WO2010114256A2 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- WO2010114256A2 WO2010114256A2 PCT/KR2010/001865 KR2010001865W WO2010114256A2 WO 2010114256 A2 WO2010114256 A2 WO 2010114256A2 KR 2010001865 W KR2010001865 W KR 2010001865W WO 2010114256 A2 WO2010114256 A2 WO 2010114256A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituent
- organic electroluminescent
- alkyl
- aryl
- fused
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 125000001424 substituent group Chemical group 0.000 claims description 113
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 239000010410 layer Substances 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 30
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 29
- -1 cyano, carbazolyl Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 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
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 150000002739 metals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000000463 material Substances 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000005401 electroluminescence Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 0 CCCCCc(cc1)cc2c1-c1ccc(CCCCC)cc1C21c(cc(cc2)-c3c(cccc4)c4c(-c4ccc5-c6ccccc6C6(c7cc(C(*)CCC)ccc7-c7c6cc(CCCCC)cc7)c5c4)c4c3cccc4)c2-c2ccccc12 Chemical compound CCCCCc(cc1)cc2c1-c1ccc(CCCCC)cc1C21c(cc(cc2)-c3c(cccc4)c4c(-c4ccc5-c6ccccc6C6(c7cc(C(*)CCC)ccc7-c7c6cc(CCCCC)cc7)c5c4)c4c3cccc4)c2-c2ccccc12 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 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 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 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 2
- 239000012265 solid product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-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
- LCAKAXJAQMMVTQ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-2-phenylbenzene Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LCAKAXJAQMMVTQ-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
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-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
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 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
- 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
- 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 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid 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
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl 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
- KDOQMLIRFUVJNT-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1N(c(cc1)ccc1N(c1ccccc1)c1cc2ccccc2cc1)c(cc1)ccc1N(c1ccccc1)c1cc(cccc2)c2cc1)c1cc2ccccc2cc1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1N(c(cc1)ccc1N(c1ccccc1)c1cc2ccccc2cc1)c(cc1)ccc1N(c1ccccc1)c1cc(cccc2)c2cc1)c1cc2ccccc2cc1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 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
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 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
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
-
- 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
- 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
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
-
- 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
-
- 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
- H10K85/30—Coordination compounds
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
Definitions
- the present invention relates to novel organic electroluminescent compounds, specifically, those represented by Chemical Formula (1), and organic electroluminescent devices comprising the same.
- electroluminescence (EL) devices being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate.
- Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
- An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light.
- a device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused for full colored display devices for next generation.
- An organic EL device is composed of anode/HIL/HTL/EML/ETL/EIL/cathode. The color of the light emitted (blue, green, red) from the organic electroluminescent device can be realized depending on how the electroluminescent layer (EML) is formed.
- EML electroluminescent layer
- the EL materials are classified into host materials and dopant materials from the aspect of their functions. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel.
- the color is unsuitable (sky-blue), when it is applied to a full-colored display.
- blue electroluminescentce it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength.
- it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue.
- the research and development of such materials are urgently demanded because of the problems in color purity, efficiency and thermal stability.
- the object of the invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinate, as compared to conventional host materials.
- Another object of the invention is to provide an organic electroluminescent device of high efficiency and long life by employing the organic electroluminescent compound as electroluminescent material.
- the present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and organic electroluminescent devices comprising the same.
- the organic electroluminescent compounds according to the invention exhibit high luminous efficiency, and excellent color purity and life property of the material, so that OLED' s with very excellent operation life can be manufactured therefrom.
- Ai through A 5 independently represent CR 3I or N;
- Ri through R n and R 3! independently representhydrogen, deuterium, halogen,
- R 5 i through R 58 are defined as for Ri through R 17 ;
- ring A is a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic het- eroaromatic ring, 5- or 6-membered heteroaromatic ring fused with an aromatic ring, or a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring;
- m represents an integer 1 or 2.
- Aryl group includes monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through chemical bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto.
- the naphthyl may be 1 -naphthyl or 2-naphthyl
- the anthryl may be 1 -anthryl, 2-anthryl or 9-anthryl
- the fluorenyl may be any one of 1 -fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
- the structures having one or more heteroaryl group(s) bonded through a single bond are also included.
- the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
- Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, ben- siothiazolyl, benzisox
- the alkyl groups in ' (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, (Cl-C30)alkylcarbonyloxy' described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10.
- the aryl groups in '(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 restricted carbon number from 6 to 20, or from 6 to 12.
- the heteroaryl groups in '(C3-C30)heteroaryl' may have restricted carbon number from 4 to 20, or from 4 to 12.
- the cycloalkyl groups in '(C3-C30)cycloalkyl' may have restricted carbon number from 3 to 20, or from 3 to 7.
- the alkenyl or alkynyl of '(C2-C30)alkenyl or alkynyl' may have restricted carbon number from 2 to 20, or from 2 to 10.
- R 51 through R 55 independently represent substituted or unsubstituted (Cl-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.
- organic electroluminescent compounds according to the present invention can be more specifically exemplified by the following compounds, but they are not restricted thereto.
- the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) in- terposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1).
- the organic electroluminescent compound is employed as host material of the electroluminescent layer.
- the organic electroluminescent device according to the present invention is characterized in that the organic layer comprises an electroluminescent layer containing one or more organic electroluminescent compound(s) represented by Chemical Formula (1), as well as one or more dopant(s).
- the dopant to be applied to an organic electroluminescent device according to the invention is not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (2):
- Ar 41 and Ar 42 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), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar 41 and Ar 42 may be linked each other via (C3-C30)alkylene or (C3-C30)alkenylene
- Ar 43 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures;
- Ar 43 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s)or a substituent selected from the following structures;
- each one of Ar 51 independently represents (C6-C30)arylene with or without sub- stituent(s) or (C4-C30)heteroarylene with or without substituent(s);
- R 9O i independently represents hydrogen, deuterium, (Cl-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
- the dopant compounds represented by Chemical Formula (2) can be exemplified by those described in Korean Patent Application No. 10-2009-0023442. More preferably they are selected from the following structures, but not restricted thereto.
- the organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1).
- the arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d- transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the electroluminescent compound represented by Chemical Formula (1).
- the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
- the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1), to form an organic electroluminescent device emitting white light.
- the compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- an organic electroluminescent device it is preferable to arrange one or more layer(s) (here-in-below, referred to as the 'surface layer') selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to arrange a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the EL medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer. As the result, stability in operation can be obtained.
- the 'surface layer' selected from chalcogenide layers, metal halide layers and metal oxide layers
- Examples of chalcogenides preferably include SiO x (1 ⁇ X ⁇ 2), AlO x (1 ⁇ X ⁇ 1.5),
- metal halides preferably include LiF, MgF 2 , CaF 2 , fluorides of rare earth metal or the like.
- metal oxides preferably include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.
- an organic electroluminescent device it is also preferable to arrange, on at least one surface of the pair of electrodes thus manufactured, a mixed region of electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
- the organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life property of the material, so that OLED' s having very good operation life can be manufactured therefrom. Best Mode for Carrying out the Invention
- Example 1 Manufacture of OLED 's by using organic electroluminescent compounds according to the present invention
- OLED devices were manufactured by using the electroluminescent material according to the invention.
- a transparent electrode ITO thin film (15 ⁇ /D) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in iso- propanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4 " -tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 1O 6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
- NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
- an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (84) according to the present invention as host, and Compound (E) was charged to another cell as dopant. Two substances were evaporated at different rates to provide vapor-deposition at a concentration of 2 to 5% by weight on the basis of the host. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
- Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10 ⁇ 6 torr.
- an electron transport layer (6) and an electron injecting layer (7) were vapor- deposited according to the same procedures as in Example 1, and Al cathode (8) was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
- the organic electroluminescent compounds according to the present invention are able to realize a device having higher luminous efficiency with lower operation voltage while maintaining comparable or higher color purity, as compared to that of Comparative Example 1.
- an electroluminescent layer was vapor- deposited thereon.
- Compound (1) according to the present invention as electroluminescent material
- Compound (A) (of which the structure is shown below) was charged to another cell.
- Two cells were heated at the same time to provide vapor-deposition with a deposition rate of Compound (A) at 2 to 5% by weight.
- an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
- an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor- deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
Abstract
Disclosed are novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. With good luminous efficiency and excellent life property, the disclosed organic electroluminescent compounds can be used to manufacture OLED devices having very good operation life.
Description
The present invention relates to novel organic electroluminescent compounds, specifically, those represented by Chemical Formula (1), and organic electroluminescent devices comprising the same.
[Chemical Formula 1]
Among display devices, electroluminescence (EL) devices, being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate. Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light. A device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused for full colored display devices for next generation.
The most important factor to determine luminous efficiency, lifetime or the like in an organic EL device is electroluminescent material. Several properties required for such electroluminescent materials include that the material should have high luminescent quantum yield in solid state and high mobility of electrons and holes, is not easily decomposed during vapor-deposition in vacuum, and forms uniform and stable thin film.
An organic EL device is composed of anode/HIL/HTL/EML/ETL/EIL/cathode. The color of the light emitted (blue, green, red) from the organic electroluminescent device can be realized depending on how the electroluminescent layer (EML) is formed.
The EL materials are classified into host materials and dopant materials from the aspect of their functions. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel.
In the meanwhile, as to conventional blue materials, a number of materials have been developed and commercialized since the development of diphenylvinyl-biphenyl (DPVBi) (Compound a) by Idemitsu-Kosan. In addition to the blue material system from Idemitsu-Kosan, dinaphthylanthracene (DNA, Compound b), tetra(t-butyl)perylene (Compound c) system or the like have been known. However, extensive research and development should be performed with respect to these materials. The distryl compound system of Idemitsu-Kosan, which is known to have highest efficiency up to now, has 6 lm/W of power efficiency and beneficial device lifetime of more than 30,000 hr. However, the color is unsuitable (sky-blue), when it is applied to a full-colored display. In case of blue electroluminescentce, it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength. However, it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue. In addition, the research and development of such materials are urgently demanded because of the problems in color purity, efficiency and thermal stability.
For host materials having high efficiency and long life, various substances with different backbones, such as dispiro-prolene-anthracene (TBSA), ter-spirofluorene (TSF) and bitriphenylene (BTP), have been developed, but they are not satisfactory in terms of color purity and luminous efficiency.
The compound TBSA as reported by Gyeongsang National University and Samsung SDI (Kwon, S. K. et al., Advanced Materials, 2001, 13, 1690; Japanese Patent Laid-Open JP 2002121547), showed luminous efficiency of 3 cd/A at 7.7 V, and relatively good color coordinate of (0.15, 0.11), but it was an example applied as material for a single layer, being inappropriate for practical use.
The compound TSF reported by Taiwan National University (Wu, C. -C. et al., Advanced Materials, 2004, 16, 61; US Patent Publication US 2005040392) showed relatively good external quantum efficiency of 5.3%, but it is still insufficient for practical use.
The compound BTP reported by Chingwha National University of Taiwan (Cheng, C. -H. et al., Advanced Materials, 2002, 14, 1409; US Patent Publication 2004076852) showed luminous efficiency of 2.76 cd/A and relatively good color coordinate of (0.16, 0.14), but this was still insufficient for practical use.
As described above, conventional materials are constituted by a single layer, not forming host-dopant thin layer, and is difficult to be used practically from the aspect of color purity and efficiency. It lacks reliable data with respect to its long life.
In the meanwhile, according to a patent application of Mitsui Chemicals (Japan) (US Patent Publication 7,166,240), the compounds shown below have the absorption spectrum at 390 to 430 nm, with luminous efficiency of 4.6 cd/A. However, on the basis of these data, the compounds with above absorption wavelength range, electroluminescence of greenish blue color is anticipated, and the Patent Publication indicates the color as bluish green color.
Particularly, embodiment of pure blue color is impossible with the symmetrical structure of the Patent Publication, and the material, which cannot provide pure blue luminescence, is inadequate to be practically applied to a full-colored display.
In the meanwhile, as a green fluorescent material, a system wherein a coumarine derivative (Compound d, C545T), a quinacridone derivative (Compound e), DPT (Compound f) or the like is doped to Alq (a host), as a dopant, in a concentration from several % to not more than 20 % has been developed and widely used. However, the conventional electroluminescent materials suffer from significant problem in view of lifetime with noticeable reduction of initial efficiency, though they show good performance in view of initial luminous efficiency at the level of practical use. Thus, the materials have limitations to be employed for a high performance panel of larger screen.
Further, since the OLED devices manufactured therefrom cannot give satisfactory level of device life by any means, required is development of host material having far improved stability and performances.
The object of the invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinate, as compared to conventional host materials.
Another object of the invention is to provide an organic electroluminescent device of high efficiency and long life by employing the organic electroluminescent compound as electroluminescent material.
The present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and organic electroluminescent devices comprising the same. The organic electroluminescent compounds according to the invention exhibit high luminous efficiency, and excellent color purity and life property of the material, so that OLED’s with very excellent operation life can be manufactured therefrom.
[Chemical Formula 1]
wherein,
A1 through A5 independently represent CR31 or N;
R1 through R17 and R31 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30) aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl which is 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 which is fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl which is 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], 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 group 
to form a ring;
L1 and L2 independently represent a chemical bond, or -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-, excluding the case where both L1 and L2 represent chemical bonds;
R51 through R58 are defined as for R1 through R17;
ring A is a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, 5- or 6-membered heteroaromatic ring fused with an aromatic ring, or a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring;
the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
m represents an integer 1 or 2.
The ‘alkyl’, ‘alkoxy’ and other substituents containing ‘alkyl’ moiety described herein include both linear and branched species.
The term ‘aryl’ described herein represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom. Aryl groups include monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through chemical bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto. The naphthyl may be 1-naphthyl or 2-naphthyl, the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl, and the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
The term ‘heteroaryl’ described herein means an aryl group containing from 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms. The heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated. The structures having one or more heteroaryl group(s) bonded through a single bond are also included. The heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like. Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl and benzodioxolyl; and corresponding N-oxides (for example, pyridyl N-oxide, quinolyl N-oxide) and quaternary salts thereof; but they are not restricted thereto.
The alkyl groups in ‘(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, (C1-C30)alkylcarbonyloxy’ described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10. The aryl groups in ‘(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 restricted carbon number from 6 to 20, or from 6 to 12. The heteroaryl groups in ‘(C3-C30)heteroaryl’ may have restricted carbon number from 4 to 20, or from 4 to 12. The cycloalkyl groups in ‘(C3-C30)cycloalkyl’ may have restricted carbon number from 3 to 20, or from 3 to 7. The alkenyl or alkynyl of ‘(C2-C30)alkenyl or alkynyl’ may have restricted carbon number from 2 to 20, or from 2 to 10.
The term ‘substituted or unsubstituted(or with or without) substituent(s)’ described herein means having one or more substituent(s) independently selected from 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), a 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P, a 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, adamantly, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR41R42, BR43R44, PR45R46, P(=O)R47R48[wherein R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl], (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 that adjacent substituent(s) are linked together to form a ring.
Each group of R1 through R17 and R31 is independently selected from aryl groups such as phenyl, naphthyl, anthryl, biphenyl, fluorenyl, phenanthryl, pyrenyl and perylenyl; heteroaryl groups such as pyridinyl, pyrazinyl, furyl, thienyl, selenophenyl, quinolinyl, quinoxalinyl, phenanthrolinyl, carbazolyl and benzopiperidinyl; aryl groups fused with cycloalkyl, such as tetrahydronaphthyl; heterocycloalkyl groups fused with one or more aromatic ring, such as benzopiperidino, dibenzomorpholino and dibenzoazepino; NR71R72, BR73R74, PR75R76, P(=O)R77R78 [wherein R71 through R78 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C3-C30)heteroaryl], but not being restricted thereto, and each group may be further substituted by a substituent, as described for Chemical Formula (1).
The group 
can be specifically exemplified by following structures:
wherein, R51 through R55 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.
The organic electroluminescent compounds according to the present invention can be more specifically exemplified by the following compounds, but they are not restricted thereto.
The process for preparing the organic electroluminescent compounds according to the present invention is exemplified by Reaction Schemes (1) or (2), but not being restricted thereto. Various modifications of the process would be obvious for a person having ordinary skill in the art, and the substituents of the reaction schemes are defined as for Chemical Formula (1), unless they are specified otherwise.
[Reaction Scheme 1]
[Reaction Scheme 2]
The present invention also provides an organic electroluminescent device which is comprised of 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 organic electroluminescent compound(s) represented by Chemical Formula (1). The organic electroluminescent compound is employed as host material of the electroluminescent layer.
The organic electroluminescent device according to the present invention is characterized in that the organic layer comprises an electroluminescent layer containing one or more organic electroluminescent compound(s) represented by Chemical Formula (1), as well as one or more dopant(s). The dopant to be applied to an organic electroluminescent device according to the invention is not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (2):
[Chemical Formula 2]
wherein,
Ar41 and Ar42 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), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar41 and Ar42 may be linked each other via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
when i is 1, Ar43 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures;
when i is 2, Ar43 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures;
each one of Ar51 independently represents (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
R901 independently represents hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
i represents an integer from 1 to 4;
j represents an integer from 1 to 4; and
k represents an integer 0 or 1.
The dopant compounds represented by Chemical Formula (2) can be exemplified by those described in Korean Patent Application No. 10-2009-0023442. More preferably they are selected from the following structures, but not restricted thereto.
The organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1). The arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
In an organic electroluminescent device according to the present invention, the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the electroluminescent compound represented by Chemical Formula (1). The organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
The organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1), to form an organic electroluminescent device emitting white light. The compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
In an organic electroluminescent device according to the present invention, it is preferable to arrange one or more layer(s) (here-in-below, referred to as the ‘surface layer’) selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to arrange a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the EL medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer. As the result, stability in operation can be obtained.
Examples of chalcogenides preferably include SiOx (1≤X≤2), AlOx (1≤X≤1.5), SiON, SiAlON, or the like. Examples of metal halides preferably include LiF, MgF2, CaF2, fluorides of rare earth metal or the like. Examples of metal oxides preferably include Cs2O, Li2O, MgO, SrO, BaO, CaO, or the like.
In an organic electroluminescent device according to the present invention, it is also preferable to arrange, on at least one surface of the pair of electrodes thus manufactured, a mixed region of electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
A white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
The organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life property of the material, so that OLED’s having very good operation life can be manufactured therefrom.
The present invention is further described by referring to representative compounds with regard to the organic electroluminescent compounds according to the invention, preparation thereof and luminescent properties of the devices manufactured therefrom, but those examples are provided for illustration of the embodiments only, not being intended to limit the scope of the invention by any means.
[Preparation Example 1] Preparation of Compound (1)
Preparation of Compound (A)
A mixture of phenanthrene (20.0 g, 112.21 mmol), NBS (30.0 g, 168.31 mmol), AIBN (27.6 g, 168.31 mmol) and CCl4 (1000 mL) was stirred under reflux for 3 hours. When the reaction was completed, the reaction mixture was extracted with dichloromethane and distilled water. The extract was concentrated by using a rotary evaporator to obtain oily product. Purification via column chromatography gave Compound (A) (17.3 g, 67.3 mmol).
Preparation of Compound (B)
Compound (A) (29.5 g, 108.0 mmol) was dissolved in purified tetrahydrofuran (350 mL) under nitrogen atmosphere, and the solution was chilled to -78℃. To the solution, slowly added was 2.5 M n-butyllithium (in hexane) (56.2 mL, 140.4 mmmol), and the resultant mixture was stirred for 1 hour. After adding trimethylborate (19.6 mL, 172.8 mmol), the mixture was slowly warmed to 25℃, and stirred at the same temperature for 1 day.
Then, aqueous 1 M HCl solution (400 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (300 mL) and the extract was dried under reduced pressure. Recrystallization from dichloromethane (20 mL) and hexane (300 mL) gave Compound (B) (13.5 g, 56.7 mmol).
Preparation of Compound (1)
A mixture of Compound (B) (5.0 g, 13.4 mmol), 9-phenyl-anthracene-10-boronic acid (4.8 g, 16.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), aqueous 2 M K2CO3 solution (20 mL), toluene (100 mL) and ethanol (50 mL) was stirred under reflux for 12 hours. The reaction mixture was then extracted with distilled water and ethyl acetate. The extract was dried and evaporated under reduced pressure. Purification through a column gave Compound (1) (4.3 g, 7.9 mmol, 58.8%).
[Preparation Example 2] Preparation of Compound (84)
Preparation of Compound (C)
To a reaction vessel containing 2-chloroanthraquinone (30.0 g, 123.63 mmol), phenylboronic acid (18.09 g, 148.36 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (Pd(PPh3)2Cl2) (8.68 g, 12.63 mmol), added was toluene (800 mL) and ethanol (300 mL) as solvent with stirring. Then, 2M solution of sodium carbonate (400 mL) was added, and the resultant mixture was stirred under reflux at 120℃. After stirring for 3 hours, the temperature was lowered to room temperature, and water (300 mL) was added. The mixture was extracted with ethyl acetate (300 mL). The extract was evaporated under reduced pressure to remove solvent and obtain solid compound. The solid compound was completely dissolved in 300 mL of tetrahydrofuran, and filtered through silica. Removal of solvent via filtration under reduced pressure gave Compound (C) (26.8 g, 100.89 mmol).
Preparation of Compound (D)
In a reaction vessel containing Compound (C) (85.0 g, 299.07 mmol), added was acetic acid (700 mL). With stirring, hydroiodic acid (HI, 700 mL), and hyperphosphorous acid (H3PO2) (600 mL) were added thereto. After stirring under reflux for 16 hours, the reaction mixture was cooled and extracted with dichloromethane. Purification through a column (dichloromethane/n-hexane = 1/10) gave Compound (D) (72.85 g, 286.43 mmol).
Preparation of Compound (E)
To a reaction vessel containing Compound (D) (25.0 g, 98.53 mmol) and N-bromosuccinimide (NBS) (19.3 g, 108.38 mmol), added was dichloromethane (800 mL) as solvent, and the mixture was stirred at room temperature for 20 hours. When the reaction was completed, the reaction mixture was washed with water (800 mL), and extracted with dichloromethane (300 mL). The extract was filtered under reduced pressure, and the resultant compound was recrystallized from methanol (500 mL) to obtain Compound (E) (30.2 g, 90.03 mmol).
Preparation of Compound (F)
To a reaction vessel containing Compound (E) (5.5 g, 14.35 mmol) and Compound (B) (4.1 g, 17.22 mmol), added were trans-dichlorobis(triphenylphosphine)palladium (II) (Pd(PPh3)2Cl2) (1.0 g, 1.44 mmol) and toluene (140 mL) as solvent, and the mixture was stirred. Ethanol (70 mL) and 2 M sodium carbonate solution (70 mL) were added thereto, and the resultant mixture was stirred under reflux under nitrogen atmosphere for 5 hours. Then the reaction mixture was cooled to room temperature, and methanol (200 mL) was added thereto to produce solid. The solid product thus obtained was filtered, and heated under reflux with methanol (200 mL). Recrystallization gave Compound (F) (4.0 g, 8.05 mmol).
Preparation of Compound (G)
Compound (F) (4.0 g, 8.05 mmol) and N-bromosuccinimide (1.72 g, 9.66 mmol) were dissolved in dichloromethane (100 mL), and the solution was stirred at room temperature. After 20 hours, water (200 mL) was added thereto to quench the reaction. The mixture was then extracted with dichloromethane (100 mL) and the extract was evaporated under reduced pressure to remove the solvent. The solid product thus obtained was heated under reflux with methanol (200 mL). Recrystallization gave Compound (G) (3.6 g, 6.25 mmol).
Preparation of Compound (84)
To a reaction vessel containing Compound (G) (5.0 g, 8.69 mmol), phenylboronic acid (2.8 g, 11.29 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (Pd(PPh3)2Cl2) (0.6 g, 8.7 mmol), added were 2 M sodium carbonate (Na2CO3) solution (15 mL) and toluene (100 mL) as solvent. After stirring under reflux for 2 hours, the reaction mixture was extracted with dichloromethane (200 mL), and the extract was filtered under reduced pressure. Recrystallization from methanol (300 mL) gave Compound (84) (4.5 g, 74%).
According to the same procedure as described in Preparation Example 1, prepared were organic electroluminescent compounds (Compounds 1 to 136), of which 1H NMR and MS/FAB data are listed in Table 1.
[Table 1]
[Example 1] Manufacture of OLED’s by using organic electroluminescent compounds according to the present invention
OLED devices were manufactured by using the electroluminescent material according to the invention.
First, a transparent electrode ITO thin film (15 Ω/□) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4＂-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10-6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
Then, to another cell of the vacuum vapor-deposit device, charged was N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB), and electric current was applied to the cell to evaporate NPB, thereby providing vapor-deposit of a hole transport layer of 20 nm of thickness on the hole injection layer.
After forming the hole injecting layer and the hole transport layer, an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (84) according to the present invention as host, and Compound (E) was charged to another cell as dopant. Two substances were evaporated at different rates to provide vapor-deposition at a concentration of 2 to 5% by weight on the basis of the host. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
Then, tris(8-hydroxyquinoline)aluminum (III) (Alq) (of which the structure is shown below) was vapor-deposited as an electron transport layer (6) with a thickness of 20 nm, and lithium quinolate (Liq) (of which the structure shown below) was vapor-deposited as an electron injecting layer with a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10-6 torr.
[Comparative Example 1] Manufacture of an OLED by using conventional electroluminescent compound
After forming a hole injecting layer (3) and a hole transport layer (4) according to the same procedure as described in Example 1, dinaphthylanthracene (DNA) was charged to another cell of said vacuum vapor-deposit device as electroluminescent host material, while Compound (E) was charged to still another cell. Two substances were evaporated at different rates to provide vapor-deposition at a concentration of 2 to 5% by weight on the basis of the host. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
Then, an electron transport layer (6) and an electron injecting layer (7) were vapor-deposited according to the same procedures as in Example 1, and Al cathode (8) was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
The luminous efficiencies of the OLED s comprising the organic electroluminescent compounds according to the present invention (Example 1) and conventional electroluminescent compound (Comparative Examples 1) were measured at 5,000 cd/m2, respectively, and the results are shown in Table 2.
[Table 2]
As can be seen from Table 2, the organic electroluminescent compounds according to the present invention are able to realize a device having higher luminous efficiency with lower operation voltage while maintaining comparable or higher color purity, as compared to that of Comparative Example 1.
[Example 2] Manufacture of OLED’s by using organic electroluminescent compounds according to the present invention
After forming the hole injecting layer and the hole transport layer according to the same procedure as described in Example 1, an electroluminescent layer was vapor-deposited thereon. To one cell of a vacuum vapor-deposit device, charged was Compound (1) according to the present invention as electroluminescent material, and Compound (A) (of which the structure is shown below) was charged to another cell. Two cells were heated at the same time to provide vapor-deposition with a deposition rate of Compound (A) at 2 to 5% by weight. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
Then, an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
[Comparative Example 2] Luminous properties an OLED using conventional electroluminescent material
After forming a hole injecting layer and a hole transport layer according to the same procedure as described in Example 1, dinaphthylanthracene (DNA) was charged to another cell of said vacuum vapor-deposit device as electroluminescent host material, while Compound (A) (of which the chemical structure is shown below) was charged to still another cell, as blue electroluminescent material. An electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer at a vapor-deposition rate of 100:1.
Then, an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
The luminous efficiencies of the OLED’s comprising the organic electroluminescent compounds according to the present invention (Example 2) and conventional electroluminescent compound (Comparative Example 2) were measured at 1,000 cd/m2, respectively, and the results are shown in Table 3.
[Table 3]
As can be seen from Table 3, the blue electroluminescent devices manufactured by employing the electroluminescent material according to the present invention showed comparable or higher luminous efficiency, as compared to that of Comparative Example 2.
Claims (8)
- An organic electroluminescent compound represented by Chemical Formula (1):[Chemical Formula 1]
wherein,A1 through A5 independently represent CR31 or N;R1 through R17 and R31 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30) aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl which is 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 which is fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl which is 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28 [wherein R21 through R28 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], 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 groupto form a ring;
L1 and L2 independently represent a chemical bond, or -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-, excluding the case where both L1 and L2 represent chemical bonds;R51 through R58 are defined as for R1 through R17;ring A is a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, 5- or 6-membered heteroaromatic ring fused with an aromatic ring, or a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered heteroaromatic ring;the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; andm represents an integer 1 or 2. - The organic electroluminescent compound according to claim 1, wherein each substituent represented by one of R1 through R17, R21 through R28, R31 and R51 through R58 is further substituted by one or more substituent(s) selected from a group consisting of hydrogen, 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, (C3-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, NR41R42, BR43R44, PR45R46, P(=O)R47R48 [wherein R41 through R48 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 the adjacent substituents are linked each other to form a ring.
- An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 or 2.
- The organic electroluminescent device according to claim 3, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) according to claim 1 and one or more dopant(s) represented by Chemical Formula (2):[Chemical Formula 2]
wherein,Ar41 and Ar42 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), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar41 and Ar42 may be linked each other via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;when i is 1, Ar43 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures;
when i is 2, Ar43 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures;
each one of Ar51 independently represents (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);R901 independently represents hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);the heterocycloalkyl or the heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;i represents an integer from 1 to 4;j represents an integer from 1 to 4; andk represents an integer 0 or 1. - The organic electroluminescent device according to claim 4, 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, wherein the organic layer further comprises one or more metal(s) 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, or complex(es) thereof.
- The organic electroluminescent device according to claim 4, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 4, which is an organic electroluminescent device emitting white light comprising in the organic layer one or more organic layer(s) emitting red, green or blue light.
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| KR10-2009-0027434 | 2009-03-31 | ||
| KR1020090027434A KR20100109050A (en) | 2009-03-31 | 2009-03-31 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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Also Published As
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|---|---|
| KR20100109050A (en) | 2010-10-08 |
| WO2010114256A3 (en) | 2010-12-16 |
| TW201105775A (en) | 2011-02-16 |
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