JP6835326B2 - ヘテロレプティックイリジウム錯体、ならびに該化合物を用いた発光材料および有機発光素子 - Google Patents
ヘテロレプティックイリジウム錯体、ならびに該化合物を用いた発光材料および有機発光素子 Download PDFInfo
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- JP6835326B2 JP6835326B2 JP2016176106A JP2016176106A JP6835326B2 JP 6835326 B2 JP6835326 B2 JP 6835326B2 JP 2016176106 A JP2016176106 A JP 2016176106A JP 2016176106 A JP2016176106 A JP 2016176106A JP 6835326 B2 JP6835326 B2 JP 6835326B2
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- iridium complex
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- carbon atoms
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- 229910052741 iridium Inorganic materials 0.000 title claims description 97
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims description 96
- 239000000463 material Substances 0.000 title claims description 64
- 150000001875 compounds Chemical class 0.000 title description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- -1 R 14 to R 19 Chemical compound 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 230000001815 facial effect Effects 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000010410 layer Substances 0.000 description 118
- 238000000859 sublimation Methods 0.000 description 57
- 230000008022 sublimation Effects 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 30
- 238000006862 quantum yield reaction Methods 0.000 description 29
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- 239000003446 ligand Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 22
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 229910052786 argon Inorganic materials 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 150000002503 iridium Chemical class 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000295 emission spectrum Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 0 CCCC(C(C1)C11C(C)(C)CC)C1C1(*CCC1)C=C Chemical compound CCCC(C(C1)C11C(C)(C)CC)C1C1(*CCC1)C=C 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000007699 photoisomerization reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000123 polythiophene Chemical class 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000011000 absolute method Methods 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001846 chrysenes Chemical class 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- 230000001747 exhibiting effect Effects 0.000 description 2
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- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- 238000001953 recrystallisation Methods 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
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- APRMCBSTMFKLEI-UHFFFAOYSA-N 2-chloro-5-methylpyrimidine Chemical compound CC1=CN=C(Cl)N=C1 APRMCBSTMFKLEI-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- MEAAWTRWNWSLPF-UHFFFAOYSA-N 2-phenoxypyridine Chemical compound C=1C=CC=NC=1OC1=CC=CC=C1 MEAAWTRWNWSLPF-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical class C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical class C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
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Images
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Description
(1)陽極/発光層/陰極
(2)陽極/発光層/電子輸送層/陰極
(3)陽極/正孔輸送層/発光層/陰極
(4)陽極/正孔輸送層/発光層/電子輸送層/陰極
(5)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(6)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(7)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
発光層は、電極から注入された電子および正孔が再結合し、励起子を経由して発光する層であり、発光する部分は発光層の層内であっても、発光層と隣接層との界面であってもよい。
電子輸送層とは、電子を輸送する機能を有する材料からなり、陰極より注入された電子を発光層に伝達する機能を有していればよい。
正孔阻止層とは広い意味では電子輸送層の機能を有する層であり、好ましくは電子を輸送する機能を有しつつ正孔を輸送する能力が小さい材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔との再結合確率を向上させることができる。
電子注入層(「陰極バッファー層」ともいう。)とは、駆動電圧低下または発光輝度向上のために陰極と発光層との間に設けられる層のことである。
正孔輸送層とは、正孔を輸送する機能を有する材料からなり、陽極より注入された正孔を発光層に伝達する機能を有していればよい。
電子阻止層とは広い意味では正孔輸送層の機能を有する層であり、好ましくは正孔を輸送する機能を有しつつ電子を輸送する能力が小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔との再結合確率を向上させることができる。
本発明では、正孔注入層(「陽極バッファー層」ともいう)とは、駆動電圧低下または発光輝度向上のために陽極と発光層との間に設けられる層のことである。
本発明化合物(K−2)の合成
1H−NMR(400MHz/CDCl3)δ:8.66−8.68(m,3H),8.39(d,1H),7.70−7.72(m,3H),7.56(t,1H),7.46(t,2H),7.37(t,1H),2.36(s,3H).
1H−NMR(400MHz/DMSO−d6)δ:8.75(t,2H),8.44(s,2H),8.27(d,1H),8.21(d,1H),8.14(d,1H),8.07(d,1H),7.96(d,1H),7.74(d,1H),7.64−7.66(m,3H),7.57(d,2H),7.34−7.46(m,5H),7.22−7.30(m,3H),7.17(dd,1H),7.07(dd,1H),6.95(t,1H),6.76(t,1H),6.61(d,1H),6.50(dd,2H),2.24(s,3H),2.06(s,3H).
本発明化合物(K−4)の合成
1H−NMR(400MHz/DMSO−d6)δ:8.69(d,1H),8.52(q,2H),8.41(q,2H),8.10(d,1H),8.03(d,1H),8.01(d,1H),7.89−7.95(m,3H),7.72(d,1H),7.59(d,1H),7.54(d,2H),7.39(t,1H),7.34(t,2H),7.29(t,1H),7.22(t,1H),7.15(t,1H),7.06(dd,1H),6.94(t,1H),6.87(t,1H),6.62−6.72(m,3H),6.38−6.46(m,3H),2.10(s,3H).
本発明化合物(K−14)と(K−16)との合成
1H−NMR(400MHz/DMSO−d6)δ:8.94−8.96(m,1H),8.74(dd,2H),8.21−8.26(m,3H),7.96−8.02(m,2H),7.77−7.83(m,2H),7.69(d,1H),7.58−7.65(m,6H),7.36−7.43(m,4H),7.23−7.29(m,2H),7.18(dd,1H),7.12(dd,1H),6.98(t,1H),6.78−6.86(m,2H),6.73(d,2H),2.23(s,3H),2.06(s,3H).
1H−NMR(400MHz/DMSO−d6)δ:8.93(t,2H),8.73(d,1H),8.17−8.27(m,3H),8.00−8.02(m,1H),7.92−7.95(m,1H),7.76−7.83(m,4H),7.67(d,1H),7.59−7.61(m,4H),7.48(d,1H),7.36−7.40(m,3H),7.25(t,1H),7.11(dd,1H),6.90−6.99(m,2H),6.72−6.87(m,4H),6.68(d,1H),2.07(s,3H).
本発明化合物(K−4)のクロロホルム中での発光特性
本発明化合物(K−4)をクロロホルムに溶解させ、アルゴンガスを通気した後、浜松ホトニクス株式会社製の絶対PL量子収率測定装置(C9920)を用いて、室温での発光スペクトル(励起波長:350nm)を測定したところ、赤色発光(発光極大波長:622nm)を示した。発光量子収率は0.65であった。
本発明化合物(K−14)のクロロホルム中での発光特性
本発明化合物(K−14)をクロロホルムに溶解させ、アルゴンガスを通気した後、浜松ホトニクス株式会社製の絶対PL量子収率測定装置装置(C9920)を用いて、室温での発光スペクトル(励起波長:340nm)を測定したところ、赤色発光(発光極大波長:628nm)を示した。発光量子収率は0.55であった。
本発明化合物(K−16)のクロロホルム中での発光特性
本発明化合物(K−16)をクロロホルムに溶解させ、アルゴンガスを通気した後、浜松ホトニクス株式会社製の絶対PL量子収率測定装置装置(C9920)を用いて、室温での発光スペクトル(励起波長:340nm)を測定したところ、赤色発光(発光極大波長:631nm)を示した。発光量子収率は0.61であった。
比較化合物(1)のTHF中の発光特性
比較化合物(1)をTHFに溶解させ、アルゴンガスを通気した後、浜松ホトニクス株式会社製の絶対PL量子収率測定装置(C9920)を用いて、室温での発光スペクトル(励起波長:350nm)を測定したところ、緑色発光(発光極大波長:527nm)を示した。発光量子収率は0.64であった。
本発明化合物(K−4)の昇華精製
本発明化合物(K−4)153mgを昇華精製装置(P−200、エイエルエス・テクノロジー社製)に入れ、真空度1×10−4Pa、温度310〜340℃の条件下で、9時間かけて昇華精製したところ、昇華精製による収率は95%であり、昇華残渣は全くなかった。なお、昇華精製後の本発明化合物(K−4)をHPLCで分析したところ、昇華精製よる純度低下は生じなかった。本発明化合物(K−4)の熱的安定性および昇華性は良好であることが明らかになった。
本発明化合物(K−16)の昇華精製
本発明化合物(K−16)93.5mgを昇華精製装置(P−200、エイエルエス・テクノロジー社製)に入れ、真空度1×10−4Pa、温度300〜320℃の条件下で、9時間かけて昇華精製したところ、昇華精製による収率は96%であり、昇華残渣は全くなかった。なお、昇華精製後の本発明化合物(K−16)をHPLCで分析したところ、昇華精製による純度低下がわずかに生じていたが、純度99.7%から純度99.3%への低下にとどまった。本発明化合物(K−16)の熱的安定性および昇華性は良好であることが明らかになった。
比較化合物(1)の昇華精製
比較化合物(1)107mgを昇華精製装置(P−200、エイエルエス・テクノロジー社製)に入れ、真空度1×10−4Pa、温度300〜335℃の条件下で、18時間かけて昇華精製したところ、昇華残渣が多く残った(投入量の10.2%)。なお、昇華精製後の比較化合物(1)をHPLCで分析したところ、昇華精製よる純度低下は生じなかった。一方、昇華残渣(投入量の10.2%)をHPLCで分析したところ、純度は93.1%であり、昇華精製前の純度99.8%から大きく低下していた。比較化合物(1)は、本発明化合物よりも昇華速度が非常に遅く、本発明化合物と同条件下で昇華精製すると分解反応が進行することがわかった。
本発明化合物(K−4)のCBPとの共蒸着膜中の発光特性
本発明化合物(K−4)と公知ホスト材料であるCBP(E−3)とを、真空度1×10−4Paで、石英基板上に5:95(質量濃度比)で共蒸着(30nm)し、浜松ホトニクス株式会社製の絶対PL量子収率測定装置(C9920)を用いて、室温での発光スペクトル(励起波長:340nm)を測定したところ、赤色発光(発光極大波長:600nm)を示した。発光量子収率は0.88であった。
本発明化合物(K−16)のCBPとの共蒸着膜中の発光特性
本発明化合物(K−16)と公知ホスト材料であるCBP(E−3)とを、真空度1×10−4Paで、石英基板上に5:95(質量濃度比)で共蒸着(30nm)し、浜松ホトニクス株式会社製の絶対PL量子収率測定装置(C9920)を用いて、室温での発光スペクトル(励起波長:340nm)を測定したところ、赤色発光(発光極大波長:619nm)を示した。発光量子収率は0.68であった。
比較化合物(1)のCBPとの共蒸着膜中の発光特性
比較化合物(1)と公知ホスト材料であるCBP(E−3)とを、真空度1×10−4Paで、石英基板上に5:95(質量濃度比)で共蒸着(30nm)し、浜松ホトニクス株式会社製の絶対PL量子収率測定装置(C9920)を用いて、室温での発光スペクトル(励起波長:340nm)を測定したところ、緑色発光(発光極大波長:526nm)を示した。発光量子収率は0.82であった。
本発明化合物(K−4)を用いて作製した有機電界発光素子の特性評価
陽極として、酸化錫インジウム(ITO)を100nmの膜厚で線幅2mmの櫛形にパターニングして成膜された無アルカリガラス基板(厚木ミクロ社製)を透明導電性支持基板として用いた。これを超純水、アセトン、イソプロピルアルコール(IPA)で順次超音波洗浄し、次いでIPAで煮沸洗浄後乾燥した。次いで、UV/オゾン洗浄したものを透明導電性支持基板として使用した。
正孔輸送層(40nm):化合物(E−2)
発光層(20nm):本発明化合物(K−4)(質量濃度15%)と化合物(E−3)(質量濃度85%)とを共蒸着
正孔阻止層(10nm):化合物(E−4)
電子輸送層(30nm):化合物(E−5)
電子注入層(0.5nm):化合物(E−6)
金属電極層(100nm):Al
本発明化合物(K−16)を用いて作製した有機電界発光素子の特性評価
実施例V−1で用いた本発明化合物(K−4)の代わりに本発明化合物(K−16)を用いた以外は、同様に有機電界発光素子を作製し、特性評価を行った。発光ピーク波長が621nmの赤色発光が得られ、最高輝度は25800cd/m2、100cd/m2の時の外部量子効率は11.3%と非常に良好な発光特性が得られた。本発明化合物(K−16)を用いて作製した有機電界発光素子のELスペクトルを図1に示す。
Claims (9)
- R 14 〜R 19 が水素原子または炭素数1〜30のアルキル基であることを特徴とする請求項1に記載のイリジウム錯体。
- R 14 〜R 19 の少なくとも1つがハロゲン原子であることを特徴とする請求項1または2に記載のイリジウム錯体。
- R4、R5、R9、R10がいずれも水素原子であることを特徴とする請求項1〜3のいずれか一つに記載のイリジウム錯体。
- mは2であり、nは1であることを特徴とする請求項1〜4のいずれか一つに記載のイリジウム錯体。
- mは1であり、nは2であることを特徴とする請求項1〜4のいずれか一つに記載のイリジウム錯体。
- フェイシャル体であることを特徴とする請求項1〜6のいずれか一つに記載のイリジウム錯体。
- 請求項1〜7のいずれか一つに記載のイリジウム錯体を含むことを特徴とする発光材料。
- 請求項8に記載の発光材料を含むことを特徴とする有機発光素子。
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