WO2012138172A2 - 신규 유기금속 화합물 및 이를 이용한 유기 발광 소자 - Google Patents
신규 유기금속 화합물 및 이를 이용한 유기 발광 소자 Download PDFInfo
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- WO2012138172A2 WO2012138172A2 PCT/KR2012/002624 KR2012002624W WO2012138172A2 WO 2012138172 A2 WO2012138172 A2 WO 2012138172A2 KR 2012002624 W KR2012002624 W KR 2012002624W WO 2012138172 A2 WO2012138172 A2 WO 2012138172A2
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- WIPO (PCT)
- Prior art keywords
- formula
- organometallic compound
- light emitting
- organic light
- compound
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- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- -1 organometallic iridium compound Chemical class 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 229910052741 iridium Inorganic materials 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract description 19
- 239000007787 solid Substances 0.000 abstract description 11
- 230000009878 intermolecular interaction Effects 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 238000010129 solution processing Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 70
- 239000000243 solution Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000000539 dimer Substances 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000004020 luminiscence type Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 0 CCCCCC1*2C1C(CCCC*)CC2 Chemical compound CCCCCC1*2C1C(CCCC*)CC2 0.000 description 6
- 229920000144 PEDOT:PSS Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 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 3
- PRNGIODVYLTUKH-UHFFFAOYSA-N 5-bromo-2-phenylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CC=C1 PRNGIODVYLTUKH-UHFFFAOYSA-N 0.000 description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- BTEAMLUWLVUBFF-UHFFFAOYSA-N 5-(3-methylphenyl)-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound CC=1C=C(C=CC1)C1=C(C=CC(C1)(N)N)C1=CC=CC=C1 BTEAMLUWLVUBFF-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000327 poly(triphenylamine) polymer Polymers 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- 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
- GMMYHFWPAAFOKN-UHFFFAOYSA-N 1,1'-biphenyl;n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 GMMYHFWPAAFOKN-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- IXPCGYRPYYJIEQ-UHFFFAOYSA-N C1=CO[C](c2ccccc2)O1 Chemical compound C1=CO[C](c2ccccc2)O1 IXPCGYRPYYJIEQ-UHFFFAOYSA-N 0.000 description 1
- TUBMGEQOUUYWDN-UHFFFAOYSA-N CC(CC(C)=[O]1)OC1=C Chemical compound CC(CC(C)=[O]1)OC1=C TUBMGEQOUUYWDN-UHFFFAOYSA-N 0.000 description 1
- GYHRAMLZCMFGFU-UHFFFAOYSA-N C[C]1OC=CO1 Chemical compound C[C]1OC=CO1 GYHRAMLZCMFGFU-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- NPRDEIDCAUHOJU-UHFFFAOYSA-N [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NPRDEIDCAUHOJU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000011692 calcium ascorbate Substances 0.000 description 1
- ZZBNZZCHSNOXOH-UHFFFAOYSA-N chloro(trimethyl)germane Chemical compound C[Ge](C)(C)Cl ZZBNZZCHSNOXOH-UHFFFAOYSA-N 0.000 description 1
- ONQMBYVVEVFYRP-UHFFFAOYSA-N chloro(triphenyl)germane Chemical compound C=1C=CC=CC=1[Ge](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 ONQMBYVVEVFYRP-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Definitions
- the present invention relates to a novel organometallic compound, and more particularly, to a luminescent organometallic compound having improved luminescence properties by inhibiting intermolecular interactions by the introduction of germanium substituents, an organic electronic device using the same, and more particularly to an organic light emitting device will be.
- OLED Organic Light-Emitting Diode
- OLED is basically a structure in which an organic thin film including an organic light emitting layer is sandwiched between two electrodes, wherein at least one of the two electrodes is transparent and suitable between the two electrodes. It is a kind of organic electronic device that utilizes the light emitted from the visible light region from the organic light emitting layer when a voltage, generally, a voltage between 5 V and 10 V is applied.
- Such an organic light emitting device is basically a self-luminous device having a very thin thickness of several micrometers or less, including an electrode, and emitting light directly from the device itself.
- the response speed is high and the viewing angle is wide as a display device.
- the manufacturing process is simple and the flexible device using the organic thin film can be realized, and the device can be implemented not only in the vacuum process but also from the solution state in some cases, it can be realized in the next generation display device and lighting. Research is underway.
- the organic light emitting layer is composed of at least one organic and organometallic compound or an organic / inorganic hybrid material, and according to the light emitting mechanism, a fluorescent method due to the emission attenuation of the singlet excitons or a phosphorescent method using the emission attenuation of the triplet excitons. It can be divided into two.
- the most important key component of such a phosphorescent organic light emitting device is a phosphorescent material, and most organometallic compounds are well known, and among them, an organometallic compound mainly based on iridium occupies a large number.
- the optical and electrical properties of the final iridium organometallic compound can be controlled according to the chemical structure of the ligand that coordinates the iridium atom, thereby synthesizing the organometallic compound suitable for various requirements. There is an advantage to this.
- iridium organometallic compounds having phenylpyridine as the basic structure of the ligand for example tris (2-phenylpyridine) iridium (III) (hereinafter Ir (ppy) 3 ), are well known (see JP 3992929).
- the present inventors while conducting research to solve the above problems, introduces a germanium substituent to the iridium ligand to synthesize a novel organometallic compound with improved luminous efficiency by inhibiting the interaction of molecules, such a compound in the solution phase
- the present invention was completed by confirming that it can be dissolved well and use a solution process, and the luminescence property is improved to be equal to or higher than that of a conventional organometallic compound and can be usefully used in an organic light emitting device.
- Another object of the present invention to provide an organic light emitting device comprising the novel organometallic compound.
- the present invention provides a novel organometallic compound represented by the following formula (1).
- the present invention also provides an organic light emitting device comprising the novel organometallic compound.
- step 1 Dissolving the novel organometallic compound in an organic solvent to prepare a solution (step 1);
- step 2 After dropping the solution of the step 1 on the substrate and rotating the substrate, it provides a method for forming a thin film for an organic light emitting device comprising the step of drying to form a thin film on the substrate (step 2).
- the intermolecular interaction in the solid state is suppressed by introducing germanium substituents into the iridium organometallic compound matrix, which can be usefully used in the solution process, and the luminous efficiency when used as part of the light emitting layer of the organic light emitting device. Since this is remarkably improved, it can be usefully used as a material for an organic light emitting device.
- FIG. 1 to 3 are schematic cross-sectional views of organic light emitting diodes according to the present invention, respectively.
- Example 5 is a graph showing current density-luminescence efficiency of organic light emitting diodes manufactured in Examples 4, 5, and Comparative Example 1 of the present invention.
- Example 6 is a voltage-brightness / voltage-current graph of the organic light emitting diodes manufactured in Examples 4, 5 and Comparative Example 1 of the present invention.
- Example 7 is a current density-luminescence efficiency graph of the multilayer organic light emitting device manufactured in Example 6 of the present invention.
- Example 8 is a voltage-brightness / voltage-current graph of the multilayer organic light emitting device manufactured in Example 6 of the present invention.
- the organometallic compound according to the present invention is characterized by represented by the following formula (1):
- At least one of R 1 to R 4 is a substituent represented by the following formula (2);
- R 1 to R 4 is not a substituent of Formula 2, independently of one another hydrogen, deuterium, halogen, cyano, C 1 -C 18 straight or branched chain alkyl, C 1 -C 18 straight or branched chain alkoxy, C 6 ⁇ C 18 aryl, C 3 -C 18 cycloalkyl, C 4 -C 18 heteroaryl or 5- to 6-membered heterocycloalkyl, wherein the alkyl or alkoxy is unsubstituted or substituted with halogen and the aryl, cyclo Alkyl, heteroaryl or heterocycloalkyl is unsubstituted or substituted with halogen or C 1 -C 18 straight or branched alkyl, said heteroaryl or heterocycloalkyl comprises at least one atom selected from N, O and S in the ring and;
- R 5 to R 8 are independently of each other hydrogen, deuterium, halogen, cyano, C 1 -C 18 straight or branched chain alkyl, C 1 -C 18 straight or branched chain alkoxy, C 6 -C 18 aryl, C 3 -C 18 Cycloalkyl, C 4 -C 18 heteroaryl or 5- to 6-membered heterocycloalkyl, wherein the alkyl or alkoxy is unsubstituted or substituted with halogen and the aryl, cycloalkyl, heteroaryl or heterocycloalkyl is Unsubstituted or substituted with halogen or C 1 -C 18 straight or branched alkyl, wherein said heteroaryl or heterocycloalkyl comprises one or more atoms selected from N, O and S in the ring;
- n 2 or 3.
- L 1 to L 3 are independently of each other hydrogen, deuterium, halogen, cyano, C 1 -C 18 straight or branched alkyl, C 1 -C 18 straight or branched alkoxy, C 6 -C 18 aryl, C 3 -C 18 Cycloalkyl, C 4 -C 18 heteroaryl or 5- to 6-membered heterocycloalkyl, wherein the alkyl or alkoxy is unsubstituted or substituted with halogen and the aryl, cycloalkyl, heteroaryl or heterocycloalkyl is Unsubstituted or substituted with halogen or C 1 -C 18 straight or branched alkyl, wherein said heteroaryl or heterocycloalkyl comprises one or more atoms selected from N, O and S in the ring).
- the organometallic compound according to the present invention is characterized in that the compound represented by the formula (1A).
- L 1 to L 3 is independently from each other is characterized in that methyl, ethyl, propyl, isopropyl, cyclohexyl, phenyl.
- R 5 to R 8 are independently of each other hydrogen, methyl, phenyl, methylphenyl. It is characterized by being dimethylphenyl.
- a and B are each independently one selected from the group consisting of N (nitrogen), O (oxygen), S (sulfur), P (phosphorus) and C (carbon).
- the bidentate ligand represented by is characterized in that it is selected from the group consisting of compounds of the following formula.
- organometallic compound according to Chemical Formula 1 include Ir (PhGe-ppy) 3 , Ir (MeGe-ppy) 3 , and Ir (MeGe-ppy) 2 (acac), but are not limited thereto. Do not.
- the present invention also provides a method for producing the novel organometallic compound.
- step 2 The compound of formula 6 and the iridium complex compound prepared in step 1 is mixed with glycerol to reflux to prepare an organometallic compound of formula 1a coordinated with the three saccharide compounds of formula (6) (step 2).
- Step 1 is a step of preparing a phenylpyridine compound substituted with a germanium substituent of Formula 4 by reacting a phenylpyridine compound of Formula 2 with a germanium containing compound of Formula 3 and a lithium salt.
- the germanium substituent of Chemical Formula 4 is substituted by adding the compound of Chemical Formula 2 to an organic solvent such as tetrahydrofuran (THF), diethan ether (diethyl ether), and adding a germanium-containing compound of Chemical Formula 3 and a lithium salt to react.
- organic solvent such as tetrahydrofuran (THF), diethan ether (diethyl ether), and adding a germanium-containing compound of Chemical Formula 3 and a lithium salt to react.
- Phenylpyridine compound can be prepared.
- the compound of formula (2) and the compound of formula (3) that is a starting material may be purchased by commercially available, or may be prepared by a manufacturing method commonly used in the art.
- n-BuLi, sec-BuLi, tert-BuLi, or the like may be used, and preferably n-BuLi may be used.
- the reaction is preferably carried out at a low temperature of -75 ⁇ -80 °C, after the reaction is completed may be further performed to perform a column chromatography to purify the product.
- step 2 is a step of preparing the organometallic compound of Formula 1a in which the compound of Formula 6 prepared in Step 1 and the iridium complex compound are mixed and refluxed to coordinate the three zuligand compounds of Formula 6.
- the compound of Formula 6 and the iridium complex compound is mixed with glycerol at a ratio of 2 to 3: 1 mol, stirred at reflux for 23 to 27 hours, cooled to room temperature, and then added with acid to add
- An organometallic compound of Formula 1a may be prepared in which a ligand compound of 6 is coordinated. Thereafter, the extraction of the organic solvent and column chromatography may be performed to further purify the product.
- step A Reacting a phenylpyridine compound of formula 4 with a germanium containing compound of formula 5 and a lithium salt to prepare a phenylpyridine compound substituted with a germanium substituent of formula 6 (step A);
- Step B Preparing a diiridium dimer of Chemical Formula 7 by mixing the compound of Chemical Formula 6 prepared in Step A with iridium trichloride (IrCl 3 ) and a solvent and reacting at reflux (step B); And
- step C The diiridium dimer compound and the secondary ligand compound of formula 7 prepared in step B ( -H) is added to an organic solvent and a coupling reaction is carried out to produce a compound of Formula 1b (step C).
- step A is a step of preparing a phenylpyridine compound substituted with a germanium substituent of Formula 6, it may be carried out in the same manner as step 1 of Scheme 1.
- step B is a step of preparing a diiridium dimer of formula (7) by mixing the compound of formula (6) prepared in step A with iridium trichloride (IrCl 3 ) and a solvent and reacting at reflux temperature.
- iridium trichloride IrCl 3
- iridium trichloride (IrCl 3 ) and the compound of formula (6), which is a ligand, are mixed in a solvent at a ratio of 1: 2 to 3 mol to reflux, and then diiridium dimer is separated.
- the solvent in the above step is preferably an alcohol or an alcohol / water mixed solvent, and examples thereof include 2-ethoxyethanol and 2-ethoxyethanol / water mixed solvent.
- step C is a diiridium dimer compound and the secondary ligand compound of Formula 7 prepared in step B ( -H) is a step of preparing a compound of Formula 1b by coupling into an organic solvent.
- the separated diiridium dimer is a secondary ligand compound ( -H) is mixed together with an organic solvent and heated to prepare an organometallic compound having a ligand: auxiliary ligand of 2: 1 as a final product.
- the main and secondary ligands of the final product are appropriately determined and used according to the composition ratio, wherein AgCF 3 SO 3 , Na 2 CO 3 , NaOH and the like are used as organic solvents 2-ethoxyethanol, 2-methoxy
- the mixture can be reacted with ethyl ether and 1,2-dichloroethane.
- the organometallic compound of Formula 1 according to the present invention includes at least one germanium substituent of Formula 2, thereby inhibiting the interaction between the organometallic compound molecules in the solid phase as compared with the unsubstituted compound, thus the performance of the organic light emitting device, in particular the luminous efficiency. Can improve.
- the organometallic compound of Formula 1 according to the present invention includes at least one germanium substituent of Formula 2, thereby increasing the solubility in organic solvents compared to the unsubstituted compound. Accordingly, in producing an organic thin film containing the organometallic compound of Formula 1 from the solution phase, the concentration of the compound of Formula 1 in the solution may be increased.
- the organometallic compound of the formula (1) according to the present invention by introducing a germanium substituent to the iridium organometallic compound matrix can inhibit the intermolecular interaction in the solid state can be usefully used in the solution process, the light emitting layer of the organic light emitting device When used as a part, since the luminous efficiency is remarkably improved, it can be usefully used as a material for an organic light emitting device.
- the solution process may use a spin coating method, inkjet printing, screen printing, gravure printing, etc.
- the compound of Formula 1 according to the present invention may be applied to a general thin film forming method such as vacuum thermal deposition, dip coating.
- the present invention provides an organic light emitting device including the organometallic compound of Formula 1 in a light emitting layer.
- the organic light emitting device is a monolayer comprising a light emitting layer including the compound of Formula 1 as a light emitting host material as one structural unit between an anode, a cathode, and two electrodes, or an anode together with a charge transport layer. It has a multi-layered structure in which the light emitting layer and the cathode containing a compound of the light emitting material in order.
- the first electrode Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer may include at least one organometallic compound represented by Chemical Formula 1.
- a multilayer device having a combination of a light emitting layer and a charge transporting layer exhibits superior characteristics, rather than a single layered device consisting of only one light emitting layer, which is an energy barrier when charge is injected from an electrode by properly combining the light emitting material and the charge transporting material. This is because the charge transport layer binds the holes or electrons injected from the electrode to the light emitting layer region to balance the number density of the holes and electrons injected.
- the basic organic light emitting device of the present invention has a structure in which a transparent electrode (anode), a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a metal electrode (cathode) are sequentially stacked.
- a hole blocking layer is provided between the light emitting layer and the electron transporting layer as shown in FIG. 2, or as shown in FIG. 3, or a hole blocking layer between the light emitting layer and the electron transporting layer and between the light emitting layer and the hole transporting layer, respectively.
- an electron blocking layer is provided between the light emitting layer and the electron transporting layer.
- the transparent electrode (anode) and the metal electrode (cathode) are conventional electrode materials, for example, the transparent electrode is indium tin oxide (ITO) or SnO 2 , and the metal electrode is It may be formed of a metal such as Li, Mg, Ca, Ag, Al and In or an alloy thereof, and the metal electrode may have a single layer or a multilayer structure of two or more layers.
- the transparent electrode is indium tin oxide (ITO) or SnO 2
- the metal electrode is It may be formed of a metal such as Li, Mg, Ca, Ag, Al and In or an alloy thereof, and the metal electrode may have a single layer or a multilayer structure of two or more layers.
- the compound of Chemical Formula 1 of the present invention may be used as a dopant material, and may have a single layer or a multilayer structure of two or more layers.
- the compound of Formula 1 may further include a phosphorescent dopant, the phosphorescent dopant is commonly used in the art, tris (2-phenylpyridinato-N, C2) ruthenium, bis (2-phenyl Pyridinato-N, C2) palladium, bis (2-phenylpyridinato-N, C2) platinum, tris (2-phenylpyridinato-N, C2) osmium, tris (2-phenylpyridinato-N , C2) rhenium, octaethyl platinum porphyrin, octaphenyl platinum porphyrin, octaethyl palladium porphyrin, octaphenyl palladium porphyrin, irid
- the hole transport layer is a conventional hole transport material such as 4,4-bis [N- (1-naphthyl) -N-phenyl-amine] biphenyl ( ⁇ -NPD), N, N-diphenyl-N, N-bis (3-methylphenyl) -1,1-biphenyl-4,4-diamine (TPD) and poly- (N-vinylcarbazole) (PVCz) may be included alone or in combination of two or more thereof. It can also be laminated
- the hole blocking layer has a lower un °C cupied molecular orbital (LUMO) value of 5.5 to 7.0 and a hole transport capacity is remarkably decreased, and the hole blocking layer is composed of a material having excellent electron transport ability, such as bassocuproin (Bath °C uproine). , BCP), 3- (4-biphenylyl) -4-phenyl-5- (4-t-butylphenyl) -1,2,4-triazole (TAZ) and bis (8-hydroxy-2- Methylquinolinato) -aluminum biphenoxide (BAlq) and the like are suitable.
- a material having a large LUMO value is generally used as the electron blocking layer, and iridium (III) tris (1-phenylpyrazole-N, C 2 ′) (Ir (ppz) 3 ) is suitable.
- the electron transporting layer may be composed of a conventional electron transporting material such as tris (8-quinolinolato) aluminum (Alq 3) or rubrene alone or in combination of two or more thereof. Two or more separate layers may be stacked.
- a conventional hole injection layer including, for example, copper phthalocyanine (CuPc) may be inserted between the anode and the hole transport layer, and the cathode and the electron transport layer may be inserted.
- a conventional electron injection layer containing LiF can be inserted.
- the anode, cathode, light emitting layer, transport layer, injection layer and blocking layer may be formed by a conventional deposition method.
- Step 1 Preparing a solution by dissolving the organometallic compound of Formula 1 in an organic solvent (step 1);
- step 2 After dropping the solution of the step 1 on the substrate and rotating the substrate, it provides a method for forming a thin film for an organic light emitting device comprising the step of drying to form a thin film on the substrate (step 2).
- the organometallic compound of Formula 1 according to the present invention includes at least one germanium substituent of Formula 2, thereby increasing the solubility in organic solvents as compared to the unsubstituted compound. Accordingly, in producing an organic thin film containing the organometallic compound of Formula 1 from the solution phase, the concentration of the compound of Formula 1 in the solution may be increased.
- 1,2-dichloroethane, chlorobenzene, toluene, etc. may be used as the organic solvent, but is not limited thereto.
- Step 1 Preparation of 3- (triphenyllow mille) -6-phenylpyridine
- 3-Bromo-6-phenylpyridine (0.86 g, 3.67 mmol) prepared in Preparation Example 1 was dissolved in anhydrous tetrahydrofuran (20 mL) and stirred at -78 ° C. Normal-butyllithium (1.76 mL, 4.41 mmol, 2.5 M hexane solution) was added dropwise to this solution over about 20 minutes. After stirring for an additional 1 hour, triphenylgermanium chloride (1.5 gm 4.41 mmol) was added and the reaction proceeded at room temperature overnight. Then water (100 mL) was added and the water and organic layers were separated.
- Steps B and C Ir (MeGe-ppy) 2 manufacture of (acac)
- step A 3- (trimethyllow density) -6-phenylpyridine (1.61 g, 5.91 mmol) and iridium (III) acetylacetonate (0.53 g, 1.77 mmol) prepared in step A were mixed with 2-ethoxyethanol (30 mL). Dissolved in water (10 mL) and stirred at 125 ° C for 12 h. After cooling to room temperature, excess water was added and the precipitate was filtered to give a cyclometalated Ir (III) ⁇ -chloro bridged dimer (0.60 g, yield 44%) (step B).
- step B In the dimer compound obtained in step B without further purification, acetylacetone (0.10 g, 1.00 mmol) and sodium carbonate (0.41 g, 3.9 mmol) were dissolved in 2-ethoxyethanol (10 mL) and heated to reflux at 170 ° C. for 12 hours. After the completion of the reaction, the solid formed while cooling to room temperature was filtered, washed with water, and the final product was purified by column chromatography on silica gel with dichloromethane as a developing solution to obtain the target compound (0.19 g, yield 30%) as a yellow solid.
- the patterned ITO substrate was ultrasonically cleaned with acetone and isopropanol for 10 minutes each, followed by drying with blowing nitrogen, followed by dry cleaning for 20 minutes in an ultraviolet-ozone cleaning apparatus.
- PEDOT: PSS (CLEVIOS TM P VP AI 4083) was spin-coated at 4200 rpm for 30 seconds on the cleaned ITO substrate, and dried at 120 ° C. in a vacuum oven for 1 hour to form a thin film of 40 nm.
- 50:10:31 of PVK Sigma-Aldrich Cat. No. 368350
- TPD Sigma-Aldrich Cat. No. 443263
- PBD Sigma-Aldrich Cat. No.
- Example 2 B8378 and Ir (PhGe-ppy) 3 synthesized in Example 1 It mixed at the ratio of: 9 (mass ratio), 1,2-dichloroethane was added so that total solid concentration might be 1.3 mass%, and the organic light emitting layer composition was prepared.
- the organic light emitting layer composition solution thus prepared was spin coated on the PEDOT: PSS coated ITO substrate at 1500 rpm for 30 seconds, and dried on a 55 ° C. hot plate to form a thin film of 80 nm. Spin coating and drying of the organic light emitting layer composition solution were all carried out in a glove box under a nitrogen atmosphere.
- the ITO substrate coated with PEDOT: PSS and the organic light emitting layer composition was transferred to a metal vacuum deposition chamber, and cesium fluoride and aluminum were vacuum-deposited 1 nm and 120 nm, respectively, under 10 -7 Torr vacuum.
- the organic light emitting device was encapsulated with a glass cover and an epoxy sealant in a glove box, and then the characteristics of the organic light emitting device were evaluated using a PR-650 spectra calorimeter and Keithley 2400 source measuring unit.
- An organic light emitting device was manufactured in the same manner as in Example 4, except that Ir (MeGe-ppy) 3 synthesized in Example 2 was used instead of Ir (PhGe-ppy) 3 as a component of the organic light emitting layer composition solution. And its properties were evaluated.
- the germanium-substituted Ir (PhGe-ppy) 3 and Ir (MeGe-ppy) 3 organic compounds of the organic light-emitting device As shown in FIGS. 4 to 6 and Table 1, compared to Ir (ppy) 3 as a comparative material, the germanium-substituted Ir (PhGe-ppy) 3 and Ir (MeGe-ppy) 3 organic compounds of the organic light-emitting device It was confirmed that the light emitting layer exhibited superior performance as the light emitting material, and it was confirmed that the emission efficiency of the organic light emitting device using the same was introduced by introducing germanium substituents into the organic light emitting material.
- the compound according to the present invention when used as part of the light emitting layer of the organic light emitting device, the light emission efficiency is remarkably improved, and thus, the compound according to the present invention may be usefully used as a material for an organic light emitting device.
- the poly (triphenylamine) solution (0.12 mass%, solvent: chlorobenzene) was spin-coated at 1500 rpm for 30 seconds, and then heated at 100 ° C. It was dried at to form a hole transport layer thin film of 10 nm. 73:10:10 of PVK (Sigma-Aldrich Cat. No. 368350), TPD (Sigma-Aldrich Cat. No. 443263), PBD (Sigma-Aldrich Cat. No.
- Example 2 B8378 and Ir (MeGe-ppy) 3 synthesized in Example 2 It mixed at the ratio of: 7 (mass ratio), and 1,2- dichloroethane was added so that total solid concentration might be 0.64 mass%, and the organic light emitting layer composition was prepared.
- the organic light emitting layer composition solution thus prepared was spin coated on the PEDOT: PSS and poly (triphenylamine) coated ITO substrate at 1800 rpm for 30 seconds, and dried on a 55 ° C. hot plate to form a 50 nm organic light emitting layer thin film. Spin coating and drying of the hole transport layer and the organic light emitting layer composition solution were all carried out in a glove box under a nitrogen atmosphere.
- the ITO substrate coated with the PEDOT: PSS, hole transporting layer and organic light emitting layer composition was transferred to a vacuum deposition chamber and TPBi (1,3,5-Tri (1-phenyl-1H-benzo [d] imidazol-) under 10 -7 Torr vacuum.
- 2-yl) phenyl and Lumtec Catalog No. LT-E302 were vacuum-evaporated to 57 nm to form an electron transport layer, and cesium fluoride and aluminum were then vacuum-deposited to 1 nm and 120 nm, respectively, under 10 -7 Torr vacuum.
- the organic light emitting device was encapsulated with a glass cover and an epoxy sealant in a glove box, and then the characteristics of the organic light emitting device were evaluated using a PR-650 spectra calorimeter and Keithley 2400 source measuring unit.
- the current density-luminescence efficiency graph of the organic light emitting diode of Example 6 was measured, and a voltage-brightness / voltage-current graph is shown in FIG. 8.
- the multilayer organic light emitting device manufactured by using the germanium-substituted Ir (MeGe-ppy) 3 showed excellent characteristics.
- germanium-substituted Ir (MeGe-ppy) 3 according to the present invention can be usefully used as an organic light emitting device.
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Abstract
Description
최대발광파장 (nm) | CIE 색좌표 (x,y) | 최대전류효율 (cd/A) | |
실시예 4 | 524 | (0.35, 0.61) | 20.9 |
실시예 5 | 520 | (0.33, 0.62) | 23.0 |
비교예 1 | 512 | (0.31, 0.61) | 17.0 |
Claims (11)
- 하기 화학식 1로 표시되는 유기금속 화합물:[화학식 1](상기 화학식 1에서,R1 내지 R4 중에서 적어도 하나는 하기 화학식 2로 표시되는 치환체이고;R1 내지 R4 중에서 하기 화학식 2의 치환체가 아닌 경우, 서로 독립적으로 수소, 중수소, 할로겐, 시아노, C1-C18 직쇄 또는 측쇄 알킬, C1-C18 직쇄 또는 측쇄 알콕시, C6-C18 아릴, C3-C18 시클로알킬, C4-C18 헤테로아릴 또는 5원 내지 6원의 헤테로시클로알킬이고, 이때, 상기 알킬 또는 알콕시는 비치환 또는 할로겐으로 치환되고, 상기 아릴, 시클로알킬, 헤테로아릴 또는 헤테로시클로알킬은 비치환 또는 할로겐 또는 C1-C18 직쇄 또는 측쇄 알킬로 치환되고, 상기 헤테로아릴 또는 헤테로시클로알킬은 고리 내 N, O 및 S로부터 선택되는 하나 이상의 원자를 포함하고;R5 내지 R8은 서로 독립적으로 수소, 중수소, 할로겐, 시아노, C1-C18 직쇄 또는 측쇄 알킬, C1-C18 직쇄 또는 측쇄 알콕시, C6-C18 아릴, C3-C18 시클로알킬, C4-C18 헤테로아릴 또는 5원 내지 6원의 헤테로시클로알킬이고, 이때, 상기 알킬 또는 알콕시는 비치환 또는 할로겐으로 치환되고, 상기 아릴, 시클로알킬, 헤테로아릴 또는 헤테로시클로알킬은 비치환 또는 할로겐 또는 C1-C18 직쇄 또는 측쇄 알킬로 치환되고, 상기 헤테로아릴 또는 헤테로시클로알킬은 고리 내 N, O 및 S로부터 선택되는 하나 이상의 원자를 포함하고;m은 2 또는 3이다).[화학식 2](상기 화학식 2에서,L1 내지 L3는 서로 독립적으로 수소, 중수소, 할로겐, 시아노, C1-C18 직쇄 또는 측쇄 알킬, C1-C18 직쇄 또는 측쇄 알콕시, C6-C18 아릴, C3-C18 시클로알킬, C4-C18 헤테로아릴 또는 5원 내지 6원의 헤테로시클로알킬이고, 이때, 상기 알킬 또는 알콕시는 비치환 또는 할로겐으로 치환되고, 상기 아릴, 시클로알킬, 헤테로아릴 또는 헤테로시클로알킬은 비치환 또는 할로겐 또는 C1-C18 직쇄 또는 측쇄 알킬로 치환되고, 상기 헤테로아릴 또는 헤테로시클로알킬은 고리 내 N, O 및 S로부터 선택되는 하나 이상의 원자를 포함한다).
- 제2항에 있어서, 상기 L1 내지 L3는 서로 독립적으로 메틸, 에틸, 프로필, 이소프로필, 시클로헥실, 페닐인 것을 특징으로 하는 유기금속 화합물.
- 제1항 또는 제2항에 있어서, 상기 R5 내지 R8는 서로 독립적으로 수소, 메틸, 페닐, 메틸페닐. 디메틸페닐인 것을 특징으로 하는 유기금속 화합물.
- 제1항 또는 제2항에 있어서, 상기 A 및 B는 각각 독립적으로 N(질소), O(산소), S(황), P(인) 및 C(탄소)로 이루어지는 군으로부터 선택되는 1종인 것을 특징으로 하는 유기금속 화합물.
- 제1항 또는 제2항의 유기금속 화합물을 포함하는 유기 발광 소자.
- 제8항에 있어서, 상기 유기금속 화합물은 발광층의 도판트 물질로 사용되는 것을 특징으로 하는 유기 발광 소자.
- 제1전극;제2전극; 및상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 발광 소자에 있어서,상기 유기물층은 제1항 또는 제2항의 유기금속 화합물을 하나 이상 포함하는 것을 특징으로 하는 유기 발광 소자.
- 제1항 또는 제2항의 유기금속 화합물을 유기용매에 용해시켜 용액을 제조하는 단계(단계 1); 및상기 단계 1의 용액을 기판 위에 떨어뜨리고 기판을 회전시킨 후, 건조하여 기판상에 박막을 형성시키는 단계(단계 2)를 포함하는 유기 발광 소자용 박막 형성 방법.
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US14/002,598 US9478756B2 (en) | 2011-04-06 | 2012-04-06 | Organometallic compound, and organic light-emitting diode using same |
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