WO2011136482A1 - 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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- WO2011136482A1 WO2011136482A1 PCT/KR2011/002489 KR2011002489W WO2011136482A1 WO 2011136482 A1 WO2011136482 A1 WO 2011136482A1 KR 2011002489 W KR2011002489 W KR 2011002489W WO 2011136482 A1 WO2011136482 A1 WO 2011136482A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- aryl
- independently represent
- heteroaryl
- cycloalkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 79
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 239000010410 layer Substances 0.000 claims description 35
- -1 morpholino, thiomorpholino, piperidino Chemical group 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000005104 aryl silyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000005549 heteroarylene group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 229910052702 rhenium Inorganic materials 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005584 chrysenylene group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005565 oxadiazolylene group Chemical group 0.000 claims description 2
- 125000005563 perylenylene group Chemical group 0.000 claims description 2
- 125000005548 pyrenylene group Chemical group 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000005556 thienylene group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 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
- 125000005558 triazinylene group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 27
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- 0 *N(*)I(C=CI*)I Chemical compound *N(*)I(C=CI*)I 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 238000000034 method Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 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
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- 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
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-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
- 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
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 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
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 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
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 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
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical class [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
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- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Definitions
- the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as a blue electroluminescent material and an organic electroluminescent device employing the same as a dopant.
- the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
- the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 1 through R 10 and R 31 through R 35 ; the arylene or heteroarylene of L 1 and L 2 ; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 11 and R 12 ; and the fused ring formed by link between R 11 and R 12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;
- n an integer 0, 1 or 2.
- 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" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
- the aryl 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” or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
- the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
- the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
- the alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
- alkyl includes linear or branched saturated monovalent hydrocarbon radical containing only carbon atoms and hydrogen atoms, or a combination thereof.
- the "cycloalkyl” includes polycyclic hydrocarbon rings such as adamantyl or bicycloalkyl as well as a monocyclic ring.
- aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryl groups having single bond(s) therebetween.
- 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.
- the heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
- the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
- Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothi
- organic electroluminescent compound according to the present invention includes compounds represented by Chemical Formula 2 or 3 below:
- L 11 and L 12 independently represent (C6-C30)arylene, (C2-C30)heteroarylene or ;
- L 21 and L 22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;
- R 2 , R 3 , R 5 , R 6 , R 8 and R 9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;
- R 41 through R 44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR 21 , O or S, wherein R 21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or R a R b R c Si- [wherein R
- R 1 , R 4 , R 7 and R 10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NR e R f [wherein R e and R f independently represent (C1-C30)alkyl or (C6-C30)aryl], R a R b R c Si- [wherein R a , R b and R c independently represent (C1-C30)alkyl or (C6-C30)aryl] or R d Y- [wherein Y represents O or S, and R d represents (C1-C30)alkyl or (C6-C30)aryl];
- the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 1 through R 10 ; and the arylene or heteroarylene of L 11 , L 12 , L 21 and L 22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; and
- n an integer 0, 1 or 2.
- R 31 through R 35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring;
- L 21 and L 22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;
- R 1 , R 4 , R 7 and R 10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; and
- the and may be independently selected from the following structures but are not limited thereto:
- R 31 through R 35 independently represent (C1-C30)alkyl or (C6-C30)aryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring.
- organic electroluminescent compound according to the present invention may be prepared as shown in following Schemes 1 and 2 but are not limited thereto.
- R 1 through R 10 , L 1 , L 2 , R 11 and R 12 are the same as defined in Chemical Formula 1.
- an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
- the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more host(s) besides one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent dopant.
- the host applied to the organic electroluminescent device of the present invention is not specifically limited but may be selected from following Chemical Formula 4 or 5.
- L 101 represents (C6-C30)arylene or (C4-C30)heteroarylene;
- L 102 represents anthracenylene
- Ar 101 through Ar 104 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar 101 through Ar 104 is further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C
- a, b, c and d independently represent an integer from 0 to 4.
- the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated.
- the doping concentration may be 0.5 to 10 wt%.
- the electroluminescent host according to the present invention provides excellent conductivity for holes and electrons, as well as very superior stability and remarkably improved luminescence efficiency and operation life. Accordingly, when the compound represented by Chemical Formula 4 or 5 is selected as an electroluminescent host, it may considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
- the organic electroluminescent device may comprise the organic electroluminescent compound of Chemical Formula 1 and may comprise one or more compound(s) selected from the group consisting of arylamine or styrylamine compounds.
- arylamine or styrylamine compounds are provided in Paragraph Nos. ⁇ 212> to ⁇ 224> of KR Patent Application No. 10-2008-0060393 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 compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
- the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
- the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
- the organic layer may include an electroluminescent layer and a charge generating layer.
- An organic electroluminescent device having a pixel structure of independent light-emitting mode may be embodied, wherein the organic electroluminescent device including the organic electroluminescent compound represented by Chemical Formula 1 of the present invention is taken as a subpixel and one or more subpixel(s) including one or more metal compound(s) selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag are patterned in parallel at the same time.
- the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
- a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
- the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
- the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
- a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
- the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
- the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
- the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
- Organic electroluminescent compounds 1 to 111 were prepared according to the procedure of Preparation Examples 1 and 3. 1 H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
- An OLED device was manufactured using the electroluminescent material according to the present invention.
- a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- an electroluminescent layer was formed thereon as follows.
- DNA (Examples 1 to 3) was placed in a cell of the vacuum vapor deposition apparatus as a host, and the compound according to the present invention was placed in another cell as a dopant.
- the two materials were vapor-deposited at a rate of 100:3 to form an electroluminescent layer having a thickness of 30 nm on the hole transport layer.
- Alq tris(8-hydroxyquinoline)-aluminum(III)
- Liq lithium quinolate
- an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
- Each compound used in the OLED had been purified by vacuum sublimation at 10 -6 torr.
- Luminescence efficiency of the OLED devices containing the organic electroluminescent compound according to the present invention manufactured in Examples 1 to 3 was measured at 1,000 cd/m 2 . The result is given in Table 2.
- the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
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Abstract
Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency in blue color and excellent life property of the material, it may be used to manufacture OLED devices having very superior operation life.
Description
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as a blue electroluminescent material and an organic electroluminescent device employing the same as a dopant.
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials. The low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure. Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained and it is expected that a color display device will be realized.
In the meanwhile, for 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) of Kodac, 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 power efficiency and beneficial device lifetime of more than 30,000 hr. However, when it is applied to a full-colored display, the lifetime is merely several thousand hours, owing to decrease of color purity over operation time. In case of blue electroluminescence, 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. Furthermore, the research and development of such materials are urgent because of the problems in color purity, efficiency and thermal stability.
With intensive efforts to overcome the problems of conventional techniques as described above, the present inventors have invented novel organic electroluminescent compounds which realize organic electroluminescent devices having excellent luminous efficiency and noticeably improved life property. The object of the present invention is to provide organic electroluminescent compounds having the backbone with appropriate color coordinate to provide better luminous efficiency and device life compared with conventional dopant material, while overcoming the problems described above, and a highly efficient and long life organic electroluminescent device using the organic electroluminescent compounds.
Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. The organic electroluminescent compound is a compound represented by Chemical Formula 1. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
[Chemical Formula 1]
wherein
R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl] or , except for the case where two of R1, R4, R7 and R10 are hydrogen;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
L1 represents a single bond, (C6-C30)arylene or (C2-C30)heteroarylene;
R11 and R12 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], 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 alicyclic ring or a mono- or polycyclic aromatic ring;
the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10 and R31 through R35; the arylene or heteroarylene of L1 and L2; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R11 and R12; and the fused ring formed by link between R11 and R12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
m represents an integer 0, 1 or 2.
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" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl 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" or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The heteroaryl of "(C3-C30)heteroaryl" may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30)cycloalkyl" may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl" may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
In the present invention, "alkyl" includes linear or branched saturated monovalent hydrocarbon radical containing only carbon atoms and hydrogen atoms, or a combination thereof. In the present invention, the "cycloalkyl" includes polycyclic hydrocarbon rings such as adamantyl or bicycloalkyl as well as a monocyclic ring.
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 aryl groups having single bond(s) therebetween. 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. The heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
Also, the organic electroluminescent compound according to the present invention includes compounds represented by Chemical Formula 2 or 3 below:
[Chemical Formula 2]
[Chemical Formula 3]
wherein
L21 and L22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;
R41 through R44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], 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 alicyclic ring or a mono- or polycyclic aromatic ring;
R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10; and the arylene or heteroarylene of L11, L12, L21 and L22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; and
m represents an integer 0, 1 or 2.
The L11 and L12 independently represent phenylene, naphthalene, biphenylene, phenanthrylene, pyrazinylene, triazinylene, quinolylene, phenanthrolinylene, thienylene, furylene, selenophenylene, thiadiazolylene, oxadiazolylene, selenadiazolylene or quinoxalinylene, or a divalent group selected from the following structures:
R31 through R35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring;
L21 and L22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl;
R41 through R44 independently represent cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, triazinyl, pyrimidyl or ;
R1, R4, R7 and R10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; and
L11, L12, L21, L22, R1 through R10 and R41 through R44 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl, but are not limited thereto.
wherein
R31 through R35 independently represent (C1-C30)alkyl or (C6-C30)aryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring.
More specifically, the organic electroluminescent compound according to the present invention may be exemplified by following compounds but are not limited thereto:
The organic electroluminescent compound according to the present invention may be prepared as shown in following Schemes 1 and 2 but are not limited thereto.
[Scheme 1]
[Scheme 2]
wherein
R1 through R10, L1, L2, R11 and R12 are the same as defined in Chemical Formula 1.
Provided is an organic electroluminescent device, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
In the organic electroluminescent device of the present invention, the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more host(s) besides one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent dopant. The host applied to the organic electroluminescent device of the present invention is not specifically limited but may be selected from following Chemical Formula 4 or 5.
[Chemical Formula 4]
(Ar101)a-L101-(Ar102)b
[Chemical Formula 5]
(Ar103)c-L102-(Ar104)d
wherein
L101 represents (C6-C30)arylene or (C4-C30)heteroarylene;
L102 represents anthracenylene;
Ar101 through Ar104 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar101 through Ar104 is further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl; and
a, b, c and d independently represent an integer from 0 to 4.
The electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated. When a mixture of host-dopant is used according to the constitution of the present invention, noticeable improvement in luminous efficiency by the electroluminescent host may be confirmed. The doping concentration may be 0.5 to 10 wt%. When compared with existing other host materials, the electroluminescent host according to the present invention provides excellent conductivity for holes and electrons, as well as very superior stability and remarkably improved luminescence efficiency and operation life. Accordingly, when the compound represented by Chemical Formula 4 or 5 is selected as an electroluminescent host, it may considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
The organic electroluminescent device may comprise the organic electroluminescent compound of Chemical Formula 1 and may comprise one or more compound(s) selected from the group consisting of arylamine or styrylamine compounds. Specific examples of arylamine or styrylamine compounds are provided in Paragraph Nos. <212> to <224> of KR Patent Application No. 10-2008-0060393 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 compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
An organic electroluminescent device having a pixel structure of independent light-emitting mode may be embodied, wherein the organic electroluminescent device including the organic electroluminescent compound represented by Chemical Formula 1 of the present invention is taken as a subpixel and one or more subpixel(s) including one or more metal compound(s) selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag are patterned in parallel at the same time.
Further, the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
The chalcogenide may be, for example, SiOx (1 = x = 2), AlOx (1 = x = 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 2
Preparation of Compound F
Compound D (10g, 16.99mmol) was dissolved in THF (100ml) and n-BuLi (50.99ml, 20.39mmol, 2.5M in hex) was slowly added thereto at -78℃. After stirring the mixture for 1 hour, DMF (3.2ml, 54.39mmol) was added thereto. After slowly raising temperature, the mixture was stirred at room temperature for 12 hours. Distilled water was added to the mixture and the mixture was extracted with MC. After drying with magnesium sulfate and distillation under reduced pressure, Compound F (4.7, 9.65mmol, 56.85%) was obtained by column separation.
Preparation of Compound H
Compound G (26g, 95.12mmol) and NaBH4 (5.39g, 142.68mmol) were mixed with THF (300ml). Methanol was slowly added to the mixture at 0℃. 2 hours later, the mixture was extracted with EA and washed with distilled water. After drying with magnesium sulfate, Compound H (26g, 94.42mmol, 99.27%) was obtained by column separation.
Preparation of Compound I
Compound H (26g, 94.42mmol) was dissolved in triethylphosphite (100ml) and iodine (23.96g, 94.42mmol) was dissolved in triethylphosphite (50ml). The two solutions were slowly mixed, and stirred at 100℃. 12 hours later, the mixture was cooled to room temperature and distilled under reduced pressure. The mixture was extracted with MC and washed with distilled water. After drying with magnesium sulfate and distillation under reduced pressure, Compound I (32g, 80.92mmol, 86.09%) was obtained by column separation.
Preparation of Compound 2
Compound F (4.7g, 9.65mmol) and Compound I (7.63g, (19.3mmol) were dissolved in THF (50ml) and potassium tert-butoxide (24ml, 24.12mmol, 1.0M in THF) was added to the mixture at 0℃. 2 hours later, distilled water was added and the mixture was extracted with MC. After drying with magnesium sulfate and distillation under reduced pressure, Compound 2 (4.3g, 4.43mmol, 45.97%) was obtained by column separation.
[Preparation Example 2] Preparation of Compound 101
Preparation of Compound L
After diphenylamine (20g, 118.2mmol), Compound k (24.04g, 130.02mmol), Pd(OAc)2 (1.3g, 5.91mmol), cesium carbonate (96.2g, 295.50mmol) and toluene (500ml) were mixed and tri-t-butylphophine (5.8ml, 11.82mmol, in 50% xylene) was stirred at 120℃. 10 hours later, the mixture was cooled to room temperature. Distilled water was added to the mixture and the mixture was extracted with EA. After drying with magnesium sulfate and distillation under reduced pressure, Compound L (14.7g, 53.58mmol, 45.41%) was obtained by column separation.
Preparation of Compound 101
Compound 101 (3g, 32%) was obtained using Compound L as an intermediate in the same manner as that of Preparation Example 1.
[Preparation Example 3] Preparation of Compound 106
Preparation of Compound M
After 4-bromotoluen (6.8ml, 55.2mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. The compound was dissolved by adding THF (200ml) to the round bottom flask and cooled to -78℃. After n-butyl lithium (22ml, 55.2mmol) was slowly added to the round bottom flask, the mixture was stirred for 1 hour while maintaining low temperature. 1 hour later, phenanthrenequinone (5g, 24mmol) was added at -78℃, and the mixture was stirred for 3 hours while heating to room temperature. Upon completion of the reaction, the mixture was extracted with ethyl ether and dried by removing remaining moisture with magnesium sulfate. Compound M (5.9g, 14.8mmol, 63%) was obtained by performing column separation on the obtained material.
Preparation of Compound N
Compound M (5g, 12.6mmol) was dissolved in AcOH (100ml) in a round bottom flask and stirred under reflux. Zn powder (4g, 63mmol) was added to the mixture. A solution that HCl (2.5ml) was dissolved in AcOH (12ml) was added to the round bottom flask. 30 minutes later, a solution that HCl (2.5m) was dissolved in Zn powder (4g, 63mmol) and AcOH (12ml) was added to the mixture. The mixture was stirred until there is no more reaction in thin layer chromatography (TLC). The mixture was extracted with MC, distilled water, sodium bicarbonate solution and NaCl solution and dried by removing remaining moisture with magnesium sulfate. Compound N (4.3g, 11.9mmol, 97%) was obtained by performing column separation on the obtained material.
Preparation of Compound O
After Compound N (5.8g, 16.1mmol), NBS (6.6g, (37mmol) and benzoyl peroxide (391mg, 1.61mmol) were added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding CCl4 (193ml) to the round bottom flask, the mixture was stirred under reflux for 4 hours. Upon completion of the reaction, the mixture was extracted with MC and dried by removing remaining moisture with magnesium sulfate to go on to the next reaction.
Preparation of Compound P
After Compound O (11g, 21.3mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding triethylphosphite (40ml) to the round bottom flask, the mixture was stirred under reflux for 7 hours. Upon completion of the reaction, triethylphosphite was removed by a distillation device. Compound P (12.2g, 19.3mmol, 91%) was obtained by column separation.
Preparation of Compound 106
After Compound P (3g, 4.75mmol) and 4-(diphenylamino)benzaldehyde (3.1g, 11.4mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding THF (200ml) to the round bottom flask and cooled to 0℃, potassium-tert-butoxide (57ml, 57mmol) was slowly added and stirred for 10 minutes. After heated to room temperature, the mixture was stirred for 1 hour. Upon completion of the reaction, the mixture was extracted with EA and dried by removing remaining moisture with magnesium sulfate. Compound 106 (2g, 2.3mmol, 50%) was obtained by performing column separation on the obtained material.
Organic electroluminescent compounds 1 to 111 were prepared according to the procedure of Preparation Examples 1 and 3. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
Table 1
Comp. | 1H NMR(CDCl3, 200 MHz) | MS/FAB | |
found | calculated | ||
1 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 869.10 | 868.38 |
2 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.58~7.59(6H, m), 7.73~7.77(6H, m), 7.92(2H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) | 969.22 | 968.41 |
3 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.55(4H, m), 7.61(2H, m), 7.77(4H, m), 7.98~8.12(8H, m), 8.42(2H, m), 8.55(2H, m), 9.09(2H, m) | 969.22 | 968.41 |
4 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2~7.25(16H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1021.29 | 1020.44 |
5 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2~7.25(16H, m), 7.58~7.59(6H, m), 7.73~7.77(6H, m), 7.92(2H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) | 1121.41 | 1120.48 |
6 | δ= 2.34(6H, s), 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.29~7.33(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 897.15 | 896.41 |
7 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.3(4H, m), 7.39(4H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 905.08 | 904.36 |
8 | δ= 3.83(6H, s), 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.05(4H, m), 7.2(8H, m), 7.68(4H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 929.15 | 928.40 |
9 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.77(4H, m), 7.98~7.99(6H, m), 8.12(2H, m), 8.75(4H, m), 9.09(2H, m) | 871.08 | 870.37 |
10 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.17~7.2(10H, m), 7.4(2H, m), 7.69(2H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 881.16 | 880.29 |
11 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.98(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(12H, m), 7.73(2H, m), 7.87(2H, m), 7.98(2H, m), 8.07~8.12(4H, m), 9.09(2H, m) | 969.22 | 968.41 |
12 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.49~7.57(14H, m), 7.74(2H, m), 7.83~7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 969.22 | 968.41 |
13 | δ= 6.63(8H, m), 6.69(4H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(16H, m), 7.64(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1021.29 | 1020.44 |
14 | δ= 0.9(12H, m), 1.91(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1157.53 | 1156.57 |
15 | δ= 1.51(8H, m), 2.09(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1153.49 | 1152.54 |
16 | δ= 1.48(12H, m), 2.02(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1181.55 | 1180.57 |
17 | δ= 3.49(8H, s), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(16H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1249.58 | 1248.54 |
18 | δ= 6.63(8H, m), 6.75~6.81(8H, m), 6.95(4H, m), 7.08(2H, m), 7.2(8H, m), 7.38~7.52(18H, m), 7.58(4H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.59(2H, m), 9.09(2H, m) | 1199.48 | 1198.50 |
19 | δ= 0.66(12H, s), 6.63(8H, m), 6.69(2H, m), 6.81(4H, m), 6.95~6.99(6H, m), 7.2(8H, m), 7.27(2H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.98(2H, m), 8.12~8.17(4H, m), 9.09(2H, m) | 1133.57 | 1132.46 |
20 | δ= 6.63(8H, m), 6.79~6.81(8H, m), 6.95(4H, m), 7.2(8H, m), 7.37~7.55(30H, m), 7.64~7.66(4H, m), 7.76(2H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1381.85 | 1380.52 |
21 | δ= 1.3(8H, m), 1.45(8H, m), 6.63(8H, m), 6.79~6.81(8H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.64~7.66(4H, m), 7.76(2H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1185.64 | 1184.49 |
22 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.08(2H, m), 7.2(8H, m), 7.32(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71(4H, m), 7.98~8.04(4H, m), 8.12(2H, m), 8.28(2H, m), 8.68(2H, m), 8.93(2H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
23 | δ= 6.63(8H, m), 6.81(4H, m), 6.91~6.95(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.82~7.88(4H, m), 7.98(4H, m), 8.12(6H, m), 8.93(2H, m), 9.09(4H, m) | 1069.34 | 1068.44 |
24 | δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(10H, m), 7.41~7.56(14H, m), 7.69(2H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 871.08 | 870.37 |
25 | δ= 6.63(8H, m), 6.7(2H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41~7.52(12H, m), 7.86~7.88(4H, m), 8.07(2H, m), 8.97(2H, m) | 871.08 | 870.37 |
26 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.36(2H, s), 8.61(2H, s), 8.97(2H, m) | 873.05 | 872.36 |
27 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.33(2H, s), 8.97(2H, m) | 875.03 | 874.35 |
28 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41~7.43(4H, m), 7.51~7.56(10H, m), 7.98(2H, m), 8.12(2H, m), 8.32(2H, m), 8.68(2H, m), 8.82(2H, m), 9.09(2H, m) | 971.19 | 970.40 |
29 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.33(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86~7.9(4H, m), 8.07(2H, m), 8.38(2H, m), 8.71(2H, m), 8.88(2H, m), 8.97(2H, m) | 971.19 | 970.40 |
30 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.12(2H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.72(2H, m), 7.83~7.86(4H, m), 8.07(2H, m), 8.25(2H, m), 8.5(2H, m), 8.97(4H, m) | 1073.29 | 1072.43 |
31 | δ= 6.63(8H, m), 6.8~6.81(6H, m), 7.2(10H, m), 7.28(2H, m), 7.41(2H, m), 7.51~7.58(12H, m), 7.86(2H, m), 8.01(2H, m), 8.07(2H, m), 8.38(2H, m), 8.83(2H, m), 8.97(2H, m) | 1073.29 | 1072.43 |
32 | δ= 6.3(2H, m), 6.63(8H, m), 6.81(4H, m), 6.9~6.99(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 881.16 | 880.29 |
33 | δ= 6.54(2H, m), 6.63(8H, m), 6.81(4H, m), 6.95~7(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 849.02 | 848.34 |
34 | δ= 6.29(8H, m), 6.59(2H, s), 6.81~6.85(8H, m), 7.14(2H, s), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 974.95 | 976.18 |
35 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 885.11 | 884.28 |
36 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 852.98 | 852.32 |
37 | δ= 5.67(2H, m), 6.29(8H, m), 6.79~6.81(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) | 978.90 | 980.16 |
38 | δ= 6.63(8H, m), 6.81(4H, m), 6.88(2H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.59(2H, m), 7.98(2H, m), 8.12(2H, m), 8.74(4H, m), 9.09(2H, m) | 973.17 | 972.39 |
39 | δ= 1.72(12H, s), 3.2(6H, s), 5.66(2H, m), 5.87(2H, m), 6.45(2H, m), 6.63(8H, m), 6.81~6.83(6H, m), 6.95(4H, m), 7.07~7.08(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1159.50 | 1158.56 |
40 | δ= 3.2(6H, s), 5.7(2H, m), 5.91(2H, m), 6.49(2H, m), 6.63~6.67(10H, m), 6.81(4H, m), 6.92~6.95(6H, m), 7.13(2H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1107.34 | 1106.46 |
41 | δ= 3.2(6H, s), 5.74(2H, m), 5.95(2H, m), 6.53(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95~6.97(6H, m), 7.2~7.22(10H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1233.26 | 1234.30 |
42 | δ= 3.2(6H, s), 5.88(2H, m), 6.47(2H, m), 6.63(8H, m), 6.81~6.84(6H, m), 6.91~6.95(8H, m), 7.16~7.2(10H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1139.47 | 1138.41 |
43 | δ= 2.88(8H, m), 3.2(6H, s), 5.69(2H, m), 5.9(2H, m), 6.48(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95(4H, m), 7.07~7.1(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1131.45 | 1130.53 |
44 | δ= 3.2(6H, s), 5.74(2H, m), 5.95(2H, m), 6.53(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95~7.03(10H, m), 7.2(8H, m), 7.28(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1127.42 | 1126.50 |
45 | δ= 3.2(6H, s), 5.8(2H, m), 6.01(2H, m), 6.59~6.63(10H, m), 6.81(4H, m), 6.88(2H, m), 6.95(4H, m), 7.2(8H, m), 7.32(2H, m), 7.41~7.57(16H, m), 7.85(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1227.54 | 1226.53 |
46 | δ= 1.16(8H, m), 1.48(4H, m), 1.58(8H, m), 2.57(2H, m), 6.6(4H, m), 6.77(2H, m), 6.95(4H, m), 7.23(4H, m), 7.33(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 881.20 | 880.48 |
47 | δ= 1.16(16H, m), 1.48(8H, m), 1.58(16H, m), 2.57(4H, m), 6.76(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 893.29 | 892.57 |
48 | δ= 1.76(40H, m), 1.87(8H, m), 2.1(8H, m), 2.89(4H, m), 6.76(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1101.59 | 1100.69 |
49 | δ= 6.63(4H, m), 6.95(4H, m), 7.36~7.41(6H, m), 7.49~7.52(16H, m), 7.74~7.77(12H, m), 7.84~7.88(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
50 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.36~7.41(4H, m), 7.49~7.52(12H, m), 7.74~7.77(8H, m), 7.84~7.88(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 969.22 | 968.41 |
51 | δ= 6.63(4H, m), 6.95~6.98(8H, m), 7.38~7.41(6H, m), 7.51~7.57(20H, m), 7.77(4H, m), 7.98~8.12(12H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
52 | δ= 6.63(8H, m), 6.81(2H, m), 6.95~6.98(6H, m), 7.2(4H, m), 7.38~7.41(4H, m), 7.51~7.57(14H, m), 7.77(4H, m), 7.98~8.12(8H, m), 9.09(2H, m) | 969.22 | 968.41 |
53 | δ= 6.63(4H, m), 6.69(8H, m), 6.95(4H, m), 7.41(6H, m), 7.51~7.54(32H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1173.48 | 1172.51 |
54 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.38~7.41(10H, m), 7.51~7.52(8H, m), 7.77~7.8(6H, m), 7.88~7.9(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
55 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.08(2H, m), 7.2(4H, m), 7.32(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(12H, m), 7.98(2H, m), 8.12(4H, m), 8.68(2H, m), 8.93(2H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
56 | δ= 6.63(4H, m), 6.95(4H, m), 7.08(4H, m), 7.32(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(20H, m), 7.98(2H, m), 8.12(6H, m), 8.68(4H, m), 8.93(4H, m), 9.09(2H, m) | 1269.57 | 1268.51 |
57 | δ= 6.63(8H, m), 6.81(2H, m), 6.91~6.95(6H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77~7.88(12H, m), 7.98(2H, m), 8.12(6H, m), 8.93(4H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
58 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.02(2H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(14H, m), 7.98(2H, m), 8.12~8.13(6H, m), 8.93(2H, m), 9.09(2H, m) | 1069.34 | 1068.44 |
59 | δ= 6.63(8H, m), 6.81(2H, m), 6.91~6.95(6H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(16H, m), 7.98(2H, m), 8.12(6H, m), 9.09(2H, m) | 1117.38 | 1116.44 |
60 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.82(14H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) | 1117.38 | 1116.44 |
61 | δ= 6.63(4H, m), 6.95(4H, m), 7.02(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77~7.88(24H, m), 7.98(2H, m), 8.12~8.13(14H, m), 8.93(8H, m), 9.09(2H, m) | 1469.80 | 1468.57 |
62 | δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.57(10H, m), 7.73~7.78(8H, m), 7.88(2H, m), 7.98(2H, m), 8.1~8.12(6H, m), 8.42(4H, m), 9.09(2H, m) | 1117.38 | 1116.44 |
63 | δ= 6.63(4H, m), 6.95(4H, m), 7.12(2H, m), 7.41(2H, m), 7.51~7.58(16H, m), 7.72~7.77(6H, m), 7.83(2H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.22~8.25(4H, m), 8.38(4H, m), 8.83(4H, m), 9.09(2H, m) | 1277.47 | 1276.47 |
64 | δ= 0.9(24H, m), 1.91(16H, m), 6.58~6.63(8H, m), 6.75(4H, m), 6.95(4H, m), 7.28(4H, m), 7.38~7.41(6H, m), 7.51~7.55(12H, m), 7.62(4H, m), 7.77(4H, m), 7.87(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1445.95 | 1444.76 |
65 | δ= 0.9(12H, m), 1.91(8H, m), 6.58~6.63(10H, m), 6.75~6.81(4H, m), 6.95(4H, m), 7.2(4H, m), 7.28(2H, m), 7.38~7.41(4H, m), 7.51~7.55(10H, m), 7.62(2H, m), 7.77(4H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1157.53 | 1156.57 |
66 | δ= 0.9(12H, m), 1.91(8H, m), 6.47(2H, s), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2~7.24(6H, m), 7.41~7.52(16H, m), 7.61(2H, m), 7.77(4H, m), 7.98(2H, m), 8.08~8.12(6H, m), 8.46(2H, m), 9.09(2H, m) | 1257.64 | 1256.60 |
67 | δ= 0.9(24H, m), 1.91~1.93(16H, m), 6.63(4H, m), 6.77(3H, m), 6.95(4H, m), 7.18(3H, m), 7.24~7.29(5H, m), 7.41~7.52(15H, m), 7.61(4H, m), 7.71~7.77(11H, m), 7.85(1H, m), 7.98~8.02(5H, m), 8.09~8.16(7H, m), 9.09(2H, m) | 1646.19 | 1644.82 |
68 | δ= 6.58~6.63(10H, m), 6.75~6.81(4H, m), 6.95(4H, m), 7.11(8H, m), 7.2~7.41(22H, m), 7.51~7.55(10H, m), 7.62(2H, m), 7.77(4H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1349.70 | 1348.57 |
69 | δ= 6.39(2H, m), 6.55(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.16~7.2(8H, m), 7.28(4H, m), 7.35~7.41(8H, m), 7.5~7.55(14H, m), 7.75~7.77(6H, m), 7.87(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1345.67 | 1344.54 |
70 | δ= 5.19(4H, s), 6.39(2H, m), 6.51(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.03~7.06(10H, m), 7.15~7.2(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1221.53 | 1220.51 |
71 | δ= 5.19(4H, s), 6.39(2H, m), 6.51(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.03~7.06(10H, m), 7.15~7.2(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1221.53 | 1220.51 |
72 | δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.55(12H, m), 7.77(4H, m), 7.98(2H, m), 8.07~8.12(6H, m), 9.09(2H, m) | 873.05 | 872.36 |
73 | δ= 6.62~6.63(6H, m), 6.95(4H, m), 7.19(2H, m), 7.37~7.41(8H, m), 7.51~7.57(10H, m), 7.69~7.8(10H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.22(2H, m), 8.75(2H, m), 9.09(2H, m) | 1073.29 | 1072.43 |
74 | δ= 6.95(4H, m), 7.25~7.33(6H, m), 7.41(2H, m), 7.5~7.52(14H, m), 7.62~7.63(6H, m), 7.94~7.98(4H, m), 8.12(4H, m), 8.55(2H, m), 9.09(2H, m) | 865.07 | 864.35 |
75 | δ= 1.72(12H, s), 6.55(4H, m), 6.63(4H, m), 6.73(4H, m), 6.95(4H, m), 7.02~7.05(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 949.23 | 948.44 |
76 | δ= 6.38(8H, m), 6.56(8H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1047.29 | 1046.43 |
77 | δ= 6.63(4H, m), 6.95~6.97(8H, m), 7.16~7.21(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 929.20 | 928.29 |
78 | δ= 6.59~6.63(8H, m), 6.77(4H, m), 6.89~6.95(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 897.07 | 896.34 |
79 | δ= 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7.3(4H, m), 7.37~7.55(30H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1229.66 | 1228.46 |
80 | δ= 1.3(8H, m), 1.45(8H, m), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7.3(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1033.45 | 1032.43 |
81 | δ= 2.71(8H, s), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.11~7.14(8H, m), 7.21(4H, m), 7.3(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1129.54 | 1128.43 |
82 | δ= 2.88(8H, m), 6.58~6.63(8H, m), 6.76(4H, m), 6.95(4H, m), 7.02~7.04(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 921.18 | 920.41 |
83 | δ= 6.63(8H, m), 6.81(4H, m), 6.95~7.05(12H, m), 7.25(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 917.14 | 916.38 |
84 | δ= 6.63(4H, m), 6.69(4H, m), 6.87(4H, m), 6.95(4H, m), 7.16(4H, m), 7.41~7.54(18H, m), 7.77(4H, m), 7.85(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1017.26 | 1016.41 |
85 | δ= 1.53(12H, m), 3.63(4H, m), 5.99~6.05(8H, m), 6.95(4H, m), 7.22~7.33(16H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1077.40 | 1076.51 |
86 | δ= 6.63(4H, m), 6.95(4H, m), 7.14(4H, m), 7.32~7.41(10H, m), 7.51~7.52(8H, m), 7.66(4H, m), 7.77(4H, m), 7.89(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1029.18 | 1028.36 |
87 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.14(2H, m), 7.2(4H, m), 7.32~7.41(6H, m), 7.51~7.52(8H, m), 7.66(2H, m), 7.77(4H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 949.14 | 948.37 |
88 | δ= 6.34(4H, m), 6.63(4H, m), 6.95(4H, m), 7.41(2H, m), 7.5~7.52(16H, m), 7.77~7.79(8H, m), 7.98(6H, m), 8.12(2H, m), 9.09(2H, m) | 1093.45 | 1092.27 |
89 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.53(12H, m), 7.77(4H, m), 7.98~8.01(4H, m), 8.12(2H, m), 8.18(2H, m), 9.09(2H, m) | 983.25 | 982.32 |
90 | δ= 6.63(4H, m), 6.95(4H, m), 7.39~7.41(10H, m), 7.51~7.52(8H, m), 7.74~7.77(12H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1033.14 | 1032.34 |
91 | δ= 1.35(36H, s), 6.55(8H, m), 6.63(4H, m), 6.95~7.01(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1093.53 | 1092.63 |
92 | δ= 0.25(36H, s), 6.61~6.63(12H, m), 6.95(4H, m), 7.15(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1157.83 | 1156.54 |
93 | δ= 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(8H, m), 7.37~7.55(70H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1902.66 | 1900.73 |
94 | δ= 6.61~6.63(12H, m), 6.95~6.99(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 941.06 | 940.34 |
95 | δ= 6.56(8H, m), 6.63(4H, m), 6.95(4H, m), 7.37~7.41(10H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1141.09 | 1140.33 |
96 | δ= 6.63(4H, m), 6.81(8H, m), 6.95(4H, m), 7.39~7.41(10H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 969.14 | 968.36 |
97 | δ= 3.83(12H, s), 6.52(8H, m), 6.63(4H, m), 6.74(8H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 989.20 | 988.42 |
98 | δ= 6.63(8H, m), 6.69(4H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(4H, m), 7.51~7.54(20H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 1021.29 | 1020.44 |
99 | δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.55(12H, m), 7.77(4H, m), 7.98(2H, m), 8.07~8.12(6H, m), 9.09(2H, m) | 873.05 | 872.36 |
100 | δ= 6.63(4H, m), 6.95(4H, m), 7.27(4H, m), 7.36~7.41(6H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98~8.12(12H, m), 9.09(2H, m) | 873.05 | 872.36 |
101 | δ= 6.63(8H, m), 6.7(2H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.46(2H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.86~7.92(6H, m), 8(4H, m), 8.07(2H, m), 8.97(2H, m) | 971.19 | 970.40 |
102 | δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 879.16 | 878.44 |
103 | δ= 3.05(4H, m), 4.14(4H, m), 6.55~6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05~7.07(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 768.98 | 768.35 |
104 | δ= 1.25(6H, m), 1.81(4H, m), 2.79~2.8(6H, m), 6.55~6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05~7.07(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) | 825.09 | 824.41 |
105 | δ= 6.52(2H, m), 6.87(2H, m), 6.95(4H, m), 7.33(2H, m), 7.41(2H, m), 7.5~7.52(12H, m), 7.6~7.62(6H, m), 7.93~7.98(6H, m), 8.12(2H, m), 9.09(2H, m) | 764.95 | 764.32 |
106 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.56(4H, m), 7.64(4H, m), 7.77~7.88(8H, m), 8.12(2H, m), 8.93(2H, m) | 869.10 | 858.38 |
107 | δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(10H, m), 7.44~7.45(6H, m), 7.56~7.59(6H, m), 7.69(2H, m), 7.82~7.88(4H, m), 8.12(2H, m), 8.93(2H, m) | 871.08 | 870.37 |
108 | δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(8H, m), 7.45~7.49(4H, m), 7.69(2H, m), 7.81~7.88(10H, m), 8.12(2H, m), 8.85(2H, m), 8.93(2H, m) | 873.05 | 872.36 |
109 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.64(4H, m), 7.77(4H, m), 8.1(2H, m), 8.34(2H, m), 8.99(2H, m) | 1021.29 | 1020.44 |
110 | δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.64(4H, m), 7.77(4H, m), 8.04(2H, m), 8.18(2H, m), 9.15(2H, m) | 1021.29 | 1020.44 |
111 | δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.55~7.56(8H, m), 7.64(4H, m), 7.77~7.88(8H, m), 8.07~8.12(6H, m), 8.93(2H, m) | 873.05 | 872.36 |
[Examples 1-11] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use. Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
Then, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. DNA (Examples 1 to 3) was placed in a cell of the vacuum vapor deposition apparatus as a host, and the compound according to the present invention was placed in another cell as a dopant. The two materials were vapor-deposited at a rate of 100:3 to form an electroluminescent layer having a thickness of 30 nm on the hole transport layer.
Then, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer, and lithium quinolate (Liq) was vapor-deposited with a thickness of 1 to 2 nm as an electron injection layer. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED had been purified by vacuum sublimation at 10-6torr.
Luminescence efficiency of the OLED devices containing the organic electroluminescent compound according to the present invention manufactured in Examples 1 to 3 was measured at 1,000 cd/m2. The result is given in Table 2.
Table 2
No. | EL material 1 | EL material 2 | Luminescence efficiency (cd/A) | Color | |
Example | 1 | DNA | Compound 88 | 3.4 | Deep blue |
2 | DNA | Compound 94 | 3.9 | Deep blue | |
3 | DNA | Compound 102 | 3.5 | Deep blue |
As seen from Table 2, the organic electroluminescent compounds of the present invention provide deep blue color. That, when a blue color having the level of about CIE y = 0.1 is required for realizing the color close to the NTSC standard in the organic electroluminescent display, the organic electroluminescent compounds of the present invention may be useful. Since phenanthrene derivatives have high glass transition temperature, superior thermal stability is acquired. As described above, the organic electroluminescent compound of the present invention is used as a blue light-emitting material having high purity.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
Claims (10)
- An organic electroluminescent compound represented by Chemical Formula 1:[Chemical Formula 1]whereinR1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl] or , except for the case where two of R1, R4, R7 and R10 are hydrogen;R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];L1 represents a single bond, (C6-C30)arylene or (C2-C30)heteroarylene;R11 and R12 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], 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 alicyclic ring or a mono- or polycyclic aromatic ring;the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10 and R31 through R35; the arylene or heteroarylene of L1 and L2; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R11 and R12; and the fused ring formed by link between R11 and R12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; andm represents an integer 0, 1 or 2.
- The organic electroluminescent compound according to claim 1, which is represented by Chemical Formula 2 or 3:[Chemical Formula 2][Chemical Formula 3]whereinL21 and L22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;R41 through R44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], 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 alicyclic ring or a mono- or polycyclic aromatic ring;R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10; and the arylene or heteroarylene of L11, L12, L21 and L22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; andm represents an integer 0, 1 or 2.
- The organic electroluminescent compound according to claim 2, wherein L11 and L12 independently represent phenylene, naphthalene, biphenylene, phenanthrylene, pyrazinylene, triazinylene, quinolylene, phenanthrolinylene, thienylene, furylene, selenophenylene, thiadiazolylene, oxadiazolylene, selenadiazolylene or quinoxalinylene, or a divalent group selected from the following structures:R31 through R35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring;L21 and L22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;R2, R3, R5, R6, R8 and R9 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl;R41 through R44 independently represent cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, triazinyl, pyrimidyl or ;R1, R4, R7 and R10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; andL11, L12, L21, L22, R1 through R10 and R41 through R44 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl.
- The organic electroluminescent compound according to claim 3, wherein and are independently selected from the following structures:whereinR31 through R35 independently represent (C1-C30)alkyl or (C6-C30)aryl, 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 alicyclic ring or a mono- or polycyclic aromatic ring.
- An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 4.
- The organic electroluminescent device according to claim 5, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) according to any of claims 1 to 4 and one or more host(s) selected from the compounds represented by Chemical Formula 4 or 5:[Chemical Formula 4](Ar101)a-L101-(Ar102)b[Chemical Formula 5](Ar103)c-L102-(Ar104)dwhereinL101 represents (C6-C30)arylene or (C4-C30)heteroarylene;L102 represents anthracenylene;Ar101 through Ar104 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar101 through Ar104 is further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl; anda, b, c and d independently represent an integer from 0 to 4.
- The organic electroluminescent device according to claim 6, wherein the organic layer further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds.
- The organic electroluminescent device according to claim 6, wherein the organic layer further comprises one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
- The organic electroluminescent device according to claim 6, the organic layer comprises an electroluminescent layer and a charge generating layer.
- The organic electroluminescent device according to claim 6, which is a white light-emitting organic electroluminescent device, wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
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US10361373B2 (en) | 2015-08-28 | 2019-07-23 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light emitting device comprising the same |
US20180294419A1 (en) * | 2017-04-06 | 2018-10-11 | Samsung Display Co., Ltd. | Light emission material and organic electroluminescence device including the same |
WO2020220611A1 (en) * | 2019-04-29 | 2020-11-05 | 武汉华星光电半导体显示技术有限公司 | Thermally activated delayed fluorescent molecular material and synthesis method therefor, and organic electroluminescent device |
US11613530B2 (en) | 2019-04-29 | 2023-03-28 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Thermally activated delayed fluorescent molecular material, method for synthesizing the same, and organic electroluminescent device |
CN112341486A (en) * | 2019-11-01 | 2021-02-09 | 广东聚华印刷显示技术有限公司 | Silicon-containing compound, silicon-containing polymer, application of silicon-containing polymer and organic light-emitting diode device |
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KR20110119206A (en) | 2011-11-02 |
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