WO2015056993A1 - Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same - Google Patents
Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- WO2015056993A1 WO2015056993A1 PCT/KR2014/009734 KR2014009734W WO2015056993A1 WO 2015056993 A1 WO2015056993 A1 WO 2015056993A1 KR 2014009734 W KR2014009734 W KR 2014009734W WO 2015056993 A1 WO2015056993 A1 WO 2015056993A1
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- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- membered
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 164
- 239000002019 doping agent Substances 0.000 title claims abstract description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000005104 aryl silyl group Chemical group 0.000 claims description 24
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000001769 aryl amino group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 5
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 63
- 239000000463 material Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- -1 phenylnaphthyl Chemical group 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 0 *I([n](c1c2C=C=C1)c1c2c(*CCC(C(C=CC2)=C2*2)=C2C=*)ccc1)I Chemical compound *I([n](c1c2C=C=C1)c1c2c(*CCC(C(C=CC2)=C2*2)=C2C=*)ccc1)I 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- MOSQXYPUMBJMRR-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cnc1-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)cnc1-c1ccccc1 MOSQXYPUMBJMRR-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 2
- 229910009112 xH2O Inorganic materials 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
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical compound CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- JNIGFUXIZVCEED-UHFFFAOYSA-N 3-(9h-carbazol-2-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C(C5=CC=CC=C5N4)=CC=3)C=C2C2=CC=CC=C21 JNIGFUXIZVCEED-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- QKVWPNRUXZYLQV-UHFFFAOYSA-N 4-(3-triphenylen-2-ylphenyl)dibenzothiophene Chemical compound C1=CC=C2C3=CC(C=4C=CC=C(C=4)C4=C5SC=6C(C5=CC=C4)=CC=CC=6)=CC=C3C3=CC=CC=C3C2=C1 QKVWPNRUXZYLQV-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
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- NXTRQJAJPCXJPY-UHFFFAOYSA-N 910058-11-6 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 NXTRQJAJPCXJPY-UHFFFAOYSA-N 0.000 description 1
- PYFSDOUOVKPHGN-UHFFFAOYSA-N CC(C)c(cccc1)c1-c1nc(C)ccc1 Chemical compound CC(C)c(cccc1)c1-c1nc(C)ccc1 PYFSDOUOVKPHGN-UHFFFAOYSA-N 0.000 description 1
- ANIXBLXVDVBTKG-UHFFFAOYSA-N CC(C=C1)=CNC1c1c(C)cc2[s]c3ccccc3c2c1 Chemical compound CC(C=C1)=CNC1c1c(C)cc2[s]c3ccccc3c2c1 ANIXBLXVDVBTKG-UHFFFAOYSA-N 0.000 description 1
- UEYFAFSFPBEVAY-UHFFFAOYSA-N CCc1cc(-c2ccccc2)ncc1-c1ccccc1 Chemical compound CCc1cc(-c2ccccc2)ncc1-c1ccccc1 UEYFAFSFPBEVAY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BXSUGBRIVIARRL-UHFFFAOYSA-N Cc(cc1[s]c2ccccc2c1c1)c1-c1ccccn1 Chemical compound Cc(cc1[s]c2ccccc2c1c1)c1-c1ccccn1 BXSUGBRIVIARRL-UHFFFAOYSA-N 0.000 description 1
- LSWJXYFQAVUJLZ-UHFFFAOYSA-N Cc1cc(-c2ccc3[s]c4ccccc4c3c2)ncc1 Chemical compound Cc1cc(-c2ccc3[s]c4ccccc4c3c2)ncc1 LSWJXYFQAVUJLZ-UHFFFAOYSA-N 0.000 description 1
- YHQCNNMCDMYPIA-UHFFFAOYSA-N Cc1cc(-c2ccccc2)ncc1-c1ccccc1 Chemical compound Cc1cc(-c2ccccc2)ncc1-c1ccccc1 YHQCNNMCDMYPIA-UHFFFAOYSA-N 0.000 description 1
- FSKRYLOXKLKTEJ-UHFFFAOYSA-N Cc1ccnc(-c2c(C)cc3[s]c4ccccc4c3c2)c1 Chemical compound Cc1ccnc(-c2c(C)cc3[s]c4ccccc4c3c2)c1 FSKRYLOXKLKTEJ-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- IAKAEIGQEHNAJA-UHFFFAOYSA-L [Ag+2].FC(F)F.[O-]S([O-])(=O)=O Chemical compound [Ag+2].FC(F)F.[O-]S([O-])(=O)=O IAKAEIGQEHNAJA-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 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
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- 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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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Definitions
- the present disclosure relates to a combination of a host compound and a dopant compound, and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
- the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
- Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
- the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
- the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
- the light-emitting layer formed by the light-emitting material needs to be uniform and stable.
- the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein.
- the light-emitting materials can be classified as a host material and a dopant material.
- devices showing the best electroluminescent characteristics comprise a light-emitting layer in which a dopant is doped into a host, in general. Furthermore, depending on the excited state, the light-emitting material can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials have been widely used for the organic EL device. However, since phosphorescent materials enhance luminous efficiency for converting electricity to light by four (4) times compared to fluorescent materials and can reduce power consumption to have longer lifespan, development of phosphorescent light-emitting materials are widely being researched.
- Iridium(III) complexes have been widely known as phosphorescent dopant materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ), and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- BCP bathocuproine
- BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
- phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [( ⁇ /voltage) ⁇ current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent host materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required to be improved.
- Korean Patent Application Laying-open No. 10-2011-0130475 discloses iridium complexes for being used as a dopant compound of an organic electroluminescent device, and compounds having triphenylene moiety and dibenzothiophene moiety as a host compound suitable for being combined with the iridium complexes.
- Korean Patent Application Laying-open No. 10-2011-0015836 discloses organic electroluminescent compounds having a carbazole moiety, and a combination of said compound and Ir(ppy) 3 or (piq) 2 Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate].
- the conventional combination of a dopant compound and a host compound is applied to an organic electroluminescent device, the characteristics such as a driving voltage, luminous efficiency, and power efficiency are not satisfactory.
- the present inventors found that when using a combination of a specific iridium complex and a specific carbazole-containing compound as a light-emitting material, it is possible to produce an organic electroluminescent device showing excellence in luminous and power efficiencies at a low driving voltage.
- the objective of the present disclosure is to provide a combination of a dopant compound and a host compound, which can provide excellent luminous and power efficiencies, long lifespan, and a lowered driving voltage; and an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage by comprising the combination.
- the present inventors found that the above objective can be achieved by a combination of one or more dopant compounds represented by the following formula 1 and one or more host compounds represented by the following formula 2, and an organic electroluminescent device comprising the same.
- L 1 to L 3 are selected from the following structures A-1 to A-5, with the proviso that at least one of L 1 to L 3 is represented by A-1, A-2 or A-3:
- X represents O or S
- R 1 to R 11 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and
- a to h each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , or R 8 may be the same or different,
- Y 1 represents O, S, -NR 31 or -CR 32 R 33 ;
- L 4 and L 5 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
- R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubsti
- Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
- R 31 to R 33 each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- o and p each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R 21 or R 22 may be the same or different;
- q and r each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R 23 or R 24 may be the same or different; and
- the combination of a dopant compound and a host compound of the present disclosure can provide an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage.
- the present disclosure relates to a combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2, and an organic electroluminescent device comprising the same.
- the dopant compound represented by formula 1 will be described in detail.
- the one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
- R 1 to R 6 , a to f, X, L 2 , and L 3 are as defined in formula 1 above.
- L 2 and L 3 each independently, may represent the structure selected from A-1, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-1, A-4, and A-5; or one of L 2 and L 3 may have the structure A-1, and the other may have the structure A-4 or A-5.
- L 2 and L 3 each independently, may be selected from A-2, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-2, A-4, and A-5; or one of L 2 and L 3 may have the structure A-2, and the other may have the structure A-4 or A-5.
- L 2 and L 3 each independently, may be selected from A-3, A-4, and A-5. More preferably, both L 2 and L 3 may have the same structure which is selected from A-3, A-4, and A-5; or one of L 2 and L 3 may have the structure A-3, and the other may have the structure A-4 or A-5.
- the dopant compound represented by formula 1 may be represented by formula 3.
- R 1 to R 11 each independently, may represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
- R 1 to R 8 each independently, may represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C6-C18)aryl, or a (6- to 18-membered)heteroaryl; and R 9 to R 11 , each independently, may represent hydrogen or a (C1-C10)alkyl.
- a to h each independently, are an integer of 0 to 2.
- the compound of formula 3 includes the following, but is not limited thereto:
- the compound of formula 4 includes the following, but is not limited thereto:
- the compound of formula 5 includes the following, but is not limited thereto:
- the compounds of formula 1 including the compounds of formulae 3 to 5 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0130476.
- the host compound represented by formula 2 will be described in detail.
- the one or more host compounds represented by formula 2 may be one or more of the compounds represented by the following formulae 6 to 12:
- R 21 to R 24 , Y 1 , L 4 , L 5 , Ar 1 , o, p, q, and r are as defined above.
- the one or more host compounds represented by formula 2 may be one or more of the compounds represented by formulae 6, 9, and 10.
- L 4 and L 5 each independently, may represent, preferably, a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, a single bond, or a substituted or unsubstituted (C6-C18)aryl.
- L 4 and L 5 each independently, may represent a single bond, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
- R 21 to R 24 each independently, may represent, preferably, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
- Y 1 may represent preferably, O, S or -NR 31 .
- R 31 may represent preferably, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl; and more preferably, a substituted or unsubstituted (C6-C18)aryl.
- R 31 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted phenylnaphthyl, or a substituted or unsubstituted naphthylphenyl.
- Ar 1 may represent preferably, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing one(1) to three(3) nitrogens as the hetero atom.
- the substituents of the substituted aryl and the substituted heteroaryl of Ar 1 may be one or more selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
- Ar 1 may be selected from the following structures B-1 to B-7:
- A represents at least one selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl,
- A may represent at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen, a (C1-C10) alkyl, or a (6- to 13-membered)heteroaryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C10)alkyl; a tri(C6-C20)arylsilyl; a di(C1-C10)alkyl(C6-C20)arylsilyl; a (C1-C10)alkyldi(C6-C20)arylsilyl; a mono- or di-(C6-C20)arylamino; and a (C1-C10)alkyl(C6-C20)arylamino
- the compounds of formulae 6 to 12 include the following, but are not limited thereto:
- the compounds of formula 2 including the compounds of formulae 6 to 12 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0015836.
- (C1-C30)alkyl indicates a linear or branched alkyl(ene) having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (C6-C30)aryl indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 18 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, indanyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- “Substituted” in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
- the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino of R 1 to R 7 , R 21 to R 24 , R 31 to R 33 , L 1 , L 2 , and Ar 1 of formulae 1 and 2, each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl unsubstit
- the organic electroluminescent device comprising the combination of the dopant compound of formula 1 and the host compound of formula 2 will be described in detail.
- the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- One of the first and second electrodes may be an anode and the other may be a cathode.
- the organic layer may comprise a light-emitting layer, and the light-emitting layer may comprise the combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2.
- the light-emitting layer may be a single layer or a multiple layer in which two or more layers are laminated.
- a doping amount of the dopant compound is less than 20 wt%, preferably less than 17 wt% based on the total amount of the host compound and the dopant compound, in view of color purity, luminous efficiency, power efficiency, and a driving voltage.
- the light-emitting layer may further comprise one or more materials, for example, an additional second host material, other than the combination of the compound of formula 1 and the compound of formula 2.
- the organic layer may further comprise one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
- the present disclosure provides a material for preparing an organic electroluminescent device, and an organic electroluminescent device comprising the material.
- the material may comprise one or more dopant compounds of formula 1 to be combined with one or more host compounds of formula 2.
- the material may comprise one or more host compounds of formula 2 to be combined with one or more dopant compounds of formula 1.
- the material may further comprise a conventional compound(s) which has been comprised for preparing an organic electroluminescent device.
- the material may be a composition or a mixture.
- the present disclosure provides an organic layer comprising one or more dopant compounds of formula 1 and one or more host compounds of formula 2.
- the organic layer may comprise two or more layers, wherein the dopant compound and the host compound may be comprised in a layer at the same time, or they may be comprised in two different layers, respectively.
- the present disclosure provides an organic electroluminescent device comprising the organic layer.
- the organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise, in addition to the combination of the present disclosure, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
- at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
- a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
- a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds
- the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
- each layer of the organic electroluminescent device of the present disclosure dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
- a layer comprising the compound of formula 1 and the compound of formula 2 can be formed by co-evaporation.
- An OLED was produced using the combination according to the present disclosure.
- a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Samsung Corning) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
- the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
- N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material above, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was then introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-19 was introduced into one cell of the vacuum vapor depositing apparatus, as a host compound, and compound D-2 was introduced into another cell as a dopant compound.
- the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- 2-(4-(9,10-di(naphthalen-2-yl) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
- the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- An OLED was produced. All the material used for producing the OLED were those purified by vacuum sublimation at 10 -6 torr. The produced OLED showed green emission having a luminance of 2,430 cd/m 2 and a power efficiency of 36.6 lm/W at 3.4 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 3,440 cd/m 2 and a power efficiency of 43.2 lm/W at 3.0 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-93 and compound D-2 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 1,210 cd/m 2 and a power efficiency of 25.7 lm/W at 3.1 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 3,840 cd/m 2 and a power efficiency of 60.6 lm/W at 2.7 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-2 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 930 cd/m 2 and a power efficiency of 42.3 lm/W at 3.2 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-96 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 1,210 cd/m 2 and a power efficiency of 55.5 lm/W at 2.6 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-73 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 2,960 cd/m 2 and a power efficiency of 42.2 lm/W at 2.6 V.
- An OLED was produced in the same manner as in Device Example 1, except for using compound H-6 and compound D-3 as the host compound and the dopant compound for the light-emitting layer.
- the produced OLED showed green emission having a luminance of 1,020 cd/m 2 and a power efficiency of 56.5 lm/W at 2.8 V.
- An OLED was produced in the same manner as in Device Example 1, except that comparative compound 1 shown below and compound D-2 were used as a host compound and a dopant compound to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene was deposited to form a hole blocking layer having a thickness of 10 nm.
- the produced OLED showed green emission having a luminance of 3,000 cd/m 2 and a power efficiency of 16.81 lm/W at 6.9 V.
- the Device Examples confirm that the combination of the present disclosure provides better luminous characteristics than the conventional materials.
- the organic electroluminescent device can show excellent luminous characteristics and lowered driving voltage, thereby improving power efficiency to reduce power consumption.
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Abstract
The present disclosure relates to a specific combination of a dopant compound and a host compound, and an organic electroluminescent device comprising the combination. By comprising the combination of the present disclosure, the organic electroluminescent device showing excellence in luminous efficiency, power efficiency, and color purity, low driving voltage, and good lifespan can be provided.
Description
The present disclosure relates to a combination of a host compound and a dopant compound, and an organic electroluminescent device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
Generally, an organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer. Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in the organic EL device is light-emitting materials. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. Depending on colors visualized by light-emission, the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Depending on its function, the light-emitting materials can be classified as a host material and a dopant material. It is known that devices showing the best electroluminescent characteristics comprise a light-emitting layer in which a dopant is doped into a host, in general. Furthermore, depending on the excited state, the light-emitting material can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials have been widely used for the organic EL device. However, since phosphorescent materials enhance luminous efficiency for converting electricity to light by four (4) times compared to fluorescent materials and can reduce power consumption to have longer lifespan, development of phosphorescent light-emitting materials are widely being researched.
Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, materials showing better characteristics than conventional ones must be urgently developed.
Iridium(III) complexes have been widely known as phosphorescent dopant materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
The host materials influence the efficiency and performance of the EL device, and thus their selection is important. At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al., developed a high performance organic EL device using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) etc., as host materials, which were known as hole blocking materials.
Although these phosphorescent host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent host materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required to be improved.
Korean Patent Application Laying-open No. 10-2011-0130475 discloses iridium complexes for being used as a dopant compound of an organic electroluminescent device, and compounds having triphenylene moiety and dibenzothiophene moiety as a host compound suitable for being combined with the iridium complexes. Korean Patent Application Laying-open No. 10-2011-0015836 discloses organic electroluminescent compounds having a carbazole moiety, and a combination of said compound and Ir(ppy)3 or (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate]. However, where the conventional combination of a dopant compound and a host compound is applied to an organic electroluminescent device, the characteristics such as a driving voltage, luminous efficiency, and power efficiency are not satisfactory.
The present inventors found that when using a combination of a specific iridium complex and a specific carbazole-containing compound as a light-emitting material, it is possible to produce an organic electroluminescent device showing excellence in luminous and power efficiencies at a low driving voltage.
The objective of the present disclosure is to provide a combination of a dopant compound and a host compound, which can provide excellent luminous and power efficiencies, long lifespan, and a lowered driving voltage; and an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage by comprising the combination.
The present inventors found that the above objective can be achieved by a combination of one or more dopant compounds represented by the following formula 1 and one or more host compounds represented by the following formula 2, and an organic electroluminescent device comprising the same.
wherein L1 to L3, each independently, are selected from the following structures A-1 to A-5, with the proviso that at least one of L1 to L3 is represented by A-1, A-2 or A-3:
X represents O or S;
R1 to R11, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and
a to h, each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R1, R2, R3, R4, R5, R6, R7, or R8 may be the same or different,
wherein Y1 represents O, S, -NR31 or -CR32R33;
L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
R21 to R24, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
R31 to R33, each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
o and p, each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R21 or R22 may be the same or different;
q and r, each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R23 or R24 may be the same or different; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, P(=O), Si, and P.
The combination of a dopant compound and a host compound of the present disclosure, can provide an organic electroluminescent device showing long lifespan, excellent luminous and power efficiencies, and a low driving voltage.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present disclosure relates to a combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2, and an organic electroluminescent device comprising the same.
The dopant compound represented by formula 1 will be described in detail.
The one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
wherein, R1 to R6, a to f, X, L2, and L3 are as defined in formula 1 above.
In formula 3, preferably, L2 and L3, each independently, may represent the structure selected from A-1, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-1, A-4, and A-5; or one of L2 and L3 may have the structure A-1, and the other may have the structure A-4 or A-5.
In formula 4, preferably, L2 and L3, each independently, may be selected from A-2, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-2, A-4, and A-5; or one of L2 and L3 may have the structure A-2, and the other may have the structure A-4 or A-5.
In formula 5, preferably, L2 and L3, each independently, may be selected from A-3, A-4, and A-5. More preferably, both L2 and L3 may have the same structure which is selected from A-3, A-4, and A-5; or one of L2 and L3 may have the structure A-3, and the other may have the structure A-4 or A-5.
Preferably, the dopant compound represented by formula 1 may be represented by formula 3.
In formulae 1 and 3 to 5, preferably, R1 to R11, each independently, may represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl. More preferably, R1 to R8, each independently, may represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C6-C18)aryl, or a (6- to 18-membered)heteroaryl; and R9 to R11, each independently, may represent hydrogen or a (C1-C10)alkyl. Preferably, a to h, each independently, are an integer of 0 to 2.
More specifically, the compound of formula 3 includes the following, but is not limited thereto:
More specifically, the compound of formula 4 includes the following, but is not limited thereto:
More specifically, the compound of formula 5 includes the following, but is not limited thereto:
The compounds of formula 1 including the compounds of formulae 3 to 5 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0130476.
The host compound represented by formula 2 will be described in detail.
The one or more host compounds represented by formula 2 may be one or more of the compounds represented by the following formulae 6 to 12:
wherein, R21 to R24, Y1, L4, L5, Ar1, o, p, q, and r are as defined above.
Preferably, the one or more host compounds represented by formula 2 may be one or more of the compounds represented by formulae 6, 9, and 10.
In formulae 2 or 6 to 12, L4 and L5, each independently, may represent, preferably, a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, a single bond, or a substituted or unsubstituted (C6-C18)aryl. Specifically, L4 and L5, each independently, may represent a single bond, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
R21 to R24, each independently, may represent, preferably, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
Y1 may represent preferably, O, S or -NR31. R31 may represent preferably, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl; and more preferably, a substituted or unsubstituted (C6-C18)aryl. Specifically, R31 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted phenylnaphthyl, or a substituted or unsubstituted naphthylphenyl.
Ar1 may represent preferably, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing one(1) to three(3) nitrogens as the hetero atom. The substituents of the substituted aryl and the substituted heteroaryl of Ar1, each independently, may be one or more selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
Preferably, Ar1 may be selected from the following structures B-1 to B-7:
wherein, A represents at least one selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy; m represents an integer of 0 to 4; where m is 2 or more, each of A may be the same or different; and * represents a bonding site. Preferably, A may represent at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen, a (C1-C10) alkyl, or a (6- to 13-membered)heteroaryl; a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, or a (C6-C13)aryl unsubstituted or substituted with a (C1-C10)alkyl; a tri(C6-C20)arylsilyl; a di(C1-C10)alkyl(C6-C20)arylsilyl; a (C1-C10)alkyldi(C6-C20)arylsilyl; a mono- or di-(C6-C20)arylamino; and a (C1-C10)alkyl(C6-C20)arylamino. Preferably, m may represent an integer of 0 to 2; or may represent 0 or 1.
More specifically, the compounds of formulae 6 to 12 include the following, but are not limited thereto:
The compounds of formula 2 including the compounds of formulae 6 to 12 can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the methods disclosed in Korean Patent Application Laying-Open No. 10-2011-0015836.
Herein, “(C1-C30)alkyl” indicates a linear or branched alkyl(ene) having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. “(C2-C30)alkynyl” indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “(5- to 7-membered) heterocycloalkyl” indicates a cycloalkyl having 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, P(=O), Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “(C6-C30)aryl” indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 18 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, indanyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “(5- to 30-membered) heteroaryl” indicates an aryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 15 ring backbone atoms including at least one, preferably 1 to 4, hetero atom selected from the group consisting of B, N, O, S, P(=O), Si, and P; may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br, and I.
“Substituted” in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent. The substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino of R1 to R7, R21 to R24, R31 to R33, L1, L2, and Ar1 of formulae 1 and 2, each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl, a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C1-C30)alkyl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy.
The organic electroluminescent device comprising the combination of the dopant compound of formula 1 and the host compound of formula 2 will be described in detail.
The organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. One of the first and second electrodes may be an anode and the other may be a cathode.
The organic layer may comprise a light-emitting layer, and the light-emitting layer may comprise the combination of one or more dopant compounds represented by formula 1 and one or more host compounds represented by formula 2. The light-emitting layer may be a single layer or a multiple layer in which two or more layers are laminated. Regarding the combination ratio between the dopant compound and the host compound in the light-emitting layer, it is preferable that a doping amount of the dopant compound is less than 20 wt%, preferably less than 17 wt% based on the total amount of the host compound and the dopant compound, in view of color purity, luminous efficiency, power efficiency, and a driving voltage. The light-emitting layer may further comprise one or more materials, for example, an additional second host material, other than the combination of the compound of formula 1 and the compound of formula 2. The organic layer may further comprise one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
According to another aspect of the present disclosure, the present disclosure provides a material for preparing an organic electroluminescent device, and an organic electroluminescent device comprising the material. The material may comprise one or more dopant compounds of formula 1 to be combined with one or more host compounds of formula 2. The material may comprise one or more host compounds of formula 2 to be combined with one or more dopant compounds of formula 1. The material may further comprise a conventional compound(s) which has been comprised for preparing an organic electroluminescent device. The material may be a composition or a mixture.
According to another aspect of the present disclosure, the present disclosure provides an organic layer comprising one or more dopant compounds of formula 1 and one or more host compounds of formula 2. The organic layer may comprise two or more layers, wherein the dopant compound and the host compound may be comprised in a layer at the same time, or they may be comprised in two different layers, respectively. The present disclosure provides an organic electroluminescent device comprising the organic layer.
The organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. In the organic electroluminescent device of the present disclosure, the organic layer may further comprise, in addition to the combination of the present disclosure, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
In addition, the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the combination of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "a surface layer”) may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used. For example, a layer comprising the compound of formula 1 and the compound of formula 2 can be formed by co-evaporation.
Hereinafter, the compound of the present disclosure, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
Example 1: Preparation of compound D-2
Preparation
of
compound
1-1
After mixing 2-phenylpyridine (10g, 32mmol), iridium(III) chloride hydrate (IrCl3
·xH2O) (8.1g, 29mmol), 2-ethoxy ethanol (220mL) and H2O (74mL), the mixture was stirred at 140°C for 24 hours. After the reaction, the mixture was cooled to room temperature, washed with water and methanol (MeOH), and then dried to obtain compound 1-1 (11g, 71%).
Preparation of compound
1-2
After dissolving compound 1-1 (10g, 9 mmol) in methylene chloride (MC) 4L, silver trifluoromethane sulfate (AgOTf) (5g, 19mmol) dissolved in methanol (MeOH) (400 mL) was added slowly thereto. The mixture was stirred for 12 hours at room temperature. After the reaction, the reaction mixture was filtered. The filtrate was dried to obtain compound 1-2 (12g, 94%).
Preparation of compound
1-3
After mixing 2-bromopyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (16g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150 mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and then distilled under reduced pressure. The resultant was subjected to column chromatography with methylene chloride (MC) / hexane (Hx) = 1/3 to obtain compound 1-3 (10g, 63%, white solid).
Preparation of compound
D-2
After adding compound 1-3 (7g, 28mmol) and compound 1-2 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and then, subjected to column chromatography with chloroform (CHCl3) to obtain compound D-2 (2g, 17%).
Melting Point (mp) 400℃ or more, UV 292nm, PL 525nm, LC 99.06%
Example 2: Preparation of compound D-3
Preparation
of
compound
2-1
After mixing 2-bromo-5-methylpyridine (15g, 87mmol), phenylboronic acid (14g, 114mmol), Pd(PPh3)4 (3g, 2.6mmol), Na2CO3 (36g, 260mmol), toluene (300mL), EtOH (150mL) and H2O (130mL), the mixture was stirred at 100°C for 3 hours. After the reaction, the mixture was extracted with EA, dried with MgSO4, and distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/2 to obtain compound 2-1 (10g, 68%, white solid).
Preparation of compound
2-2
After mixing compound 2-1 (10g, 30mmol), IrCl3·xH2O (8g, 27mmol), 2-ethoxy ethanol (200mL) and H2O (70mL), the mixture was stirred at 140°C for 24 hours. After the reaction, the mixture was cooled to room temperature, washed with H2O and MeOH, and dried to obtain compound 2-2 (11g, 75%).
Preparation of compound
2-3
After dissolving compound 2-2 (11g, 10mmol) in MC 4L, AgOTf (5g, 20mmol) dissolved in MeOH (400mL) was added slowly thereto. The mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was filtered. The filtrate was dried to obtain compound 2-3 (13g, 89%).
Preparation of compound
D-3
After adding compound 1-3 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with CHCl3 to obtain compound D-3 (3.5g, 33%).
mp 400℃ or more, UV 292nm, PL 527nm, LC 99.19%
Example 3: Preparation of compound D-95
Preparation of compound 3-1
After mixing 2-bromo-4-methylpyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (15g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and then distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/3 to obtain compound 3-1 (11g, 67%, white solid).
Preparation of compound
D-95
After adding compound 3-1 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with chloroform (CHCl3) to obtain compound D-95 (1.5g, 15%).
mp 400℃ or more, UV 292nm, PL 519nm, LC 99.12%
Example 4: Preparation of compound D-96
Preparation
of
compound
4-1
After mixing 2-bromo-5-methylpyridine (10g, 63mmol), dibenzo[b,d]furan-4-yl boronic acid (15g, 76mmol), palladium(0) tetrakis(triphenylphosphine) [Pd(PPh3)4] (2.2g, 2mmol), Na2CO3 (20g, 19mmol), toluene (300mL), ethanol (EtOH) (150mL) and H2O (10mL), the mixture was stirred at 100°C for 2 hours. After the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), dried with MgSO4, and distilled under reduced pressure. The resultant was subjected to column chromatography with MC/Hx = 1/3 to obtain compound 4-1 (13g, 80%, white solid).
Preparation of compound
D-96
After adding compound 4-1 (7g, 28mmol) and compound 2-3 (10g, 14mmol) to MeOH (200mL), the mixture was stirred under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and subjected to column chromatography with chloroform (CHCl3) to obtain compound D-96 (3.0g, 30%).
mp 390℃, UV 290nm, PL 521nm, LC 96.31%
Example 5: Preparation of compound H-1
After dissolving 9-phenyl-9H,9'H-3,3'-bicarbazole (10g, 22.4mmol) in dimethylformamide (DMF) (150mL) in a flask, NaH (1.3g, 33.6mmol) was added thereto. After 30 minutes, 2-chloro-4,6-diphenyl-1,3,5-triazine (5g, 18.6mmol) was added to the mixture. The mixture was stirred at room temperature for 4 hours, and methanol was added thereto. The obtained solids were filtered under reduced pressure, and then subjected to column chromatography to obtain compound H-1 (6.5g, 54%).
Example 6: Preparation of compound H-19
After introducing 9-phenyl-9H,9'H-3,3'-bicarbazole (36.2g, 93.2mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (40g, 97.9mmol), Pd(OAc)2 (1.25g, 5.59mmol), 2-dicyclohexylphosphino-2'-6'-dimethoxybiphenyl(S-Phos) (4.6g, 11.18mmol), NaO(t-butyl) (26.8g, 279.7mmol) and o-xylene (450mL) into a flask, the mixture was stirred under reflux. After 6 hours, the mixture was cooled to room temperature. The obtained solids were filtered under reduced pressure, and subjected to column chromatography to obtain compound H-19 (34.8g, 52.1%).
Example 7: Preparation of compound H-25
Compound H-25 (9.5g, 86%) was obtained in the same manner as in the preparation of compound H-1, by using 9'-phenyl-9H,9'H-2,3'-bicarbazole (7g, 17.14mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1g, 18.85mmol).
Data of the prepared host compounds above, and other host compounds which can be prepared in the manner of the Examples above are shown in Table 1 below.
[Table 1]
Device Example 1: Production of an OLED using the present combination
An OLED was produced using the combination according to the present disclosure. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) (Samsung Corning) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material above, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was then introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-19 was introduced into one cell of the vacuum vapor depositing apparatus, as a host compound, and compound D-2 was introduced into another cell as a dopant compound. The two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. 2-(4-(9,10-di(naphthalen-2-yl) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED was produced. All the material used for producing the OLED were those purified by vacuum sublimation at 10-6 torr. The produced OLED showed green emission having a luminance of 2,430 cd/m2 and a power efficiency of 36.6 lm/W at 3.4 V.
[Device Example 2] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 3,440 cd/m2 and a power efficiency of 43.2 lm/W at 3.0 V.
[Device Example 3] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-93 and compound D-2 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,210 cd/m2 and a power efficiency of 25.7 lm/W at 3.1 V.
[Device Example 4] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 3,840 cd/m2 and a power efficiency of 60.6 lm/W at 2.7 V.
[Device Example 5] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-49 and compound D-2 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 930 cd/m2 and a power efficiency of 42.3 lm/W at 3.2 V.
[Device Example 6] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-19 and compound D-96 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,210 cd/m2 and a power efficiency of 55.5 lm/W at 2.6 V.
[Device Example 7] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-73 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 2,960 cd/m2 and a power efficiency of 42.2 lm/W at 2.6 V.
[Device Example 8] Production of an OLED using the present combination
An OLED was produced in the same manner as in Device Example 1, except for using compound H-6 and compound D-3 as the host compound and the dopant compound for the light-emitting layer. The produced OLED showed green emission having a luminance of 1,020 cd/m2 and a power efficiency of 56.5 lm/W at 2.8 V.
[Comparative Device Example 1] Production of an OLED using a conventional combination
An OLED was produced in the same manner as in Device Example 1, except that comparative compound 1 shown below and compound D-2 were used as a host compound and a dopant compound to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene was deposited to form a hole blocking layer having a thickness of 10 nm. The produced OLED showed green emission having a luminance of 3,000 cd/m2 and a power efficiency of 16.81 lm/W at 6.9 V.
The Device Examples confirm that the combination of the present disclosure provides better luminous characteristics than the conventional materials. By using the combination of the present disclosure, the organic electroluminescent device can show excellent luminous characteristics and lowered driving voltage, thereby improving power efficiency to reduce power consumption.
Claims (11)
- A combination of one or more dopant compounds represented by the following formula 1, and one or more host compounds represented by the following formula 2:
whereinL1 to L3, each independently, are selected from the following structures A-1 to A-5, with the proviso that at least one of L1 to L3 is represented by A-1, A-2 or A-3:
X represents O or S;R1 to R11, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; anda to h, each independently, represent an integer of 0 to 4; where a, b, c, d, e, f, g, or h is an integer of 2 or more, each of R1, R2, R3, R4, R5, R6, R7, or R8 may be the same or different,
whereinY1 represents O, S, -NR31 or -CR32R33;L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;R21 to R24, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;R31 to R33, each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;o and p, each independently, represent an integer of 0 to 4; where o or p is an integer of 2 or more, each of R21 or R22 may be the same or different;q and r, each independently, represent an integer of 0 to 3; where q or r is an integer of 2 or more, each of R23 or R24 may be the same or different; andthe heteroaryl contains at least one hetero atom selected from B, N, O, S, P(=O), Si, and P. - The combination according to claim 1, wherein, in formulae 1 and 2, the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C6-C30)aryl, the substituted (5- to 30-membered)heteroaryl, the substituted silyl and the substituted amino in R1 to R11, R21 to R24, R31 to R33, L4, L5, and Ar1, each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubsituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl, a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C1-C30)alkyl, a (C3-C30)cycloalkyl, a (5- to 7-membered)heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a mono- or di-(C1-C30)alkylamino, a mono- or di-(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a carboxy, a nitro, and a hydroxy.
- The combination according to claim 1, wherein the one or more dopant compounds represented by formula 1 is one or more of the compounds represented by the following formulae 3 to 5:
whereinR1 to R6, a to f, X, L2, and L3 are as defined in claim 1. - The combination according to claim 1, wherein, R1 to R11, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C3-C10)cycloalkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
- The combination according to claim 3, wherein the dopant compound represented by formula 3 is selected from the following:
- The combination according to claim 3, wherein the dopant compound represented by formula 4 is selected from the following:
- The combination according to claim 3, wherein the dopant compound represented by formula 5 is selected from the following:
- The combination according to claim 1, wherein the one or more host compounds represented by formula 2 is one or more of the compounds represented by the following formulae 6 to 12:
whereinR21 to R24, Y1, L1, L2, Ar1, o, p, q, and r are as defined in claim 1. - The combination according to claim 1, wherein, in formula 2, L4 and L5, each independently, represent a single bond, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;R21 to R24, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;Y1 represents O, S or -NR31;R31 represents a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C20)aryl;Ar1 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl containing 1 to 3 of nitrogen as the hetero atom; andthe substituents of the substituted aryl and the substituted heteroaryl of Ar1, each independently, are at least one selected from the group consisting of a (C6-C20)aryl unsubstituted or substituted with a halogen or a (C1-C10)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a tri(C6-C20)arylsilyl, a di(C1-C10)alkyl(C6-C20)arylsilyl, a (C1-C10)alkyldi(C6-C20)arylsilyl, a mono- or di-(C6-C20)arylamino, and a (C1-C10)alkyl(C6-C20)arylamino.
- The combination according to claim 8, wherein the host compounds represented by formulae 6 to 12 are selected from the following:
- The organic electroluminescent device comprising the combination according to claim 1.
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| JP2022153359A (en) * | 2017-03-29 | 2022-10-12 | ユニバーサル ディスプレイ コーポレイション | Organic electroluminescent materials and devices |
| US11725021B2 (en) | 2017-03-29 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP7382704B2 (en) | 2017-03-29 | 2023-11-17 | ユニバーサル ディスプレイ コーポレイション | Organic electroluminescent materials and devices |
| JP7450667B2 (en) | 2017-03-29 | 2024-03-15 | ユニバーサル ディスプレイ コーポレイション | Organic electroluminescent materials and devices |
| EP3730506A1 (en) * | 2017-03-29 | 2020-10-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11621397B2 (en) | 2018-01-17 | 2023-04-04 | Lg Chem, Ltd. | Iridium complexes containing a ligand including a (dibenzo [B,D] furanyl) pyridine skeleton having deuterium substitutions para and meta to the N ring atom and organic light emitting device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102191108B1 (en) | 2020-12-15 |
| CN105636971A (en) | 2016-06-01 |
| TW201529589A (en) | 2015-08-01 |
| KR20150045295A (en) | 2015-04-28 |
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