WO2011071255A1 - 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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- WO2011071255A1 WO2011071255A1 PCT/KR2010/008245 KR2010008245W WO2011071255A1 WO 2011071255 A1 WO2011071255 A1 WO 2011071255A1 KR 2010008245 W KR2010008245 W KR 2010008245W WO 2011071255 A1 WO2011071255 A1 WO 2011071255A1
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- WIPO (PCT)
- Prior art keywords
- substituent
- alkyl
- aryl
- organic electroluminescent
- independently represent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 239000000126 substance Substances 0.000 claims abstract description 21
- -1 cyano, carbazolyl Chemical group 0.000 claims description 123
- 125000001424 substituent group Chemical group 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 40
- 239000010410 layer Substances 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 239000002019 doping agent Substances 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 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
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 description 47
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 10
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 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 4
- 229940126086 compound 21 Drugs 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005401 electroluminescence Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
- 230000000903 blocking effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- 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 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [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
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- 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
- 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
- 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol 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-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 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
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000010992 reflux Methods 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical class [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
- 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
- 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same as host.
- electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
- 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].
- an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and exciton is generated. Light is emitted by using electroluminescence (phosphorescence or fluorescence) in a state that the exciton is inactivated.
- the organic EL device emits polarization of light at voltage of about 10V and high brightness of about 100 ⁇ 10,000cd/m2.
- the organic EL device has a feature in that light is emitted in a spectrum ranging from blue color to red color by simply selecting a fluorescent material.
- the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
- the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
- Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials.
- the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
- Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
- electroluminescent materials for red, green and blue
- OLED organic light-emitting diode
- the important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices.
- the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host.
- the desired properties for the host material are high purity and appropriate molecular weight to enable vapor-deposition in vacuo.
- glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability.
- the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other adjacent materials but without interlayer migration.
- the organic EL device When the organic EL device is fabricated by doping technology, transferring energy from host molecule to dopant in an excited state does not achieve 100% and a host material as well as dopant emits light. In particular, since the host material emits light in a range of wavelength having larger visibility than the dopant material in case of a red light emitting device, color purity is deteriorated due to dull light emission of the host material. If the technology is actually applied, it is required to increase luminescence life and improve durability.
- 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.
- the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
- an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having a superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
- Another object of the present invention is to provide a highly efficient and long life organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
- organic electroluminescent compound represented by following Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
- a 1 , A 2 and B 1 through B 8 independently represent CR or N;
- X represents a chemical bond, -C(R 11 )(R 12 )-, -N(R 13 )-, -S-, -O- or -Si(R 14 )(R 15 )-;
- R, R 1 through R 6 and R 11 through R 15 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, NR 21 R 22 , BR 23 R 24 ,
- R 41 through R 43 and R 51 through R 58 are the same as R, R 1 through R 6 and R 11 through R 15 ;
- n an integer from 1 to 3.
- R 43 and R 51 through R 58 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or the R 51 through R 58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring.
- alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species and "cycloalkyl” includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or (C7-C30)bicycloalkyl with or without substituent(s).
- 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, including a plurality of aryls linked by single bond(s).
- Specific examples 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 fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- heteroaryl may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated.
- the heteroaryl includes more than one heteroaryls linked by single bond(s).
- the heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
- monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzo
- the “(C1-C30)alkyl” groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the "(C6-C30)aryl” groups include (C6-C20)aryl or (C6-C12)aryl.
- the "(C3-C30)heteroaryl” groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the "(C3-C30)cycloalkyl” groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
- the "(C2-C30alkenyl or alkynyl” group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
- a substituent further substituted by the R, R 1 through R 6 , R 11 through R 15 , R 21 through R 32 , R 41 through R 43 and R 51 through R 58 is one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one
- R in the following structures is preferably hydrogen.
- R is the same as defined in Chemical Formula 1.
- R and R 11 through R 15 independently represent halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or carbazolyl; R may be identical or different; and a and b independently represent an integer from 0 to 4.
- R and R 1 through R 6 independently represent hydrogen, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, 1-naphthyl, 2-naphthyl, 1,2-biphenyl, 1,3-biphenyl, 1-4-biphenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, N-carbazolyl, N-phenyl-1-carbazolyl, N-phenyl-2-carbazolyl, N-phenyl-3-carbazolyl, N-phenyl-4-carbazolyl, 2-pyridyl, 3-pyr
- organic electroluminescent compound according to the present invention may be more specifically exemplified as following compounds but is not limited thereto.
- the organic electroluminescent compound according to the present invention may be prepared as shown in following Scheme 1.
- a 1 , A 2 , B 1 through B 8 , X and R 1 through R 6 are the same as defined in Chemical Formula 1.
- 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 compound(s) represented by Chemical Formula 1.
- the organic layer may include one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s).
- the dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 2:
- M 1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals;
- ligands L 101 , L 102 and L 103 are independently selected from the following structures:
- R 201 through R 203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen;
- R 204 through R 219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF 5 , tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
- R 220 through R 223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);
- R 224 and R 225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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 or a mono- or polycyclic aromatic ring;
- R 226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen;
- R 227 through R 229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen;
- Q represents , or , wherein R 231 through R 242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), or each of them 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 represented by Chemical Formula 2 may be exemplified by the compounds having following structures, 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 compounds.
- 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, 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 compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- 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 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. An operation stability may be attained therefrom.
- 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.
- an 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.
- the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
- Organic electroluminescent Compounds 1 to 39 were prepared according to Preparation Example 1.
- Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
- An OLED device was manufactured using the electroluminescent material 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 vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- an electroluminescent layer was formed thereon as follows. A compound 16 was placed in a cell of a vacuum vapor deposition apparatus as a host, and a compound Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 4 to 10 wt%.
- An OLED device was manufactured according to the same method as Example 1 except that a compound 19 was used on the electroluminescent layer as a host material and Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
- An OLED device was manufactured according to the same method as Example 1 except that a compound 21 was used on the electroluminescent layer as a host material and Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
- An OLED device was manufactured according to the same method as Example 1 except that a compound 30 was used on the electroluminescent layer as a host material and Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
- An OLED device was manufactured according to the same method as Example 1 except that a compound 35 was used on the electroluminescent layer as a host material and Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
- An OLED device was manufactured in the same manner as Examples 1 and 2 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention was used as a host material in a cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III) (BAlq) was used as the hole blocking layer.
- CBP 4,4'-bis(carbazol-9-yl)biphenyl
- BAlq Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III)
- the organic electroluminescent compounds according to the present invention have excellent properties compared with the conventional material.
- the device using the organic electroluminescent compound according to the present invention as a host material has excellent electroluminescent properties and drops driving voltage, thereby increasing power efficiency and reducing power consumption.
- the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
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Abstract
Provided are novel organic electroluminescent compounds of Chemical Formula 1 (wherein X, B1-B8, A1, A2 and R1-R6 are as defined in the application) and an organic electroluminescent device using the same. Since the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
Description
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same as host.
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. 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].
In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and exciton is generated. Light is emitted by using electroluminescence (phosphorescence or fluorescence) in a state that the exciton is inactivated. The organic EL device emits polarization of light at voltage of about 10V and high brightness of about 100∼10,000cd/㎡. The organic EL device has a feature in that light is emitted in a spectrum ranging from blue color to red color by simply selecting a fluorescent material. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials. The low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure. Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
Three electroluminescent materials (for red, green and blue) are employed to realize a full-colored organic light-emitting diode (OLED) display. The important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices. From the aspect of function, the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel. From this point of view, development of host material is one of the most important issues to be settled. The desired properties for the host material (serving as a solvent and energy conveyer in solid state) are high purity and appropriate molecular weight to enable vapor-deposition in vacuo. In addition, glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability. Further, the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other adjacent materials but without interlayer migration.
When the organic EL device is fabricated by doping technology, transferring energy from host molecule to dopant in an excited state does not achieve 100% and a host material as well as dopant emits light. In particular, since the host material emits light in a range of wavelength having larger visibility than the dopant material in case of a red light emitting device, color purity is deteriorated due to dull light emission of the host material. If the technology is actually applied, it is required to increase luminescence life and improve durability.
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.
Further, the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
Accordingly, an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having a superior backbone with appropriate color coordinates in order to solve the aforesaid problems. Another object of the present invention is to provide a highly efficient and long life organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
Provided are a novel organic electroluminescent compound represented by following Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
[Chemical Formula 1]
wherein
A1, A2 and B1 through B8 independently represent CR or N;
X represents a chemical bond, -C(R11)(R12)-, -N(R13)-, -S-, -O- or -Si(R14)(R15)-;
R, R1 through R6 and R11 through R15 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], R29R30R31Si- [wherein R29 through R31 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl with or without substituent(s), R32Y- [wherein Y represents S or O, and R32 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)] (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), 
or 
, or each of them 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, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring; and each of the rings A and B independently represent a (C5-C30)alicyclic ring with or without substituent(s), a (C6-C30)aromatic ring with or without substituent(s), or a (C6-C30)heteroaromatic ring with or without substituent(s);
W represents a chemical bond, -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
R41 through R43 and R51 through R58 are the same as R, R1 through R6 and R11 through R15;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
m represents an integer from 1 to 3.
To be specific, the 
and 
may be independently exemplified as following structures but are not limited thereto.
wherein
R43 and R51 through R58 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or the R51 through R58 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species and "cycloalkyl" includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or (C7-C30)bicycloalkyl with or without substituent(s).
In the present invention, "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, including a plurality of aryls linked by single bond(s). Specific examples 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, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. In the present invention, "heteroaryl" means an aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
The "(C1-C30)alkyl" groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the "(C6-C30)aryl" groups include (C6-C20)aryl or (C6-C12)aryl. The "(C3-C30)heteroaryl" groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the "(C3-C30)cycloalkyl" groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The "(C2-C30alkenyl or alkynyl" group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
In the term 'substituted or unsubstituted (or with or without) substituent(s)' described herein, the term 'substituted' means to be further substituted by an unsubstituted substituent. A substituent further substituted by the R, R1 through R6, R11 through R15, R21 through R32, R41 through R43 and R51 through R58 is one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NRdRe, BRfRg, PRhRi, P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlX-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl, and Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; X represents S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
The 
is selected from following structures and R in the following structures is preferably hydrogen.
wherein
R is the same as defined in Chemical Formula 1.
Also, the 
is selected from the following structures, but is not limited thereto.
wherein
R and R11 through R15 independently represent halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or carbazolyl; R may be identical or different; and a and b independently represent an integer from 0 to 4.
Preferably, R and R1 through R6 independently represent hydrogen, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, 1-naphthyl, 2-naphthyl, 1,2-biphenyl, 1,3-biphenyl, 1-4-biphenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, N-carbazolyl, N-phenyl-1-carbazolyl, N-phenyl-2-carbazolyl, N-phenyl-3-carbazolyl, N-phenyl-4-carbazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 3-isoquinolyl, 1-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 9H-fluorene-2-yl, 9H-fluorene-3-yl, 9H-fluorene-4-yl, 9H-fluorene-1-yl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,3-triazine-5-yl, 1,3,5-triazine-2-yl, 1-dibenzofuryl, 2-dibenzofuryl, 3-dibenzofuryl, 4-dibenzofuryl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1,2,3,4-tetrahydro-5-naphthyl, 1,2,3,4-tetrahydro-6-naphthyl, 1,2,3,4-tetrahydro-1-quinolinyl, diphenylamino, dimethylamino or methylphenylamino, and the phenyl, naphthyl, biphenyl, phenanthryl, N-carbazolyl, pyridyl, quinolyl, isoquinolyl, fluorenyl, pyrimidyl, triazinyl, N-dibenzocarbazolyl or dibenzofuryl of R and R1 through R6 may be further substituted by one or more substituent(s) selected from methyl, phenyl, triphenylsilyl and trimethylsilyl.
The organic electroluminescent compound according to the present invention may be more specifically exemplified as following compounds but is not limited thereto.
The organic electroluminescent compound according to the present invention may be prepared as shown in following Scheme 1.
[Scheme 1]
wherein
A1, A2, B1 through B8, X and R1 through R6 are the same as defined in Chemical Formula 1.
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 compound(s) represented by Chemical Formula 1. The organic layer may include one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s). The dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 2:
[Chemical Formula 2]
M1L101L102L103
wherein
M1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals; and
ligands L101, L102 and L103
are independently selected from the following structures:
wherein, R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen;
R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);
R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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 or a mono- or polycyclic aromatic ring;
R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen;
R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; and
Q represents 
, 
or 
, wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), or each of them 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 represented by Chemical Formula 2 may be exemplified by the compounds having following structures, 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 compounds. 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, 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 compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 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 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. An 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 an 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.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of compound 21
Preparation of compound
1-1
After carbazol (20.5g, 122.7mmol) was dissolved in DMF (200mL), a solution that NaH (6.8g, 177.1mmol, 60%) was dissolved in DMF (200mL) was slowly added thereto. After stirring the mixture for 1 hour, the mixture was slowly added to a solution that 2,4,6-trichloropyrimidin (25g, 136.2mmol) was dissolved in DMF (400mL) and was stirred for 24 hours. When the reaction was completed by slowly adding H2O, the produced solid was filtered and the resultant mixture was heated with EA/MeOH to give a compound 1-1 (25g, 79.5mmol, 50%).
Preparation of compound
1-2
After 2,4,6-trichloropyrimidin 25g(136.2mmol), phenylboronic acid 36.5g(299.3mmol), and tetrakis(triphenylphosphine)palladium (1.11g, 0.96mmol) were dissolved in toluene (408mL), 2.0M Na2CO3 aqueous solution (204 mL) and ethanol (204mL) were added thereto. The mixture was stirred under reflux for 2 hours at 120℃. Upon completion of the reaction, extraction with EA and purification by column chromatography gave a compound 1-2 (25g, 93.7mmol, 69%).
Preparation of compound
21
After the compound 1-2 (21.2g, 79.5mmol) was dissolved in DMF (100mL), a solution that NaH (3.6g, 95.4mmol, 60%) was dissolved in DMF (100mL) was slowly added thereto. After stirring the mixture for 1 hour, a solution that the compound 1-1 (10g, 31.8mmol) was dissolved in DMF (100mL) was slowly added thereto and the mixture was stirred for 24 hours. When the reaction was completed by slowly adding H2O, the produced solid was filtered and recrystallized by heating with EA/MeOH and EA sequentially to give a compound 21 (5g, 7.0mmol, 22%).
Organic electroluminescent Compounds 1 to 39 were prepared according to Preparation Example 1. Table 1 shows 1H NMR and MS/FAB of the prepared organic electroluminescent compounds.
Table 1
| Comp. | 1H NMR(CDCl3, 200 MHz) | MS/FAB | |
| found | calculated | ||
| 1 | δ = 2.73(12H, s), 6.89(1H, s), 7.11(1H, s), 7.25~7.33(3H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m), 8.51~8.55(2H, m) | 456.54 | 456.21 |
| 2 | δ = 7.25~7.33(3H, m), 7.41~7.51(14H, m), 7.63(1H, m), 7.79(8H, m), 7.94(1H, m), 8.12(1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 704.82 | 704.27 |
| 3 | δ = 1.72(16H, m), 2.74(16H, m), 6.88(4H, m), 6.98(4H, m), 7.15(4H, m), 7.25~7.33(3H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 921.18 | 920.46 |
| 4 | δ = 7.25~7.36(7H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7.85(4H, m), 7.94(1H, m), 8.12(1H, m), 8.4(4H, m), 8.51~8.59(6H, m), 10.29(1H, s), 10.51(1H, s) | 708.77 | 708.25 |
| 5 | δ = 1.96(8H, m), 2.76(8H, m), 3.06(8H, m), 5.26(1H, s), 5.48(1H, s), 6.55(4H, m), 6.72(4H, m), 7.05~7.07(8H, m), 7.25~7.33(3H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m), 8.51~8.55(2H, m) | 925.13 | 924.44 |
| 6 | δ = 5.26(1H, s), 5.48(1H, s), 6.63(16H, m), 6.81(8H, m), 7.2~7.33(19H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m), 8.51~8.55(2H, m) | 1069.26 | 1028.44 |
| 7 | δ = 0.25(9H, s), 7.25~7.33(3H, m), 7.41~7.51(13H, m), 7.63(1H, m), 7.77~7.79(8H, m), 7.94(1H, m), 8.12(1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 777.00 | 776.31 |
| 8 | δ = 7.25(1H, m), 7.29(1H, m), 7.33(1H, m), 7.37~7.46(27H, m), 7.61~7.63(2H, m), 7.76~7.79(7H, m), 7.89~7.94(2H, m), 8.12(1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 963.21 | 962.36 |
| 9 | δ = 7.25~7.33(3H, m), 7.41~7.52(18H, m), 7.63(1H, m), 7.79~7.85(8H, m), 7.94(1H, m), 8.12(1H, m), 8.3(4H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 857.01 | 856.33 |
| 10 | δ = 2.34(6H, s), 6.88(1H, m), 7.39~7.51(15H, m), 7.79~7.82(9H, m), 7.99(1H, m), 8.37(1H, s), 8.51(1H, m), 8.59(1H, s), 8.72(1H, m) | 732.87 | 732.30 |
| 11 | δ = 7.25(1H, m), 7.33(1H, m), 7.41~7.51(13H, m), 7.63~7.67(4H, m), 7.79(8H, m), 7.94(1H, m), 8.16(1H, m), 8.37(1H, s), 8.51~8.55(3H, m), 8.59(1H, s) | 754.88 | 754.28 |
| 12 | δ = 7.25(1H, m), 7.33(1H, m), 7.41~7.51(13H, m), 7.57(1H, m), 7.67(2H, m), 7.79(8H, m), 7.94(1H, m), 8.12~8.16(2H, m), 8.37(1H, s), 8.51~8.55(3H, m), 8.59(1H, s) | 754.88 | 754.28 |
| 13 | δ = 7.06(1H, m), 7.41~7.51(13H, m), 7.63~7.67(4H, m), 7.79(8H, m), 7.92(1H, m), 8.16(1H, m), 8.22(1H, m), 8.37(1H, s), 8.51~8.54(2H, m), 8.59(1H, s) | 772.87 | 772.28 |
| 14 | δ = 7.25(1H, m), 7.33(1H, m), 7.4~7.55(15H, m), 7.67(2H, m), 7.79(8H, m), 7.94(1H, m), 8.16(2H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) | 754.88 | 754.28 |
| 15 | δ = 7.25~7.33(6H, m), 7.41~7.51(14H, m), 7.63(2H, m), 7.79(8H, m), 7.94~7.98(3H, m), 8.12(1H, m), 8.37(1H, s), 8.51~8.55(3H, m), 8.59(1H, s) | 870.01 | 869.33 |
| 16 | δ = 1.72(6H, s), 6.55(2H, m), 6.73(2H, m), 6.88(1H, m), 7.02~7.05(4H, m), 7.41(4H, m), 7.51(8H, m), 7.73~7.79(9H, m), 8.37(1H, s), 8.59(1H, s) | 746.90 | 746.32 |
| 17 | δ = 0.66(6H, s), 6.73(4H, m), 6.88(1H, m), 7.21(2H, m), 7.3(2H, m), 7.41(4H, m), 7.51(8H, m), 7.73~7.79(9H, m), 8.37(1H, s), 8.59(1H, s) | 762.97 | 762.29 |
| 18 | δ = 6.38(4H, m), 6.56(4H, m), 6.63(2H, m), 6.81(1H, m), 6.88(1H, m), 7.2(2H, m), 7.41(4H, m), 7.51(8H, m), 7.73~7.79(9H, m), 8.37(1H, s), 8.59(1H, s) | 795.93 | 795.31 |
| 19 | δ = 6.88(1H, m), 6.97(2H, m), 7.16~7.21(6H, m), 7.41(4H, m), 7.51(8H, m), 7.73~7.79(9H, m), 8.37(1H, s), 8.59(1H, s) | 736.88 | 736.24 |
| 20 | δ = 6.59(2H, m), 6.77(2H, m), 6.88~6.92(5H, m), 7.41(4H, m), 7.51(8H, m), 7.73~7.79(9H, m), 8.37(1H, s), 8.59(1H, s) | 720.82 | 720.26 |
| 21 | δ = 7.25~7.33(3H, m), 7.41(4H, m), 7.5~7.51(9H, m), 7.63(1H, m), 7.79(8H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 705.81 | 705.26 |
| 22 | δ = 7.25~7.33(3H, m), 7.41(4H, m), 7.5~7.51(9H, m), 7.63(1H, m), 7.79(8H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m), 8.59(2H, s) | 706.79 | 706.26 |
| 23 | δ = 7.25~7.33(3H, m), 7.41(4H, m), 7.5~7.51(9H, m), 7.63(1H, m), 7.74(1H, s), 7.79(8H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m), 8.59(2H, s) | 705.81 | 705.26 |
| 24 | δ = 7.25~7.33(6H, m), 7.41~7.51(14H, m), 7.58~7.63(6H, m), 7.69(1H, m), 7.77~7.79(6H, m), 7.87(1H, m), 7.94~8(3H, m), 8.12(2H, m), 8.18(1H, m), 8.55(2H, m), 8.59(2H, s), 8.75(1H, s) | 1036.19 | 1035.38 |
| 25 | δ = 7.25~7.33(3H, m), 7.41(4H, m), 7.48~7.63(26H, m), 7.7~7.75(8H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 1010.19 | 1009.39 |
| 26 | δ = 7.32~7.41(8H, m), 7.51(8H, m), 7.66~7.81(19H, m), 7.87~7.89(3H, m), 8(1H, m), 8.18(1H, m), 8.59(2H, s), 8.75(1H, s) | 1038.16 | 1037.35 |
| 27 | δ = 7.25~7.33(3H, m), 7.41~7.51(19H, m), 7.58~7.63(5H, m), 7.69(2H, m), 7.77~7.79(12H, m), 7.87(2H, m), 7.94~8(3H, m), 8.12(1H, m), 8.18(2H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 1188.38 | 1187.44 |
| 28 | δ = 7.41(4H, m), 7.5~7.52(12H, m), 7.69(1H, m), 7.77~7.79(10H, m), 7.86~7.87(3H, m), 7.98~8(7H, m), 8.18(1H, m), 8.45(2H, m), 8.59(2H, s), 8.75(1H, s) | 1070.29 | 1069.30 |
| 29 | δ = 7.25(1H, m), 7.32~7.41(7H, m), 7.51(8H, m), 7.66~7.81(14H, m), 7.87~7.94(3H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 871.98 | 871.31 |
| 30 | δ = 7.25(2H, m), 7.33(2H, m), 7.41~7.51(15H, m), 7.58(2H, m), 7.69(2H, m), 7.77~7.79(10H, m), 7.87(2H, m), 7.94(2H, m), 8.55(2H, m), 8.59(2H, s), 8.75(1H, s) | 947.09 | 946.35 |
| 31 | δ = 7.25(1H, m), 7.33(1H, m), 7.41(4H, m), 7.5~7.52(10H, m), 7.69(1H, m), 7.77~7.79(9H, m), 7.86~7.87(2H, m), 7.94~8(4H, m), 8.45(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 888.05 | 887.28 |
| 32 | δ = 7(1H, m), 7.25~7.26(2H, m), 7.33(1H, m), 7.41(4H, m), 7.51(9H, m), 7.72(1H, m), 7.79(8H, m), 7.94(1H, m), 8.28(1H, m), 8.38(1H, m), 8.5~8.55(2H, m), 8.59(2H, s), 8.75(1H, s) | 782.89 | 782.29 |
| 33 | δ = 7.25(1H, m), 7.33~7.41(6H, m), 7.51(8H, m), 7.79(8H, m), 7.94(1H, m), 8.43(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s), 8.87(1H, m) | 706.79 | 706.26 |
| 34 | δ = 2.34(6H, s), 7.08(1H, s), 7.25(1H, m), 7.33(1H, m), 7.41(4H, m), 7.51(8H, m), 7.79(8H, m), 7.87(1H, s), 7.94(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s) | 733.86 | 733.30 |
| 35 | δ = 7.25(1H, m), 7.33(1H, m), 7.41(4H, m), 7.51(9H, m), 7.79(8H, m), 7.94(1H, m), 8.43(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s), 9.34(1H, m) | 706.79 | 706.26 |
| 36 | δ = 7.25(1H, m), 7.33~7.41(6H, m), 7.51(8H, m), 7.79(8H, m), 7.94(1H, m), 8.43(1H, m), 8.51~8.55(2H, m), 8.59(2H, s), 8.75(1H, s) | 706.79 | 706.26 |
| 37 | δ = 7.38~7.41(6H, m), 7.51(8H, m), 7.79(8H, m), 8.43(2H, m), 8.59(2H, s), 8.75(1H, s), 8.87(2H, m) | 707.78 | 707.25 |
| 38 | δ = 7.06(1H, m), 7.31(1H, m), 7.41(4H, m), 7.51(8H, m), 7.61(1H, m), 7.79(8H, m), 7.92(1H, m), 8.06(1H, m), 8.22(1H, m), 8.59(2H, s), 8.75(1H, s) | 741.79 | 741.25 |
| 39 | δ = 2.34(6H, s), 7.19~7.25(3H, m), 7.33~7.41(6H, m), 7.51(4H, m), 7.6(2H, m), 7.79(6H, m), 7.94(1H, m), 8.43(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s), 8.87(1H, m) | 734.85 | 734.29 |
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material 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 vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
Then, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming 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. A compound 16 was placed in a cell of a vacuum vapor deposition apparatus as a host, and a compound Ir(ppy)3[tris(2-phenylpyridine)iridium] was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 4 to 10 wt%.
Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer. Then, after vapor-depositing lithium quinolate (Liq) of a following structure with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED. Each compound used in the OLED was purified by vacuum sublimation at 10-6torr.
As a result, current of 4.1 mA/cm2 with voltage of 6.7 V flows and it is confirmed that green light of 1308 cd/m2 was emitted.
[Example 2]
An OLED device was manufactured according to the same method as Example 1 except that a compound 19 was used on the electroluminescent layer as a host material and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, current of 4.0 mA/cm2 with voltage of 6.8 V flows and it is confirmed that green light of 1210 cd/m2 was emitted.
[Example 3]
An OLED device was manufactured according to the same method as Example 1 except that a compound 21 was used on the electroluminescent layer as a host material and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, current of 3.8 mA/cm2 with voltage of 7.0 V flows and it is confirmed that green light of 1225 cd/m2 was emitted.
[Example 4]
An OLED device was manufactured according to the same method as Example 1 except that a compound 30 was used on the electroluminescent layer as a host material and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, current of 4.0 mA/cm2 with voltage of 6.7 V flows and it is confirmed that green light of 1090 cd/m2 was emitted.
[Example 5]
An OLED device was manufactured according to the same method as Example 1 except that a compound 35 was used on the electroluminescent layer as a host material and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, current of 4.0 mA/cm2 with voltage of 6.8 V flows and it is confirmed that green light of 1120 cd/m2 was emitted.
[Comparative Example 1]
An OLED device was manufactured in the same manner as Examples 1 and 2 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention was used as a host material in a cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq) was used as the hole blocking layer.
As a result, current of 3.8 mA/cm2 with voltage of 7.5 V flows and it is confirmed that green light of 1000 cd/m2 was emitted.
The organic electroluminescent compounds according to the present invention have excellent properties compared with the conventional material. In addition, the device using the organic electroluminescent compound according to the present invention as a host material has excellent electroluminescent properties and drops driving voltage, thereby increasing power efficiency and reducing power consumption.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1:[Chemical Formula 1]
whereinA1, A2 and B1 through B8 independently represent CR or N;X represents a chemical bond, -C(R11)(R12)-, -N(R13)-, -S-, -O- or -Si(R14)(R15)-;R, R1 through R6 and R11 through R15 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], R29R30R31Si- [wherein R29 through R31 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], (C6-C30)ar(C1-C30)alkyl with or without substituent(s), R32Y- [wherein Y represents S or O, and R32 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)] (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s),or
, or each of them 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, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring; and each of the rings A and B independently represent a (C5-C30)alicyclic ring with or without substituent(s), a (C6-C30)aromatic ring with or without substituent(s), or a (C6-C30)heteroaromatic ring with or without substituent(s);
W represents a chemical bond, -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;R41 through R43 and R51 through R58 are the same as R, R1 through R6 and R11 through R15;the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; andm represents an integer from 1 to 3. - The organic electroluminescent compound according to claim 1, wherein the substituent of R, R1 through R6, R11 through R15, R21 through R32, R41 through R43 and R51 through R58 is one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NRdRe, BRfRg, PRhRi, P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlX-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl, and Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; X represents S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
- The organic electroluminescent compound according to claim 1, whereinis selected from the following structures:
WhereinR is the same as defined in claim 1. - The organic electroluminescent compound according to claim 1, whereinis selected from the following structures:
WhereinR and R11 through R15 independently represent halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or carbazolyl; R may be identical or different; and a and b independently represent an integer from 0 to 4. - The organic electroluminescent compound according to claim 1, wherein R and R1 through R6 independently represent hydrogen, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, 1-naphthyl, 2-naphthyl, 1,2-biphenyl, 1,3-biphenyl, 1-4-biphenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, N-carbazolyl, N-phenyl-1-carbazolyl, N-phenyl-2-carbazolyl, N-phenyl-3-carbazolyl, N-phenyl-4-carbazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 3-isoquinolyl, 1-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 9H-fluorene-2-yl, 9H-fluorene-3-yl, 9H-fluorene-4-yl, 9H-fluorene-1-yl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,3-triazine-5-yl, 1,3,5-triazine-2-yl, 1-dibenzofuryl, 2-dibenzofuryl, 3-dibenzofuryl, 4-dibenzofuryl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1,2,3,4-tetrahydro-5-naphthyl, 1,2,3,4-tetrahydro-6-naphthyl, 1,2,3,4-tetrahydro-1-quinolinyl, diphenylamino, dimethylamino or methylphenylamino, and the phenyl, naphthyl, biphenyl, phenanthryl, N-carbazolyl, pyridyl, quinolyl, isoquinolyl, fluorenyl, pyrimidyl, triazinyl, N-dibenzocarbazolyl or dibenzofuryl of R and R1 through R6 may be further substituted by one or more substituent(s) selected from methyl, phenyl, triphenylsilyl and trimethylsilyl.
- An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 5.
- The organic electroluminescent device according to claim 6, 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 compound(s) according to any of claims 1 to 5 and one or more dopant(s) represented by Chemical Formula 2:[Chemical Formula 2]M1L101L102L103whereinM1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals; andligands L101, L102 and L103 are independently selected from the following structures:
wherein, R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen;R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;R220 through R223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);R224 and R225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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 or a mono- or polycyclic aromatic ring;R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen;R227 through R229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; andQ represents,
or
, wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), or each of them 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 organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compound(s) selected from the group consisting of arylamine compound and styrylaryl amine compounds or one or more metal(s) selected form a 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 according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 7, which is a white-emitting organic electroluminescent device wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2009-0123174 | 2009-12-11 | ||
| KR1020090123174A KR20110066494A (en) | 2009-12-11 | 2009-12-11 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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| WO2011071255A1 true WO2011071255A1 (en) | 2011-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/KR2010/008245 WO2011071255A1 (en) | 2009-12-11 | 2010-11-22 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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| Country | Link |
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| KR (1) | KR20110066494A (en) |
| TW (1) | TW201130805A (en) |
| WO (1) | WO2011071255A1 (en) |
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| TW201130805A (en) | 2011-09-16 |
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