WO2005011333A1 - 白色系有機エレクトロルミネッセンス素子 - Google Patents
白色系有機エレクトロルミネッセンス素子 Download PDFInfo
- Publication number
- WO2005011333A1 WO2005011333A1 PCT/JP2003/009525 JP0309525W WO2005011333A1 WO 2005011333 A1 WO2005011333 A1 WO 2005011333A1 JP 0309525 W JP0309525 W JP 0309525W WO 2005011333 A1 WO2005011333 A1 WO 2005011333A1
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- WIPO (PCT)
- Prior art keywords
- emitting layer
- light emitting
- yellow
- white organic
- group
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title abstract description 3
- 239000000463 material Substances 0.000 claims abstract description 39
- 239000002019 doping agent Substances 0.000 claims abstract description 22
- 239000010410 layer Substances 0.000 claims description 193
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 150000004982 aromatic amines Chemical class 0.000 claims description 13
- 125000005504 styryl group Chemical group 0.000 claims description 13
- 150000002484 inorganic compounds Chemical class 0.000 claims description 11
- 229910010272 inorganic material Inorganic materials 0.000 claims description 11
- -1 styryl compound Chemical class 0.000 claims description 11
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 9
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 claims description 8
- 150000001454 anthracenes Chemical class 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical group C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 claims description 3
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 88
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 239000010408 film Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 18
- 230000032258 transport Effects 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000001769 aryl amino group Chemical group 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007850 fluorescent dye Substances 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000037230 mobility Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass 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
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001275 scanning Auger electron spectroscopy Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
Definitions
- the present invention relates to a white organic electroluminescent device (hereinafter, “electroluminescence” is abbreviated as “EL”).
- EL white organic electroluminescent device
- white organic EL devices have been actively developed because they can be used for monocolor display devices, lighting applications such as backlights, and full color display devices using color filters.
- the change in chromaticity of the white organic EL device not only impairs the quality of the product, but also causes a decrease in color reproducibility, for example, in a full-color display combined with a color filter.
- White organic EL devices are required.
- the conventional white organic EL has a problem that the blue tends to decrease and the chromaticity changes. are doing.
- the excited red-emitting molecules are concentrated at the interface on the hole transport layer side, so that the deterioration causes the balance between electrons and holes to be lost, and if the degree of concentration on the interface changes even slightly,
- the reason for the chromaticity change is that the blue light emission does not change much, but the red light emission changes greatly.
- the light emitting layer is divided into two, there is a laminated type in which the anode side light emitting layer is a yellow to red light emitting layer and the cathode side is a blue light emitting layer.
- the efficiency is excellent, but in order to obtain white light, yellow-red light emission is suppressed, so that the yellow-red light-emitting layer is thinner or doped than the blue light-emitting layer. It was necessary to reduce the concentration, making device fabrication more difficult.
- the thickness of the yellow to red light emitting layer is set to about 1 to 2 nm, white light emission often does not occur. Since this film thickness is as thin as the molecular size of ordinary low molecular organic EL, it can be said that controllability is extremely difficult.
- the present invention has been made in view of the above problems, and has as its object to provide a white organic EL device having little color change. Disclosure of the invention
- the present inventors have proposed that the light emitting layer is divided into two, and the light emitting layer on the anode side, in which the light emitting region of the light emitting layer is likely to be biased, is made to be a light emitting layer.
- the inventors have found that the tendency that the color tends to be biased toward red can be canceled, and completed the present invention.
- the following white organic EL device can be provided.
- a white organic EL device comprising a light emitting layer composed of the blue light emitting layer and the yellow to red light emitting layers.
- Organic EL devices
- styryl derivative is a distyryl derivative, a tristyryl derivative, a tetrastyryl derivative or a styrylamine derivative.
- the white organic EL device according to any one of [1] to [11], wherein the blue dopant is at least one compound selected from styrylamine, an amine-substituted styryl compound, and a compound containing a condensed aromatic ring.
- the yellow to red dopant is a compound having a plurality of fluoranthene skeletons.
- FIG. 1 is a schematic diagram of a white organic EL device according to one embodiment of the present invention.
- BEST MODE FOR CARRYING OUT THE INVENTION is a schematic diagram of a white organic EL device according to one embodiment of the present invention.
- the anode, the blue light emitting layer, the yellow to red light emitting layer, and the cathode are laminated in this order, and the light emitting layer is composed of two layers of a blue light emitting layer and a yellow to red light emitting layer.
- the blue light emitting layer is on the anode side
- the yellow-red light emitting layer is on the cathode side
- the host materials of the blue light emitting layer and the yellow-red light emitting layer are the same substance.
- Another layer can be interposed between the blue light emitting layer and the yellow to red light emitting layer.
- Another organic or inorganic layer can be interposed between the anode and the blue light emitting layer or between the yellow to red light emitting layer and the cathode.
- the intervening layer is not limited as long as it can transport electrons and holes and is transparent.
- Preferable examples include Sanilide In, Sanilide Sn, Sanidri Zn, Sulani Zn, Sulani Cd, and nitrided Ga.
- the white organic EL device of the present invention for example,
- blue light emitting layer is laminated on the anode side of the yellow to red light emitting layer.
- FIG. 1 is a schematic view of one embodiment of the white organic EL device of the present invention.
- the white organic EL device 1 includes an anode 2, a hole injection layer (first organic layer) 3, a hole transport layer 4, a blue light-emitting layer 5, a yellow-red light-emitting layer 6, an electron transport layer (second Organic layer 7) and the cathode 8 are laminated.
- This white organic EL device 1 has a light-emitting layer composed of only a two-layer laminate of a blue light-emitting layer 5 and a yellow to red light-emitting layer 6.
- the anode side is the blue light emitting layer, so that the tendency that the emitted color tends to be shifted to red can be canceled. Therefore, there is no need to suppress yellow-red light emission to obtain white light, and there is no need to reduce the film thickness or doping concentration of the yellow-red light-emitting layer as compared with the blue light-emitting layer. . As a result, the thickness of the yellow to red light emitting layer can be made thicker than before, so that the chromaticity change is small.
- the host material of the blue light emitting layer and the host material of the yellow to red light emitting layer are the same substance, light emission hardly concentrates on the interface of the blue light emitting layer and is hardly affected by the fluctuation of the interface. Further, since the thickness of the yellow-red light emitting layer is sufficiently large, it is hardly affected by the fluctuation of the interface.
- the white organic EL device of the present invention has a small color change, and in particular, hardly undergoes a color change in a high-temperature environment or during continuous driving.
- the blue light emitting layer is composed of a host material and a blue dopant.
- the host material is preferably a styryl derivative, an anthracene derivative or an aromatic amine.
- the styryl derivative is particularly preferably at least one selected from distyryl derivatives, tristyryl derivatives, tetrastyryl derivatives and styrylamine derivatives.
- the anthracene derivative is particularly preferably a compound having a phenylanthracene skeleton.
- the aromatic amine is preferably a compound having 2 to 4 aromatic-substituted nitrogen atoms, and a compound having 2 to 4 aromatic-substituted nitrogen atoms and having at least one alkenyl group. Particularly preferred.
- Examples of the styryl derivative and anthracene derivative include compounds represented by the following general formulas [1] to [5], and examples of the aromatic amine include compounds represented by the following general formulas [6] to [7]. No.
- ⁇ 10 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms; Unsubstituted arylalkyl group having 6 to 30 carbon atoms, substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, unsubstituted monocyclic group having 5 to 30 carbon atoms, substituted Or an unsubstituted fused polycyclic group having 10 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms.
- a r 1 and A r 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted alkenyl group. Or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substitution Or unsubstituted carbon atoms ;!
- substituted or unsubstituted arylthio groups having 6 to 30 carbon atoms substituted or unsubstituted arylalkyl groups having 6 to 30 carbon atoms, unsubstituted carbon atoms
- a monocyclic group having 5 to 30 carbon atoms a substituted or unsubstituted fused polycyclic group having 10 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms.
- shaku 1 to! ⁇ 10 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.
- a r 3 and A r 4 are each independently a Ari group or a substituted or unsubstituted alkenyl group having carbon atoms 6-3 0 substituted or unsubstituted, the substituent, if substituted Ku is not yet Substituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted An alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted An arylalkyl group having 6 to 30 carbon atoms, an unsubstituted monocyclic group having 5 to 30 carbon atoms, a substituted or unsubstituted fused polycyclic group having 10 to 30 carbon atoms, substituted
- ⁇ To 8 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 2 carbon atoms.
- substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms substituted or unsubstituted alkylalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atom number 6 ⁇ 30 arylthio groups, substituted or unsubstituted carbon atoms 7 ⁇ 30 arylalkyl groups, unsubstituted carbon atoms 5 ⁇ 30 monocyclic groups, substituted or unsubstituted carbon atoms A fused polycyclic group of 10 to 30 or a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms.
- a r 3 and A r 4 are each independently a Ari group or a substituted or unsubstituted alkenyl group having carbon atoms 6-3 0 substituted or unsubstituted, the substituent, if substituted Ku is not yet Substituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted An alkylthio group having 1 to 20 carbon atoms; a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; Substituted monocyclic group having 5 to 30 carbon atoms, substituted or unsubstituted fused polycyclic group having 10 to 30 carbon atoms, substituted or unsubstit
- R 21 -R 3Q each independently represent a hydrogen atom, an alkenyl group, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group or and shows a good a heterocyclic group which may, c, d, e ⁇ beauty are each an integer of from 1 to 5; when they are 2 or more, R 21 together, R 2 2 together, R 26 s or R 27 may be the same or different, and R 21 , R 22 , R 26 or R 27 may be bonded to each other to form a ring, or R 23 and R 24 And R 2S and R 29 may combine with each other to form a ring.
- L 2 represents a single bond or one O—, —S—, —N () — (R is an alkyl group or an optionally substituted aryl group) or an arylene group.
- Ar 5 , Ar 6 and Ar 7 each independently represent a substituted or unsubstituted monovalent aromatic group having 6 to 40 carbon atoms, and at least one of them is styrene
- g may represent an integer of 1 to 4.
- Ar 8 , Ar 9 , Ar 11 Ar 13 and Ar 14 each independently represent a substituted or unsubstituted monovalent aromatic group having 6 to 40 carbon atoms
- Ar 1G and Ar 1G 1 2 each independently represent a substituted or unsubstituted divalent aromatic group having carbon atoms 6 to 40
- at least one of a r 8 ⁇ A r 14 is also free Ndei styryl group or styrylene group
- h and k are each an integer from 0 to 2
- i and j are each an integer from 0 to 3.
- the blue dopant is preferably at least one selected from styrylamine, an amine-substituted styryl compound, and a condensed aromatic ring-containing compound. At that time, the blue dopant may be composed of a plurality of different compounds.
- Examples of the styrylamine and the amamine-substituted styryl compound include compounds represented by the following general formulas (8) to (9).
- Examples of the condensed aromatic ring-containing compound include a compound represented by the following general formula (10).
- Ar 5 , Ar 6 and Ar 7 each independently represent a substituted or unsubstituted aromatic group having 6 to 40 carbon atoms, and at least one of them represents a styryl group. And ⁇ represents an integer of 1 to 3.
- a r 1 5 and A r 1 6 are each independently, ⁇ Li one alkylene group having a carbon number of 6 to 3 0, E 1 and E 2, each independently, from 6 carbon atoms 3 0 represents an aryl group, an alkyl group, a hydrogen atom or a cyano group; (1 represents an integer of 1 to 3; U, Z or V is a substituent containing an amino group, and the amino group is an arylamino group; Is preferable.]
- A is an alkyl or alkoxy group having 1 to 16 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms.
- the yellow-red emitting layer is composed of a host material and a yellow-red dopant.
- the host material is the same as the host material used in the blue light emitting layer. It is not preferable to use a different host material because the color change becomes large.
- a fluorescent compound having at least one fluoranthene skeleton or perylene skeleton can be used, and examples thereof include compounds represented by the following general formulas [11] to [27].
- X 1 to X 2 Q each independently represent a hydrogen atom, a straight-chain, branched or cyclic alkyl group having 1 to 20 carbon atoms, a straight-chain A branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms A substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 7 to 3 carbon atoms An arylalkylamino group of 0 or a substituted or unsubstituted alkenyl group having 8 to 30 carbon atoms; adjacent substituents and 1 to: ⁇ 2 . May combine to form a cyclic structure.
- the compounds of the general formulas [11] to [25] preferably contain an amino group or an alkenyl group.
- X 21 to X 24 are each independently an alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Yes, X 21 and X 22 and / or X 23 and X 24 may be bonded via a carbon-carbon bond or 1 O— or 1 S—.
- the fluorescent compound having a fluoranthene skeleton preferably contains an electron donating group in order to obtain high efficiency and long life, and a preferable electron donating group is a substituted or unsubstituted arylamino group. is there.
- the fluorescent compound having a fluoranthene skeleton preferably has 5 or more condensed rings, and particularly preferably 6 or more condensed rings. This is because the fluorescent compound exhibits a fluorescent peak wavelength of 540 to 700 nm and emits white light due to the overlap between the blue light-emitting material and the light emitted from the fluorescent compound.
- the above-mentioned fluorescent compound has a plurality of fluoranthene skeletons, because the emission color is from yellow to red.
- Particularly preferred fluorescent compounds have an electron-donating group and a fluoranthene skeleton or a perylene skeleton, and exhibit a fluorescence peak wavelength of 540 to 700 nm.
- the thickness of the blue light emitting layer is preferably 5 to 30 nm, more preferably 7 to 3 nm, and most preferably 10 to 30 nm. If it is less than 5 nm, it may be difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If it exceeds 30 nm, the driving voltage may increase.
- the thickness of the yellow-red light emitting layer is preferably 10 to 50 nm, more preferably 20 to 50 nm, and most preferably 30 to 50 nm. If it is less than 10 nm, the luminous efficiency may decrease. If it exceeds 50 nm, the driving voltage may increase. 2.
- Other organic layers are preferably 10 to 50 nm, more preferably 20 to 50 nm, and most preferably 30 to 50 nm. If it is less than 10 nm, the luminous efficiency may decrease. If it exceeds 50 nm, the driving voltage may increase. 2.
- Other organic layers are preferably 10 to 50 nm, more preferably 20 to 50 nm, and most preferably 30 to 50 nm. If it is less than 10 nm, the luminous efficiency may decrease. If it exceeds 50 nm, the driving voltage may increase. 2.
- Other organic layers are preferably 10 to 50 nm, more preferably 20 to 50 nm, and most preferably 30 to 50 nm. If it is less than
- a hole injection layer, a hole transport layer, an organic semiconductor layer, or the like can be provided as a first organic layer between the anode and the blue light emitting layer.
- the hole injection layer or the hole transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, has a large hole mobility, and usually has an ionization energy of 5.5 eV or less. small.
- the hole injection layer is provided to adjust the energy level, for example, to alleviate sudden changes in the energy level.
- Material which transports holes to the light emitting layer is preferably at a lower electric field intensity.
- the hole injection layer or a hole transport layer further hole mobilities, for example 1 0 4 ⁇ 1 0 6 VZ cm When the electric field is applied, it is preferably at least 10 to 6 cm 2 / V ⁇ sec.
- the material for forming the hole injecting layer or the hole transporting layer is not particularly limited as long as it has the above preferable properties, and is conventionally used as a hole charge transporting material in photoconductive materials. And any known ones used in the hole injection layer of the organic EL device.
- a material for forming such a hole injection layer or a hole transport layer specifically, for example, a triazole derivative (see U.S. Pat. No. 3,112,197) and an oxadiazole derivative (U.S. Pat. 3,189,447, etc.), imidazole derivatives (see Japanese Patent Publication No. 37-1696, etc.), polyarylalkane derivatives (U.S. Pat. Nos. 3,615,402, 3,820) No.
- Stilbene derivatives Japanese Unexamined Patent Publication No. Sho 61-210363, No. 61-228451, No. 61-14642, No. 61-72255, No. No. 62-47646, No. 62-36 674, No. 62-10652, No. 62-30255, No. 60-93455, No. 60-94462, No. 60-174749, No. 60-175052, etc.
- silazane derivatives U.S. Pat. No.
- the above-mentioned materials can be used.
- the porphyrin compound as disclosed in JP-A-63-2956965
- aromatic tertiary compounds Amine compounds and styrylamine compounds (U.S. Pat. No. 4,127,412, JP-A-53-27033, JP-A-54-58445, JP-A-54-149634, JP-A-54-64299, and No. 55-7 9450, No. 55-144250, No. 56-119132, No. 61-295558, No. 61-98353, No. 63-295695)
- Aromatic Tertiary Gramamine compounds can also be used.
- the hole injecting layer or the hole transporting layer may be composed of one or more of the above-mentioned materials, or may be a compound different from the hole injecting layer or the hole transporting layer. It may be a layer obtained by laminating a hole injection layer or a hole transport layer made of a material.
- the thickness of the hole injection layer or the hole transport layer is not particularly limited. 200200 nm.
- the organic semiconductor layer is a layer for helping the injection of holes or electrons into the emitting layer, it is preferable to have a 1 0- 10 S / cm or more conductivity.
- Examples of the material for such an organic semiconductor layer include thiophene-containing oligomers, conductive oligomers such as arylamine-containing oligomers described in JP-A-8-193191, and conductive dendrimers such as arylamine-containing dendrimers. Etc. can be used.
- the thickness of the organic semiconductor layer is not particularly limited, but is preferably set to 10 to 1,000 nm.
- An electron injection layer or an electron transport layer can be provided as a second organic layer between the cathode and the yellow-red light emitting layer.
- the electron injection layer or the electron transport layer is a layer that assists injection of electrons into the light-emitting layer, and has a high electron mobility.
- the electron injection layer is provided to adjust energy levels, such as to mitigate sudden changes in energy levels.
- a metal complex of 8-hydroxyquinoline or a derivative thereof is preferable.
- the metal complex of 8-hydroxyquinoline or a derivative thereof include a metal chelate toxinide compound containing a chelate of oxine (generally, 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum Can be used.
- the oxadiazole derivative the following general formulas [28] to [30]
- Ar 17, Ar 18, Ar 19, Ar 21, A r 22 and A r 25 are each an or without Ariru group having location substituent, eight 1 "1 7 and eight 1" 1 8 And Ar 19 and Ar 21 and Ar 22 and Ar 25 may be the same or different from each other Ar 20 , Ar 23 and Ar 24 each represent an arylene group having or not having a substituent, A r 23 and A r 24 may be the same or different from each other.)).
- Ar 23 and Ar 24 each represent an arylene group having or not having a substituent, A r 23 and A r 24 may be the same or different from each other.
- Examples of the aryl group in these general formulas [28] to [30] include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group and a pyrenyl group.
- Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a perylenylene group, and a pyrenylene group.
- Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- As the electron transfer compound those having good thin film forming properties are preferably used. The following can be mentioned as specific examples of these electron transfer compounds.
- the thickness of the electron injection layer or the electron transport layer is not particularly limited, but is preferably 1 to 100 nm.
- the blue light emitting layer or the first organic layer which is the organic layer closest to the anode, contains an oxidizing agent.
- Preferred oxidizing agents contained in the light emitting layer or the first organic layer are electron withdrawing or electron acceptors.
- Lewis acids various quinone derivatives, dicyanoquinodimethane derivatives, and salts formed with aromatic amines and Lewis acids.
- Particularly preferred Lewis acids are iron chloride, antimony chloride, aluminum chloride and the like.
- the yellow to red light emitting layer or the second organic layer which is the organic layer closest to the cathode, contains a reducing agent.
- Preferred reducing agents include alkali metals, alkaline earth metals, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth octogenes, rare earths, rhogenides, and alkali metals. And a complex formed with an aromatic compound.
- Particularly preferred alkali metals are Cs, Li, Na, K.
- the inorganic compound layer may have an inorganic compound layer in contact with the anode and / or the cathode.
- the inorganic compound layer functions as an adhesion improving layer.
- Preferred inorganic compounds used in the inorganic compound layer include alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, Si ⁇ x , A 1 O x , S i ⁇ ⁇ , S i ⁇ N, A 1 ON, GeO x , L i ⁇ x , L i ON, T i O x , T i ⁇ N, TaO x , T a ON, TaN x , C, various oxides, nitrides, and oxynitrides.
- Particularly component of layer in contact with the anode, S i O x, A10 x , S iN x, S i ON, A 1 ON, GeO x, C is preferable to form a stable injecting interface layer.
- L i F, MgF 2, C aF 2, M gF 2, N a F are preferred.
- the thickness of the inorganic compound layer is not particularly limited, but is preferably 0. inn! ⁇ 100 nm.
- each of the organic layer and the inorganic compound layer including the light emitting layer is not particularly limited.
- a known method such as an evaporation method, a spin coating method, a casting method, and an LB method can be applied.
- the characteristics of the obtained organic EL element become uniform, and Since the manufacturing time can be shortened, it is preferable that the electron injection layer and the light emitting layer are formed by the same method.For example, when the electron injection layer is formed by the vapor deposition method, the light emitting layer is also formed by the vapor deposition method. Is preferred.
- anode it is preferable to use a metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function (for example, 4.O eV or more).
- a metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function for example, 4.O eV or more.
- ITO indium mucin oxide
- indium zinc oxide, tin, zinc oxide, gold, platinum, palladium and the like can be used alone or in combination of two or more kinds.
- the thickness of the anode is not particularly limited, but is preferably in the range of 10 to 1, OO Onm, and more preferably in the range of 10 to 200 nm.
- the cathode it is preferable to use a metal, an alloy, an electrically conductive compound or a mixture thereof having a low work function (for example, less than 4.O eV).
- a metal, an alloy, an electrically conductive compound or a mixture thereof having a low work function for example, less than 4.O eV.
- one kind of magnesium, aluminum, indium, lithium, sodium, silver and the like can be used alone or in combination of two or more kinds.
- the thickness of the cathode is not particularly limited, but is preferably in the range of 10 to 1000 nm, and more preferably in the range of 10 to 200 nm.
- At least one of the anode and the cathode is substantially transparent, and more specifically, has a light transmittance of 10% or more so that the light emitted from the light emitting layer can be effectively extracted to the outside.
- the power is preferable.
- Electrodes can be manufactured by vacuum evaporation, sputtering, ion plating, electron beam evaporation, CVD, MOCVD, plasma CVD, and the like.
- vacuum evaporation evaporation, sputtering, ion plating, electron beam evaporation, CVD, MOCVD, plasma CVD, and the like.
- the evaluation of the organic EL device obtained in each example is as follows.
- a glass substrate manufactured by Geomatic
- ITO transparent electrode anode
- UV ozone cleaning for 30 minutes.
- the glass substrate with the transparent electrode lines after cleaning is mounted on a substrate holder of a vacuum deposition apparatus.
- a 60 nm-thick N is coated on the surface where the transparent electrode lines are formed so as to cover the transparent electrodes.
- N'-bis ( ⁇ , N'-diphenyl-1-4-aminophenyl) mono-, di-diphenyl-4,4 'diamino-1,1, -biphenyl film did.
- This TPD 232 film functions as a hole injection layer.
- NPD film 4,4,1-bis [N- (1-naphthyl) -1 N-phenylamino] biphenyl film having a thickness of 20 nm was formed on the TPD 232 film. (Abbreviated). This NPD film functions as a hole transport layer.
- a styryl derivative DPVPDAN represented by the formula [31] and B1 represented by the formula [32] are deposited at a weight ratio of 40: 1 at a film thickness of 1 Onm. This was used as a blue light emitting layer.
- a styryl derivative DPVPDAN and R 1 (fluorescence peak wavelength: 545 nm) represented by the formula [33] were deposited at a weight ratio of 40: 1 at 30 nm to form a film, thereby forming a yellow to red light emitting layer.
- A1Q film a tris (8-quinolinol) aluminum film (hereinafter abbreviated as “A1Q film”) having a film thickness of 1 Onm was formed as an electron transport layer.
- Li Li source: manufactured by SAES GE Yuichi Co., Ltd.
- A1q Li film was formed as 1 Onm as an electron injection layer.
- Metal A1 is deposited on this A1q: Li film to a thickness of 150 nm to form a metal cathode.
- This device is the light emission luminance 100 cd / m 2 at a direct current voltage 5 V, white luminous efficiency 7 c DZA maximum onset light intensity 1 10,000 cd / m 2 was obtained.
- Table 1 shows the measurement results of the initial performance, life, and heat resistance of the organic EL devices obtained in Example 1 and Comparative Examples 1 to 3 described below.
- the organic EL element of this example had a long life, high heat resistance, and little color change.
- Example 2 An element was produced in the same manner as in Example 1. However, on the NPD film, the styryl derivative DP VD PAN and the compound (R1) are deposited at a weight ratio of 100: 1 at 10 nm to form a yellow-red emitting layer. DP VD PAN and the compound (B1) were deposited by vapor deposition at a weight ratio of 40: 1 to form a blue light emitting layer. However, the chromaticity was (0.417, 0.436), and yellow light was emitted instead of white. A 105 ° C storage test was performed, and the chromaticity change was extremely large as compared with Example 1.
- Example 2 An element was produced in the same manner as in Example 1. However, on the NPD film, the styryl derivative DP VD PAN and the compound (R1) are vapor-deposited at a weight ratio of 300: 1 at 5 nm to form a yellow-red light-emitting layer. DP VD PAN and the compound (B1) were deposited by vapor deposition at a weight ratio of 40: 1 to form a blue light emitting layer. The chromaticity was (0.321, 0.341), and a good white color was obtained. However, in the 105 ° C storage test, the chromaticity change was larger than that in Example 1. Comparative Example 3
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PCT/JP2003/009525 WO2005011333A1 (ja) | 2003-07-28 | 2003-07-28 | 白色系有機エレクトロルミネッセンス素子 |
US10/566,090 US20080067928A1 (en) | 2003-07-28 | 2003-07-28 | White Organic Electroluminescence Element |
EP03817649A EP1653783A4 (en) | 2003-07-28 | 2003-07-28 | ORGANIC ELECTROLUMINESCENT ELEMENT WITH WHITE LIGHT |
CN03826852.3A CN1820548A (zh) | 2003-07-28 | 2003-07-28 | 白色系有机电致发光元件 |
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US7772762B2 (en) * | 2007-05-18 | 2010-08-10 | Industrial Technology Research Institute | White light organic electroluminescent element |
CN105428545A (zh) * | 2015-12-24 | 2016-03-23 | 天津理工大学 | 一种低压及高色稳定性的白光有机发光二极管 |
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JPWO2005081587A1 (ja) * | 2004-02-19 | 2008-01-17 | 出光興産株式会社 | 白色系有機エレクトロルミネッセンス素子 |
CN102484923B (zh) * | 2009-09-04 | 2016-05-04 | 株式会社半导体能源研究所 | 发光元件、发光装置及其制造方法 |
TWI448534B (zh) * | 2009-09-28 | 2014-08-11 | Ritdisplay Corp | 有機電致發光元件 |
CN101859879A (zh) * | 2010-05-26 | 2010-10-13 | 上海大学 | 一种白色有机电致发光器件及其制备方法 |
KR20180034783A (ko) | 2016-09-27 | 2018-04-05 | 삼성디스플레이 주식회사 | 유기 전계 발광 표시 장치 |
CN109309177A (zh) * | 2018-10-31 | 2019-02-05 | 苏州大学 | 一种高性能有机电致发光器件及其制备方法 |
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CN105428545A (zh) * | 2015-12-24 | 2016-03-23 | 天津理工大学 | 一种低压及高色稳定性的白光有机发光二极管 |
Also Published As
Publication number | Publication date |
---|---|
US20080067928A1 (en) | 2008-03-20 |
CN1820548A (zh) | 2006-08-16 |
EP1653783A1 (en) | 2006-05-03 |
EP1653783A4 (en) | 2009-04-22 |
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