WO2012023177A1 - Élément électroluminescent organique - Google Patents
Élément électroluminescent organique Download PDFInfo
- Publication number
- WO2012023177A1 WO2012023177A1 PCT/JP2010/063875 JP2010063875W WO2012023177A1 WO 2012023177 A1 WO2012023177 A1 WO 2012023177A1 JP 2010063875 W JP2010063875 W JP 2010063875W WO 2012023177 A1 WO2012023177 A1 WO 2012023177A1
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- WO
- WIPO (PCT)
- Prior art keywords
- cathode
- organic light
- layer
- emitting device
- electron
- Prior art date
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- TXDKXSVLBIJODL-UHFFFAOYSA-N n-[4-[4-(n-anthracen-9-ylanilino)phenyl]phenyl]-n-phenylanthracen-9-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=C2C=CC=CC2=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=C3C=CC=CC3=2)C=C1 TXDKXSVLBIJODL-UHFFFAOYSA-N 0.000 description 1
- OMQCLPPEEURTMR-UHFFFAOYSA-N n-[4-[4-(n-fluoranthen-8-ylanilino)phenyl]phenyl]-n-phenylfluoranthen-8-amine Chemical group C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=C4C=CC=C2C=34)=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C(C=4C=CC=C5C=CC=C3C=45)=CC=2)C=C1 OMQCLPPEEURTMR-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- LUBWJINDFCNHLI-UHFFFAOYSA-N n-[4-[4-(n-perylen-2-ylanilino)phenyl]phenyl]-n-phenylperylen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=3C=CC=C4C=CC=C(C=34)C=3C=CC=C(C2=3)C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=4C=CC=C5C=CC=C(C=45)C=4C=CC=C(C3=4)C=2)C=C1 LUBWJINDFCNHLI-UHFFFAOYSA-N 0.000 description 1
- TUPXWIUQIGEYST-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-2-ylanilino)phenyl]phenyl]-n-phenylphenanthren-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C(C3=CC=CC=C3C=C2)=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C(C4=CC=CC=C4C=C3)=CC=2)C=C1 TUPXWIUQIGEYST-UHFFFAOYSA-N 0.000 description 1
- QCILFNGBMCSVTF-UHFFFAOYSA-N n-[4-[4-[4-(n-anthracen-1-ylanilino)phenyl]phenyl]phenyl]-n-phenylanthracen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC3=CC=CC=C3C=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC4=CC=CC=C4C=C3C=CC=2)C=C1 QCILFNGBMCSVTF-UHFFFAOYSA-N 0.000 description 1
- RJSTZCQRFUSBJV-UHFFFAOYSA-N n-[4-[4-[n-(1,2-dihydroacenaphthylen-3-yl)anilino]phenyl]phenyl]-n-phenyl-1,2-dihydroacenaphthylen-3-amine Chemical group C1=CC(C2=3)=CC=CC=3CCC2=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=2CCC3=CC=CC(C=23)=CC=1)C1=CC=CC=C1 RJSTZCQRFUSBJV-UHFFFAOYSA-N 0.000 description 1
- UHVLDCDWBKWDDN-UHFFFAOYSA-N n-phenyl-n-[4-[4-(n-pyren-2-ylanilino)phenyl]phenyl]pyren-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC3=CC=CC4=CC=C(C2=C43)C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC4=CC=CC5=CC=C(C3=C54)C=2)C=C1 UHVLDCDWBKWDDN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 239000012466 permeate Substances 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
- 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 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BQFYGYJPBUKISI-UHFFFAOYSA-N potassium;oxido(dioxo)vanadium Chemical compound [K+].[O-][V](=O)=O BQFYGYJPBUKISI-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- NVKTUNLPFJHLCG-UHFFFAOYSA-N strontium chromate Chemical compound [Sr+2].[O-][Cr]([O-])(=O)=O NVKTUNLPFJHLCG-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- HLLICFJUWSZHRJ-UHFFFAOYSA-N tioxidazole Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)SC2=C1 HLLICFJUWSZHRJ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
- H05B33/26—Light sources with substantially two-dimensional radiating surfaces characterised by the composition or arrangement of the conductive material used as an electrode
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/846—Passivation; Containers; Encapsulations comprising getter material or desiccants
Definitions
- film sealing which is a sealing technique for forming a moisture-proof and gas barrier sealing layer
- the sealing principle of film sealing is to obtain sealing capability by covering the organic EL element substrate with a moisture-proof and gas barrier sealing layer, and by using a multilayer structure, further sealing performance is obtained. Can be increased.
- moisture permeation occurs from point defects, and the non-light-emitting region of the element is expanded. Whether or not the circular non-luminous defect is enlarged by subsequent moisture permeability is determined by the presence or absence of a defect in the sealing layer and the size of the defective portion.
- the organic light-emitting device of the present invention is an organic light-emitting device comprising a plurality of organic semiconductor layers including an organic light-emitting layer, which is disposed between an opposing anode and cathode, and the organic semiconductor layer has an electron transport property.
- An n-type dopant-containing electron transport layer in which an electron-donating substance that is in contact with the cathode and can be alloyed with the cathode is mixed in a stoichiometric form, and the cathode and An electron injection assist layer is disposed between and in contact with the n-type dopant-containing electron transport layer.
- an n-type dopant-containing electron transport layer in which an n-type dopant that is an electron donating substance is mixed in the electron transport layer is used to increase the electron transport efficiency and the electron injection efficiency, and the n-type dopant is hygroscopic. It absorbs moisture and oxygen that have entered from the outside. Furthermore, a metal (silver, gold, platinum, or an alloy thereof) that is not easily oxidized is used for the cathode. In general, when a metal species that is difficult to oxidize, that is, a metal species having a high work function (Au, Ag, Pt, etc.) is used, an increase in driving voltage is accompanied by a decrease in electron injection efficiency. It can be avoided by using it.
- the main component of the n-type dopant-containing electron transport layer containing the electron donating substance may contain a substance having a work function or a HOMO level of 3.0 eV or less.
- the organic EL device has an anode 2 / hole injection layer 3 / light emitting layer 5 / n-type dopant-containing electron transport layer 7 / electron injection assist layer 8 / cathode 9.
- anode 2 / hole transport layer 4 / light emitting layer 5 / n-type dopant-containing electron transport layer 7 / electron injection assist layer 8 / cathode 9 / cathode As shown in FIG. 3, anode 2 / hole transport layer 4 / light emitting layer 5 / n-type dopant-containing electron transport layer 7 / electron injection assist layer 8 / cathode 9 / cathode As shown in FIG.
- Organic semiconductor layer-- The organic semiconductor layer (the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, the hole block layer 6 and the n-type dopant-containing electron transport layer 7) has a charge transport property (holes) constituting their main components. And / or an organic compound having electron mobility).
- Examples of the organic compound having an electron transport property as a main component of the light emitting layer and the electron transport layer include polycyclic compounds such as p-terphenyl and quaterphenyl and derivatives thereof, naphthalene, tetracene, pyrene, coronene, chrysene, anthracene, Condensed polycyclic hydrocarbon compounds such as diphenylanthracene, naphthacene, phenanthrene and derivatives thereof, condensed heterocyclic compounds such as phenanthroline, bathophenanthroline, phenanthridine, acridine, quinoline, quinoxaline, phenazine and derivatives thereof, fluorescein, Perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, oxadiazole, al
- Liq, Csq, Naq, Kq Metal acetylacetonato (e.g. Li (acac), K (acac)), Metal dipivaloylmethanato (e.g. Lidpm, Kdpm, Nadpm) Mentioned as a dopant.
- Metal acetylacetonato e.g. Li (acac), K (acac)
- Metal dipivaloylmethanato e.g. Lidpm, Kdpm, Nadpm Mentioned as a dopant.
- Example 3-1 On a transparent glass substrate on an anode made of 110 nm thick ITO, by vacuum deposition, 25 nm thick CuPc as a hole injection layer, 45 nm thick NPB as a hole transport layer, and 30 nm thick Alq3 as a light emitting layer. was deposited. Next, as an n-type dopant-containing electron transport layer, Cs 2 MoO 4 : NBphen with a thickness of 30 nm is co-deposited with 0.066 A / sec of Cs 2 MoO 4 and the co-deposition rate is 2 A / sec in total. A thin film having a Cs 2 MoO 4 concentration of 3.3% by volume was formed.
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
L'invention concerne un élément électroluminescent organique formé d'une pluralité de couches semi-conductrices organiques, qui comprennent une couche électroluminescente organique stratifiée et placée entre une anode et une cathode qui se trouvent sur des côtés opposés. Les couches semi-conductrices organiques sont principalement formées d'un composé organique ayant des propriétés de transport d'électrons. Les couches semi-conductrices organiques comprennent en outre une couche de transport d'électrons contenant un agent dopant de type n dans lequel le matériau donneur d'électrons, qui est en contact avec la cathode et qui peut être allié avec la cathode, est mélangé sous une forme stœchiométrique. Il est prévu une couche d'aide à l'implantation d'électrons, laquelle est placée entre la cathode et la couche de transport d'électrons contenant l'agent dopant de type n et est en contact avec toutes les deux.
Priority Applications (2)
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PCT/JP2010/063875 WO2012023177A1 (fr) | 2010-08-17 | 2010-08-17 | Élément électroluminescent organique |
JP2012529426A JPWO2012023177A1 (ja) | 2010-08-17 | 2010-08-17 | 有機発光素子 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/JP2010/063875 WO2012023177A1 (fr) | 2010-08-17 | 2010-08-17 | Élément électroluminescent organique |
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WO2012023177A1 true WO2012023177A1 (fr) | 2012-02-23 |
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PCT/JP2010/063875 WO2012023177A1 (fr) | 2010-08-17 | 2010-08-17 | Élément électroluminescent organique |
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WO (1) | WO2012023177A1 (fr) |
Cited By (6)
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WO2013171872A1 (fr) * | 2012-05-17 | 2013-11-21 | パイオニア株式会社 | Panneau électroluminescent (el) organique et dispositif électroluminescent |
WO2017033317A1 (fr) * | 2015-08-26 | 2017-03-02 | パイオニア株式会社 | Dispositif électroluminescent |
US9748509B2 (en) | 2013-07-10 | 2017-08-29 | Joled Inc. | Organic EL element and organic EL display panel |
US10734598B2 (en) | 2017-11-30 | 2020-08-04 | Lg Display Co., Ltd. | Organic light-emitting element and organic light-emitting display device using the same |
CN111969017A (zh) * | 2020-08-21 | 2020-11-20 | 合肥维信诺科技有限公司 | 显示面板及其制备方法 |
CN113725376A (zh) * | 2021-08-30 | 2021-11-30 | 合肥京东方卓印科技有限公司 | 有机电致发光器件、制作其的方法及显示面板 |
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WO2013171872A1 (fr) * | 2012-05-17 | 2013-11-21 | パイオニア株式会社 | Panneau électroluminescent (el) organique et dispositif électroluminescent |
US9748509B2 (en) | 2013-07-10 | 2017-08-29 | Joled Inc. | Organic EL element and organic EL display panel |
WO2017033317A1 (fr) * | 2015-08-26 | 2017-03-02 | パイオニア株式会社 | Dispositif électroluminescent |
JPWO2017033317A1 (ja) * | 2015-08-26 | 2018-06-14 | パイオニア株式会社 | 発光装置 |
US10734598B2 (en) | 2017-11-30 | 2020-08-04 | Lg Display Co., Ltd. | Organic light-emitting element and organic light-emitting display device using the same |
CN111969017A (zh) * | 2020-08-21 | 2020-11-20 | 合肥维信诺科技有限公司 | 显示面板及其制备方法 |
CN113725376A (zh) * | 2021-08-30 | 2021-11-30 | 合肥京东方卓印科技有限公司 | 有机电致发光器件、制作其的方法及显示面板 |
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