KR101794558B1 - Organic metal compounds and organic light emitting diodes comprising the same - Google Patents
Organic metal compounds and organic light emitting diodes comprising the same Download PDFInfo
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- KR101794558B1 KR101794558B1 KR1020100039587A KR20100039587A KR101794558B1 KR 101794558 B1 KR101794558 B1 KR 101794558B1 KR 1020100039587 A KR1020100039587 A KR 1020100039587A KR 20100039587 A KR20100039587 A KR 20100039587A KR 101794558 B1 KR101794558 B1 KR 101794558B1
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- 150000002736 metal compounds Chemical class 0.000 title claims description 7
- 239000000126 substance Substances 0.000 claims abstract description 195
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 26
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 4
- 101710179738 6,7-dimethyl-8-ribityllumazine synthase 1 Proteins 0.000 claims description 4
- 101710186608 Lipoyl synthase 1 Proteins 0.000 claims description 4
- 101710137584 Lipoyl synthase 1, chloroplastic Proteins 0.000 claims description 4
- 101710090391 Lipoyl synthase 1, mitochondrial Proteins 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 4
- 101710179734 6,7-dimethyl-8-ribityllumazine synthase 2 Proteins 0.000 claims description 2
- 101710186609 Lipoyl synthase 2 Proteins 0.000 claims description 2
- 101710122908 Lipoyl synthase 2, chloroplastic Proteins 0.000 claims description 2
- 101710101072 Lipoyl synthase 2, mitochondrial Proteins 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 111
- 238000006243 chemical reaction Methods 0.000 description 88
- 239000010410 layer Substances 0.000 description 78
- 230000015572 biosynthetic process Effects 0.000 description 53
- 238000003786 synthesis reaction Methods 0.000 description 53
- 239000000463 material Substances 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000005103 alkyl silyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 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
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004020 luminiscence type Methods 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
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 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
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- MGHBDQZXPCTTIH-UHFFFAOYSA-N 1-bromo-2,4-difluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1 MGHBDQZXPCTTIH-UHFFFAOYSA-N 0.000 description 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-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
- VOTVZTINZSVDEM-UHFFFAOYSA-N 1h-pyridin-2-ylidenemethanone Chemical compound O=C=C1NC=CC=C1 VOTVZTINZSVDEM-UHFFFAOYSA-N 0.000 description 1
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- UPSWHSOSMRAWEH-UHFFFAOYSA-N 2-n,3-n,4-n-tris(3-methylphenyl)-1-n,1-n,2-n,3-n,4-n-pentakis-phenylbenzene-1,2,3,4-tetramine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 UPSWHSOSMRAWEH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 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 1
- XTHKRYHULUJQHN-UHFFFAOYSA-N 6-bromopyridin-3-amine Chemical compound NC1=CC=C(Br)N=C1 XTHKRYHULUJQHN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- IYEHOHCVXCAADZ-UHFFFAOYSA-N B(O)(O)O.COC1=CC=NC=C1 Chemical compound B(O)(O)O.COC1=CC=NC=C1 IYEHOHCVXCAADZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N CN(C)Cc1ccccc1 Chemical compound CN(C)Cc1ccccc1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 0 CN1c2ccccc2*(C2)C1*c(cc1F)c2c(F)c1C#N Chemical compound CN1c2ccccc2*(C2)C1*c(cc1F)c2c(F)c1C#N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical class COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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Abstract
본 발명은 하기 [화학식 1]로 표시되는 신규한 유기금속 화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로서, 본 발명에 따른 유기금속 화합물을 포함하는 유기전계발광소자는 외부양자효율이 우수하다.
[화학식 1]
[Chemical Formula 1]
Description
본 발명은 유기금속 화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로서, 보다 상세하게는 높은 양자효율을 가지는 유기금속 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic metal compound and an organic electroluminescent device including the same, and more particularly, to an organic metal compound having high quantum efficiency and an organic electroluminescent device including the same.
최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT(cathode ray tube)에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color)디스플레이 또는 조명으로의 응용이 기대되고 있다.In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon and has a wide viewing angle and can be made thinner and thinner than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected.
유기 발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.
그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.
유기전계발광소자가 전술한 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전계발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 당 기술분야에서는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.
발광 재료에서 발광 원리를 살펴보면, 양쪽 전극에서부터 주입된 전자와 정공이 결합에 의해 엑시톤(여기자)을 형성하는데, 이때 일중항 여기자의 경우 형광, 삼중항 여기자의 경우 인광에 관여한다. 생성 확률이 75%인 삼중항 여기자를 사용하는 인광재료는 생성 확률이 25%인 일중항 여기자를 사용하는 형광재료보다 뛰어난 발광 효율을 보인다.The principle of luminescence in a light emitting material is that excitons (excitons) are formed by the combination of electrons and holes injected from both electrodes. In this case, fluorescence in singlet excitons and phosphorescence in triplet excitons are involved. A phosphorescent material using a triplet exciton having a generation probability of 75% exhibits a luminous efficiency higher than that of a fluorescent material using a singlet exciton having a generation probability of 25%.
유기전계발광소자에 적용될 수 있는 고효율 인광체들은 매우 제한적인데, 인광 발광이 용이한 분자구조로는 계간전이가 용이한 분자 구조로 원자번호가 큰 금속을 포함하는 금속 착체로서 Ir, Pt, Eu, Tb, Re, Rh, Os 등의 전이금속을 이용한 인광물질의 개발이 진행되고 있고, 리간드의 종류에 따라서 발광특성이 결정된다.High efficiency phosphors that can be applied to organic electroluminescent devices are very limited. In molecular structures that can easily emit phosphorescence, Ir, Pt, Eu, and Tb are used as metal complexes containing a metal having a large atomic number, , Re, Rh, Os, and the like, and the luminescence characteristics are determined depending on the type of the ligand.
다만, 휘도가 낮고 물질의 안정성이 떨어져 실제 소자에 적용하기에는 한계가 있어 신규 발광물질에 대한 연구가 활발히 진행되고 있고, 그 중에서도 이리듐 착체 화합물은 인광 발광효율이 우수한 물질로 주목받고 있다.However, since the brightness is low and the stability of the material is low, there is a limit to be applied to an actual device. Therefore, studies on a novel luminescent material have been actively carried out. Among them, iridium complex compounds are attracting attention as materials having excellent phosphorescent luminescent efficiency.
본 발명이 해결하고자 하는 첫 번째 기술적 과제는 외부양자효율이 우수한 유기금속 화합물을 제공하는 것이다.The first technical problem to be solved by the present invention is to provide an organometallic compound excellent in external quantum efficiency.
본 발명이 해결하고자 하는 두 번째 기술적 과제는 상기 유기금속 화합물을 포함하는 유기전계발광소자를 제공하는 것이다.A second object of the present invention is to provide an organic electroluminescent device including the organometallic compound.
상기 첫 번째 기술적 과제를 달성하기 위해서, 본 발명은 하기 [화학식 1]로 표시되는 유기금속 화합물을 제공한다.In order to achieve the first technical object, the present invention provides an organometallic compound represented by the following Chemical Formula 1.
[화학식 1][Chemical Formula 1]
상기 [화학식 1]에서,In the above formula (1)
Ar1 및 Ar3는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기, 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴기이고,Ar 1 And Ar 3 each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
Ar2는 적어도 하나의 질소 원자를 포함하는 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴기이며,Ar 2 is a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms containing at least one nitrogen atom,
R은 수소원자, 중수소원자, 시아노기, 할로겐원자, 히드록시기, 니트로기, 치환 또는 비치환된 탄소수 1 내지 40의 알킬기, 치환 또는 비치환된 탄소수 1 내지 40의 알콕시기, 치환 또는 비치환된 탄소수 1 내지 40의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴아미노기, 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 40의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴실릴기, 치환 또는 비치환된 탄소수 6 내지 40의 아릴기, 치환 또는 비치환된 탄소수 3 내지 40의 아릴옥시기, 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인 및 보론으로 이루어진 군으로부터 선택되고,R represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamino group having 3 to 40 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylamino group having 1 to 40 carbon atoms, A substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, An aryl group, a germanium group, phosphorus, and boron,
L은 단결합 또는 치환 또는 비치환된 탄소수 1 내지 4의 알킬렌이고,L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,
n은 0 내지 3의 정수이다.n is an integer of 0 to 3;
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상기 두 번째 기술적 과제를 해결하기 위하여, 본 발명은 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 유기금속 화합물을 포함하는 층을 구비한 유기전계발광소자를 제공한다.In order to solve the second technical problem, the present invention provides a semiconductor device comprising: an anode; Cathode; And a layer interposed between the anode and the cathode and including an organometallic compound represented by the formula (1).
도 1은 본 발명의 일 구체예에 따른 유기전계발광소자의 개략도이다.
도 2는 본 발명의 [화학식 1]에 따른 유기금속 화합물의 구조를 나타낸 대표도이다.
<도면의 주요부분에 대한 부호의 설명>
10 : 기판 20 : 애노드
30 : 정공주입층 40 : 정공수송층
50 : 유기발광층 60 : 전자수송층
70 : 전자주입층 80 : 캐소드1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.
2 is a representative view showing the structure of an organometallic compound according to the formula (1) of the present invention.
Description of the Related Art
10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에 따른 유기금속 화합물은 종래 이리듐 착제 화합물보다 인광발광효율을 개선시킨 것으로서, 상기 [화학식 1]로 표시되는 것과 같이 이리듐 착제에 다양한 종류의 리간드가 결합된 것을 특징으로 하고, 보다 구체적으로는 상기 [화학식 2] 내지 [화학식 6]으로 표시되는 화합물 중에서 어느 하나인 것을 특징으로 한다.The organometallic compound according to the present invention is improved in phosphorescent emission efficiency over the conventional iridium complexing compound, and is characterized in that various types of ligands are bonded to the iridium complex as represented by the formula (1). More specifically, Is a compound represented by any one of the above formulas (2) to (6).
본 발명에 따른 유기금속 화합물에 있어서, 상기 [화학식 1] 내지 [화학식 6]의 치환기들을 보다 구체적으로 설명하면 하기와 같다.In the organometallic compound according to the present invention, the substituents of the above formulas (1) to (6) will be described in more detail as follows.
상기 [화학식 1]에서 인접한 작용기는 서로 결합하여 포화 또는 불포화 고리인 지방족, 방향족, 헤테로지방족 또는 헤테로방향족의 축합고리를 형성할 수 있고 펜던트 방법으로 함께 부착되거나 또는 융합될 수 있다.In the above formula (1), adjacent functional groups may bond to each other to form a condensed ring of a saturated or unsaturated aliphatic, aromatic, heteroaliphatic or heteroaromatic ring and may be attached together or fused together by a pendant method.
상기 [화학식 1]에서 치환기는 각각 독립적으로 수소원자, 중수소 원자, 시아노기, 할로겐 원자, 히드록시기, 니트로기, 탄소수 1 내지 40의 알킬기, 탄소수 1 내지 40의 알콕시기, 탄소수 1 내지 40의 알킬아미노기, 탄소수 6 내지 40의 아릴아미노기, 탄소수 3 내지 40의 헤테로아릴아미노기, 탄소수 1 내지 40의 알킬실릴기, 탄소수 6 내지 40의 아릴실릴기, 탄소수 6 내지 40의 아릴기, 탄소수 3 내지 40의 아릴옥시기, 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인 및 보론으로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환될 수 있고, 상기 치환기에 의해 추가로 치환될 수 있다. 상기 치환기는 서로 결합하여 포화 또는 불포화 고리인 지방족, 방향족, 헤테로지방족 또는 헤테로방향족의 축합고리를 형성할 수 있고 펜던트 방법으로 함께 부착되거나 또는 융합될 수 있다.In the above formula 1, each substituent is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, , An arylamino group having 6 to 40 carbon atoms, a heteroarylamino group having 3 to 40 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 40 carbon atoms An oxygen atom, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus, and boron, and may be further substituted by the substituent. The substituents may be bonded to each other to form a condensed ring of a saturated or unsaturated aliphatic, aromatic, heteroaliphatic or heteroaromatic ring and may be attached together or fused together by a pendant method.
본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 펜틸기, iso-아밀기, 헥실기, 헵틸기, 옥틸기, 스테아릴기, 트리클로로메틸기, 트리플루오르메틸기 등을 들 수 있으며, 상기 알킬기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 트리플루오로메틸기, 실릴기(이 경우 “알킬실릴기”라 함), 치환 또는 비치환된 아미노기(-NH2,-NH(R),-N(R')(R''),여기서 R, R' 및 R"은 각각 독립적으로 탄소수 1 내지 24의 알킬기임(이 경우 “알킬아미노기”라 함)), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 5 내지 24의 아릴기, 탄소수 6 내지 24의 아릴알킬기, 탄소수 3 내지 24의 헤테로아릴기 또는 탄소수 3 내지 24의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " alkylsilyl group "hereinafter), a substituted or unsubstituted amino group (-NH 2, -NH (R) , - N (R ') (R''), where R, R' and R" are each independently a carbon number A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms (for example, an alkyl group having 1 to 24 carbon atoms , An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a carbon An aryl group having 5 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 3 to 24 carbon atoms, or a heteroarylalkyl group having 3 to 24 carbon atoms.
본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.
본 발명의 화합물에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.
본 발명의 화합물에서 사용되는 치환기인 아릴기의 구체적인 예로는 페닐기, 2-메틸페닐기, 3-메틸페닐기, 4-메틸페닐기, 4-에틸페닐기, o-비페닐기, m-비페닐기, p-비페닐기, 4-메틸비페닐기, 4-에틸비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 1-나프틸기, 2-나프틸기, 1-메틸나프틸기, 2-메틸나프틸기, 안트릴기, 페난트릴기, 피레닐기, 플루오레닐기, 테트라히드로나프틸기 등과 같은 방향족 그룹을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those in the case of the alkyl group.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기의 구체적인 예로는 피리디닐기, 피리미디닐기, 트리아지닐기, 인돌리닐기, 퀴놀린닐기, 피롤리디닐기, 피페리디닐기, 모폴리디닐기, 피페라디닐기, 카바졸릴기, 옥사졸릴기, 옥사디아졸릴기, 벤조옥사졸릴기, 치아졸릴기, 치아디아졸릴기, 벤조치아졸릴기, 트리아졸릴기, 이미다졸릴기, 벤조이미다졸기 등이 있으며, 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.
본 발명에 있어서, “치환 또는 비치환된”이라는 용어는 중수소, 할로겐기, 알킬기, 알케닐기, 알콕시기, 아릴기, 아릴알킬기, 아릴알케닐기, 헤테로아릴기, 카바졸릴기, 플루오레닐기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heteroaryl, Substituted or unsubstituted with at least one substituent selected from the group consisting of an acetylene group, a nitrile group and an acetylene group.
본 발명에 따른 유기금속 화합물에 있어서, 상기 [화학식 1]에서 
는 보다 구체적으로 하기 구조식 [LS 1] 내지 [LS 32]로 표시되는 화합물 중 어느 하나일 수 있다.May be more specifically any of the compounds represented by the following structural formulas [LS 1] to [LS 32].
[LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6][LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6]
[LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13][LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13]
[LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20][LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20]
[LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27][LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27]
[LS 28] [LS 29] [LS 30] [LS 31] [LS 32][LS 28] [LS 29] [LS 30] [LS 31] [LS 32]
본 발명에 따른 유기금속 화합물에 있어서, 상기 [화학식 1]에서
[LS 33] [LS 34] [LS 35] [LS 36] [LS 37][LS 33] [LS 34] [LS 35] [LS 36] [LS 37]
[LS 38] [LS 39] [LS 40] [LS 41] [LS 42][LS 38] [LS 39] [LS 40] [LS 41] [LS 42]
본 발명에 따른 유기금속 화합물에 있어서, 상기 [화학식 1]은 하기 [화학식 7] 내지 [화학식 214]로 표시되는 화합물 중 어느 하나일 수 있다.In the organometallic compound according to the present invention, the formula 1 may be any one of the compounds represented by the following formulas (7) to (214).
[화학식 7] [화학식 8] [화학식 9] [화학식 10][Chemical Formula 8] < EMI ID =
[화학식 11] [화학식 12] [화학식 13] [화학식 14][Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]
[화학식 15] [화학식 16] [화학식 17] [화학식 18][Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]
[화학식 19] [화학식 20] [화학식 21] [화학식 22][Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]
[화학식 23] [화학식 24] [화학식 25] [화학식 26][Chemical Formula 25] [Chemical Formula 25]
[화학식 27] [화학식 28] [화학식 29] [화학식 30][Chemical Formula 30] [Chemical Formula 30]
[화학식 31] [화학식 32] [화학식 33] [화학식 34][Chemical Formula 32] [Chemical Formula 32]
[화학식 35] [화학식 36] [화학식 37] [화학식 38][Chemical Formula 35] [Chemical Formula 35]
[화학식 39] [화학식 40] [화학식 41] [화학식 42][Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]
[화학식 43] [화학식 44] [화학식 45] [화학식 46][Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 45]
[화학식 47] [화학식 48] [화학식 49] [화학식 50][Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]
[화학식 51] [화학식 52] [화학식 53] [화학식 54][Chemical Formula 51]
[화학식 55] [화학식 56] [화학식 57] [화학식 58][Chemical Formula 55] [Chemical Formula 55]
[화학식 59] [화학식 60] [화학식 61] [화학식 62][Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62]
[화학식 63] [화학식 64] [화학식 65] [화학식 66][Chemical Formula 65] [Chemical Formula 65]
[화학식 67] [화학식 68] [화학식 69] [화학식 70][Chemical Formula 70] [Chemical Formula 70]
[화학식 71] [화학식 72] [화학식 73] [화학식 74][Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74]
[화학식 75] [화학식 76] [화학식 77] [화학식 78][Formula 75] < EMI ID = 78.1 >
[화학식 79] [화학식 80] [화학식 81] [화학식 82][Formula 80] [Formula 81] [Formula 82]
[화학식 83] [화학식 84] [화학식 85] [화학식 86][Formula 83] [Formula 85] [Formula 86]
[화학식 87] [화학식 88] [화학식 89] [화학식 90][Formula 90] [Formula 90] [Formula 90]
[화학식 91] [화학식 92] [화학식 93] [화학식 94][Chemical Formula 91] [Chemical Formula 93] [Chemical Formula 94]
[화학식 95] [화학식 96] [화학식 97] [화학식 98][Chemical Formula 97] [Chemical Formula 97] [Chemical Formula 98]
[화학식 99] [화학식 100] [화학식 101] [화학식 102][Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 101]
[화학식 103] [화학식 104] [화학식 105] [화학식 106][Formula 103] [Formula 105] [Formula 106]
[화학식 107] [화학식 108] [화학식 109] [화학식 110][Formula 110] [Formula 110] [Formula 110]
[화학식 111] [화학식 112] [화학식 113] [화학식 114][Formula 111] [Formula 113] [Formula 114]
[화학식 115] [화학식 116] [화학식 117] [화학식 118][Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118]
[화학식 119] [화학식 120] [화학식 121] [화학식 122][Chemical Formula 120]
[화학식 123] [화학식 124] [화학식 125] [화학식 126][Formula 124] [Formula 125] [Formula 126]
[화학식 127] [화학식 128] [화학식 129] [화학식 130][Formula 127] < EMI ID = 129.0 >
[화학식 131] [화학식 132] [화학식 133] [화학식 134][Formula 131] [Formula 133] [Formula 134]
[화학식 135] [화학식 136] [화학식 137] [화학식 138][Chemical Formula 135] [Chemical Formula 135]
[화학식 139] [화학식 140] [화학식 141] [화학식 142][Formula 140] [Formula 141] [Formula 142]
[화학식 143] [화학식 144] [화학식 145] [화학식 146][Chemical Formula 144] [Chemical Formula 145] [Chemical Formula 146]
[화학식 147] [화학식 148] [화학식 149] [화학식 150][Formula 150] [Formula 149] [Formula 150]
[화학식 151] [화학식 152] [화학식 153] [화학식 154][Formula 154] [Formula 154] [Formula 154]
[화학식 155] [화학식 156] [화학식 157] [화학식 158][Formula 157] < EMI ID = 158.1 >
[화학식 159] [화학식 160] [화학식 161] [화학식 162][Formula 161] [Formula 161] [Formula 161]
[화학식 163] [화학식 164] [화학식 165] [화학식 166][Formula 166] [Formula 166] [Formula 166]
[화학식 167] [화학식 168] [화학식 169] [화학식 170][Formula 16] [Formula 16]
[화학식 171] [화학식 172] [화학식 173] [화학식 174][Formula 173] [Formula 174] [Formula 174]
[화학식 175] [화학식 176] [화학식 177] [화학식 178][Formula 177] [Formula 177] [Formula 178]
[화학식 179] [화학식 180] [화학식 181] [화학식 182][Formula 181] [Formula 181] [Formula 182]
[화학식 183] [화학식 184] [화학식 185] [화학식 186][Formula 184] [Formula 184] [Formula 186] [Formula 186]
[화학식 187] [화학식 188] [화학식 189] [화학식 190][Formula 188] [Chemical Formula 189] [Chemical Formula 190]
[화학식 191] [화학식 192] [화학식 193] [화학식 194][193] [193] [193] [194]
[화학식 195] [화학식 196] [화학식 197] [화학식 198][197] [198] [198] [198] [198]
[화학식 199] [화학식 200] [화학식 201] [화학식 202][Chemical Formula 200] [Chemical Formula 201] [Chemical Formula 202]
[화학식 203] [화학식 204] [화학식 205] [화학식 206][Chemical Formula 203]
[화학식 207] [화학식 208] [화학식 209] [화학식 210][Chemical Formula 20] [Chemical Formula 20] [Chemical Formula 20]
[화학식 211] [화학식 212] [화학식 213] [화학식 214][Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214]
본 발명에 따른 유기금속 화합물의 제조방법은 후술하는 실시예에 구체적으로 나타내었다.The method for producing an organometallic compound according to the present invention is specifically shown in the following Examples.
또한, 본 발명은 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 유기 금속 화합물을 포함하는 층을 구비한 유기전계발광소자를 제공한다.The present invention also relates to a fuel cell comprising an anode; Cathode; And a layer interposed between the anode and the cathode and including an organometallic compound represented by the formula (1).
이 때, 상기 유기금속 화합물이 함유된 층은 상기 애노드 및 캐소드 사이의 발광층인 것이 바람직하며, 애노드 및 캐소드 사이에는 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.In this case, the layer containing the organic metal compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, ≪ RTI ID = 0.0 > and / or < / RTI >
구체적인 예로서, 정공수송층(HTL, Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL, Electron Transport Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본 골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다.As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.
본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐벤지딘 (a-NPD) 등을 사용할 수 있다.In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).
상기 정공수송층의 하부에는 정공주입층(HIL, Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 CuPc(copper phthalocyanine) 또는 스타버스트(Starburst)형 아민류인 TCTA(4,4,4''-tri(N- carbazolyl)triphenyl-amine), m-MTDATA(4,4',4''-tris-(3-methylphenylphenyl amino)triphenylamine) 등을 사용할 수 있다.A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4,4 "-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4 ', 4" tris - (3-methylphenylphenylamino) triphenylamine).
또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 상기 전자수송층 재료로는 당 기술분야에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq3등을 사용할 수 있다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq 3 can be used.
한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL, Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O,BaO등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li 2 O, and BaO can be used.
본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다.The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.
도 1은 본 발명의 유기전계발광소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기전계발광소자는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an
도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조방법에 대하여 살펴보면 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2),산화아연(ZnO) 등을 사용한다.The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. First, an anode electrode material is coated on the
상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다.A
이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.A hole blocking layer (not shown) is selectively formed on the organic
이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.After the
또한, 본 발명의 다른 일 실시예에 의하면, 상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용될 수 있다.According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나 이들의 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further illustrating the present invention and that the scope of the present invention is not limited thereby.
<합성예 1> [화학식 7]로 표시되는 화합물의 제조Synthesis Example 1 Synthesis of Compound Represented by Formula 7
(1) [화학식 1-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (1-a)
하기 [반응식 1]에 의하여 [화학식 1-a]로 표시되는 화합물을 합성하였다.A compound represented by the formula (1-a) was synthesized by the following reaction scheme (1).
[반응식 1][Reaction Scheme 1]
[화학식 1-a] [Chemical Formula 1-a]
1L 둥근 바닥 플라스크에 벤질브로마이드 50.0g(0.292mol), 디에틸에테르(500ml)을 넣은 다음 50wt% 디메틸아민 65.8g(1.462mol)을 천천히 가한 후 상온에서 12시간 동안 교반한다. 유기층을 분리 후 10wt% 시트릭산으로 추출한 다음 수용액층을 15wt% 수산화나트륨 용액으로 중화한다. 중화된 수용액층을 디에틸에테르로 추출한 다음 건조 및 용매 제거하여 [화학식 1-a]를 합성하였다. (수율 35.1g 89%)50.0 g (0.292 mol) of benzyl bromide and 500 ml of diethyl ether were placed in a 1 L round bottom flask, and 65.8 g (1.462 mol) of 50% by weight of dimethylamine was slowly added thereto, followed by stirring at room temperature for 12 hours. The organic layer is separated and extracted with 10 wt% citric acid, and then the aqueous layer is neutralized with 15 wt% sodium hydroxide solution. The neutralized aqueous layer was extracted with diethyl ether, and then dried and solvent removed to synthesize [Formula 1-a]. (Yield: 35.1 g 89%)
(2) [화학식 1-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula (1-b)
하기 [반응식 2]에 의하여 [화학식 1-b]로 표시되는 화합물을 합성하였다.[Chemical Formula 1-b] was synthesized by the following Reaction Scheme 2.
[반응식 2][Reaction Scheme 2]
[화학식 1-b] [Chemical Formula 1-b]
500ml 둥근 바닥 플라스크에 브로모디플로로벤젠 36.0g(0.19mol), 2-트리부틸스텐닐피리딘 82.4g(0.22mol), Pd(PPh3)410.8g(0.009mol)을 톨루엔(360ml)에 녹인 후 120℃에서 18시간 동안 환류시킨다. 용매를 제거 후 헥산, 에틸아세테이트를 전개용매로 하여 컬럼크로마토그래피로 분리하여 [화학식 1-b]로 표시되는 화합물을 얻었다. (수율 28 g 79%)Dissolved in 500ml of benzene in a round-bottom flask with bromo-modify flow 36.0g (0.19mol), 2- tributyl stent carbonyl pyridin 82.4g (0.22mol), Pd (PPh 3) 4 10.8g of (0.009mol) in toluene (360ml) And then refluxed at 120 ° C for 18 hours. After removal of the solvent, the residue was purified by column chromatography using hexane and ethyl acetate as eluent to obtain the compound represented by the formula (1-b). (Yield 28 g 79%)
(3) [화학식 1-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula (1-c)
하기 [반응식 3]에 의하여 [화학식 1-c]로 표시되는 화합물을 합성하였다.The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].
[반응식 3][Reaction Scheme 3]
[화학식 1-c] [Chemical Formula 1-c]
250ml의 둥근바닥 플라스크에 상기 [반응식 2]로부터 얻은 [화학식 1-b] 20.0g(0.105mol), IrCl3.xH2O12.5g(0.042mol)과 에톡시에탄올(210ml), 물(70ml) 혼합용액을 넣은 후 120℃ 에서 18시간 환류시킨다. 온도를 상온으로 내린 다음 물(1L)에 붓고 생성된 고형물을 여과한 후 물, 메탄올, 디에틸에테르, 헥산으로 세척하여 [화학식 1-c]를 제조하였다. (수율 18.8g 74%)20.0 g (0.105 mol) of [Formula 1-b], 12.5 g (0.042 mol) of IrCl 3 .xH 2 O, 210 ml of ethoxyethanol and 70 ml of water were added to a 250 ml round bottom flask, After the mixed solution is added, the mixture is refluxed at 120 ° C for 18 hours. The temperature was lowered to room temperature, poured into water (1 L), and the resulting solid was filtered, washed with water, methanol, diethyl ether, and hexane to prepare [formula I-c]. (Yield: 18.8 g 74%)
(4) [화학식 7]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 7
하기 [반응식 4]에 의하여 [화학식 7]로 표시되는 화합물을 합성하였다.A compound represented by the formula (7) was synthesized by the following reaction scheme (4).
[반응식 4][Reaction Scheme 4]
[화학식 7] (7)
질소기류하에서 250ml의 둥근바닥 플라스크에 상기 [반응식 3]으로부터 얻은 [화학식 1-c] 15.0g(0.012mol), THF(150ml)을 넣고 -78℃에서 노르말뷰틸리튬 15.2g(0.037mol)을 천천히 가한 다음 1시간 동안 교반한다. 동일한 온도에서 상기 [반응식 1]로부터 얻은 [화학식 1-a], 4.5g(0.031mol)을 가하고 18시간 동안 상온에서 교반하였다. 염화암모늄 수용액과 디클로로메탄 이용하여 유기층을 분리하고 건조 및 감압 농축한 후 디클로로메탄, 헥산 전개용매로 컬럼크로마토그래피를 사용하여 [화학식 7]로 표시되는 화합물을 합성하였다. (수율 18.8g 74%)15.0 g (0.012 mol) of the compound [1-c] obtained from the
MS(MALDI-TOF): m/z 707[M]+; Anal. Calcd.MS (MALDI-TOF): m / z 707 [M] < + >; Anal. Calcd.
C31H24F4IrN3:C,52.68;H,3.42;N,5.95.Found:C,51.82;H,3.35;N,6.01.C 31 H 24 F 4 IrN 3 : C, 52.68; H, 3.42; N, 5.95.Found: C, 51.82, H, 3.35;
<합성예 2> [화학식 10]으로 표시되는 화합물의 제조Synthesis Example 2 Synthesis of the compound represented by the formula (10)
(1) [화학식 2-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (2-a)
하기 [반응식 5]에 의하여 [화학식 2-a]로 표시되는 화합물을 합성하였다.A compound represented by the general formula [2-a] was synthesized by the following reaction scheme [5].
[반응식 5][Reaction Scheme 5]
[화학식 2-a] [Chemical Formula 2-a]
상기 [반응식 1]의 [화학식 1-a] 합성과 동일한 절차를 통하여 [화학식 2-a]를 합성하였다. (수율 14.4g 85.1%)[Formula 2-a] was synthesized through the same procedure as the synthesis of [Formula 1-a] in [Reaction Scheme 1]. (Yield: 14.4 g 85.1%)
(2) [화학식 10]으로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by
하기 [반응식 6]에 의하여 [화학식 10]으로 표시되는 화합물을 합성하였다.A compound represented by the formula (10) was synthesized by the following reaction scheme (6).
[반응식 6][Reaction Scheme 6]
[화학식 10] [Chemical formula 10]
상기 [반응식 3]으로부터 얻은 [화학식 1-c]로 표시되는 화합물과 [반응식 5]로부터 얻은 [화학식 2-a]을 가지고 상기 [반응식 4]의 [화학식 7]의 합성과 동일한 절차를 통하여 [화학식 10]으로 표시되는 화합물을 합성하였다. (수율 14.4g 85.1%)The same procedure as in the synthesis of the compound of the formula [7] in the reaction scheme 4 with the compound of the formula 1-c and the compound of the formula 2-a obtained from the
MS(MALDI-TOF): m/z 775[M]+; Anal. Calcd.MS (MALDI-TOF): m / z 775 [M] < + >; Anal. Calcd.
C32H23F7IrN3:C,49.61;H,2.99;N,5.42.Found:C,49.11;H,2.91;N,5.49.C 32 H 23 F 7 IrN 3 : C, 49.61; H, 2.99; N, 5.42. Found: C, 49.11; H, 2.91; N, 5.49.
<합성예 3> [화학식 17]로 표시되는 화합물의 제조≪ Synthesis Example 3 > Preparation of a compound represented by the formula (17)
(1) [화학식 3-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula 3-a
하기 [반응식 7]에 의하여 [화학식 3-a]로 표시되는 화합물을 합성하였다.A compound represented by the formula (3-a) was synthesized by the following reaction scheme [7].
[반응식 7][Reaction Scheme 7]
[화학식 3-a] [Formula 3-a]
상기 [반응식 1]의 [화학식 1-a]의 합성과 동일한 절차를 통하여 [화학식 3-a]을 합성하였다. (수율 13.6g 83.1%)[Formula 3-a] was synthesized through the same procedure as the synthesis of [Formula 1-a] in Reaction Scheme 1 above. (Yield: 13.6 g 83.1%)
(2) [화학식 3-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 3-b
하기 [반응식 8]에 의하여 [화학식 3-b]로 표시되는 화합물을 합성하였다.A compound represented by the formula (3-b) was synthesized by the following Reaction Scheme 8.
[반응식 8][Reaction Scheme 8]
[화학식 3-b] [Formula 3-b]
1L 둥근 바닥 플라스크에 수산화칼륨 51.29g(0.914mol), N,N-디메틸포름아마이드 513ml를 투입한 후 상온에서 5분간 교반을 하였다. 5분 후 벤즈이미다졸 27g(0.229mol)을 넣고 상온에서 2시간 교반하였다. 2시간 후 반응액을 0℃로 낮춘 후 4-브로모벤질브로마이드 114.24g(0.343mol)을 넣어주었다. 반응이 종결되면, 반응액에 물을 넣고 교반을 하다가 층분리하여 수층을 제거하고 유기층을 분리하여 감압농축 한 후, 헥산을 부어 결정을 잡은 후 건조하여 [화학식 3-b]을 제조하였다. (수율 48g 73%)51.29 g (0.914 mol) of potassium hydroxide and 513 ml of N, N-dimethylformamide were added to a 1 L round bottom flask, followed by stirring at room temperature for 5 minutes. After 5 minutes, 27 g (0.229 mol) of benzimidazole was added and the mixture was stirred at room temperature for 2 hours. After 2 hours, the reaction solution was cooled to 0 ° C, and 114.24 g (0.343 mol) of 4-bromobenzyl bromide was added. When the reaction was completed, water was added to the reaction mixture, and the mixture was stirred to remove the water layer. The organic layer was separated, concentrated under reduced pressure, and then poured into hexane to obtain crystals, followed by drying to prepare [Formula 3-b]. (Yield: 48 g 73%)
(3) [화학식 3-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 3-c
하기 [반응식 9]에 의하여 [화학식 3-c]로 표시되는 화합물을 합성하였다.[Chemical Formula 3-c] was synthesized by the following Reaction Scheme 9.
[반응식 9][Reaction Scheme 9]
[화학식 3-c] [Chemical Formula 3-c]
2L 둥근 바닥 플라스크에 1-브로모-2,4-다이플루오로벤젠 100g(0.518mol), 디에틸에테르 1L를 투입한 후 -78℃에서 1시간 동안 교반시켜 주었다. 노르말뷰틸리튬(n-butyl lithium 1.6M) 388.62ml(0.622mol)을 천천히 적가하였다. 2시간 뒤 트리아이소프로필 보레이트 146.18g(0.777mol)을 천천히 적가해 준 후 상온으로 온도를 올려주었다. 2시간 뒤 2N 염산으로 pH를 산으로 맞추었다. 추출하여 유기층을 모아 날린 후 헥산을 과량 부어 결정을 잡은 후 건조한 결과 [화학식 3-c]를 제조하였다. (수율 54.8g 67%)100 g (0.518 mol) of 1-bromo-2,4-difluorobenzene and 1 L of diethyl ether were added to a 2 L round bottom flask, followed by stirring at -78 ° C for 1 hour. 388.62 ml (0.622 mol) of n-butyl lithium 1.6M was slowly added dropwise. After 2 hours, 146.18 g (0.777 mol) of triisopropylborate was added dropwise and the temperature was raised to room temperature. After 2 hours, the pH was adjusted to acid with 2N hydrochloric acid. The organic layer was collected by blowing, and then hexane was poured excessively to obtain crystals. The crystals were dried to give [Formula 3-c]. (Yield: 54.8 g, 67%)
(4) [화학식 3-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 3-d
하기 [반응식 10]에 의하여 [화학식 3-d]로 표시되는 화합물을 합성하였다[Chemical Formula 3-d] was synthesized by the following
[반응식 10][Reaction Scheme 10]
[화학식 3-d] [Chemical formula 3-d]
2L 둥근 바닥 플라스크에 상기 [반응식 8] 및 [반응식 9]로부터 얻은 [화학식 3-b]로 표시되는 화합물 40g(0.139mol), [화학식 3-c]로 표시되는 화합물 26.4g(0.167mol), 탄산칼륨 77.01g(0.577mol), 테트라키스트리페닐포스핀팔라듐 8.06g(0.007mol), 물 200ml, 톨루엔 400ml, 에탄올 200ml를 투입한 후 80℃에서 24시간 동안 환류시켰다. 반응이 종결되면, 반응의 결과물을 층분리하여 수층을 제거하고 유기층을 분리하여 감압농축 한 후, 헥산을 부어 결정을 잡은 후 건조하여 [화학식 3-d]를 제조하였다. (수율 40g 88.6%)40 g (0.139 mol) of the compound represented by the formula [3-b], 26.4 g (0.167 mol) of the compound represented by the formula 3-c, (0.0077 mol) of tetrakis (triphenylphosphine) palladium, 200 ml of water, 400 ml of toluene and 200 ml of ethanol were charged and refluxed at 80 ° C for 24 hours. After completion of the reaction, the reaction product was separated into layers and the water layer was removed. The organic layer was separated, concentrated under reduced pressure, and then poured into hexane to obtain crystals, followed by drying to prepare [Formula 3-d]. (Yield: 40 g 88.6%)
(5) [화학식 3-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 3-e
하기 [반응식 11]에 의하여 [화학식 3-e]로 표시되는 화합물을 합성하였다.[Chemical Formula 3-e] was synthesized by the following Reaction Scheme 11.
[반응식 11][Reaction Scheme 11]
[화학식 3-e] [Formula 3-e]
500ml 둥근 바닥 플라스크에 상기 [반응식 10]으로부터 얻은 [화학식 3-d]로 표시되는 화합물 40g(0.125mol), 톨루엔 400ml를 넣고 70℃까지 가열하였다. 반용액이 투명해지면 요오도메탄 26.6g(0.187mol)을 넣고 18시간 동안 교반하였다. 반응이 종결되면 상온으로 온도를 내린 후 필터하여 [화학식 3-e]를 얻었다. (수율 53g 91.8%)40 g (0.125 mol) of the compound represented by the formula [3-d] obtained from the above-mentioned
(6) [화학식 3-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 3-f
하기 [반응식 12]에 의하여 [화학식 3-f]로 표시되는 화합물을 합성하였다.[Chemical Formula 3-f] was synthesized by the following Reaction Scheme 12.
[반응식 12][Reaction Scheme 12]
[화학식 3-f] [Chemical Formula 3-f]
1L 둥근 바닥 플라스크에 [Ir(COD)Cl]26.1g(0.009mol),메톡시나트륨 4.8g (0.090mol), 2-에톡시에탄올 500ml을 넣고 상온에서 2시간 동안 교반한다. 이 반응물에 상기 [반응식 11]으로부터 얻은 [화학식 3-e]로 표시되는 화합물 30g 0.045mol)을 넣고 135℃에서 3시간 동안 환류시켰다. 온도를 상온으로 내린 다음 감압증류하여 용매를 제거하고 디클로로메탄 전개용매로 컬럼크로마토그래피를 사용하여 [화학식 3-f]를 합성하였다. (수율 12.5g 55%)6.1 g (0.009 mol) of [Ir (COD) Cl] 2 , 4.8 g (0.090 mol) of methoxysodium and 500 ml of 2-ethoxyethanol were placed in a 1 L round bottom flask and stirred at room temperature for 2 hours. To the reaction mixture, 30 g (0.045 mol) of the compound represented by the formula (3-e) obtained from the above-mentioned scheme [11] was added and the mixture was refluxed at 135 ° C for 3 hours. After the temperature was lowered to room temperature, the solvent was distilled off under reduced pressure, and the compound of formula (3-f) was synthesized by column chromatography using a dichloromethane developing solvent. (Yield: 12.5 g 55%)
(7) [화학식 17]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by Formula 17
하기 [반응식 13]에 의하여 [화학식 17]로 표시되는 화합물을 합성하였다.A compound represented by the following formula (17) was synthesized by the following scheme (13).
[반응식 13][Reaction Scheme 13]
[화학식 17] [Chemical Formula 17]
상기 [반응식 7]로부터 얻은 [화학식 3-a]로 표시되는 화합물과 상기 [반응식 12]로부터 얻은 [화학식 3-f]를 가지고 상기 [반응식 4]의 [화학식 7]의 합성과 동일한 절차를 통하여 [화학식 17]로 표시되는 화합물을 합성하였다. (수율 4.3g 62.5%)The same procedure as in the synthesis of the compound of the formula (7) is carried out with the compound of the formula (3-a) obtained from the above-mentioned scheme 7 and the compound of the formula 3-f obtained from the above scheme A compound represented by the following formula (17) was synthesized. (Yield: 4.3 g 62.5%)
MS(MALDI-TOF): m/z 988[M]+; Anal. Calcd. MS (MALDI-TOF): m / z 988 [M] < + >; Anal. Calcd.
C50H35F4IrN6:C,60.78;H,3.57;N,8.51.Found:C,60.11;H,3.48;N,8.58.C 50 H 35 F 4 IrN 6 : C, 60.78; H, 3.57; N, 8.51; Found: C, 60.11; H, 3.48; N, 8.58.
<합성예 4> [화학식 40]으로 표시되는 화합물의 제조Synthesis Example 4 Synthesis of Compound Represented by
(1) [화학식 4-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula 4-a
하기 [반응식 14]에 의하여 [화학식 4-a]로 표시되는 화합물을 합성하였다.A compound represented by the following formula (4-a) was synthesized by the following reaction scheme (14).
[반응식 14][Reaction Scheme 14]
[화학식 4-a] [Chemical Formula 4-a]
1L 둥근 바닥 플라스크에 틸트-뷰틸-4-톨루엔 15g(0.165mol), 2,2’-아조비스메틸프로피온니트릴 13.5g(0.082mol), N-브로모수시니이미드 32.3g(0.181mol), 벤질브로마이드, 벤젠(150ml)을 넣고 5시간 동안 환류시켰다. 반응물을 0℃로 냉각한 다음 필터 및 감압증류하여 용매제거한다. 에틸아세테이트, 헥산 전개용매로 컬럼크로마토그래피를 이용하여 [화학식 4-a]을 합성하였다. (수율 25.3g 90.3%)15 g (0.165 mol) of tilter-butyl-4-toluene, 13.5 g (0.082 mol) of 2,2'-azobismethylpropionone nitrile, 32.3 g (0.181 mol) of N-bromosuccinimide, , And benzene (150 ml), and the mixture was refluxed for 5 hours. The reaction product is cooled to 0 ° C, filtered and distilled under reduced pressure to remove the solvent. [Chemical Formula 4-a] was synthesized by column chromatography using ethyl acetate and a hexane developing solvent. (Yield: 25.3 g 90.3%)
(2) [화학식 4-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 4-b
하기 [반응식 15]에 의하여 [화학식 4-b]로 표시되는 화합물을 합성하였다.[Chemical Formula 4-b] was synthesized by the following Reaction Scheme 15.
[반응식 15][Reaction Scheme 15]
[화학식 4-b] [Formula 4-b]
상기 [반응식 14]로부터 얻은 [화학식 4-a]로 표시되는 화합물을 가지고 상기 [반응식 1]의 [화학식 1-a]의 합성과 동일한 절차를 통하여 [화학식 4-b]을 합성하였다. (수율 14.1g 89.5%)[Chemical Formula 4-b] was synthesized through the same procedure as the synthesis of [Formula 1-a] in Reaction Scheme 1 with the compound represented by Chemical Formula 4-a obtained from Reaction Scheme 14 above. (Yield: 14.1 g 89.5%).
(3) [화학식 4-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 4-c
하기 [반응식 16]에 의하여 [화학식 4-c]로 표시되는 화합물을 합성하였다.[Chemical formula 4-c] was synthesized by the following reaction scheme [16].
[반응식 16][Reaction Scheme 16]
[화학식 4-c] [Chemical formula 4-c]
500ml 둥근 바닥 플라스크에 디플루오르피리딘 24.0g(0.20mol), 테트라하이드로퓨란 240ml를 넣은 후, 영하 78℃까지 냉각시켰다. 이 용액에 LDA 88.2g(0.22 mol)을 천천히 적가하고, 동일한 온도에서 2시간 교반 한 후, 요오드 63.5g(0.25 mol)을 천천히 가하였다. 상기 반응 결과물을 상온으로 승온 후, 12시간 동안 교반하였고, 이 반응물에 물(2L)을 넣고 10분간 교반한다. 에틸아세테이트로 2회 추출하고 유기층을 수분 제거 및 용매제거 한 다음 헥산으로 재결정하여 [화학식 4-c]를 합성하였다. (수율 35.8 g 69%)24.0 g (0.20 mol) of difluoropyridine and 240 ml of tetrahydrofuran were placed in a 500 ml round-bottomed flask, and then cooled to -78 ° C. To this solution, 88.2 g (0.22 mol) of LDA was slowly added dropwise, and the mixture was stirred at the same temperature for 2 hours, and then 63.5 g (0.25 mol) of iodine was slowly added thereto. The reaction product was warmed to room temperature, stirred for 12 hours, and water (2 L) was added to the reaction mixture, followed by stirring for 10 minutes. The mixture was extracted twice with ethyl acetate, and the organic layer was removed with water and the solvent was removed, and recrystallized with hexane to synthesize [Formula 4-c]. (Yield 35.8 g 69%).
(4) [화학식 4-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 4-d
하기 [반응식 17]에 의하여 [화학식 4-d]로 표시되는 화합물을 합성하였다.[Chemical formula 4-d] was synthesized by the following reaction scheme [17].
[반응식 17][Reaction Scheme 17]
[화학식 4-d] [Chemical formula 4-d]
500ml의 둥근 바닥 플라스크에 마그네슘 2.8g(0.18mol), 테트라히드로퓨란(50ml)을 넣고, 상기 [반응식 16]으로부터 얻은 [화학식 4-c]로 표시되는 화합물 30.0g(0.124mol)을 테트라히드로퓨란(240ml)에 녹인 후 천천히 적가한 다음 1시간 동안 환류시켰다. 온도를 상온으로 내린 후 반응물에 2-피리딘알데히드 12.5g (0.18mol)을 테트라히드로퓨란(100ml)에 녹여 가한 다음 10시간 동안 교반하였다. 상기 반응물을 포화 염화암모늄 수용액에 붓고 유기층을 건조 및 감압 농축한 다음 에틸아세테이트 전개용매로 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 4-d]로 표시되는 화합물을 제조하였다. (수율 18.5g 67%)(0.124 mol) of the compound represented by the formula (4-c) obtained from the above scheme [16] was placed in a 500 ml round-bottomed flask with tetrahydrofuran (240 ml), and the mixture was slowly added dropwise thereto, followed by refluxing for 1 hour. After the temperature was lowered to room temperature, 12.5 g (0.18 mol) of 2-pyridine aldehyde was dissolved in tetrahydrofuran (100 ml), and the mixture was stirred for 10 hours. The reaction product was poured into a saturated aqueous solution of ammonium chloride, and the organic layer was dried and concentrated under reduced pressure, followed by column chromatography using an ethyl acetate developing solvent. The obtained solid was dried to produce a compound represented by the following formula 4-d. (Yield: 18.5 g 67%)
(5) [화학식 4-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 4-e
하기 [반응식 18]에 의하여 [화학식 4-e]로 표시되는 화합물을 합성하였다.[Chemical Formula 4-e] was synthesized by the following Reaction Scheme 18.
[반응식 18][Reaction Scheme 18]
[화학식 4-e] [Chemical Formula 4-e]
100ml의 둥근 바닥 플라스크에 상기 [반응식 17]로부터 얻은 [화학식 4-d]로 표시되는 화합물 17.0g(0.076mol)을 메탄올(50ml), 황산(10ml)에 녹인 후 10% Pd/C(2g) 넣는다. 상온에서 수소를 넣고 수소가 소모 될 때까지 교반한 다음 촉매를 거르고 10% 수산화나트륨 수용액으로 중화 후 디클로로메탄으로 추출하여 건조 및 감압 농축한다. 에틸아세테이트 전개용매로 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 4-e]로 표시되는 화합물을 제조하였다. (수율 7.72g 49%)17.0 g (0.076 mol) of the compound represented by the formula [4-d] obtained from the above scheme [17] was dissolved in methanol (50 ml) and sulfuric acid (10 ml), and 10% Pd / C (2 g) was added to a 100 ml round bottom flask. . The mixture is stirred at room temperature until hydrogen is consumed, then the catalyst is neutralized with a 10% aqueous sodium hydroxide solution, extracted with dichloromethane, dried and concentrated under reduced pressure. The solid was separated by column chromatography with an ethyl acetate eluting solvent and dried to give the compound represented by the formula 4-e. (Yield: 7.72 g 49%)
(6) [화학식 4-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 4-f
하기 [반응식 19]에 의하여 [화학식 4-f]로 표시되는 화합물을 합성하였다.[Chemical Formula 4-f] was synthesized by the following Reaction Scheme (19).
[반응식 19][Reaction Scheme 19]
[화학식 4-f] [Chemical Formula 4-f]
상기 [반응식 18]로부터 얻은 [화학식 4-e]로 표시되는 화합물을 가지고 [반응식 3]의 [화학식 1-c]의 합성과 동일한 절차를 통하여 [화학식 4-f]을 합성하였다. (수율 14.1g 89.5%) [Chemical Formula 4-f] was synthesized through the same procedure as the synthesis of [Chemical Formula 1-c] in [Reaction Scheme 3] with the compound represented by Chemical Formula 4-e obtained from the above Scheme 18. (Yield: 14.1 g 89.5%).
(7) [화학식 40]으로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by
하기 [반응식 20]에 의하여 [화학식 40]으로 표시되는 화합물을 합성하였다.A compound represented by the formula (40) was synthesized by the following reaction scheme (20).
[반응식 20][Reaction Scheme 20]
[화학식 40] (40)
상기 [반응식 15]으로부터 얻은 [화학식 4-b]로 표시되는 화합물과 상기 [반응식 19]로부터 얻은 [화학식 4-f]을 가지고 상기 [반응식 4]의 [화학식 7] 합성과 동일한 절차를 통하여 [화학식 40]으로 표시되는 화합물을 합성하였다. (수율 3.1g 53%)The compound of the formula [4-b] is obtained from the compound of the formula [4-b] and the compound of the formula [4-f] The compound represented by the formula (40) was synthesized. (Yield: 3.1 g 53%)
MS(MALDI-TOF): m/z 736[M]+; Anal. Calcd. MS (MALDI-TOF): m / z 736 [M] < + >; Anal. Calcd.
C31H25F4IrN5:C,50.60;H,3.42;N,9.52.Found:C,49.99.11;H,3.38;N,9.51.C 31 H 25 F 4 IrN 5 : C, 50.60; H, 3.42; N, 9.52; Found: C, 49.99.11, H, 3.38, N, 9.51.
<합성예 5> [화학식 75]로 표시되는 화합물의 제조≪ Synthesis Example 5 > Preparation of a compound represented by the formula (75)
(1) [화학식 5-a]로 표시되는 화합물의 합성(1) Synthesis of a compound represented by the formula (5-a)
하기 [반응식 21]에 의하여 [화학식 5-a]로 표시되는 화합물을 합성하였다.A compound represented by the formula (5-a) was synthesized by the following Reaction Scheme (21).
[반응식 21][Reaction Scheme 21]
[화학식 5-a] [Formula 5-a]
상기 [반응식 1]의 [화학식 1-a] 합석과 동일한 절차를 통하여 [화학식 5-a]을 합성하였다. (수율 15.0g 91.5%)[Chemical Formula 5-a] was synthesized through the same procedure as in [Formula 1-a] in Reaction Scheme 1 above. (Yield: 15.0 g, 91.5%).
(2) [화학식 5-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 5-b
하기 [반응식 22]에 의하여 [화학식 5-b]로 표시되는 화합물을 합성하였다.[Chemical Formula 5-b] was synthesized by the following Reaction Formula 22.
[반응식 22][Reaction Scheme 22]
[화학식 5-b] [Chemical Formula 5-b]
100ml의 둥근 바닥 플라스크에 포름산(40ml)을 넣고 0℃ 이하에서 2-브로모-5-아미노피린딘 23.4g(0.135mol)을 천천히 가한 후 포름알데히드 34ml (0.420mol)을 가한 다음 2시간 동안 환류시킨다. 온도를 상온으로 내린다음 1N KOH(200ml) 수용액에 붓고 에테르로 추출 후 감압 농축한다. 디클로로메탄 전개용매로 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 5-b]로 표시되는 화합물을 제조하였다. (수율 10.4g 40%).Formic acid (40 ml) was added to a 100 ml round-bottomed flask, and 23.4 g (0.135 mol) of 2-bromo-5-aminopyridine was slowly added thereto at 0 ° C. or lower. 34 ml (0.420 mol) of formaldehyde was added thereto and refluxed for 2 hours . The temperature was lowered to room temperature, poured into 1N KOH (200 ml) aqueous solution, extracted with ether, and concentrated under reduced pressure. The solid was separated by column chromatography using a developing solvent of dichloromethane and then dried to obtain the compound represented by the formula 5-b. (Yield 10.4
(3) [화학식 5-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 5-c
하기 [반응식 23]에 의하여 [화학식 5-c]로 표시되는 화합물을 합성하였다.[Chemical Formula 5-c] was synthesized by the following Reaction Formula 23.
[반응식 23][Reaction Scheme 23]
[화학식 5-c] [Chemical Formula 5-c]
250ml 둥근 바닥 플라스크에 상기 [반응식 22]로부터 얻은 [화학식 5-b]로 표시되는 화합물 10.0g(0.049mol), 테트라하이드로퓨란 100ml를 투입한 후 -78℃에서 1.6M 노르말 뷰틸리튬 24.5g(0.060mol)을 천천히 적가한 다음 1시간 동안 교반하였다. 동일한 온도에서 N,N-디메틸포름아마이드 4.4g(0.060mol)를 적가해 준 후 상온에서 8시간 교반하였다. 물과 에틸아세테이트 이용하여 유기층을 분리하고 감압 농축한 후 헥산과 에틸아세테이트를 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 [화학식 5-c]로 표시되는 화합물을 얻었다. (수율 5.1g 69.3%)10.0 g (0.049 mol) of the compound represented by the above formula [5-b] and 100 ml of tetrahydrofuran were charged into a 250 ml round-bottomed flask, and then 24.5 g (0.060 mol) was slowly added dropwise thereto, followed by stirring for 1 hour. 4.4 g (0.060 mol) of N, N-dimethylformamide was added dropwise at the same temperature, followed by stirring at room temperature for 8 hours. The organic layer was separated using water and ethyl acetate, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent to obtain the compound represented by Formula 5-c. (Yield 5.1 g 69.3%)
(4) [화학식 5-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 5-d
하기 [반응식 24]에 의하여 [화학식 5-d]로 표시되는 화합물을 합성하였다.[Chemical Formula 5-d] was synthesized by the following Reaction Scheme 24.
[반응식 24][Reaction Scheme 24]
[화학식 5-d] [Chemical formula 5-d]
상기 [반응식 16]으로부터 얻은 [화학식 4-c]로 표시되는 화합물과 상기 [반응식 23]으로부터 얻은 [화학식 5-c]를 가지고 [반응식 17]의 [화학식 4-d] 합성과 동일한 절차를 통하여 [화학식 5-d]로 표시되는 화합물을 제조하였다. (수율 18.6g 56.8%)The same procedure as in the synthesis of [Formula 4-d] of [Reaction Scheme 17] with the compound of Formula 4-c] obtained from the above-mentioned Reaction Formula 16 and the Formula 5-c obtained from the above Reaction Formula 23 was carried out [Chemical formula 5-d] was prepared. (Yield: 18.6 g 56.8%)
(5) [화학식 5-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 5-e
하기 [반응식 25]에 의하여 [화학식 5-e]로 표시되는 화합물을 합성하였다.[Chemical Formula 5-e] was synthesized according to Reaction Scheme 25 below.
[반응식 25][Reaction Scheme 25]
[화학식 5-e] [Chemical Formula 5-e]
상기 [반응식 24]로부터 얻은 [화학식 5-d]로 표시되는 화합물을 가지고 상기 [반응식 18]의 [화학식 4-e] 합성과 동일한 절차를 통하여 [화학식 5-e]로 표시되는 화합물을 제조하였다. (수율 7.9g 56.3%)The compound represented by the formula 5-e was prepared by the same procedure as the synthesis of the compound of the formula 4-e in the reaction scheme 18 with the compound of the formula 5-d obtained from the above scheme 24 . (Yield: 7.9 g 56.3%)
(6) [화학식 5-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 5-f
하기 [반응식 26]에 의하여 [화학식 5-f]로 표시되는 화합물을 합성하였다.[Chemical Formula 5-f] was synthesized by the following Reaction Formula 26.
[반응식 26][Reaction Scheme 26]
[화학식 5-f] [Chemical Formula 5-f]
상기 [반응식 25]로부터 얻은 [화학식 5-e]로 표시되는 화합물을 이용하여 [반응식 3]의 [화학식 1-c] 합성과 동일한 절차를 통하여 [화학식 5-f]로 표시되는 화합물을 합성하였다. (수율 7.4g 85.3%)The compound represented by the formula 5-f was synthesized through the same procedure as the synthesis of the formula 1-c in the
(7) [화학식 75]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by Formula 75
하기 [반응식 27]에 의하여 [화학식 75]로 표시되는 화합물을 합성하였다.A compound represented by the formula (75) was synthesized by the following scheme (27).
[반응식 27][Reaction Scheme 27]
[화학식 75] (75)
상기 [반응식 26]으로부터 얻은 [화학식 5-f]로 표시되는 화합물과 상기 [반응식 21]로부터 얻은 [화학식 5-a]를 가지고 상기 [반응식 4]의 [화학식 7] 합성과 동일한 절차를 통하여 [화학식 75]로 표시되는 화합물을 합성하였다. (수율 1.9g 45.8%)(5-a) obtained from the above-mentioned Reaction Formula 21 and the compound represented by the above formula [5-f] obtained from the above-mentioned Reaction Formula 26 and the above- A compound represented by the formula (75) was synthesized. (Yield: 1.9 g 45.8%)
MS(MALDI-TOF): m/z 853[M]+; Anal. Calcd. MS (MALDI-TOF): m / z 853 [M] < + >; Anal. Calcd.
C36H38F4IrN7O:C,50.69;H,4.49;N,11.50.Found:C,50.18.11;H,4.40;N,11.48.C 36 H 38 F 4 IrN 7 O: C, 50.69; H, 4.49; N, 11.50.
<합성예 6> [화학식 199]로 표시되는 화합물의 제조≪ Synthesis Example 6 > Preparation of a compound represented by the formula [199]
(1) [화학식 6-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by Formula (6-a)
하기 [반응식 28]에 의하여 [화학식 6-a]로 표시되는 화합물을 합성하였다.A compound represented by the general formula [6-a] was synthesized by the following reaction scheme.
[반응식 28][Reaction Scheme 28]
[화학식 6-a] [Chemical Formula 6-a]
상기 [반응식 1]의 [화학식 1-a] 합성과 동일한 절차를 통하여 [화학식 6-a]를 합성하였다. (수율 13.6g 83.6%)[Formula 6-a] was synthesized through the same procedure as the synthesis of [Formula 1-a] in [Reaction Scheme 1]. (Yield: 13.6 g, 83.6%)
(2) [화학식 6-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 6-b
하기 [반응식 29]에 의하여 [화학식 6-b]로 표시되는 화합물을 합성하였다.[Chemical Formula 6-b] was synthesized by the following Reaction Scheme 29.
[반응식 29][Reaction Scheme 29]
[화학식 6-b] [Chemical Formula 6-b]
250ml 둥근 바닥 플라스크에 1-브로모-2,6-플로로벤젠 20.0g(0.105mol), 1,3-디브로모-5,5-디메틸히단토인 17.8g(0.062mol), 디클로로메탄을 넣고 교반한 후 트리플로로메탄슬폰산 18.7g(0.124mol)을 가한 다음 상온에서 5시간 동안 교반하였다. 탄산나트륨 수용액으로 중화한 다음 건조 및 감압증류로 용매 제거 후 헥산 전개용매로 컬럼크로마토그래피를 사용하여 [화학식 6-b]로 표시되는 화합물을 합성하였다. (수율 26.4g 92.5%)20.0 g (0.105 mol) of 1-bromo-2,6-fluorobenzene, 17.8 g (0.062 mol) of 1,3-dibromo-5,5-dimethylhydantoin and dichloromethane were placed in a 250 ml round bottom flask After stirring, 18.7 g (0.124 mol) of trifluoromethane sulfonic acid was added, followed by stirring at room temperature for 5 hours. After neutralization with an aqueous solution of sodium carbonate, the solvent was removed by drying and distillation under reduced pressure, and then the product was purified by column chromatography using a hexane-developing solvent to synthesize a compound represented by the formula 6-b. (Yield: 26.4 g 92.5%)
(3) [화학식 6-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula 6-c
하기 [반응식 30]에 의하여 [화학식 6-c]로 표시되는 화합물을 합성하였다.[Chemical Formula 6-c] was synthesized by the following
[반응식 30][Reaction Scheme 30]
[화학식 6-c] [Chemical formula 6-c]
1L의 둥근 바닥 플라스크에 상기 [반응식 29]로부터 얻은 [화학식 6-b]로 표시되는 화합물 25.0g(0.092mol), 4-메톡시피리딘보레이트 25.9g(0.110mol), 테트라키스트리페닐포스핀팔라듐 2.1g(0.002mol), 탄산칼륨 24.3g(0.184mol), THF (500ml), 물(250ml)를 넣고 12시간 동안 환류시켰다. 상기 용액을 상온으로 냉각하고 유기층을 분리하여 감압농축한 후, 헥산과 에틸아세테이트를 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 6-c]로 표시되는 화합물을 제조하였다. (수율 20.4g 74%)25.0 g (0.092 mol) of the compound represented by the formula (6-b), 25.9 g (0.110 mol) of 4-methoxypyridine borate, 0.19 mol of tetrakistriphenylphosphine palladium (0.002 mol), potassium carbonate (24.3 g, 0.184 mol), THF (500 ml) and water (250 ml), and the mixture was refluxed for 12 hours. The solution was cooled to room temperature, and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent to obtain a solid, which was dried to produce a compound represented by the formula 6-c . (Yield: 20.4 g 74%)
(4) [화학식 6-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by Formula 6-d
하기 [반응식 31]에 의하여 [화학식 6-d]로 표시되는 화합물을 합성하였다.[Chemical Formula 6-d] was synthesized by the following Reaction Formula 31.
[반응식 31][Reaction Scheme 31]
[화학식 6-d] [Chemical formula 6-d]
500ml의 둥근 바닥 플라스크에 상기 [반응식 30]으로부터 얻은 [화학식 6-c]로 표시되는 화합물 20.0g(0.067mol), 자이렌보론산 12.0g(0.080mol), 테트라키스트리페닐포스핀팔라듐 1.5g(0.001mol), 탄산칼륨 17.7g(0.134mol), THF(400 ml), 물(200ml)를 넣고 12시간 동안 환류시켰다. 상기 용액을 상온으로 냉각하고 유기층을 분리하여 감압농축한 후, 헥산과 에틸아세테이트를 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 6-d]로 표시되는 화합물을 제조하였다. (수율 18.5g 85.2%)20.0 g (0.067 mol) of the compound represented by the above formula [6-c], 12.0 g (0.080 mol) of zeyleneboronic acid and 1.5 g of tetrakistriphenylphosphine palladium 17.7 g (0.134 mol) of potassium carbonate, 400 ml of THF and 200 ml of water were added, and the mixture was refluxed for 12 hours. The solution was cooled to room temperature and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent to obtain a solid, which was dried to produce a compound represented by the formula 6-d . (Yield: 18.5 g 85.2%)
(5) [화학식 6-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by Formula 6-e
하기 [반응식 32]에 의하여 [화학식 6-e]로 표시되는 화합물을 합성하였다.The compound represented by the formula 6-e is synthesized by the following reaction scheme [32].
[반응식 32][Reaction Scheme 32]
[화학식 6-e] [Chemical Formula 6-e]
상기 [반응식 31]로부터 얻은 [화학식 6-d]로 표시되는 화합물을 이용하여 상기 [반응식 3]의 [화학식 1-c] 합성과 동일한 절차를 통하여 [화학식 6-e]로 표시되는 화합물을 합성하였다. (수율 10.6g 65.9%)Compound [6-e] was synthesized through the same procedure as the synthesis of [Formula 1-c] in the
(6) [화학식 199]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula (199)
하기 [반응식 33]에 의하여 [화학식 199]로 표시되는 화합물을 합성하였다.A compound represented by the formula (199) was synthesized by the following reaction scheme [33].
[반응식 33][Reaction Scheme 33]
[화학식 199] [199]
상기 [반응식 32]로부터 얻은 [화학식 6-e]로 표시되는 화합물과 상기 [반응식 28]로부터 얻은 [화학식 6-a]를 가지고 [반응식 4]의 [화학식 7] 합성과 동일한 절차를 통하여 [화학식 199]로 표시되는 화합물을 합성하였다. (수율 1.9g 45.8%)A compound of the formula [6-a] obtained from the above-mentioned [Reaction formula 32] and a compound of the formula [6-a] obtained from the above-mentioned Reaction scheme [28] 199] was synthesized. (Yield: 1.9 g 45.8%)
MS(MALDI-TOF): m/z 1000[M]+; Anal. Calcd. MS (MALDI-TOF): m / z 1000 [M] < + >; Anal. Calcd.
C50H43F4IrN4O2:C,60.05;H,4.33;N,5.60.Found:C,59.89;H,4.27;N,5.63.C 50 H 43 F 4 IrN 4 O 2 : C, 60.05; H, 4.33; N, 5.60.Found: C, 59.89; H, 4.27; N, 5.63.
<실시예 1 내지 6> 유기전계발광소자의 제조>≪ Examples 1 to 6 > Preparation of Organic Electroluminescent Device >
ITO 글래스의 발광 면적이 2mm×2mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1×10-6torr가 되도록 한 후 유기물을 상기 ITO위에 DNTPD(700Å), NPD(300Å), mCP + 본 발명에 의해 제조된 화합물(10%)(300Å), Alq3(350Å), LiF(5Å), Al(1,000Å)의 순서로 성막하였으며, 0.4mA에서 측정을 하였다.The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 -6 torr. Then, an organic material was injected onto the ITO using DNTPD (700 Å), NPD (300 Å), mCP + 300 Å), Alq 3 (350 Å), LiF (5 Å), and Al (1,000 Å).
[DNTPD][DNTPD]
[NPD][NPD]
[mCP][mCP]
[Alq3][Alq 3 ]
<비교예 1>≪ Comparative Example 1 &
비교예를 위한 유기전계발광소자는 상기 실시예 1 내지 6의 소자 구조에서 본 발명에 의해 제조된 유기 금속 화합물 대신 하기 청색 인광 도펀트 물질로서 FIrpic을 사용한 점을 제외하고 동일하게 제작하였다.The organic electroluminescent device for the comparative example was fabricated in the same manner as in Example 1 except that FIrpic was used as the blue phosphorescent dopant instead of the organometallic compound prepared according to the present invention.
[FIrpic][FIrpic]
상기 <실시예 1 내지 6>, <비교예 1> 및 [표 1]에서 보는 바와 같이 본 발명에 의하여 확보된 유기화합물은 인광발광재료로 많이 쓰이는 FIrpic에 비하여 외부양자 효율이 우수한 특성을 보이므로 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.As shown in Examples 1 to 6, Comparative Example 1 and Table 1, the organic compound obtained according to the present invention exhibits excellent external quantum efficiency as compared with FIrpic, which is widely used as a phosphorescent light emitting material Display elements, display elements, illumination, and the like.
Claims (10)
[화학식 1]
상기 [화학식 1]에서,
Ar1 및 Ar3는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 40의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴기이고,
Ar2는 적어도 하나의 질소 원자를 포함하는 치환 또는 비치환된 탄소수 3 내지 40의 헤테로아릴기이며,
R은 수소원자, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 탄소수 6 내지 20의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기로 이루어진 군으로부터 선택되고,
L은 단결합 또는 치환 또는 비치환된 탄소수 1 내지 4의 알킬렌이고,
n은 1 또는 2이고,
상기
[LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6]
[LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13]
[LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20]
[LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27]
[LS 28] [LS 29] [LS 30] [LS 31] [LS 32]
[Chemical Formula 1]
In the above formula (1)
Ar 1 and Ar 3 each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
Ar 2 is a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms containing at least one nitrogen atom,
R is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,
n is 1 or 2,
remind
[LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6]
[LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13]
[LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20]
[LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27]
[LS 28] [LS 29] [LS 30] [LS 31] [LS 32]
상기
[LS 33] [LS 34] [LS 35] [LS 36] [LS 37]
[LS 38] [LS 39] [LS 40] [LS 41] [LS 42]
remind
[LS 33] [LS 34] [LS 35] [LS 36] [LS 37]
[LS 38] [LS 39] [LS 40] [LS 41] [LS 42]
하기 [화학식 7] 내지 [화학식 214]로 표시되는 군으로부터 선택된 어느 하나의 화합물인 것을 특징으로 하는 유기금속 화합물:
[화학식 7] [화학식 8] [화학식 9] [화학식 10]
[화학식 11] [화학식 12] [화학식 13] [화학식 14]
[화학식 15] [화학식 16] [화학식 17] [화학식 18]
[화학식 19] [화학식 20] [화학식 21] [화학식 22]
[화학식 23] [화학식 24] [화학식 25] [화학식 26]
[화학식 27] [화학식 28] [화학식 29] [화학식 30]
[화학식 31] [화학식 32] [화학식 33] [화학식 34]
[화학식 35] [화학식 36] [화학식 37] [화학식 38]
[화학식 39] [화학식 40] [화학식 41] [화학식 42]
[화학식 43] [화학식 44] [화학식 45] [화학식 46]
[화학식 47] [화학식 48] [화학식 49] [화학식 50]
[화학식 51] [화학식 52] [화학식 53] [화학식 54]
[화학식 55] [화학식 56] [화학식 57] [화학식 58]
[화학식 59] [화학식 60] [화학식 61] [화학식 62]
[화학식 63] [화학식 64] [화학식 65] [화학식 66]
[화학식 67] [화학식 68] [화학식 69] [화학식 70]
[화학식 71] [화학식 72] [화학식 73] [화학식 74]
[화학식 75] [화학식 76] [화학식 77] [화학식 78]
[화학식 79] [화학식 80] [화학식 81] [화학식 82]
[화학식 83] [화학식 84] [화학식 85] [화학식 86]
[화학식 87] [화학식 88] [화학식 89] [화학식 90]
[화학식 91] [화학식 92] [화학식 93] [화학식 94]
[화학식 95] [화학식 96] [화학식 97] [화학식 98]
[화학식 99] [화학식 100] [화학식 101] [화학식 102]
[화학식 103] [화학식 104] [화학식 105] [화학식 106]
[화학식 107] [화학식 108] [화학식 109] [화학식 110]
[화학식 111] [화학식 112] [화학식 113] [화학식 114]
[화학식 115] [화학식 116] [화학식 117] [화학식 118]
[화학식 119] [화학식 120] [화학식 121] [화학식 122]
[화학식 123] [화학식 124] [화학식 125] [화학식 126]
[화학식 127] [화학식 128] [화학식 129] [화학식 130]
[화학식 131] [화학식 132] [화학식 133] [화학식 134]
[화학식 135] [화학식 136] [화학식 137] [화학식 138]
[화학식 139] [화학식 140] [화학식 141] [화학식 142]
[화학식 143] [화학식 144] [화학식 145] [화학식 146]
[화학식 147] [화학식 148] [화학식 149] [화학식 150]
[화학식 151] [화학식 152] [화학식 153] [화학식 154]
[화학식 155] [화학식 156] [화학식 157] [화학식 158]
[화학식 159] [화학식 160] [화학식 161] [화학식 162]
[화학식 163] [화학식 164] [화학식 165] [화학식 166]
[화학식 167] [화학식 168] [화학식 169] [화학식 170]
[화학식 171] [화학식 172] [화학식 173] [화학식 174]
[화학식 175] [화학식 176] [화학식 177] [화학식 178]
[화학식 179] [화학식 180] [화학식 181] [화학식 182]
[화학식 183] [화학식 184] [화학식 185] [화학식 186]
[화학식 187] [화학식 188] [화학식 189] [화학식 190]
[화학식 191] [화학식 192] [화학식 193] [화학식 194]
[화학식 195] [화학식 196] [화학식 197] [화학식 198]
[화학식 199] [화학식 200] [화학식 201] [화학식 202]
[화학식 203] [화학식 204] [화학식 205] [화학식 206]
[화학식 207] [화학식 208] [화학식 209] [화학식 210]
[화학식 211] [화학식 212] [화학식 213] [화학식 214]
Is an organic metal compound represented by any one of the following formulas (7) to (214):
[Chemical Formula 8] < EMI ID =
[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]
[Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]
[Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]
[Chemical Formula 25] [Chemical Formula 25]
[Chemical Formula 30] [Chemical Formula 30]
[Chemical Formula 32] [Chemical Formula 32]
[Chemical Formula 35] [Chemical Formula 35]
[Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]
[Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 45]
[Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]
[Chemical Formula 51]
[Chemical Formula 55] [Chemical Formula 55]
[Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62]
[Chemical Formula 65] [Chemical Formula 65]
[Chemical Formula 70] [Chemical Formula 70]
[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74]
[Formula 75] < EMI ID = 78.1 >
[Formula 80] [Formula 81] [Formula 82]
[Formula 83] [Formula 85] [Formula 86]
[Formula 90] [Formula 90] [Formula 90]
[Chemical Formula 91] [Chemical Formula 93] [Chemical Formula 94]
[Chemical Formula 97] [Chemical Formula 97] [Chemical Formula 98]
[Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 101]
[Formula 103] [Formula 105] [Formula 106]
[Formula 110] [Formula 110] [Formula 110]
[Formula 111] [Formula 113] [Formula 114]
[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118]
[Chemical Formula 120]
[Formula 124] [Formula 125] [Formula 126]
[Formula 127] < EMI ID = 129.0 >
[Formula 131] [Formula 133] [Formula 134]
[Chemical Formula 135] [Chemical Formula 135]
[Formula 140] [Formula 141] [Formula 142]
[Chemical Formula 144] [Chemical Formula 145] [Chemical Formula 146]
[Formula 150] [Formula 149] [Formula 150]
[Formula 154] [Formula 154] [Formula 154]
[Formula 157] < EMI ID = 158.1 >
[Formula 161] [Formula 161] [Formula 161]
[Formula 166] [Formula 166] [Formula 166]
[Formula 16] [Formula 16]
[Formula 173] [Formula 174] [Formula 174]
[Formula 177] [Formula 177] [Formula 178]
[Formula 181] [Formula 181] [Formula 182]
[Formula 184] [Formula 184] [Formula 186] [Formula 186]
[Formula 188] [Chemical Formula 189] [Chemical Formula 190]
[193] [193] [193] [194]
[197] [198] [198] [198] [198]
[Chemical Formula 200] [Chemical Formula 201] [Chemical Formula 202]
[Chemical Formula 203]
[Chemical Formula 20] [Chemical Formula 20] [Chemical Formula 20]
[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214]
캐소드; 및
상기 애노드 및 캐소드 사이에 개재되며, 상기 제 1 항에 따른 유기금속 화합물을 포함하는 층을 구비한 유기전계발광소자.Anode;
Cathode; And
And an organic metal compound layer interposed between the anode and the cathode.
상기 유기금속 화합물이 함유된 층은 상기 애노드 및 캐소드 사이의 발광층인 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the layer containing the organic metal compound is a light emitting layer between the anode and the cathode.
상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.8. The method of claim 7,
And at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode.
상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자.9. The method of claim 8,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process.
상기 유기전계발광소자는 표시소자, 디스플레이 소자, 또는 단색 또는 백색 조명용 소자에 사용되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.
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| US10253252B2 (en) | 2014-12-30 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
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