CN101087759A - 蒽衍生物以及使用该衍生物的有机电致发光元件 - Google Patents
蒽衍生物以及使用该衍生物的有机电致发光元件 Download PDFInfo
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- CN101087759A CN101087759A CNA2005800442114A CN200580044211A CN101087759A CN 101087759 A CN101087759 A CN 101087759A CN A2005800442114 A CNA2005800442114 A CN A2005800442114A CN 200580044211 A CN200580044211 A CN 200580044211A CN 101087759 A CN101087759 A CN 101087759A
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- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- GLCGEJFIZRSXBL-UHFFFAOYSA-N dodeca-1,3,5,7,9,11-hexaene Chemical compound C=CC=CC=CC=CC=CC=C GLCGEJFIZRSXBL-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
本发明涉及具有包含含氮六元环的杂芳基且具有特定结构的蒽衍生物,还涉及一种有机电致发光元件,其中在阴极和阳极间挟持有至少具有发光层的由一层或多层组成的有机薄膜层,该有机薄膜层的至少一层中,单独或者作为混合物的成分含有上述蒽衍生物。通过本发明可以提供经过长时间后仍可获得均匀发光的寿命长的有机电致发光元件以及用于制备所述有机电致发光元件的蒽衍生物。
Description
技术领域
本发明涉及蒽衍生物以及使用该衍生物的有机电致发光元件,特别涉及经过长时间后仍可获得均匀发光的寿命长的有机电致发光元件以及用于实现该元件的蒽衍生物。
背景技术
有机电致发光(EL)元件为一种自发发光元件,所利用的是在施加电场时,荧光物质基于从阳极注入的空穴和从阴极注入的电子的复合能而发光的原理。自从Eastman Kodak社的C.W.Tang等人(C.W.Tang,S.A.Vanslyke,Applied Physics Letters,第51卷,第913页,1987年等)报导了利用层压型元件的低电压驱动有机EL元件以来,有关把有机材料作为结构材料的有机EL元件的研究方兴未艾。Tang等人将三(8-羟基喹啉)铝用于发光层,将三苯基二胺衍生物用于空穴输送层。作为层压结构的优势,可列举能提高将空穴注入发光层的效率、提高通过阻断并复合从阴极注入的电子形成激子的生成效率、可将发光层中形成的激子封闭起来。作为这种例子的有机EL元件的元件结构,熟知的是空穴输送(注入)层、电子输送发光层的两层型结构或者空穴输送(注入)层、发光层、电子输送(注入)层的三层型结构等。关于这种层压型元件,为了提高所注入的空穴和电子的复合效率,对元件结构及形成方法进行了研究。
作有机EL元件的发光材料,已知三(8-羟基喹啉)铝配位化合物等螯合物、香豆素衍生物、四苯基丁二烯衍生物、双苯乙烯基亚芳基衍生物和二唑衍生物等发光材料,并且已经公开了可由上述发光材料获得蓝色至红色的可见光区内的发光,有望制备彩色显示元件(例如,参考专利文献1-3)。
另外,近年来,进行了在有机EL元件上设置电子注入层以提高发光效率的尝试。但是,存在如下缺点:观察到受激态配位化合物(exciplex)的形成,或者虽然获得高亮度的发光,但是发光寿命短。此外,长时间通电时,金属电极和有机层产生剥离,或者有机层和电极发生结晶化并混浊而使发光亮度降低,从而有必要防止这种现象产生。作为解决这种问题的尝试,在专利文献4中,记载了使用吡嗪化合物、喹啉化合物、喹喔啉化合物,例如2,3,5,6-四苯基吡嗪、2,3,4-三苯基喹啉、2,3-二苯基喹喔啉作为有机EL元件的构成成分的方案。但是,由于这些化合物熔点低,存在即使用作有机EL元件的非晶薄膜层也会立刻产生晶体,几乎不会发光的问题。另外,还存在金属电极和有机层因通电产生剥离,有机EL元件寿命变短的问题。
专利文献1:特开平8-239655号公报
专利文献2:特开平7-183561号公报
专利文献3:特开平3-200289号公报
专利文献4:美国专利第5077142号说明书
发明内容
本发明是为了解决上述课题而提出的,目的在于提供经过长时间后仍可获得均匀发光的寿命长的有机电致发光元件以及用于制备所述有机电致发光元件的蒽衍生物。
本发明者等为了实现上述目的进行了反复研究,结果发现通过把具有包含含氮六元环的杂芳基并且具有特定结构的蒽衍生物用作有机EL元件用材料,能够实现上述目的,从而完成了本发明。
即,本发明提供了下述通式(1)或(2)所示的蒽衍生物。
(式中,R1-R3分别独立地表示氢原子、卤原子、取代或未取代的碳原子数1-40的脂肪族烃基、取代或未取代的碳原子数5-60的芳基、或者取代或未取代的碳原子数3-60的杂芳基。其中,R1和R2同时为氢原子的情况不存在。
L1-L3分别独立地表示单键、取代或未取代的碳原子数1-40的二价脂肪族烃基、取代或未取代的碳原子数5-60的亚芳基、或者取代或未取代的碳原子数3-60的亚杂芳基。
Har表示含有含氮六元环的取代或未取代的碳原子数3-60的杂芳基。)
另外,本发明提供了一种有机电致发光元件,其中在阴极和阳极间挟持有至少具有发光层的由一层或多层组成的有机薄膜层,该有机薄膜层的至少一层中,单独或者作为混合物的成分含有本发明的蒽衍生物。
发明效果
本发明的蒽衍生物以及使用它的有机EL元件经过长时间后仍可获得均匀发光,寿命长。
具体实施方式
本发明的蒽衍生物是下述通式(1)或(2)所示的蒽衍生物。
通式(1)或(2)中,R1-R3优选独立地是氢原子、卤原子、取代或未取代的碳原子数1-40的脂肪族烃基、取代或未取代的碳原子数5-60的芳基、或者取代或未取5的碳原子数3-60的杂芳基。
其中,R1和R2同时为氢原子的情况不存在。
作为R1-R3的卤原子,可列举例如氟、氯、溴、碘等。
作为R1-R3的取代或未取代的碳原子数1-40的脂肪族烃基,可列举碳原子数1-40的烷基、碳原子数2-40的烯基、碳原子数2-40的炔基等。例如,作为烷基,可列举甲基、乙基、1-丙基、2-丙基、1-丁基、2-丁基、仲丁基、叔丁基、戊基、己基、辛基、癸基、十二烷基、2-乙基己基、3,7-二甲基辛基、环丙基、环戊基、环己基、1-金刚烷基、2-金刚烷基、降冰片烷基、三氟甲基、三氯甲基等,优选为甲基、乙基、1-丙基、2-丙基、1-丁基、2-丁基、仲丁基、叔丁基,作为烯基,可列举乙烯基、丙烯基、丁烯基、油烯基、二十碳五烯基(eicosapentaenyl)、二十二碳六烯基(docosahexaenyl)等,优选乙烯基、丙烯基,作为炔基,可列举乙炔基、甲基乙炔基等,优选乙炔基。
作为上述脂肪族烃基的取代基,可列举例如芳基(优选碳原子数为6-30,更优选碳原子数为6-20,特别优选碳原子数为6-12,可列举例如苯基、对甲基苯基、萘基等)、氨基(优选碳原子数为0-20,更优选碳原子数为0-12,特别优选碳原子数为0-6,可列举例如氨基、甲基氨基、二甲基氨基、二乙基氨基、二苯基氨基、二苄基氨基等)、烷氧基(优选碳原子数为1-20,更优选碳原子数为1-12,特别优选碳原子数为1-8,可列举例如甲氧基、乙氧基、丁氧基等)、芳氧基(优选碳原子数为6-20,更优选碳原子数为6-16,特别优选碳原子数为6-12,可列举例如苯氧基、2-萘氧基等)、酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如乙酰基、苯甲酰基、甲酰基、特戊酰基等)、烷氧基羰基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-12,可列举例如甲氧基羰基、乙氧基羰基等)、芳氧基羰基(优选碳原子数为7-20,更优选碳原子数为7-16,特别优选碳原子数为7-10,可列举例如苯氧基羰基等)、酰氧基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-10,可列举例如乙酰氧基、苯甲酰氧基等)、酰基氨基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-10,可列举例如乙酰基氨基、苯甲酰基氨基等)、烷氧基羰基氨基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-12,可列举例如甲氧基羰基氨基等)、芳氧基羰基氨基(优选碳原子数为7-20,更优选碳原子数为7-16,特别优选碳原子数为7-12,可列举例如苯氧基羰基氨基等)、磺酰基氨基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲磺酰基氨基、苯磺酰基氨基等)、氨磺酰基(优选碳原子数为0-20,更优选碳原子数为0-16,特别优选碳原子数为0-12,可列举例如氨磺酰基、甲基氨磺酰基、二甲基氨磺酰基、苯基氨磺酰基等)、氨基甲酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如氨基甲酰基、甲基氨基甲酰基、二乙基氨基甲酰基、苯基氨基甲酰基等)、烷硫基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲硫基、乙硫基等)、芳硫基(优选碳原子数为6-20,更优选碳原子数为6-16,特别优选碳原子数为6-12,可列举例如苯硫基等)、磺酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲磺酰基、甲苯磺酰基等)、亚磺酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲烷亚磺酰基、苯亚磺酰基等)、脲基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如酰脲基、甲脲基、苯基脲基等)、磷酸酰胺基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如二乙基磷酸酰胺基、苯基磷酸酰胺基等)、羟基、巯基、卤原子(例如氟原子、氯原子、溴原子、碘原子)、氰基、磺基、羧基、硝基、羟肟酸、亚磺基、肼基、亚氨基、杂环基(优选碳原子数为1-30,更优选碳原子数为1-12,作为杂原子,例如包括氮原子、氧原子、硫原子,具体地可列举例如咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、吗啉基、苯并唑基、苯并咪唑基、苯并噻唑基、咔唑基等)、甲硅烷基(优选碳原子数为3-40,更优选碳原子数为3-30,特别优选碳原子数为3-24,可列举例如三甲基甲硅烷基、三苯基甲硅烷基等)等。这些取代基还可以再被取代。另外,当取代基是两个以上时,可以相同也可以不同。此外,在可能的情况下也可以彼此连接形成环。
作为R1-R3的取代或未取代的碳原子数5-60的芳基,可列举例如苯基、2-联苯基、3-联苯基、4-联苯基、三联苯基、3,5-二苯基苯基、3,4-二苯基苯基、五苯基苯基、芴基、1-萘基、2-萘基、9-蒽基、2-蒽基、9-菲基、1-芘基、
基、并四苯基、coronyl、10-苯基-蒽-9-基、10-萘-2-基-蒽-9-基、12-苯基-
-6-基、(10-苯基-蒽-9-基)-4-苯基、(10-萘基-2-基-蒽-9-基)-4-苯基、芴基、9,9’-二甲基芴-2-基、螺芳香环基等。
作为螺芳香环基,优选下述通式(A)表示的化合物,
(Ra和Rb分别独立地表示氢原子、取代或未取代的氨基、取代或未取代的碳原子数1-50的烷基、取代或未取代的碳原子数6-40的芳基或者取代或未取代的碳原子数5-40的杂环基,Rc表示形成环状结构的原子团。L是单键、-O-、-S-、-NR’-或者-CR”R-(R’、 R”和R分别独立地是取代或未取代的碳原子数1-50的烷基或者取代或未取代的碳原子数6-40的芳基)。s、q和r分别是0-2的整数。Ra和Rb也可以彼此结合形成环)
例如,可列举螺(环己烷-1,9’-芴)-2’-基、螺(环戊烷-1,9’-芴)-2’-基、螺(茚-1,9’-芴)-2’-基、二螺(双芴-9,10,9’, 9”-9,9,10,10-四氢蒽)-2-基、二螺(双芴-9,10,9’,9”-9,9,10,10-四氢蒽)-2’-基、9,9’-螺联芴-2-基等。
作为上述芳基的取代基,可列举例如烷基(优选碳原子数为1-20,更优选碳原子数为1-12,特别优选碳原子数为1-8,可列举例如甲基、乙基、异丙基、叔丁基、正辛基、正癸基、正十六烷基、环丙基、环戊基、环己基等)、烯基(优选碳原子数为2-20,更优选碳原子数为2-12,特别优选碳原子数为2-8,可列举例如乙烯基、烯丙基、2-丁烯基、3-戊烯基等)、炔基(优选碳原子数为2-20,更优选碳原子数为2-12,特别优选碳原子数为2-8,可列举例如丙炔基、3-戊炔基等)、氨基(优选碳原子数为0-20,更优选碳原子数为0-12,特别优选碳原子数为0-6,可列举例如氨基、甲基氨基、二甲基氨基、二乙基氨基、二苯基氨基、二苄基氨基等)、烷氧基(优选碳原子数为1-20,更优选碳原子数为1-12,特别优选碳原子数为1-8,可列举例如甲氧基、乙氧基、丁氧基等)、芳氧基(优选碳原子数为6-20,更优选碳原子数为6-16,特别优选碳原子数为6-12,可列举例如苯氧基、2-萘氧基等)、酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如乙酰基、苯甲酰基、甲酰基、特戊酰基等)、烷氧基羰基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-12,可列举例如甲氧基羰基、乙氧基羰基等)、芳氧基羰基(优选碳原子数为7-20,更优选碳原子数为7-16,特别优选碳原子数为7-10,可列举例如苯氧基羰基等)、酰氧基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-10,可列举例如乙酰氧基、苯甲酰氧基等)、酰基氨基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-10,可列举例如乙酰基氨基、苯甲酰基氨基等)、烷氧基羰基氨基(优选碳原子数为2-20,更优选碳原子数为2-16,特别优选碳原子数为2-12,可列举例如甲氧基羰基氨基等)、芳氧基羰基氨基(优选碳原子数为7-20,更优选碳原子数为7-16,特别优选碳原子数为7-12,可列举例如苯氧基羰基氨基等)、磺酰基氨基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲磺酰基氨基、苯磺酰基氨基等)、氨磺酰基(优选碳原子数为0-20,更优选碳原子数为0-16,特别优选碳原子数为0-12,可列举例如氨磺酰基、甲基氨磺酰基、二甲基氨磺酰基、苯基氨磺酰基等)、氨基甲酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如氨基甲酰基、甲基氨基甲酰基、二乙基氨基甲酰基、苯基氨基甲酰基等)、烷硫基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲硫基、乙硫基等)、芳硫基(优选碳原子数为6-20,更优选碳原子数为6-16,特别优选碳原子数为6-12,可列举例如苯硫基等)、磺酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲磺酰基、甲苯磺酰基等)、亚磺酰基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如甲亚磺酰基、苯亚磺酰基等)、脲基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如脲基、甲脲基、苯基脲基等)、磷酸酰胺基(优选碳原子数为1-20,更优选碳原子数为1-16,特别优选碳原子数为1-12,可列举例如二乙基磷酸酰胺基、苯基磷酸酰胺基等)、羟基、巯基、卤原子(例如氟原子、氯原子、溴原子、碘原子)、氰基、磺基、羧基、硝基、羟肟酸、亚磺基、肼基、亚氨基、杂环基(优选碳原子数为1-30,更优选碳原子数为1-12,作为杂原子,例如包括氮原子、氧原子、硫原子,具体地可列举例如咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、吗啉基、苯并唑基、苯并咪唑基、苯并噻唑基、咔唑基等)、甲硅烷基(优选碳原子数为3-40,更优选碳原子数为3-30,特别优选碳原子数为3-24,可列举例如三甲基甲硅烷基、三苯基甲硅烷基等)等。这些取代基还可以再被取代。另外,当取代基是两个以上时,可以相同也可以不同。此外,在可能的情况下也可以彼此连接形成环。
作为R1-R3的取代或未取代的碳原子数3-60的杂芳基,可列举例如呋喃、噻吩、吡咯、咪唑、吡唑、三唑、二唑、吡啶、吡嗪、三嗪、嘧啶、苯并呋喃、二苯并呋喃、苯并噻吩、二苯并噻吩、咔唑、苯并咪唑、咪唑并吡啶等一价的残基。
另外,作为上述杂芳基的取代基,可列举与上述芳基的取代基相同的取代基。
通式(1)和(2)中,L1-L3分别独立地表示单键、取代或未取代的碳原子数1-40的二价脂肪族烃基、取代或未取代的碳原子数5-60的亚芳基、或者取代或未取代的碳原子数3-60的亚杂芳基。
作为L1-L3的取代或未取代的碳原子数1-40的二价脂肪族烃基,可列举例如亚甲基、亚丙基、亚丁基、亚乙烯基、亚乙炔基等,优选为亚甲基。作为该脂肪族烃基的取代基,可列举与上述R1-R3的脂肪族烃基的取代基相同的取代基。
作为L1-L3的取代或未取代的碳原子数5-60的亚芳基,可列举例如亚苯基、亚萘基、亚蒽基、亚联苯基、亚三联苯基、亚芘基、亚
基、亚芴基、亚螺芴基等,优选为亚苯基。作为该亚芳基的取代基,可列举与上述R1-R3的芳基的取代基相同的取代基。
作为L1-L3的取代或未取代的碳原子数3-60的亚杂芳基,可列举例如噻吩、呋喃、硒吩、吡啶、吡嗪、嘧啶、二唑、噻二唑、唑、噻唑、三唑等的二价残基,优选为噻吩、吡啶、二唑、三唑的二价残基。作为该亚杂芳基的取代基,可列举与上述R1-R3的芳基的取代基相同的取代基。
通式(1)和(2)中,作为HAr的含有含氮六元环的取代或未取代的碳原子数3-60的杂芳基,可列举例如吡啶、吡嗪、三嗪、嘧啶、喹喔啉、喹唑啉、喹啉、菲绕啉等的一价残基,优选为下式表示的基团。
(式中,R4-R6分别独立地表示氢原子、卤原子、取代或未取代的碳原子数1-40的脂肪族烃基、取代或未取代的碳原子数5-60的芳基、或者取代或未取代的碳原子数3-60的杂芳基,作为这些基团的具体例,可列举与上述R1-R3中列举的基团相同的取代基。
另外,多个相邻的R4、R5也可以结合形成环状结构,作为环状结构,可列举例如环丁烷、环戊烷、环己烷、金刚烷、降冰片烷等碳原子数4-12的环烷烃,环丁烯、环戊烯、环己烯、环庚烯、环辛烯等碳原子数4-12的环烯烃,环己二烯、环庚二烯、环辛二烯等碳原子数6-12的环二烯,苯、萘、菲、蒽、芘、
苊等碳原子数6-50的芳香族环等。
a表示0-4的整数,b表示0-3的整数,c表示0-2的整数。)
另外,作为上述杂芳基的取代基,可列举与上述R1-R3的芳基的取代基相同的取代基。
本发明的蒽衍生物可以用作有机EL元件用材料,特别可以用作有机EL元件用电子注入·输送材料和电子照相感光体的电子输送材料,优选用作有机EL元件用材料。
本发明通式(1)或(2)所示的蒽衍生物的具体例子如下所示,但是并不限于这些化合物。
下面,对本发明的有机EL元件进行说明。
本发明的有机EL元件中,在阴极和阳极间挟持有至少具有发光层的由一层或多层组成的有机薄膜层,该有机薄膜层的至少一层中,单独或者作为混合物的成分含有本发明的上述蒽衍生物。
本发明的有机EL元件中,优选主要在发光带区域含有上述蒽衍生物,更优选在发光层中含有上述蒽衍生物。
另外,本发明的有机EL元件的上述发光层中,除了含有本发明的蒽衍生物以外,还可以含有荧光性或者磷光性的掺杂剂。
作为上述荧光性的掺杂剂,优选芳胺化合物和/或苯乙烯基胺化合物。
作为苯乙烯基胺化合物,优选以下通式(B)表示的化合物。
(式中,Ar3是选自苯基、联苯基、三联苯基、茋基和二苯乙烯基芳基的基团;Ar4和Ar5各自独立是氢原子或碳原子数6-20的芳香族基;Ar3-Ar5可以被取代;p’是1-4的整数。还优选Ar4或Ar5至少一个被苯乙烯基取代。)
其中,作为碳原子数6-20的芳香族基,可列举苯基、萘基、蒽基、菲基、三联苯基等。
作为上述芳胺化合物,优选以下通式(C)表示的化合物。
(式中,Ar6-Ar8是取代或未取代的环碳原子数5-40的芳基。q’是1-4的整数。)
其中,作为环碳原子数5-40的芳基,可列举例如苯基、萘基、
基、并四苯基、蒽基、菲基、芘基、蔻基(coronyl)、联苯基、三联苯基、吡咯基、呋喃基、噻吩基、苯并噻吩基、二唑基、二苯基蒽基、吲哚基、咔唑基、吡啶基、苯并喹啉基、荧蒽基、苊并荧蒽基、茋基等。另外,作为该芳基的优选取代基,可列举碳原子数1-6的烷基(乙基、甲基、异丙基、正丙基、仲丁基、叔丁基、戊基、己基、环戊基、环己基等)、碳原子数1-6的烷氧基(乙氧基、甲氧基、异丙氧基、正丙氧基、仲丁氧基、叔丁氧基、戊氧基、己氧基、环戊氧基、环己氧基等)、环碳原子数5-40的芳基、被环碳原子数5-40的芳基取代的氨基、包含环碳原子数5-40的芳基的酯基、包含碳原子数1-6的烷基的酯基、氰基、硝基、卤原子等。
另外,作为上述磷光性的掺杂剂,可列举金属配位化合物,优选为含有选自Ir、Ru、Pd、Pt、Os和Re中的至少一种金属的金属配位化合物,配位基优选具有选自苯基吡啶骨架、联吡啶基骨架和菲绕啉骨架的至少一种骨架。这种金属配位化合物的具体例子可以举出三(2-苯基吡啶)铱、三(2-苯基吡啶)钌、三(2-苯基吡啶)钯、双(2-苯基吡啶)铂、三(2-苯基吡啶)锇、三(2-苯基吡啶)铼、八乙基铂卟啉、八苯基铂卟啉、八乙基钯卟啉、八苯基钯卟啉等,但是并不限于这些,可从所要求的发光色、元件性能、与基质化合物的关系出发选择合适的配位化合物。
另外,本发明的有机EL元件中,上述有机薄膜层可以具有空穴注入层和/或空穴输送层,而且该空穴注入层和/或空穴输送层单独或作为混合物成分含有本发明的蒽衍生物,另外也可以是上述有机薄膜层具有电子注入层和/或电子输送层,而且该电子注入层和/或电子输送层单独或作为混合物成分含有本发明的蒽衍生物。
下面,对本发明有机EL元件的元件结构进行说明。
作为本发明有机EL元件的代表性元件结构,可列举如下。
(1)阳极/发光层/阴极;
(2)阳极/空穴注入层/发光层/阴极;
(3)阳极/发光层/电子注入层/阴极;
(4)阳极/空穴注入层/发光层/电子注入层/阴极;
(5)阳极/有机半导体层/发光层/阴极;
(6)阳极/有机半导体层/电子阻挡层/发光层/阴极;
(7)阳极/有机半导体层/发光层/粘着改善层/阴极;
(8)阳极/空穴注入层/空穴输送层/发光层/电子注入层/阴极;
(9)阳极/绝缘层/发光层/绝缘层/阴极;
(10)阳极/无机半导体层/绝缘层/发光层/绝缘层/阴极;
(11)阳极/有机半导体层/绝缘层/发光层/绝缘层/阴极;
(12)阳极/绝缘层/空穴注入层/空穴输送层/发光层/绝缘层/阴极;
(13)阳极/绝缘层/空穴注入层/空穴输送层/发光层/电子注入层/阴极。
其中,通常优选使用(8)的结构,但是,并不限于这些结构。
本发明的蒽衍生物可以用于有机EL元件的任一有机薄膜层中,也可以用于发光带区域或电子输送带区域中,优选用于电子输送带区域中,特别优选用于电子注入·输送层中,由此可以使分子难以结晶,提高制造有机EL元件时的合格率。
作为本发明的蒽衍生物在有机薄膜层中的含量优选为30-100%摩尔。
(2)透光性基板
本发明的有机EL元件是在透光性基板上制作。其中所述的透光性基板是支撑有机EL元件的基板,优选在400-700nm的可见光区内的光透过率为50%以上的平滑的基板。
具体地,可列举玻璃板、聚合物板。作为玻璃板,特别列举钙钠玻璃、含钡和锶的玻璃、铅玻璃、铝硅酸玻璃、硼硅酸玻璃、钡硼硅酸玻璃、石英等。另外,作为聚合物玻璃板,可列举聚碳酸酯、丙烯酸类树脂、聚对苯二甲酸乙二酯、聚醚硫化物、聚砜等。
(3)阳极
本发明的有机EL元件的阳极具有将空穴注入到空穴输送层或注入发光层的功能,有效的是具有4.5eV以上功函数的。作为用于本发明的阳极材料的具体例子,可列举氧化铟锡合金(ITO)、氧化铟锌合金(IZO)、氧化锡(NESA)、金、银、铂、铜等。
阳极可以通过将这些电极物质采用蒸镀法或溅射法等方法形成薄膜来制备。
当如上所述地从阳极取出从发光层发出的光时,优选阳极的光透过率大于10%。另外,优选阳极的片材电阻率为数百Ω/□以下。阳极的膜厚根据材料而有所不同,通常选择为10nm-1μm,优选10-200nm。
(4)发光层
有机EL元件的发光层同时具有以下(1)-(3)的功能:
(1)注入功能:当施加电场时,可以从阳极或空穴注入层注入空穴,从阴极或电子注入层注入电子的功能;
(2)传输功能:在电场力的作用下,传输已注入的电荷(电子和空穴)的功能;和
(3)发光功能:提供电子和空穴复合的场所,并基于此发光的功能。
其中,在注入空穴的容易程度和注入电子的容易程度方面可以存在区别,另外,也可以在用空穴和电子的迁移率表示的输送能力方面存在大小之分,但是优选能够传输其中任一电荷。
作为形成发光层的方法,可适宜使用例如蒸镀法、旋涂法、LB法等公知的方法。发光层特别优选为分子沉积薄膜。其中所述分子沉积薄膜是由气相状态的材料化合物沉积形成的薄膜,或者由溶液状态或液相状态的材料化合物进行固体化形成的薄膜,通常该分子沉积薄膜与由LB法形成的薄膜(分子累积膜)可以根据凝集结构和高次结构的差异或由这些引起的功能差异进行区分。
另外,还可以如特开昭57-51781号公报所公开的那样,通过将树脂等粘合剂和材料化合物溶解于溶剂中形成溶液,随后将其用旋涂法等进行薄膜化,来形成发光层。
本发明中,在不损害本发明目的的范围内,可以根据需要在发光层中含有除本发明的蒽衍生物以外的其它公知的发光材料,另外,也可以在含有本发明的蒽衍生物的发光层上层叠含有其它公知的发光材料的发光层。
(5)空穴注入/输送层
空穴注入/输送层是帮助空穴向发光层的注入,输送至发光区的层,空穴迁移率高,并且电离能通常较小,为5.5eV以下。作为这样的空穴注入/输送层,优选在较低的电场强度下可将空穴输送至发光层的材料,进一步优选例如在施加104-106V/cm的电场时,其空穴的迁移率至少为10-4cm2/V·s的材料。
当将本发明的蒽衍生物用于空穴输送带区域时,本发明的蒽衍生物可以单独形成空穴注入/输送层,也可以与其它的材料混合使用。
作为与本发明的蒽衍生物混合形成空穴注入/输送层的材料,只要是具有上述优选的性质的材料,就没有特别限制,可以从现有光传导材料中作为空穴的电荷输送材料常用的材料和有机EL元件的空穴注入/输送层中使用的公知的材料中选择任意的材料来使用。
作为具体例子,可列举三唑衍生物(参阅美国专利3,112,197号说明书等)、噁二唑衍生物(参阅美国专利3,189,447号说明书等)、咪唑衍生物(参阅特公昭37-16096号公报等)、多芳基链烷烃衍生物(参阅美国专利3,615,402号说明书、同第3,820,989号说明书、同第3,542,544号说明书、特公昭45-555号公报、同51-10983号公报、特开昭51-93224号公报、同55-17105号公报、同56-4148号公报、同55-108667号公报、同55-156953号公报、同56-36656号公报等)、吡唑啉衍生物及吡唑啉酮衍生物(参阅美国专利第3,180,729号说明书、同第4,278,746号说明书、特开昭55-88064号公报、同55-88065号公报、同49-105537号公报、同55-51086号公报、同56-80051号公报、同56-88141号公报、同57-45545号公报、同54-112637号公报、同55-74546号公报等)、苯二胺衍生物(参阅美国专利第3,615,404号说明书、特公昭51-10105号公报、同46-3712号公报、同47-25336号公报、特开昭54-53435号公报、同54-110536号公报、同54-119925号公报等)、芳胺衍生物(参阅美国专利第3,567,450号说明书、同第3,180,703号说明书、同第3,240,597号说明书、同第3,658,520号说明书、同第4,232,103号说明书、同第4,175,961号说明书、同第4,012,376号说明书、特公昭49-35702号公报、同39-27577号公报、特开昭55-144250号公报、同56-119132号公报、同56-22437号公报、西德专利第1,110,518号说明书等)、氨基取代查耳酮衍生物(参阅美国专利第3,526,501号说明书等)、噁唑衍生物(美国专利第3,257,203号说明书等中公开的物质)、苯乙烯蒽衍生物(参阅特开昭56-46234号公报等)、芴酮衍生物(参阅特开昭54-110837号公报等)、腙衍生物(参阅美国专利第3,717,462号说明书、特开昭54-59143号公报、同55-52063号公报、同55-52064号公报、同55-46760号公报、同55-85495号公报、同57-11350号公报、同57-148749号公报、特开平2-311591号公报等)、茋衍生物(参阅特开昭61-210363号公报、同第61-228451号公报、同61-14642号公报、同61-72255号公报、同62-47646号公报、同62-36674号公报、同62-10652号公报、同62-30255号公报、同60-93455号公报、同60-94462号公报、同60-174749号公报、同60-175052号公报等)、硅氮烷衍生物(美国专利第4,950,950号说明书)、聚硅烷类(特开平2-204996号公报)、苯胺类共聚物(特开平2-282263号公报)、特开平1-211399号公报公开的导电性高分子低聚物(特别是噻吩低聚物)等。
作为空穴注入/输送层的材料可以使用上述的物质,但是优选使用卟啉化合物(特开昭63-2956965号公报等公开的物质)、芳香族叔胺化合物及苯乙烯胺化合物(参阅美国专利第4,127,412号说明书、特开昭53-27033号公报、同54-58445号公报、同54-149634号公报、同54-64299号公报、同55-79450号公报、同55-144250号公报、同56-119132号公报、同61-295558号公报、同61-98353号公报、同63-295695号公报等),特别优选使用芳香族叔胺化合物。
还可以例举美国专利第5,061,569号中记载的分子内具有2个缩合芳香环的,例如4,4’-双(N-(1-萘基)-N-苯基胺基)联苯(以下缩写为NPD),还有特开平4-308688号公报记载的3个三苯胺单元连结成了星爆(starburst)型的4,4’,4”-三(N-(3-甲基苯基)-N-苯基胺基)三苯胺(以下缩写为MTDATA)等。
进而,除了作为发光层材料所示过的上述芳香族二亚甲基类化合物以外,p型Si、p型SiC等无机化合物也可以用作空穴注入/输送层的材料。
空穴注入/输送层可以通过将本发明的蒽衍生物或上述化合物用例如真空蒸镀法、旋涂法、浇注法、LB法等公知的方法进行薄膜化形成。作为空穴注入/输送层的膜厚没有特别限制,通常为5nm-5μm。该空穴注入/输送层在空穴输送带区域含有本发明的蒽衍生物时,可以由上述材料的一种或两种以上构成的一层而构成,上述空穴注入/输送层也可以是将由其它化合物构成的空穴注入/输送层层叠而成的。
另外,也可以设置有机半导体层作为帮助向发光层的空穴注入或电子注入的层,适宜使用具有10-10S/cm以上的电导率的物质。作为这样的有机半导体层的材料,可以使用含噻吩低聚物、特开平8-193191号公报中记载的含芳基胺低聚物等导电性低聚物,含芳基胺树枝状高分子等导电性树枝状高分子等。
(6)电子注入/输送层
电子注入/输送层是帮助电子向发光层的注入,并输送至发光区的层,电子迁移率大,另外,粘着改善层是由该电子注入层中与阴极的粘着性特别好的材料组成的层。作为用于电子注入/输送层的材料,8-羟基喹啉或其衍生物的金属配位化合物较适宜。
作为该8-羟基喹啉或其衍生物的金属配位化合物具体例子,可列举包含喔星(一般为8-羟基喹啉)的螯合物的金属螯合喔星化合物,例如可以使用三(8-羟基喹啉)合铝(Alq)作为电子注入材料。
另外,作为噁二唑衍生物,可列举用下述式表示的电子传递化合物。
(式中,Ar1’,Ar2’Ar3’,Ar5’,Ar6’,Ar9’分别表示取代或未取代的芳基,分别可以相同,也可以不同。另外,Ar4’,Ar7’,Ar8’表示取代或未取代的亚芳基,分别可以相同,也可以不同)
在此,作为芳基,可列举苯基、联苯基、蒽基、苝基、芘基,作为亚芳基,可列举亚苯基、亚萘基、亚联苯基、亚蒽基、亚苝基、亚芘基等。另外,作为取代基可列举碳原子数1-10的烷基、碳原子数1-10的烷氧基或氰基等。该电子传递化合物优选为薄膜形成性的物质。
作为上述电子传递性化合物的具体例,可以例举下述物质。
另外,本发明的有机EL元件优选电子注入层和/或电子输送层中含有还原性掺杂剂,也可以在输送电子的区域或阴极和有机薄膜层的界面区域含有还原性掺杂剂。在此,所谓的还原性掺杂剂是指可以将电子输送性化合物还原的物质。因而,只要是具有一定的还原性的物质,就可使用各种各样的,例如,可以适当地使用选自碱金属、碱土类金属、稀土类金属、碱金属的氧化物、碱金属的卤化物、碱土类金属的氧化物、碱土类金属的卤化物、稀土类金属的氧化物、稀土类金属的卤化物、碱金属的有机配位化合物、碱土类金属的有机配位化合物和稀土类金属的有机配位化合物中的至少一种物质。
作为优选的还原性掺杂剂的具体例子,可列举选自Na(功函数:2.36eV)、K(功函数:2.28eV)、Rb(功函数:2.16eV)及Cs(功函数:1.95eV)中的至少一种碱金属,选自Ca(功函数:2.9eV)、Sr(功函数:2.0-2.5eV)及Ba(功函数:2.52eV)中的至少一种碱土类金属。特别优选功函数为2.9eV以下的物质。这些物质中,更优选的还原性掺杂剂为选自K、Rb及Cs中的至少一种碱金属,进一步优选Rb或Cs,最优选为Cs。这些碱金属的还原能力特别高,通过向电子注入区域的比较少量的添加,可以提高有机EL元件中的发光亮度、延长其寿命。另外,作为功函数为2.9eV以下的还原性掺杂剂,也优选这些两种以上的碱金属的组合,特别优选包含Cs的组合,例如Cs和Na、Cs和K、Cs和Rb或Cs和Na和K的组合。通过包含Cs进行组合,可以有效地发挥其还原能力,通过向电子注入区域的添加,可以提高有机EL元件中的发光亮度、延长其寿命。
本发明的有机EL元件中,可以在阴极和有机层之间进一步设置由绝缘体或半导体构成的电子注入层。由此,可以有效地防止电流的泄漏,提高电子注入性。作为这样的绝缘体,优选使用碱金属硫属化合物、碱土类金属硫属化合物、碱金属的卤化物及碱土类金属的卤化物中的至少一种金属化合物。电子注入层只要是由这些碱金属硫属化合物等构成的,就可以进一步提高电子注入性,故优选。具体来讲,作为优选的碱金属硫属化合物,可列举例如Li2O、LiO、Na2S、Na2Se及NaO,作为优选的碱土类金属硫属化合物,可列举例如CaO、BaO、SrO、BeO、BaS及CaSe。另外,作为优选的碱金属的卤化物,可列举例如LiF、NaF、KF、LiCl、KCl及NaCl等。另外,作为优选的碱土类金属的卤化物,可列举例如CaF2、BaF2、SrF2、MgF2及BeF2等氟化物和氟化物以外的卤化物。
另外,作为构成电子注入层的半导体,可列举例如包含Ba、Ca、Sr、Yb、Al、Ga、In、Li、Na、Cd、Mg、Si、Ta、Sb及Zn中的至少一种元素的氧化物、氮化物或氮氧化物等的单独一种或两种以上的组合。另外,构成电子注入层的无机化合物,优选为微结晶或非晶质的绝缘性薄膜。电子注入层只要是由这些绝缘性薄膜构成的,由于可以形成更均匀的薄膜,因此,可以减少黑点等图像缺陷。另外,作为这样的无机化合物,可列举例如上述的碱金属硫属化合物、碱土类金属硫属化合物、碱金属的卤化物及碱土类金属的卤化物等。
(7)阴极
作为阴极,为了将电子注入到电子注入/输送层或者发光层,使用功函数小的(4eV以下)金属、合金、电传导性化合物或这些的混合物作为电极物质。作为这种电极物质的具体例子,可列举钠、钠-钾合金、镁、锂、镁-银合金、铝/氧化铝、铝-锂合金、铟、稀土金属等。
该阴极可以通过将这些电极物质用蒸镀法和溅射法等方法形成薄膜来制备。
其中,当从阴极取也从发光层发出的光时,优选阴极的光透过率大于10%。
还优选阴极的片材电阻率为数百Ω/□以下,膜厚通常为10nm-1μm,优选50-200nm。
(8)绝缘层
由于对超薄薄膜施加电场,有机EL元件易因漏电和短路而产生象素缺陷。为了防止形成这些缺陷,优选在一对电极之间插入绝缘性薄膜层。
作为用于绝缘层的材料,可列举例如氧化铝、氟化锂、氧化锂、氟化铯、氧化铯、氧化镁、氟化镁、氧化钙、氟化钙、氮化铝、氧化钛、氧化硅、氧化锗、氮化硅、氮化硼、氧化钼、氧化钌和氧化钒等,还可使用它们的混合物或层叠材料。
(9)有机EL元件的制造方法
通过用上述列举的材料和形成方法形成阳极、发光层、根据需要而设的空穴注入/输送层以及根据需要而设的电子注入/输送层,进而形成阴极,可以制作有机EL元件。也可采用从阴极到阳极的、与上述相反的顺序,制作有机EL元件。
下面,记载了在透光性基板上依次设置阳极/空穴注入层/发光层/电子注入层/阴极的有机EL元件的制作例。
首先,在合适的透光性基板上采用蒸镀法或溅射法等方法形成由阳极材料组成的薄膜,使得所形成的薄膜厚度为1μm以下,优选为10-200nm,从而制作阳极。接着,在该阳极上设置空穴注入层。可采用如上所述的真空蒸镀法、旋涂法、浇铸法、LB法等方法形成空穴注入层,但是从易得到均匀的薄膜,且难以形成针孔等观点考虑,优选用真空蒸镀法形成。当采用真空蒸镀法形成空穴注入层时,该蒸镀条件根据使用的化合物(空穴注入层的材料)、作为目标的空穴注入层的晶体结构和复合结构等的不同而不同,但通常优选在以下范围内适当地选择:蒸镀源的温度50-450℃、真空度10-7-10-3托、蒸镀速率0.01-50nm/s、基板温度:-50℃至300℃、膜厚5nm-5μm。
随后,在空穴注入层上设置发光层时,所述发光层的形成也可以通过使用所需有机发光材料采用真空蒸镀法、溅射法、旋涂法、浇注法等方法将有机发光材料薄膜化来制备,但是从易得到均匀的薄膜,且难以形成针孔等观点考虑,优选用真空蒸镀法形成。当采用真空蒸镀法形成发光层时,该蒸镀条件根据使用的化合物的不同而不同,通常可选择与空穴注入层相同的条件范围。
接着,在该发光层上设置电子注入层。与空穴注入层和发光层相同,因为需要得到均匀的薄膜,因此优选采用真空蒸镀法形成所述电子注入层。蒸镀条件可选择与空穴注入层、发光层相同的条件范围。
本发明的蒽衍生物的含有状态随在发光带区域和空穴输送带区域的哪一层中含有而不同,在使用真空蒸镀法时可以与其它材料同时蒸镀。另外,使用旋涂法时,可以与其它材料混合而含有。
最后层叠阴极,可以制得有机EL元件。
阴极由金属构成,可采用蒸镀法、溅射法形成。但是,为了使底层的有机物层免受制膜时的损伤,优选使用真空蒸镀法。
该有机EL元件的制作优选在一次抽真空之后,连续地从阳极制备至阴极。
本发明的有机EL元件的各层的形成方法没有特别限定。可使用以往公知的真空蒸镀法、旋涂法等形成方法。可采用以下公知的方法形成用于本发明有机EL元件的包含本发明蒽衍生物的有机薄膜层,所述方法为真空蒸镀法、分子束蒸镀法(MBE法)或者溶解于溶剂的溶液的浸涂法、旋涂法、浇铸法、棒涂法、辊涂法等涂敷法。
本发明的有机EL元件的各有机层的膜厚没有特别限定,通常膜厚过薄时,易产生针孔等缺陷,相反过厚时,需要施加高电压,导致效率下降,因此通常优选膜厚为数nm-1μm。
另外,当向有机EL元件施加直流电压时,通过使阳极的极性为正极,使阴极的极性为负极,施加5-40V电压时,可以观察到发光。另外,即使以相反的极性施加电压也不会流过电流,根本不发光。此外,施加交流电压时,仅在阳极的极性为正,而阴极的极性为负时,才能观察到均匀的发光。施加的交流电的波形可以是任意的。
实施例
下面,使用实施例对本发明进行更加详细的说明。
合成实施例1(9,10-二苯基-2-(6-苯基吡啶-2-基)蒽(化合物1)的合成)
按照下面的反应工序合成下述化合物1。
(1-a)2-溴蒽醌的合成
使溴化铜18g(81mmol)、亚硝酸叔丁酯12ml(101mmol)分散于65℃的乙腈中,并边剧烈搅拌,边滴加2-氨基蒽醌15g(67mmol)。搅拌到完全没有气体排出,冷却至室温,加入20%盐酸(1L),然后用二氯甲烷进行萃取。将有机层用硫酸镁干燥,减压馏出溶剂。用硅胶柱色谱法进行精制,获得2-溴蒽醌14g(收率75%)。
(1-b)2-溴-9,10-二苯基-9,9,10,10-四氢蒽-9,10-二醇的合成
在氩气环境中,使溴苯5.4ml(52mmol)溶解于脱水四氢呋喃(THF)100ml中,并冷却至-78℃,滴加叔丁基锂45ml(1.5M戊烷中)。在-78℃下搅拌1小时,然后加入2-溴蒽醌4.9g(17mmol)。加入氯化铵水溶液后,用二氯甲烷进行萃取。将有机层用硫酸镁干燥,减压馏出溶剂。将得到的固体用乙醇洗涤,获得2-溴-9,10-二苯基-9,9,10,10-四氢蒽-9,10-二醇6.8g(收率90%)。
(1-c)2-溴-9,10-二苯基蒽的合成
在氩气环境中,使2-溴-9,10-二苯基-9,9,10,10-四氢蒽-9,10-二醇4.5g(10mmol)溶解于醋酸,加入碘化钾17g(102mmol)、NaH2PO218g(167mmol),边剧烈搅拌3小时,边加热回流。冷却至室温,进行过滤。将得到的固体用水、甲醇洗涤,然后减压干燥,获得2-溴-9,10-二苯基蒽3.5g(收率85%)。
(1-d)9,10-二苯基蒽-2-硼酸的合成
在氩气环境中,在2-溴-9,10-二苯基蒽3.5g(8.6mmol)中加入脱水THF50ml,冷却至-78℃,滴加正丁基锂6.0ml(1.6M己烷中)。在-78℃下搅拌1小时,然后升温至0℃。再冷却至-78℃,滴加三甲氧基硼烷2.9ml(26mmol)。在-78℃下搅拌1小时,然后在室温下搅拌2小时。加入10%HCl50ml,搅拌1小时后过滤。将得到的固体用甲苯洗涤,获得9,10-二苯基蒽-2-硼酸2.6g(收率80%)。
(1-e)2-氨基-6-苯基吡啶的合成
使2-氨基-6-溴吡啶10g(58mmol)、苯基硼酸8.5 g(70mmol)、四(三苯基膦)钯1.3g(1.2mmol)溶解于1,2-二甲氧基乙烷60ml中,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,除去水层。将有机层用无水硫酸镁干燥,减压馏出溶剂。用硅胶色谱法精制残渣,获得2-氨基-6-苯基吡啶6.9g(收率70%)。
(1-f)2-溴-6-苯基吡啶的合成
在2-氨基-6-苯基吡啶6.9g(40mmol)中加入48%HBr50ml并搅拌。将溶液冷却至-20℃,滴加溴7.7g(48mmol)。再滴加亚硝酸钠2.8g(40mmol)。边升温至室温边搅拌3小时。反应结束后,用醋酸乙酯萃取,除去水层。将有机层用无水硫酸镁干燥,减压馏出溶剂。用硅胶色谱法精制残渣,获得2-溴-6-苯基吡啶7.5g(收率80%)。
(1-g)9,10-二苯基-2-(6-苯基吡啶-2-基)蒽(化合物1)的合成
使2-溴-6-苯基吡啶2.5g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml中,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体4.5g(收率84%)。该物质用质谱分析,结果,相对于分子量483.20,测量值m/e=483,确认是目标化合物1。
合成实施例2(9,10-二苯基-2-(4,6-二苯基嘧啶-2-基)蒽(化合物2)的合成)
按照下面的反应工序合成下述化合物2。
(2-a)2-氨基-4,6-二苯基嘧啶的合成
使2-氨基-4,6-二氯嘧啶9.5g(58mmol)、苯基硼酸17g(140mmol)、四(三苯基膦)钯2.7g(2.3mmol)溶解于1,2-二甲氧基乙烷120ml,加入2.0M碳酸钠水溶液60ml,在氩气环境中加热回流8小时。反应结束后,除去水层。将有机层用无水硫酸镁干燥,减压馏出溶剂。用硅胶色谱法精制残渣,获得2-氨基-4,6-二苯基嘧啶11g(收率77%)。
(2-b)2-溴-4,6-二苯基嘧啶的合成
在2-氨基-4,6-二苯基嘧啶11g(44mmol)中加入48%HBr50ml并搅拌。将溶液冷却至-20℃,滴加溴8.5g(53mmol)。再滴加亚硝酸钠3.1g(44mmol)。边升温至室温边搅拌3小时。反应结束后,用醋酸乙酯萃取,除去水层。将有机层用无水硫酸镁干燥,减压馏出溶剂。用硅胶色谱法精制残渣,获得2-溴-4,6-二苯基嘧啶11g(收率82%)。
(2-c)9,10-二苯基-2-(4,6-二苯基嘧啶-2-基)蒽(化合物2)的合成
使2-溴-4,6-二苯基嘧啶3.4g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体5.3g(收率86%)。该物质用质谱分析,结果,相对于分子量560.23,m/e=560,确认是目标化合物2。
合成实施例3(9,10-二苯基-2-(4,6-二苯基三嗪-2-基)蒽(化合物3)的合成)
按照下面的反应工序合成下述化合物3。
按照日本专利第3067878中记载的公知的方法,合成了2-氯-4,6-二苯基-1,3,5-三嗪。使2-氯-4,6-二苯基-1,3,5-三嗪2.9g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体5.3g(收率86%)。该物质用质谱分析,结果,相对于分子量560.23,m/e=560,确认是目标化合物3。
合成实施例4(9,10-二苯基-2-[4-(2,6-二苯基吡啶-4-基)苯基]蒽(化合物4)的合成)
按照下面的反应工序合成下述化合物4。
(4-a)4-溴苯基-2,6-二苯基吡啶的合成
使4-溴苯甲醛15.0g(81mmol)、苯乙酮9.7g(81mmol)溶解于乙醇300ml,加入28%甲醇钠甲醇溶液16.6ml(81mmol),在室温下搅拌9小时。反应结束后,将析出的晶体过滤并用乙醇洗涤,获得合成中间体(烯酮)19.6(收率84%)。
使合成中间体(烯酮)9.0g(31mmol)、1-苯甲酰甲基吡啶鎓溴化物8.7g(31mmol)、醋酸铵19.3g(250mmol)悬浮于醋酸27ml中,加热回流12小时。将反应溶液冷却至室温,加入甲苯、水,进行二层分离,然后将有机层依次用10%氢氧化钠水溶液、饱和食盐水洗涤,用无水硫酸钠干燥。减压馏出有机溶剂,然后加入乙醇27ml,滤出析出的晶体,用乙醇洗涤,获得4-溴苯基-2,6-二苯基吡啶10.6g(收率88%)。
(4-b)9,10-二苯基-2-[4-(2,6-二苯基吡啶-4-基)苯基]蒽(化合物4)的合成
使4-(4-溴苯基)-2,6-二苯基吡啶4.2g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体5.8g(收率83%)。该物质用质谱分析,结果,相对于分子量635.26,m/e=635,确认是目标化合物4。
合成实施例5(9,10-二苯基-2-[4-(2,6-二苯基嘧啶-4-基)苯基]蒽(化合物5)的合成)
按照下面的反应工序合成下述化合物5。
(5-a)4-(4-溴苯基)-2,6-二苯基嘧啶的合成
加入4-溴苯乙酮19.9g(100mmol)和苯甲醛10.6g(100mmol),进行氩气置换。接着,加入乙醇200ml和1N甲醇钠/甲醇溶液10ml,在室温下搅拌5小时。然后,在70℃的油浴中升温,并边回流边再反应4小时。接着,加入苄脒·盐酸盐9.40g(60mmol)、氢氧化钠8.00g(200mmol),在70℃的油浴中升温并反应5小时。反应结束后,将析出物过滤,用硅胶色谱法精制,获得4-(4-溴苯基)-2,6-二苯基嘧啶13.6(收率35%)。
(5-b)9,10-二苯基-2-[4-(2,6-二苯基嘧啶-4-基)苯基]蒽(化合物5)的合成
使4-(4-溴苯基)-2,6-二苯基嘧啶4.3g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体5.3g(收率76%)。该物质用质谱分析,结果,相对于分子量636.26,m/e=636,确认是目标化合物5。
合成实施例6(9,10-二苯基-2-[4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基]蒽(化合物6)的合成)
按照下面的反应工序合成下述化合物6。
(6-a)2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪的合成
使1,4-二溴苯2.64g(11.2mmol)溶解于干燥的四氢呋喃30ml,冷却至-70℃。向该溶液中慢慢地滴加正丁基锂的己烷溶液(1.6M)7.4ml(11.8mmol),在-70℃下搅拌30分钟。在该混合物中在-70℃下滴加2-氯-4,6-二苯基-1,3,5-三嗪3.00g(11.2mmol)的四氢呋喃溶液,在-70℃下搅拌30分钟,然后慢慢地升温至室温,再搅拌1.5小时。将得到的混合物用醋酸乙酯萃取,用水、饱和食盐水依次洗涤有机相,用无水硫酸镁干燥,然后馏出溶剂,用硅胶色谱法精制,获得2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪1.48(收率34%)。
(6-b)9,10-二苯基-2-[4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基]蒽(化合物6)的合成
使2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪4.3g(11mmol)、9,10-二苯基蒽-2-硼酸4.9g(13mmol)、四(三苯基膦)钯0.25g(0.22mmol)溶解于1,2-二甲氧基乙烷60ml,加入2.0M碳酸钠水溶液30ml,在氩气环境中加热回流8小时。反应结束后,过滤,将得到的固体用水、甲醇、甲苯洗涤,获得绿白色固体5.6g(收率80%)。该物质用质谱分析,结果,相对于分子量637.25,m/e=637,确认是目标化合物6。
实施例1
将25mm×75mm×1.1mm厚的带ITO透明电极的玻璃基板(ジォマティック社制)在异丙醇中进行超声波清洗5分钟后,进行UV臭氧清洗30分钟。将清洗后的带透明电极线的玻璃基板装载在真空蒸镀装置的基板座上,首先,在形成有透明电极线的一侧的面上,通过电阻加热蒸镀形成膜厚60nm的N,N’-双(N,N’-二苯基-4-氨基苯基)-N,N-二苯基-4,4’-二氨基-1,1’-联苯膜(TPD232膜),覆盖所述透明电极。该TPD232膜具有第一空穴注入层(或者空穴输送层)的功能。在该TPD232膜上通过电阻加热蒸镀形成膜厚20nm的4,4’-双[N-(1-萘基)-N-苯基氨基]联苯膜(NPD膜)。该NPD膜具第二空穴注入层(或者空穴输送层)的功能。此外,在该NPD膜上通过电阻加热蒸镀形成膜厚40nm的4’,4”-双(2,2-二苯基乙烯基)-9,10-二苯基蒽膜(DPVDPAN)。该DPVDPAN膜具有发光层的功能。
另外,在该DPVDPAN膜上通过蒸镀形成膜厚10nm的上述化合物1膜。该化合物1膜具电子注入层(或者电子输送层)的功能。然后,使用Li(Li源:サエスゲッタ一社制)和上述化合物1进行二元蒸镀,从而作为电子注入层(或者阴极),以成膜速度1.5/sec:1/min形成膜厚10nm化合物1:Li膜。在该化合物1:Li膜上蒸镀金属Al,形成膜厚130nm金属阴极,从而形成有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
实施例2-5
除了在实施例1中,使用上述化合物2(实施例2)、上述化合物3(实施例3)、上述化合物4(实施例4)、上述化合物5(实施例5)代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
实施例6
除了在实施例1中,使用化合物1代替发光层中使用的DPVDPAN,使用化合物5代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
实施例7
除了在实施例1中,使用化合物2代替发光层中使用的DPVDPAN,使用化合物5代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
实施例8
除了在实施例1中,使用化合物3代替发光层中使用的DPVDPAN,使用化合物5代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
实施例9
除了在实施例1中,使用化合物4代替发光层中使用的DPVDPAN,使用化合物5代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
对得到的元件通电,结果获得了均匀的蓝色发光。另外,在初始亮度300cd/m2下恒流驱动该元件,结果可持续1000小时以上均匀发光。
比较例1-2
除了在实施例1中,使用下述化合物A(比较例1)、下述化合物B(比较例2)代替电子注入层(或者电子输送层)和电子注入层(或者阴极)中使用的化合物1以外,相同地制作有机EL元件。
在初始亮度300cd/m2下恒流驱动得到的比较例1的元件,结果比较例1的元件在过100小时后发光减半,确认有大量的黑点。
另外,在初始亮度300cd/m2下恒流驱动得到的比较例2的元件,结果比较例2的元件在过10小时后发光减半,确认有大量的黑点。
化合物A 化合物B
如上所述,在电子注入层中使用了本发明的蒽衍生物的实施例1-9的有机EL元件可以提高电子注入层和阴极的粘着性,获得了均匀的发光,可长期稳定驱动。
工业上的可利用性
如以上所详细说明,本发明蒽衍生物及使用它的有机EL元件经过长时间后仍可获得均匀的发光,寿命长。因此,非常适宜用作实用性高的有机EL元件。
Claims (11)
3.一种有机电致发光元件,其中在阴极和阳极间挟持有至少具有发光层的由一层或多层构成的有机薄膜层,该有机薄膜层的至少一层中,单独或者作为混合物的成分含有权利要求1记载的蒽衍生物。
4.如权利要求3所述的有机电致发光元件,其中主要在发光带区域含有所述蒽衍生物。
5.如权利要求3所述的有机电臻发光元件,其中在发光层中含有所述蒽衍生物。
6.如权利要求5所述的有机电致发光元件,其中所述发光层中还含有芳胺化合物和/或苯乙烯胺化合物。
7.如权利要求5所述的有机电致发光元件,其中所述发光层中还含有金属配位化合物。
8.如权利要求3所述的有机电致发光元件,其中所述有机薄膜层具有空穴注入层和/或空穴输送层,该空穴注入层和/或空穴输送层中,单独或者作为混合物的成分含有权利要求1记载的蒽衍生物。
9.如权利要求3所述的有机电致发光元件,其中所述有机薄膜层具有电子注入层和/或电子输送层,该电子注入层和/或电子输送层中,单独或者作为混合物的成分含有权利要求1记载的蒽衍生物。
10.如权利要求9所述的有机电致发光元件,其中所述电子注入层和/或电子输送层中含有还原性掺杂剂。
11.如权利要求10所述的有机电致发光元件,其中所述还原性掺杂剂为选自碱金属、碱土金属、稀土金属、碱金属的氧化物、碱金属的卤化物、碱土金属的氧化物、碱土金属的卤化物、稀土金属的氧化物、稀土金属的卤化物、碱金属的有机配位化合物、碱土金属的有机配位化合物及稀土金属的有机配位化合物中的至少一种。
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JP (1) | JP4790260B2 (zh) |
KR (1) | KR101336544B1 (zh) |
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CN105593213A (zh) * | 2013-10-04 | 2016-05-18 | 默克专利有限公司 | 作为用于电子器件的材料的三芳基胺取代的苯并[h]喹啉-衍生物 |
CN105593213B (zh) * | 2013-10-04 | 2019-02-05 | 默克专利有限公司 | 作为用于电子器件的材料的三芳基胺取代的苯并[h]喹啉-衍生物 |
CN108727253A (zh) * | 2018-05-10 | 2018-11-02 | 江苏师范大学 | 芳环-三芳基吡啶化合物及其制备方法和应用 |
CN111100626A (zh) * | 2018-10-26 | 2020-05-05 | 佳能株式会社 | 组合物、包括该组合物的有机发光器件、显示装置、光电转换设备、电子设备和移动体 |
CN111100626B (zh) * | 2018-10-26 | 2024-01-19 | 佳能株式会社 | 组合物、包括该组合物的有机发光器件、显示装置、光电转换设备、电子设备和移动体 |
CN110845422A (zh) * | 2019-11-28 | 2020-02-28 | 吉林奥来德光电材料股份有限公司 | 一种有机发光化合物、其合成方法及有机电致发光器件 |
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KR101336544B1 (ko) | 2013-12-03 |
WO2006067931A1 (ja) | 2006-06-29 |
JP4790260B2 (ja) | 2011-10-12 |
TW200630462A (en) | 2006-09-01 |
US20080111473A1 (en) | 2008-05-15 |
KR20070088728A (ko) | 2007-08-29 |
JP2006176448A (ja) | 2006-07-06 |
US8217570B2 (en) | 2012-07-10 |
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