WO2007021117A1 - Green electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Green electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
- Publication number
- WO2007021117A1 WO2007021117A1 PCT/KR2006/003188 KR2006003188W WO2007021117A1 WO 2007021117 A1 WO2007021117 A1 WO 2007021117A1 KR 2006003188 W KR2006003188 W KR 2006003188W WO 2007021117 A1 WO2007021117 A1 WO 2007021117A1
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- WO
- WIPO (PCT)
- Prior art keywords
- compound
- chemical formula
- electroluminescent
- aromatic ring
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 138
- 239000000126 substance Substances 0.000 claims abstract description 62
- 150000001454 anthracenes Chemical class 0.000 claims abstract description 12
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- -1 perilenyl Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 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 14
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 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 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 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 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005561 phenanthryl 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
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 150000003518 tetracenes Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 description 62
- 238000002360 preparation method Methods 0.000 description 35
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 125000005577 anthracene group Chemical group 0.000 description 20
- 235000019557 luminance Nutrition 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 125000004986 diarylamino group Chemical group 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 230000008859 change Effects 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 0 *c(cc1)cc2c1c(*)c(cccc1)c1c2*=C Chemical compound *c(cc1)cc2c1c(*)c(cccc1)c1c2*=C 0.000 description 4
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 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 description 3
- LCKPXWIQVVRLTC-UHFFFAOYSA-N 2,6-dianilinoanthracene-9,10-dione Chemical compound C1(=CC=CC=C1)NC1=CC=2C(C3=CC=C(C=C3C(C2C=C1)=O)NC1=CC=CC=C1)=O LCKPXWIQVVRLTC-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VAJVCZWQJMCWIP-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=2C(C3=CC(=CC=C3C(C2C=C1)=O)C1=CC=CC=C1)=O Chemical compound C1(=CC=CC=C1)C1=CC=2C(C3=CC(=CC=C3C(C2C=C1)=O)C1=CC=CC=C1)=O VAJVCZWQJMCWIP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FZJPZRROCUUMOI-UHFFFAOYSA-N 1-bromofluoranthene Chemical compound C1=CC=C2C3=CC=CC=C3C3=C2C1=CC=C3Br FZJPZRROCUUMOI-UHFFFAOYSA-N 0.000 description 1
- KJGPMAHVCDFRBN-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 KJGPMAHVCDFRBN-UHFFFAOYSA-N 0.000 description 1
- HQUNBWGQFXPVES-UHFFFAOYSA-N 2,7-dichloroanthracene-9,10-dione Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 HQUNBWGQFXPVES-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- WOXNCYQCWDPPFQ-UHFFFAOYSA-N 7,12-dinaphthalen-2-yl-10-phenylbenzo[a]anthracene Chemical compound C1=CC=CC=C1C1=CC=C(C(C=2C=C3C=CC=CC3=CC=2)=C2C(C3=CC=CC=C3C=C2)=C2C=3C=C4C=CC=CC4=CC=3)C2=C1 WOXNCYQCWDPPFQ-UHFFFAOYSA-N 0.000 description 1
- APAJFZPFBHMFQR-UHFFFAOYSA-N Anthraflavic acid Natural products OC1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 APAJFZPFBHMFQR-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-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
- 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
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- LVXHNCUCBXIIPE-UHFFFAOYSA-L disodium;hydrogen phosphate;hydrate Chemical compound O.[Na+].[Na+].OP([O-])([O-])=O LVXHNCUCBXIIPE-UHFFFAOYSA-L 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VWNCIFGADVGFBF-UHFFFAOYSA-N n-(3-methylphenyl)naphthalen-1-amine Chemical compound CC1=CC=CC(NC=2C3=CC=CC=C3C=CC=2)=C1 VWNCIFGADVGFBF-UHFFFAOYSA-N 0.000 description 1
- RQIAICDOHSGNLG-UHFFFAOYSA-N n-(3-methylphenyl)naphthalen-2-amine Chemical compound CC1=CC=CC(NC=2C=C3C=CC=CC3=CC=2)=C1 RQIAICDOHSGNLG-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 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
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/14—Perylene derivatives
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/001—Pyrene dyes
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
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Definitions
- the present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2 , a process for preparing the same, and an organic light emitting diode (OLED) which comprises, as a luminescent region interposed between an anode and a cathode, at least one compound (s) selected from those represented by Chemical Formula 1 or 2 , and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
- OLED organic light emitting diode
- Compound D As green fluorescent material, a coumarin derivative (Compound D) , a quinacridone derivative (Compound E) , DPT (Compound F) and the like have been known.
- Compound D is the structure of C545T that is the most widely used coumarin derivative up to the present. In general, those materials are doped at from several % to not more than 20% concentration by using AIq as the host to form an EL diode.
- 2004-913344 disclosed are some compounds having 1-naphthyl and 9-phenanthryl group at 9- and 10-position of anthracene: but the facts that blue shift phenomenon is involved in a structure having a multicycle of ⁇ -type at 9- and 10-position of anthracene to result in lowered electroluminescent efficiency, and that the inventors could not recognize the electroluminescent efficiency in case that a fused multi-cyclic aromatic ring is actually substituted at 9- and 10- position of anthracene reflect that they did not specifically practiced those compounds.
- US Patent 6,465,115 discloses an organic multi-layer electroluminescent device characterized by a hole transport layer comprising the following organic compounds between the anode and cathode .
- the present inventors now confirmed that the derivatives having a substituent at 2-position of 9, 10-diarylanthracene extraordinarily enhance the electroluminescent property of compounds of Chemical Formula 1 or 2 , and completed the present invention .
- the present inventors found that when at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives is (are) employed as a light-emitting host in luminescent region together with at least one compound of Chemical Formula 1, enhancement of color reproducibility due to improvement of color purity and noticeable increase of electroluminescent efficiency, as well as increased lifetime of device .
- the object of the present invention is to provide a novel organic electroluminescent compound in which a fused multi-cyclic aromatic ring such as naphthalene, anthracene or fluoranthene is substituted at 9- and 10-position of anthracene, and diarylamino groups are directly substituted at 2- and 6-position of anthracene ring, respectively.
- Another object of the present invention is to provide an organic light emitting diode which has a luminescent region employing at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives together with at least one compound of Chemical Formula 1, as the light emitting host.
- Still another object of the invention is to provide an organic electroluminescent compound having excellent color purity, good electroluminescent efficiency and long life of the device, and to provide an OLED containing the novel organic electroluminescent compound as described above.
- the present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2 , and a process for preparing the same .
- Ri and R 2 independently represent a fused multi-cyclic aromatic ring having two or more aromatic rings fused therein, and R 3 to R 6 independently represent an aromatic ring, and each aromatic ring of R 1 to R 6 may be further substituted by a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom or a C5-C7 cycloalkyl group.
- OLED organic light emitting diode
- the present invention relates to an organic light emitting diode (OLED) comprising a first electrode, at least one organic layer and a second electrode in a subsequently laminated form, wherein at least one layer of said organic layers comprise (s) the organic electroluminescent compound of Chemical Formula 1 or 2.
- the present invention relates to an OLED comprising an anode; a cathode; and a luminescent region interposed between said anode and said cathode, wherein said luminescent region comprises at least one organic electroluminescent compound represented by Chemical Formula 1 or 2; and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
- the compounds of Chemical Formula 1 or 2 according to the present invention are characterized by the structure of novel concept with maximized electroluminescent efficiency in green light-emitting diode and lifetime of device which were not expectable with conventional inventions.
- the compounds of Chemical Formula 1 or 2 according to the invention adopted a structure showing an efficient energy transfer mechanism between the host and the dopant, which can reveal electroluminescent property with a reliably high efficiency on the basis of improvement in electron density distribution.
- the structure of the novel compounds according to the present invention can provide a skeletal which can also tune an electroluminescent property with high efficiency in the range from blue to red, not only for green light.
- the invention applies a host having appropriate balance of hole conductivity and electron conductivity, thereby overcoming the problems of conventional materials including low initial efficiency and short lifetime, and ensures the electroluminescent property with high performance having high efficiency and long life for each color.
- Fig. 1 and Fig. 2 showing the electron density distribution of the compound according to the invention wherein amine groups are incorporated to 2- and 6-position of anthracene and 2-naphthyl group as a fused multi-cyclic aromatic group are substituted at 9- and 10-position, and the electron density distribution of the compound wherein aromatic rings are incorporated to 2- and 6 -position of anthracene, respectively, when an amine group is substituted at ⁇ -position (2- and 6- or 7- position) of anthracene, electroluminescent property with high efficiency is obtained due to even electron distribution up to the side branch of core skeletal; while when an aromatic ring is directly positioned on the core skeletal, the electron density of the side branch noticeably falls down.
- electroluminescent materials having at least twice of efficiency of that of conventional material are developed by using a method of directly incorporating amine group at ⁇ -position and a concept of incorporating multi-cyclic aromatic ring at 9- and 10-position of core anthracene in order to overcome the problems mentioned above.
- the compounds represented by Chemical Formula 1 or 2 according to the present invention are characterized in that a diarylamine group having an aromatic ring at the ⁇ -position of anthracene is directly substituted, and a fused multi-cyclic aromatic ring with two or more aromatic ring fused is substituted for Ri and R 2 at 9- and 10-position.
- the fused multi- cyclic aromatic ring independently represents naphthyl , anthryl, fluoranthenyl, pyrenyl , fluorenyl, biphenyl and perilenyl group.
- Groups R 3 to R 6 that are substituted for amine substituted at ⁇ - position of anthracene independently represent phenyl, naphthyl, anthryl, phenanthryl, fluorenyl, fluoranthenyl, pyrenyl, perilenyl, naphthacenyl or biphenyl group.
- the fused multi-cyclic aromatic ring of Ri and R 2 in Chemical Formula 1 or 2 is independently selected from 2 -naphthyl, 2 -anthryl, 2-fluoranthenyl , 1-pyrenyl, 2- fluorenyl, 4 -biphenyl and 3 -perilenyl group. Due to the substitution of said fused multi-cyclic aromatic ring at a certain position, optimal overlap of ⁇ -electrons of the fused multi-cyclic aromatic ring with other molecules can be achieved, and the selection of the position for the fused multi-cyclic aromatic ring compound also is an important feature of the invention.
- the aromatic rings of R 3 to R 6 independently may have a substituent selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom and C5- C7 cycloalkyl group.
- each aromatic group of Ri to R 6 preferably is substituted by methyl, t -butyl or methoxy group.
- the compound represented by Chemical Formula 1 or 2 according to the present invention can be prepared as shown in Reaction Scheme 1: 2 , 6-dihaloanthraquinone (2,6-DHAQ) or 2,7- dihaloanthraquinone is reacted with diarylamine to obtain bis (diarylamino) anthraquinone (BDAAQ) ; BDAAQ is then treated with lithium compound of fused multi-cyclic aromatic compound to give dihydroanthracenediol compound (DHAD) ; DHAD is dehydrated to completely form the anthracene skeletal.
- the present invention relates to an organic light emitting diode (OLED) comprising a first electrode, at least one organic layer and a second electrode in a subsequently laminated form, wherein at least one layer of said organic layers comprise (s) the organic electroluminescent compound of Chemical Formula 1 or 2.
- OLED organic light emitting diode
- the present invention relates to an organic light emitting diode comprising an anode; a cathode; and a luminescent region interposed between said anode and said cathode, wherein said luminescent region comprises at least one organic electroluminescent compound of Chemical Formula 1 or 2 ; and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
- the luminescent region means the layer where light emitting occurs.
- the layer may be single layer or multiple layers with two or more layers laminated.
- the host-dopant which can be constructed with a doping concentration of 2 to 5%, has very excellent conductivity with regard to the holes and electrons as compared to other conventional host materials, and very excellent material stability to result in improving the lifetime as well as electroluminescent efficiency.
- the anthracene derivatives or benz [a] anthracene derivatives contained with at least one organic electroluminescent compound of Chemical Formula 1 or 2 in said luminescent region include the compounds represented by Chemical Formula 3 or 4 : [Chemical Formula 3]
- each of Rn and Ri 2 independently represents a C6- C20 aromatic ring or a fused multi-cyclic aromatic ring
- Ri 3 represents a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom, a C5-C7 cycloalkyl group, or a C6-C20 aromatic ring or a fused multi-cyclic aromatic ring
- each aromatic ring of Rn to R 13 may have further substituent (s) of a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom or a C5-C7 cycloalkyl group.
- the compounds represented by Chemical Formula 3 or 4 may be exemplified by the compounds in which Rn to Ri 3 independently represent phenyl, 2-naphthyl, 2-anthryl, 2-fluoranthenyl , 1- pyrenyl , 2-fluorenyl, 4-biphenyl and 3-perilenyl group.
- the anthracene derivatives include compounds of following formulas :
- Fig. 1 illustrates distribution of electron density of the compound according to the present invention.
- Fig. 2 illustrates distribution of electron density of the compound wherein aromatic rings are incorporated at 2- and 6- position of anthracene.
- Fig. 3 shows the change of electroluminescent efficiency versus luminance of an OLED employing AIq and C545T as the luminescent materials.
- Fig. 4 shows the change of electroluminescent efficiency versus luminance of an OLED from Comparative Example 2.
- Fig. 5 shows the change of luminance versus operation voltage of an OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials.
- Fig. 6 shows the change of electroluminescent efficiency versus luminance of OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials.
- Fig. 7 is an EL spectrum of an OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials.
- Fig. 8 shows the change of CIE coordinate versus luminance between the OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials and the OLED from Comparative Example 1 or 2.
- Fig. 9 shows the life curves of the OLED from Example 1 according to the present invention and the OLED from Comparative Example 1 or 2.
- Fig. 10 shows the change of electroluminescent efficiency versus luminance of the OLEDs employing Compound 23 and Compound 1 of the present invention.
- Fig. 11 shows the change of CIE coordinate versus luminance of the OLEDs employing Compound 23 and Compound 1 of the present invention as the electroluminescent material .
- the diol compound (1.3 g, 1.71 mmol) thus obtained was added to 30 mL of acetone, and potassium iodide (1.6 g, 7.8 mmol) and sodium hydrogen phosphate monohydrate (2.0 g, 14.5 mmol) were added thereto.
- the resultant mixture was heated under reflux for
- An OLED having the structure employing the electroluminescent material having the structure employing the electroluminescent material.
- a transparent electrode ITO thin film (15 ⁇ /D) obtained from a glass for OLED was subjected to ultrasonic washing by trichloroethylene, acetone, ethanol and distilled water, subsequently, and stored in isopronanol before use.
- an ITO substrate was equipped in a substrate folder of vacuum vapor deposition apparatus, and 4 , 4 ' , 4" -tris (N, N- (2- naphthyl) -phenylamino) triphenylamine (2-TNATA) represented by following structural formula 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. Electric current was applied to the cell to evaporate 2-TNATA to vapor-deposit a hole injection layer having 60 nm of thickness on the ITO substrate.
- NPB N, N' -bis ( ⁇ -naphthyl) -N, N' -diphenyl-4 , 4 ' - diamine
- an electroluminescent layer was vapor-deposited thereon as follows. In one cell of the vacuum vapor deposition apparatus, charged was 7 , 12-di (2-naphthyl) -10-phenyl-benz (a) anthracene
- DNPBA Compound 34
- a compound according to the present invention (ex. Compound 4) as a dopant, and the two substances are evaporated at a different rate to dope with 2 mol% to 5 mol%, to vapor-deposit an electroluminescent layer (4) having 30 nm of thickness on said hole transport layer.
- AIq represented by following structural formula
- Liq lithium quinolate
- Al cathode was vapor-deposited with 150 nm of thickness by using another vapor deposition apparatus to manufacture an OLED.
- Each compound for individual material was purified by vacuum sublimation under 10 "6 torr, and employed as an electroluminescent material for OLED.
- an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedure as described in Example 1, and an Al cathode was vapor-deposited by using another vacuum vapor deposition apparatus with a thickness of 150 nm, to manufacture an OLED.
- a hole injecting layer and hole transport layer were created according to the same procedure as described in Example 1, and DNPBA was charged as an electroluminescent host material to another cell of said vacuum vapor deposition apparatus, while Compound G was charged to still another cell.
- the two substances are doped with from 2 to 5 mol% concentration based on DNPBA by- evaporating with different rates, to vapor-deposit an electroluminescent layer having 30 nm of thickness on said hole transport layer.
- an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedure as described in Example 1, and an Al cathode was vapor-deposited by using another vacuum vapor deposition apparatus with a thickness of 150 nm, to manufacture an OLED.
- Electroluminescent efficiency of an OLED comprising the organic electroluminescent compounds prepared from Example 1 and Comparative Example 1 according to the present invention and a conventional electroluminescent compound was measured at 5,000 cd/m 2 and 20,000 cd/m 2 , respectively, of which the results are shown in Table 1. Since the luminescent properties in the range of high luminance are very importance in case of green electroluminescent material, in particular, the data of luminance as high as about 20,000 cd/m 2 was also attached in order to reflect those properties. [Table 1]
- Fig. 3 is an electroluminescent efficiency curve of
- FIG. 4 is an electroluminescent efficiency curve with Compound G being employed as the electroluminescent material.
- Fig. 5 and Fig. 6 shows luminance-voltage and electroluminescent efficiency- luminance curve, respectively.
- the fact that the high performance electroluminescent material according to the present invention have not more than 3 cd/A of lowering of efficiency even at a luminance as high as about 20,000 cd/m 2 indicates that the electroluminescent material of the present invention has excellent material properties even maintained at a high luminance .
- Table 1 shows that C545T also exhibits good luminescent color property, while Compound G exhibits luminescent color with short-wavelength shift, which means somewhat poor luminescent color property as compared to the materials according to the present invention.
- Fig. 6 is an EL spectrum of electroluminescent material according to the present invention
- Fig. 7 compares the luminescent color of Compound 4 according to the present invention and that of Comparative Example 1. They show good luminescent color properties without showing significant difference from conventional pure green electroluminescent material. They show typical green electroluminescent peak at 520 nm, and the material according to the invention shows no substantial deterioration of properties of color purity as the electroluminescent efficiency increases.
- Fig. 9 that is a life curve at the luminance of 10,000 cd/m 2 , shows that the life property of the material of the invention is excellent as compared to that of conventional electroluminescent material.
- the material according to the present invention does not have property of rapid lowering of initial luminance as was found in conventional material.
- Relative luminances after 800 hours of operation are 63%, 73% and 88% for C545T, Compound G and Example 1, respectively, which implies actual improvement of 2 to 5 times of life in terms of half life of luminance.
- a hole injecting layer and hole transport layer were created according to the same procedure as described in Example 1, and Compound (18) (or Compound (19) or Compound (23), or Compound (24), or Compound (25)) was charged as an electroluminescent host material to another cell of said vacuum vapor deposition apparatus.
- Compound (1) or Compound (5), or Compound (13) was charged to still another cell.
- the two substances are doped by evaporating with different rates, to vapor-deposit an electroluminescent layer having 30 nm of thickness on said hole transport layer.
- the doping concentration at this time was preferably from 2 to 5 mol% on the basis of the amount of the electroluminescent host material .
- the materials according to the present invention showed improvement at low luminance as well as high luminance, so that they can give advantageous properties in both passive- and active-type organic light emitting diode.
- the properties as described above are advantageous in terms of electric power consumption as compared to the case employing conventional 9, 10-diarylanthracene as the electroluminescent host material, to afford the present invention of many chances to be practiced.
- the organic electroluminescent compounds according to the present invention have good electroluminescent efficiency and excellent life properties, thereby providing OLED having very long lifetime of operation.
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Abstract
The present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2 , a process for preparing the same, and an organic light emitting diode (OLED) which comprises, as a luminescent region interposed between an anode and a cathode, at least one compound (s) selected from those represented by Chemical Formula 1 or 2 , and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives. The electroluminescent compound according to the present invention is a green electroluminescent compound having maximized electroluminescent efficiency and lifetime of device.
Description
Green electroluminescent compounds and organic electroluminescent device using the same
Field of the Invention
The present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2 , a process for preparing the same, and an organic light emitting diode (OLED) which comprises, as a luminescent region interposed between an anode and a cathode, at least one compound (s) selected from those represented by Chemical Formula 1 or 2 , and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
[Chemical Formula 1]
[Chemical Formula 2]
Background of the Related Art
The most important matter in developing an OLED having high efficiency and long life is development of electroluminescent material of high performance. In view of current development of electroluminescent material, green electroluminescent materials show superior electroluminescent property to red or blue
electroluminescent materials. However, conventional green electroluminescent materials still have many problems to achieve manufacturing panels of large scale with low power consumption. In view of practical efficiency and life, various kinds of materials for green have been reported up to now. Though they show from 2 to 5 times of electroluminescent property as compared to red or blue electroluminescent materials, development of green electroluminescent material become a burden with the improvement of properties of red or blue electroluminescent material. In the meanwhile, enhancement of lifespan of the green material is still insufficient, so that a green electroluminescent material having long life is seriously required.
As green fluorescent material, a coumarin derivative (Compound D) , a quinacridone derivative (Compound E) , DPT (Compound F) and the like have been known. Compound D is the structure of C545T that is the most widely used coumarin derivative up to the present. In general, those materials are doped at from several % to not more than 20% concentration by using AIq as the host to form an EL diode.
Compound D Compound E Compound F
In Japanese Patent Laid-Open No. 2001-131541, disclosed are bis (2 , 6-diarylamino) -9 , 10-diphenylanthracene derivatives
represented by following Chemical Formula G, in which diarylamino groups are directly substituted at 2- and 6-position of anthracene, respectively.
Compound G Compound H Japanese Patent Laid-Open No. 2003-146951 disclosing the compounds for hole transport does not describe those compounds wherein diarylamino groups are directly substituted at 2- and 6- position, but having phenyl groups at 9- and 10-position of anthracene; and Japanese Patent Laid-Open No. 2003-146951 recognizes that Compound H having diarylamino groups directly substituted at 2- and 6-position of anthracene ring shows poor electroluminescent efficiency. In view of these facts, the invention of Japanese Patent Laid-Open No. 2003-146951 does not recognize the compounds other than those having phenyl substituents at 9- and 10- position of anthracene. In order to overcome the problems described above, Japanese Patent Laid-Open No. 2003-146951 has suggested an electroluminescent compound represented by following Chemical Formula I having about twice of the electroluminescent efficiency, on the basis of recognizing the fact that the electroluminescent efficiency is enhanced if one diarylamino group is substituted at 2 -position of anthracene and an aryliminophenyl group is substituted at 6-position.
Compound I
However, the above-suggested compound has problems of low hole transport property and insufficient luminance, though the electroluminescent efficiency has been increased. Those materials are not employed as electroluminescent material with limitation to be applied as practical electroluminescent material, because Compound I emits light of light-blue color with low electroluminescent efficiency. Japanese Patent Laid-Open No. 2004-91334 suggested an organic electroluminescent compound represented by following Chemical Formula J having low ionization potential and excellent hole transport property with overcoming low electroluminescent efficiency of the conventional compounds, by further substituting the aryl group of the diarylamino group with another diarylamino group, though said diarylamino group being already directly substituted to anthracene.
Compound J
Though the compounds suggested by Japanese Patent Laid-Open No. 2004-91334, applied as a hole transport layer, could lower the ionization potential and enhance the hole transport property due to many amine functional groups, they have problem of short lifetime of operation as a hole transport layer because of multiple amine functional groups. In the detailed description of the invention of Japanese Patent Laid-Open No. 2004-91334, disclosed are some compounds having 1-naphthyl and 9-phenanthryl group at 9- and 10-position of anthracene: but the facts that blue shift phenomenon is involved in a structure having a multicycle of α-type at 9- and 10-position of anthracene to result in lowered electroluminescent efficiency, and that the inventors could not recognize the electroluminescent efficiency in case that a fused multi-cyclic aromatic ring is actually substituted at 9- and 10- position of anthracene reflect that they did not specifically practiced those compounds.
In the meanwhile, US Patent 6,465,115 discloses an organic multi-layer electroluminescent device characterized by a hole transport layer comprising the following organic compounds between the anode and cathode .
Compound K Compound L
However, US Patent 6,465,115 did not employed Compound K and Compound L in the luminescent region, and could not confirm the properties of those materials in the luminescent region. In particular, they could not recognize that the derivatives having the substituent according to the present invention at 2 -position provide far better electric property than the derivatives simply having aromatic substituents at 9- and 10-position of anthracene do.
The present inventors now confirmed that the derivatives having a substituent at 2-position of 9, 10-diarylanthracene extraordinarily enhance the electroluminescent property of compounds of Chemical Formula 1 or 2 , and completed the present invention .
Surprisingly, the present inventors found that simple introduction of a multi-cyclic aromatic ring such as naphthalene to 9- and 10-position of anthracene overcomes the problems of the conventional hole transport materials including lowering of electroluminescent efficiency, shortening of operation life of device and increasing of ionization potential, even though diarylamino groups are directly substituted at 2- and 6-position of the anthracene ring; and they incorporated the construction that applies those compounds as electroluminescent material, to complete the invention. This eventually was not able to be recognized in any prior invention including Japanese Patent Laid- Open No. 2003-146951 and 2004-91334. In addition, the present inventors found that when at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives is (are) employed as a light-emitting host in luminescent region together with at least one compound of
Chemical Formula 1, enhancement of color reproducibility due to improvement of color purity and noticeable increase of electroluminescent efficiency, as well as increased lifetime of device .
Disclosure Technical problem
The object of the present invention is to provide a novel organic electroluminescent compound in which a fused multi-cyclic aromatic ring such as naphthalene, anthracene or fluoranthene is substituted at 9- and 10-position of anthracene, and diarylamino groups are directly substituted at 2- and 6-position of anthracene ring, respectively. Another object of the present invention is to provide an organic light emitting diode which has a luminescent region employing at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives together with at least one compound of Chemical Formula 1, as the light emitting host. Still another object of the invention is to provide an organic electroluminescent compound having excellent color purity, good electroluminescent efficiency and long life of the device, and to provide an OLED containing the novel organic electroluminescent compound as described above.
Technical solution
The present invention relates to organic electroluminescent compounds represented by Chemical Formula 1 or 2 , and a process for preparing the same .
[Chemical Formula 1]
[Chemical Formula 2 ]
In the Chemical Formula 1 and 2, Ri and R2 independently represent a fused multi-cyclic aromatic ring having two or more aromatic rings fused therein, and R3 to R6 independently represent an aromatic ring, and each aromatic ring of R1 to R6 may be further substituted by a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom or a C5-C7 cycloalkyl group. In addition, the present invention relates to an organic light emitting diode (OLED) comprising a first electrode, at least one organic layer and a second electrode in a subsequently laminated form, wherein at least one layer of said organic layers comprise (s) the organic electroluminescent compound of Chemical Formula 1 or 2. Further, the present invention relates to an OLED comprising an anode; a cathode; and a luminescent region interposed between said anode and said cathode, wherein said luminescent region comprises at least one organic electroluminescent compound represented by Chemical Formula 1 or 2; and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
Other and further objects, features and advantages of the
invention will appear more fully from the following description.
The compounds of Chemical Formula 1 or 2 according to the present invention are characterized by the structure of novel concept with maximized electroluminescent efficiency in green light-emitting diode and lifetime of device which were not expectable with conventional inventions.
The compounds of Chemical Formula 1 or 2 according to the invention adopted a structure showing an efficient energy transfer mechanism between the host and the dopant, which can reveal electroluminescent property with a reliably high efficiency on the basis of improvement in electron density distribution. The structure of the novel compounds according to the present invention can provide a skeletal which can also tune an electroluminescent property with high efficiency in the range from blue to red, not only for green light. Beyond the concept of using a host material with high electric conductivity such as AIq, the invention applies a host having appropriate balance of hole conductivity and electron conductivity, thereby overcoming the problems of conventional materials including low initial efficiency and short lifetime, and ensures the electroluminescent property with high performance having high efficiency and long life for each color.
As can be seen from Fig. 1 and Fig. 2 showing the electron density distribution of the compound according to the invention wherein amine groups are incorporated to 2- and 6-position of anthracene and 2-naphthyl group as a fused multi-cyclic aromatic group are substituted at 9- and 10-position, and the electron density distribution of the compound wherein aromatic rings are
incorporated to 2- and 6 -position of anthracene, respectively, when an amine group is substituted at β-position (2- and 6- or 7- position) of anthracene, electroluminescent property with high efficiency is obtained due to even electron distribution up to the side branch of core skeletal; while when an aromatic ring is directly positioned on the core skeletal, the electron density of the side branch noticeably falls down. This illustrates that amine groups should be directly incorporated to the core skeletal in order to get electroluminescent property with high efficiency. These results show that the electroluminescent material according to the prior art, in which an aromatic ring is employed as a spacer only for the purpose of tuning the light -emitting wavelength, inevitably has the limitation in improving the electroluminescent efficiency. According to the present invention, electroluminescent materials having at least twice of efficiency of that of conventional material are developed by using a method of directly incorporating amine group at β-position and a concept of incorporating multi-cyclic aromatic ring at 9- and 10-position of core anthracene in order to overcome the problems mentioned above.
As described heretofore, in case of Compound G and Compound
H exemplified in Japanese Patent Laid-Open No. 2003-146951 having similar structure to that of Chemical Formula 1 according to the present invention, wherein diarylamino groups are directly substituted at 2- and 6-position, respectively, and phenyl groups are substituted at 9- and 10-position, the problem is low electroluminescent efficiency. According to the present inventors, the problem is caused by disadvantageous structure for energy transfer with the host, and said compounds suggested by
prior inventions inevitably have limitation that they cannot improve the properties of dopant at all no matter how good the property of the host is.
Compound G Compound H On the basis of research results as described above, the inventors found that, even though the longer wavelength shift property due to simple overlap of molecules cannot be overcome with the size and 3 -dimensional structural property like phenyl, when diarylamino groups are directly substituted at 2- and 6- position of anthracene, respectively, and phenyl groups at 9- and 10-position, the overlap of π-electron with other molecules are very efficiently achieved by incorporating a fused multi-cyclic aromatic ring (at least naphthalene) at 9- and 10-position of anthracene in the compounds of Chemical Formula 1 or 2 according to the present invention, thereby much enhancing the energy transfer properties. The present invention is established on the basis of such discoveries.
Thus, the compounds represented by Chemical Formula 1 or 2 according to the present invention are characterized in that a diarylamine group having an aromatic ring at the β-position of anthracene is directly substituted, and a fused multi-cyclic aromatic ring with two or more aromatic ring fused is substituted for Ri and R2 at 9- and 10-position. Preferably, the fused multi-
cyclic aromatic ring independently represents naphthyl , anthryl, fluoranthenyl, pyrenyl , fluorenyl, biphenyl and perilenyl group. Groups R3 to R6 that are substituted for amine substituted at β- position of anthracene independently represent phenyl, naphthyl, anthryl, phenanthryl, fluorenyl, fluoranthenyl, pyrenyl, perilenyl, naphthacenyl or biphenyl group.
More preferably, the fused multi-cyclic aromatic ring of Ri and R2 in Chemical Formula 1 or 2 is independently selected from 2 -naphthyl, 2 -anthryl, 2-fluoranthenyl , 1-pyrenyl, 2- fluorenyl, 4 -biphenyl and 3 -perilenyl group. Due to the substitution of said fused multi-cyclic aromatic ring at a certain position, optimal overlap of π-electrons of the fused multi-cyclic aromatic ring with other molecules can be achieved, and the selection of the position for the fused multi-cyclic aromatic ring compound also is an important feature of the invention.
In order to improve electroluminescent properties of the compounds according to the present invention, the aromatic rings of R3 to R6 independently may have a substituent selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a halogen atom and C5- C7 cycloalkyl group. Preferably, each aromatic group of Ri to R6 preferably is substituted by methyl, t -butyl or methoxy group.
Among the compounds represented by Chemical Formula 1 or 2 according to the present invention, compounds having one of the following chemical structures are preferably mentioned.
The compound represented by Chemical Formula 1 or 2 according to the present invention can be prepared as shown in Reaction Scheme 1: 2 , 6-dihaloanthraquinone (2,6-DHAQ) or 2,7- dihaloanthraquinone is reacted with diarylamine to obtain bis (diarylamino) anthraquinone (BDAAQ) ; BDAAQ is then treated with lithium compound of fused multi-cyclic aromatic compound to give dihydroanthracenediol compound (DHAD) ; DHAD is dehydrated to completely form the anthracene skeletal.
[Reaction Scheme 1]
DHAD Chemical Formula 1
In addition, the present invention relates to an organic light emitting diode (OLED) comprising a first electrode, at
least one organic layer and a second electrode in a subsequently laminated form, wherein at least one layer of said organic layers comprise (s) the organic electroluminescent compound of Chemical Formula 1 or 2. Further, the present invention relates to an organic light emitting diode comprising an anode; a cathode; and a luminescent region interposed between said anode and said cathode, wherein said luminescent region comprises at least one organic electroluminescent compound of Chemical Formula 1 or 2 ; and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
The luminescent region means the layer where light emitting occurs. The layer may be single layer or multiple layers with two or more layers laminated. According to the construction of the invention, when the host-dopant is employed together with the compound of Chemical Formula 1 or 2 , noticeable improvement of electroluminescent efficiency could be confirmed due to the luminescent host, on the contrary of the case using the compound of Chemical Formula 1 or 2 only. The host-dopant, which can be constructed with a doping concentration of 2 to 5%, has very excellent conductivity with regard to the holes and electrons as compared to other conventional host materials, and very excellent material stability to result in improving the lifetime as well as electroluminescent efficiency.
Thus it is understand that if a compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives is employed as a luminescent host, electric disadvantage of the compound of Chemical Formula 1 or 2 of the invention may be significantly complemented.
The anthracene derivatives or benz [a] anthracene derivatives
contained with at least one organic electroluminescent compound of Chemical Formula 1 or 2 in said luminescent region include the compounds represented by Chemical Formula 3 or 4 : [Chemical Formula 3]
[Chemical Formula 4]
The compounds represented by Chemical Formula 3 or 4 may be exemplified by the compounds in which Rn to Ri3 independently represent phenyl, 2-naphthyl, 2-anthryl, 2-fluoranthenyl , 1- pyrenyl , 2-fluorenyl, 4-biphenyl and 3-perilenyl group. The anthracene derivatives include compounds of following formulas :
Brief Description of Drawings
Fig. 1 illustrates distribution of electron density of the compound according to the present invention.
Fig. 2 illustrates distribution of electron density of the compound wherein aromatic rings are incorporated at 2- and 6- position of anthracene.
Fig. 3 shows the change of electroluminescent efficiency versus luminance of an OLED employing AIq and C545T as the luminescent materials.
Fig. 4 shows the change of electroluminescent efficiency
versus luminance of an OLED from Comparative Example 2.
Fig. 5 shows the change of luminance versus operation voltage of an OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials. Fig. 6 shows the change of electroluminescent efficiency versus luminance of OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials.
Fig. 7 is an EL spectrum of an OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials.
Fig. 8 shows the change of CIE coordinate versus luminance between the OLED employing Compound 4 according to the present invention and DNPBA as the electroluminescent materials and the OLED from Comparative Example 1 or 2. Fig. 9 shows the life curves of the OLED from Example 1 according to the present invention and the OLED from Comparative Example 1 or 2.
Fig. 10 shows the change of electroluminescent efficiency versus luminance of the OLEDs employing Compound 23 and Compound 1 of the present invention.
Fig. 11 shows the change of CIE coordinate versus luminance of the OLEDs employing Compound 23 and Compound 1 of the present invention as the electroluminescent material .
Mode for invention Examples
The present invention is further described with respect to the compounds according to the invention, a process for preparing the same and the electroluminescent properties of the device
employing the same by referring to representative compounds according to the present invention, which are provided for illustration only and are not intended to be limiting in any way. [Preparation Example 1] Preparation of Compound (1) (Chemical Formula 1: R1 = R2 = 2-naphthayl, R3 = R4 = R5 = R6 = phenyl)
In dry toluene, dissolved were 2 , 6-dichloroanthraquinone (1.0 g, 3.6 mmol) and diphenylamine (1.3 g, 7.7 mmol) , and palladium acetate (Pd (OAc) 2) (2.4 g, 24.4 mmol), tri(t-butyl) phosphine (P(t-Bu)3) (0.2 mL, 1.9 mmol) and sodium t-butoxide (t- BuONa) (0.93 g, 9.7 mmol) were added thereto. The resultant mixture was heated under reflux at 110 "C for 3 days. When the reaction was completed, 10 mL of distilled water was added, and the mixture was stirred for 30 minutes. The solid generated was filtered, washed with solvent such as acetone and THF, dried and recrystallized from methylene chloride to give bis (2,6- diphenylamino) anthraquinone (1.1 g, 2.0 mmol, yield: 56%).
Diethyl ether solution (5 mL) of 2-naphthyllithium which had been previously prepared by using diphenylamine (0.74 g, 4.4 mmol) and n-buthyllithium (n-BuLi) (1.8 mL, 4.5 mmol, 2.5 M in hexane) was slowly added to a solution of bis (2,6- diphenylamino) anthraquinone obtained as described above (1.1 g, 2.0 mmol) in dry THF (30 mL) at -78 °C under nitrogen atmosphere. The reaction mixture was stirred for 2 hours at the same temperature, and warmed to ambient temperature, before stirring for 12 hours. Saturated aqueous ammonium chloride solution (30 mL) was added thereto, and the resultant mixture was stirred for 2 hours to complete the reaction. The resultant solid was filtered, washed with acetone and dried to give 2,6-
bis (diphenylamino) -9, 10- [di- (2-naphthyl) ] -9, 10-dihydro-9 , 10- anthracenediol (1.3 g, 1.7 mmol , yield: 85%).
The diol compound (1.3 g, 1.71 mmol) thus obtained was added to 30 mL of acetone, and potassium iodide (1.6 g, 7.8 mmol) and sodium hydrogen phosphate monohydrate (2.0 g, 14.5 mmol) were added thereto. The resultant mixture was heated under reflux for
12 hours. When the reaction was completed, an equivalent volume of distilled water was added thereto to form precipitate, which was then filtered, washed with water and acetone to give solid product. After recrystallization from THF, the title compound
(1) (0.68 g, 0.89 mmol, yield: 52%) was obtained.
1H NMR(200MHz, CDCl3): δ 6.46(d, 8H), 6.65-6.75(m, 8H), 7.0(m, 8H), 7.3 (m, 4H), 7.5-7.6(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H) MS/FAB: 764 (found) , 764.98 (calculated)
[Preparation Example 2] Preparation of Compound (2) (Chemical Formula 1: R1 = R2 = R3 = R5 = 2-naphthayl, R4 = R6 = phenyl)
The same procedure as described in Preparation Example 1 was repeated but using N-phenyl-2-naphthylamine (1.7 g, 7.8 mmol) to obtain Compound (2) (0.53 g, 0.61 mmol, overall yield: 17%).
1H NMR (200MHz, CDCl3): δ 6.45(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7.15(m, 6H), 7.2-7.3(m, 6H), 7.45-7.6(m, 10H), 7.65- 7.8 (m, 6H) , 7.9 (s, 2H) MS/FAB: 864 (found), 865.10 (calculated)
[Preparation Example 3] Preparation of Compound (3) (Chemical Formula 1: R1 = R2 = 2-naphthyl, R3 = R5 = 1-naphthyl, R4 = R6 = phenyl)
The same procedure as described in Preparation Example 1
was repeated but using N-phenyl-1-naphthylamine (1.7 g, 7.8 mmol) to obtain Compound (3) (0.41 g, 0.47 mmol, overall yield: 13%) .
1H NMR (200MHz, CDCl3): δ 6.45(d, 4H), 6.5(d, 2H), 6.6(t, 2H), 6.75-6.8(m, 4H), 7.0-7.05(m, 4H), 7.15-7.2(m, 4H), 7.3-7.35(m, 8H), 7.55-7.8(m, 14H), 7.9(s, 2H)
MS/FAB: 864 (found), 865.10 (calculated)
[Preparation Example 4] Preparation of Compound (4) (Chemical Formula 1: R1 = R2 = R3 = R4 = R5 = R6 = 2-naphthyl)
The same procedure as described in Preparation Example 1 was repeated but using di (2-naphthyl) amine (2.1 g, 7.8 mmol) to obtain Compound (4) (0.52 g, 0.54 mmol, overall yield: 15%) .
1H NMR(200MHz, CDCl3): δ 6.75-6.8(m, 12H), 7.0-7.1(m, 4H), 7.2-7.35(m, 8H), 7.45-7.6(m, 16H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 964 (found), 965.22 (calculated) [Preparation Example 5] Preparation of Compound (5) (Chemical Formula 1 : R1 = R2 = 2-naphthyl, R3 = R5 = phenyl, R4 = R6 = 3-methoxyphenyl)
The same procedure as described in Preparation Example 1 was repeated but using 3-methoxyphenylamine (1.53 g, 7.7 mmol) to obtain Compound (5) (1.0 g, 1.21 mmol, overall yield: 34%).
1H NMR(200MHz, CDCl3): δ 3.75(s, 6H), 5.95-6.05(m, 4H), 6.15(d, 2H), 6.45(d, 4H), 6.6(t, 2H), 6.75-7.05(m, 10H), 7.3(m, 4H), 7.5-7.55(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 824 (found), 825.03 (calculated) [Preparation Example 6] Preparation of Compound (6) (Chemical Formula 1: R1 = R2 = R3 = R5 = 2-naphthyl, phenyl, R4 = R6 = 3 -methylphenyl)
The same procedure as described in Preparation Example 1 was repeated but using N-m-tolyl-2-naphthylamine (1.8 g, 7.7
mmol) to obtain Compound (6) (0.61 g, 0.68 mmol, overall yield: 19%) .
1H NMR (200MHz, CDCl3): δ 2.3(s, 6H), 6.25-6.30(t, 4H), 6.4(d, 2H), 6.75-6.9(m, 10H), 7.1 (m, 2H), 7.2-7.3(m, 6H), 7.4-7.55(m, 10H), 7.65-7.8(m, 6H), 7.9(s, 2H)
MS/FAB: 892 (found), 893.15 (calculated)
[Preparation Example 7] Preparation of Compound (7) (Chemical Formula 1: Ri = R2 - 2-naphthyl, R3 = R5 = 1-naphthyl, phenyl, R4 = R6 = 3 -methylphenyl) The same procedure as described in Preparation Example 1 was repeated but using N-m-tolyl-1-naphthylamine (1.8 g, 7.7 mmol) to obtain Compound (7) (0.38 g, 0.43 mmol, overall yield: 12%) .
1H NMR(200MHz, CDCl3): δ 2.3(s, 6H), 6.25-6.3(t, 4H), 6.4- 6.5(m, 4H), 6.75-6.9(m, 6H), 7.15(t, 4H), 7.3(m, 8H), 7.5-7.8(m, 14H) , 7.9 (s, 2H)
MS/FAB: 892 (found), 893.15 (calculated)
[Preparation Example 8] Preparation of Compound (8) (Chemical Formula 1: Ri = R2 = 1-fluoranthenyl , R3 = R5 = phenyl, R4 = R6 = 2-naphthyl)
The same procedure as described in Preparation Example 1 was repeated but using bis (2 , 6-diphenylamino) anthraquinone (1.16 g, 1.8 mmol) prepared from Preparation Example 2 with 1- bromofluoranthene (1.1 g, 3.9 mmol) to obtain Compound (8) (0.77 g, 0.76 mmol, overall yield: 21%).
1H NMR (200MHz, CDCl3): δ 6.4(d, 4H), 6.6(t, 2H), 6.75-6.8(m, 8H), 7.0-7. l(m, 6H), 7.2-7.3(m, 10H), 7.45-7.6(m, 10H), 7.7-7.8 (m, 4H) , 7.9-7.95 (m, 4H)
MS: 1012 (found), 1013.27 (calculated)
[Preparation Example 9] Preparation of Compound (9) (Chemical Formula 2 : R1 = R2 = 2-naphthyl, R3 = R4 = R5 = R6 = phenyl )
The same procedure as described in Preparation Example 1 was repeated but using 2 , 7-dichloroanthraquinone (0.5 g, 1.8 mmol) and diphenylamine (0.65 g, 3.9 mmol) to obtain bis (2,7- diphenyl) anthraquinone (0.60 g, 1.1 mmol, yield: 61%). The same procedure as described in Preparation Example 1 was repeated but using bis (2 , 7-diphenyl) anthraquinone (0.6 g, 1.1 mmol) thus prepared, to obtain Compound (9) (0.40 g, 0.52 mmol, overall yield: 29%) .
1H NMR (200MHz, CDCl3): δ 6.4(d, 8H), 6.6(t, 4H), 6.75-6.8(m, 4H), 7.0(m, 8H), 7.3(m, 4H), 7.5-7.55(m, 4H), 7.65-7.8(m, 6H), 7.9(s, 2H) MS: 764 (found), 764.98 (calculated)
[Preparation Example 10] Preparation of Compound (10) (Chemical Formula 2: Ri = R2 = R3 = R5 = 2-naphthyl, R4 = R6 = phenyl )
The same procedure as described in Preparation Example 9 was repeated but using N-phenyl-2-naphthylamine (0.85 g, 3.9 mmol) to obtain Compound (10) (0.29 g, 0.34 mmol, overall yield: 19%)
1H NMR (200MHz, CDCl3): δ 6.4(d, 4H), β.6(t, 2H), 6.75-6.8 (m, 8H), 7.0-7. l(m, 6H), 7.2-7.3(m, 6H), 7.45-7.6(m, 10H), 7.65-7.8(m, 6H) , 7.9 (s, 2H)
MS: 864 (found), 865.10 (calculated) .
[Preparation Example 11] Preparation of Compound (11) (Chemical Formula 1: Rx = R2 = 2-naphthyl, R3 = R4 = R5 = R6 = 2- anthryl)
The same procedure as described in Preparation Example 1 was repeated but using di (2-anthryl) amine (2.8 g, 7.6 mmol) to obtain Compound (11) (0.29 g, 0.25 mmol, overall yield: 7%).
1H NMR (200MHz, CDCl3): δ β.75-6.8(m, 12H), 7.25-7.3(m, 12H), 7.45-7.6(m, 16H), 7.65-7.8(m, 14H), 7.9(s, 2H) MS/FAB: 1164 (found) , 1165.46 (calculated)
[Example 1] Manufacture of OLED by using the compound according to the present invention
An OLED having the structure employing the electroluminescent material.
First, a transparent electrode ITO thin film (15 Ω/D) obtained from a glass for OLED (manufactured by Samsung-Corning) was subjected to ultrasonic washing by trichloroethylene, acetone, ethanol and distilled water, subsequently, and stored in isopronanol before use.
Then, an ITO substrate was equipped in a substrate folder of vacuum vapor deposition apparatus, and 4 , 4 ' , 4" -tris (N, N- (2- naphthyl) -phenylamino) triphenylamine (2-TNATA) represented by following structural formula 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. Electric current was applied to the cell to evaporate 2-TNATA to vapor-deposit a hole injection layer having 60 nm of thickness on the ITO substrate.
2-TNATA
Then, to another cell of the vacuum vapor deposition apparatus, charged was N, N' -bis (α-naphthyl) -N, N' -diphenyl-4 , 4 ' - diamine (NPB) , and electric current was applied to the cell to evaporate NPB to vapor-deposit a hole transport layer of 20 nm of thickness on the hole injection layer.
NPB
After forming the hole injection layer and hole transport layer, an electroluminescent layer was vapor-deposited thereon as follows. In one cell of the vacuum vapor deposition apparatus, charged was 7 , 12-di (2-naphthyl) -10-phenyl-benz (a) anthracene
(DNPBA, Compound 34) represented by following structural formula, and in another cell, a compound according to the present invention (ex. Compound 4) as a dopant, and the two substances are evaporated at a different rate to dope with 2 mol% to 5 mol%,
to vapor-deposit an electroluminescent layer (4) having 30 nm of thickness on said hole transport layer.
DNPBA Compound 4
Then, AIq represented by following structural formula was vapor-deposited as an electron transport layer having 20 nm of thickness, and lithium quinolate (Liq) represented by following structural formula was vapor-deposited as an electron injecting layer having from 1 to 2 nm of thickness. Thereafter, an Al cathode was vapor-deposited with 150 nm of thickness by using another vapor deposition apparatus to manufacture an OLED.
AIq Liq
Each compound for individual material was purified by vacuum sublimation under 10"6 torr, and employed as an electroluminescent material for OLED.
[Comparative Example 1] Preparation of an OLED employing conventional electroluminescent material
A hole injecting layer and hole transport layer were created according to the same procedure as described in Example 1, and tris (8 -hydroxyquinoline) aluminum (III) (AIq) was charged as an electroluminescent host material to another cell of said vacuum vapor deposition apparatus. Coumarin 545T (C545T) represented by following structural formula was charged to still another cell. The two substances are doped by evaporating with different rates, to vapor-deposit an electroluminescent layer having 30 nm of thickness on said hole transport layer. The doping concentration at this time was preferably from 2 to 5 mol% on the basis of the amount of AIq.
C545T
Then, an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedure as described in Example 1, and an Al cathode was vapor-deposited by using another vacuum vapor deposition apparatus with a thickness of 150 nm, to manufacture an OLED.
[Comparative Example 2] Manufacturing of an OLED by using a conventional electroluminescent material
A hole injecting layer and hole transport layer were created according to the same procedure as described in Example 1, and DNPBA was charged as an electroluminescent host material to another cell of said vacuum vapor deposition apparatus, while Compound G was charged to still another cell. The two substances
are doped with from 2 to 5 mol% concentration based on DNPBA by- evaporating with different rates, to vapor-deposit an electroluminescent layer having 30 nm of thickness on said hole transport layer.
Compound (j
Then, an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedure as described in Example 1, and an Al cathode was vapor-deposited by using another vacuum vapor deposition apparatus with a thickness of 150 nm, to manufacture an OLED.
[Example 2] Electroluminescent properties of OLED manufactured
Electroluminescent efficiency of an OLED comprising the organic electroluminescent compounds prepared from Example 1 and Comparative Example 1 according to the present invention and a conventional electroluminescent compound was measured at 5,000 cd/m2 and 20,000 cd/m2, respectively, of which the results are shown in Table 1. Since the luminescent properties in the range of high luminance are very importance in case of green electroluminescent material, in particular, the data of luminance as high as about 20,000 cd/m2 was also attached in order to reflect those properties.
[Table 1]
As can be seen from Table 1, 3.0% doping with Compound 34
(DNPBA) showed the highest electroluminescent efficiency. In particular, Compounds 4, 5 and 8 showed about twice of the efficiency as compared to that of conventional Alq:C545T
(Comparative Example 1) or of Compound G (Comparative Example 2) .
Fig. 3 is an electroluminescent efficiency curve of
Alq:C545T as a conventional electroluminescent material, and Fig.
4 is an electroluminescent efficiency curve with Compound G being
employed as the electroluminescent material. Fig. 5 and Fig. 6 shows luminance-voltage and electroluminescent efficiency- luminance curve, respectively. In particular, the fact that the high performance electroluminescent material according to the present invention have not more than 3 cd/A of lowering of efficiency even at a luminance as high as about 20,000 cd/m2, indicates that the electroluminescent material of the present invention has excellent material properties even maintained at a high luminance . The results of Table 1 shows that C545T also exhibits good luminescent color property, while Compound G exhibits luminescent color with short-wavelength shift, which means somewhat poor luminescent color property as compared to the materials according to the present invention. Fig. 6 is an EL spectrum of electroluminescent material according to the present invention, while Fig. 7 compares the luminescent color of Compound 4 according to the present invention and that of Comparative Example 1. They show good luminescent color properties without showing significant difference from conventional pure green electroluminescent material. They show typical green electroluminescent peak at 520 nm, and the material according to the invention shows no substantial deterioration of properties of color purity as the electroluminescent efficiency increases.
Among the properties of material according to the present invention, Fig. 9, that is a life curve at the luminance of 10,000 cd/m2, shows that the life property of the material of the invention is excellent as compared to that of conventional electroluminescent material. In particular, the material according to the present invention does not have property of
rapid lowering of initial luminance as was found in conventional material. Relative luminances after 800 hours of operation are 63%, 73% and 88% for C545T, Compound G and Example 1, respectively, which implies actual improvement of 2 to 5 times of life in terms of half life of luminance. This is the most valuable advantage of the material of the invention, on the contrast concept of the conventional electroluminescent material which has excellent electron conductivity.
[Example 3] Manufacturing of OLED' s employing the compound according to the present invention and Compound of Chemical Formula 3
A hole injecting layer and hole transport layer were created according to the same procedure as described in Example 1, and Compound (18) (or Compound (19) or Compound (23), or Compound (24), or Compound (25)) was charged as an electroluminescent host material to another cell of said vacuum vapor deposition apparatus. Compound (1) (or Compound (5), or Compound (13)) was charged to still another cell. The two substances are doped by evaporating with different rates, to vapor-deposit an electroluminescent layer having 30 nm of thickness on said hole transport layer. The doping concentration at this time was preferably from 2 to 5 mol% on the basis of the amount of the electroluminescent host material .
[Table 2]
From Table 2, improved properties of various electroluminescent host materials according to the present invention were confirmed.
In particular, when employing a 9 , 10-diarylanthracene derivative with an aromatic ring substituent at 2-position, as suggested according to the present invention, a large enhancement in terms of electroluminescent efficiency was confirmed, while no significant difference from conventional host material occurred in terms of CIE coordinates. Thus, the materials according to the present invention showed improvement at low luminance as well as high luminance, so that they can give advantageous properties
in both passive- and active-type organic light emitting diode. Actually, the properties as described above are advantageous in terms of electric power consumption as compared to the case employing conventional 9, 10-diarylanthracene as the electroluminescent host material, to afford the present invention of many chances to be practiced.
Industrial applicationt
The organic electroluminescent compounds according to the present invention have good electroluminescent efficiency and excellent life properties, thereby providing OLED having very long lifetime of operation.
Claims
1. An organic electroluminescent compound represented by- Chemical Formula 1 or 2 : [Chemical Formula 1]
2. An organic electroluminescent compound according to claim 1, wherein each of Ri and R2 of Chemical Formula 1 or 2 is independently selected from naphthyl, anthryl, fluoranthenyl, pyrenyl , fluorenyl, biphenyl and perilenyl group; and each of R3 to R6 is independenly selected from phenyl, naphthyl, anthryl, phenanthryl , fluorenyl, fluoranthenyl, pyrenyl, perilenyl, naphthacenyl and biphenyl group.
3.An organic electroluminescent compound according to claim 2, wherein each of Rx and R2 of Chemical Formula 1 or 2 is
independently selected from 2-naphthyl, 2-anthryl, 2- fluoranthenyl , 1-pyrenyl, 2-fluorenyl, 4-biphenyl and 3- perilenyl group.
4. An organic electroluminescent compound according to claim 3, wherein each aromatic ring of R1 to R6 has additional substituent of methyl, t-butyl or methoxy group.
5. An organic electroluminescent compound according to claim 4, which is represented by one of the following structural formulas :
)
6. An organic light emitting diode (OLED) comprising a first electrode, at least one organic layer and a second electrode in a subsequently laminated form, wherein at least one layer of said organic layers comprise (s) the organic electroluminescent compound according to any one of claims 1 to 5.
7. An organic light emitting diode (OLED) comprising an anode; a cathode; and a luminescent region interposed between said anode and said cathode, wherein said luminescent region comprises at least one organic electroluminescent compound according to any one of claims 1 to 5; and at least one compound selected from anthracene derivatives, benz [a] anthracene derivatives and naphthacene derivatives.
8. An organic light emitting diode (OLED) according to claim 7, wherein the anthracene derivative or benz [a] anthracene derivative is a compound represented by Chemical Formula 3
or 4 :
[Chemical Formula 3]
[Chemical Formula 4]
9. An organic light emitting diode (OLED) according to claim 8, wherein each of R11 to R13 of Chemical Formula 3 or 4 is independently selected from phenyl, 2-naphthyl, 2-anthryl, 2-fluoranthenyl, 1-pyrenyl, 2-fluorenyl, 4-biphenyl and 3- perilenyl group.
10. An organic light emitting diode (OLED) according to claim 9, wherein the anthracene derivative is a compound represented by one of the following formulas:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06783605A EP1922382A4 (en) | 2005-08-16 | 2006-08-14 | Green electroluminescent compounds and organic electroluminescent device using the same |
| US11/990,502 US20090128010A1 (en) | 2005-08-16 | 2006-08-14 | Green Electroluminescent Compounds and Organic Electroluminescent Device Using the Same |
| JP2008526873A JP4969575B2 (en) | 2005-08-16 | 2006-08-14 | Green light emitting compound and light emitting device employing the same as light emitting material |
| CN2006800298508A CN101243157B (en) | 2005-08-16 | 2006-08-14 | Green electroluminescent compounds and organic electroluminescent device using the same |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2005-0074983 | 2005-08-16 | ||
| KR20050074983 | 2005-08-16 | ||
| KR1020060074910A KR100788254B1 (en) | 2005-08-16 | 2006-08-08 | Green electroluminescent compounds and organic electroluminescent device using the same |
| KR10-2006-0074910 | 2006-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2007021117A1 true WO2007021117A1 (en) | 2007-02-22 |
Family
ID=37757751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2006/003188 WO2007021117A1 (en) | 2005-08-16 | 2006-08-14 | Green electroluminescent compounds and organic electroluminescent device using the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090128010A1 (en) |
| EP (1) | EP1922382A4 (en) |
| JP (2) | JP4969575B2 (en) |
| KR (1) | KR100788254B1 (en) |
| CN (1) | CN101243157B (en) |
| WO (1) | WO2007021117A1 (en) |
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| Publication number | Publication date |
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| JP2009504730A (en) | 2009-02-05 |
| CN101243157A (en) | 2008-08-13 |
| US20090128010A1 (en) | 2009-05-21 |
| EP1922382A1 (en) | 2008-05-21 |
| JP4969575B2 (en) | 2012-07-04 |
| KR100788254B1 (en) | 2007-12-27 |
| CN101243157B (en) | 2012-09-05 |
| JP2011190454A (en) | 2011-09-29 |
| EP1922382A4 (en) | 2010-08-25 |
| KR20070021043A (en) | 2007-02-22 |
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