WO2010114263A2 - 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
- Publication number
- WO2010114263A2 WO2010114263A2 PCT/KR2010/001896 KR2010001896W WO2010114263A2 WO 2010114263 A2 WO2010114263 A2 WO 2010114263A2 KR 2010001896 W KR2010001896 W KR 2010001896W WO 2010114263 A2 WO2010114263 A2 WO 2010114263A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituent
- alkyl
- fused
- organic electroluminescent
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 125000001424 substituent group Chemical group 0.000 claims description 286
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 239000010410 layer Substances 0.000 claims description 59
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 44
- -1 nitro, hydroxyl Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000005571 adamantylene group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 23
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- 238000004020 luminiscence type Methods 0.000 abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000001771 vacuum deposition Methods 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 4
- 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 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 0 C*=Cc(c(C=*)c(*)c1c2cccc1)c2Ic(c1c2cccc1)c(cccc1)c1c2[Al] Chemical compound C*=Cc(c(C=*)c(*)c1c2cccc1)c2Ic(c1c2cccc1)c(cccc1)c1c2[Al] 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000002541 furyl group Chemical group 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 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 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 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 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- XHZUPQUVMGRPDC-UHFFFAOYSA-N 1,2,3,4-tetratert-butylperylene Chemical group C1=CC(C2=C(C(C(C)(C)C)=C(C=3C2=C2C=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)=C3C2=CC=CC3=C1 XHZUPQUVMGRPDC-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-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
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BQMNNWIYAUNZBO-UHFFFAOYSA-N 2-chloro-4a,9a-dihydroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3C=C(Cl)C=CC3C(=O)C2=C1 BQMNNWIYAUNZBO-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- YCPBCVTUBBBNJJ-UHFFFAOYSA-N 5,11-dihydridoindolo[3,2-b]carbazole Natural products N1C2=CC=CC=C2C2=C1C=C1C3=CC=CC=C3NC1=C2 YCPBCVTUBBBNJJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 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
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 229910003953 H3PO2 Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 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
- 150000004945 aromatic hydrocarbons Chemical class 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 150000001768 cations Chemical class 0.000 description 1
- 125000005584 chrysenylene group Chemical group 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
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004977 cycloheptylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000004978 cyclooctylene group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000005105 dialkylarylsilyl 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
- 239000012776 electronic material Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 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
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- HLVSZSQYBQCBQG-UHFFFAOYSA-N indolo[3,2-b]carbazole Chemical compound C12=CC=CC=C2N=C2C1=CC1=NC3=CC=CC=C3C1=C2 HLVSZSQYBQCBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002061 vacuum sublimation 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
- 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
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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 organic electroluminescent devices including the same.
- the organic electroluminescent compounds according to the invention are represented by Chemical Formula 1:
- the electroluminescent materials may be divided into host materials and dopant materials.
- an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
- development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
- development of materials which are much superior to existing electroluminescent materials is urgently needed.
- blue electroluminescence becomes advantageous in terms of luminescence efficiency if the electroluminescence wavelength is shifted a little toward a longer wavelength. But, then, it is not applicable to high-quality displays because pure blue color is not attained. Therefore, researches and developments to improve color purity, efficiency and thermal stability are highly 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 superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
- Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound.
- Solution to Problem [12] The present inventionprovides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. With superior luminescence efficiency, color purity and life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
- L represents (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without sub- stituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene, (C6-C30)ar(Cl-C30)alkylene with or without substituent(s), (Cl-C30)alkylenethi
- Ri through R 4 , A ⁇ i and Ar 2 independently represent hydrogen, deuterium, halogen,
- R 2 i through R 23 and R 31 through R 46 independently represent hydrogen, deuterium, halogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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 sub- stituent(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 sub- stituent(s), adamantyl with or without substituting
- [20] a represents an integer 1 or 2;
- alkyl include both linear and branched species.
- 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, 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.
- 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, benzothiophenyl, isoben- zofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, ben- zoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quino
- the alkyl moiety of " (C 1 -C30)alkyl, tri(C 1 -C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (Cl-C30)alkyloxy, (C 1 -C30)alkylthio, (C 1 -C30)alkyloxycarbonyl, (C 1 -C30)alkylcarbonyl, (Cl-C30)alkyloxycarbonyloxy or (Cl-C30)alkylcarbonyloxy" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
- the aryl alkyl moiety of "(C6-C30)aryl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy" may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
- the "(C3-C30)heteroaryl” may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
- the "(C3-C30)cycloalkyl” may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
- the "(C2-C30)alkenyl or alkynyl” may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
- the phrase "with or without substituent(s)" means that the substituents of L, R 1 through R 4 , R 11 through R 18 , R 21 through R 23 , R 31 through R 46 , Ar 1 and Ar 2 may be independently substituted with one or more substituent(s) selected from a group consisting of deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituents), 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), tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl
- L may be selected from arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluoranthenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene, perylenylene, indenofluorene, etc., heteroarylene such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, quinolinylene, quinoxalinylene, phenanthrolinylene, indolo[3,2-b]carbazole, etc., cycloalkylene such as cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, etc., -O- or -S-, but is not limited thereto. It may be further substituted as in Chemical Formula 1.
- arylene such as phenylene
- Ri through R 4 may be independently selected from hydrogen, deuterium, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., cyano, tri- alkylsilyl such as trimethylsilyl, triethylsilyl, dimethylethylsilyl, tributylsilyl, etc., di- alkylarylsilyl such as dimethylphenylsilyl, etc. or triarylsilyl such as triphenyls, al
- a ⁇ i and Ar 2 may be independently selected from aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl(s) such as 1,2-dihydroacenaphthyl, etc., heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused with one or more aromatic ring(s) such as benzopyrrolidino,
- heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc.,
- R 31 through R 38 independently represent (Cl-C30)alkyl with or without sub- stituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring.
- organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
- the present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode.
- the organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
- the organic layer may include an electroluminescent layer which further includes one or more dopant(s) or host(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
- the dopant or host used in the organic electronic device of the present invention is not particularly limited.
- the dopant used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 2 to 4:
- Ar 11 and Ar 12 independently represent (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without sub- stituent(s), (C6-C30)arylamino with or without substituent(s), (Cl-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered hete- rocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), and Ar 11 and Ar 12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without
- Ar 13 is (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected form the following structures:
- Ar 13 is (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected form the following structures:
- Ar 14 and Ar 15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
- R 201 through R 203 independently represent hydrogen, deuterium, (Cl-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
- the dopant compound represented by Chemical Formulas 2 to 4 may be exemplified by the following compounds, but is not limited thereto:
- the host used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 5 and 6: [143] [Chemical Formula 5] [144] (Ar 21 ) f -L 21 -(Ar 22 ) g [145] [Chemical Formula 6] [146] (Ar 23 VL 22 -(Ar 24 X [147] wherein [148] L 21 represents (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
- L 22 represents anthracenylene with or without substituent(s);
- Ar 21 through Ar 24 independently selected from hydrogen, (Cl-C30)alkyl with or without substituent(s), (Cl-C30)alkoxy with or without substituent(s), halogen, (C4-C30)heteroaryl with or without substituent(s), (C5-C30)cycloalkyl with or without substituent(s) and (C6-C30)aryl with or without substituent(s); and
- f, g, h and i are independently an integer from 0 to 4.
- the host compound represented by Chemical Formulas 5 and 6 may be exemplified by the following compounds, but is not limited thereto:
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 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) or complex(es) selected from 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 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, red and green light at the same time, to provide a white light-emitting organic electroluminescent device.
- the compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
- a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a 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. A driving 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.
- a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes.
- injection and transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion.
- injection and transport of holes from the mixed region to the electroluminescent medium becomes easier, because the hole transport compound is oxidized to a cation.
- Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds.
- Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
- a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
- the organic electroluminescent compound according to the present invention exhibits good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very good operation life.
- Example 1 Manufacture of OLED device using the organic electroluminescent compound according to the present invention
- An OLED device was manufactured using the organic electroluminescent compound of the present invention.
- a transparent electrode ITO film (15 ⁇ /D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
- the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
- a vacuum deposition apparatus After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10 6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
- NPB ⁇ f,./V-bis( ⁇ -naphthyl)-/V,./V '- diphenyl-4,4'-diamine
- An electroluminescent layer was formed on the hole transport layer as follows.
- Compound 1 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound E was added in another cell as a dopant.
- the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- Each electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10 6 torr.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding dinaphthylanthracene (DNA) in a cell of a vacuum deposition apparatus as a host and adding Compound 136 according to the present invention in another cell as a dopant, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- DNA dinaphthylanthracene
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in a cell of a vacuum deposition apparatus as an electroluminescent host material and adding Compound E in another cell, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- the organic electroluminescent compounds according to the present invention exhibit lower driving voltage and improved luminescence efficiency while maintaining comparable or better color purity as compared to Comparative Example 1.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding Compound 168 according to the present invention in a cell of a vacuum deposition apparatus as a host and adding Compound A in another cell as a dopant, the two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on Compound A.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after DNA in a cell of a vacuum deposition apparatus as a host and adding Compound 129 according to the present invention in another cell as a dopant, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
- a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in a cell of a vacuum deposition apparatus as an electroluminescent host material and adding blue-emitting Compound A in another cell, an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at deposition rate of 100:1.
- the organic electroluminescent compounds according to the present invention exhibit comparable or better luminescence efficiency as compared to Comparative Example 1. And, when used as a dopant, they exhibit significantly improved color purity (blue rather than light blue) while maintaining comparable or better luminescence efficiency as compared to Comparative Example 1.
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Abstract
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same. With good luminescence efficiency and excellent color purity and life property of the material, the organic electroluminescent compounds according to the present invention may be used to manufacture OLEDs having very good operation life.
Description
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same. Specifically, the organic electroluminescent compounds according to the invention are represented by Chemical Formula 1:
[Chemical Formula 1]
wherein
all of R1 through R4 are not hydrogen at the same time; and Ar1 and Ar2 are not identical with each other.
In order to realize a full-color OLED display, three electroluminescent materials of red, green and blue (RGB) are employed. Thus, development of RGB electroluminescent materials having high efficiency and long operation life is important in enhancing the properties of an organic EL device. In functional aspect, the electroluminescent materials may be divided into host materials and dopant materials. In general, an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task. Especially, considering the level of EL performance required for medium-to-large sized OLED panels, development of materials which are much superior to existing electroluminescent materials is urgently needed.
For green fluorescent materials, tris(8-hydroxyquinoline)-aluminum(III) (Alq) is used as a host and a coumarin derivative (Compound a, C545T), a quinacridone derivative(Compound b), DPT (Compound c), or the like are used as a dopant, with a doping concentration of several to tens %. Although the existing electroluminescent materials exhibit an initial luminescence efficiency that allows commercialization, the efficiency degrades quickly with time. Due to the lifetime problem, they are difficult to be employed in high-performance, large-sized panels.
For blue electroluminescent materials, a lot of materials have been commercialized following Idemitsu Kosan s DPVBi (Compound d). In addition to the Idemitsu Kosan's blue material system, Kodak's dinaphthylanthracene (Compound e) and tetra(t-butyl)perylene (Compound f) are known, but more researches and developments are necessary. Until now, Idemitsu Kosan's distyryl compound system is known to have the best efficiency. It exhibits a power efficiency of 6 lm/W and an operation life of 30,000 hours or longer. However, its sky-blue color is not appropriate for a full-color display is only thousands of hours. In general, blue electroluminescence becomes advantageous in terms of luminescence efficiency if the electroluminescence wavelength is shifted a little toward a longer wavelength. But, then, it is not applicable to high-quality displays because pure blue color is not attained. Therefore, researches and developments to improve color purity, efficiency and thermal stability are highly 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 superior backbone with appropriate color coordinates in order to solve the aforesaid problems. Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound.
The present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. With superior luminescence efficiency, color purity and life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
[Chemical Formula 1]
wherein
L represents (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene, (C6-C30)ar(C1-C30)alkylene with or without substituent(s), (C1-C30)alkylenethio with or without substituent(s), (C1-C30)alkyleneoxy with or without substituent(s), (C6-C30)aryleneoxy with or without substituent(s), (C6-C30)arylenethio with or without substituent(s), -O- or -S-;
R1 through R4, Ar1 and Ar2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 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).], 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro, hydroxyl, 
or 
, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
W represents -C(R31R32)m-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)-, -B(R38)-, -In(R39)-, -Se-, -Ge(R40)(R41)-, -Sn(R42)(R43)-, -Ga(R44)- or -(R45)C=C(R46)-;
R21 through R23 and R31 through R46 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
a represents an integer 1 or 2; and
the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P,
with the proviso that all of R1 through R4 are not hydrogen and that Ar1 and Ar2 are not identical with each other.
In the present invention, "alkyl", "alkoxy" and other substituents containing alkyl moiety include both linear and branched species.
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, 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 includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples 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, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but are not limited thereto.
In the present invention, the alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C1-C30)alkyloxycarbonyl, (C1-C30)alkylcarbonyl, (C1-C30)alkyloxycarbonyloxy or (C1-C30)alkylcarbonyloxy" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl alkyl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy" may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The "(C3-C30)heteroaryl" may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The "(C3-C30)cycloalkyl" may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The "(C2-C30)alkenyl or alkynyl" may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
And, in the present invention, the phrase "with or without substituent(s)" means that the substituents of L, R1 through R4, R11 through R18, R21 through R23, R31 through R46, Ar1 and Ar2 may be independently substituted with one or more substituent(s) selected from a 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), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38 [wherein R31 through R38 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, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring.
L may be selected from arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluoranthenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene, perylenylene, indenofluorene, etc., heteroarylene such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, quinolinylene, quinoxalinylene, phenanthrolinylene, indolo[3,2-b]carbazole, etc., cycloalkylene such as cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, etc., -O- or -S-, but is not limited thereto. It may be further substituted as in Chemical Formula 1.
R1 through R4 may be independently selected from hydrogen, deuterium, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., cyano, trialkylsilyl such as trimethylsilyl, triethylsilyl, dimethylethylsilyl, tributylsilyl, etc., dialkylarylsilyl such as dimethylphenylsilyl, etc. or triarylsilyl such as triphenylsilyl, trinaphthylsilyl, etc., but are not limited thereto. They may be further substituted as in Chemical Formula 1.
Ar1 and Ar2 may be independently selected from aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl(s) such as 1,2-dihydroacenaphthyl, etc., heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused with one or more aromatic ring(s) such as benzopyrrolidino, benzopiperidino, dibenzomorpholino, dibenzoazepino, etc., amino substituted with aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc. or heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., 
or 
, but are not limited thereto. They may be further substituted as in Chemical Formula 1.
Specifically, 
and 
may be exemplified by the following structures:
wherein
R31 through R38 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 each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring.
More specifically, the organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
The organic electroluminescent compound according to the present invention may be prepared by Scheme 1:
[Scheme 1]
wherein L, Ar1, Ar2, R1, R2, R3 and R4 are the same as defined in Chemical Formula 1.
The present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode. The organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
Further, the organic layer may include an electroluminescent layer which further includes one or more dopant(s) or host(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1. The dopant or host used in the organic electronic device of the present invention is not particularly limited.
Preferably, the dopant used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 2 to 4:
[Chemical Formula 2]
[Chemical Formula 3]
wherein
Ar11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 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) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), and Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
in case c is 1, Ar13 is (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected form the following structures:
in case c is 2, Ar13 is (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected form the following structures:
Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s); and
d is an integer from 1 to 4, and e is an integer 0 or 1; and
[Chemical Formula 4]
wherein
R211 through R214 independently represent hydrogen, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), 5- or 6-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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 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).], 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring.
The dopant compound represented by Chemical Formulas 2 to 4 may be exemplified by the following compounds, but is not limited thereto:
Preferably, the host used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 5 and 6:
[Chemical Formula 5]
(Ar21)f-L21-(Ar22)g
[Chemical Formula 6]
(Ar23)h-L22-(Ar24)i
wherein
L21 represents (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
L22 represents anthracenylene with or without substituent(s);
Ar21 through Ar24 independently selected from hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), halogen, (C4-C30)heteroaryl with or without substituent(s), (C5-C30)cycloalkyl with or without substituent(s) and (C6-C30)aryl with or without substituent(s); and
f, g, h and i are independently an integer from 0 to 4.
The host compound represented by Chemical Formulas 5 and 6 may be exemplified by the following compounds, but is not limited thereto:
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are 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 metal(s) or complex(es) selected from 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 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, red and green light at the same time, to provide a white light-emitting organic electroluminescent device. The compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 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. A driving 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.
Further, in the electroluminescent device according to the present invention, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. In that case, injection and transport of electrons from the mixed region to the electroluminescent medium becomes easier, because the electron transport compound is reduced to an anion. Further, injection and transport of holes from the mixed region to the electroluminescent medium becomes easier, because the hole transport compound is oxidized to a cation. Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds. Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
Further, a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
Since the organic electroluminescent compound according to the present invention exhibits good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very good operation life.
Hereinafter, the compound for organic electronic material, the preparation method thereof and the electroluminescent property of the device according to the present invention will be described for some compounds. However, the following embodiments are only exemplary and do not limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 164
Preparation of Compound
a
9-Bromoanthracene (15.0 g, 58.3 mmol), phenylboronic acid (8.5 g, 70.0 mmol) and Pd(PPh3)4 (6.7 g, 5.8 mmol) were dissolved in a mixture of toluene/ethanol (300 mL/150 mL). After adding 2 M K2CO3 aqueous solution (486 mL), the mixture was stirred at 120 ℃ for 5 hours under reflux. Then, after cooling to room temperature, distilled water was added to terminate the reaction. After extraction with EA, the resulting organic layer was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Recrystallization with THF/methanol yielded Compound a (12.0 g, 81%).
Preparation of Compound
b
Compound a (11.7 g, 46.0 mmol) and N-bromosuccinimide (9.0 g, 50.6 mmol) were dissolved in MC (360 mL) in the presence of nitrogen and then stirred at room temperature for 5 hours. Then, after terminating the reaction by adding distilled water followed by extraction with MC, the resulting organic layer was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Recrystallization with THF/methanol yielded Compound b (13.0 g, 85.0%).
Preparation of Compound
c
Compound b (13.0 g, 39.0 mmol) was dissolved in THF (150 mL) and n-BuLi (23.4 mL, 58.5 mmol, 2.5 M in hexane) was slowly added thereto at -78 ℃. One hour later, trimethyl borate (5.7 mL) was added. After stirring at room temperature for 12 hours, distilled water was added and the product was extracted with EA. After drying with anhydrous MgSO4 followed by distillation under reduced pressure, column separation yielded Compound c (7.6 g, 25.5 mmol, 67.2%).
Preparation of Compound
d
Compound c (7.6 g, 25.5 mmol), 1,4-dibromobenzene (6.0 g, 25.5 mmol) and Pd(PPh3)4 (3.0 g, 2.6 mmol) were dissolved in a mixture of toluene/ethanol (200 mL/100 mL). After adding 2 M Na2CO3 aqueous solution (200 mL), the mixture was stirred at 120 ℃ for 5 hours under reflux. Then, after cooling to room temperature, distilled water was added to terminate the reaction. After extraction with EA, the resulting organic layer was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Recrystallization with THF/methanol yielded Compound d (7.4 g, 18.1 mmol, 71%).
Preparation of Compound
1-1
2-Chloroanthracene-9,10(4aH,9aH)-dione (50.0 g, 0.2 mol), phenylboronic acid (37.6 g, 0.3 mol) and Pd(PPh3)4 (9.5 g, 8.2 mmol) were added to a two-neck flask. After stirring while adding toluene, 2 M K2CO3 aqueous solution (500 mL, 1.0 mol) and ethanol (500 mL) were added. The mixture was stirred at 120 ℃ for 5 hours under reflux. Upon completion of the reaction, after cooling to room temperature, distilled water was added. After extraction with EA, the resulting organic layer was dried with anhydrous MgSO4 and the solvent was removed using a rotary evaporator. Separation by column chromatography using hexane and EA as developing solvents yielded Compound 1-1 (56.0 g, 95.0%).
Preparation of Compound
1-2
Compound 1-1 (13.0 g, 45.7 mmol) was added to acetic acid (200 mL). After adding HI (120 mL, 914.5 mmol, 57% aqueous solution) and H3PO2 (80 mL, 777.3 mmol, 50% aqueous solution), the mixture was stirred under reflux. 12 hours later, after cooling to room temperature, distilled water was added and thus produced solid was filtered under reduced pressure. After washing with NaOH aqueous solution and then with distilled water and methanol, recrystallization with EA yielded Compound 1-2 (10.0 g, 39.3 mmol, 86.0%).
Preparation of Compound
1-3
Compound 1-2 (10.0 g, 39.3 mmol) was dissolved in THF (500 mL) and N-bromosuccinimide (7.8 g, 43.3 mmol) was added thereto. After stirring for 24 hours at room temperature followed by distillation under reduced pressure, thus produced solid was washed with methanol. Compound 1-3 (11.4 g, 34.2 mmol, 87.0%) was yielded.
Preparation of Compound
1-4
Compound 1-3 (11.4 g, 34.2 mmol), 9,9-dimethyl-9H-fluoren-2-ylboronic acid (12.2 g, 51.3 mmol), Pd(PPh3)4 (1.9 g, 1.7 mmol), 2 M K2CO3 (50 mL), toluene (100 mL) and ethanol (50 mL) were stirred for 5 hours under reflux. After cooling to room temperature, distilled water was added and the product was extracted with EA. After drying with anhydrous MgSO4 followed by distillation under reduced pressure, thus produced solid was dissolved in MC and filtered using silica gel. After distillation under reduced pressure, recrystallization with methanol yielded Compound 1-4 (14.0 g, 31.3 mmol, 91.6%).
Preparation of Compound
1-5
Compound 1-4 (14.0 g, 31.3 mmol) was dissolved in MC (500 mL) and N-bromosuccinimide (12.8 g, 72.1 mmol) was added thereto. After stirring for 3 hours under reflux, followed by cooling to room temperature and distillation under reduced pressure, thus produced solid was washed with methanol. Compound 1-5 (11.4 g, 21.7 mmol, 69.2%) was yielded.
Preparation of Compound
1-6
Compound 1-5 (11.4 g, 21.7 mmol) was dissolved in THF (150 mL) and n-BuLi (11.3 mL, 28.2 mmol, 2.5 M in hexane) was slowly added thereto at -78 ℃. One hour later, trimethyl borate (4.8 mL) was added. After stirring at room temperature for 12 hours, distilled water was added and the product was extracted with EA. After drying with anhydrous MgSO4 followed by distillation under reduced pressure, column separation yielded Compound 1-6 (7.1 g, 14.7 mmol, 67.5%).
Preparation of Compound
164
Compound 1-6 (7.1 g, 14.7 mmol), Compound d (5.0 g, 12.3 mmol), Pd(PPh3)4 (1.4 g, 1.7 mmol), 2 M K2CO3 (35 mL), toluene (100 mL) and ethanol (40 mL) were stirred for 5 hours under reflux. After cooling to room temperature followed by addition of methanol, thus produced solid was filtered under reduced pressure. The resulting solid was dissolved in CHCl3 and filtered using silica gel. Distillation under reduced pressure followed by recrystallization with EA yielded Compound 164 (7.0 g, 9.0 mmol, 73.7%).
Organic electroluminescent compounds, Compounds 1 to 200, were prepared in the same manner as Preparation Example 1. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
[Table 1]
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the organic electroluminescent compound of the present invention.
First, a transparent electrode ITO film (15 Ω/□) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
Then, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10-6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate. Subsequently, after adding N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current to the cell to form a hole transport layer having a thickness of 20 nm on the hole injection layer.
An electroluminescent layer was formed on the hole transport layer as follows. Compound 1 according to the present invention was added in a cell of a vacuum deposition apparatus as a host, and Compound E was added in another cell as a dopant. The two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Thereafter, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was deposited with a thickness of 20 nm as an electron transport layer. Then, after depositing lithium quinolate (Liq) 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 deposition apparatus to manufacture an OLED.
Each electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10-6 torr.
[Example 2] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding dinaphthylanthracene (DNA) in a cell of a vacuum deposition apparatus as a host and adding Compound 136 according to the present invention in another cell as a dopant, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, after depositing an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
[Comparative Example 1] Manufacture of OLED device using existing electroluminescent material
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in a cell of a vacuum deposition apparatus as an electroluminescent host material and adding Compound E in another cell, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, after depositing an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Luminescence efficiency of the OLED devices manufactured in Examples 1 and 2 and Comparative Example 1 was measured at 5,000 cd/m2. The result is given in Table 2.
[Table 2]
As seen from Table 2, when used as host or dopant for green-emitting electroluminescent devices, the organic electroluminescent compounds according to the present invention exhibit lower driving voltage and improved luminescence efficiency while maintaining comparable or better color purity as compared to Comparative Example 1.
[Example 3] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding Compound 168 according to the present invention in a cell of a vacuum deposition apparatus as a host and adding Compound A in another cell as a dopant, the two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on Compound A.
Subsequently, after depositing an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
[Example 4] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after DNA in a cell of a vacuum deposition apparatus as a host and adding Compound 129 according to the present invention in another cell as a dopant, the two materials were evaporated at different rate such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Subsequently, after depositing an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
[Comparative Example 2] Electroluminescence property of OLED device using existing electroluminescent material
A hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in a cell of a vacuum deposition apparatus as an electroluminescent host material and adding blue-emitting Compound A in another cell, an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at deposition rate of 100:1.
Subsequently, after depositing an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Luminescence efficiency of the OLED devices manufactured in Examples 3 and 4 and Comparative Example 2 was measured at 1,000 cd/m2. The result is given in Table 3.
[Table 3]
As seen from Table 3, when used as a host for blue-emitting electroluminescent devices, the organic electroluminescent compounds according to the present invention exhibit comparable or better luminescence efficiency as compared to Comparative Example 1. And, when used as a dopant, they exhibit significantly improved color purity (blue rather than light blue) while maintaining comparable or better luminescence efficiency as compared to Comparative Example 1.
Claims (9)
- An organic electroluminescent compound represented by Chemical Formula 1:[Chemical Formula 1]
whereinL represents (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene, (C6-C30)ar(C1-C30)alkylene with or without substituent(s), (C1-C30)alkylenethio with or without substituent(s), (C1-C30)alkyleneoxy with or without substituent(s), (C6-C30)aryleneoxy with or without substituent(s), (C6-C30)arylenethio with or without substituent(s), -O- or -S-;R1 through R4, Ar1 and Ar2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 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).], 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro, hydroxyl,or
, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;
W represents -C(R31R32)m-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)-, -B(R38)-, -In(R39)-, -Se-, -Ge(R40)(R41)-, -Sn(R42)(R43)-, -Ga(R44)- or -(R45)C=C(R46)-;R21 through R23 and R31 through R46 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) 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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;a represents an integer 1 or 2; andthe heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P,with the proviso that all of R1 through R4 are not hydrogen and that Ar1 and Ar2 are not identical with each other. - The organic electroluminescent compound according to claim 1, wherein the substituent of L, R1 through R4, R11 through R18, R21 through R23, R31 through R46, Ar1 and Ar2 is further substituted by one or more substituent(s) selected from a 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), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38 [wherein R31 through R38 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, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring.
- An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 or 2.
- The organic electroluminescent device according to claim 3, which comprises a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more of the organic electroluminescent compound(s) according to any of claims 1 or 2, and one or more dopant(s) selected from the compounds represented by Chemical Formulas 2 through 4:[Chemical Formula 2]
[Chemical Formula 3]
whereinAr11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 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) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), and Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring;in case c is 1, Ar13 is (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected form the following structures:
in case c is 2, Ar13 is (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected form the following structures:
Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s); andd is an integer from 1 to 4, and e is an integer 0 or 1; and[Chemical Formula 4]
whereinR211 through R214 independently represent hydrogen, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), 5- or 6-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), adamantyl with or without substituent(s),(C7-C30)bicycloalkyl with or without substituent(s), cyano, NR11R12, BR13R14, PR15R16, P(=O)R17R18 [wherein R11 through R18 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).], 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), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring. - The organic electroluminescent device according to claim 3, which comprises a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more of the organic electroluminescent compound(s) according to any of claims 1 or 2 and one or more host(s) selected from the compounds represented by Chemical Formula 5 or 6:[Chemical Formula 5](Ar21)f-L21-(Ar22)g[Chemical Formula 6](Ar23)h-L22-(Ar24)iwhereinL21 represents (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);L22 represents anthracenylene with or without substituent(s);Ar21 through Ar24 independently selected from hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), halogen, (C4-C30)heteroaryl with or without substituent(s), (C5-C30)cycloalkyl with or without substituent(s) and (C6-C30)aryl with or without substituent(s); andf, g, h and i are independently an integer from 0 to 4.
- The organic electroluminescent device according to claim 4 or 5, wherein the organic layer comprises one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds.
- The organic electroluminescent device according to claim 4 or 5, wherein the organic layer further comprises one or more metal(s) selected from a group consisting 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 4 or 5, which is a white light-emitting organic electroluminescent device wherein the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time.
- The organic electroluminescent device according to claim 4 or 5, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
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| KR10-2009-0027242 | 2009-03-31 | ||
| KR1020090027242A KR20100108914A (en) | 2009-03-31 | 2009-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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| WO2010114263A3 (en) | 2011-01-06 |
| KR20100108914A (en) | 2010-10-08 |
| TW201105773A (en) | 2011-02-16 |
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