JP5819577B2 - 発光素子 - Google Patents
発光素子 Download PDFInfo
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- JP5819577B2 JP5819577B2 JP2008302138A JP2008302138A JP5819577B2 JP 5819577 B2 JP5819577 B2 JP 5819577B2 JP 2008302138 A JP2008302138 A JP 2008302138A JP 2008302138 A JP2008302138 A JP 2008302138A JP 5819577 B2 JP5819577 B2 JP 5819577B2
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- organometallic complex
- emitting element
- organic compound
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- 125000002524 organometallic group Chemical group 0.000 claims description 162
- 150000002894 organic compounds Chemical class 0.000 claims description 117
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 53
- 229910052751 metal Inorganic materials 0.000 claims description 53
- 239000002184 metal Substances 0.000 claims description 53
- 239000003446 ligand Substances 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 25
- -1 aromatic amine compound Chemical class 0.000 claims description 22
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- 229910052741 iridium Inorganic materials 0.000 claims description 17
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 239000013522 chelant Substances 0.000 claims description 8
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000002390 heteroarenes Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 181
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical class C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 85
- 239000000463 material Substances 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 38
- 150000002431 hydrogen Chemical class 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000000758 substrate Substances 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 19
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 16
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 125000004423 acyloxy group Chemical group 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000010893 electron trap Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000005284 excitation Effects 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 238000005381 potential energy Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 150000003252 quinoxalines Chemical class 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005595 acetylacetonate group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 3
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229910052691 Erbium Inorganic materials 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 0 *c1c*(Cc2c3c(c4ccccc44)ccc2)c3c4*1 Chemical compound *c1c*(Cc2c3c(c4ccccc44)ccc2)c3c4*1 0.000 description 2
- GGTXYOVKMNRYMW-UHFFFAOYSA-N 3-phenylphenanthro[9,10-b]pyrazine Chemical class C1=CC=CC=C1C1=CN=C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)C3=N1 GGTXYOVKMNRYMW-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
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- 229910052804 chromium Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000005274 electronic transitions Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007122 ortho-metalation reaction Methods 0.000 description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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Description
まず、本実施形態1では、本発明の発光素子の概念について説明する。なお、本明細書中においてHOMO準位又はLUMO準位が深いとは、そのエネルギーレベルが小さいことを意味し、HOMO準位又はLUMO準位が浅いとは、そのエネルギーレベルが大きいことを意味する。例えば、−2.54eVのLUMO準位を有する物質Aは、−2.28eVのLUMO準位を有する物質BよりLUMO準位が0.26eV深く、−2.85eVのLUMO準位を有する物質CよりLUMO準位が0.31eV浅いと言うことができる。
本実施形態2では、本発明の発光素子の構成について、具体的な材料を列挙しながら説明する。素子構成を図3に示す。
本実施の形態では、本発明の発光素子に用いることができるジベンゾ[f,h]キノキサリン系有機金属錯体について、具体的に例示する。
一般式G1または一般式G5で表されるジベンゾ[f,h]キノキサリン系有機金属錯体は、下記一般式(G0)で表されるジベンゾ[f,h]キノキサリン誘導体が、第9族または第10族の金属イオンに対してオルトメタル化することによりなっている。
次に、一般式(G0)で表されるジベンゾ[f,h]キノキサリン誘導体をオルトメタル化して形成される有機金属錯体、すなわち下記一般式(G1)で表される構造を有する有機金属錯体について説明をする。
ここで、上述した一般式(G1)で表される構造を有する有機金属錯体の中でも、好ましい具体例である下記一般式(G5)で表される有機金属錯体について説明する。
本実施形態4では、本発明の発光素子を有する発光装置の一例として、画像表示装置について説明する。
本発明の発光素子は発光効率が高く寿命が長いため、発光装置の一例である照明装置に用いることができる。そこで本実施形態5では、本発明の発光素子を有する照明装置の応用例を説明する。
実施形態4で示したような本発明の画像表示装置は、良好な画像を表示することができるため、本発明の画像表示装置を電子機器の表示部に適用することによって、優れた映像を提供できる電子機器を得ることができる。また、本発明の発光素子を含む画像表示装置や照明装置(すなわち発光装置)は消費電力が低く寿命が長い。したがって、本発明の発光装置を電子機器の表示部に適用することによって、消費電力の少ない電子機器を得ることができ、例えば、待受時間等の長い電話機等を得ることができる。以下に、本発明の発光素子を適用した発光装置を実装した電子機器の一実施例を示す。
まず、本実施例で用いる参照電極(Ag/Ag+電極)の真空準位に対するポテンシャルエネルギー(eV)を算出した。つまり、Ag/Ag+電極のフェルミ準位を算出した。メタノール中におけるフェロセンの酸化還元電位は、標準水素電極に対して+0.610[V vs. SHE]であることが知られている(参考文献;Christian R.Goldsmith et al., J.Am.Chem.Soc., Vol.124, No.1,83−96, 2002)。一方、本実施例で用いる参照電極を用いて、メタノール中におけるフェロセンの酸化還元電位を求めたところ、+0.11V[vs.Ag/Ag+]であった。したがって、本実施例1で用いる参照電極のポテンシャルエネルギーは、標準水素電極に対して0.50[eV]低くなっていることがわかった。
まず、本測定例で、構造式(1)で表されるIr(dbq−P)2(acac)を例に、CV測定からのLUMO準位の算出について詳述する。還元反応特性のCV測定結果を図16に示す。なお、還元反応特性の測定は、参照電極に対する作用電極の電位を−1.35Vから−2.30Vまで走査した後、−2.30Vから−1.35Vまで走査した。
同様の手法にて、実施形態3で開示したジベンゾ[f,h]キノキサリン系有機金属錯体のLUMO準位を測定した。また参考として、赤色の燐光性化合物のホスト材料として広範に用いられている電子輸送性の化合物BAlq(下記構造式(i))に関し、そのLUMO準位も評価した。
まず、陽極として110nmの膜厚でインジウム錫珪素酸化物(ITSO)が成膜されたガラス基板を用意した。ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆い、電極面積は2mm×2mmとした。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
以上により得られた発光素子1、発光素子2を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
本発明の発光素子3は、発光層313におけるIr(dbq−P)2(acac)をIr(dbq−3FP)2(acac)(実施の形態3の構造式(55))に換えた以外は発光素子1と同様に作製した。また、比較発光素子である発光素子4は、発光層313におけるIr(dbq−P)2(acac)をIr(dbq−3FP)2(acac)に換えた以外は、発光素子2と同様に作製した。
以上により得られた発光素子3、発光素子4を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
まず、窒素雰囲気にて、脱水エタノール100mLを溶媒とし、フェニルグリオキサール2.16gと9,10−ジアミノフェナントレン3.36gを溶解させ、還流により7時間反応させた。反応により析出してきた白色粉末をろ過し、ろ取物をエタノール、次いでエーテルにて洗浄することにより、目的のジベンゾ[f,h]キノキサリン誘導体Hdbq−Pを得た(収率92%)。ステップ1の合成スキームを下記(a−1)に示す。
前記ステップ1に続いて、2−エトキシエタノール24mLと水8mL、上記ステップ1で得たジベンゾ[f,h]キノキサリン誘導体Hdbq−P0.61g、塩化イリジウム水和物(IrCl3・H2O)(Sigma−Aldrich社製)0.30gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 200W)を5時間照射し、反応させた。反応溶液より析出してきた橙色粉末をろ過し、エタノールにて洗浄することにより、複核錯体[Ir(dbq−P)2Cl]2 を得た(収率78%)。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。また、ステップ2の合成スキームを下記(b−1)に示す。
前記ステップ2に続いて、2−エトキシエタノール25mL、上記ステップ2で得た複核錯体[Ir(dbq−P)2Cl]2 0.54g、アセチルアセトン0.10mL、炭酸ナトリウム0.34gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 200W)を30分間照射し、反応させた。反応溶液をろ過し、得られたろ液を濃縮乾固して、残渣を得た。この残渣をジクロロメタンにて再結晶し、本発明の有機金属錯体[Ir(dbq−P)2(acac)]を赤色粉末として得た(収率16%)。ステップ3の合成スキームを下記(c−1)に示す。
まず、窒素雰囲気にて、3−ブロモフルオロベンゼン6.87gと、テトラヒドロフラン40mLの混合溶液に、−78℃にてn−ブチルリチウムのヘキサン溶液(1.58mol/L)27.5mLを滴下した後、そのまま−78℃にて2時間撹拌した。得られた溶液に、−78℃にてジベンゾ[f,h]キノキサリン7.54gを5回に分けて添加し、反応温度を室温まで昇温し、そのまま室温にて12時間撹拌した。この混合物に水を加え、ジクロロメタンを抽出溶媒として有機層を抽出した。得られた有機層を無水硫酸マグネシウムにて乾燥した。乾燥した後の溶液をろ過した。この溶液の溶媒を留去した後、エタノールにて再結晶することにより、目的のキノキサリン誘導体Hdbq−3FPを得た(薄い橙色粉末、収率23%)。ステップ1の合成スキームを下記(a−2)に示す。
前記ステップ1に続いて、2−エトキシエタノール15mLと水5mL、上記ステップ1で得たキノキサリン誘導体Hdbq−3FP2.41g、塩化イリジウム水和物(IrCl3・H2O)(Sigma−Aldrich社製)1.01gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100〜250W)を6時間照射し、反応させた。反応溶液より析出してきた橙色粉末をろ過し、エタノールにて洗浄することにより、複核錯体[Ir(dbq−3FP)2Cl]2 を得た(収率70%)。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製 Discover)を用いた。また、ステップ2の合成スキームを下記(b−2)に示す。
前記ステップ2に続いて、2−エトキシエタノール20mL、上記ステップ2で得た複核錯体[Ir(dbq−3FP)2Cl]2 2.06g、アセチルアセトナトナトリウム水和物(Na(CH3COCHCOCH3).XH2O)0.43gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を30分間照射し、反応させた。反応溶液をろ過し、得られたろ液を濃縮乾固して、残渣を得た。この残渣をジクロロメタンに溶解してセライト(和光純薬工業株式会社、カタログ番号:531−16855)を通した後、ジクロロメタンにて再結晶することにより、ジベンゾ[f,h]キノキサリン系有機金属錯体[Ir(dbq−3FP)2(acac)]を赤色粉末として得ることができた(収率27%)。ステップ3の合成スキームを下記(c−2)に示す。
101 ホール輸送層
102 電子輸送層
111 第1の有機化合物のHOMO準位
112 第1の有機化合物のLUMO準位
121 第2の有機化合物のHOMO準位
122 第2の有機化合物のLUMO準位
131 ジベンゾ[f,h]キノキサリン系有機金属錯体のHOMO準位
132 ジベンゾ[f,h]キノキサリン系有機金属錯体のLUMO準位
200 発光層
201 ホール輸送層
202 電子輸送層
211 第1の有機化合物のHOMO準位
212 第1の有機化合物のLUMO準位
221 第2の有機化合物のHOMO準位
222 第2の有機化合物のLUMO準位
231 ジベンゾ[f,h]キノキサリン系有機金属錯体のHOMO準位
232 ジベンゾ[f,h]キノキサリン系有機金属錯体のLUMO準位
301 第1の電極
302 第2の電極
311 ホール注入層
312 ホール輸送層
313 発光層
314 電子輸送層
315 電子注入層
321 第1の有機化合物
322 第2の有機化合物
323 ジベンゾ[f,h]キノキサリン系有機金属錯体
401 筐体
402 液晶層
403 バックライト
404 筐体
405 ドライバIC
406 端子
411 筐体
412 光源
511 本体
512 筐体
513 表示部
514 キーボード
521 表示部
522 本体
523 アンテナ
524 音声出力部
525 音声入力部
526 操作スイッチ
531 表示部
532 筐体
533 スピーカー
601 駆動回路部(ソース側駆動回路)
602 画素部
603 駆動回路部(ゲート側駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 発光層を含む層
617 第2の電極
618 発光素子
623 Nチャネル型TFT
624 Pチャネル型TFT
951 基板
952 電極
953 絶縁層
954 隔壁層
955 発光層を含む層
956 電極
Claims (4)
- 第1の電極と第2の電極との間に発光層と、電子輸送層と、を有し、
前記発光層は、ホール輸送性を有する第1の有機化合物と、電子輸送性を有する第2の有機化合物と、有機金属錯体とを含み、
前記第1の有機化合物の量および/または前記第2の有機化合物の量は、前記有機金属錯体よりも多く、
前記有機金属錯体は式(G8)で表される有機金属錯体であり、
前記第1の有機化合物のLUMO準位および前記第2の有機化合物のLUMO準位に比べ、前記有機金属錯体のLUMO準位は0.2eV以上深い発光素子。
(式中、R 9 〜R 13 はそれぞれ、水素、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数6〜12のアリール基、またはハロゲン基のいずれかを表す。また、Mは中心金属であり、第9族元素、または第10族元素のいずれかを表す。また、Lはベータジケトン構造を有するモノアニオン性の二座キレート配位子、カルボキシル基を有するモノアニオン性の二座キレート配位子、フェノール性水酸基を有するモノアニオン性の二座キレート配位子、または2つの配位元素がいずれも窒素であるモノアニオン性の二座キレート配位子のいずれかを表す。また、前記中心金属が第9族元素のときはn=2であり、第10族元素の時はn=1である。) - 請求項1において、
前記中心金属がイリジウムまたは白金である発光素子。 - 請求項1または請求項2において、
前記第1の有機化合物は芳香族アミン化合物またはカルバゾール誘導体である発光素子。 - 請求項1乃至請求項3のいずれか一項において、
前記第2の有機化合物は複素芳香族化合物または金属錯体である発光素子。
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