JP2003077666A - Light emitting element and organic metallic compound - Google Patents
Light emitting element and organic metallic compoundInfo
- Publication number
- JP2003077666A JP2003077666A JP2001263162A JP2001263162A JP2003077666A JP 2003077666 A JP2003077666 A JP 2003077666A JP 2001263162 A JP2001263162 A JP 2001263162A JP 2001263162 A JP2001263162 A JP 2001263162A JP 2003077666 A JP2003077666 A JP 2003077666A
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- layer
- atom
- emitting device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910000765 intermetallic Inorganic materials 0.000 title abstract 4
- 239000010410 layer Substances 0.000 claims abstract description 76
- 239000012044 organic layer Substances 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims description 43
- 150000002902 organometallic compounds Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052718 tin Inorganic materials 0.000 claims description 11
- 229910052732 germanium Inorganic materials 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- -1 etc. Chemical group 0.000 description 64
- 238000000034 method Methods 0.000 description 51
- 125000004432 carbon atom Chemical group C* 0.000 description 47
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
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- 238000005401 electroluminescence Methods 0.000 description 7
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- 238000010438 heat treatment Methods 0.000 description 6
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- 150000004696 coordination complex Chemical class 0.000 description 5
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- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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- 238000010894 electron beam technology Methods 0.000 description 4
- 239000011133 lead Substances 0.000 description 4
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- 229910052737 gold Inorganic materials 0.000 description 3
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- 150000002894 organic compounds Chemical class 0.000 description 3
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- 125000001302 tertiary amino group Chemical group 0.000 description 3
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007733 ion plating Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001451 molecular beam epitaxy Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 238000001771 vacuum deposition Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 description 1
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- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- SULWTXOWAFVWOY-PHEQNACWSA-N 2,3-bis[(E)-2-phenylethenyl]pyrazine Chemical compound C=1C=CC=CC=1/C=C/C1=NC=CN=C1\C=C\C1=CC=CC=C1 SULWTXOWAFVWOY-PHEQNACWSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
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- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical group [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical group CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は発光素子、特に高輝
度で発光効率が高い発光素子に関し、更に該発光素子に
利用できる有機金属化合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light emitting device, particularly to a light emitting device having high brightness and high luminous efficiency, and further to an organometallic compound which can be used for the light emitting device.
【０００２】[0002]
【従来の技術】今日、種々の表示素子に関する研究開発
が活発に行われており、中でも有機エレクトロルミネッ
センス（EL）素子は低電圧で高輝度の発光が可能である
ため有望な表示素子として注目されている。例えば、有
機化合物の蒸着により形成した有機薄膜を有する有機EL
素子が知られている（Applied Physics Letters, 51, 9
13頁, 1987年）。この有機EL素子は電子輸送材料と正孔
輸送材料を積層した構造を有し、従来の単層型素子に比
べて大幅に向上した発光特性を示す。有機EL素子に用い
られる薄膜は上記のように真空蒸着法により形成するこ
とができ、またスパッタ法、CVD法、PVD法、溶剤を用い
た塗布法等の種々の方法を使用することもできる。有機
EL素子の薄膜形成法については、「ORGANIC ELECTROLUM
INESCENT MATERIALS AND DEVICES」（OPA, Amsterdam,
1997）、「有機EL素子とその工業化最前線」（エヌ・テ
ィー・エス, 1998）等、いくつかの成書にも記述されて
いる。しかしながら、従来の発光素子は発光特性が十分
でなく、発光輝度及び発光効率の改良が求められてい
る。2. Description of the Related Art Today, research and development on various display devices are actively carried out. Among them, organic electroluminescence (EL) devices are attracting attention as promising display devices because they can emit light with high brightness at low voltage. ing. For example, an organic EL having an organic thin film formed by vapor deposition of an organic compound
Elements are known (Applied Physics Letters, 51, 9
13 pages, 1987). This organic EL device has a structure in which an electron transport material and a hole transport material are laminated, and exhibits significantly improved light emission characteristics as compared with a conventional single layer device. The thin film used for the organic EL element can be formed by the vacuum deposition method as described above, and various methods such as the sputtering method, the CVD method, the PVD method, and the coating method using a solvent can also be used. Organic
For the thin film formation method for EL devices, see "ORGANIC ELECTROLUM
INESCENT MATERIALS AND DEVICES "(OPA, Amsterdam,
1997), "organic EL device and its forefront of industrialization" (NTS, 1998), etc. However, conventional light emitting devices have insufficient light emitting characteristics, and improvement in light emitting luminance and light emitting efficiency is required.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は優れた
発光効率で高輝度発光する発光素子、並びに該発光素子
に利用できる有機金属化合物を提供することである。SUMMARY OF THE INVENTION It is an object of the present invention to provide a light emitting device that emits light with high brightness with excellent luminous efficiency, and an organometallic compound that can be used in the light emitting device.
【０００４】[0004]
【課題を解決するための手段】上記目的に鑑み鋭意研究
の結果、本発明者は、特定の有機金属化合物を使用した
発光素子は高輝度・高効率発光が可能であることを発見
し、本発明に想到した。As a result of earnest research in view of the above object, the present inventor discovered that a light emitting device using a specific organometallic compound can emit light with high brightness and high efficiency. Invented the invention.
【０００５】即ち、本発明の発光素子は少なくとも発光
層を含む有機層を有し、該有機層が第4B族ヘテロ原子を
含む有機金属化合物を含有することを特徴とする。That is, the light emitting device of the present invention has an organic layer including at least a light emitting layer, and the organic layer contains an organometallic compound containing a Group 4B hetero atom.
【０００６】本発明の発光素子に使用する有機金属化合
物は下記一般式(1)又は(2)で表されることが好ましい。The organometallic compound used in the light emitting device of the present invention is preferably represented by the following general formula (1) or (2).
【化５】
一般式(1)中、X及びYnはそれぞれSi、Ge及びSnからなる
群から選ばれる原子を表し、Pkは水素原子、アルキル
基、アルケニル基、アルキニル基、アリール基又はヘテ
ロ環基を表し、Q1n、Q2n及びQ3nはそれぞれ水素原子、
アルキル基、アルケニル基、アルキニル基、アリール基
又はヘテロ環基を表し、kは０〜３の整数を表し、nは１
〜４の整数を表す。ただし、Pk、Q1n、Q2n及びQ3nが同
時に水素原子になることはない。[Chemical 5] In the general formula (1), X and Y n each represent an atom selected from the group consisting of Si, Ge and Sn, and P k represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group. Where Q 1n , Q 2n and Q 3n are each a hydrogen atom,
Represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, k represents an integer of 0 to 3, and n represents 1
Represents an integer of 4; However, P k , Q 1n , Q 2n and Q 3n do not become hydrogen atoms at the same time.
【化６】
一般式(2)中、ZrはSi、Ge及びSnからなる群から選ばれ
る原子を表し、R1、R2、R 3r及びR4rはそれぞれ水素原
子、アルキル基、アルケニル基、アルキニル基、アリー
ル基又はヘテロ環基を表し、rは３以上の整数を表す。
ただし、R1、R2、R3r及びR4rが同時に水素原子になるこ
とはない。[Chemical 6]
Z in general formula (2)rIs selected from the group consisting of Si, Ge and Sn
R atom1, R2, R 3rAnd R4rIs hydrogen source
Child, alkyl group, alkenyl group, alkynyl group, aryl
Group or a heterocyclic group, and r represents an integer of 3 or more.
However, R1, R2, R3rAnd R4rBecome hydrogen atoms at the same time
Not.
【０００７】本発明の発光素子において、発光層は三重
項励起子から発光する発光材料を含有するのが好まし
く、有機層は少なくとも１種の高分子化合物を含有する
のが好ましい。また、有機層のうち少なくとも１層は塗
布により形成された層であるのが好ましい。In the light emitting device of the present invention, the light emitting layer preferably contains a light emitting material emitting light from triplet excitons, and the organic layer preferably contains at least one polymer compound. Further, it is preferable that at least one of the organic layers is a layer formed by coating.
【０００８】[0008]
【発明の実施の形態】本発明の発光素子は少なくとも発
光層を含む有機層を有する。有機層は第4B族ヘテロ原子
を含む有機金属化合物を含有する。ここで第4B族ヘテロ
原子とは短周期型周期表における第4B族（長周期型周期
表における第14族）のヘテロ原子、即ちケイ素原子Si、
ゲルマニウム原子Ge、スズ原子Sn及び鉛原子Pbのいずれ
かを指す。また、本発明において「第4B族ヘテロ原子を
含む有機金属化合物」とは、第4B族ヘテロ原子から選ば
れる金属原子（Si、Ge、Sn及びPbのいずれか）又はその
イオンに有機原子団中の炭素原子が直接結合している化
合物を意味する。BEST MODE FOR CARRYING OUT THE INVENTION The light emitting device of the present invention has an organic layer including at least a light emitting layer. The organic layer contains an organometallic compound containing a Group 4B heteroatom. Here, the group 4B heteroatom is a heteroatom of group 4B in the short periodic table (group 14 in the long periodic table), that is, a silicon atom Si,
It means any one of germanium atom Ge, tin atom Sn and lead atom Pb. Further, in the present invention, "organometallic compound containing a Group 4B heteroatom" means a metal atom selected from Group 4B heteroatoms (Si, Ge, Sn and Pb) or an ion thereof in an organic atomic group. Means a compound in which the carbon atoms of are directly bonded.
【０００９】上記有機金属化合物は下記一般式(1)で表
されることが好ましい。The organometallic compound is preferably represented by the following general formula (1).
【化７】 [Chemical 7]
【００１０】一般式(1)中、X及びYnはそれぞれSi、Ge及
びSnからなる群から選ばれる原子を表し、Pkは水素原
子、アルキル基、アルケニル基、アルキニル基、アリー
ル基又はヘテロ環基を表し、Q1n、Q2n及びQ3nはそれぞ
れ水素原子、アルキル基、アルケニル基、アルキニル
基、アリール基又はヘテロ環基を表し、kは０〜３の整
数を表し、nは１〜４の整数を表す。ただし、Pk、Q1n、
Q2n及びQ3nが同時に水素原子になることはない。In the general formula (1), X and Y n each represent an atom selected from the group consisting of Si, Ge and Sn, and P k is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or hetero. Represents a cyclic group, Q 1n , Q 2n and Q 3n each represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, k represents an integer of 0 to 3, and n represents 1 to Represents an integer of 4. Where P k , Q 1n ,
Q 2n and Q 3n cannot be hydrogen atoms at the same time.
【００１１】上記有機金属化合物は下記一般式(2)で表
されることも好ましい。The organometallic compound is also preferably represented by the following general formula (2).
【化８】 [Chemical 8]
【００１２】一般式(2)中、ZrはSi、Ge及びSnからなる
群から選ばれる原子を表し、R1、R2、R3r及びR4rはそれ
ぞれ水素原子、アルキル基、アルケニル基、アルキニル
基、アリール基又はヘテロ環基を表し、rは３以上の整
数を表す。ただし、R1、R2、R 3r及びR4rが同時に水素原
子になることはない。In the general formula (2), ZrConsists of Si, Ge and Sn
Represents an atom selected from the group, R1, R2, R3rAnd R4rIs it
Hydrogen atom, alkyl group, alkenyl group, alkynyl
Represents a group, an aryl group or a heterocyclic group, and r is an integer of 3 or more.
Represents a number. However, R1, R2, R 3rAnd R4rAt the same time hydrogen
You will never be a child.
【００１３】上記Pk、Q1n、Q2n、Q3n、R1、R2、R3r及び
R4rはそれぞれ更に置換基を有してよく、その例として
はハロゲン原子（例えばフッ素原子、塩素原子、臭素原
子、ヨウ素原子等）、シアノ基、ホルミル基、アルキル
基（好ましくは炭素数１〜30、より好ましくは炭素数１
〜15であり、例えばメチル基、t-ブチル基、シクロヘキ
シル基等）、アルケニル基（好ましくは炭素数２〜30、
より好ましくは炭素数２〜15であり、例えばビニル基、
1-プロペニル基、1-ブテン-2-イル基、シクロヘキセン-
1-イル基等）、アルキニル基（好ましくは炭素数２〜3
0、より好ましくは炭素数２〜15であり、例えばエチニ
ル基、1-プロピニル基等）、アリール基（好ましくは炭
素数６〜30、より好ましくは炭素数６〜15であり、例え
ばフェニル基、トリル基、キシリル基、ナフチル基、ビ
フェニリル基、ピレニル基等）、ヘテロ環基（好ましく
は炭素数２〜30、より好ましくは炭素数２〜15であり、
ヘテロ原子として窒素原子、酸素原子、硫黄原子等を含
み、好ましくは５又は６員環であり、他の環と縮合して
いてもよく、例えばピリジル基、ピペリジル基、オキサ
ゾリル基、オキサジアゾリル基、テトラヒドロフリル
基、チエニル基等）、１〜３級アミノ基（例えばアミノ
基、アルキルアミノ基、アリールアミノ基、ジアルキル
アミノ基、ジアリールアミノ基、アルキルアリールアミ
ノ基、ヘテロ環アミノ基、ビスヘテロ環アミノ基等。好
ましくは３級アミノ基であり、その場合好ましくは炭素
数１〜30、より好ましくは炭素数１〜16であり、例えば
ジメチルアミノ基、ジフェニルアミノ基、フェニルナフ
チルアミノ基等）、イミノ基（-CR11=NR12又は-N=CR13R
14で表される基。ここでR11〜R14はそれぞれ水素原子、
アルキル基、アリール基、ヘテロ環基、アルコキシ基、
アリールオキシ基又は１〜３級アミノ基を表す。好まし
くは炭素数１〜30、より好ましくは炭素数１〜15であ
る。）、アルコキシ基（好ましくは炭素数１〜30、より
好ましくは炭素数１〜15であり、例えばメトキシ基、エ
トキシ基、シクロヘキシルオキシ基等）、アリールオキ
シ基（好ましくは炭素数６〜30、より好ましくは炭素数
６〜15であり、例えばフェノキシ基、1-ナフトキシ基、
4-フェニルフェノキシ基等）、アルキルチオ基（好まし
くは炭素数１〜30、より好ましくは炭素数１〜15であ
り、例えばメチルチオ基、エチルチオ基、シクロヘキシ
ルチオ基等）、アリールチオ基（好ましくは炭素数６〜
30、より好ましくは炭素数６〜15であり、例えばフェニ
ルチオ基、トリルチオ基等）、カルボンアミド基（好ま
しくは炭素数１〜30、より好ましくは炭素数１〜15であ
り、例えばアセトアミド基、ベンゾイルアミド基、N-メ
チルベンゾイルアミド基等）、スルホンアミド基（好ま
しくは炭素数１〜30、より好ましくは炭素数１〜15であ
り、例えばメタンスルホンアミド基、ベンゼンスルホン
アミド基、p-トルエンスルホンアミド基等）、カルバモ
イル基（好ましくは炭素数１〜30、より好ましくは炭素
数１〜15であり、例えば無置換のカルバモイル基、メチ
ルカルバモイル基、ジメチルカルバモイル基、フェニル
カルバモイル基、ジフェニルカルバモイル基、ジオクチ
ルカルバモイル基等）、スルファモイル基（好ましくは
炭素数１〜30、より好ましくは炭素数１〜15であり、例
えば無置換のスルファモイル基、メチルスルファモイル
基、ジメチルスルファモイル基、フェニルスルファモイ
ル基、ジフェニルスルファモイル基、ジオクチルスルフ
ァモイル基等）、アルキルカルボニル基（好ましくは炭
素数１〜30、より好ましくは炭素数１〜15であり、例え
ばアセチル基、プロピオニル基、ブチロイル基、ラウロ
イル基等）、アリールカルボニル基（好ましくは炭素数
６〜30、より好ましくは炭素数６〜15であり、例えばベ
ンゾイル基、ナフトイル基等）、アルキルスルホニル基
（好ましくは炭素数１〜30、より好ましくは炭素数１〜
15であり、例えばメタンスルホニル基、エタンスルホニ
ル基等）、アリールスルホニル基（好ましくは炭素数６
〜30、より好ましくは炭素数６〜15であり、例えばベン
ゼンスルホニル基、p-トルエンスルホニル基、1-ナフタ
レンスルホニル基等）、アルコキシカルボニル基（好ま
しくは炭素数１〜30、より好ましくは炭素数１〜15であ
り、例えばメトキシカルボニル基、エトキシカルボニル
基、ブトキシカルボニル基等）、アリールオキシカルボ
ニル基（好ましくは炭素数６〜30、より好ましくは炭素
数６〜15であり、例えばフェノキシカルボニル基、1-ナ
フトキシカルボニル基等）、アルキルカルボニルオキシ
基（好ましくは炭素数１〜30、より好ましくは炭素数１
〜15であり、例えばアセトキシ基、プロピオニルオキシ
基、ブチロイルオキシ基等）、アリールカルボニルオキ
シ基（好ましくは炭素数６〜30、より好ましくは炭素数
６〜15であり、例えばベンゾイルオキシ基、1-ナフトイ
ルオキシ基等）、ウレタン基（好ましくは炭素数１〜3
0、より好ましくは炭素数１〜15であり、例えばメトキ
シカルボンアミド基、フェノキシカルボンアミド基、メ
チルアミノカルボンアミド基等）、ウレイド基（好まし
くは炭素数１〜30、より好ましくは炭素数１〜15であ
り、例えばメチルアミノカルボンアミド基、ジメチルア
ミノカルボンアミド基、ジフェニルアミノカルボンアミ
ド基等）、炭酸エステル基（好ましくは炭素数１〜30、
より好ましくは炭素数１〜15であり、例えばメトキシカ
ルボニルオキシ基、フェノキシカルボニルオキシ基等）
等が挙げられる。これらの置換基は更に置換されていて
もよい。The above P k , Q 1n , Q 2n , Q 3n , R 1 , R 2 , R 3r and
R 4r may further have a substituent, and examples thereof include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), a cyano group, a formyl group, an alkyl group (preferably having a carbon number of 1 to 1). 30, more preferably 1 carbon
To 15 and, for example, methyl group, t-butyl group, cyclohexyl group, etc., alkenyl group (preferably having 2 to 30 carbon atoms,
More preferably has 2 to 15 carbon atoms, for example a vinyl group,
1-propenyl group, 1-buten-2-yl group, cyclohexene-
1-yl group, etc., alkynyl group (preferably having 2 to 3 carbon atoms)
0, more preferably having 2 to 15 carbon atoms, for example, ethynyl group, 1-propynyl group, etc., aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, for example, phenyl group, A tolyl group, a xylyl group, a naphthyl group, a biphenylyl group, a pyrenyl group, etc.), a heterocyclic group (preferably having 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms,
It contains a nitrogen atom, an oxygen atom, a sulfur atom or the like as a hetero atom, and is preferably a 5- or 6-membered ring and may be condensed with another ring, for example, a pyridyl group, a piperidyl group, an oxazolyl group, an oxadiazolyl group, tetrahydro. Furyl group, thienyl group, etc., primary to tertiary amino group (for example, amino group, alkylamino group, arylamino group, dialkylamino group, diarylamino group, alkylarylamino group, heterocyclic amino group, bisheterocyclic amino group, etc. Preferably, it is a tertiary amino group, in which case it preferably has 1 to 30 carbon atoms, more preferably 1 to 16 carbon atoms, and examples thereof include dimethylamino group, diphenylamino group, phenylnaphthylamino group, etc., imino group ( -CR 11 = NR 12 or -N = CR 13 R
The group represented by 14 . Here, R 11 to R 14 are hydrogen atoms,
Alkyl group, aryl group, heterocyclic group, alkoxy group,
It represents an aryloxy group or a primary to tertiary amino group. It preferably has 1 to 30 carbon atoms, and more preferably 1 to 15 carbon atoms. ), An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, for example, a methoxy group, an ethoxy group, a cyclohexyloxy group, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, and It preferably has 6 to 15 carbon atoms, and includes, for example, a phenoxy group, a 1-naphthoxy group,
4-phenylphenoxy group, etc., alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, for example, methylthio group, ethylthio group, cyclohexylthio group, etc.), arylthio group (preferably having carbon number) 6 ~
30, more preferably having 6 to 15 carbon atoms, such as phenylthio group, tolylthio group, etc., carbonamido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, eg, acetamido group, benzoyl) Amido group, N-methylbenzoylamide group, etc.), sulfonamide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms), for example, methanesulfonamide group, benzenesulfonamide group, p-toluenesulfone Amide group, etc., carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, for example, an unsubstituted carbamoyl group, a methylcarbamoyl group, a dimethylcarbamoyl group, a phenylcarbamoyl group, a diphenylcarbamoyl group, Dioctylcarbamoyl group, etc., sulfamoyl group (preferably having 1 to 30 carbon atoms, more preferably C1-C15, for example, unsubstituted sulfamoyl group, methylsulfamoyl group, dimethylsulfamoyl group, phenylsulfamoyl group, diphenylsulfamoyl group, dioctylsulfamoyl group, etc.), alkyl Carbonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, for example, acetyl group, propionyl group, butyroyl group, lauroyl group, etc.), arylcarbonyl group (preferably having 6 to 30 carbon atoms, more It preferably has 6 to 15 carbon atoms, and for example, a benzoyl group, a naphthoyl group, etc., an alkylsulfonyl group (preferably 1 to 30 carbon atoms, more preferably 1 to 10 carbon atoms).
15 and, for example, methanesulfonyl group, ethanesulfonyl group, etc., arylsulfonyl group (preferably having 6 carbon atoms)
To 30, more preferably 6 to 15 carbon atoms, such as benzenesulfonyl group, p-toluenesulfonyl group, 1-naphthalenesulfonyl group, etc., alkoxycarbonyl group (preferably 1 to 30 carbon atoms, more preferably carbon number) 1 to 15, for example, methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group, etc., aryloxycarbonyl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms, for example, phenoxycarbonyl group, 1-naphthoxycarbonyl group, etc., alkylcarbonyloxy group (preferably having 1 to 30 carbon atoms, more preferably 1 carbon atom)
~ 15, for example, acetoxy group, propionyloxy group, butyroyloxy group, etc., arylcarbonyloxy group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 15 carbon atoms, for example, benzoyloxy group, 1-naphtho Iloxy group, etc., urethane group (preferably having 1 to 3 carbon atoms)
0, more preferably having 1 to 15 carbon atoms, for example, a methoxycarbonamide group, a phenoxycarbonamide group, a methylaminocarbonamide group, etc.), a ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms). 15, for example, methylaminocarbonamide group, dimethylaminocarbonamide group, diphenylaminocarbonamide group, etc., carbonic acid ester group (preferably having 1 to 30 carbon atoms,
More preferably, it has 1 to 15 carbon atoms, for example, methoxycarbonyloxy group, phenoxycarbonyloxy group, etc.)
Etc. These substituents may be further substituted.
【００１４】本発明の発光素子に用いる有機金属化合物
は、ポリマー化合物であってもよい。このポリマー化合
物はラジカル重合、イオン重合、縮重合、開環重合等の
重合方法により調製できる。これらの重合法については
大津・木下共著「高分子合成の実験法」（化学同人刊、
1972年）等に詳細が記載されている。このようなポリマ
ー化合物の平均分子量（Mw）は好ましくは1000〜100000
00、より好ましくは2000〜1000000、特に好ましくは500
0〜500000である。The organometallic compound used in the light emitting device of the present invention may be a polymer compound. This polymer compound can be prepared by a polymerization method such as radical polymerization, ionic polymerization, polycondensation and ring-opening polymerization. Regarding these polymerization methods, Otsu and Kinoshita, "Experimental Method of Polymer Synthesis" (published by Kagaku Dojin,
(1972) and the like are described in detail. The average molecular weight (Mw) of such a polymer compound is preferably 10,000 to 100,000.
00, more preferably 2000 to 100000, and particularly preferably 500.
It is 0 to 500000.
【００１５】本発明の発光素子に用いる有機金属化合物
は単独で使用しても他の化合物と併用してもよい。併用
する他の化合物は有機化合物であっても無機化合物であ
ってのよく、また低分子化合物であってもポリマーであ
ってもよい。The organometallic compounds used in the light emitting device of the present invention may be used alone or in combination with other compounds. The other compound used in combination may be an organic compound or an inorganic compound, and may be a low molecular weight compound or a polymer.
【００１６】上記有機金属化合物は正孔注入材料、正孔
輸送材料、発光材料、電子輸送材料、電子注入材料等と
して機能するものであってよく、複数の機能を併せ持っ
ていてもよい。有機金属化合物は正孔注入材料又は正孔
輸送材料として使用するのが好ましく、正孔注入材料と
して使用するのがより好ましい。本発明の発光素子に用
いる有機金属化合物の好ましい具体例を以下に示すが、
本発明はそれらによって限定されるものではない。The organometallic compound may function as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, or the like, and may have a plurality of functions. The organometallic compound is preferably used as a hole injection material or a hole transport material, and more preferably used as a hole injection material. Preferred specific examples of the organometallic compound used in the light emitting device of the present invention are shown below,
The present invention is not limited by them.
【００１７】[0017]
【化９】 [Chemical 9]
【００１８】[0018]
【化10】 [Chemical 10]
【００１９】[0019]
【化11】 [Chemical 11]
【００２０】本発明の発光素子は通常、一対の電極（陽
極及び陰極）間に少なくとも発光層を含む有機層（有機
化合物薄膜）を有する。上記第4B族ヘテロ原子を含む有
機金属化合物は発光層及び／又は他の有機層に含有され
てよい。有機層は少なくとも１種の高分子化合物を含有
するのが好ましい。有機金属化合物を含有する層の形成
方法は特に限定されず、抵抗加熱蒸着法、電子ビーム
法、スパッタリング法、分子積層法、コーティング法、
インクジェット法等の方法が使用可能である。中でも、
素子の特性及び製造面から抵抗加熱蒸着法及びコーティ
ング法が好ましい。また、有機層のうち少なくとも１層
は塗布により形成された層であるのが好ましい。The light emitting device of the present invention usually has an organic layer (organic compound thin film) including at least a light emitting layer between a pair of electrodes (anode and cathode). The organometallic compound containing a Group 4B heteroatom may be contained in the light emitting layer and / or another organic layer. The organic layer preferably contains at least one polymer compound. The method for forming the layer containing the organometallic compound is not particularly limited, and the resistance heating vapor deposition method, the electron beam method, the sputtering method, the molecular lamination method, the coating method,
A method such as an inkjet method can be used. Above all,
The resistance heating vapor deposition method and the coating method are preferable in terms of device characteristics and manufacturing. Further, it is preferable that at least one of the organic layers is a layer formed by coating.
【００２１】本発明の発光素子は発光層の他に正孔注入
層、正孔輸送層、電子注入層、電子輸送層、保護層等を
有してもよく、またこれらの各層はそれぞれ他の機能を
備えたものであってもよい。第4B族ヘテロ原子を含む有
機金属化合物はこれらの層のいずれに含有されていても
よいが、正孔注入層又は正孔輸送層に含有されるのが好
ましく、正孔注入層に含有されるのがより好ましい。以
下、各層について詳述する。The light emitting device of the present invention may have a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, a protective layer and the like in addition to the light emitting layer. It may have a function. The organometallic compound containing a Group 4B heteroatom may be contained in any of these layers, but is preferably contained in the hole injection layer or the hole transport layer, and contained in the hole injection layer. Is more preferable. Hereinafter, each layer will be described in detail.
【００２２】(A)陽極
陽極は正孔注入層、正孔輸送層、発光層等に正孔を供給
するものである。陽極を形成する材料としては、金属、
合金、金属酸化物、電気伝導性化合物、これらの混合物
等を用いることができ、好ましくは仕事関数が４eV以上
の材料を用いる。具体例としては、金属（金、銀、クロ
ム、ニッケル等）、導電性金属酸化物（酸化スズ、酸化
亜鉛、酸化インジウム、酸化インジウムスズ（ITO）
等）、これら金属と導電性金属酸化物との混合物又は積
層物、無機導電性物質（ヨウ化銅、硫化銅等）、有機導
電性材料（ポリアニリン、ポリチオフェン、ポリピロー
ル等）及びこれらとITOとの積層物等が挙げられる。陽
極は導電性金属酸化物からなるのが好ましく、生産性、
高導電性、透明性等の観点からITOが特に好ましい。(A) Anode The anode supplies holes to the hole injection layer, the hole transport layer, the light emitting layer and the like. As a material for forming the anode, a metal,
An alloy, a metal oxide, an electrically conductive compound, a mixture thereof, or the like can be used, and a material having a work function of 4 eV or more is preferably used. Specific examples include metals (gold, silver, chromium, nickel, etc.), conductive metal oxides (tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO)).
Etc.), mixtures or laminates of these metals and conductive metal oxides, inorganic conductive materials (copper iodide, copper sulfide, etc.), organic conductive materials (polyaniline, polythiophene, polypyrrole, etc.) and these and ITO Examples include laminated materials. The anode is preferably made of a conductive metal oxide, productivity,
ITO is particularly preferable from the viewpoint of high conductivity and transparency.
【００２３】陽極の形成法は用いる材料に応じて適宜選
択すればよく、例えばITOの場合、電子ビーム法、スパ
ッタリング法、抵抗加熱蒸着法、化学反応法（ゾル−ゲ
ル法等）、酸化インジウムスズ分散物の塗布等の方法を
用いることができる。陽極に洗浄等の処理を施すことに
より、発光素子の駆動電圧を下げたり、発光効率を高め
たりすることも可能である。例えばITOからなる陽極の
場合、UV-オゾン処理、プラズマ処理等が効果的であ
る。陽極のシート抵抗は数百Ω／□以下とするのが好ま
しい。陽極の膜厚は材料に応じて適宜選択可能である
が、通常10nm〜５μmとするのが好ましく、50nm〜１μm
とするのがより好ましく、100〜500nmとするのが特に好
ましい。The method of forming the anode may be appropriately selected according to the material used. For example, in the case of ITO, electron beam method, sputtering method, resistance heating vapor deposition method, chemical reaction method (sol-gel method, etc.), indium tin oxide. A method such as coating the dispersion can be used. By subjecting the anode to a treatment such as cleaning, it is possible to lower the drive voltage of the light emitting element or increase the light emission efficiency. For example, in the case of an anode made of ITO, UV-ozone treatment, plasma treatment, etc. are effective. The sheet resistance of the anode is preferably several hundred Ω / □ or less. The film thickness of the anode can be appropriately selected depending on the material, but normally, it is preferably 10 nm to 5 μm, and 50 nm to 1 μm
Is more preferable, and 100 to 500 nm is particularly preferable.
【００２４】陽極は通常、ソーダライムガラス、無アル
カリガラス、透明樹脂等からなる基板上に形成する。ガ
ラス基板の場合、ガラスからの溶出イオンを低減するた
めには無アルカリガラスを用いるのが好ましい。ソーダ
ライムガラス基板を用いる場合は、予めその表面にシリ
カ等のバリアコートを形成するのが好ましい。基板の厚
さは、機械的強度を保つのに十分であれば特に制限はな
いが、ガラス基板の場合は通常0.2mm以上、好ましくは
0.7mm以上とする。The anode is usually formed on a substrate made of soda lime glass, non-alkali glass, transparent resin or the like. In the case of a glass substrate, it is preferable to use non-alkali glass in order to reduce the ions eluted from the glass. When using a soda lime glass substrate, it is preferable to previously form a barrier coat of silica or the like on the surface thereof. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but in the case of a glass substrate, it is usually 0.2 mm or more, preferably
It should be 0.7 mm or more.
【００２５】(B)陰極
陰極は電子注入層、電子輸送層、発光層等に電子を供給
するものである。陰極の材料としては、金属、合金、金
属ハロゲン化物、金属酸化物、電気伝導性化合物、これ
らの混合物等を用いることができ、発光層等の隣接する
層との密着性やイオン化ポテンシャル、安定性等を考慮
して選択すればよい。具体例としては、アルカリ金属
（Li、Na、K、Cs等）及びそのフッ化物、アルカリ土類
金属（Mg、Ca等）及びそのフッ化物、金、銀、鉛、アル
ミニウム、ナトリウム及びカリウムを含む合金及び混合
金属、リチウム及びアルミニウムを含む合金及び混合金
属、マグネシウム及び銀を含む合金及び混合金属、希土
類金属（インジウム、イッテリビウム等）、それらの混
合物等が挙げられる。陰極は仕事関数が４eV以下の材料
からなるのが好ましく、アルミニウム、リチウムとアル
ミニウムを含む合金又は混合金属、或いはマグネシウム
と銀を含む合金又は混合金属からなるのがより好まし
い。(B) Cathode The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer and the like. As a material of the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, a mixture thereof, or the like can be used, and adhesion, ionization potential, stability with an adjacent layer such as a light emitting layer can be used. It may be selected in consideration of the above. Specific examples include alkali metals (Li, Na, K, Cs, etc.) and their fluorides, alkaline earth metals (Mg, Ca, etc.) and their fluorides, gold, silver, lead, aluminum, sodium and potassium. Examples thereof include alloys and mixed metals, alloys and mixed metals containing lithium and aluminum, alloys and mixed metals containing magnesium and silver, rare earth metals (indium, ytterbium, etc.), and mixtures thereof. The cathode is preferably made of a material having a work function of 4 eV or less, more preferably aluminum, an alloy or mixed metal containing lithium and aluminum, or an alloy or mixed metal containing magnesium and silver.
【００２６】陰極は、上記のような材料からなる単層構
造であっても、上記材料からなる層を含む積層構造であ
ってもよい。陰極は電子ビーム法、スパッタリング法、
抵抗加熱蒸着法、コーティング法等により形成すること
ができる。蒸着法の場合、材料を単独で蒸着すること
も、二種以上の材料を同時に蒸着することもできる。合
金電極を形成する場合は、複数の金属を同時蒸着して形
成することが可能であり、また予め調整した合金を蒸着
してもよい。陰極のシート抵抗は数百Ω／□以下とする
のが好ましい。陰極の膜厚は材料に応じて適宜選択可能
であるが、通常10nm〜５μmとするのが好ましく、50nm
〜１μmとするのがより好ましく、100nm〜１μmとする
のが特に好ましい。The cathode may have a single layer structure made of the above materials or a laminated structure containing layers made of the above materials. The cathode is an electron beam method, a sputtering method,
It can be formed by a resistance heating vapor deposition method, a coating method, or the like. In the case of the vapor deposition method, the material can be vapor-deposited alone, or two or more materials can be vapor-deposited simultaneously. When forming an alloy electrode, it is possible to form a plurality of metals by vapor deposition at the same time, or a previously adjusted alloy may be deposited. The sheet resistance of the cathode is preferably several hundred Ω / □ or less. The thickness of the cathode can be appropriately selected according to the material, but normally, it is preferably 10 nm to 5 μm, 50 nm
˜1 μm is more preferred, and 100 nm to 1 μm is especially preferred.
【００２７】(C)正孔注入層及び正孔輸送層
正孔注入層及び正孔輸送層に用いる材料は、陽極から正
孔を注入する機能、正孔を輸送する機能、及び陰極から
注入された電子を障壁する機能のいずれかを有している
ものであればよい。その具体例としては、カルバゾー
ル、トリアゾール、オキサゾール、オキサジアゾール、
イミダゾール、ポリアリールアルカン、ピラゾリン、ピ
ラゾロン、フェニレンジアミン、アリールアミン、アミ
ノ置換カルコン、スチリルアントラセン、フルオレノ
ン、ヒドラゾン、スチルベン、シラザン、芳香族第三級
アミン化合物、スチリルアミン化合物、芳香族ジメチリ
ディン系化合物、ポルフィリン系化合物、ポリシラン系
化合物、ポリ(N-ビニルカルバゾール)、アニリン系共重
合体、チオフェンオリゴマーやポリチオフェン等の導電
性高分子、これらの誘導体等が挙げられる。(C) Hole Injection Layer and Hole Transport Layer The materials used for the hole injection layer and hole transport layer are the function of injecting holes from the anode, the function of transporting holes, and the function of injecting from the cathode. It may have any of the functions of blocking electrons. Specific examples thereof include carbazole, triazole, oxazole, oxadiazole,
Imidazoles, polyarylalkanes, pyrazolines, pyrazolones, phenylenediamines, arylamines, amino-substituted chalcones, styrylanthracenes, fluorenones, hydrazones, stilbenes, silazanes, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidyne compounds, porphyrins Examples thereof include system compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, conductive polymers such as thiophene oligomers and polythiophenes, and derivatives thereof.
【００２８】正孔注入層及び正孔輸送層は１種又は２種
以上の上記材料からなる単層構造であってもよいし、同
一組成又は異種組成の複数層からなる多層構造であって
もよい。正孔注入層及び正孔輸送層の形成方法として
は、真空蒸着法、LB法、上記材料を溶媒中に溶解又は分
散させてコーティングする方法（スピンコート法、キャ
スト法、ディップコート法等）、インクジェット法等が
用いられる。コーティング法の場合、上記材料を樹脂成
分と共に溶解又は分散させて塗布液を調製してもよく、
該樹脂成分としては、ポリ塩化ビニル、ポリカーボネー
ト、ポリスチレン、ポリメチルメタクリレート、ポリブ
チルメタクリレート、ポリエステル、ポリスルホン、ポ
リフェニレンオキシド、ポリブタジエン、ポリ(N-ビニ
ルカルバゾール)、炭化水素樹脂、ケトン樹脂、フェノ
キシ樹脂、ポリアミド、エチルセルロース、ポリ酢酸ビ
ニル、ABS樹脂、ポリウレタン、メラミン樹脂、不飽和
ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリ
コン樹脂等が使用できる。正孔注入層及び正孔輸送層の
膜厚は特に限定されないが、通常１nm〜５μmとするの
が好ましく、５nm〜１μmとするのがより好ましく、10
〜500nmとするのが特に好ましい。The hole injecting layer and the hole transporting layer may have a single-layer structure composed of one or more of the above materials, or a multi-layer structure composed of a plurality of layers having the same composition or different compositions. Good. As a method for forming the hole injection layer and the hole transport layer, a vacuum deposition method, an LB method, a method of coating by dissolving or dispersing the above material in a solvent (spin coating method, casting method, dip coating method, etc.), An inkjet method or the like is used. In the case of the coating method, the above material may be dissolved or dispersed together with the resin component to prepare a coating solution,
As the resin component, polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide , Ethyl cellulose, polyvinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin and the like can be used. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm,
It is particularly preferable that the thickness is ˜500 nm.
【００２９】(D)発光層
発光素子に電界を印加すると、発光層において陽極、正
孔注入層又は正孔輸送層から注入された正孔と、陰極、
電子注入層又は電子輸送層から注入された電子とが再結
合し、光を発する。発光層をなす材料は、電界印加時に
陽極等から正孔を受け取る機能、陰極等から電子を受け
取る機能、電荷を移動させる機能、及び正孔と電子の再
結合の場を提供して発光させる機能を有する層を形成す
ることができるものであれば特に限定されない。発光層
の材料は一重項励起子及び三重項励起子のいずれから発
光するものであってもよく、またその両者から発光する
ものであってもよく、例えばベンゾオキサゾール、ベン
ゾイミダゾール、ベンゾチアゾール、スチリルベンゼ
ン、ポリフェニル、ジフェニルブタジエン、テトラフェ
ニルブタジエン、ナフタルイミド、クマリン、ペリレ
ン、ペリノン、オキサジアゾール、アルダジン、ピラリ
ジン、シクロペンタジエン、ビススチリルアントラセ
ン、キナクリドン、ピロロピリジン、チアジアゾロピリ
ジン、シクロペンタジエン、スチリルアミン、芳香族ジ
メチリディン化合物、金属錯体（8-キノリノール誘導体
の金属錯体、希土類錯体、遷移金属錯体等）、高分子発
光材料（ポリチオフェン、ポリフェニレン、ポリフェニ
レンビニレン等）、これらの誘導体等が使用できる。発
光層は単一材料で形成されてもよいし、複数の材料で形
成されてもよい。(D) Light-Emitting Layer When an electric field is applied to the light-emitting element, the holes injected from the anode, the hole injection layer or the hole transport layer in the light emitting layer, the cathode,
The electrons injected from the electron injection layer or the electron transport layer are recombined with each other to emit light. The material forming the light-emitting layer has a function of receiving holes from an anode or the like when an electric field is applied, a function of receiving electrons from a cathode or the like, a function of moving charges, and a function of providing a field for recombination of holes and electrons to emit light. There is no particular limitation as long as it can form a layer having The material of the light emitting layer may emit light from either singlet excitons or triplet excitons, or may emit light from both of them, for example, benzoxazole, benzimidazole, benzothiazole, styryl. Benzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, perylene, perinone, oxadiazole, aldazine, pyraridine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styryl Amine, aromatic dimethylidin compound, metal complex (metal complex of 8-quinolinol derivative, rare earth complex, transition metal complex, etc.), polymer light emitting material (polythiophene, polyphenylene, polyphenylene vinylene, etc.) These derivatives and the like can be used. The light emitting layer may be formed of a single material or plural materials.
【００３０】本発明の発光素子において、発光層は三重
項励起子から発光する発光材料を含有するのが好まし
い。三重項励起子からの発光を利用した発光素子として
は、イリジウム錯体Ir(ppy)3（Tris-Ortho-Metalated C
omplex of Iridium (III) with2-Phenylpyridine）を用
いた緑色発光素子が報告されている（Applied PhysicsL
etters, 75, 4 (1999)）。この緑色発光素子は外部量子
収率８％を達成しており、従来素子の限界といわれてい
た外部量子収率５％を凌駕している。In the light emitting device of the present invention, the light emitting layer preferably contains a light emitting material which emits light from triplet excitons. A light-emitting device that utilizes light emission from triplet excitons is an iridium complex Ir (ppy) 3 (Tris-Ortho-Metalated C
A green light emitting device using omplex of Iridium (III) with2-Phenylpyridine has been reported (Applied PhysicsL
etters, 75, 4 (1999)). This green light emitting device has achieved an external quantum yield of 8%, which exceeds the external quantum yield of 5%, which was said to be the limit of conventional devices.
【００３１】発光層の形成方法は特に限定されず、抵抗
加熱蒸着法、電子ビーム法、スパッタリング法、分子積
層法、コーティング法（スピンコート法、キャスト法、
ディップコート法等）、インクジェット法、LB法等が使
用可能である。中でも抵抗加熱蒸着法及びコーティング
法が好ましい。発光層の膜厚は特に限定されず、通常１
nm〜５μmとするのが好ましく、５nm〜１μmとするのが
より好ましく、10〜500nmとするのが特に好ましい。The method for forming the light emitting layer is not particularly limited, and the resistance heating vapor deposition method, electron beam method, sputtering method, molecular layering method, coating method (spin coating method, casting method,
The dip coating method, etc.), the inkjet method, the LB method, etc. can be used. Among them, the resistance heating vapor deposition method and the coating method are preferable. The thickness of the light emitting layer is not particularly limited and is usually 1
nm to 5 μm is preferable, 5 nm to 1 μm is more preferable, and 10 to 500 nm is particularly preferable.
【００３２】(E)電子注入層及び電子輸送層
電子注入層及び電子輸送層をなす材料は、陰極から電子
を注入する機能、電子を輸送する機能、並びに陽極から
注入された正孔を障壁する機能のいずれかを有している
ものであればよい。具体例としては、トリアゾール、オ
キサゾール、オキサジアゾール、フルオレノン、アント
ラキノジメタン、アントロン、ジフェニルキノン、チオ
ピランジオキシド、カルボジイミド、フルオレニリデン
メタン、ジスチリルピラジン、ナフタレンやペリレン等
の芳香環を有するテトラカルボン酸無水物、フタロシア
ニン、金属錯体（8-キノリノール誘導体の金属錯体、メ
タルフタロシアニン、ベンゾオキサゾールやベンゾチア
ゾールを配位子とする金属錯体等）、これらの誘導体等
が挙げられる。(E) Electron injection layer and electron transport layer The materials forming the electron injection layer and electron transport layer block the function of injecting electrons from the cathode, the function of transporting electrons, and the holes injected from the anode. Any function may be used as long as it has one of the functions. Specific examples include aromatic rings such as triazole, oxazole, oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, naphthalene and perylene. Tetracarboxylic acid anhydride, phthalocyanine, metal complex (metal complex of 8-quinolinol derivative, metal phthalocyanine, metal complex having benzoxazole or benzothiazole as a ligand, etc.), and derivatives thereof can be mentioned.
【００３３】電子注入層及び電子輸送層は１種又は２種
以上の上記材料からなる単層構造であってもよいし、同
一組成又は異種組成の複数層からなる多層構造であって
もよい。電子注入層及び電子輸送層の形成方法として
は、真空蒸着法、LB法、上記材料を溶媒中に溶解又は分
散させてコーティングする方法（スピンコート法、キャ
スト法、ディップコート法等）、インクジェット法等が
用いられる。コーティング法の場合、上記材料を樹脂成
分と共に溶解又は分散させて塗布液を調製してもよい。
該樹脂成分としては、前述した正孔注入層及び正孔輸送
層の場合と同様のものが使用できる。電子注入層及び電
子輸送層の膜厚は特に限定されず、通常１nm〜５μmと
するのが好ましく、５nm〜１μmとするのがより好まし
く、10〜500nmとするのが特に好ましい。The electron injection layer and the electron transport layer may have a single-layer structure composed of one or more of the above-mentioned materials, or may have a multi-layer structure composed of a plurality of layers having the same composition or different compositions. As a method for forming the electron injection layer and the electron transport layer, a vacuum vapor deposition method, an LB method, a method of dissolving or dispersing the above materials in a solvent and coating (spin coating method, casting method, dip coating method, etc.), inkjet method Etc. are used. In the case of the coating method, the coating liquid may be prepared by dissolving or dispersing the above materials together with the resin component.
As the resin component, the same ones as in the case of the hole injection layer and the hole transport layer described above can be used. The thickness of the electron injection layer and the electron transport layer is not particularly limited, and is usually preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm, and particularly preferably 10 to 500 nm.
【００３４】(F)保護層
保護層は水分、酸素等の素子劣化を促進するものが素子
内に入ることを抑止する機能を有する。保護層の材料と
しては、金属（In、Sn、Pb、Au、Cu、Ag、Al、Ti、Ni
等）、金属酸化物（MgO、SiO、SiO2、Al2O3、GeO、Ni
O、CaO、BaO、Fe2O3、Y2O3、TiO2等）、金属フッ化物
（MgF2、LiF、AlF3、CaF2等）、ポリエチレン、ポリプ
ロピレン、ポリメチルメタクリレート、ポリイミド、ポ
リウレア、ポリテトラフルオロエチレン、ポリクロロト
リフルオロエチレン、ポリジクロロジフルオロエチレ
ン、クロロトリフルオロエチレンとジクロロジフルオロ
エチレンとの共重合体、テトラフルオロエチレンと少な
くとも１種のコモノマーとを含むモノマー混合物を共重
合させて得られる共重合体、共重合主鎖に環状構造を有
する含フッ素共重合体、吸水率１％以上の吸水性物質、
吸水率0.1％以下の防湿性物質等が使用できる。(F) Protective Layer The protective layer has a function of preventing substances, such as water and oxygen, which promote deterioration of the device from entering the device. Materials for the protective layer include metals (In, Sn, Pb, Au, Cu, Ag, Al, Ti, Ni
Etc.), metal oxides (MgO, SiO, SiO 2 , Al 2 O 3 , GeO, Ni)
O, CaO, BaO, Fe 2 O 3 , Y 2 O 3 , TiO 2, etc.), metal fluorides (MgF 2 , LiF, AlF 3 , CaF 2, etc.), polyethylene, polypropylene, polymethylmethacrylate, polyimide, polyurea, Obtained by copolymerizing polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, or a monomer mixture containing tetrafluoroethylene and at least one comonomer. Copolymer, fluorine-containing copolymer having a cyclic structure in the copolymer main chain, water-absorbing substance having a water absorption rate of 1% or more,
A moisture-proof substance with a water absorption rate of 0.1% or less can be used.
【００３５】保護層の形成方法は特に限定されず、真空
蒸着法、スパッタリング法、反応性スパッタリング法、
MBE（分子線エピタキシ）法、クラスターイオンビーム
法、イオンプレーティング法、プラズマ重合法（高周波
励起イオンプレーティング法）、プラズマCVD法、レー
ザーCVD法、熱CVD法、ガスソースCVD法、コーティング
法、インクジェット法等が適用できる。The method for forming the protective layer is not particularly limited, and includes vacuum vapor deposition, sputtering, reactive sputtering,
MBE (Molecular Beam Epitaxy) method, cluster ion beam method, ion plating method, plasma polymerization method (high-frequency excited ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, An inkjet method or the like can be applied.
【００３６】[0036]
【実施例】以下、実施例により本発明をさらに詳細に説
明するが、本発明はそれらに限定されるものではない。EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited thereto.
【００３７】透明支持基板をエッチング、洗浄した後、
これにポリ[(3,4-エチレンジオキシ)-2,5-チオフェン]
・ポリスチレンスルホン酸分散物「Baytron P」（Bayer
社製、固形分：1.3％）をスピンコートし、150℃で２時
間真空乾燥して膜厚100nmの塗布層（以下「第１層」と
称する）を形成した。なお、透明支持基板としては25mm
×25mm×0.7mmのガラス基板上にITO膜を150nmの厚さで
製膜したもの（東京三容真空（株）製）を用いた。得ら
れた第１層の上に40mgのポリ(N-ビニルカルバゾール)
（PVK）、12mgの2-(4'-t-ブチルフェニル)-5-(4''-(フ
ェニル)フェニル)-1,3,4-オキサジアゾール（PBD）及び
１mgの発光材料クマリン-6を２mlの1,2-ジクロロエタン
に溶解した溶液をスピンコートし、発光層を形成した。
発光層の膜厚は約120nmであった。次に、得られた発光
層の上に発光面積が５mm×５mmとなるようにパターニン
グしたマスクを設置し、蒸着装置内でマグネシウム及び
銀（マグネシウム：銀＝10：１）を250nm共蒸着し、更
に銀を300nm蒸着して、比較用の発光素子101を作製し
た。得られた発光素子101に東陽テクニカ製「ソースメ
ジャーユニット2400型」を用いて直流定電圧を印加して
発光させ、その発光輝度をトプコン社製「輝度計BM-8」
を用いて測定し、発光波長を浜松ホトニクス社製「スペ
クトルアナライザーPMA-11」を用いて測定した。その結
果、発光素子101の印可電圧19Vでの発光輝度は1300cd/m
2、更に電圧を上昇させたときの最高輝度(Lmax)は3000c
d/m2であった。また、発光スペクトルを測定の上、その
全スペクトル領域の発光エネルギーを積分して得られた
値と入力エネルギー値の比から換算した発光の外部量子
効率を評価したところ、入力エネルギーに対する最高発
光外部量子効率（Qexmax）は0.72％であった。After etching and cleaning the transparent supporting substrate,
Poly [(3,4-ethylenedioxy) -2,5-thiophene]
・ Polystyrene sulfonic acid dispersion "Baytron P" (Bayer
Manufactured by K.K., solid content: 1.3%) was spin-coated and vacuum dried at 150 ° C. for 2 hours to form a coating layer having a thickness of 100 nm (hereinafter referred to as “first layer”). As a transparent support substrate, 25 mm
An ITO film having a thickness of 150 nm formed on a glass substrate of 25 mm x 0.7 mm (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) was used. 40 mg of poly (N-vinylcarbazole) on the first layer obtained
(PVK), 12 mg 2- (4'-t-butylphenyl) -5- (4 ''-(phenyl) phenyl) -1,3,4-oxadiazole (PBD) and 1 mg luminescent material coumarin- A solution of 6 in 2 ml of 1,2-dichloroethane was spin-coated to form a light emitting layer.
The thickness of the light emitting layer was about 120 nm. Next, a mask patterned so that the light emitting area is 5 mm × 5 mm is placed on the obtained light emitting layer, and magnesium and silver (magnesium: silver = 10: 1) are co-deposited at 250 nm in the vapor deposition device. Further, silver was vapor-deposited with a thickness of 300 nm to manufacture a comparative light emitting device 101. To the resulting light-emitting element 101, a source constant unit 2400 manufactured by Toyo Technica was used to apply a constant DC voltage to emit light, and the emission brightness was measured by Topcon's "luminance meter BM-8".
The emission wavelength was measured using "Spectrum Analyzer PMA-11" manufactured by Hamamatsu Photonics. As a result, the light emission luminance of the light emitting element 101 at an applied voltage of 19 V is 1300 cd / m.
2 , the maximum brightness (Lmax) when the voltage is further increased is 3000c
It was d / m 2 . In addition, after measuring the emission spectrum, we evaluated the external quantum efficiency of emission calculated from the ratio of the input energy value and the value obtained by integrating the emission energy of the entire spectral region. The efficiency (Qexmax) was 0.72%.
【００３８】第１層の材料及び発光材料を下記表１に示
すものに変えたこと以外は上記発光素子101の作製方法
と同様にして、発光素子102〜112を作製し、発光特性を
評価した。結果を表２に示す。また、発光材料TL-1の構
造を以下に示す。Light-emitting elements 102 to 112 were manufactured in the same manner as in the above-described light-emitting element 101 except that the materials for the first layer and the light-emitting material were changed to those shown in Table 1 below, and the light-emitting characteristics were evaluated. . The results are shown in Table 2. The structure of the light emitting material TL-1 is shown below.
【００３９】[0039]
【表１】 [Table 1]
【００４０】[0040]
【表２】 [Table 2]
【００４１】[0041]
【化12】 [Chemical 12]
【００４２】表２より、比較用の発光素子101及び106と
比較して、上記有機金属化合物を用いた本発明の発光素
子は発光輝度及び発光効率ともに優れていることがわか
る。From Table 2, it can be seen that the light emitting device of the present invention using the above-mentioned organometallic compound is superior in light emission luminance and light emitting efficiency as compared with the light emitting devices 101 and 106 for comparison.
【００４３】[0043]
【発明の効果】以上詳述したように、第4B族ヘテロ原子
を含む有機金属化合物を用いた本発明の発光素子は優れ
た発光効率で高輝度の発光が可能である。As described above in detail, the light emitting device of the present invention using the organometallic compound containing a Group 4B heteroatom can emit light with high luminance and excellent luminous efficiency.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｈ０５Ｂ 33/10 Ｈ０５Ｂ 33/10 33/22 33/22 Ｄ ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI theme code (reference) H05B 33/10 H05B 33/10 33/22 33/22 D
Claims (7)
発光素子において、前記有機層が第4B族ヘテロ原子を含
む有機金属化合物を含有することを特徴とする発光素
子。1. A light emitting device having an organic layer including at least a light emitting layer, wherein the organic layer contains an organometallic compound containing a Group 4B heteroatom.
記有機金属化合物が下記一般式(1)で表されることを特
徴とする発光素子。 【化１】 一般式(1)中、X及びYnはそれぞれSi、Ge及びSnからなる
群から選ばれる原子を表し、Pkは水素原子、アルキル
基、アルケニル基、アルキニル基、アリール基又はヘテ
ロ環基を表し、Q1n、Q2n及びQ3nはそれぞれ水素原子、
アルキル基、アルケニル基、アルキニル基、アリール基
又はヘテロ環基を表し、kは０〜３の整数を表し、nは１
〜４の整数を表す。ただし、Pk、Q1n、Q2n及びQ3nが同
時に水素原子になることはない。2. The light emitting device according to claim 1, wherein the organometallic compound is represented by the following general formula (1). [Chemical 1] In the general formula (1), X and Y n each represent an atom selected from the group consisting of Si, Ge and Sn, and P k represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group. Where Q 1n , Q 2n and Q 3n are each a hydrogen atom,
Represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, k represents an integer of 0 to 3, and n represents 1
Represents an integer of 4; However, P k , Q 1n , Q 2n and Q 3n do not become hydrogen atoms at the same time.
て、前記有機金属化合物が下記一般式(2)で表されるこ
とを特徴とする発光素子。 【化２】 一般式(2)中、ZrはSi、Ge及びSnからなる群から選ばれ
る原子を表し、R1、R2、R 3r及びR4rはそれぞれ水素原
子、アルキル基、アルケニル基、アルキニル基、アリー
ル基又はヘテロ環基を表し、rは３以上の整数を表す。
ただし、R1、R2、R3r及びR4rが同時に水素原子になるこ
とはない。3. The light emitting device according to claim 1 or 2.
The organometallic compound is represented by the following general formula (2):
And a light emitting element. [Chemical 2] Z in general formula (2)rIs selected from the group consisting of Si, Ge and Sn
R atom1, R2, R 3rAnd R4rIs hydrogen source
Child, alkyl group, alkenyl group, alkynyl group, aryl
Group or a heterocyclic group, and r represents an integer of 3 or more.
However, R1, R2, R3rAnd R4rBecome hydrogen atoms at the same time
Not.
子において、前記発光層が三重項励起子から発光する発
光材料を含有することを特徴とする発光素子。4. The light emitting device according to claim 1, wherein the light emitting layer contains a light emitting material that emits light from triplet excitons.
子において、前記有機層が少なくとも１種の高分子化合
物を含有することを特徴とする発光素子。5. The light emitting device according to claim 1, wherein the organic layer contains at least one polymer compound.
子において、前記有機層の少なくとも１層が塗布により
形成された層であることを特徴とする発光素子。6. The light emitting device according to claim 1, wherein at least one of the organic layers is a layer formed by coating.
特徴とする化合物。 【化３】 一般式(1)中、X及びYnはそれぞれSi、Ge及びSnからなる
群から選ばれる原子を表し、Pkは水素原子、アルキル
基、アルケニル基、アルキニル基、アリール基又はヘテ
ロ環基を表し、Q1n、Q2n及びQ3nはそれぞれ水素原子、
アルキル基、アルケニル基、アルキニル基、アリール基
又はヘテロ環基を表し、kは０〜３の整数を表し、nは１
〜４の整数を表す。ただし、Pk、Q1n、Q2n及びQ3nが同
時に水素原子になることはない。 【化４】 一般式(2)中、ZrはSi、Ge及びSnからなる群から選ばれ
る原子を表し、R1、R2、R 3r及びR4rはそれぞれ水素原
子、アルキル基、アルケニル基、アルキニル基、アリー
ル基又はヘテロ環基を表し、rは３以上の整数を表す。
ただし、R1、R2、R3r及びR4rが同時に水素原子になるこ
とはない。7. A compound represented by the following general formula (1) or (2):
Characterized compound. [Chemical 3] In the general formula (1), X and YnConsists of Si, Ge and Sn respectively
Represents an atom selected from the group, PkIs a hydrogen atom, alkyl
Group, alkenyl group, alkynyl group, aryl group or het
Represents a ring group, Q1n, Q2nAnd Q3nAre hydrogen atoms,
Alkyl group, alkenyl group, alkynyl group, aryl group
Or represents a heterocyclic group, k represents an integer of 0 to 3, and n represents 1
Represents an integer of 4; However, Pk, Q1n, Q2nAnd Q3nIs the same
Sometimes it never becomes a hydrogen atom. [Chemical 4] Z in general formula (2)rIs selected from the group consisting of Si, Ge and Sn
R atom1, R2, R 3rAnd R4rIs hydrogen source
Child, alkyl group, alkenyl group, alkynyl group, aryl
Group or a heterocyclic group, and r represents an integer of 3 or more.
However, R1, R2, R3rAnd R4rBecome hydrogen atoms at the same time
Not.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001263162A JP2003077666A (en) | 2001-08-31 | 2001-08-31 | Light emitting element and organic metallic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001263162A JP2003077666A (en) | 2001-08-31 | 2001-08-31 | Light emitting element and organic metallic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003077666A true JP2003077666A (en) | 2003-03-14 |
Family
ID=19089952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001263162A Pending JP2003077666A (en) | 2001-08-31 | 2001-08-31 | Light emitting element and organic metallic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2003077666A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011233912A (en) * | 2004-11-17 | 2011-11-17 | Ube Ind Ltd | Organic electroluminescent element |
-
2001
- 2001-08-31 JP JP2001263162A patent/JP2003077666A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011233912A (en) * | 2004-11-17 | 2011-11-17 | Ube Ind Ltd | Organic electroluminescent element |
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