CN1842581A - 有机电致发光元件 - Google Patents
有机电致发光元件 Download PDFInfo
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- CN1842581A CN1842581A CNA2004800242560A CN200480024256A CN1842581A CN 1842581 A CN1842581 A CN 1842581A CN A2004800242560 A CNA2004800242560 A CN A2004800242560A CN 200480024256 A CN200480024256 A CN 200480024256A CN 1842581 A CN1842581 A CN 1842581A
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- 239000010410 layer Substances 0.000 claims abstract description 204
- 239000000463 material Substances 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000000758 substrate Substances 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- -1 pyridyl phenoxy zinc Chemical compound 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229910052709 silver Inorganic materials 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 229910052737 gold Inorganic materials 0.000 claims abstract description 8
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 7
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 6
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 6
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 6
- 239000012044 organic layer Substances 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 230000005540 biological transmission Effects 0.000 claims description 48
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 125000002524 organometallic group Chemical group 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000005259 triarylamine group Chemical group 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 abstract description 6
- 125000003368 amide group Chemical group 0.000 abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 15
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 13
- 239000011701 zinc Substances 0.000 description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 10
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- 238000000151 deposition Methods 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
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- 230000005012 migration Effects 0.000 description 7
- 238000013508 migration Methods 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
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- 150000002739 metals Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 description 2
- HPDNGBIRSIWOST-UHFFFAOYSA-N 2-pyridin-2-ylphenol Chemical compound OC1=CC=CC=C1C1=CC=CC=N1 HPDNGBIRSIWOST-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
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- 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 2
- 238000007740 vapor deposition Methods 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- XANLLBRVHIYWIY-UHFFFAOYSA-N O=C1C2=CC=CC=C2C(=O)C2=C1C(=N)C(=N)C=C2 Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(=N)C(=N)C=C2 XANLLBRVHIYWIY-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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Abstract
本发明提供元件的发光效率得到了改善，充分确保了驱动稳定性且具有简化结构的利用了磷光发光的有机电致发光元件(有机EL元件)。有机EL元件，在基板上层合阳极、含有空穴传输层、发光层和电子传输层的有机层以及阴极而形成，在发光层与阳极之间具有空穴传输层，在发光层与阴极之间具有电子传输层，发光层含有作为主体材料的下述通式(I)所示的吡啶基苯氧基锌配位化合物，以及作为客体材料的含有选自Ru、Rh、Pd、Ag、Re、Os、Ir、Pt及Au中至少一种金属的有机金属络合物。(式中，R1～R8表示H、烷基、链烯基、氰基、氨基、酰胺基、烷氧羰基、羧基、烷氧基或芳基等。)
Description
技术领域
本发明涉及有机电致发光元件(以下称为有机EL元件)，具体而言，涉及在有机化合物组成的发光层上施加电场而发光的薄膜型装置。
技术背景
对于使用了有机材料的电致发光元件的开发，通过以提高从电极注入电荷的效率为目的的电极种类最优化，开发在电极间以薄膜形式设置有由芳香族二胺组成的空穴传输层和由8-羟基喹啉铝络合物(以下称为Alq3)组成的发光层的元件(Appl.Phys.Lett.，vol.51，p913，1987)，与以往使用蒽等单晶体的元件相比，大幅度改善了发光效率，因而推动了向具有自发光·高速应答性特征的高性能平板的实用化进程。
为了进一步改善这种有机EL元件的效率，已知的是以上述阳极/空穴传输层/发光层/阴极的构成为基础，在其中适当地设置空穴注入层、电子注入层及电子传输层的元件，例如具有以下结构的元件：阳极/空穴注入层/空穴传输层/发光层/阴极、阳极/空穴注入层/发光层/电子传输层/阴极、阳极/空穴注入层/发光层/电子传输层/电子注入层/阴极、阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/阴极等。所述空穴传输层具有将由空穴注入层注入的空穴输送到发光层的功能，而电子传输层具有将由阴极注入的电子输送到发光层的功能。另外，有时也将空穴注入层称为阳极缓冲层。
已知通过在发光层和空穴注入层之间插入所述空穴传输层，可以在更低的电场下向发光层注入大量空穴，而且由于电子极难流过空穴传输层，因而从阴极或电子传输层向发光层中注入的电子就蓄积在空穴传输层和发光层的交界面上，从而提高了发光效率。
同样地，已知通过在发光层和电子注入层之间插入电子传输层，可以在更低的电场下向发光层注入大量电子，而且由于空穴极难流过电子传输层，因而从阳极或空穴传输层向发光层中注入的空穴就蓄积在电子传输层和发光层的交界面上，从而提高了发光效率。与这种结构层的功能相适应，至今已进行了多种有机材料的开发。
另一方面，以上述设置有由芳香族二胺组成的空穴传输层和由Alq3组成的发光层的元件为代表的许多元件采用荧光发光，但人们期待着采用磷光发光，即如果利用来自三重线激发态的发光，使效率较以往使用荧光(单态)的元件提高约3倍。为了达到此目的，研究了以香豆素衍生物或二苯甲酮衍生物作为发光层，但仅获得了极低的辉度。之后，作为利用三重线状态的尝试，对使用铕络合物进行了研究，但仍未达到高效率发光。
最近报告了通过使用铂络合物(PtOEP)可以高效率地发红色光(Nature，395卷，第151页，1998年)。之后，通过在发光层中掺杂铱络合物(Ir(ppy)3)，大大改善了发绿色光的效率。而且报告，这些铱络合物通过对发光层最优化，即使使元件结构更为简化，也能显示出极高的发光效率。
上述PtOEP及Ir(ppy)3等的化学式记载于下述文献等中，将其作为参考。另外，主体材料、客体材料、空穴注入层、电子传输层等有机层中通常使用的化合物的结构式、简写也记载于下述文献中，将其作为参考。以下内容中未指明而使用的简写是本技术领域中通用的简写，可按下述文献等中所述简写的意义进行理解。
本发明中涉及的现有文献如下所示。
专利文献1：特开2002-305083号公报
专利文献2：特开2001-313178号公报
专利文献3：特开2002-352957号公报
专利文献4：特开2000-357588号公报
非专利文献1：C.Adachi，et.al.，Appl.Phys.Lett.77，904(2000)
在磷光有机电致发光元件开发中，所提出的主体材料是上述专利文献2中介绍的咔唑化合物CBP。如果绿色磷光发光材料三(2-苯基吡啶)铱络合物(以下称为Ir(ppy)3)使用CBP作为主体材料，则CBP除了具有易流过空穴和不易流过电子的特性外，还打破了电荷注入的平衡，使过多的空穴流至电子传输侧，结果使来自Ir(ppy)3的发光效率下降。
解决上述问题的手段有在发光层和电子传输层之间设置空穴阻挡层的方法。该空穴阻挡层能够使空穴高效地蓄积在发光层中，从而提高其在发光层中与电子再结合的概率，实现了高效率发光。作为目前通常使用的空穴阻挡材料，可以列举2，9-二甲基-4，7-二苯基-1，10-菲绕啉(以下称为BCP)及对苯基酚代-双(2-甲基-8-喹啉酚代-N1，O8)铝(以下称为BAlq)。
另外，作为CBP之外可使用的主体材料，专利文献1公开了使用由具有含氮杂环Ar1及芳香环Ar2的基团和金属M组成的络合物(-Ar1-Ar2-O-)nM作为发光层的主体材料，使用贵金属类的金属络合物作为客体材料的有机EL元件。本文中例示的主体材料有很多，Ar1为吡啶环、Ar2为苯环的化合物例示了众多化合物中的一种。其中还例示了M为Zn、n为2的化合物，但仅此而已。另外，还列举了用贵金属类的金属络合物作为客体材料的多个例子。
另一方面，作为磷光有机电致发光元件的主体材料还提出了专利文献3中介绍的3-苯基-4-(1’-萘基)-5-苯基-1，2，4-三唑(以下称为TAZ)，但除了易流过电子和不易流过空穴的特性之外，发光区域处于空穴传输层侧。因此可知，由于空穴传输层材料与Ir(ppy)3的亲合性问题，来自Ir(ppy)3的发光效率降低。例如，从空穴传输层的高性能、高可靠性、高寿命方面来看最宜使用的4，4’-双(N-(1-萘基)-N-苯基氨基)联苯(以下称为NPB)与Ir(ppy)3的亲合性差，引起了从TAZ向NPB的能量迁移，存在着向Ir(ppy)3的能量迁移效率降低、发光效率降低的问题。
解决述问题的手段有使用4，4’-双(N，N’-(3-甲苯基)氨基)-3，3’-二甲基联苯(以下称为HMTPD)之类不会引起能量从Ir(ppy)3迁移的材料作为空穴传输层的方法。
在上述非专利文献1中，报告了通过在发光层的主体材料中使用TAZ、1，3-双(N，N-叔丁基-苯基)-1，3，4-唑(以下称为OXD7)或BCP，在掺杂材料中使用Ir(ppy)3，在电子传输层中使用Alq3，在空穴传输层中使用HMTPD，在磷光发光元件中，可通过3层结构实现高效率发光，而使用了TAZ的体系获得了特别优异的效果。但是，由于HMTPD的Tg约为50℃左右，是易于结晶的材料，缺乏可靠性。因此，元件的寿命极短，难以进行商业应用，且存在驱动电压高的问题。
专利文献4中记载了使用了双(2-苯氧基-2-吡啶基)锌等金属络合物的有机EL元件，但未采用磷光发光。
发明内容
为了将有机EL元件应用于平板显示器等的显示元件，必须在改善元件发光效率的同时，充分确保驱动时的稳定性。鉴于上述现状，本发明的目的是提供具有高效率、长使用寿命及简化的元件结构且可进行实用的有机EL元件。
本发明涉及在基板上层合阳极、含有空穴传输层、发光层和电子传输层的有机层以及阴极而形成的，在发光层与阳极之间具有空穴传输层，在发光层与阴极之间具有电子传输层的有机电致发光元件，其特征在于：发光层含有作为主体材料的下述通式(I)所示的化合物，以及作为客体材料的含有选自钌、铑、钯、银、铼、锇、铱、铂及金中至少一种金属的有机金属络合物。
式中，R1～R8各自独立地表示氢原子、烷基、芳烷基、链烯基、氰基、氨基、酰胺基、烷氧羰基、羧基、烷氧基、可具有取代基的芳香族烃基或可具有取代基的芳香族杂环基。
其中，如果空穴传输层含有具有至少2个稠环芳基的三芳基胺二聚体，三芳基胺二聚体为下述通式(II)所示的化合物，则可获得更佳的有机EL元件。
式中，Ar1及Ar2为碳原子数6～14的1价芳基，但至少一方为碳原子数10～14的具有稠环结构的芳基，Ar3为碳原子数6～14的2价芳基。
另外，当客体材料为绿色磷光发光性的三(2-苯基吡啶)铱络合物时，也给出了优选的有机EL元件。
本发明的有机EL元件涉及所谓使用了磷光的有机EL元件，其在发光层中含有上述通式(I)所示的化合物、及含有选自周期表7～11族中至少一种金属的磷光性有机金属络合物。其发光层中含有作为主成分的通式(I)所示的化合物，作为副成分的含有选自钌、铑、钯、银、铼、锇、铱、铂及金中至少一种金属的有机金属络合物。
其中，主成分是指在形成该层的材料中占大于等于50重量％的成分，副成分是指在形成该层的材料中不足50重量％的成分。在本发明的有机电致发光元件中，对发光层中所含的通式(I)所示化合物的基本要求是，具有比该层中所含的磷光性有机金属络合物的激发三重线态能级能量更高的激发三重线态能级。另外，还必需是能够给予稳定的薄膜形状，和/或具有高玻璃化转变温度(Tg)，可高效地传输空穴和/或电子的化合物。而且要求是在电化学和化学上稳定的，在制造或使用时难以产生形成阱或导致消光的杂质的化合物。
为了使磷光性有机络合物的发光不易受到空穴传输层的激发三重线态能级的影响，另一个重要事项是要具备可使发光区域与空穴传输层界面保持适度的距离的空穴注入能力。
作为满足这些条件的发光层形成材料，本发明中使用上述通式(I)所示的化合物作为主体材料。在通式(I)中，R1～R8各自独立地表示氢原子、烷基、芳烷基、链烯基、氰基、氨基、酰胺基、烷氧羰基、羧基、烷氧基、可具有取代基的芳香族烃基或可具有取代基的芳香族杂环基。作为烷基，优选例示碳原子数为1～6的烷基(以下称为低级烷基)，作为芳烷基，优选例示苄基、苯乙基，作为链烯基，优选例示碳原子数为1～6的低级链烯基，作为氨基，优选例示-NR2(R为氢或低级烷基)所示的氨基，作为酰胺基，优选例示-CONH2，作为烷氧羰基及烷氧基的烷氧基，优选例示碳原子数为1～6的低级烷氧基。
另外，作为芳香族烃基，优选例示苯基、萘基、苊基、蒽基等芳香族烃基，作为芳香族杂环基，优选例示吡啶基、喹啉基、噻吩基、咔唑基、吲哚基、呋喃基等芳香族杂环基。当其为具有取代基的芳香族烃基或芳香族杂环基时，作为取代基，可以列举低级烷基、低级烷氧基、苯氧基、甲苯氧基、苄氧基、苯基、萘基、二甲氨基等。
作为通式(I)所示的化合物，更优选选自R1～R8为氢原子、低级烷基、低级烷氧基或碳原子数为1～10的芳香族烃基的化合物。进一步优选R1～R8中大于等于6个为氢原子、其他为低级烷基的化合物，最优选全部为氢原子的化合物。
该通式(I)所示的化合物是通过锌盐与式(III)所示化合物之间进行络合物形成反应而合成的。式(III)中，R1～R8对应于通式(I)中的R1～R8。
上述通式(I)所示化合物的优选具体例列于下文，但该化合物并不局限于此。
表1
| 化合物序号 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
| 1 | H | H | H | H | H | H | H | H |
| 2 | Me | H | H | H | H | H | H | H |
| 3 | t-Bu | H | t-Bu | H | H | H | H | H |
| 4 | t-Bu | H | t-Bu | H | H | H | CF3 | H |
| 5 | Ph | H | H | H | H | H | H | H |
| 6 | NO2 | H | H | H | H | H | H | H |
| 7 | NO2 | H | NO2 | H | H | H | H | H |
| 8 | NO2 | H | NO2 | H | H | H | OMe | H |
| 9 | NO2 | H | NO2 | H | H | H | OPh | H |
| 10 | N(Me)2 | H | H | H | H | H | H | H |
| 11 | N(Me)2 | H | N(Me)2 | H | H | H | H | H |
| 12 | CF3 | H | H | H | H | H | H | H |
| 13 | H | Me | H | H | H | H | H | H |
| 14 | H | t-Bu | H | t-Bu | H | H | H | H |
| 15 | H | t-Bu | H | t-Bu | Me | H | H | H |
| 16 | H | Ph | H | H | H | H | H | H |
| 17 | H | OMe | H | H | H | H | H | H |
| 18 | H | OPh | H | H | H | H | H | H |
| 19 | H | NO2 | H | H | H | H | H | H |
| 20 | H | N(Me)2 | H | H | H | H | H | H |
| 21 | H | H | OMe | H | H | H | H | H |
| 22 | H | H | OPh | H | H | H | H | H |
| 23 | H | H | NO2 | H | H | H | H | H |
| 24 | H | H | NO2 | H | Me | H | H | H |
| 25 | H | H | NO2 | H | Ph | H | H | H |
表2
| 化合物序号 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
| 26 | H | H | NO2 | H | H | OMe | H | H |
| 27 | H | H | NO2 | H | H | OPh | H | H |
| 28 | H | H | NO2 | H | H | Me | H | H |
| 29 | H | H | NO2 | H | H | Ph | H | H |
| 30 | H | H | N(Me)2 | H | H | H | H | H |
| 31 | H | H | CF3 | H | H | H | H | H |
| 32 | H | H | CN | H | H | H | H | H |
| 33 | H | H | CN | H | Me | H | H | H |
| 34 | H | H | CN | H | Ph | H | H | H |
| 35 | H | H | F | H | H | H | H | H |
| 36 | H | H | NHCOMe | H | H | H | H | H |
| 37 | H | H | NHCOPh | H | H | H | H | H |
| 38 | H | H | OCOEt | H | H | H | H | H |
| 39 | H | H | OCOPh | H | H | H | H | H |
| 40 | H | H | H | n-Bu | H | H | H | H |
| 41 | H | H | H | Ph | H | H | H | H |
| 42 | H | H | H | OMe | H | H | H | H |
| 43 | H | H | H | OPh | H | H | H | H |
| 44 | H | H | H | H | Me | H | H | H |
| 45 | H | H | H | H | Et | H | Me | H |
| 46 | H | H | H | H | Ph | H | H | H |
| 47 | H | H | H | H | OMe | H | H | H |
| 48 | H | H | H | H | OPh | H | H | H |
| 49 | H | H | H | H | H | Me | H | H |
| 50 | H | H | H | H | H | t-Bu | H | H |
| 51 | H | H | H | H | H | Ph | H | H |
| 52 | H | H | H | H | H | OMe | H | H |
| 53 | H | H | H | H | H | OPh | H | H |
表3
| 化合物序号 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
| 54 | H | H | H | H | H | CN | H | H |
| 55 | H | H | H | H | H | H | H | Me |
| 56 | H | H | H | H | H | H | H | Ph |
| 57 | H | H | H | H | H | H | H | CN |
| 58 | H | H | H | H | H | H | H | COOMe |
| 59 | H | H | H | H | H | H | H | CH2N(Et)2 |
发光层中的客体材料含有有机金属络合物，所述有机金属络合物含有选自钌、铑、钯、银、铼、锇、铱、铂及金中的至少一种金属。该有机金属络合物公知于上述专利文献等中，可从其中选择使用。
作为优选的有机金属络合物，可以列举下述通式(IV)所示的化合物。
此处的M表示上述金属，n为该金属的价数。
另外，环A1表示可具有取代基的芳香族烃环基或芳香族杂环基，优选表示苯基、联苯基、萘基、蒽基、噻吩基、吡啶基、喹啉基或异喹啉基。作为其可具有的取代基，可以列举氟原子等卤原子；甲基、乙基等碳原子数为1～6的烷基；乙烯基等碳原子数为2～6的链烯基；甲氧羰基、乙氧羰基等碳原子数为2～6的烷氧羰基；甲氧基、乙氧基等碳原子数为1～6的烷基；乙烯基等碳原子数为2～6的链烯基；甲氧羰基、乙氧羰基等碳原子数为2～6的烷氧羰基；甲氧基、乙氧基等碳原子数为1～6的烷氧基；苯氧基、苄氧基等芳氧基；二甲氨基、二乙氨基等二烷基氨基；乙酰基等酰基；三氟甲基等卤代烷基；氰基等。
环A2表示可具有取代基的含有氮作为杂环形成原子的芳香族杂环基，优选表示吡啶基、嘧啶基、吡嗪基、三嗪基、苯并噻唑基、苯并唑基、苯并咪唑基、喹啉基、异喹啉基、喹喔啉基或菲啶基。
作为它们可具有的取代基，可以列举氟原子等卤原子；甲基、乙基等碳原子数为1～6的烷基；乙烯基等碳原子数为2～6的链烯基；甲氧羰基、乙氧羰基等碳原子数为2～6的烷氧羰基；甲氧基、乙氧基等碳原子数为1～6的烷氧基；苯氧基、苄氧基等芳氧基；二甲氨基、二乙氨基等二烷基氨基；乙酰基等酰基；三氟甲基等卤代烷基；氰基等。
环A1具有的取代基和环A2具有的取代基可结合形成一个稠环，可以列举7，8-苯并喹啉基等。作为环A1及环A2的取代基，更优选为烷基、烷氧基、芳香族烃环基或氰基。作为式(IV)中的M，优选列举钌、铑、钯、银、铼、锇、铱、铂及金。上述通式(IV)所示的有机金属络合物的具体例示于下文中，但并不局限于此。
其中优选的是下述D-1所示的发绿色磷光性的三(2-苯基吡啶)铱络合物。
本发明的有机EL元件在发光层与阳极间具有空穴传输层。作为空穴传输层中含有的空穴传输材料，可以含有具有至少2个稠环芳基的三芳基胺二聚体。三芳基胺二聚体是指表示为(-Ar-NAr2)2的化合物，此处的Ar表示芳基或亚芳基。
作为该三芳基胺二聚体，优选列举上述通式(II)所示的化合物。在通式(II)中，Ar1及Ar2为碳原子数为6～14的1价芳基，但至少一方为碳原子数10～14的具有稠环结构的芳基。作为具有稠环结构的芳基，优选列举萘基、低级烷基取代的萘基等具有2～3环稠环结构的芳基。作为具有稠环结构的芳基以外的芳基，优选列举苯基、低级烷基取代的苯基、联苯基等具有苯环的芳基。Ar3为碳原子数为6～14的2价芳基，优选列举亚苯基、低级烷基取代的亚苯基等。
作为优选的三芳基胺二聚体，具体地可以列举NPB、4，4’-双(N-(9-菲基)-N-苯基氨基)联苯(以下称为PPB)等。
本发明中在发光层中使用的主体材料由于可以大致均等地流过电子和空穴，因此可以在发光层的中央进行发光。因而，不会象TAZ那样在空穴传输侧发光从而因能量向空穴传输层迁移而导致效率下降，也不会象CPB那样在电子传输层侧发光从而因能量向电子传输层迁移而使效率下降，可以在空穴传输层使用NPB、在电子传输层使用Alq3这种高可靠性材料。
附图说明
图1为显示有机电致发光元件一例的模式截面图。
符号说明
1基板，2阳极，3空穴注入层，4空穴传输层，5发光层，6电子传输层，7阴极
具体实施方式
以下，参照附图对本发明的有机EL元件进行说明。图1为模式化地表示本发明中使用的一般有机EL元件的结构例的截面图，1表示基板，2表示阳极，3表示空穴注入层，4表示空穴传输层，5表示发光层，6表示电子传输层，7表示阴极。在本发明的有机EL元件中，具有基板、阳极、空穴传输层、发光层、电子传输层及阴极作为必要层，可以省略必要层以外的层，例如空穴注入层，另外，必要时可设置其他层。本发明的有机EL元件可以设置空穴阻挡层，但是如果不设置空穴阻挡层，则可以简化层结构，在制造上和性能上带来优点。
基板1是有机电致发光元件的支撑体，可以使用石英或玻璃板、金属板或金属箔、塑料膜或板等。特别优选玻璃板、或聚酯、聚甲基丙烯酸酯、聚碳酸酯、聚砜等透明的合成树脂板。使用合成树脂基板时，必须注意阻气性。如果基板的阻气性过小，则有机电致发光元件有时会因透过基板的外部气体而发生劣化，因而不是优选的。因而优选的方法之一是在合成树脂基板的至少单面上设置致密的氧化硅膜等，从而确保阻气性的方法。
阳极2设置于基板1上，阳极起着向空穴传输层注入空穴的作用。该阳极通常由铝、金、银、镍、钯、铂等金属，铟和/或锡的氧化物等金属氧化物，碘化铜等卤化金属，炭黑、或聚(3-甲基噻吩)、聚吡咯、聚苯胺等导电性高分子等构成。阳极通常大多是通过溅射法、真空蒸镀法等形成的。另外，在使用银等金属微粒、碘化铜等微粒、炭黑、导电性的金属氧化物微粒、导电性高分子微粉末等情况下，也可以分散在适当的粘结剂树脂溶液中，通过涂布于基板1上而形成阳极2。而且，当使用导电性高分子时，也可以通过电解聚合直接在基板1上形成薄膜，或在基板1上涂布导电性高分子来形成阳极2。也可以使用不同物质进行层合来形成阳极。阳极的厚度根据所需要的透明性而变化。当需要透明性时，通常希望可见光的透过率达到大于等于60％，优选大于等于80％，此时的厚度通常为5～1000nm，优选为10～500nm左右。当为不透明时，阳极2可与基板1相同。另外，也可以在上述阳极2上进一步层合不同的导电材料。
空穴传输层4设置于阳极2上。两者之间还可以设置空穴注入层3。作为空穴传输层材料所需具备的条件，必须是来自阳极的空穴注入效率高、且能够高效地输送所注入的空穴的材料。因此，要求该材料的离子化电势低，对可见光的透明性高，并且空穴迁移率大，且稳定性优异，难以在制造或使用时产生成为阱的杂质。另外，还要求不会因与发光层5接触而对来自发光层的发光产生消光，不会在其与发光层之间形成受激态络合物而降低效率。除了上述一般要求外，当考虑车载显示用途时，还要求元件具有耐热性。因而，希望材料具有大于等于85℃的Tg值。
在本发明的有机EL元件中，空穴传输材料可以使用上述的NPB、PPB这样的三芳基胺二聚体。
必要时还可以与三芳基胺二聚体一起使用其他的用作空穴传输材料的公知化合物。例如，可以列举含有大于等于2个的叔胺，大于等于2个的稠合芳香环取代于氮原子的芳香族二胺、4，4′，4″-三(1-萘基苯基氨基)三苯胺等具有星放射状结构的芳香族胺化合物、由三苯胺的四聚体组成的芳香族胺化合物、2，2′，7，7′-四-(二苯基氨基)-9，9′-螺二芴等螺化合物等。这些化合物可以单独使用，必要时也可以分别混合使用。
另外，除上述化合物之外，作为空穴传输层的材料，可以列举聚乙烯基咔唑、聚乙烯基三苯胺、含有四苯基联苯胺的聚芳醚砜等高分子材料。
当用涂布法形成空穴传输层时，添加和溶解大于等于一种的空穴传输材料和必要时使用的不成为空穴的阱的粘结剂树脂及涂布改进剂等添加剂，配制成涂布溶液，用旋涂法等方法涂布于阳极2上，干燥后形成空穴传输层4。作为粘结剂树脂，可以列举聚碳酸酯、聚芳酯、聚酯等。粘结剂树脂添加量大时，空穴迁移率变小，因此最好少量添加，通常优选小于等于50重量％。
当采用真空蒸镀法形成时，将空穴传输材料放入设置于真空容器内的坩埚中，用适当的真空泵对真空容器内进行排气直至10-4Pa左右，然后加热坩埚，使空穴传输材料蒸发，从而在相向于坩埚设置的形成有阳极的基板上形成空穴传输层4。空穴传输层4的膜厚通常为5～300nm，优选为10～100nm。为了形成如此薄的膜，通常优选使用真空蒸镀法。
发光层5设置于空穴传输层4上。发光层5含有上述通式(I)所示的化合物和上述含有选自周期表中7～11族金属的有机金属络合物，其处于施加了电场的电极之间，由于从阳极注入并通过空穴传输层的空穴与从阴极注入并通过电子传输层6的电子进行再结合而被激发，产生强烈的发光。发光层5可以在不损害本发明的性能的范围内含有其他的主体材料(与通式(I)起同样的作用)及荧光色素等其他成分。
上述有机金属络合物在发光层中的含量优选为0.1～30重量％的范围。如果小于0.1重量％，则不能使元件的发光效率得到提高，如果超过30重量％，则有机金属络合物间形成二聚体等而引起浓度消光，导致发光效率降低。与以往采用荧光(单态)的元件中发光层中所含的荧光性色素(掺杂剂)的量相比，倾向于优选该含量稍多一些。有机金属络合物可以局部性地分布在发光层中的膜厚方向上，或不均匀地分布。
发光层5的膜厚通常为10～200nm，优选为20～100nm。按与空穴传输层4相同的方法形成薄膜。
为了进一步提高元件的发光效率，可以在发光层5和阴极7之间设置电子传输层6。电子传输层6由在施加了电场的电极间可以高效地将从阴极注入的电子向发光层5的方向输送的化合物形成。作为电子传输层6中使用的电子传输性化合物，必须是来自阴极7的电子注入效率高，并具有高电子迁移率，能够高效地输送所注入电子的化合物。
作为满足这种条件的电子传输材料，可以列举Alq3等金属络合物、10-羟基苯并[h]喹啉的金属络合物、二唑衍生物、二苯乙烯基联苯衍生物、シロ一ル衍生物、3-或5-羟基黄酮金属络合物、苯并唑金属络合物、苯并噻唑金属络合物、三苯并咪唑基苯、喹喔啉化合物、菲绕啉衍生物、2-叔丁基-9，10-N，N′-二氰基蒽醌二亚胺、n形氢化无定形碳化硅、n型硫化锌、n型硒化锌等。电子传输层6的膜厚通常为5～200nm，优选为10～100nm。
与空穴传输层4相同，采用涂布法或真空蒸镀法通过在发光层5上进行层合来形成电子传输层6。通常采用真空蒸镀法。
电子传输层6被层合于发光层5上，但它们之间还可以存在有空穴阻挡层。
为了进一步提高空穴注入的效率及改善整个有机层对阳极的附着力，也可以在空穴传输层4和阳极2之间插入空穴注入层3。通过插入空穴注入层3，可以在降低元件初始驱动电压的同时，具有抑制以恒定电流连续驱动元件时的电压上升的效果。作为用于空穴注入层的材料所需具备的条件，要求其与阳极的接触好，可形成均匀的薄膜，热稳定，即熔点及玻璃化转变温度高，熔点为大于等于300℃，玻璃化转变温度为大于等于100℃。另外还可以列举离子化电势低，容易注入来自阳极的空穴，空穴迁移率高。
作为用于该目的的材料，至今已报导了铜酞菁等酞菁化合物，聚苯胺、聚噻吩等有机化合物，溅射碳膜，以及氧化钒、氧化钌、氧化钼等金属氧化物。对于空穴注入层，也可以按与空穴传输层相同的方式形成薄膜，但使用无机物时，还可以使用溅射法或电子束蒸镀法、等离子体CVD法。按以上方式形成的阳极缓冲层3的膜厚通常为3～100nm，优选为5～50nm。
阴极7起着向发光层5中注入电子的作用。作为阴极所使用的材料，可以使用用于上述阳极2的材料，但是为了高效地注入电子，优选使用功函数小的金属，可以使用锡、镁、铟、钙、铝、银等适宜的金属或它们的合金。具体而言，可以列举镁-银合金、镁-铟合金、铝-锂合金等低功函数的合金电极。
阴极7的膜厚通常与阳极2相同。为了保护由低功函数金属构成的阴极，可以在其上进一步地层合功函数高、对大气稳定的金属层，从而增加元件的稳定性。为达到此目的，可使用铝、银、铜、镍、铬、金、铂等金属。
另外，在阴极和电子传输层之间插入LiF、MgF2、Li2O等极薄绝缘膜(0.1～5nm)作为电子注入层也是使元件效率得到提高的有效方法。
还有，也可以采取与图1相反的结构，即按阴极7、电子传输层6、发光层5、空穴传输层4、阳极2的顺序在基板1上进行层合，也可以按既述方式在至少一个为高透明性的两片基板间设置本发明的有机EL元件。在此情况下，也可以根据需要追加层或省略层。
在本发明中，有机EL元件完全适用于单一元件、由阵列状配置的结构组成的元件、阳极与阴极呈X-Y矩阵状配置的结构。根据本发明的有机EL元件，通过使发光层含有具有特定骨架的化合物及磷光性的金属络合物，可以获得比以往采用单态发光的元件发光效率更高、驱动稳定性得到大大改善的元件，在全色或多色的屏的应用中都可以发挥优异的性能。
实施例
以下通过合成例及实施例对本发明进行更详细的说明，但只要不超出本发明的主旨，本发明并不局限于以下实施例的记载内容。
合成例1
将醋酸锌二水合物1.6g及三乙胺1.4g溶解在60ml甲醇中。在其中缓慢滴加溶解有2-(2-羟苯基)吡啶2.4g的甲醇溶液20ml，于室温下搅拌4小时。滤出生成的沉淀物，用甲醇进行洗涤。将其进行减压干燥，得到1.6g淡黄色粉末。该化合物是通式(I)中R1～R8全部为H的2-(2-羟苯基)吡啶锌络合物(以下称为Zn(PhPy)2)，对其一部分进行升华精制，用于制作元件。
2-(2-羟苯基)吡啶使用按照特开2000-357588号公报合成的物质。
参考例1
在玻璃基板上采用真空蒸镀法，以真空度为4.0×10-4Pa进行真空蒸镀，以1.0/s的蒸镀速度使Zn(PhPy)2、TAZ、双(8-羟基喹啉)锌(以下称为Znq2)或Alq3形成1000的厚度。将其置于室温的大气中，通过测定结晶时间对薄膜稳定性进行研究。结果示于表4。
表4
| 达到结晶的天数 | |
| TAZ | 小于等于2～3天 |
| Zn(PhPy)2 | 大于等于30天 |
| Znq2 | 大于等于30天 |
| Alq3 | 大于等于30天 |
参考例2
在玻璃基板上仅蒸镀发光层，对是否适于作为Ir(ppy)3的主体材料进行研究。
在玻璃基板上采用真空蒸镀法，在真空度为4.0×10-4Pa的条件下从不同的蒸镀源蒸镀Zn(PhPy)2和Ir(ppy)3，形成Ir(ppy)3浓度为7.0％的500厚的薄膜。另外，按同样的方式将薄膜主成分改为TAZ、Znq2及Alq3来制作薄膜。
用荧光测定装置评价所制成的薄膜。激发波长为Zn(PhPy)2、TAZ、Znq2或Alq3的最大吸收波长，观察此时发出的光。结果示于表5。
表5
| 来自Ir(ppy)3的发光 | 来自主体材料的发光 | |
| TAZ | ○ | × |
| Zn(PhPy)2 | ○ | × |
| Znq2 | × | ○ |
| Alq3 | × | ○ |
当使用TAZ或Zn(PhPy)2作为发光层的主体材料时，能量向Ir(ppy)3迁移，产生了磷光，当使用Znq2或Alq3时，能量不向Ir(ppy)3迁移，Znq2或Alq3本身产生了荧光。
实施例1
形成具有以下结构的有机EL元件，即省略图1中的空穴注入层，并追加电子注入层。在形成了由膜厚为150nm的ITO组成的阳极的玻璃基板上，采用真空蒸镀法，在4.0×10-4Pa的真空度下层合各薄膜。首先以1.0/s的蒸镀速度在ITO上形成作为空穴传输层的NPB，厚度为600。
然后从不同的蒸镀源以1.0/s的蒸镀速度同时在空穴传输层上蒸镀Zn(PhPy)2和Ir(ppy)3，形成厚度为250的发光层。此时，Ir(ppy)3的浓度为7.0％。然后以1.0/s的蒸镀速度形成作为电子传输层的Alq3，厚度为500。再以0.5/s的蒸镀速度在电子传输层上形成作为电子注入层的氟化锂(LiF)，厚度为5。最后，以15/s的蒸镀速度在电子注入层上形成作为电极的铝(Al)，厚度为1700，从而制成有机EL元件。
当在得到的有机EL元件上连接外部电源并施加直流电压时，确认其具有如表6所示的发光特性。表6中，辉度、电压及发光效率示出了在10mA/cm2下的值。元件发光光谱的最大波长为517nm，可知获得了相Ir(ppy)3的发光。
实施例2
除了使用HMTPD作为空穴传输层外，按与实施例1相同的方式制作有机EL元件。
比较例1
除了使用TAZ作为发光层的主成分外，按与实施例1相同的方式制作有机EL元件。
比较例2
在图1中，在形成了由膜厚为150nm的ITO组成的阳极的玻璃基板上，采用真空蒸镀法，在4.0×10-4pa的真空度下层合各薄膜。首先以1.0/s在ITO上形成作为空穴注入层的铜酞菁(CuPc)，厚度为250。然后，以1.0/s的蒸镀速度形成作为空穴传输层的NPB，厚度为450。
然后以1.0/s的蒸镀速度在空穴传输层上形成作为发光层兼电子传输层的Alq3，厚度为600。再以0.5/s的蒸镀速度在电子传输层上形成作为电子注入层的氟化锂(LiF)，厚度为5。最后，以15/s的蒸镀速度在电子注入层上形成作为电极的铝(Al)，厚度为1700，从而制成有机EL元件。测定结果示于表6。
表6
| 辉度(cd/m2) | 电压(V) | 视觉发光效率(1m/W) | |
| 实施例1 | 1320 | 8.2 | 5.1 |
| 实施例2 | 1710 | 12.6 | 4.3 |
| 比较例1 | 1270 | 9.5 | 4.2 |
| 比较例2 | 347 | 9.7 | 1.1 |
本发明的有机电致发光元件使得可以在低电压下进行高辉度、高效率的发光，而且可以获得在高温保存时劣化小的元件。因此，可以将本发明的有机电致发光元件应用于平板显示器(例如OA计算机用或壁挂电视)、车载显示元件、便携电话显示及利用了面发光体的特征的光源(例如复印机光源、液晶显示器及仪表类的背光光源)、显示板、标识灯，本发明有很高的技术价值。
Claims (3)
1、有机电致发光元件，在基板上层合阳极、含有空穴传输层、发光层和电子传输层的有机层以及阴极而形成，在发光层与阳极之间具有空穴传输层，在发光层与阴极之间具有电子传输层，其特征在于：发光层含有作为主体材料的下述通式(I)所示的化合物，以及作为客体材料的含有选自钌、铑、钯、银、铼、锇、铱、铂及金中至少一种金属的有机金属络合物，
式中，R1～R8各自独立地表示氢原子、烷基、芳烷基、链烯基、氰基、氨基、酰胺基、烷氧羰基、羧基、烷氧基、可具有取代基的芳香族烃基或可具有取代基的芳香族杂环基。
2、权利要求1所述的有机电致发光元件，其中空穴传输层含有具有至少2个稠环芳基的三芳基胺二聚体，三芳基胺二聚体为下述通式(II)所示的化合物，
式中，Ar1及Ar2为碳原子数为6～14的1价芳基，但至少一方为碳原子数10～14的具有稠环结构的芳基，Ar3为碳原子数为6～14的2价芳基。
3、权利要求1或2所述的有机电致发光元件，其中客体材料为发绿色磷光性的三(2-苯基吡啶)铱络合物。
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| JP3475620B2 (ja) * | 1995-12-25 | 2003-12-08 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| US6004685A (en) * | 1997-12-23 | 1999-12-21 | Hewlett-Packard Company & The Board Of Regents Of The University Of Texas System | LED doped with periflanthene for efficient red emission |
| US6830828B2 (en) * | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
| JP2000357588A (ja) * | 1999-06-11 | 2000-12-26 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
| JP4039023B2 (ja) * | 2000-10-04 | 2008-01-30 | 三菱化学株式会社 | 有機電界発光素子 |
| US6893743B2 (en) * | 2000-10-04 | 2005-05-17 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
| TW518909B (en) * | 2001-01-17 | 2003-01-21 | Semiconductor Energy Lab | Luminescent device and method of manufacturing same |
| JP2002305083A (ja) * | 2001-04-04 | 2002-10-18 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
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2004
- 2004-09-15 US US10/570,873 patent/US20060269780A1/en not_active Abandoned
- 2004-09-16 CN CNB2004800242560A patent/CN100475930C/zh not_active Expired - Fee Related
- 2004-09-16 JP JP2005514170A patent/JP4593470B2/ja not_active Expired - Fee Related
- 2004-09-16 WO PCT/JP2004/013532 patent/WO2005030900A1/ja active Application Filing
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935299B (zh) * | 2007-10-17 | 2013-01-23 | 中国科学院理化技术研究所 | 有机电子传输和/或空穴阻挡材料及其合成方法和用途 |
| CN103840083A (zh) * | 2012-11-23 | 2014-06-04 | 剑桥显示技术有限公司 | 有机发光器件 |
| CN103840083B (zh) * | 2012-11-23 | 2017-03-01 | 剑桥显示技术有限公司 | 有机发光器件 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20060269780A1 (en) | 2006-11-30 |
| KR101099226B1 (ko) | 2011-12-27 |
| KR20060095976A (ko) | 2006-09-05 |
| CN100475930C (zh) | 2009-04-08 |
| WO2005030900A1 (ja) | 2005-04-07 |
| JP4593470B2 (ja) | 2010-12-08 |
| JPWO2005030900A1 (ja) | 2007-11-15 |
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