WO2012039561A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- WO2012039561A1 WO2012039561A1 PCT/KR2011/006855 KR2011006855W WO2012039561A1 WO 2012039561 A1 WO2012039561 A1 WO 2012039561A1 KR 2011006855 W KR2011006855 W KR 2011006855W WO 2012039561 A1 WO2012039561 A1 WO 2012039561A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- compound
- organic electroluminescent
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 139
- -1 cyano, N-carbazolyl Chemical group 0.000 claims description 187
- 239000010410 layer Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 239000012044 organic layer Substances 0.000 claims description 37
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 29
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005580 triphenylene group Chemical group 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 238000002360 preparation method Methods 0.000 description 65
- 239000000203 mixture Substances 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000012153 distilled water Substances 0.000 description 32
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 0 CCC(NC([C@]1C=CO)C=*)=C1c([n](*)c1c2CCC=C1)c2C#C Chemical compound CCC(NC([C@]1C=CO)C=*)=C1c([n](*)c1c2CCC=C1)c2C#C 0.000 description 9
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 7
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 7
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 229940125773 compound 10 Drugs 0.000 description 4
- 229940126086 compound 21 Drugs 0.000 description 4
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-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
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 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 2
- 230000000903 blocking effect Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000003838 furazanyl group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VBJWDGGEJNGTET-UHFFFAOYSA-N 12-(4,6-diphenyl-1,3,5-triazin-2-yl)-11-phenylindolo[2,3-a]carbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(N2C3=C4N(C=5C=CC=CC=5)C5=CC=CC=C5C4=CC=C3C3=CC=CC=C32)=N1 VBJWDGGEJNGTET-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- GWWWCWGULSWMGY-UHFFFAOYSA-N Brc1cccc(-[n]2c3ccc(c4ccccc4[o]4)c4c3c3c2cccc3)c1 Chemical compound Brc1cccc(-[n]2c3ccc(c4ccccc4[o]4)c4c3c3c2cccc3)c1 GWWWCWGULSWMGY-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- LGURBQLNAWJNDU-UHFFFAOYSA-N CC(C)(c(c(-c1c2)c3)ccc3-c3ccccc3)c1cc1c2c2ccccc2[n]1-c1nc(-c(cc2)cc3c2c(cccc2)c2c2c3cccc2)ccn1 Chemical compound CC(C)(c(c(-c1c2)c3)ccc3-c3ccccc3)c1cc1c2c2ccccc2[n]1-c1nc(-c(cc2)cc3c2c(cccc2)c2c2c3cccc2)ccn1 LGURBQLNAWJNDU-UHFFFAOYSA-N 0.000 description 1
- KAXUPYUTISDQCE-UHFFFAOYSA-N CC(C1)C=Cc2c1[s]c1c2ccc2c1c(cccc1)c1[n]2-c1nc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)ccn1 Chemical compound CC(C1)C=Cc2c1[s]c1c2ccc2c1c(cccc1)c1[n]2-c1nc(-c(cc2)cc3c2c(cccc2)c2c2ccccc32)ccn1 KAXUPYUTISDQCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910004039 HBF4 Inorganic materials 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
- 150000001204 N-oxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=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
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- QXKVVKXZVVOXEN-UHFFFAOYSA-N c(cc1)cc(c2c3ccc4c2[o]c2ccccc42)c1[n]3-c1cc(-c2ccc(c3ccccc3c3ccccc33)c3c2)ccc1 Chemical compound c(cc1)cc(c2c3ccc4c2[o]c2ccccc42)c1[n]3-c1cc(-c2ccc(c3ccccc3c3ccccc33)c3c2)ccc1 QXKVVKXZVVOXEN-UHFFFAOYSA-N 0.000 description 1
- ZHUCLPQWHVIRAG-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(c(c2c3cccc2)c(cc2)[n]3-c(cc3)ccc3-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(c(c2c3cccc2)c(cc2)[n]3-c(cc3)ccc3-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)c2c2ccccc12 ZHUCLPQWHVIRAG-UHFFFAOYSA-N 0.000 description 1
- XYZGAMBQUKTSIJ-UHFFFAOYSA-N c(cc12)ccc1[nH]c(cc1)c2c2c1c(cccc1)c1[o]2 Chemical compound c(cc12)ccc1[nH]c(cc1)c2c2c1c(cccc1)c1[o]2 XYZGAMBQUKTSIJ-UHFFFAOYSA-N 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
- 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 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
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=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
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 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
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
- electroluminescent (EL) devices which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate.
- EL electroluminescent
- Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
- electroluminescent material The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material.
- fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism.
- iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
- a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
- CBP is most widely known as a host material for a phosphorescent material.
- High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported.
- High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
- KR Patent Publication No. 2010-0056490 discloses a compound for organic electroluminescent materials in which triphenylene is substituted for carbazole, dibenzofuran, dibenzothiophene, etc.
- the above-mentioned document KR2010-0056490 does not disclose a compound wherein triphenylene is linked to a 5 membered-heteroaryl group fused with the rings including benzothiophene, indole, indene and benzofuran at the carbazole.
- an object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional material.
- Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
- organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same.
- the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
- ring B represents ;
- X 1 through X 4 independently represent CR 3 or N;
- Y 1 and Y 2 independently represent a single bond, -O-, -S-, -C(R 11 )(R 12 )-, -Si(R 13 )(R 14 )- or -N(R 15 )-, except for a case where both Y 1 and Y 2 are a single bond;
- R 1 through R 3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyls, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR 16 R
- R 11 through R 22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S
- L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, substituted or unsubstituted (C3-C30)cycloalkylene, -L 2 -L 3 - or -L 3 -L 2 -;
- L 2 represents substituted or unsubstituted (C6-C30)arylene
- L 3 represents substituted or unsubstituted (C2-C30)heteroarylene
- Ar 1 and Ar 2 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
- o represents an integer of 1 to 4, and when o is an integer of 2 or greater, each of R 1 may be identical to or different from each other;
- p represents an integer of 1 or 2, and when p represents 2, each of R 2 may be identical to or different from each other;
- alkyl As described herein, “alkyl”, “alkoxy” and other substituents containing the “alkyl” moiety include both linear and branched species, and the “cycloalkyl” includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring.
- aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
- the naphthyl includes 1-naphthyl and 2-naphthyl
- the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
- the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl
- the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl.
- the pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl
- the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl
- the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl
- the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- heteroaryl includes a structure where one or more heteroaryls are linked by single bonds.
- the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
- Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazo
- the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofur
- (C1-C30)alkyl includes (C1-C20)alkyl or (C1-C10)alkyl
- (C6-C30)aryl includes (C6-C20)aryl
- (C2-C30)heteroaryl includes (C2-C20)heteroaryl
- (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
- (C2-C30)alkenyl or alkynyl includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
- each substituent of the R 1 through R 3 , L 1 , L 2 , L 3 , Ar 1 , Ar 2 and R 11 through R 22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl, halogen-substituted (C1-C30)alkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C6-C30)alkyl-substituted (C2-C30)heteroaryl, (C6-C30)aryl-substituted (C2-C30)heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (
- Chemical Formula 1 may be selected from the following structures, but is not limited thereto.
- R 1 , R 2 , R 11 through R 15 , o and p are the same as defined in Chemical Formula 1.
- X 1 through X 4 independently represent N or CR 3 ;
- Y 1 and Y 2 independently represent a single bond, -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-, except for a case where both Y 1 and Y 2 are a single bond;
- L 1 represents a single bond, phenylene, naphthalene, biphenylene, 9,9-diphenylfluorenylene, 9,9-dimethylfluorenylene, dibenzothiophene, dibenzofuran or spirofluorene;
- Ar 1 and Ar 2 independently represent hydrogen, phenyl, biphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, N-phenylcarbazolyl, dibenzothiophene or dibenzofuran, and the phen
- organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
- organic electroluminescent compound according to the present invention may be prepared as shown, for example, Scheme 1 below, but is not limited thereto.
- an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1.
- the organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer. Also, the compound of Chemical Formula 1 may be used after the addition of other host materials.
- the organic electroluminescent compound of Chemical Formula 1 when used as a host, one or more phosphorescent dopant(s) is included.
- the phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 2 below.
- M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
- R 201 through R 203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
- R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl,
- R 220 through R 223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
- R 224 and R 225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R 224 and R 225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
- R 226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
- R 227 through R 229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen;
- Q represents , or ;
- R 231 through R 242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- the dopant compound of Chemical Formula 2 may be exemplified by the following compounds, but is not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
- the organic layer may include an electroluminescent layer and a charge generating layer.
- the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
- the compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
- the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
- the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
- the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured 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.
- 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.
- the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
- the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
- an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
- Compound 1-1 (28g, 100.68mmol) was mixed with triethylphosphite 300mL and stirred at 150°C for 6 hours. The mixture was cooled to room temperature, distilled under reduced pressure, extracted with EA, and then washed with distilled water. Subsequently, drying with anhydrous MgSO 4 , distillation under reduced pressure and then column separation were conducted, yielding Compound 1-2 (11g, 44.69mmol, 44.38%).
- Compound 1-2 (30g, 101.29mmol), iodobenzene (41.3g, 202.59mmol), CuI (9.6g, 50.64mmol), Cs 2 CO 3 (82.5g, 253.2mmol), and toluene 600mL were mixed and heated at 50°C, and ethylenediamine (6.8mL, 101.29mmol) was added. The mixture was stirred under reflux. 14 hours later, the mixture was cooled to room temperature and distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO 4 , distilled under reduced pressure and column separated, yielding Compound 1-3 (32g, 85.96mmol, 84.86%).
- Dibenzo[b,d]thiophen-4-ylboronic acid (10g, 43.84mmol), bromonitrobenzene (8.85g, 43.84mmol), 2M Na 2 CO 3 aqueous solution 70mL, toluene 200mL, and ethanol 70mL were mixed and stirred under reflux. 5 hours later, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, dried with anhydrous MgSO 4 , and distilled under reduced pressure. Subsequently, column separation was carried out, yielding Compound 2-1 (10g, 32.74mmol, 74.68%).
- Compound 2-1 (10g, 32.74mmol) was mixed with triethylphosphite 100mL, and stirred at 150°C for 7 hours. The mixture was cooled to room temperature and distilled under reduced pressure. Subsequently, recrystallization was conducted using EA, yielding Compound 2-2 (7g, 25.60mmol, 78.19%).
- Compound 2-3 (8.2g, 19.1mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 2-4 (4.7g, 12.0mmol, 62%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 10 (5.3g, 9.2mmol, 67%) was prepared by the same method as in the preparation of Compound 1 .
- Compound 3-8 (5.8g, 11.0mmol, 59%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 3-9 (3.6g, 7.3mmol, 67%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 19 (5.0g, 9.2mmol, 69%) was prepared by the same method as in the preparation of Compound 1 .
- Compound 4-3 (8.4g, 20.4mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7 .
- Compound 4-4 (4.3g, 11.4mmol, 56%) was prepared by the same method as in the preparation of Compound 1-8 .
- Compound 20 (2.8g, 5.0mmol, 42%) was prepared by the same method as in the preparation of Compound 1 .
- An OLED device was manufactured using the compound for organic electronic materials according to the present invention.
- a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and 2-TNATA [4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine] was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10 -6 torr of vacuum in the chamber.
- Compound 10 as a host was placed in a cell, and 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole was placed in another cell, within a vacuum vapor deposition apparatus.
- the two materials were evaporated at the same rate and used as a host.
- a dopant, D-5, was added so that the host was 15 wt% doped, and thereby the electroluminescent layer was vapor-deposited to a thickness of 30 nm on the hole transport layer.
- Alq tris(8-hydroxyquinoline)-aluminum(III)
- Liq lithium quinolate
- Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
- Each compound used in the OLED device was purified by vacuum sublimation at 10 -6 torr before use.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 11 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 21 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 28 was used alone as the host material in the electroluminescent layer.
- An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using CBP (4,4'-bis(carbazol-9-yl)biphenyl) used as a host and Compound D-4 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
- CBP 4,4'-bis(carbazol-9-yl)biphenyl
- the devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
- an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
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Abstract
Organic electroluminescent compounds comprising a triphenylene conjugated to a five-ring fused heterocyclic system, as depicted in formula 1 are provided. Also provided is an organic electroluminescent device comprising these compounds. The organic electroluminescent compounds disclosed herein exhibit good luminous efficiency and excellent material life. They can be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.
Description
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
Among display devices, electroluminescent (EL) devices, which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material. Though fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism. Up to now, iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp)2, Ir(ppy)3 and Firpic, as the red, green and blue one, respectively. In particular, a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
At present, CBP is most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported. High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
Although these materials provide good electroluminescence characteristics, they are disadvantageous in that degradation may occur during the high-temperature deposition process in vacuum because of low glass transition temperature and poor thermal stability. Since the power efficiency of an OLED is given by (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of an OLED. Actually, OLEDs using phosphorescent materials provide much better current efficiency (cd/A) than those using fluorescent materials. However, when the existing materials such as BAlq, CBP, etc. are used as a host of the phosphorescent material, there is no significant advantage in power efficiency (lm/W) over the OLEDs using fluorescent materials because of high driving voltage. Furthermore, the life of an OLED device using such a material is not satisfactory, and therefore the development of a more stable host material having higher performance is required.
Meanwhile, KR Patent Publication No. 2010-0056490 discloses a compound for organic electroluminescent materials in which triphenylene is substituted for carbazole, dibenzofuran, dibenzothiophene, etc. The above-mentioned document KR2010-0056490 does not disclose a compound wherein triphenylene is linked to a 5 membered-heteroaryl group fused with the rings including benzothiophene, indole, indene and benzofuran at the carbazole.
Therefore, the present invention has been made keeping in mind the problems occurring in the related art and an object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional material.
Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
Provided are compounds for organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
[Chemical Formula 1]
wherein,
ring A represents 
; ring C represents 
;
ring B represents 
;
X1 through X4 independently represent CR3 or N;
Y1 and Y2 independently represent a single bond, -O-, -S-, -C(R11)(R12)-, -Si(R13)(R14)- or -N(R15)-, except for a case where both Y1 and Y2 are a single bond;
R1 through R3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyls, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR16R17, -SiR18R19R20, -SR21, -OR22, cyano, nitro or hydroxyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S;
R11 through R22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S;
L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, substituted or unsubstituted (C3-C30)cycloalkylene, -L2-L3- or -L3-L2-;
L2 represents substituted or unsubstituted (C6-C30)arylene;
L3 represents substituted or unsubstituted (C2-C30)heteroarylene;
Ar1 and Ar2 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
o represents an integer of 1 to 4, and when o is an integer of 2 or greater, each of R1 may be identical to or different from each other;
p represents an integer of 1 or 2, and when p represents 2, each of R2 may be identical to or different from each other; and
the heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si and P.
As described herein, "alkyl", "alkoxy" and other substituents containing the "alkyl" moiety include both linear and branched species, and the "cycloalkyl" includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring. As described herein, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl, and the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl, and the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl, the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
The "heteroaryl" described herein means an aryl group containing 1 to 4 heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s) and the remaining aromatic ring backbone atom is carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene ring(s), and may be partially saturated. In the present invention, "heteroaryl" includes a structure where one or more heteroaryls are linked by single bonds. The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt. Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, acridinyl, phenanthridinyl, phenanthrolinyl, phenoxazinyl, phenazinyl, phenothiazinyl, benzodioxolyl, dibenzofuranyl, dibenzothiophenyl or the like, N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide), quaternary salt thereof, and the like, but are not limited thereto.
The pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofuranyl includes 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl and 7-isobenzofuranyl; the quinolyl includes 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl and 8-quinolyl; the isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl and 8-isoquinolyl; the quinoxalinyl includes 2-quinoxalinyl, 5-quinoxalinyl and 6-quinoxalinyl; the carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl; the phenanthridinyl includes 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl and 10-phenanthridinyl; the acridinyl includes 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl and 9-acridinyl; the phenanthrolinyl includes 1,7-phenanthrolin-2-yl, 1,7-phenanthrolin-3-yl, 1,7-phenanthrolin-4-yl, 1,7-phenanthrolin-5-yl, 1,7-phenanthrolin-6-yl, 1,7-phenanthrolin-8-yl, 1,7-phenanthrolin-9-yl, 1,7-phenanthrolin-10-yl, 1,8-phenanthrolin-2-yl, 1,8-phenanthrolin-3-yl, 1,8-phenanthrolin-4-yl, 1,8-phenanthrolin-5-yl, 1,8-phenanthrolin-6-yl, 1,8-phenanthrolin-7-yl, 1,8-phenanthrolin-9-yl, 1,8-phenanthrolin-10-yl, 1,9-phenanthrolin-2-yl, 1,9-phenanthrolin-3-yl, 1,9-phenanthrolin-4-yl, 1,9-phenanthrolin-5-yl, 1,9-phenanthrolin-6-yl, 1,9-phenanthrolin-7-yl, 1,9-phenanthrolin-8-yl, 1,9-phenanthrolin-10-yl, 1,10-phenanthrolin-2-yl,1,10-phenanthrolin-3-yl, 1,10-phenanthrolin-4-yl, 1,10-phenanthrolin-5-yl, 2,9-phenanthrolin-1-yl, 2,9-phenanthrolin-3-yl, 2,9-phenanthrolin-4-yl, 2,9-phenanthrolin-5-yl, 2,9-phenanthrolin-6-yl, 2,9-phenanthrolin-7-yl, 2,9-phenanthrolin-8-yl, 2,9-phenanthrolin-10-yl, 2,8-phenanthrolin-1-yl, 2,8-phenanthrolin-3-yl, 2,8-phenanthrolin-4-yl, 2,8-phenanthrolin-5-yl, 2,8-phenanthrolin-6-yl, 2,8-phenanthrolin-7-yl, 2,8-phenanthrolin-9-yl, 2,8-phenanthrolin-10-yl, 2,7-phenanthrolin-1-yl, 2,7-phenanthrolin-3-yl, 2,7-phenanthrolin-4-yl, 2,7-phenanthrolin-5-yl, 2,7-phenanthrolin-6-yl, 2,7-phenanthrolin-8-yl, 2,7-phenanthrolin-9-yl and 2,7-phenanthrolin-10-yl; the phenazinyl includes 1-phenazinyl and 2-phenazinyl; the phenothiazinyl includes 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl and 10-phenothiazinyl; the phenoxazinyl includes 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl and 10-phenoxazinyl; the oxazolyl includes 2-oxazolyl, 4-oxazolyl and 5-oxazolyl; the oxadiazolyl includes 2-oxadiazolyl and 5-oxadiazolyl; the furazanyl includes 3-furazanyl; the dibenzofuranyl includes 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl and 4-dibenzofuranyl; and the dibenzothiophenyl includes 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl and 4-dibenzothiophenyl.
As described herein, the term "(C1-C30)alkyl" includes (C1-C20)alkyl or (C1-C10)alkyl, and the term "(C6-C30)aryl" includes (C6-C20)aryl. The term "(C2-C30)heteroaryl" includes (C2-C20)heteroaryl, and the term "(C3-C30)cycloalkyl" includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The term, "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
In the expression "substituted or unsubstituted(or with or without substitutent(s))" used herein, "with substituted(with substitutent(s))" means that the unsubstituted substituent is further substituted with substituent(s). The each substituent of the R1 through R3, L1, L2, L3, Ar1, Ar2 and R11 through R22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl, halogen-substituted (C1-C30)alkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C6-C30)alkyl-substituted (C2-C30)heteroaryl, (C6-C30)aryl-substituted (C2-C30)heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, N-carbazolyl, di(C1-C30)alkylamino, di(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, carboxyl, nitro and hydroxyl.
Also, 
of Chemical Formula 1 may be selected from the following structures, but is not limited thereto.
wherein R1, R2, R11 through R15, o and p are the same as defined in Chemical Formula 1.
To the specific, X1 through X4 independently represent N or CR3; Y1 and Y2 independently represent a single bond, -O-, -S-, -C(R11R12)- or -N(R15)-, except for a case where both Y1 and Y2 are a single bond; L1 represents a single bond, phenylene, naphthalene, biphenylene, 9,9-diphenylfluorenylene, 9,9-dimethylfluorenylene, dibenzothiophene, dibenzofuran or spirofluorene; Ar1 and Ar2 independently represent hydrogen, phenyl, biphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, N-phenylcarbazolyl, dibenzothiophene or dibenzofuran, and the phenyl, biphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, N-phenylcarbazolyl, dibenzothiophene and dibenzofuran of Ar1 and Ar2 may be further substituted with one or more substituents selected from the group consisting of deuterium, fluorine, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, triphenylsilyl, trimethylsilyl, diphenylmethylsilyl, phenyl and naphthyl; R1 through R3 independently represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuryl, dibenzothiophenyl, triphenylsilyl or diphenylmethylsilyl; R11 through R22 independently represent hydrogen, deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, trifluoromethyl, phenyl, naphthyl, pyridyl or quinolyl, or they may be linked via substituted or unsubstituted (C3-C7)alkylene or substituted or unsubstituted (C3-C7)alkenylene with or without a fused ring to form a fused ring, and the phenyl of R11 through R22 may be further substituted with one or more substituents selected from the group consisting of deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, trifluoromethyl, phenyl and naphthyl.
The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
The organic electroluminescent compound according to the present invention may be prepared as shown, for example, Scheme 1 below, but is not limited thereto.
[Scheme 1]
In Scheme 1, ring A, ring B, ring C, L1, Ar1, Ar2, R1 and o are the same as defined in Chemical Formula 1; and X represents halogen.
Provided is an organic electroluminescent device, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1. The organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer. Also, the compound of Chemical Formula 1 may be used after the addition of other host materials.
In the electroluminescent layer, when the organic electroluminescent compound of Chemical Formula 1 is used as a host, one or more phosphorescent dopant(s) is included. The phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 2 below.
[Chemical Formula 2]
M1L101L102L103
wherein,
M1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L101, L102 and L103 are independently selected from the following structures:
R201 through R203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
R204 through R219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF5, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, cyano or halogen;
R220 through R223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
R224 and R225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R224 and R225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
R227 through R229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen; and
Q represents 
, 
or 
;
R231 through R242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
The dopant compound of Chemical Formula 2 may be exemplified by the following compounds, but is not limited thereto.
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
Further, the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device. The compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom. The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured 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. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
According to the present invention, an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
Hereinafter, the present invention is further described by taking representative compounds of the present invention as examples of the organic electroluminescent compounds according to the invention, a preparing method thereof, and electroluminescent properties of the devices. But, those examples are provided only for the sake of illustrating the embodiments, and are not intended to limit the scope of the invention.
[Preparation Example 1] Preparation of Compound 1
Preparation of Compound
1-1
2-iodobenzene (30g, 120.4mmol), 4-bromophenylboronic acid (26g, 132.5mmol), Pd(PPh3)4 (6.9g, 6.02mmol), 2M Na2CO3 150mL, and toluene 500mL were heated at 100℃. 4 hours later, the mixture was cooled to room temperature, extracted with ethyl acetate (EA), washed with distilled water, dried with anhydrous MgSO4, distilled under reduced pressure, and column separated, yielding Compound 1-1 (28g, 100.68mmol, 83,33%).
Preparation of Compound
1-2
Compound 1-1 (28g, 100.68mmol) was mixed with triethylphosphite 300mL and stirred at 150℃ for 6 hours. The mixture was cooled to room temperature, distilled under reduced pressure, extracted with EA, and then washed with distilled water. Subsequently, drying with anhydrous MgSO4, distillation under reduced pressure and then column separation were conducted, yielding Compound 1-2 (11g, 44.69mmol, 44.38%).
Preparation of Compound
1-3
Compound 1-2 (30g, 101.29mmol), iodobenzene (41.3g, 202.59mmol), CuI (9.6g, 50.64mmol), Cs2CO3 (82.5g, 253.2mmol), and toluene 600mL were mixed and heated at 50℃, and ethylenediamine (6.8mL, 101.29mmol) was added. The mixture was stirred under reflux. 14 hours later, the mixture was cooled to room temperature and distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO4, distilled under reduced pressure and column separated, yielding Compound 1-3 (32g, 85.96mmol, 84.86%).
Preparation of Compound
1-4
Compound 1-3 (32g, 85.96mmol) was dissolved in THF 300mL and n-butyllithium (37.8mL, 94.55mmol, 2.5M in hexane) was slowly added at -78℃. 1 hour later, trimethylborate (12.4mL, 111.7mmol) was added. The mixture was stirred at room temperature for 12 hours, and then distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO4, distilled under reduced pressure and column separated, yielding Compound 1-4 (20g, 59.31mmol, 69.00%).
Preparation of Compound
1-5
Compound 1-4 (20g, 59.31mmol), 1-bromo-2-nitrobenzene (14.3g, 71.17mmol), Pd(PPh3)4 (2.7g, 2.37mmol), 2M Na2CO3 75mL, toluene 300mL, and ethanol 70mL were mixed and stirred under reflux. 5 hours later, the mixture was cooled to room temperature and distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO4, distilled under reduced pressure and column separated, yielding Compound 1-5 (20g, 48.25mmol, 81.36%).
Preparation of Compound
1-6
Compound 1-5 (20g, 48.25mmol) and triethylphosphite 200mL were mixed, stirred at 150℃ for 6 hours, cooled to room temperature, and distilled under reduced pressure. The mixture was extracted with EA, washed with distilled water, dried with anhydrous MgSO4, distilled under reduced pressure and column separated, yielding Compound 1-6 (7g, 18.30mmol, 37.93%).
Preparation of Compound
1-7
Into a 1L 2-neck round bottom flask (RBF), Compound 1-6 (19.3g, 0.058mol), 1,3-dibromobenzene (82g, 0.349mol), CuI (5.5g, 2.91mmol), K3PO4 (25g, 0.11mol), ethylenediamine (4mL, 0.058mol) and toluene 500mL was added and heated to 75℃. The mixture was stirred for 12 hours, filtered to remove Cu, washed with distilled water, and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column purification was conducted, yielding Compound 1-7 (20.0g, 71%).
Preparation of Compound
1-8
In a 1L RBF, Compound 1-7 (20.0g, 0.041mol) was placed and dried in a vacuum, and nitrogen gas was charged. THF 300mL was added, and the mixture was cooled to -78℃. n-BuLi(2.5M) (24.7mL, 0.061mol) was slowly added, and the mixture was stirred at low temperature for 1 hour. B(i-pro)3 (14.2mL, 0.061mmol) was added at -78℃, and the mixture was stirred for 12 hours. After termination of the reaction, 1M HCl was added. 10 minutes later, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column purification was conducted, yielding Compound 1-8 (17.7g, 90%).
Preparation of Compound
1
Into a 500mL 2-neck RBF, 2-bromotriphenylene (7.2g, 23.44mmol), Compound 1-8 (15.9g, 35.16mmol), Pd(OAc)2 (790mg, 3.51mmol), P(t-Bu)3 (4.7mL, 7.03mmol), K3PO4 (2M) (46mL, 93.76mmol), ethanol 46mL, and toluene 200mL were added, and the mixture was heated to 120℃ and stirred for 2 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column purification was conducted, yielding Compound 1 (6.5g, 44%).
MS/FAB found 635, calculated 634.77
[Preparation Example 2] Preparation of Compound 10
Preparation of Compound
2-1
Dibenzo[b,d]thiophen-4-ylboronic acid (10g, 43.84mmol), bromonitrobenzene (8.85g, 43.84mmol), 2M Na2CO3 aqueous solution 70mL, toluene 200mL, and ethanol 70mL were mixed and stirred under reflux. 5 hours later, the mixture was cooled to room temperature, extracted with EA, washed with distilled water, dried with anhydrous MgSO4, and distilled under reduced pressure. Subsequently, column separation was carried out, yielding Compound 2-1 (10g, 32.74mmol, 74.68%).
Preparation of Compound
2-2
Compound 2-1 (10g, 32.74mmol) was mixed with triethylphosphite 100mL, and stirred at 150℃ for 7 hours. The mixture was cooled to room temperature and distilled under reduced pressure. Subsequently, recrystallization was conducted using EA, yielding Compound 2-2 (7g, 25.60mmol, 78.19%).
Preparation of Compound
2-3
Compound 2-3 (8.2g, 19.1mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7.
Preparation of Compound
2-4
Compound 2-4 (4.7g, 12.0mmol, 62%) was prepared by the same method as in the preparation of Compound 1-8.
Preparation of Compound
10
Compound 10 (5.3g, 9.2mmol, 67%) was prepared by the same method as in the preparation of Compound 1.
MS/FAB found 576, calculated 575.72
[Preparation Example 3] Preparation of Compound 19
Preparation of Compound
3-1
2-(phenylamino)benzoic acid (50g, 0.23mol) was dissolved in MeOH 1L, placed in an ice bath and then stirred at 0℃ for 10 minutes. SOCl2 (60mL, 0.58mol) was slowly added at 0℃ and the mixture was stirred under reflux at 90℃ for 12 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-1 (47g, 92%).
Preparation of Compound
3-2
Compound 3-1 (90g, 0.3mol) was added to THF 1.5L, and MeMgBr(3.0M) (462mL, 1.38mol) was slowly added, after which the mixture was stirred at room temperature for 12 hours. After termination of the reaction, the mixture was neutralized with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-2 (80g, 90%).
Preparation of Compound
3-3
Compound 3-2 (80g, 0.35mol) was added to H3PO4 1.7L and the mixture was stirred at room temperature for 12 hours. After termination of the reaction, the mixture was neutralized with distilled water, and the produced solid was washed with water and filtered. The solid was dissolved in dichloromethane, extracted, and neutralized with NaOH. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently recrystallization was conducted using hexane, yielding Compound 3-3 (64g, 87%).
Preparation of Compound
3-4
Compound 3-3 (64g, 0.30mol), bromobenzene (52.8g, 0.33mol), Pd(OAc)2 (1.37g, 6.11mmol), P(t-Bu)3 50% (7.3mL, 15.28mmol) and NaOt-Bu (58g, 0.61mol) were dissolved in toluene 1.2L and stirred at 120℃ for 12 hours. After termination of the reaction, the mixture was neutralized with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-4 (71g, 81%).
Preparation of Compound
3-5
Compound 3-4 (20g, 0.07mol) was dissolved in DMF 800mL and stirred at 0℃ for 10 minutes. A solution of NBS (12.5g, 0.07mol) in DMF 350mL was slowly added, and the mixture was stirred at 0℃ for 6 hours. After termination of the reaction, the mixture was neutralized with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-5 (21g, 84%).
Preparation of Compound
3-6
Compound 3-5 (20g, 0.054mol), 2-chloroaniline (8.4g, 0.065mol), Pd(OAc)2 (370mg, 1.64mmol), P(t-Bu)3 50% (3.6mL, 5.49mmol) and Cs2CO3 (35.7g, 0.109mol) were dissolved in toluene 300mL and stirred at 120℃ for 4 hours. After termination of the reaction, the mixture was neutralized with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-6 (13.6g, 60%).
Preparation of Compound
3-7
Compound 3-6 (12.6g, 0.03mol), Pd(OAc)2 (1.37mg, 6.13mmol), di-tert-butyl(methyl)phosphonium tetrafluoroborate (3g, 12.26mmol) and Cs2CO3 (50g, 0.15mol) were dissolved in DMA 240mL and stirred at 190℃ for 4 hours. After termination of the reaction, the mixture was neutralized with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted using EA as a developer, yielding Compound 3-7 (7g, 18.7mmol, 70%).
Preparation of Compound
3-8
Compound 3-8 (5.8g, 11.0mmol, 59%) was prepared by the same method as in the preparation of Compound 1-7.
Preparation of Compound
3-9
Compound 3-9 (3.6g, 7.3mmol, 67%) was prepared by the same method as in the preparation of Compound 1-8.
Preparation of Compound
19
Compound 19 (5.0g, 9.2mmol, 69%) was prepared by the same method as in the preparation of Compound 1.
MS/FAB found 677, calculated 676.84
[Preparation Example 4] Preparation of Compound 20
Preparation of Compound
4-1
1-bromo-2-nitrobenzene (16g, 74.25mmol), dibenzo[b,d]furan-2-ylboronic acid (23g, 96.60mmol), Pd(PPh3)4 (4.2g, 3.63mmol), 2M K2CO3 aqueous solution 111mL, EtOH 100mL and toluene 200mL were mixed and then heated to 120℃ with stirring for 3 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 4-1 (22g, 95%).
Preparation of Compound
4-2
Compound 4-1 (24g, 76.10mmol), triethylphosphite 200mL and 1,2-dichlorobenzene 200mL were mixed, and the mixture was heated to 180℃ and stirred for 12 hours. After termination of the reaction, unreacted triethylphosphite and 1,2-dichlorobenzene were removed using a distillation device, and the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 4-2 (7g, 27.2mmol, 33%).
Preparation of Compound
4-3
Compound 4-3 (8.4g, 20.4mmol, 75%) was prepared by the same method as in the preparation of Compound 1-7.
Preparation of Compound
4-4
Compound 4-4 (4.3g, 11.4mmol, 56%) was prepared by the same method as in the preparation of Compound 1-8.
Preparation of Compound
20
Compound 20 (2.8g, 5.0mmol, 42%) was prepared by the same method as in the preparation of Compound 1.
MS/FAB found 560, calculated 559.65
[Preparation Example 5] Preparation of Compound 11
Preparation of Compound
5-1
1-bromo-2-nitrobenzene (39g, 0.19mol), dibenzo[b,d]furan-4-ylboronic acid (45g, 0.21mol), Pd(PPh3)4 (11.1g, 0.0096mol), 2M K2CO3 aqueous solution 290mL, EtOH 290mL and toluene 580mL were mixed and then heated to 120℃ with stirring for 4 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 5-1 (47g, 85%).
Preparation of Compound
5-2
Compound 5-1 (47g, 0.16mol), triethylphosphite 600mL and 1,2-dichlorobenzene 300mL were mixed, and the mixture was heated to 150℃ and stirred for 12 hours. After termination of the reaction, unreacted triethylphosphite and 1,2-dichlorobenzene were removed using a distillation device, and the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 5-2 (39g, 81%).
Preparation of Compound
5-3
Into a 1L 2-neck RBF, Compound 5-2 (15g, 0.058mol), 1,3-dibromobenzene (82g, 0.349mol), CuI (5.5g, 2.91mmol), K3PO4 (25g, 0.11mol), ethylenediamine (4mL, 0.058mol) and toluene 500mL were added and heated to 75℃. The mixture was stirred for 12 hours and then filtered, and Cu was removed. The mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column purification was carried out, yielding Compound 5-3 (17.1g, 71%).
Preparation of Compound
5-4
In a 1L RBF, Compound 5-3 (17.0g, 0.041mol) was placed and dried in a vacuum, and nitrogen gas was charged. THF 300mL was added, and the mixture was cooled to -78℃. n-BuLi(2,5M) (24.7mL, 0.061mol) was slowly added and the mixture was stirred at low temperature for 1 hour. B(i-pro)3 (14.2mL, 0.061mmol) was added at -78℃ and the mixture was stirred for 12 hours. After termination of the reaction, 1M HCl was added. 10 minutes later, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently column purification was conducted, yielding Compound 5-4 (13.8g, 90%).
Preparation of Compound
11
Into a 500mL 2-neck RBF, 2-bromotriphenylene (7.2g, 23.44mmol), Compound 5-4 (13.2g, 5.16mmol), Pd(OAc)2 (790mg, 3.51mmol), P(t-Bu)3 (4.7mL, 7.03mmol), K3PO4 (2M) (46mL, 93.76mmol), ethanol 46mL, and toluene 200mL were added, and the mixture was heated to 120℃ and stirred for 2 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently column purification was conducted, yielding Compound 11 (5.8g, 44%).
MS/FAB found 559, calculated 559.19
[Preparation Example 6] Preparation of Compound 21
Preparation of Compound
6-1
2-bromo-9,9-dimethyl-9H-fluorene (80g, 291mmol), 2-chlorobenzeneamine (45mL, 437mmol), Pd(OAc)2 (2.6g, 12mmol), P(t-Bu)3 (12mL, 24mmol), NaOt-Bu (70g, 728mmol) and toluene 800mL were mixed and then heated to 120℃ with stirring for 9 hours. After termination of the reaction, the mixture was cooled to room temperature and extracted with EA 1.5L, and the obtained organic layer was washed with distilled water 400mL. The solvent was removed under reduced pressure and the obtained solid was washed with hexane, filtered and dried. Subsequently silica gel column chromatography and recrystallization were performed, yielding Compound 6-1 (70g, 75%).
Preparation of Compound
6-2
Compound 6-1 (70g, 218mmol), Pd(OAc)2 (2.4g, 11mmol), PCy3HBF4 (8g, 22mmol), Na2CO3 (70g, 654mmol) and DMA 1.2L were mixed and stirred at 190℃ for 3 hours. After termination of the reaction, the mixture was extracted with EA 1L, and the obtained organic layer was washed with distilled water 200mL and dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. The obtained solid was separated using silica gel column chromatography and recrystallization, yielding Compound 6-2 (22g, 36%).
Preparation of Compound
6-3
Compound 6-2 (15g, 53mmol), 1,3-dibromobenzene (32mL, 265mmol), Pd(OAc)2 (1.2g, 5mmol), P(t-Bu)3 (30mL, 64mmol), NaOt-Bu (25g, 265mmol) and toluene 300mL were mixed and stirred at 120℃ for 24 hours. After termination of the reaction, the mixture was cooled to room temperature and extracted with EA 1.5L, and the obtained organic layer was washed with distilled water 400mL. Subsequently, the solvent was removed under reduced pressure and the obtained solid was washed with hexane, filtered and dried. Silcia gel column chromatography and recrystallization were performed, yielding Compound 6-3 (7g, 30%).
Preparation of Compound
6-4
Compound 6-3 (7g, 16mmol) was dissolved in THF 100mL and n-BuLi(2.5 M in hexane) (10mL, 24mmol) was added at -78℃. The mixture was stirred at -78℃ for 1 hour and B(Oi-Pr)3 (6mL, 24mmol) was added. Stirring was performed for 2 hours and the reaction was terminated with aqueous ammonium chloride 20mL. The resultant mixture was extracted with EA 500mL, and the obtained organic layer was washed with distilled water 200 mL. The organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. The obtained solid was separated using recrystallization, yielding Compound 6-4 (5g, 75%).
Preparation of Compound
21
Compound 6-4 (3.7g, 9.2mmol), 2-bromotriphenylene (2.6g, 8.3mmol), Pd(OAc)2 (94mg, 0.4mmol), P(t-Bu)3 (0.4mL, 0.8mmol), Cs2CO3 (8.2g, 25mmol), toluene 30mL, EtOH 15mL and distilled water 15mL were mixed, and the mixture was stirred at 120℃ for 16 hours. The mixture was cooled to room temperature and extracted with EA 200mL, and the obtained organic layer was washed with distilled water 50mL, after which the organic solvent was removed under reduced pressure. The obtained solid was washed with hexane, filtered and then dried. The obtained solid was separated using silica gel column chromatography and recrystallization, yielding Compound 21 (1.1g, 22%).
MS/FAB found 585, calculated 585.25
[Preparation Example 7] Preparation of Compound 28
Preparation of Compound
7-1
2-bromotriphenylene (63.7, 207.4mmol) was dissolved in THF 1.5L and cooled to -78℃. 10 minutes later, n-BuLi(2.5M in hexane) (125mL, 311mmol) was slowly added and the mixture was stirred for 1 hour. Triethylborate (67mL, 311mmol) was slowly added, and the mixture was stirred for 24 hours. After termination of the reaction, 1M HCl was added, and the mixture was extracted with EA. Subsequently, the residual moisture was removed using anhydrous MgSO4, after which drying and recrystallization from hexane were carried out, yielding Compound 7-1 (31.8g, 55%).
Preparation of Compound
7-2
In a flask, 2,4-dichloropyrimidine (9.7g, 65.1mmol), Compound 7-1 (17.72g, 65.1mmol), Pd(PPh3)4 (3.76g, 3.25mmol), Na2CO3 (20.7g, 195.3mmol) and DME 1.5L were placed and dissolved, and the mixture was stirred at 120℃ for 7 hours. After reaction, distilled water was slowly added so that the reaction was terminated, and the organic layer was obtained via extraction using EA, and the residual moisture was removed using anhydrous MgSO4. Subsequently, drying and column separation were performed, yielding Compound 7-2 (4g, 20%).
Preparation of Compound
28
In a flask, NaH (651g, 19.3mmol) was dissolved in DMF 100mL and stirred. A solution of Compound 5-2 (4g, 15.4mmol) in DMF was added to the NaH solution, and the mixture was stirred for 1 hour (reaction mixture A). Compound 7-2 (4.4g, 12.9mmol) was dissolved in DMF, stirred, and added to the reaction mixture A that had been stirred for 1 hour, and the mixture was stirred at room temperature for 24 hours. After termination of the reaction, the produced solid was filtered, washed with EA and purified by column chromatography, yielding Compound 28 (3.5g, 48%).
MS/FAB found 561, calculated 561.18
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the compound for organic electronic materials according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use. Then, an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and 2-TNATA [4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine] was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate it, thereby depositing a hole injection layer having a thickness of 60 nm on the ITO substrate. Subsequently, N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was placed in another cell of the vacuum deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer. After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound 10 as a host was placed in a cell, and 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole was placed in another cell, within a vacuum vapor deposition apparatus. The two materials were evaporated at the same rate and used as a host. A dopant, D-5, was added so that the host was 15 wt% doped, and thereby the electroluminescent layer was vapor-deposited to a thickness of 30 nm on the hole transport layer. Subsequently, Alq [tris(8-hydroxyquinoline)-aluminum(III)] was vapor-deposited to a thickness of 20 nm as an electron transport layer on the electroluminescent layer. Subsequently, Liq (lithium quinolate) was vapor-deposited to a thickness of 2 nm as an electron injection layer, after which an Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED device was purified by vacuum sublimation at 10-6 torr before use.
As a result, it was confirmed that current of 1.6 mA/cm2 flows at voltage of 4.7 V and a green light of 685 cd/m2 was emitted.
[Example 2] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 11 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
As a result, it was confirmed that current of 5.3 mA/cm2 flows at voltage of 5.6 V and a green light of 2190 cd/m2 was emitted.
[Example 3] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 21 was used as the host material, and D-34 was used as a dopant in the electroluminescent layer.
As a result, it was confirmed that current of 3.0 mA/cm2 flows at voltage of 5.2 V and a green light of 1240 cd/m2 was emitted.
[Example 4] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 28 was used alone as the host material in the electroluminescent layer.
As a result, it was confirmed that current of 10.6 mA/cm2 flows at voltage of 6.4 V and a green light of 4520 cd/m2 was emitted.
[Comparative Example 1] Electroluminescent properties of OLED device using an electroluminescent material of the prior art.
An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using CBP (4,4'-bis(carbazol-9-yl)biphenyl) used as a host and Compound D-4 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
As a result, it was confirmed that current of 3.8 mA/cm2 flows at voltage of 7.5 V and a green light of 1000 cd/m2 was emitted.
The devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
Although the preferred embodiments of the present invention have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions, and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.
According to the present invention, an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1 below.[Chemical Formula 1]
wherein,ring A represents; ring C represents
;
ring B represents;
X1 through X4 independently represent CR3 or N;Y1 and Y2 independently represent a single bond, -O-, -S-, -C(R11)(R12)-, -Si(R13)(R14)- or -N(R15)-, except for a case where both Y1 and Y2 are a single bond;R1 through R3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyls, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR16R17, -SiR18R19R20, -SR21, -OR22, cyano, nitro or hydroxyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S;R11 through R22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatoms selected from the group consisting of N, O and S;L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, substituted or unsubstituted (C3-C30)cycloalkylene, -L2-L3- or -L3-L2-;L2 represents substituted or unsubstituted (C6-C30)arylene;L3 represents substituted or unsubstituted (C2-C30)heteroarylene;Ar1 and Ar2 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;o represents an integer of 1 to 4, and when o is an integer of 2 or greater, each of R1 may be identical to or different from each other;p represents an integer of 1 or 2, and when p represents 2, each of R2 may be identical to or different from each other; andthe heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si and P. - The organic electroluminescent compound of claim 1, wherein each substituent of the R1 through R3, L1, L2, L3, Ar1, Ar2 and R11 through R22 is further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl, halogen-substituted (C1-C30)alkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C6-C30)alkyl-substituted (C2-C30)heteroaryl, (C6-C30)aryl-substituted (C2-C30)heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, N-carbazolyl, di(C1-C30)alkylamino, di(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, carboxyl, nitro and hydroxyl.
- The organic electroluminescent compound of claim 1, wherein theis selected from following structures.
wherein R1, R2, R11 through R15, o and p are the same as defined in Chemical Formula 1 of claim 1. - The organic electroluminescent compound of claim 3, which is selected from following compounds.
- An organic electroluminescent device comprising the organic electroluminescent compound of any one of claims 1 to 4.
- The organic electroluminescent device of claim 5, which comprises a first electrode; a second electrode; and one or more organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds and one or more phosphorescent dopants.
- The organic electroluminescent device of claim 6, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds.
- The organic electroluminescent device of claim 6, wherein the organic layer further comprises one or more metals selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
- The organic electroluminescent device of claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more organic electroluminescent layers emitting red, green and blue light to emit white light.
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| CN201180055620XA CN103228661A (en) | 2010-09-20 | 2011-09-16 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2013529070A JP2013544759A (en) | 2010-09-20 | 2011-09-16 | Novel organic electroluminescent compound and organic electroluminescent device using the same |
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| KR10-2011-0092141 | 2011-09-09 | ||
| KR1020110092141A KR20120030941A (en) | 2010-09-20 | 2011-09-09 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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