KR101753741B1 - Iridium complex compounds and organic electroluminescent device using the same - Google Patents
Iridium complex compounds and organic electroluminescent device using the same Download PDFInfo
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- KR101753741B1 KR101753741B1 KR1020150068727A KR20150068727A KR101753741B1 KR 101753741 B1 KR101753741 B1 KR 101753741B1 KR 1020150068727 A KR1020150068727 A KR 1020150068727A KR 20150068727 A KR20150068727 A KR 20150068727A KR 101753741 B1 KR101753741 B1 KR 101753741B1
- Authority
- KR
- South Korea
- Prior art keywords
- organic electroluminescent
- layer
- electroluminescent device
- iridium complex
- organic
- Prior art date
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 53
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000010410 layer Substances 0.000 claims description 123
- 239000000463 material Substances 0.000 claims description 49
- 239000002019 doping agent Substances 0.000 claims description 29
- 239000011368 organic material Substances 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 8
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- PLVCYMZAEQRYHJ-UHFFFAOYSA-N (2-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Br PLVCYMZAEQRYHJ-UHFFFAOYSA-N 0.000 claims description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000002184 metal Substances 0.000 abstract description 9
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 229940125904 compound 1 Drugs 0.000 description 17
- 238000004020 luminiscence type Methods 0.000 description 13
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 8
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000005283 ground state Effects 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ODISAUHBLBVQKC-UHFFFAOYSA-N 2-bromo-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(Br)=C1 ODISAUHBLBVQKC-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- OPZDXMCOWFPQPE-UHFFFAOYSA-N 2-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(Br)=C1 OPZDXMCOWFPQPE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
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- 239000012535 impurity Substances 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 229930192474 thiophene Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- -1 oligothiophene Chemical class 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 description 1
- BHJGTYRAZMRDIZ-UHFFFAOYSA-N 1-(2-benzylphenyl)-2-phenylethane-1,2-dione Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1CC1=CC=CC=C1 BHJGTYRAZMRDIZ-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
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- GOEKEBMHTSTKOX-UHFFFAOYSA-N C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 GOEKEBMHTSTKOX-UHFFFAOYSA-N 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H01L51/50—
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to an iridium complex and an organic electroluminescent device using the iridium complex. More particularly, the present invention relates to a novel compound which is a complex having iridium (III) as a central metal, A luminescent property, a luminescent efficiency and a lifetime, a method for efficiently synthesizing an iridium complex compound capable of realizing a low driving voltage, and an organic electroluminescent device using the iridium complex.
Description
The present invention relates to an iridium complex and an organic electroluminescent device using the iridium complex. More particularly, the present invention relates to a novel compound which is a complex having iridium (III) as a central metal, A luminescent property, a luminescent efficiency and a lifetime, a method for efficiently synthesizing an iridium complex compound capable of realizing a low driving voltage, and an organic electroluminescent device using the iridium complex.
Organic light-emitting diodes (OLEDs) are displays using organic materials that emit themselves. More specifically, when an electric field is applied to an organic electroluminescent device, electrons and holes are transmitted from the cathode and the anode to each other and are coupled in the organic material, and the generated energy is emitted as light. . Organic electroluminescent devices have lower power consumption than LCDs, have a better viewing angle and have a significantly improved response speed, and are able to process high-quality images.
The phenomenon in which an organic electroluminescent device emits light can be roughly classified into fluorescence and phosphorescence. Fluorescence is a phenomenon in which organic molecules emit light when they fall from a singlet excited state to a ground state. Phosphorescence is a phenomenon in which organic molecules emit light when they fall from a triplet excited state to a ground state.
The organic compound doped in the organic electroluminescent device including the light emitting layer forms a molecule through a covalent bond of electrons between carbon and another carbon, or between carbon and another atom. In this molecular electron orbit, two pairs of electron orbits in the atomic state participate to form a bonding orbit (Bonding Molecular Orbital) and an antibonding molecular orbital respectively. At this time, the band formed by many coupling orbits is called a valence band, and a band formed by many semi-coupling orbits is called a conduction band. The highest energy level of a valence band is called a HOMO (Lowest Unoccupied Molecular Orbital), and the energy difference between the HOMO energy and the LUMO is called a band gap (Band Gap).
Electrons and holes injected into the LUMO and HOMO of the organic light emitting layer constituting the organic electroluminescent device are recombined to form an exciton. The electric energy of the exciton is converted into light energy, Thereby realizing light of a color corresponding to the energy bandgap. In this process, a singlet exciton with a total spin of 0 and a triplet exciton with a spin quantum sum of 1 are produced at a ratio of about 1: 3. At this time, the selection rule for the electronic dipole moment transition, that is, the transition process in which the spin quantum number is changed when transitioning from the excited state to the ground state becomes a very difficult process. Since the bottom state of the organic molecules is a singlet state, single excitons emit light and can efficiently emit fluorescence by making a transition to a bottom state. However, since triplet excitons need to change the spin quantum number, Can not. Therefore, in general, the maximum internal quantum efficiency is limited to 25% in the case of an organic electroluminescent device in which a fluorescent dye is used as a light emitting layer or doped in a light emitting layer.
On the other hand, if the spin-orbital coupling can be greatly increased, the mixing of singlet and triplet states is increased and the efficiency of inter-system crossing between single-and triplet states is greatly increased In addition, triplet excitons can undergo phosphorescence under transient conditions. As a result, if the triplet exciton can be utilized to emit light, the internal quantum efficiency of the organic electroluminescent device can be theoretically improved to 100%.
The organic electroluminescent device for phosphorescence capable of dramatically improving the luminous efficiency of the organic electroluminescent device is disclosed in S. R. Prof. Forrest and M.E. In particular, the spin-orbit coupling is proportional to the fourth power of the atomic number, so it is a heavy atom complex such as platinum (Pt), iridium (Ir), europium (Eu), terbium It is known that the phosphorescence efficiency is high. In the case of the platinum complex, the lowest triplet exciton is a ligand-centered exciton (LC exciton) centered at the ligand, but the iridium complex has the lowest energy triplet exciton in the charge transfer state between the central metal and the ligand charge transfer, MLCT). Therefore, the iridium complex forms a larger spin-orbital bond as compared with the platinum complex, and exhibits a higher phosphorescence efficiency with a shorter triplet exciton lifetime.
In this regard, C. Adachi et al. Reported that a green phosphorescent pigment with iridium as a central metal, bis (2-phenylpyridine) iridium (Ⅲ) acetylacetonate [(ppy) ) -5-phenyl-1,2,4-triazole (TAZ) to obtain a maximum luminous efficiency of 60 lm / W and a maximum internal quantum efficiency of 87%. In addition, US Universal Display Corp. (UDC) has announced that it has achieved high luminous efficiency of 82 lm / W by doping such a green phosphorescent pigment into a light emitting layer and using a hole injecting material developed by domestic LG Chemical.
Organic electroluminescent devices for phosphorescence exhibiting blue, green and red colors have been developed, but organic electroluminescent devices for phosphorescence of three primary colors, which are excellent in luminous efficiency, color coordinates and lifetime characteristics, have not been developed sufficiently. For example, recently, it has been reported that Ir (btp) 2 (acac), which is a phosphorescent material that emits blue light, and Ir (btp) 2 (acac), which emits red luminescent color, (Acetylacetonate) has been developed, but it has not yet reached satisfactory levels in terms of color purity, efficiency and solubility, and needs to be improved. It is a situation.
In particular, iridium complexes vary greatly in the degree of hue (e.g., blue) to be realized even with slight structural differences. A conventional iridium complex phosphorescent dopant having a substituent introduced into only one side of the mother nucleus has a desired level of dark color (e.g., ) Could not be implemented.
DISCLOSURE Technical Problem Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and it is an object of the present invention to provide an organic electroluminescent device having a novel structure capable of realizing a higher luminous efficiency, And an iridium complex compound.
In order to achieve the above technical object, the present invention provides an iridium complex having a specific structure in which iridium (III) is a center metal complex, and the same substituent is introduced to both of the imidazole moieties.
Also, the iridium complex is used as an organic material layer of an organic electroluminescent device.
Specifically, the iridium complex is used as an emission layer material of an organic electroluminescent device.
More specifically, the iridium complex is used as a dopant material of an organic electroluminescent light emitting layer.
According to another aspect of the present invention, there is provided a process for efficiently and economically synthesizing the iridium complex.
According to still another aspect of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and at least one organic material layer disposed between the electrodes, wherein the at least one organic material layer includes a light emitting layer, An organic electroluminescent device comprising the iridium complex according to the present invention.
Specifically, the organic electroluminescent device is characterized in that the host material is doped with the iridium complex.
In addition, the at least one organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
When the iridium complex according to the present invention is used as a light emitting layer material (in particular, a dopant) of an organic electroluminescent device, excellent color purity can be realized in addition to high luminous efficiency, luminance characteristics, lifetime characteristics and low driving voltage of the device.
Specifically, the iridium complex according to the present invention is a phosphorescent dopant that facilitates energy transfer. When an organic thin film layer containing a conjugated polymer having fluorescent electroluminescence characteristics and a novel iridium complex phosphorescent dopant of the present invention is provided, The red, blue, and green luminescence can be efficiently displayed.
Also, according to the production method of the present invention, the iridium complex can be efficiently and economically synthesized through an easy process.
1 is a schematic view illustrating a single layer structure of an organic electroluminescent device according to an embodiment of the present invention.
FIG. 2 is a schematic view illustrating a multiple layer structure of an organic electroluminescent device according to another embodiment of the present invention. Referring to FIG.
3 is a graph showing UV (Ultraviolet) spectrum of Compound 1 prepared according to the present invention.
4 is a graph showing PL (Photoluminescence) spectrum of Compound 1 prepared according to the present invention.
5 is a graph showing PL measurement data on a conventional iridium complex having a substituent introduced into only one side thereof.
6 to 8 are graphs showing PL measurement data on iridium complexes having substituents introduced on both sides according to the present invention.
Hereinafter, the present invention will be described in detail.
Iridium complex
The iridium complex according to the present invention is represented by the following general formula (I).
(I)
In the formula (I)
Ar 1 is each independently selected from the group consisting of C1 to C20 alkyl (for example, C1 to C5 alkyl), C1 to C20 alkoxy (for example, C1 to C5 alkoxy), C6 to C30 aryl, A C1 to C20 haloalkyl group such as a C1 to C5 haloalkyl group, a halogen atom, a trifluoromethyl group, a cyano group, a phenyl group, a carbazole group, a thiophene group, a benzothiazole group, ≪ / RTI > unsubstituted or substituted with one or more of < RTI ID = 0.0 >
At least one of a hydrogen atom, a C1 to C20 alkyl (e.g., C1 to C5 alkyl), a C1 to C20 alkoxy (e.g., C1 to C5 alkoxy), a C6 to C30 aryl, N, O, A heterocyclic group of C5 to C30 which is substituted by at least one substituent selected from the group consisting of halogen, phenyl, naphthyl, anthracenyl, pyridine, pyrazine, pyrazole, imidazole, triazine, carbazole, quinoxaline, thiazole, fluorenyl, thiophene, As furan, benzofuran, dibenzofurane, or fluorine,
Each Ar < 1 > may form a mutual condensation ring.
Ar 2 is a hydrogen atom, a C 1 to C 20 alkoxy (e.g., methoxy) or a halogen (e.g., fluorine).
Specifically, the iridium complex according to the present invention is selected from the group of compounds represented by the following structural formulas, and they can be suitably used as an organic material layer material of an organic electroluminescent device.
Here, the organic material layer of the organic electroluminescent device may include at least one of an electroluminescence layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, And an electron injection layer (electron injection layer).
In particular, the iridium complex according to the present invention exhibits excellent luminescence characteristics and is used as a dopant of a light emitting layer material of an organic electroluminescent device, particularly a dopant material of an organic electroluminescent device, to efficiently form red, blue (in particular, deep blue) And green light emission can be realized.
Here, the iridium complex (dopant) according to the present invention is preferably doped in an amount of about 0.1 to 50% by weight with respect to the light emitting layer. If the content of the dopant is less than 0.1 wt%, it may be difficult to expect the effect of doping. If the content of the dopant is more than 50 wt%, the composition of the host and the dopant may be reversed.
Meanwhile, the iridium complex according to the present invention can be used for a flat panel display, a planar illuminant, an illuminant for a surface-emitting OLED for illumination, a flexible illuminant, a copier, a printer, an LCD backlight, a meter light source, And organic electronic devices such as an organic solar cell (OSC), an electronic paper (e-paper), an organic photoconductor (OPC), and an organic transistor (OTFT) may act on a principle similar to that applied to an organic light emitting device.
The iridium complex according to the present invention comprises the steps of: (a) reacting a compound represented by the following formula (1) with 2-bromophenylboronic acid to obtain a compound represented by the following formula (2); (b) reacting the obtained compound represented by the following formula (2) with a compound represented by the following formula (3) to obtain a compound represented by the following formula (4); (c) adding tris (dibenzylideneacetone) dipalladium (0), CuI, potassium carbonate, 18-crown-6 and nitrobenzene to the obtained compound represented by the following general formula (4) Obtaining a compound; And (d) adding iridium chloride and 2-ethoxyethanol to the obtained compound represented by the following general formula (5) and reacting them to obtain a compound represented by the following general formula (I).
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
(I)
In the above formulas,
Ar 1 is each independently selected from the group consisting of C1 to C20 alkyl (for example, C1 to C5 alkyl), C1 to C20 alkoxy (for example, C1 to C5 alkoxy), C6 to C30 aryl, A C1 to C20 haloalkyl group such as a C1 to C5 haloalkyl group, a halogen atom, a trifluoromethyl group, a cyano group, a phenyl group, a carbazole group, a thiophene group, a benzothiazole group, ≪ / RTI > unsubstituted or substituted with one or more of < RTI ID = 0.0 >
At least one of a hydrogen atom, a C1 to C20 alkyl (e.g., C1 to C5 alkyl), a C1 to C20 alkoxy (e.g., C1 to C5 alkoxy), a C6 to C30 aryl, N, O, A heterocyclic group of C5 to C30 which is substituted by at least one substituent selected from the group consisting of halogen, phenyl, naphthyl, anthracenyl, pyridine, pyrazine, pyrazole, imidazole, triazine, carbazole, quinoxaline, thiazole, fluorenyl, thiophene, As furan, benzofuran, dibenzofurane, or fluorine,
Each Ar < 1 > may form a mutual condensation ring.
Ar 2 is a hydrogen atom, a C 1 to C 20 alkoxy (e.g., methoxy) or a halogen (e.g., fluorine).
3 and 4 are UV (Ultraviolet) / PL (Photoluminescence) spectra of Compound 1 prepared according to the present invention. The UV / PL spectrum is a graph measuring the emission wavelength of each compound in order to characterize the OLED, and measuring the wavelength at which light is most emitted by irradiating light of a wavelength absorbed through UV. The UV / PL spectrum can be obtained through a method known in the art. In the present invention, a solid film prepared by coating a solution containing Compound 1 in Quartz is irradiated with excitation light to obtain a spectrum.
As a result, as shown in FIG. 4, the iridium complex according to the present invention has a maximum emission peak at about 463 nm, and thus it is expected that the luminous efficiency is extremely excellent.
Organic field Light emitting element
According to another aspect of the present invention, there is provided an organic electroluminescent device comprising an iridium complex as described above as an organic material layer.
The organic layer of the organic electroluminescent device of the present invention may have a single layer structure of one layer or a multilayer structure of two or more layers including a light emitting layer. Here, in the case where the organic material layer has a multilayer structure, it may be a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like are stacked. That is, the organic electroluminescent device of the present invention may have the structure shown in FIG. 1 (single layer structure) and FIG. 2 (multiple layer structure), but it is not limited thereto.
Specifically, the present invention comprises a first electrode (02), a second electrode (03) formed on a substrate (01), and at least one organic layer disposed between the electrodes and at least one layer of the organic layer An organic electroluminescent device comprising an iridium complex according to the present invention is provided.
More specifically, the present invention is an organic electroluminescent device comprising a first electrode (02), a second electrode (03) formed on a substrate (01) and one or more organic layers disposed between the electrodes The organic layer includes the light emitting layer 06 and the light emitting layer 06 includes the iridium complex according to the present invention. Here, the one or more organic layers may include at least one layer selected from the group consisting of a hole injection layer 04, a hole transport layer 05, a hole blocking layer (not shown), an electron transport layer 07 and an electron injection layer 08 As shown in FIG. For example, in the organic electroluminescent device of the present invention, the organic material layer includes a hole injecting layer 04, a hole transporting layer 05, a light emitting layer 06, a hole blocking layer (not shown), an electron transporting layer 07, 08, and one or two layers of a hole injection layer 04, a hole transport layer 05, a hole blocking layer (not shown), an electron transport layer 07 and an electron injection layer 08 are formed as needed Can be used in an omitted state.
The organic electroluminescent device of the present invention can be manufactured by a conventional method and materials for manufacturing an organic electroluminescent device, except that the above-described iridium complex is used to form one or more organic layers.
For example, the organic electroluminescent device according to the present invention may be formed by depositing a metal and a conductive material on the substrate 01 by using a known PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation A hole transporting layer 05, a light emitting layer 06, a hole blocking layer (not shown), and an electron transporting layer 07 (not shown) are formed on the anode 02 by depositing a metal oxide or an alloy thereof. And an electron injection layer 08, and then depositing a material usable as the cathode 03 on the organic layer. An organic electroluminescent device may also be manufactured by sequentially depositing a cathode 03 material, an organic material layer, and an anode 02 material on the substrate 01. Herein, the organic material layer may be formed by using a variety of polymer materials, but not by evaporation, but by using a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Can also be produced.
As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specifically, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), titanium oxide (TiO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, no.
As the negative electrode material, a material having a small work function is preferably used to facilitate electron injection into the organic material layer. Specifically, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiAl and LiF / Al or LiO2 / Al, but the present invention is not limited thereto.
As the hole injection layer material, it is preferable that HOMO (Highest Occupied Molecular Orbital) of the hole injection layer material be between the work function of the anode material and the HOMO of the surrounding organic layer . It is also preferable to use a material having a surface adhesion with the anode and a planarizing ability capable of alleviating the surface roughness of the anode. Materials having HOMO and LUMO (Lowest Unoccupied Molecular Orbital) values larger than the band gap of the light emitting layer and materials having high chemical stability and thermal stability are preferable. Specifically, the hole injection layer material may be selected from the group consisting of metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene Perylene based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers may be used, but the present invention is not limited thereto.
As the hole transport layer material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is preferable. Materials having HOMO and LUMO values larger than the band gap of the light emitting layer and materials having high chemical stability and thermal stability are preferable. Specifically, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together may be used, but the present invention is not limited thereto.
The light emitting layer material is a material capable of emitting light in the visible light region by transporting holes and electrons from the hole transporting layer and the electron transporting layer, respectively. In the present invention, the iridium complex is used as the light emitting layer material.
In one preferred embodiment, the light emitting layer in the organic electroluminescent device of the present invention may be a host doped with the iridium complex as a dopant. In the case of single emission, efficiency and brightness are very low, and the molecules are brought close to each other, so that excimer characteristics other than the intrinsic characteristics of each molecule can be exhibited. As a result, a dopant material is doped on a host material It is preferable to use one light-emitting layer. When the dopant material is doped on the host material, the dopant material returns to the ground state and the light emitted from the host material returns to the ground state.
As the hole blocking layer material, a material larger than the HOMO value of the light emitting layer is preferable. Materials having high chemical stability and thermal stability are also desirable. Specifically, TPBi and BCP are mainly used, and CBP, PBD, PTCBI, and BPhen may be used, but the present invention is not limited thereto.
As the electron transport layer and the electron injection layer material, a material capable of injecting electrons from the cathode well and transferring the electrons to the light emitting layer is preferable. Materials with high chemical stability and thermal stability are also suitable. Specifically, Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex, and the like may be used, but the present invention is not limited thereto.
The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
Hereinafter, the present invention will be described more specifically by way of Synthesis Examples and Examples. However, these synthesis examples and examples are provided only for the understanding of the present invention, and the scope of the present invention is not limited to these examples in any sense.
Synthesis Example 1: Preparation of compound 1
<Step 1>
To a dried round flask was added 1 eq of 2-bromobenzaldehyde (10 g, 0.054 mol), 1.3 eq of 2-bromophenylboronic acid (14.11 g, 0.07 mmol), tetrakis (triphenylphosphine) 0.002 mol) were charged and sufficiently filled with nitrogen. Then, 150 ml of dimethylformamide and 100 ml of triethylamine were added and the mixture was refluxed at 100 ° C for 20 hours.
Then, distilled water was added to complete the reaction. After extraction with dimethyl ether and distilled water, the organic layer was dried with anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure and the resulting mixture was purified by column chromatography with ethyl acetate / hexane to obtain intermediate A.
<Step 2>
To the dried round flask was added 1 eq of intermediate A (2 g, 0.007 mol), 3 eq of ammonium acetate (1.77 g, 0.229 mol) and 1 eq of 2,3-butanedione (0.66 g, 0.007 mol) And the mixture was refluxed at 150 ° C for 12 hours.
Then, the precipitate was filtered with distilled water, and then washed with distilled water and ethyl ether to obtain intermediate B.
<Step 3>
0.03 eq., CuI (0.31 g, 0.0016 mol), potassium carbonate (3.38 g, 0.024 mol), tris (dibenzylideneacetone) dipalladium (0) mol) and 18-crown-6 ether (0.80 g, 0.003 mol) were charged, and after the decompression, nitrogen was sufficiently charged. 60 ml of nitrobenzene was then added and the mixture was refluxed for 6 hours.
Subsequently, the mixture was cooled to room temperature, reduced in pressure to remove the solvent, extracted with dichloromethane and distilled water, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure, and the resulting mixture was purified by column chromatography with ethyl acetate / hexane to obtain intermediate C.
<Step 4>
The intermediate C 1eq and 0.1eq of iridium (III) chloride were added to a dried round flask, and the flask was sufficiently filled with nitrogen, and 2-ethoxyethanol was added thereto, followed by reflux stirring at 250 ° C for 24 hours.
The resulting mixture was purified by column chromatography with ethyl dichloromethane to give Compound 1. < 1 >
MALDI-TOF: m / z = 927.86 (C 51 H 39 IrN 6 = 928.11)
Synthesis Example 2: Preparation of Compound 2
Compound 2 was prepared in the same manner except that benzyl (1,2-diphenylethanedione) was used in place of 2,3-butanedione in Step 2 of Synthesis Example 1.
MALDI-TOF: m / z = 1300.88 (C 81 H 51 IrN 6 = 1300.53)
Synthesis Example 3: Preparation of Compound 3
Compound 3 was prepared in the same manner except that glyoxal was used instead of 2,3-butanedione in < Step 2 > of Synthesis Example 1.
MALDI-TOF: m / z = 842.99 (C 45 H 27 IrN 6 = 843.95)
Synthesis Example 4: Preparation of Compound 4
Compound 4 was prepared in the same manner except that dimethyl oxalate was used in place of 2,3-butanedione in < Step 2 > of Synthesis Example 1.
MALDI-TOF: m / z = 1023.65 (C 51 H 39 IrN 6 O 6 = 1024.11)
Synthesis Example 5: Preparation of Compound 5
Compound 5 was prepared in the same manner except that 2-bromo-4-methoxybenzaldehyde was used instead of 2-bromobenzaldehyde in < Step 1 > in Synthesis Example 1.
MALDI-TOF: m / z = 1018.33 (C 54 H 45 IrN 6 O 3 = 1018.19)
Synthesis Example 6: Preparation of Compound 6
Compound 6 was prepared in the same manner except that 2-bromo-4-methoxybenzaldehyde was used instead of 2-bromobenzaldehyde in < Step 1 > in Synthesis Example 2.
MALDI-TOF: m / z = 1389.27 (C 84 H 57 IrN 6 O 3 = 1390.61)
Synthesis Example 7: Preparation of Compound 7
Compound 7 was prepared in the same manner except that 2-bromo-4-methoxybenzaldehyde was used in place of 2-bromobenzaldehyde in Step 1 of Synthesis Example 3.
MALDI-TOF: m / z = 933.95 (C 48 H 33 IrN 6 O 3 = 934.03)
Synthesis Example 8: Preparation of Compound 8
Compound 8 was prepared in the same manner as in Synthesis Example 4, except that 2-bromo-4-methoxybenzaldehyde was used instead of 2-bromobenzaldehyde.
MALDI-TOF: m / z = 1114.56 (C 54 H 45 IrN 6 O 9 = 1114.19)
Synthesis Example 9: Preparation of Compound 9
Compound 9 was prepared in the same manner as in Synthesis Example 1, except that 2-bromo-4-fluorobenzaldehyde was used instead of 2-bromobenzaldehyde in Step 1 of Synthesis Example 1.
MALDI-TOF: m / z = 982.21 (C 51 H 36 F 3 IrN 6 = 982.08)
Synthesis Example 10: Preparation of Compound 10
Compound 10 was prepared in the same manner as in Synthesis Example 2 except that 2-bromo-4-fluorobenzaldehyde was used instead of 2-bromobenzaldehyde in Step 1 of Synthesis Example 2.
MALDI-TOF: m / z = 1354.95 (C 81 H 48 F 3 IrN 6 = 1354.5)
Synthesis Example 11: Preparation of Compound 11
Compound 11 was prepared in the same manner except that 2-bromo-4-fluorobenzaldehyde was used instead of 2-bromobenzaldehyde in Step 1 of Synthesis Example 3.
MALDI-TOF: m / z = 898.25 (C 45 H 25 F 3 IrN 6 = 898.93)
Example One: Organic field Manufacturing of light emitting device
Before the deposition for the device fabrication, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1500Å was cleaned (impurities and fine particles on the surface were deformed by organic substances, deterioration of interfacial properties between ITO and organic materials, A phenomenon in which light is not partially or totally caused due to burning of impurities at the time of contact, defective contact with ITO, and shortening of the lifetime of the device). In order to remove impurities such as organic substances, ionic substances, and metallic substances present on the substrate before the organic material deposition, the substrate was removed by ultrasonic cleaning for 5 minutes at room temperature with acetone, and then 5 parts by IPA (Isopropyl alcohol) After ultrasonic cleaning for a minute, N 2 gas.
HAT-CN, which is a hole injection layer, was vacuum deposited on the thus-prepared ITO transparent electrode to a thickness of 100 Å and a hole transport material TAPC was vacuum deposited thereon to a thickness of 500 Å. Then, mCBP as a light emitting layer was doped with Compound 1 obtained in Synthesis Example 1 in an amount of 12% 300 Å, and BmPyPb was vacuum deposited as an electron transport layer to a thickness of 400 Å. Lithium fluoride (LiF) 10 Å thick and aluminum having a thickness of 1200 Å were sequentially deposited to form a cathode. Here, the deposition rate of the organic material was 1 Å / sec, the deposition rate of lithium fluoride was 0.1 Å / sec, and the deposition rate of aluminum was 1 Å / sec.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 2: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 2 obtained in Synthesis Example 2 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 3: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 3 obtained in Synthesis Example 3 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 4: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 4 obtained in Synthesis Example 4 was used instead of Compound 1 as a luminescent layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
.
Example 5: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 5 obtained in Synthesis Example 5 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 6: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 6 obtained in Synthesis Example 6 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 7: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 7 obtained in Synthesis Example 7 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 8: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 8 obtained in Synthesis Example 8 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 9: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 9 obtained in Synthesis Example 9 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 10: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 10 obtained in Synthesis Example 10 was used instead of Compound 1 as a light emitting layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Example 11: Manufacture of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 11 obtained in Synthesis Example 11 was used instead of Compound 1 as a luminescent layer dopant.
The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m 2 ), the luminescence brightness at a current density of 10 mA / cm 2 , the luminous efficiency, and the like are shown in Table 1 below.
Comparative Example 1: Fabrication of organic electroluminescent device
An organic electroluminescent device was prepared in the same manner as in Example 1, except that FIrpic represented by the following formula (II) was used instead of Compound 1 as the luminescent layer dopant.
[Chemical Formula II] FIrpic
[Table 1]
As shown in Table 1, when an iridium complex according to the present invention is used as a light emitting layer material, an organic electroluminescent device is manufactured using organic electroluminescent materials such as low voltage, high efficiency, high brightness and high color purity based on excellent hole transporting and electron transporting ability It is possible to harmonize the various characteristics required for the device.
On the other hand, the present inventors conducted a simulation to anticipate and compare characteristics of a conventional iridium complex introduced with a substituent only on one side and an iridium complex introduced with substituents on both sides according to the present invention. (The absorption spectrum by simulation shows that the wavelength of the light designed to emit from the display does not overlap with the wavelength of light absorbed by the molecule. If there is an overlap of wavelengths, It is possible to reduce the efficiency of the device greatly by comparing the absorption spectrum of the device with the absorption spectrum which does not overlap with the emission spectrum of the display itself, There is an advantage of being able to quickly screen substances with physical properties.)
<Simulation condition>
- Program name: material science
- Calculation name: absorption spectrum
- Calculation options: dftname = B3LYP, basis = MIDIX
As a result, the data after the simulation calculation and the PL measurement data (FIGS. 6 to 8) are comparable, and in the case of the blue iridium phosphorescent dopant, substitution of both substituents on the imidazole moiety Respectively.
01: substrate
02: anode (or first electrode)
03: cathode (or second electrode)
04: Hole injection layer
05: Hole transport layer
06: light emitting layer
07: Electron transport layer
08: Electron injection layer
Claims (10)
Characterized in that it is used as a blue dopant material of an organic electroluminescent light emitting layer.
Iridium complex:
(a) reacting a compound represented by the following formula (1) with 2-bromophenylboronic acid to obtain a compound represented by the following formula (2);
(b) reacting the obtained compound represented by the following formula (2) with a compound represented by the following formula (3) to obtain a compound represented by the following formula (4);
(c) adding tris (dibenzylideneacetone) dipalladium (0), CuI, potassium carbonate, 18-crown-6 and nitrobenzene to the obtained compound represented by the following general formula (4) Obtaining a compound; And
(d) introducing iridium chloride and 2-ethoxyethanol into the obtained compound represented by the following formula (5) and reacting to obtain a compound represented by the following formula (I)
Wherein the iridium complex compound is used as a blue dopant material in an organic electroluminescent device emitting layer.
Method of preparing iridium complex:
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
(I)
In the above formulas,
Ar 1 is phenyl and Ar 2 is hydrogen, methoxy or fluorine.
Wherein the one or more organic layers include a blue light emitting layer,
Wherein the blue light emitting layer is a host material doped with an iridium complex according to claim 1,
Organic electroluminescent device.
Wherein the at least one organic material layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer and an electron injection layer.
Organic electroluminescent device.
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| US20080297033A1 (en) * | 2006-02-10 | 2008-12-04 | Knowles David B | Blue phosphorescent imidazophenanthridine materials |
| JP4564588B1 (en) * | 2009-08-31 | 2010-10-20 | 富士フイルム株式会社 | Material for organic electroluminescence device and organic electroluminescence device |
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| US20080297033A1 (en) * | 2006-02-10 | 2008-12-04 | Knowles David B | Blue phosphorescent imidazophenanthridine materials |
| JP4564588B1 (en) * | 2009-08-31 | 2010-10-20 | 富士フイルム株式会社 | Material for organic electroluminescence device and organic electroluminescence device |
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