WO2010114253A2 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
- Publication number
- WO2010114253A2 WO2010114253A2 PCT/KR2010/001813 KR2010001813W WO2010114253A2 WO 2010114253 A2 WO2010114253 A2 WO 2010114253A2 KR 2010001813 W KR2010001813 W KR 2010001813W WO 2010114253 A2 WO2010114253 A2 WO 2010114253A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituent
- organic electroluminescent
- alkyl
- fused
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- 125000001424 substituent group Chemical group 0.000 claims description 158
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 239000010410 layer Substances 0.000 claims description 49
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 21
- -1 cyano, carbazolyl Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000005571 adamantylene group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 150000002739 metals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 238000005401 electroluminescence Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 239000011369 resultant mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BQMNNWIYAUNZBO-UHFFFAOYSA-N 2-chloro-4a,9a-dihydroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3C=C(Cl)C=CC3C(=O)C2=C1 BQMNNWIYAUNZBO-UHFFFAOYSA-N 0.000 description 1
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- 0 CC1(C)C(C=CCC2)=C2c(c2c3cccc2)c1cc3-c1c(cccc2)c2c(*)c2ccccc12 Chemical compound CC1(C)C(C=CCC2)=C2c(c2c3cccc2)c1cc3-c1c(cccc2)c2c(*)c2ccccc12 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 229910003953 H3PO2 Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 125000005584 chrysenylene group Chemical group 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
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- SWGQITQOBPXVRC-UHFFFAOYSA-N methyl 2-bromobenzoate Chemical compound COC(=O)C1=CC=CC=C1Br SWGQITQOBPXVRC-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Definitions
- the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices employing the same. Specifically, it relates to novel anthracene derivatives having electroluminescent properties, and organic electroluminescent devices employing the same as electroluminescent material.
- electroluminescence (EL) devices being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate.
- Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
- An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light.
- a device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused for full colored display devices for next generation.
- electroluminescent material The most important factor to determine luminous efficiency, lifetime or the like in an organic EL device is electroluminescent material.
- electroluminescent materials include that the material should have high luminescent quantum yield in solid state and high mobility of electrons and holes, is not easily decomposed during vapor-deposition in vacuum, and forms uniform and stable thin film.
- An organic EL device is composed of anode/HIL/HTL/EML/ETL/EIL/cathode.
- the color of the light emitted (blue, green, red) from the organic electroluminescent device can be realized depending on how the electroluminescent layer (EML) is formed.
- the electroluminescent materials are classified into host materials and dopant materials from the aspect of their functions. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel.
- a green fluorescent material As a green fluorescent material, a system wherein a coumarine derivative (Compound d, C545T), a quinacridone derivative (Compound e), DPT (Compound f) or the like is doped to Alq (a host), as a dopant, in a concentration from several % to not more than 20 % has been developed and widely used.
- the conventional electroluminescent materials suffer from significant problem in view of lifetime with noticeable reduction of initial efficiency, though they show good performance in view of initial luminous efficiency at the level of practical use.
- the materials have limitations to be employed for a high performance panel of larger screen.
- the object of the invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinate, as compared to conventional host materials.
- Another object of the invention is to provide organic electroluminescent devices of high efficiency and long life by employing those organic electroluminescent compounds as electroluminescent material.
- novel organic electroluminescent compounds were prepared according to the invention.
- Those compounds can be employed as electroluminescent material for an organic electroluminescent device, particularly as electroluminescent host, preferably green host.
- the compounds according to the invention provides organic electroluminescent devices with enhanced efficiency, lowered operation voltage and improved stability.
- the present invention provides organic electroluminescent compounds represented by Chemical Formula (1):
- L 1 and L 2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), substituted or unsubstituted 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s), (C3-C30)cycloalkylene with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkylene fused with one or more aromatic ring(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(C1-C30)alkylene with or without substituent(s
- R 1 through R 4 and Ar 1 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30) aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), substituted or unsubstituted 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkyl fused with one or more aromatic ring(s), adamantyl with or without substituent(s), (C7-C30)bicy
- n an integer 1 or 2.
- alkyl and other substituents containing ‘alkyl’ moiety described herein include both linear and branched species.
- aryl represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
- An aryl group may be a monocyclic or a fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through single bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto.
- the naphthyl may be 1-naphthyl or 2-naphthyl
- the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl
- the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
- the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
- the structures having one or more heteroaryl group(s) bonded through a single bond are also included.
- the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
- Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazo
- the alkyl groups in ‘C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C1-C30)alkyloxycarbonyl, (C1-C30)alkylcarbonyl, (C1-C30)alkyloxycarbonyloxy, (C1-C30)alkylcarbonyloxy’ described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10.
- the aryl groups in ‘(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy’ may have restricted carbon number from 6 to 20, or from 6 to 12.
- the heteroaryl groups in ‘(C3-C30)heteroaryl’ may have restricted carbon number from 4 to 20, or from 4 to 12.
- the cycloalkyl groups in ‘(C3-C30)cycloalkyl’ may have restricted carbon number from 3 to 20, or from 3 to 7.
- the alkenyl or alkynyl of ‘(C2-C30)alkenyl or alkynyl’ may have restricted carbon number from 2 to 20, or from 2 to 10.
- L 1 and L 2 are independently selected from a chemical bond; arylene groups such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylenylene, fluoranthenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene and perylenylene; and heteroarylene groups such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, quinolinylene, quinoxalinylene, phenanthrolinylene, but they are not restricted thereto. Those groups may be further substituted as described for Chemical Formula (1).
- R 51 through R 58 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.
- organic electroluminescent compounds according to the present invention can be more specifically exemplified by the following compounds, but they are not restricted thereto.
- R 1 through R 4 , L 1 , L 2 and Ar 1 are defined as for Chemical Formula (1).
- the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula (1).
- the organic electroluminescent compound is employed as host material of the electroluminescent layer.
- the organic electroluminescent device according to the present invention is characterized in that the organic layer comprises an electroluminescent layer containing one or more organic electroluminescent compound(s) represented by Chemical Formula (1), as well as one or more dopant(s).
- the dopant to be applied to an organic electroluminescent device according to the invention is not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (2) or (3):
- L represents (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s);
- the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer consisting of two or more layers laminated.
- a mixture of host-dopant is used according to the constitution of the present invention, noticeable improvement in luminous efficiency due to the inventive electroluminescent host could be confirmed. This can be achieved by the doping concentration of 0.5 to 10% by weight.
- the host according to the present invention exhibits higher hole and electron conductivity, and excellent stability of material as compared to other conventional host materials, and provides improved device life as well as luminous efficiency.
- the dopant compounds represented by Chemical Formula (3) can be exemplified by those described in Korean Patent Application No. 10-2009-0023442. More preferably they are selected from the following structures, but not restricted thereto.
- the organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1).
- the arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d-transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the electroluminescent compound represented by Chemical Formula (1).
- the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
- the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1), to form an organic electroluminescent device emitting white light.
- the compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
- an organic electroluminescent device it is preferable to arrange one or more layer(s) (here-in-below, referred to as the ‘surface layer’) selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes.
- the surface layer selected from chalcogenide layers, metal halide layers and metal oxide layers.
- a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the EL medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer.
- Examples of metal halides preferably include LiF, MgF 2 , CaF 2 , fluorides of rare earth metal or the like.
- Examples of metal oxides preferably include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.
- an organic electroluminescent device it is also preferable to arrange, on at least one surface of the pair of electrodes thus manufactured, a mixed region of electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL medium are facilitated.
- Preferable oxidative dopants include various Lewis acids and acceptor compounds.
- Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
- the organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life property of the material, so that OLED’s having very good operation life can be manufactured therefrom.
- OLED devices were manufactured by using the electroluminescent material according to the invention.
- a transparent electrode ITO thin film (15 ⁇ / ⁇ ) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
- an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4′4′′-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
- 2-TNATA 4,4′4′′-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
- NPB N,N′-bis( ⁇ -naphthyl)-N,N′-diphenyl-4,4′-diamine
- an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (1) according to the present invention as host, and Compound (A) was charged to another cell as dopant. Two substances were evaporated at different rates to provide doping at a concentration of 2 to 5% by weight on the basis of the host. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
- Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10 -6 torr.
- an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
- an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
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CN2010800250539A CN102449110A (zh) | 2009-03-31 | 2010-03-24 | 新颖的有机电致发光化合物和使用该化合物的有机电致发光设备 |
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JP2012089725A (ja) * | 2010-10-21 | 2012-05-10 | Konica Minolta Holdings Inc | 有機光電変換素子および太陽電池 |
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- 2010-03-24 WO PCT/KR2010/001813 patent/WO2010114253A2/en active Application Filing
- 2010-03-24 CN CN2010800250539A patent/CN102449110A/zh active Pending
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CN102449110A (zh) | 2012-05-09 |
TW201105776A (en) | 2011-02-16 |
WO2010114253A3 (en) | 2010-12-23 |
JP5781499B2 (ja) | 2015-09-24 |
KR20100109293A (ko) | 2010-10-08 |
JP2012522041A (ja) | 2012-09-20 |
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