流した。冷却後、炭酸水素ナトリウム水溶液で中和し、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=9:1〜4:1)で精製することにより化合物Eを0.23g(収率40%)得た。
化合物E(0.20g)をテトラヒドロフラン(5ml)に溶かして、氷浴で冷却しながらリチウムジイソプロピルアミドの1.8Mテトラヒドロフラン−エチルベンゼン−ヘプタン溶液(0.3ml)を加え、引き続きヨウ化メチルの0.35Mテトラヒドロフラン溶液(1ml)を加えた。この操作を再度繰り返し、水を加えて、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(酢酸エチル)で精製することにより化合物Fを0.17g(収率81%)得た。
窒素雰囲気下、化合物F(0.17g)、2、4−ジフルオロフェニルホウ酸(0.18g)、酢酸パラジウム(6.3mg)、トリフェニルホスフィン(29mg)、キシレン(5ml)の混合物に炭酸カリウム(0.31g)水溶液(1ml)を加えて、150℃で4時間攪拌した。室温まで冷却後、酢酸エチルで抽出し、有機層を硫酸マグネシウムで乾燥し、酢酸エチルを留去した。得られた粗体をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=9:1)で精製することにより化合物Gを84mg(収率40%)得た。
窒素気流下、化合物G(84mg)、塩化白金(35mg)、ベンゾニトリル(10ml)の混合物を、160℃で4時間攪拌した。ベンゾニトリルを留去し、得られた粗体をシリカゲルカラムクロマトグラフィー(塩化メチレン)で精製することにより例示化合物1を62mg(収率60%)得た。
1.有機電界発光素子の作製
(1)本発明の有機電界発光素子(TC−21)の作製
0.5mm厚み、2.5cm角のITO膜を有するガラス基板(ジオマテック社製、表面抵抗10Ω/□)を洗浄容器に入れ、2−プロパノール中で超音波洗浄した後、30分間UV−オゾン処理を行った。この透明陽極(ITO膜)上に真空蒸着法にて以下の有機化合物層を順次蒸着した。
本発明の実施例における蒸着速度は、特に断りのない場合は0.1〜2nm/秒である。蒸着速度は水晶振動子を用いて測定した。以下に記載の膜厚も水晶振動子を用いて測定したものである。
銅フタロシアニン(CuPc):膜厚10nm
(ホール輸送層)
NPD:膜厚40nm
(発光層)
MCP=92質量%、例示化合物1=8質量%の混合層:膜厚30nm
(電子輸送層)
Balq:膜厚10nm
(電子注入層)
Alq:膜厚10nm
発光材料を、例示化合物1から国際公開第04/108857号パンフレットに記載の下記比較化合物1に変更する以外は、TC−21と同様の方法で有機電界発光素子(TC−22)を作製した。
上記で得られた有機電界発光素子(TC−21及び22)に、直流定電圧(5V)を印加したところ、共に、リン光発光材料に由来する青緑色に発光した。
TC−21はTC−22に比べて、最高輝度が1.5倍、駆動寿命が1.5倍であった。
Claims (8)
- 一対の電極間に発光層を含む少なくとも一層の有機層を有する有機電界発光素子であって、下記一般式(I)で表される化合物の少なくとも一種を有機層に含有することを特徴とする有機電界発光素子。
(一般式(I)中、Mは金属イオン、Q11、Q12、Q13及びQ14は、各々独立に、Mに配位する原子群、L10、L11、L12及びL13は、各々独立に、単結合または連結基を表し、Q11、Q12、Q13及びQ14とMを結ぶ実線は、共有結合、イオン結合、配位結合のいずれかを表す。n10は0もしくは1で、n=0の場合はQ13とQ14の間に結合は存在しない。m11、m12、m13及びm14は、各々独立に、0以上の整数で、少なくともひとつは1以上である。Ar11、Ar12、Ar13及びAr14は、各々独立に、アリール基またはヘテロアリール基を表し、R11、R12、R13及びR14は、各々独立に、水素原子または置換基を表す。) - 一般式(I)中の金属イオンMが、白金イオン、イリジウムイオン、レニウムイオン、パラジウムイオン、ロジウムイオン、ルテニウムイオン、および銅イオンの群から選ばれたイオンであることを特徴とする、請求項1に記載の有機電界発光素子。
- 一般式(I)中の金属イオンMが、白金イオン、イリジウムイオン、パラジウムイオン、およびロジウムイオンの群から選ばれたイオンであることを特徴とする、請求項1又は2に記載の有機電界発光素子。
- 一般式(I)における置換基がアルキル基、アリール基またはヘテロアリール基であることを特徴とする、請求項1〜3のいずれかに記載の有機電界発光素子。
- 一般式(I)で表される化合物が、下記一般式(II)で表される化合物であることを特徴とする、請求項1〜4のいずれかに記載の有機電界発光素子。
(一般式(II)中、Q21、Q22、Q23及びQ24は、各々独立に、白金イオンに配位する原子群、L20、L21及びL22は、各々独立に、単結合または連結基を表し、Q21、Q22、Q23及びQ24と白金イオンを結ぶ実線は共有結合、イオン結合、配位結合のいずれかを表している。m21、m22は、各々独立に、0以上の整数で、少なくともひとつは1以上である。Ar及びAr22は、各々独立に、アリール基またはヘテロアリール基、R21及びR22は、各々独立に、水素原子または置換基を表す。) - 一般式(II)における置換基がアルキル基、アリール基またはヘテロアリール基であることを特徴とする、請求項5に記載の有機電界発光素子。
- 一般式(I)で表される化合物が、下記一般式(III)で表される化合物であることを特徴とする、請求項1〜6のいずれかに記載の有機電界発光素子。
(一般式(III)中、白金イオンと窒素原子を結ぶ実線は配位結合を表し、白金イオンと炭素原子を結ぶ実線は共有結合あるいはイオン結合を表す。R301及びR302は、各々独立に、水素原子または置換基を表す。Ar31及びAr32は、各々独立に、アリール基または
ヘテロアリール基を表し、R31及びR32は、各々独立に、水素原子または置換基を表す。R331、R332、R341及びR342は、各々独立に、水素原子または置換基を表す。R35及びR36は、各々独立に、置換基を表し、n35及びn36は、各々独立に、0〜4の整数を表す。) - 請求項7に記載の一般式(III)で表されることを特徴とする化合物。
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DE102013200942B4 (de) | 2012-01-23 | 2023-07-27 | Udc Ireland Ltd. | Organisches Elektrolumineszenz-Element, Ladungstransportmaterial für organisches Elektrolumineszenz-Element, und Licht-emittierende Vorrichtung, Anzeigevorrichtung und Beleuchtungsvorrichtung, die jeweils das Element umfassen |
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KR20200014451A (ko) * | 2018-07-31 | 2020-02-11 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
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