TW201130805A - 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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- TW201130805A TW201130805A TW099143434A TW99143434A TW201130805A TW 201130805 A TW201130805 A TW 201130805A TW 099143434 A TW099143434 A TW 099143434A TW 99143434 A TW99143434 A TW 99143434A TW 201130805 A TW201130805 A TW 201130805A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 125000001424 substituent group Chemical group 0.000 claims description 101
- -1 RTrSi- Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 230000005684 electric field Effects 0.000 claims description 45
- 239000010410 layer Substances 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 21
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- 239000002019 doping agent Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000004020 luminiscence type Methods 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
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- 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 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
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- 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 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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- 239000003446 ligand Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
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- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000000034 method Methods 0.000 description 5
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- 239000007787 solid Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
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- 229910044991 metal oxide Inorganic materials 0.000 description 3
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
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- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09B57/00—Other synthetic dyes of known constitution
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
Description
201130805 9 六、發明說明： .【發明所屬之技術領域】 本發明係關於新穎有機電場發光（electr〇luminescent) 化合物，以及使用該化合物之有機電場發光裝置，更具體 地，本發明係關於作為電場發光材料之新穎有機電場發光201130805 9 VI. TECHNOLOGICAL DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to novel organic electroluminescent (electr〇 luminescent) compounds, and organic electric field illuminating devices using the same, and more particularly to the present invention as an electric field Novel organic electric field luminescence of luminescent materials
化合物，以及使用該化合物作為主體（h〇st)之有機電場發 光裝置。 X 【先前技術】 於顯示器裝置中，電場發光（EL)裝置的優點在於其作 為自發光顯示器裝置係提供寬視角、高對比度及高反應速 率。1987年，伊斯門-柯達（Eastman Kodak)首先發展出使 用低;7子量¾香無一胺及銘之錯合物作為形成電場發光層 之物質的有機EL裝置[如p/.户力％. 51，913，1987^。 於有機EL裝置中，當將電荷施加至形成於電子注入 電極（陰極）與電洞注入電極（陽極）之間的有機層時，電子 ’、電/同係配對並產生激子（e χ e丨t Q n )。藉由在激子不活化之 狀〜、使用電場發光（磷光或螢光）而發射光。該有機此裝置 =約μ伏特（v)之電壓及約100至1〇,〇〇〇燭光（cd)/平方 a尺（m )之南免度發射偏極化之光。該有機EL裝置的特徵 為藉由簡單選擇螢光材料而發射藍色至紅色光譜範圍之 ^有機EL裝置之優勢在於其能在可撓性透明基板（例如 塑膠）上形成，相較於電衆顯示器面板或無機EL顯示器， 其可以相對較低電壓（1〇v或更低）操作，消耗較少之功 率’且提供優異之顏色。 95084 3 201130805 於有機EL裝置中，決定其包括發光效率 (luminescence)及操作壽命之效能的最重要因素為電場發 光材料。該電場發光材料之若干需求包括：在固態中之高 電場發光量子產率、高電子及電洞遷移率、於真空沉積過 程中對分解之抗性、形成均勻膜之能力及安定性。 有機電場發光材料-般係分為高分子材料及低分子 材料。就分子結構層面，低分子材料包括金屬錯合物及不 含金屬之完全有機電場發光材料。此等電場發光材料包括 螯合錯合物例如參（8-羥基喹啉基）鋁錯合物、香豆素衍生 物、四苯基丁二烯衍生物、雙（苯乙烯基伸芳基）（Ms (styrylarylene))衍生物及噚二唑衍生物。據悉，可由彼 等材料獲得自藍色至紅色之可見光區域的發光。 三種電場發光材料（紅色、綠色及藍色，後文中有稱 為紅光、綠光及藍光之情形）係用於實現全彩有機發光二極 體（0LED)顯示器。重點是開發具有高效率及長壽命之紅 色綠色及藍色電場發光材料，以提升有機電場發光（EL) 裝置的總體特性。於功能層面，EL材料係分為主體材料及 捧雜劑材料。眾所周知，可使用藉由將摻雜劑摻雜至主體 中所製備之EL層來製造具有最優異EL性質的裝置結構。 近年來，開發具有高效能及長壽命之有機£ 解決的課題。考量恤大型尺寸。LED面板對 要求，開發具遠較於傳統EL材料為佳之既性質的材料尤 其急迫。自此觀點看來，開發主體材料係待解決之最重要 課題之一。主體材料（作為固態之溶劑及能量傳遞者）之所 95084 4 201130805 彭 欲性質係高純度及適宜之分子量，以能夠於真空中氣相沉 -積。此外，玻璃轉化溫度及熱分解溫度應足夠高，以確保 熱安定性。再者，該主體材料應具有高電化學安定性，以 提供長壽命。需要易於形成非晶質薄膜，且對其他相鄰材 料具咼度黏著性但不會產生層間遷移。 當藉由摻雜技術製造有機el裝置時，在激態中自主 體分子向摻雜劑之能量轉移不會達到100%，且主體材料及 摻雜劑都會發光。具體而言，於發射紅光之裝置之例子中， 相較於摻雜劑材料，由於該主體材料在具有較大之可見性 之波長範圍内發光，故該主體材料之暗光發射（dull Hght emission)使得色純度降低。若實際實施該技術 ’則需要增 加發光壽命以及改善耐久性。 曰目别’ CBP係最廣為人知之碟光材料的主體材料。已 提出使用包含BCP、BAlq等之電洞阻擔層的高效率〇LED。 先舞（Pioneer^日本）等公司也已提出使用腿卩衍生物作 為主體之高效能0LED。A compound, and an organic electric field emitting device using the compound as a host (h〇st). X [Prior Art] In an display device, an electric field illumination (EL) device has an advantage in that it provides a wide viewing angle, a high contrast ratio, and a high reaction rate as a self-luminous display device system. In 1987, Eastman Kodak first developed an organic EL device using a low-volume, 7-substance, 3⁄4 fragrant, no amine, and a complex of the compound as a substance for forming an electroluminescent layer [eg, p/. %. 51,913,1987^. In an organic EL device, when an electric charge is applied to an organic layer formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), electrons, electricity/same pairs are paired and excitons are generated (e χ e丨t Q n ). Light is emitted by the use of an electric field (phosphorescence or fluorescence) in the case where excitons are not activated. The organic device = a voltage of about μV (v) and about 100 to 1 〇, a candlelight (cd) / square a (m) south of the degree of emission of polarized light. The organic EL device is characterized in that an organic EL device that emits a blue to red spectral range by simply selecting a fluorescent material is advantageous in that it can be formed on a flexible transparent substrate (for example, plastic) as compared with the electric group. A display panel or inorganic EL display that can operate at relatively low voltages (1 〇 v or less) consumes less power 'and provides excellent color. 95084 3 201130805 In organic EL devices, the most important factor in determining the efficacy of luminescence and operational lifetime is the electric field luminescent material. Several requirements for the electroluminescent material include: high electric field luminescence quantum yield in the solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form a uniform film, and stability. Organic electric field luminescent materials are generally classified into polymer materials and low molecular materials. At the molecular structure level, low molecular materials include metal complexes and fully organic electroluminescent materials that do not contain metals. Such electroluminescent materials include chelating complexes such as quinone (8-hydroxyquinolinyl) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styryl extended aryl) ( Ms (styrylarylene) derivatives and oxadiazole derivatives. It is reported that the light from the blue to red visible light region can be obtained from these materials. Three electric field luminescent materials (red, green, and blue, hereinafter referred to as red, green, and blue) are used to implement full color organic light emitting diode (OLED) displays. The focus is on the development of red, green and blue electric field luminescent materials with high efficiency and long life to enhance the overall characteristics of organic electroluminescent (EL) devices. At the functional level, the EL material is divided into a host material and a dopant material. It is known that a device structure having the most excellent EL properties can be manufactured by using an EL layer prepared by doping a dopant into a host. In recent years, the development of high-performance and long-life organic solutions has been developed. Consider the large size of the shirt. LED panel requirements are particularly urgent to develop materials that are far superior to traditional EL materials. From this point of view, the development of the main material is one of the most important issues to be solved. The main material (as a solid solvent and energy transferr) 95084 4 201130805 The desired nature is high purity and suitable molecular weight to enable gas phase deposition in a vacuum. In addition, the glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability. Furthermore, the host material should have high electrochemical stability to provide long life. It is desirable to form an amorphous film easily and to have a degree of adhesion to other adjacent materials without interlaminar migration. When an organic EL device is fabricated by a doping technique, the energy transfer of the autonomous molecule to the dopant in the excimer does not reach 100%, and both the host material and the dopant emit light. Specifically, in the example of the device for emitting red light, the dark light emission of the host material (dull Hght) is compared to the dopant material because the host material emits light in a wavelength range having greater visibility. Emission) causes a decrease in color purity. If the technology is actually implemented, it is necessary to increase the luminescence lifetime and improve the durability.曰目别' CBP is the most widely known material for disc materials. High efficiency 〇LEDs using a hole-resisting layer including BCP, BAlq, etc. have been proposed. Companies such as Pioneer (Japan) have also proposed high-performance OLEDs using leg scorpion derivatives as the main body.
BAIq BAIq衍生物 雖然這些材料提供良好的電場發光特性，但由於其玻 璃，化溫度低且熱安定性差，故此等材料之缺點為於真空 溫沉積製程期間可能會發生降解。由於〇LED之功率效 ;'又義為（Π/電壓）x電流效率，所以功率效率與電壓成反 95084 5 201130805 比。為了降低0LED之功率消耗，乃需要高 刀竿效率。f際 上’使用磷光材料之0LED遠比使用螢光材料者沪提供 ” 的電流效率（燭光（cd)/安培（A))。然而，當使用$ 、更子 例如BAlq、CBP等作為磷光材料之主體時，因為二料 壓，使得相較於使用螢光材料之_，其率 明（ΙπΟ/瓦（W))方面不具有顯著優勢。 革放率 此置不具有令人滿意之操作壽命。因 此而要開發更文定、更高效能之主體材料。 【發明内容】 技術問題 有二2了解決前述之問題，本發明之目的係提供具 :較見有材料良好之發光欵率及裝置操作壽命，且含有且 適宜色座標之優異骨牟的古 八 s 一 a μ 、’、、有機電場發光化合物。本發明之 另目的係提供高效率及人 係使用該有機電鄉光化^命之有㈣場發光裝置，其 技術方案 讀就合物作為電場發光材料。 本發明提供下述化學 予式1表示之新穎有機電場發光化 物之有機電場發光裝置。相較於現有主 效率及優異之有機電場發光化合物呈現良好發光 命且因此其可用於製造具有極高操作壽 … > 率而4乾較少功率的0LED裝置。 6 95084BAIq BAIq Derivatives Although these materials provide good electric field luminescence properties, due to their low glass temperature and poor thermal stability, these materials have the disadvantage of being degraded during the vacuum temperature deposition process. Because of the power efficiency of 〇LED; 'also means (Π/voltage) x current efficiency, so the power efficiency is opposite to the voltage of 95084 5 201130805. In order to reduce the power consumption of the OLED, high efficiency is required. The current efficiency of the 'LED using phosphorescent material is much higher than that of the material using fluorescent materials (candle light (cd) / ampere (A)). However, when using $, more, such as BAlq, CBP, etc. as phosphorescent materials In the main body, because of the second material pressure, it has no significant advantage in terms of ΙπΟ/W (W) compared to the use of fluorescent materials. The polishing rate does not have a satisfactory operating life. Therefore, it is necessary to develop a more effective and more efficient host material. [Disclosure] There are two technical problems to solve the aforementioned problems, and the object of the present invention is to provide a light-emitting rate and device with better materials. An ancient eight-a-μ, ',, organic electroluminescent compound containing an excellent backbone of the color coordinates, and an additional object of the present invention is to provide high efficiency and human use of the organic electro-optical There is a (four) field illuminating device, and the technical solution thereof is used as an electric field illuminating material. The present invention provides an organic electric field illuminating device of the novel organic electric field illuminating compound represented by the following formula 1 in comparison with the existing main effect. And is excellent in the organic electroluminescent compound exhibits good luminescent life and therefore it can be used to manufacture a very high operating life ... > 4 0LED rate of drying and less power 695,084.
I 201130805 化學式1I 201130805 Chemical Formula 1
其中，among them,
Ai、A2及^至Bs係獨立表示CR或N ; X 係表示化學鍵、-C(Rll)(Rl2)-、-N(Rl3)-、-S-、_〇-或-SKRhXRu)-; R、1至R6及Ru至R15係獨立表示氫、氘、鹵素、具有 或不具有取代基之（C1-C30)烷基、具有或不具有取代基之 (C6-C30)芳基、與一個或多個具有或不具有取代基之 (C3-C30)環烷基稠合之經取代或未經取代之（C6-C30)芳 基、具有或不具有取代基之（C3-C30)雜芳基、具有或不具 有取代基之5至7員雜環烷基、與一個或多個具有或不具 有取代基之芳香環稠合之5至7員雜環烷基、具有或不具 有取代基之（C3-C30)環烷基、與一個或多個具有或不具有 取代基之芳香環稠合之（C3-C30)環烷基、氰基、硝基、 NR21R22、BR23R24、PR25R26、P(=0)R27R28 [其中，R21 至 R28 係獨 立表示具有或不具有取代基之（C1-C30)烷基、具有或不具 有取代基之（C6-C30)芳基、或具有或不具有取代基之 (C3-C30)雜芳基]、R29R3〇R3iSi-[其中，R29至R31係獨立表 示具有或不具有取代基之（C1-C30)烷基、具有或不具有取 7 95084 201130805 代基之（C6-C30)芳基、或具有或不具有取代基之（C3-C30) 雜芳基]、具有或不具有取代基之（C6-C30)芳基（C1-C30) 烧基、RmY-[其中’ Y係表示S或〇，以及r32係表示具有 或不具有取代基之（C1-C30)烷基、具有或不具有取代基之 (C6-C30)芳基、或具有或不具有取代基之（C3-C30)雜芳 基]、具有或不具有取代基之（C2-C30)烯基、具有或不具有 取代基之（C2-C30)炔基Ai, A2 and ^ to Bs are independent of CR or N; X is a chemical bond, -C(Rll)(Rl2)-, -N(Rl3)-, -S-, _〇- or -SKRhXRu)-; And 1 to R6 and Ru to R15 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, and one or A (C3-C30) aryl group substituted with or without a substituent (C3-C30) cycloalkyl, substituted (C6-C30) aryl group, with or without a substituent (C3-C30) heteroaryl group 5 to 7 membered heterocycloalkyl group having or without a substituent, 5 to 7 membered heterocycloalkyl group fused to one or more aromatic rings having or without a substituent, with or without a substituent (C3-C30)cycloalkyl, (C3-C30)cycloalkyl, cyano, nitro, NR21R22, BR23R24, PR25R26, P(= fused to one or more aromatic rings with or without a substituent 0) R27R28 [wherein, R21 to R28 each independently represent a (C1-C30) alkyl group having or not having a substituent, a (C6-C30) aryl group having or not having a substituent, or having a substituent. (C3-C30)heteroaryl], R29R3〇R3iSi-[ Wherein R29 to R31 independently represent a (C1-C30)alkyl group having or without a substituent, having or not having a (C6-C30) aryl group of 7 95084 201130805, or having a substituent. (C3-C30) Heteroaryl], (C6-C30) aryl (C1-C30) alkyl group with or without a substituent, RmY-[where 'Y represents S or 〇, and r32 represents (C1-C30)alkyl group having no substituent, (C6-C30) aryl group with or without a substituent, or (C3-C30)heteroaryl group with or without a substituent], with or without Substituent (C2-C30)alkenyl, (C2-C30)alkynyl with or without a substituent
或 者’其各自可經由具有或不具有稠合環之經取代或未缓取 代之（C3-C30)伸烷基或經取代或未經取代之（C3-C30)伸烯 基而鍵結至相鄰取代基，以形成脂環族環、單環或多環之 芳香環、或單環或多環之雜芳香環；且環A及環B可各自 獨立表示具有或不具有取代基之（C5_C3〇)脂環族環、具有 或不具有取代基之（C6_C3〇)芳香環、或具有或不具有取代 基之（C6-C30)雜芳香環； W 係表不化學鍵、_(cr5丨R52)m_、-(r5i)C=C(R52)~、 -N(R53)-、-S-、-〇~、—si(R54)(；R55)_、_p(R56)-、 ~P(=0)(R57)---C(=〇)_^_b(R58)_ ； R41至R43及Rsi至R58之定義係與R、Ri至R6及Ru至rI5 之定義相同； 該雜環烷基或雜芳基可含有一個或多個選自B、n、〇、 P(=0)、Si及p之雜原子；以及 ra係表示1至3之整數。 8 95084 201130805 具體而言 構例示之，但並不限於此 ^42Or 'each of which may be bonded to the phase via a substituted or unsuppressed (C3-C30) alkyl or a substituted or unsubstituted (C3-C30) extended alkenyl group, with or without a fused ring. An ortho substituent to form an alicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring; and ring A and ring B may each independently represent a substituent with or without a substituent (C5_C3) 〇) alicyclic ring, (C6_C3〇) aromatic ring with or without a substituent, or (C6-C30) heteroaromatic ring with or without a substituent; W system represents no chemical bond, _(cr5丨R52) M_, -(r5i)C=C(R52)~, -N(R53)-, -S-, -〇~, -si(R54)(;R55)_, _p(R56)-, ~P(= 0) (R57)---C(=〇)_^_b(R58)_ ; R41 to R43 and Rsi to R58 are as defined for R, Ri to R6 and Ru to rI5; The heteroaryl group may contain one or more heteroatoms selected from the group consisting of B, n, hydrazine, P(=0), Si, and p; and the ra system represents an integer from 1 to 3. 8 95084 201130805 Specifically, it is exemplified, but not limited to this ^42
可獨立以下列結Can independently stand as follows
其中， R43及Rsi至R58係獨立表示具有或不具有取代基之 (C1-C30)烷基、具有或不具有取代基之（C6 C3〇)芳基、或 具有或不具有取代基之（C3-C30)雜芳基，或者R51至R58可 經由（C3-C30)伸烷基或（C3-C30)伸烯基而鍵結至相鄰取代 基，以形成脂環族環、單環或多環之芳香環、或單環或多 環之雜芳香環。 【實施方式】 於本發明中，、、烷基〃、、、烷氧基〃及其他含有、、烷基，, 部份之取代基係包括直鏈及分支鏈兩者，且、、環燒基〃係 包括單環烴以及多環烴例如金剛烷基或具有或不具有取代 基之（C7-C30)雙環烷基。 s： 9 95084 201130805 於本發明中，''芳基〃意指自芳香烴去除一個氫原子 後所得之有機基團，且可包括4至7員（尤指5員或6員） 之單環或稠合環，包括複數個藉由單鍵鏈結之芳基。具體 實例包括，但不限於：苯基、萘基、聯苯基、聯三苯基、 蒽基、茚基、苐基、菲基、聯伸三苯基（triphenylenyl)、 芘基、茈基、蒯基（chrysenyl)、稠四苯基（naphthacenyl)、 丙二烯合苐基（fluoranthenyl)等。萘基係包括1-萘基及 2-萘基，蒽基係包括1 -蒽基、2-蒽基及9-慧基，以及第基 係包括1-苐基、2-苐基、3-苐基、4-苐基及9-第基。於本 發明中，A雜芳基〃意指含有作為芳香環骨架原子之1至4 個選自6、！^、0、8、卩(=0)、3丨及？的雜原子，且其餘芳 香環骨架原子為碳之芳基。雜芳基可為5員或6員單環雜 方.基’或為與本壤縮合所得之多ί哀雜方基，並可為部分飽 和。再者’雜芳基係包括一個以上之藉由單鍵鏈結的雜芳 基。雜芳基包括二價芳基，其中，環中之雜原子可經氧化 或四級化（quaternized)以形成諸如Ν-氧化物或四級蜂。 具體實例包括’但不限於：單環雜芳基，諸如呋喃基、售 吩基、吡咯基、咪唑基、吡唑基、噻唑基、嘆二唾基、異 噻唑基、異噚唑基、噚唑基、噚二唑基、三哄基、四哄基'、 三唑基、四唑基、呋咕基（furazanyl)、吡啶基、吡哄基、 嘧啶基、嗒哄基等；多環雜芳基’諸如笨并吱喃基、二笨 并呋喃基、苯并噻吩基、二苯并噻吩基、異苯并咳喃基、 苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異嘴唾某、 苯并曙唾基、異吲哚基、吲哚基、吲嗤基、苯并嗟二。坐美 95084 10 201130805 喹啉基、異喹啉基、噌啉基（cinn〇linyl)、喹唑啉基、喹 亏琳基卡坐基、_咬基、苯并二曙呢基（benzodioxolyl) 等，其N-氧化物（例如吡啶基N_氧化物、喹啉基N_氧化物 等）；其四級鹽等。 本文所述之、、（C1-C30)烷基〃可包含（C1-C20)烷基或 (n-cio)烷基，且、、（C6_C30)芳基〃包含（C6_C2〇)芳基或 (C6-C12)芳基。、、（C3_C30)雜芳基〃包含（C3_C2〇)雜芳基或 (C3-C12)雜芳基，且、、（C3-C30)環烷基〃包含（C3-C20)環 烷基或（C3-C7)環烷基。、'(C2-C30)烯基或炔基〃包含 (C2-C20)烯基或炔基、（C2-C10)稀基或炔基。Wherein R43 and Rsi to R58 independently represent (C1-C30)alkyl group with or without a substituent, (C6 C3〇) aryl group with or without a substituent, or with or without a substituent (C3) a -C30)heteroaryl group, or R51 to R58 may be bonded to an adjacent substituent via a (C3-C30) alkyl group or a (C3-C30) alkenyl group to form an alicyclic ring, a single ring or more An aromatic ring of a ring, or a heterocyclic ring of a monocyclic or polycyclic ring. [Embodiment] In the present invention, the alkyl hydrazine, the alkoxy fluorene, and the other alkyl group-containing substituents include both a straight chain and a branched chain, and The guanidines include monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or (C7-C30)bicycloalkyl groups with or without substituents. s: 9 95084 201130805 In the present invention, ''aryl 〃 means an organic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and may include a single ring of 4 to 7 members (especially 5 or 6 members) Or a fused ring comprising a plurality of aryl groups linked by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, fluorenyl, fluorenyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, fluorene Chrysenyl, naphthacenyl, fluoranthenyl, and the like. The naphthyl group includes a 1-naphthyl group and a 2-naphthyl group, and the anthracene group includes a 1-fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group, and the first group includes a 1-fluorenyl group, a 2-fluorenyl group, and 3- Sulfhydryl, 4-mercapto and 9-diyl. In the present invention, A heteroaryl 〃 means that 1 to 4 atoms which are contained as an aromatic ring skeleton are selected from 6, ^, 0, 8, 卩 (=0), 3 丨 and? a hetero atom, and the remaining aromatic ring skeleton atoms are carbon aryl groups. The heteroaryl group may be a 5- or 6-membered monocyclic heterocyclic group. The base is either a condensed mixture with the soil and may be partially saturated. Further, the 'heteroaryl group' includes one or more heteroaryl groups bonded by a single bond. Heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring can be oxidized or quaternized to form, for example, cerium-oxide or quaternary bees. Specific examples include, but are not limited to, monocyclic heteroaryl groups such as furyl, phenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, succinyl, isothiazolyl, isoxazolyl, anthracene Azolyl, oxadiazolyl, tridecyl, tetradecyl', triazolyl, tetrazolyl, furazanyl, pyridyl, pyridyl, pyrimidinyl, fluorenyl, etc.; polycyclic Aryl' such as stupidinyl, di-p-furanyl, benzothienyl, dibenzothiophenyl, isobenzoheptyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, Benzopyrene, benzoxanthyl, isodecyl, fluorenyl, fluorenyl, benzopyrene. Sitting on the United States 95084 10 201130805 quinolinyl, isoquinolinyl, cinn〇linyl, quinazolinyl, quinoline kika, benzoyl, benzodioxolyl, etc. And its N-oxide (for example, pyridyl N-oxide, quinolyl N-oxide, etc.); its quaternary salt and the like. The (C1-C30)alkyl hydrazine described herein may comprise (C1-C20)alkyl or (n-cio)alkyl, and the (C6_C30) aryl fluorene comprises (C6_C2 fluorene) aryl or C6-C12) aryl. , (C3_C30)heteroarylfluorene comprises (C3_C2〇)heteroaryl or (C3-C12)heteroaryl, and (C3-C30)cycloalkylfluorene comprises (C3-C20)cycloalkyl or ( C3-C7) cycloalkyl. The '(C2-C30)alkenyl or alkynylfluorene comprises a (C2-C20)alkenyl or alkynyl group, a (C2-C10)thrayl group or an alkynyl group.
本文所述之術語、、經取代或未經取代（或具有或不具 有）取代基〃中，術語 '經取代〃意指進一步由未經取代之 取代基所取代。進一步由R、Ri至R6、Ru至r15、r21至r32、 R41至R43及&至R58所取代之取代基，係一個或多個選自 由下列所組成之群組的取代基：氘、鹵素、具有或不具有 鹵素取代基之（C1-C30)烷基、（C6-C30)芳基、具有或不具 有（C6-C30)芳基取代基之（C3-C30)雜芳基、5至7員雜環 烷基、與一個或多個芳香環稠合之5至7員雜環烷基、 (C3-C30)環烷基、與一個或多個芳香環稠合之（C6-C30)環 烷基、RaRbReSi-、（C2-C30)烯基、（C2-C30)炔基、氰基、 咔唑基、-NRdRe、-BRfRg、-、-P(=〇)RjRk、（C6-C30)芳 基（C1-C30)烷基、（C1-C30)烷基（C6-C30)芳基、fx-、 RnC(=〇)-、RnC(=0)0-、羧基、硝基及羥基；且Ra至R1係獨 立表示（C1-C30)院基、（C6_C30)^'基或（C3-C30)雜芳基；X 11 95084 201130805 係表示S或〇 ;以及Γ係表示（cl_C3〇)烷基、（cl_C3〇)烷 氧基、（C6-C30)芳基或（C6-C30)芳氧基。The term 'substituted oxime' as used herein, in the term, substituted or unsubstituted (or with or without) substituent, is intended to be further substituted with an unsubstituted substituent. Substituents further substituted by R, Ri to R6, Ru to r15, r21 to r32, R41 to R43 and & to R58 are one or more substituents selected from the group consisting of hydrazine, halogen (C1-C30)alkyl, (C6-C30) aryl, (C3-C30)heteroaryl, with or without a (C6-C30) aryl substituent, 5 to, with or without a halogen substituent a 5-membered heterocycloalkyl group, a 5 to 7 membered heterocycloalkyl group fused to one or more aromatic rings, a (C3-C30)cycloalkyl group, fused to one or more aromatic rings (C6-C30) Cycloalkyl, RaRbReSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, oxazolyl, -NRdRe, -BRfRg, -, -P(=〇)RjRk, (C6-C30 Aryl (C1-C30) alkyl, (C1-C30)alkyl (C6-C30) aryl, fx-, RnC(=〇)-, RnC(=0)0-, carboxyl, nitro and hydroxy And Ra to R1 independently represent (C1-C30), (C6_C30)^' or (C3-C30)heteroaryl; X 11 95084 201130805 means S or 〇; and Γ indicates (cl_C3〇) Alkyl, (cl_C3〇)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
A 係選自下列結構’且下列結構中之R較佳為氫A is selected from the following structure' and R in the following structure is preferably hydrogen
R係與化學式1中定義者相同 又， 係選自下列結構，但並不限於此The R system is the same as defined in Chemical Formula 1, and is selected from the following structures, but is not limited thereto.
其中， R及心至心係獨立表示齒素、具有或不具有取代基 之（C1-C30)烷基、具有或不具有取代基之（C6_C3〇)芳基、 具有或不具有取代基之（C3-C30)雜芳基或咔唑基；R可為 95084 12 201130805 相同或不同；且a及b係獨立表示0至4的整數。 -較佳者，R及1至R6係獨立表示氫、氟、曱基、乙基、 正丙基、異丙基、正丁基、異丁基、第三丁基、戊基 (pentyl)、戊基（amyl)、己基、庚基、辛基、壬基、癸基、 三氟甲基、苯基、1-萘基、2-萘基、1，2-聯苯基、1，3-聯苯基、1-4-聯苯基、1-菲基、2-菲基、3-菲基、4-菲基、 9-菲基、N-味11坐基、N_苯基_1_°卡。坐基、N_苯基-2_味β坐基、 Ν-苯基_3_σ卡吐基、苯基_4-σ*^哇基、2-°比°定基、3_π比〇定 基、4-^α定基、2-啥琳基、3-啥琳基、4-啥琳基、5-啥琳 基、6-啥琳基、7-喧琳基、8-啥琳基、3-異噎琳基、1-異 喧琳基、4-異喧淋基、5-異噎琳基、6-異喧琳基、7-異01 啉基、8-異喹啉基、9H-苐-2-基、9H-苐-3-基、9H-苐-4-基、9H-苐-1-基、2-σ密咬基、4_π密咬基、5-°密°定基、1，2, 3-三畊-4-基、1，2，3-三畊-5-基、1，3，5-三畊-2-基、 1-二苯并呋喃基、2-二苯并呋喃基、3-二苯并呋喃基、4-二苯并呋喃基、1-二苯并噻吩基、2-二苯并噻吩基、3-二 苯并π塞吩基、4-二苯并α塞吩基、1，2，3，4-四氫-5-萘基、 1，2，3，4-四氫-6-萘基、1，2，3，4-四氫-1-喹啉基、 二苯基胺基、二甲基胺基或甲基苯基胺基，且R及Ri至匕 之該苯基、萘基、聯苯基、菲基、N- °卡π坐基、D比咬基、嗤 淋基、異喧琳基、苐基、。密°定基、三哄基、N-二苯并°卡峻 基或二苯并呋喃基可進一步經一個或多個選自曱基、苯 基、三苯基碎烧基及三甲基破烧基之取代基所取代。 本發明之有機電場發光化合物可藉由下列化合物更 13 95084 201130805 具體例示之，但其並不限於此。Wherein R and a cardiocardium are independently represented by dentate, (C1-C30)alkyl group with or without a substituent, (C6_C3〇) aryl group with or without a substituent, with or without a substituent ( C3-C30)heteroaryl or carbazolyl; R may be the same or different from 95084 12 201130805; and a and b are independently represented by an integer from 0 to 4. Preferably, R and 1 to R6 independently represent hydrogen, fluorine, mercapto, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, Amyl, hexyl, heptyl, octyl, decyl, decyl, trifluoromethyl, phenyl, 1-naphthyl, 2-naphthyl, 1,2-biphenyl, 1,3- Biphenyl, 1-4-biphenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, N-flavor 11-seat, N_phenyl_1_ ° card. Sitting group, N_phenyl-2_flavor β sitting group, Ν-phenyl_3_σ卡基基, phenyl_4-σ*^ 瓦基基, 2-° ratio °定定, 3_π比〇定基, 4- ^α定基, 2-啥琳基, 3-啥琳基, 4-啥琳基, 5-啥琳基, 6-啥琳基, 7-喧琳基, 8-啥琳基, 3-iso Lynn, 1-isoindolyl, 4-isoindolinyl, 5-isoindolyl, 6-isoindolyl, 7-isomorpholinyl, 8-isoquinolinyl, 9H-indole-2 -yl, 9H-indol-3-yl, 9H-indol-4-yl, 9H-indol-1-yl, 2-sigma dimethylidene, 4 _ _ _ _ _ _ _ _ _ _ _ 3-trit-4-yl, 1,2,3-trit-5-yl, 1,3,5-triton-2-yl, 1-dibenzofuranyl, 2-dibenzofuranyl , 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzopyranyl, 4-dibenzo-α Phenyl, 1,2,3,4-tetrahydro-5-naphthyl, 1,2,3,4-tetrahydro-6-naphthyl, 1,2,3,4-tetrahydro-1-quinoline a phenyl group, a naphthyl group, a biphenyl group, a phenanthrenyl group, an N-° card π-spin group, and a phenyl group, a diphenylamino group, a dimethylamino group or a methylphenylamino group. D is more than bite base, 嗤 基, 喧Group, Ti group. The dimethyl group, the tridecyl group, the N-dibenzoxanyl group or the dibenzofuranyl group may be further subjected to one or more selected from the group consisting of an anthracenyl group, a phenyl group, a triphenyl group, and a trimethyl group. Substituted by a substituent. The organic electroluminescent compound of the present invention can be specifically exemplified by the following compound 13 95084 201130805, but it is not limited thereto.
14 95084 20113080514 95084 201130805
本發明之有機電場發光化合物可如下列反應式1所示 而製備。The organic electroluminescent compound of the present invention can be produced as shown in the following Reaction Scheme 1.
S 15 95084 201130805 反應式lS 15 95084 201130805 Reaction formula l
其中， Αι、Α2、Βι 至 Bs、 相同。 X及&至Re係與化學式〗中定義者 本發明提供有機電場發光裴置，其係包括第一電極. 第二電極；以及插置於該第一電極與該第二 ， 或多層有機層；其中，該有機層包含-種❹種 表示之有機電場發光化合物。該有機層可包括—種. 化學式1表示之有機電場發光化合物以作為電場發光主 體，且可包括-種或多種摻雜劑1於本發明之有機電場 發光裝置的摻雜劑並無特別限制，但可選自化學式2 ^示 之化合物： ' 化學式2 MVW3 其中， M1係選自由下列所組成之群組：第7族、第8族、第 95084 16 201130805 9 .族、第10族、第11族、第13族、第14族、第15族及 第16族之金屬；以及 配位子Lm、L1()2及L103係獨立選自下列結構：Among them, Αι, Α2, Βι to Bs, the same. The invention provides an organic electric field illuminating device comprising a first electrode. a second electrode; and interposing in the first electrode and the second or multi-layer organic layer, wherein X and & to Re and Chemical Formula Wherein the organic layer comprises an organic electroluminescent compound represented by the species. The organic layer may include an organic electroluminescent compound represented by Chemical Formula 1 as an electric field luminescence host, and may include one or more kinds of dopants 1 . The dopant of the organic electroluminescence device of the present invention is not particularly limited. However, it may be selected from the compound of the formula 2: 'Chemical Formula 2 MVW3 wherein M1 is selected from the group consisting of: Group 7, Group 8, and 95084 16 201130805 9 . Family, Group 10, 11 The metals of Groups 13, 13th, 14th, 15th and 16th; and the ligands Lm, L1()2 and L103 are independently selected from the following structures:
其中， R2(H至R2〇3係獨立表示氫、具有或不具有齒素取代基之 (C1-C30)烷基、具有或不具有（C1-C30)烷基取代基之 (C6-C30)芳基、或i素； 17 95084 201130805Wherein R 2 (H to R 2 〇 3 is independently represented by hydrogen, (C 1 -C 30 )alkyl having or without a dentate substituent, (C6-C30) having or not having a (C 1 -C 30 ) alkyl substituent; Aryl, or i; 17 95084 201130805
Rm至Rm係獨立表示氫、具有或不具有取代基之 (C1-C30)烷基、具有或不具有取代基之（C1-C30)烷氧基、 具有或不具有取代基之（C3-C30)環烷基、具有或不具有取 代基之（C2-C30)烯基、具有或不具有取代基之（C6-C30)芳 基、具有或不具有取代基之單或二（n-C30)烷基胺基、具 有或不具有取代基之單或二（C6-C30)芳基胺基、SF5、具有 或不具有取代基之三（C1-C30)烷基矽烷基、具有或不具有 取代基之二（C1-C30)烷基（C6-C30)芳基矽烷基、具有或不 具有取代基之三（C6-C30)芳基矽烷基、氰基或鹵素；Rm to Rm independently represent hydrogen (C1-C30)alkyl group with or without a substituent, (C1-C30) alkoxy group with or without a substituent, with or without a substituent (C3-C30) a cycloalkyl group, a (C2-C30) alkenyl group with or without a substituent, a (C6-C30) aryl group with or without a substituent, a mono- or di-(n-C30) group with or without a substituent Alkylamino group, mono or di(C6-C30)arylamino group with or without a substituent, SF5, tri(C1-C30)alkyldecanealkyl group with or without a substituent, with or without a substitution a bis(C1-C30)alkyl (C6-C30) arylalkylene group, a tris(C6-C30)aryldecylalkyl group, a cyano group or a halogen having or without a substituent;
Rm至Rm係獨立表示氫、具有或不具有鹵素取代基之 (C1-C30)烷基、或具有或不具有（C1_C30)烷基取代基之 (C6-C30)芳基；Rm to Rm are independently a hydrogen atom, a (C1-C30) alkyl group having or not having a halogen substituent, or a (C6-C30) aryl group having or not having a (C1_C30) alkyl substituent;
Rm與Rm係獨立表示氫、具有或不具有取代基之 (C卜C30)烷基、具有或不具有取代基之（C6_C3〇)芳基或鹵 素’或Rm與可經由具有或不具有稠合環之（C3_C12) 伸炫•基或（C3-C12)伸烯基而相鏈結，以形成脂環族環、或 單環或多環之芳香環；Rm and Rm independently represent hydrogen (C(C30)alkyl) with or without a substituent, (C6_C3〇)aryl or halogen' or Rm with or without a substituent may or may not be fused via环环(C3_C12) 伸··· or (C3-C12) an alkenyl group and a phase chain to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring;
Rm係表示具有或不具有取代基之（(n_C3〇)烷基、具有 或不具有取代基之（C6-C30)芳基、具有或不具有取代基之 (C5-C30)雜芳基、或鹵素；Rm is a (C6-C30) aryl group with or without a substituent ((C_-C3)), a (C5-C30) aryl group with or without a substituent, or a (C5-C30) heteroaryl group, or halogen;
Rm至Rug係獨立表示氫、具有或不具有取代基之 (C1-C30)烷基、具有或不具有取代基之（C6_C3〇)芳基或 鹵素；以及 95084 18 201130805 Q 係表示 、 R236R236 或 R239 R24° ，其中，R231 至Rm to Rug are independently represented by hydrogen, (C1-C30)alkyl group with or without a substituent, (C6_C3〇) aryl or halogen with or without a substituent; and 95084 18 201130805 Q system representation, R236R236 or R239 R24° , where R231 to
Rm係獨立表示氫、具有或不具有鹵素取代基之（C1_C30) 烧基、（C1-C30)烧氧基、豳素、具有或不具有取代基之 (C6-C30)芳基、氰基或具有或不具有取代基之（C5_C3〇)環 烷基，或匕⑴至Km可各自經由伸烷基或伸烯基而鏈結至相 鄰取代基，以形成螺環或稠合環，或Rm至R242可各自經由 伸烷基或伸烯基而鍵結至！^7或Rm，以形成飽和或不飽和 之稠合環。 化學式2表示之摻雜劑化合物可藉由具有下列結構之 化合物例示之，但並不限於此：Rm is independently represented by hydrogen, (C1_C30) alkyl, (C1-C30) alkoxy, halogen, (C6-C30) aryl with or without a substituent, cyano or (C5_C3〇)cycloalkyl group with or without a substituent, or oxime (1) to Km may each be linked to an adjacent substituent via an alkyl group or an alkenyl group to form a spiro ring or a fused ring, or Rm To R242 can be bonded to each via an alkyl or an alkenyl group! ^7 or Rm to form a saturated or unsaturated fused ring. The dopant compound represented by Chemical Formula 2 can be exemplified by a compound having the following structure, but is not limited thereto:
3 19 95084 2011308053 19 95084 201130805
於本發明之有機電子裝置中，有機層除了包括化學式 1表示之有機電場發光化合物之外，可同時進一步包括一 種或多種選自由芳基胺化合物及苯乙烯基芳基胺化合物所 組成之群組的化合物。該芳基胺化合物或苯乙烯基芳基胺 化合物係例示於韓國專利申請案第10-2008-0123276號、 第 10-2008-0107606 號或第 10-2008-0118428 號中，但不 限於此。 再者，於本發明之有機電場發光裝置中，有機層除了 包括化學式1表示之有機電場發光化合物之外，可進一步 包括一種或多種選自由下列所組成之群組的金屬：第1族 之有機金屬、第2族、第4周期與第5周期之過渡金屬、 鐦系金屬及d-過渡元素，或錯合物化合物。有機層可包括 電場發光層及電荷產生層。 再者，有機層除了包括有機電場發光化合物之外，可 20 95084 201130805 同時包括一層或多層發射藍光、綠光或紅光之有機電場發 光層，以提供發射白光之有機電場發光裝置。發射藍= 綠光或紅光之化合物可由韓國專利申請案第 10-2008-0123276 號、第 10-2008-0107606 號或第 10-2008-0118428號所揭示之化合物例示之，但不限於此。 於本發明之有機電場發光裝置中，選自硫屬化合物 (chalcogenide)層、金屬鹵化物層及金屬氧化物層之層〈後 文中稱為、、表面層"）設置於電極對之—或兩者的内表面 上。更具體而言，可將矽或鋁之硫屬化合物（包括氧化物） 層设置於電場發光介質層之陽極表面上，並可將金屬函化 物層或金屬氧化物層設置於電場發光介質層之陰極表面 上。藉此可得到操作安定性。該硫屬化合物可為，例如以山 (l$xS2)、A1〇x(1$x^1.5)、SiON、SiAlON 等。該金屬 論化物可為，例如LiF、MgF2、Cab、稀土金屬氟化物等。 該金屬氧化物可為，例如CS2〇、Lh〇、Mg〇、Sr〇、Ba〇、Ca〇 等。 於本發明之有機電場發光裝置中，較佳亦可將電子傳 輸，合物與縣性_劑之混合區域、或電洞傳輸化合物 與氧化性摻雜劑之混合區域設置於前述所製造之電極對的 至少-個表面上。於該例子中，由於電子傳輸化合物被還 原成陰離子，因而促進電子自混合區軌人與傳輸至電場 發光介質。此外’由於電洞傳輸化谷物被氧化成陽離子， 因而促進電洞自混合區域注入與傳輸至電場發光介質。較 佳之氧化性掺雜劑係包括各種路易士酸及接受體化合物 95084 21 201130805 riT/〇mP〇Und) 〇 屬、驗金屬化合物、驗土金屬、稀土金屬及其混合物 者’可藉由使用還原性摻雜綱作為電荷產生層來製備旦 有兩層或更多層電場發光狀發射自光的電場發光裝置。、 有益效果 由於本發明之有機電場發光化合物展現良好發光效 率及優異壽命性質，其可祕製造具有極高操作壽命之 ◦LED裝置。 發明模式 本發明將進一步說明關於本發明之有機電場發光化 合物、該化合物之製備方法、以及使用該化合物之裝置的 發光性質。然而’下列實施例僅提供用於例示性說明，而 非意欲限制本發明之範轉。 實施例 [製備例1]化合物21之製備In the organic electronic device of the present invention, the organic layer may further include one or more groups selected from the group consisting of an arylamine compound and a styrylarylamine compound, in addition to the organic electroluminescent compound represented by Chemical Formula 1. compound of. The arylamine compound or the styrylarylamine compound is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. Furthermore, in the organic electric field light-emitting device of the present invention, the organic layer may further include one or more metals selected from the group consisting of: Group 1 organic, in addition to the organic electroluminescent compound represented by Chemical Formula 1. Transition metal, lanthanide metal and d-transition element, or complex compound of metal, Group 2, 4th cycle and 5th cycle. The organic layer may include an electric field luminescent layer and a charge generating layer. Furthermore, the organic layer includes, in addition to the organic electroluminescent compound, one or more layers of an organic electric field emitting layer that emits blue light, green light or red light to provide an organic electric field light emitting device that emits white light. The compound which emits blue = green light or red light can be exemplified by the compounds disclosed in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. In the organic electric field light-emitting device of the present invention, a layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") is disposed on the electrode pair - or On the inner surface of both. More specifically, a layer of chalcogenide (including oxide) of lanthanum or aluminum may be disposed on the anode surface of the electroluminescent luminescent medium layer, and a metal functional layer or a metal oxide layer may be disposed on the electric field luminescent medium layer. On the surface of the cathode. Thereby, operational stability can be obtained. The chalcogen compound may be, for example, a mountain (l$xS2), an A1〇x (1$x^1.5), SiON, SiAlON or the like. The metallization may be, for example, LiF, MgF2, Cab, a rare earth metal fluoride or the like. The metal oxide may be, for example, CS2, Lh, Mg, Sr, Ba, Ca, or the like. In the organic electric field light-emitting device of the present invention, it is preferable to provide an electron transporting compound, a mixed region of the compound and the cation agent, or a mixed region of the hole transporting compound and the oxidizing dopant in the electrode manufactured above. Right on at least one surface. In this example, since the electron transporting compound is reduced to an anion, the electron self-mixing zone is promoted and transmitted to the electric field illuminating medium. Furthermore, since the hole transporting grain is oxidized to a cation, the hole is promoted from the mixed region to be injected and transported to the electric field illuminating medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds 95084 21 201130805 riT/〇mP〇Und) genus, metal compound, soil test metal, rare earth metal and mixtures thereof can be reduced by use The doping class serves as a charge generating layer to prepare an electric field illuminating device in which two or more layers of electric field light are emitted from light. Advantageous Effects Since the organic electroluminescent compound of the present invention exhibits good luminescence efficiency and excellent lifetime properties, it is possible to manufacture a ◦LED device having an extremely high operational life. Mode for Invention The present invention will further explain the luminescent properties of the organic electric field luminescent compound of the present invention, the preparation method of the compound, and the apparatus using the same. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the invention. EXAMPLES [Preparation Example 1] Preparation of Compound 21
化合物1-1之製備 將咔唑（20. 5公克（g)，122. 7毫莫耳（mmol))溶解於 DMF(200亳升（mL))後，於其内緩慢加入其中溶有NaH(6. 8 g， 22 95084 201130805 177. 1 mmol, 60%)之DMF(200 mL)溶液。攪拌混合物1小 時後’將該混合物緩慢加至其中溶有2, 4, 6-三氯嘧啶（25 g， 136· 2 mmol)之DMF(400 mL)溶液，並攪拌24小時。當藉 由緩慢加入H2〇使反應完成時，過濾所得固體並以EA/MeOH 加熱得到之混合物’以獲得化合物1-1(25 g，79.5 mmol， 50〇/〇)。 化合物1-2之製備 將 2, 4, 6-三氯嘧咬（25 g，136. 2 mmol)、苯删酸（36. 5 g，299. 3 mmol)、及肆（二笨基鱗）把（1.11 g，〇. 96 醒〇1) 溶解於甲苯（408 mL)後’於其内加入2· 0M之Na2C〇3水溶液 (204 mL)及乙醇（204 mL)。於12(TC回流下攪拌混合物2 小時。反應完成時，以ΕΛ萃取及藉由管柱色層分析法純化 而獲得化合物 1-2(25 g，93. 7 mmol，69%)。 化合物21之製備 將化合物 1-2(21. 2 g，79. 5 mmol)溶解於 DMF( 100 mL) 後，於其内緩慢加入其中溶有NaH(3 6g，95.4mm〇1，6〇%) 之DMF(l〇〇 mL)溶液。攪拌混合物丨小時後，於其内缓慢 加入其中溶有化合物卜1(1〇 g，31· 8 mm〇1)之MF(1〇〇乩） 溶液’並攪拌混合物24小時。當藉由緩慢加入h2〇使反應 完成時’過濾所得固體並依序以EA/Me〇H& EA加熱以再結 晶，獲得化合物21 (5 g，7. 〇随〇1，22%)。 根據製備例1製備有機電場發光化合物1至39。所製 備之有機電場發光化合物的lH歷及奶/FAB數據顯示於 表1中。 5 23 95084 201130805 表1 化合物 1H NMR(CDCl3, 200 MHz) MS/FAB 實測值 計算值 1 δ = 2.73(12H, s), 8.的(1H. s>, 7·11(1Η, s), 7·25~7.33(3Η· m), 7.47~7.5(2H, m), 7.63(1 H, m), 7.94(1 H, m), 8.12(1H, m), 8.51~8.55(2H, m) 456.54 456.21 2 δ = 7.25~7.33(3H, m), 7.41 -7.51 (14H, m). 7.63(1 H. m), 7.79(8H, m), 7.94(1H, m), 8.12{1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) 704.82 704.27 3 δ = 1.72(16H, m), 2.74(16H, m), 6.88(4H, m), 6.98(4H. m), 7.15(4H, m). 7.25~7.33(3H, m). 7.47~7.5(2H. m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m). 8.37(1H, s), 8.51-8.55(2H, m), 8.59(1 H, s) 921.18 . 920.46 4 δ = 7.25~7.36(7H, m), 7.47-7.5(2H, m), 7.63(1 H, m), 7.85(4H, m), 7.94(1H, m), 8.12(1H, m), 8.4(4H, m), 8.51~8.59(6H, m), 10.29(1H. s). 10.51(1 H.s) 708.77 708.25 5 δ = 1.96(8H, m). 2.76(8H, m), 3.06{8H, m), 5.26(1H, s), 5.48(1H, s), 6.55(4H, m), 6.72(4H, m). 7.05~7.07(8H, m), 7.25~7.33(3H, m), 7.47~7.5(2H, m), 7.63(1 H, m), 7.94(1 H, m), 8.12(1 H, m), 8.51-8.55(2H, m) 925.13 924.44 6 δ = 5.26(1 H, s), 5.48{1H, s), 6.63(16H, m), 6.81(8H, m), 7.2~7.33(19H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7,94(1H, m), 8.12(1H, m), 8.51~8.55(2H, m) 1069.26 1028.44 7 δ = 0.25(9H, s), 7.25-7.3^, m), 7.41~7.51(13H, m), 7.63(1H, m), 7.77~7.79(8H, m), 7.94(1 H. m). 8.12(1 H. m), 8.37(1H, s), 8·51~8.55(2Η, m), 8.59(1H, s) 777.00 776.31 24 95084 201130805 8 δ = 7.25(1Η, m). 7.29(1Η, m), 7.33(1Η, m), 7.37~7.46(27Η, m), 7.61~7.63(2Η, m). 7.76^7.79(7Η, m), 7.89-7.94(2Η. m), 8.12(1Η, m). 8.37(1Η, s), 8.51~8.55(2Η, m), 8.59(1Η, 8) 963.21 962.36 9 δ = 7,25-7·33(3Η. m), 7·41 - 7.52(18Η· m), 7.63(1 Η, m), 7.79"7.85(8Η, m), 7.94(1Η, m), 8.12{1Η, m), 8.3(4Η, m)f 8.37{1H, s), 8.51〜8.55(2Η, m), 8·59(1Η, s) 857.01 856.33 10 δ = 2.34(6Η, s), 6.88(1Η, m), 7.39-7.51 (15Η, m), 7.79-7.82(9Η, m), 7.99(1Η, m)( 8.37(1Η, s), 8.51(1Η. m), 8.59(1Η, s), 8J2(1H, m) 732.87 732.30 11 δ = 7.25(1H, m), 7.33{1H, 7·41~7·51(13Η· m), 7·63~7.67(4Η· m), 7.79(8H, m), 7.94(1H, m), 8.16(1H, m), 8.37(1H, s). 8.51-8.55(3H, m), 8.59(1H,s) 754.88 754.26 12 δ = 7.25(1H, m), 7.33(1H, m). 7.41-7.51 (13H, m), 7.57(1H, m), 7.67(2H, m), 7.79(8H, m). 7.94(1H, m), 8.12~8.16(2H, m), 8.37(1H, s), 8.51~8.55(3H, m). 8.59(1 H, s) 764.88 " 754.28 13 δ = 7.06(1H, m), 7.41~7.51(13H· m)· 7.63〜7.67(4H· m), 7·79(βΗ, m), 7.92(1H, m), 8.16(1H( m), 8.22(1H, m), 8.37{1H, s), 8.51-8.54(2H1 m)p 8.59(1H, s) 772.87 772.28 14 δ = 7.25(1H, m), 7.33{1H, m), 7.4-7.55(15H, m)( 7.67(2H, m), 7.79(8H, m), 7.94(1H, m), 8.16(2H( m), 8.37(1H, s)p 8.51-8.55(2H, m), 8,59(1H,s>,(H·) 754.88 754.28 15 δ = 7·25~7·33(6Η· m), 7·41~7·51(14Η, m), 7·63(2Η, m), 7.79(8H· m)· 7.94-7.98(3H, m). 8.12(1H, m), 8.37(1Η, s). 8.61-8.55(3H, m), 8.59(1H, 6) 870.01 869.33 16 δ = 1J2(6H, s), 6.55(2H, m), 6.73(2H( m)( 6.88(1 H. m)t 7·02~7·05(4Η. m>· 7·41(4Η· 7·51(8Η_ m)，7.73〜7·79(9Η· m}, 8.37(1H,s)t 8.59(1 H( s) 746.90 746,32 17 δ = 0.66(6H( s)( 6.73(4H, m), 6.88(1H, m), 7.21(2H, m), 7.3(2H( m)f 762.97 762,29 25 95084 201130805 7.41(4Η, m), 7.51(8Η, m). 7.73-7.79(9Η, m), 8.37(1Η, s), 8.59(1Η, s) 18 δ = 6.38(4Η, m), 6.56(4Η, m), 8.63(2Η, m), β.81(1Η, m), 6.88(1 Η. m), 7.2(2Η, m), 7.41(4Η, m), 7.51(8Η, m). 7.73~7.79(9Η, m), 8.37(1H,s), 8.59(1 Η, s) 795.93 795,31 19 δ = 6.88(1 Η, m), 6.97(2Η, m), 7.16-7.21 (6Η, m), 7.41(4Η, m), 7.51(8Η, m), 7.73~7.79(9Η, m), 8.37(1Η, s). 8.59{1Η, s) 736.88 736.24 20 δ = 6.59(2Η, m), 6.77(2Η, m), 6.88~6.92(5Η, m), 7.41(4Η, m). 7.51(8Η, m). 7.73-7.79(9Η. m). 8.37(1Η, s), 8.59(1Η, s) 720.82 720.26 21 δ = 7_26-7_33(3Η, m), 7.41(4Η· m)· 7·5-7·51(9Η, m), 7·63(1Η, m)· 7_79(8Η, 7·94(1Η, m)· 8·12(1Η· m)· 8·55(1Η, m>· 8·59(2Η，s). 8.75{1H(s) 705.81 705.26 22 δ = 7·25~7·33(3Η, m)· 7·41(4Η, m), 7·5~7·51(9Η. m), 7·63(1Η· m). 7.79(8Η, m)( 7.94(1Η, m), 8.12(1Η, m), 8.55{1Η, m)( 8.59(2Η, S) 706J9 - 706.26 23 δ = 7·25~7,33(3Η, m>· 7.41(4Η· m)· 7·5~7,51{9Η· m), 7·63(1Η, m), 7·74(1Η, s>. 7·79(8Η· m), 7·94(1Η· m), 8·12(1Η· m}· 8.55(1Η_ m), 8·59(2Η, s) 705.81 705.26 24 δ = 7.25-7.33(βΗ, m), 7.41-7.51 (14Η, m), 7.58-7.63(6Η, m), 7.69(1Η( m), 7.77-7.79(6Hf m), 7.87(1H, m). 7.94-8(3H, m), 8.12(2H, m)f 8.18(1H, m), 8.55(2H, m), 8.59(2H( s), 8.75(1H, s) 1036.19 1035.38 25 δ = 7.25-7.33(3H, m), 7.41(4H( m), 7.48-7.63(26H, m)( 7.7-7.75(8H. m), 7·94(1Η, m), 8.12(1H, m), 8_55(1H, m>. 8_59(2H. s). 8·75(1Η, s) 1010.19 1009.39 2β δ - 7.32 〜7,41(8H, m), 7·51(8Η, m}. 7.66-7.81(19H, m), 7.87-7.89(3Η, m), 8(1H, m), 8.18(1H, m), 8.59(2H, s)f 8.75(1Η, s) 1038.16 1037.35 27 δ = 7.25~7.33(3H, m), 7.41-7.51 (19H, m), 7.58~7.63{5H, m), 7.69(2H, m), 7.77-7.79(12H, m), 7.87(2H, m), 7.94-8(3H, m). 8.12(1Ht m), 8.18(2H, m), 8.55(1 H, m). 8.59(2H, s), 8.75(1 H, s) 1188.38 1187.44 26 95084 201130805 28 δ = 7.41(4Η, m), 7.5~7.52(12Η, m), 7.69(1Η, m), 7.77-7.79(1 OH, m), 7.86-7.87(3H, m), 7.98~8(7H, m), 8.18(1H, m), 8.45(2H, m), 8.59(2H, s), 8.75(1H, s) 1070.29 1069.30 29 δ = 7.25(1H, m), 7.32~7.41(7H, m), 7.51(8H, m), 7.66-7.81 (14H, m), 7.87~7.94(3H, m), 8.55(1 H, m), 8.59(2H, s), 8.75(1 H, s) 871.98 871.31 30 δ = 7.25(2H, m), 7.33(2H, m), 7.41-7.51 (15H, m), 7.58(2H, m), 7.69(2H, m), 7.77-7.79(10H, m), 7.87(2H, m). 7.94(2H, m), 8.55(2H, m), 8.59(2H, s), 8.75(1 H, s) 947,09 946.35 31 δ = 7.25(1H, m). 7.33{1H, m), 7.41(4H, m), 7.5-7.52(10H, m), 7.69(1H, m), 7.77~7.79(9H, m), 7.86-7.87{2H, m). 7.94~8(4H, m), 8.45(1H, m). 8.55(1H, m). 8.59(2H, s), 8.75(1 H. $) 888.05 887.28 32 δ » 7(1 H, m), 7.25~7.26(2H, m), 7.33(1 H. m). 7.41 (4H, m), 7.51 (9H, m), 7.72(1H, m), 7.79(8H, m), 7.94{1H. m). 8.28(1H, m). 8.38(1H, m), 8.5-8.55(2H, m), 8.59(2H, s), 8.75(1 H, s) 782.89， 782.29 33 δ = 7·25(1Η，m)· 7,33,7-41(6H, m), 7.51(8H, m), 7·79(8Η_ 7.94(1H, m). 8.43(1H, m), 8.55(1H, m). 8.59ί2Η, s), 8.75(lHt s), 8.87(1 H,m) 706.79 706.26 34 δ = 2.34(6H, s), 7.08(1H, s), 7.25(1H, m), 7.33(1H, m), 7.41(4Hf m), 7.51(8H, m), 7.79(8Η. m), 7.87(1H, s)f 7.94(1H, m). 8.55(1H, m), 8.59(2H(S), 8.75(1H, s) 733.86 733.30 35 δ = 7.25(1H, m), 7.33(1H, m), 7.41(4H, m). 7.51(9H, m). 7.79(8H, m), 7.94(1H, m), 8.43(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s), 9.34(1 H, m) 706.79 706.26 36 δ = 7.25(1H, m)( 7.33-7.41(6H, m)( 7,51(8Hf m), 7.79(8H, m), 7.94(1H, m), 8.43(1H. m), 8.51-8.55(2H, m), 8.59(2H, s). 8.75(1H, s) 706.79 706.26 37 δ = 7.38-7.41 (6H, m), 7.51 (8H, m), 7.79(8H, m). 8.43(2H, m), 8.59(2H, s), 8.75(1 H, s), 8.87(2H, m) 707.78 707.25 36 δ = 7.06(1H, m), 7.31(1H, m), 7.41(4H, m), 7.51(8H, m), 7.61(1H, m), 7.79(8H, m), 7.92(1 H, m), 8.06(1 H, m), 8.22(1 H, m), 8.59(2H, s). 8.75(1H, s) 741.79 741,25 39 δ = 2.34(6H, s), 7.19-7.25(3H, m). 7.33-7.41(6H, m), 7.51(4H, m). 7.6(2H, m), 7.79(6H, m), 7.94(1 H, m), 8.43(1 H, m), 8.55(1 H, m). 8.59(2H, s), 8.75(1H, s). 8.87(1R. m) 734.85 734.29 27 95084 201130805 [實施例1]使用本發明之有機電場發光化合物之 0LED裝置的製造 使用本發明之電場發光材料製造0LED裝置，首先， 使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水清洗由 ◦LED用玻璃（Samsung Corning製造）所得之透明電極ιτο 薄膜（150/口），並儲存於異丙醇中備用。 然後’將ΙΤ0基板裝配於真空氣相沈積裝置之基板夾 中，並將4,4，，4” -參（N，N-(2-萘基）-苯基胺基）三苯胺 (2-TNATA)置於該真空氣相沈積裝置之小室中，然後於腔室 内令其通氣以達到1〇—6托（torr)真空。接著，對該小室施 加電流以揮發2-TNATA，從而於該ΙΤ0基板上形成厚度為 6〇奈米（nm)之電洞注入層。 接著’將N，N，-雙（α-萘基）-N，N，-二苯基-4,4，-二胺（NPB)置於該真空氣相沈積裝置之另一小室中，並對該 小室施加電流以揮發NPB，從而於該電洞注入層上形成厚 度為20 ηιη之電洞傳輸層。形成電洞注入層及電洞傳輸層 之後’以下列方式於其上形成電場發光層。將化合物16 置於真空氣相沈積裝置之一小室中作為主體，並將化合物 Ir(ppy)3 [參（2~笨基吼咬）銀]置於另一小室中作為摻雜 劑。以不同速率蒸發該兩種材料，從而以4至1〇重量％於 該電洞傳輸層上氣相沉積厚度為30 nm之電場發光層。 接著’氣相沈積厚度為20 nm之參（8-經基啥琳基）紹 (III)(Alq)作為電子傳輸層。然後，氣相沈積厚度為工至 2 nm之具有下列結構的8-羥基喹琳鐘 95084 28 201130805Preparation of Compound 1-1 After carbazole (20.5 g (g), 122.7 mmol (mmol)) was dissolved in DMF (200 liters (mL)), it was slowly added thereto to dissolve NaH. (6. 8 g, 22 95084 201130805 177. 1 mmol, 60%) in DMF (200 mL). After the mixture was stirred for 1 hour, the mixture was slowly added to a solution of 2,4,6-trichloropyrimidine (25 g, 136. 2 mmol) in DMF (400 mL) and stirred for 24 hours. When the reaction was completed by slowly adding H.sub.2, the obtained solid was filtered and evaporated to afford </ RTI> </ RTI> </ RTI> </ RTI> MeOH to afford compound 1-1 (25 g, 79.5 mmol, 50 〇 / 。). Preparation of compound 1-2 will be 2,4,6-trichloropyrimidine (25 g, 136.2 mmol), benzene-depleted acid (36.5 g, 299.3 mmol), and hydrazine (two stupid scales) After dissolving (1.11 g, 〇. 96 〇1) in toluene (408 mL), a 2.0 M aqueous solution of Na 2 C 〇 3 (204 mL) and ethanol (204 mL) were added. The mixture was stirred at 12 °C for 2 hours. Upon completion of the reaction, the mixture was purified by column chromatography and purified by column chromatography to give compound 1-2 (25 g, 93.7 mmol, 69%). Preparation After dissolving Compound 1-2 (21. 2 g, 79.5 mmol) in DMF (100 mL), slowly add DMF in which NaH (3 6 g, 95.4 mm 〇1,6〇%) was dissolved. (l〇〇mL) solution. After stirring the mixture for a few hours, slowly add MF (1〇〇乩) solution in which compound b (1〇g, 31·8 mm〇1) was dissolved in the mixture and stir the mixture. 24 hours. When the reaction was completed by slowly adding h2 hydrazine, the resulting solid was filtered and sequentially heated with EA/Me 〇H & EA to recrystallize to obtain compound 21 (5 g, 7. 〇1,22%) The organic electroluminescent compounds 1 to 39 were prepared according to Preparation 1. The lH calendar and milk/FAB data of the prepared organic electroluminescent compound are shown in Table 1. 5 23 95084 201130805 Table 1 Compound 1H NMR (CDCl3, 200 MHz) MS/FAB measured value 1 δ = 2.73(12H, s), 8. (1H. s>, 7·11(1Η, s), 7·25~7.33(3Η· m), 7.47~7.5 (2H, m), 7.63(1 H, m) , 7.94(1 H, m), 8.12(1H, m), 8.51~8.55(2H, m) 456.54 456.21 2 δ = 7.25~7.33(3H, m), 7.41 -7.51 (14H, m). 7.63(1 H. m), 7.79(8H, m), 7.94(1H, m), 8.12{1H, m), 8.37(1H, s), 8.51~8.55(2H, m), 8.59(1H, s) 704.82 704.27 3 δ = 1.72(16H, m), 2.74(16H, m), 6.88(4H, m), 6.98(4H.m), 7.15(4H, m). 7.25~7.33(3H, m). 7.47~7.5 (2H.m), 7.63(1H, m), 7.94(1H, m), 8.12(1H, m). 8.37(1H, s), 8.51-8.55(2H, m), 8.59(1 H, s) 921.18 . 920.46 4 δ = 7.25~7.36(7H, m), 7.47-7.5(2H, m), 7.63(1 H, m), 7.85(4H, m), 7.94(1H, m), 8.12(1H, m), 8.4(4H, m), 8.51~8.59(6H, m), 10.29(1H.s). 10.51(1 Hs) 708.77 708.25 5 δ = 1.96(8H, m). 2.76(8H, m), 3.06{8H, m), 5.26(1H, s), 5.48(1H, s), 6.55(4H, m), 6.72(4H, m). 7.05~7.07(8H, m), 7.25~7.33(3H, m), 7.47~7.5(2H, m), 7.63(1 H, m), 7.94(1 H, m), 8.12(1 H, m), 8.51-8.55(2H, m) 925.13 924.44 6 δ = 5.26 (1 H, s), 5.48{1H, s), 6.63(16H, m), 6.81(8H, m), 7.2~7.33(19H, m), 7.47~7.5(2H, m), 7.63(1H, m), 7,94(1H, m), 8.12(1H, m), 8.51~8.55(2H, m) 1069.26 1028.44 7 δ = 0.25( 9H, s), 7.25-7.3^, m), 7.41~7.51(13H, m), 7.63(1H, m), 7.77~7.79(8H, m), 7.94(1 H. m). 8.12(1 H m), 8.37(1H, s), 8.51~8.55(2Η, m), 8.59(1H, s) 777.00 776.31 24 95084 201130805 8 δ = 7.25(1Η, m). 7.29(1Η, m), 7.33(1Η, m), 7.37~7.46(27Η, m), 7.61~7.63(2Η, m). 7.76^7.79(7Η, m), 7.89-7.94(2Η. m), 8.12(1Η, m). 8.37(1Η, s), 8.51~8.55(2Η, m), 8.59(1Η, 8) 963.21 962.36 9 δ = 7,25-7·33(3Η. m), 7·41 - 7.52(18Η· m) , 7.63(1 Η, m), 7.79"7.85(8Η, m), 7.94(1Η, m), 8.12{1Η, m), 8.3(4Η, m)f 8.37{1H, s), 8.51~8.55 (2Η, m), 8·59(1Η, s) 857.01 856.33 10 δ = 2.34(6Η, s), 6.88(1Η, m), 7.39-7.51 (15Η, m), 7.79-7.82(9Η, m) , 7.99(1Η, m)( 8.37(1Η, s), 8.51(1Η. m), 8.59(1Η, s), 8J2(1H, m) 732.87 732.30 11 δ = 7.25(1H, m), 7.33{1H , 7·41~7·51(13Η·m), 7.63~7.67(4Η·m), 7.79(8H, m), 7.94(1H, m), 8.16(1H, m), 8.37(1H, s). 8.51-8.55(3H, m), 8.59(1H,s) 754.88 754.26 12 δ = 7.25(1H, m), 7.33(1H, m). 7.41-7.51 (13H, m), 7.57(1H, m), 7.67(2H, m), 7.79(8H, m). 7.94( 1H, m), 8.12~8.16(2H, m), 8.37(1H, s), 8.51~8.55(3H, m). 8.59(1 H, s) 764.88 " 754.28 13 δ = 7.06(1H, m) , 7.41~7.51(13H· m)· 7.63~7.67(4H· m), 7.79(βΗ, m), 7.92(1H, m), 8.16(1H( m), 8.22(1H, m), 8.37 {1H, s), 8.51-8.54(2H1 m)p 8.59(1H, s) 772.87 772.28 14 δ = 7.25(1H, m), 7.33{1H, m), 7.4-7.55(15H, m)( 7.67( 2H, m), 7.79(8H, m), 7.94(1H, m), 8.16(2H(m), 8.37(1H, s)p 8.51-8.55(2H, m), 8,59(1H,s> , (H·) 754.88 754.28 15 δ = 7·25~7·33(6Η· m), 7·41~7·51(14Η, m), 7·63(2Η, m), 7.79(8H· m ) 7.94-7.98(3H, m). 8.12(1H, m), 8.37(1Η, s). 8.61-8.55(3H, m), 8.59(1H, 6) 870.01 869.33 16 δ = 1J2(6H, s ), 6.55(2H, m), 6.73(2H( m)( 6.88(1 H. m)t 7·02~7·05(4Η. m>· 7·41(4Η· 7·51(8Η_ m) , 7.73~7·79(9Η· m}, 8.37(1H,s)t 8.59(1 H( s) 746.90 746,32 17 δ = 0.66(6H( s)( 6.73(4H, m), 6.88(1H , m), 7.21(2H, m), 7.3(2H( m)f 762.97 762,29 25 95084 201130805 7.41(4Η, m), 7.51(8Η, m). 7.73-7.79(9Η, m), 8.37( 1Η, s), 8.59(1Η, s) 18 δ = 6.38(4Η, m), 6.56(4Η, m), 8.63(2Η, m), β.81(1Η, m), 6.88(1 Η. m), 7.2(2Η, m), 7.41(4Η, m), 7.51(8Η, m). 7.73~ 7.79(9Η, m), 8.37(1H,s), 8.59(1 Η, s) 795.93 795,31 19 δ = 6.88(1 Η, m), 6.97(2Η, m), 7.16-7.21 (6Η, m ), 7.41(4Η, m), 7.51(8Η, m), 7.73~7.79(9Η, m), 8.37(1Η, s). 8.59{1Η, s) 736.88 736.24 20 δ = 6.59(2Η, m), 6.77(2Η, m), 6.88~6.92(5Η, m), 7.41(4Η, m). 7.51(8Η, m). 7.73-7.79(9Η. m). 8.37(1Η, s), 8.59(1Η, s) 720.82 720.26 21 δ = 7_26-7_33(3Η, m), 7.41(4Η· m)· 7·5-7·51(9Η, m), 7·63(1Η, m)· 7_79(8Η, 7 ·94(1Η, m)· 8·12(1Η· m)· 8·55(1Η, m>· 8·59(2Η,s). 8.75{1H(s) 705.81 705.26 22 δ = 7·25~ 7·33(3Η, m)· 7·41(4Η, m), 7·5~7·51(9Η. m), 7·63(1Η· m). 7.79(8Η, m)( 7.94(1Η) , m), 8.12(1Η, m), 8.55{1Η, m)( 8.59(2Η, S) 706J9 - 706.26 23 δ = 7·25~7,33(3Η, m>· 7.41(4Η· m)· 7·5~7, 51{9Η· m), 7·63(1Η, m), 7·74(1Η, s>. 7·79(8Η· m), 7·94(1Η· m), 8 ·12(1Η· m}· 8.55(1Η_ m), 8·59(2Η, s) 705.81 705.26 24 δ = 7.25-7.33( Η, m), 7.41-7.51 (14Η, m), 7.58-7.63(6Η, m), 7.69(1Η(m), 7.77-7.79(6Hf m), 7.87(1H, m). 7.94-8(3H , m), 8.12(2H, m)f 8.18(1H, m), 8.55(2H, m), 8.59(2H( s), 8.75(1H, s) 1036.19 1035.38 25 δ = 7.25-7.33(3H, m ), 7.41(4H(m), 7.48-7.63(26H, m)(7.7-7.75(8H.m), 7.94(1Η, m), 8.12(1H, m), 8_55(1H, m>. 8_59(2H. s). 8·75(1Η, s) 1010.19 1009.39 2β δ - 7.32 〜7,41(8H, m), 7·51(8Η, m}. 7.66-7.81(19H, m), 7.87 -7.89(3Η, m), 8(1H, m), 8.18(1H, m), 8.59(2H, s)f 8.75(1Η, s) 1038.16 1037.35 27 δ = 7.25~7.33(3H, m), 7.41 -7.51 (19H, m), 7.58~7.63{5H, m), 7.69(2H, m), 7.77-7.79(12H, m), 7.87(2H, m), 7.94-8(3H, m). 8.12 (1Ht m), 8.18(2H, m), 8.55(1 H, m). 8.59(2H, s), 8.75(1 H, s) 1188.38 1187.44 26 95084 201130805 28 δ = 7.41(4Η, m), 7.5 ~7.52(12Η, m), 7.69(1Η, m), 7.77-7.79(1 OH, m), 7.86-7.87(3H, m), 7.98~8(7H, m), 8.18(1H, m), 8.45(2H, m), 8.59(2H, s), 8.75(1H, s) 1070.29 1069.30 29 δ = 7.25(1H, m), 7.32~7.41(7H, m), 7.51(8H, m), 7.66- 7.81 (14H, m), 7.87~7.94(3H, m), 8.55(1 H, m), 8.59(2H, s), 8.75(1 H, s) 871.98 871.31 30 δ = 7.25(2H, m), 7.33(2H, m), 7.41-7.51 (15H, m), 7.58(2H , m), 7.69(2H, m), 7.77-7.79(10H, m), 7.87(2H, m). 7.94(2H, m), 8.55(2H, m), 8.59(2H, s), 8.75( 1 H, s) 947,09 946.35 31 δ = 7.25(1H, m). 7.33{1H, m), 7.41(4H, m), 7.5-7.52(10H, m), 7.69(1H, m), 7.77 ~7.79(9H, m), 7.86-7.87{2H, m). 7.94~8(4H, m), 8.45(1H, m). 8.55(1H, m). 8.59(2H, s), 8.75(1 H. $) 888.05 887.28 32 δ » 7(1 H, m), 7.25~7.26(2H, m), 7.33(1 H. m). 7.41 (4H, m), 7.51 (9H, m), 7.72 ( 1H, m), 7.79(8H, m), 7.94{1H. m). 8.28(1H, m). 8.38(1H, m), 8.5-8.55(2H, m), 8.59(2H, s), 8.75 (1 H, s) 782.89, 782.29 33 δ = 7·25(1Η,m)· 7,33,7-41(6H, m), 7.51(8H, m), 7·79(8Η_ 7.94(1H, m). 8.43(1H, m), 8.55(1H, m). 8.59ί2Η, s), 8.75(lHt s), 8.87(1 H,m) 706.79 706.26 34 δ = 2.34(6H, s), 7.08( 1H, s), 7.25(1H, m), 7.33(1H, m), 7.41(4Hf m), 7.51(8H, m), 7.79(8Η.m), 7.87(1H, s)f 7.94(1H, m). 8.55(1H, m), 8.59(2H(S), 8.75(1H, s) 733.86 733.30 35 δ = 7.25(1H, m), 7.33(1H, m) , 7.41(4H, m). 7.51(9H, m). 7.79(8H, m), 7.94(1H, m), 8.43(1H, m), 8.55(1H, m), 8.59(2H, s), 8.75(1H, s), 9.34(1 H, m) 706.79 706.26 36 δ = 7.25(1H, m)( 7.33-7.41(6H, m)( 7,51(8Hf m), 7.79(8H, m), 7.94(1H, m), 8.43(1H.m), 8.51-8.55(2H, m), 8.59(2H, s). 8.75(1H, s) 706.79 706.26 37 δ = 7.38-7.41 (6H, m), 7.51 (8H, m), 7.79(8H, m). 8.43(2H, m), 8.59(2H, s), 8.75(1 H, s), 8.87(2H, m) 707.78 707.25 36 δ = 7.06(1H , m), 7.31(1H, m), 7.41(4H, m), 7.51(8H, m), 7.61(1H, m), 7.79(8H, m), 7.92(1 H, m), 8.06(1 H, m), 8.22(1 H, m), 8.59(2H, s). 8.75(1H, s) 741.79 741,25 39 δ = 2.34(6H, s), 7.19-7.25(3H, m). 7.33 -7.41(6H, m), 7.51(4H, m). 7.6(2H, m), 7.79(6H, m), 7.94(1 H, m), 8.43(1 H, m), 8.55(1 H, m). 8.59 (2H, s), 8.75 (1H, s). 8.87 (1R.m) 734.85 734.29 27 95084 201130805 [Example 1] Manufacture of an OLED device using the organic electroluminescent compound of the present invention using the present invention The electric field luminescent material is used to manufacture the OLED device. First, the ultrasonic wave is sequentially washed with trichloroethylene, acetone, ethanol and distilled water. ◦LED obtained from glass (Samsung Corning Ltd.) ιτο a transparent electrode film (150 / mouth), and stored in isopropanol standby. Then 'mount the ΙΤ0 substrate into the substrate holder of the vacuum vapor deposition apparatus, and 4,4,,4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenylamine (2- TNATA) is placed in the chamber of the vacuum vapor deposition apparatus, and then ventilated in the chamber to reach a vacuum of 1 to 6 torr. Then, a current is applied to the chamber to volatilize 2-TNATA, thereby A hole injection layer having a thickness of 6 nanometers (nm) is formed on the substrate. Then 'N,N,-bis(α-naphthyl)-N,N,-diphenyl-4,4,-diamine (NPB) is placed in another chamber of the vacuum vapor deposition apparatus, and a current is applied to the chamber to volatilize NPB, thereby forming a hole transport layer having a thickness of 20 ηη on the hole injection layer. After the layer and the hole transport layer, an electric field light-emitting layer is formed thereon in the following manner. The compound 16 is placed in a chamber of a vacuum vapor deposition apparatus as a main body, and the compound Ir(ppy)3 [parameter (2~ stupid) The base is placed in another chamber as a dopant. The two materials are evaporated at different rates to 4 to 1% by weight of the hole. An electric field luminescent layer with a thickness of 30 nm is vapor-deposited on the transport layer. Then, a vapor-deposited 20 nm-thick ginseng (8-pyridyl-based) (III) (Alq) is used as an electron transport layer. The phase deposition thickness is 8 nm. The 8-hydroxyquinoline clock 90084 28 201130805 has the following structure.
Liq)作為電子注入層後，使用另一真空氣相沈積裝置形成 厚度為150 nm之鋁（A1)陰極，以製造〇LED。用於該0LED 之各個化合物皆是藉由在1〇-6 t〇rr真空昇華而純化者。 結果’於電® 6. 7V有4. 1毫安培（mA)/cm2電流流動， 且證實發出1308 cd/m2之綠光。 [實施例2] 除了於電場發光層上改成使用化合物19作為主體材 料以及使用Ir(ppy)3 [參（2_苯基吡啶）銥]作為電場發光 摻雜劑之外，根據實施例1所述之相同方法製造0LED裝置。 結果，於電壓為6. 8V有4. 0 mA/cm2之電流流動，且 證實發出1210 cd/m2之綠光。 [實施例3] 除了於電場發光層上改成使用化合物21作為主體材 料以及使用Ir(ppy)3 [參（2-苯基吼啶）銥]作為電場發光 摻雜劑之外，根據實施例1所述之相同方法製造OLED裝置。 結果，於電壓7. 0V有3. 8 mA/cm2之電流流動，且證 實發出1225 cd/m2之綠光。 [實施例4] 除了於電場發光層上改成使用化合物30作為主體材 料以及使用Ir(ppy)3 [參（2-笨基吡啶）銥]作為電場發光 掺雜劑之外，根據實關1所迷之相同方法製造咖裝置。 結果，於電壓6.7V有4.〇mA/cm2之電流流動，且證 實發出1090 cd/m2之綠光。 [實施例5] 95084 29 201130805 除了於電場發光層上改成使用化合物35作為主體材 料以及使用Ir(ppy)3 [參（2-笨基咄啶）銥]作為電場發光 摻雜劑之外’根據實施例1所述之相同方法製造0LED裝置。 結果’於電壓6· 8V有4. 0 mA/cm2之電流流動，且證 實發出1120 cd/m2之綠光。 _ [比較例1 ] 除了於真空氣相沉積裝置之小室中改成使用4,4,〜雙 (咔唑-9-基）聯苯（CBP)代替本發明之化合物作為主體材 料’以及令雙（2-甲基-8-經基啥琳基）（對苯基盼基）紹⑴^ (BAlq)作為電洞阻擋層之外，使用與實施例丨及2之相 方法製造0LED裝置。 目5 且證 結果，於電壓7.5V有3.8 mA/cm2之電流流動 實發出1000 cd/m2之綠光。 與傳統材料相比，本發明之有機電場發光化合物具 優異之性質。此外’使財發明之有機電料光化合物 為主體材料的裝置具有優異之電場發光性質以及下降之。 動電壓，從而增加功率效率以及降低功率耗槓。 驅 【圖式簡單說明】 無 【主要元件符號說明】 無 95084 30Liq) After the electron injection layer, another vacuum vapor deposition apparatus was used to form an aluminum (A1) cathode having a thickness of 150 nm to fabricate a ruthenium LED. Each of the compounds used in the OLED was purified by vacuum sublimation at 1 〇 -6 t rr. As a result, a current of 4.1 mA (cm)/cm 2 was flown at the electric power of 6. 7 V, and it was confirmed that green light of 1308 cd/m 2 was emitted. [Example 2] Example 1 was carried out except that the compound 19 was used as a host material on the electroluminescent layer and Ir(ppy) 3 [parameter (2_phenylpyridine) ruthenium] was used as an electric field luminescent dopant. The same method described is used to manufacture an OLED device. As a result, a current of 4. 0 mA/cm 2 was flowed at a voltage of 6.8 V, and it was confirmed that green light of 1210 cd/m 2 was emitted. [Example 3] Except that the electroluminescent layer was changed to use Compound 21 as a host material and Ir(ppy) 3 [参(2-phenyl acridine) oxime] was used as an electric field luminescent dopant, according to Examples The same method as described in 1 manufactures an OLED device. As a result, a current of 3. 8 mA/cm 2 was flowed at a voltage of 7.0 V, and a green light of 1225 cd/m 2 was confirmed. [Example 4] Except that the compound 30 was used as a host material on the electroluminescent layer and Ir(ppy) 3 [substituted (2-phenylidene pyridine) ruthenium] was used as an electric field luminescent dopant, The same method is used to make a coffee maker. As a result, a current of 4. mA/cm 2 flowed at a voltage of 6.7 V, and it was confirmed that green light of 1090 cd/m 2 was emitted. [Example 5] 95084 29 201130805 In addition to the use of the compound 35 as a host material on the electroluminescent layer and the use of Ir(ppy)3 [substituting (2-styl acridine)] as an electric field luminescent dopant] An OLED device was fabricated in the same manner as described in Example 1. As a result, a current of 4. 0 mA/cm 2 was flowed at a voltage of 6.8 V, and a green light of 1120 cd/m 2 was confirmed. _ [Comparative Example 1] In addition to the use of 4,4,~bis(carbazol-9-yl)biphenyl (CBP) in place of the compound of the present invention as a host material in the chamber of a vacuum vapor deposition apparatus, and (2-Methyl-8-pyridyl) (p-phenylphenyl) (1) (BAlq) was used as a hole barrier layer, and an OLED device was produced using the phase method of Examples 2 and 2. The result is that a current of 3.8 mA/cm2 flows at a voltage of 7.5 V and emits green light of 1000 cd/m2. The organic electroluminescent compound of the present invention has excellent properties as compared with conventional materials. Further, the apparatus for making the organic electro-optic compound as a host material of the invention has excellent electric field luminescent properties and a decrease. Dynamic voltage, thereby increasing power efficiency and reducing power consumption. Drive [Simple diagram description] None [Main component symbol description] None 95084 30
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100957288B1 (en) * | 2002-03-15 | 2010-05-12 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent device and organic electroluminescent device using same |
| CN1934906A (en) * | 2004-03-19 | 2007-03-21 | 出光兴产株式会社 | organic electroluminescent element |
| CN101641340B (en) * | 2007-03-26 | 2012-10-17 | 新日铁化学株式会社 | Compound for organic electroluminescent device and organic electroluminescent device |
| JP4776639B2 (en) * | 2008-01-18 | 2011-09-21 | 三井化学株式会社 | Pyridine derivative and organic electroluminescent device containing the same |
| DE102009023155A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
-
2009
- 2009-12-11 KR KR1020090123174A patent/KR20110066494A/en not_active Ceased
-
2010
- 2010-11-22 WO PCT/KR2010/008245 patent/WO2011071255A1/en not_active Ceased
- 2010-12-13 TW TW099143434A patent/TW201130805A/en unknown
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| US9954180B2 (en) | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
| US11316113B2 (en) | 2010-08-20 | 2022-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12464945B2 (en) | 2010-08-20 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN104066728A (en) * | 2011-11-18 | 2014-09-24 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescence compounds and organic electroluminescence device comprising the same |
| CN110256412A (en) * | 2019-06-27 | 2019-09-20 | 上海天马有机发光显示技术有限公司 | A kind of compound, organic electroluminescence device and display device |
| US11498910B2 (en) | 2019-06-27 | 2022-11-15 | Wuhan Tianma Micro-Electronics Co., Ltd. | Compound, organic electroluminescent device and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110066494A (en) | 2011-06-17 |
| WO2011071255A1 (en) | 2011-06-16 |
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