WO2015137812A1 - Method of manufacturing a stacked organic light emitting diode, stacked oled device, and apparatus for manufacturing thereof. - Google Patents
Method of manufacturing a stacked organic light emitting diode, stacked oled device, and apparatus for manufacturing thereof. Download PDFInfo
- Publication number
- WO2015137812A1 WO2015137812A1 PCT/NL2015/050162 NL2015050162W WO2015137812A1 WO 2015137812 A1 WO2015137812 A1 WO 2015137812A1 NL 2015050162 W NL2015050162 W NL 2015050162W WO 2015137812 A1 WO2015137812 A1 WO 2015137812A1
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- WIPO (PCT)
- Prior art keywords
- light emitting
- organic light
- emitting diode
- forming
- layers
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- 238000002347 injection Methods 0.000 claims abstract description 62
- 239000007924 injection Substances 0.000 claims abstract description 62
- 239000000243 solution Substances 0.000 claims abstract description 54
- 238000000231 atomic layer deposition Methods 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 45
- 238000000151 deposition Methods 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims description 25
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002019 doping agent Substances 0.000 claims description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
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- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 8
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 8
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 claims description 5
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- DTTKJBBSHUXGLS-UHFFFAOYSA-N [Li+].[O-2].[Zn+2] Chemical compound [Li+].[O-2].[Zn+2] DTTKJBBSHUXGLS-UHFFFAOYSA-N 0.000 claims description 4
- NVCKFDRIBLWPMQ-UHFFFAOYSA-N [O--].[Mg++].[K+].[Ti+4] Chemical compound [O--].[Mg++].[K+].[Ti+4] NVCKFDRIBLWPMQ-UHFFFAOYSA-N 0.000 claims description 4
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- YVRGRDDGRSFXCH-UHFFFAOYSA-N magnesium;dioxido(oxo)titanium Chemical compound [Mg+2].[O-][Ti]([O-])=O YVRGRDDGRSFXCH-UHFFFAOYSA-N 0.000 claims description 4
- PNHVEGMHOXTHMW-UHFFFAOYSA-N magnesium;zinc;oxygen(2-) Chemical compound [O-2].[O-2].[Mg+2].[Zn+2] PNHVEGMHOXTHMW-UHFFFAOYSA-N 0.000 claims description 4
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 4
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 4
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 4
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- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
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- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
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- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
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- 238000000295 emission spectrum Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
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- 230000003595 spectral effect Effects 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
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- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
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- JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
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- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound 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
- 229960003540 oxyquinoline Drugs 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
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000004076 pyridyl group Chemical group 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
- 239000003870 refractory metal Substances 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—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
- H10K50/13—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 comprising stacked EL layers within one EL unit
- H10K50/131—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 comprising stacked EL layers within one EL unit with spacer layers between the electroluminescent layers
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- H10K50/19—Tandem OLEDs
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/512—Hole transport
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/79—Post-treatment doping
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
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- 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]
- H10K50/17—Carrier injection layers
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- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention is directed at a method of manufacturing a stacked organic light emitting diode - OLED - device.
- the invention further relates to an apparatus for manufacturing a stacked OLED and to a stacked OLED device.
- the OLED lighting standard was at a relatively low brightness level, the industry is presently moving to higher brightness standards. There are various reasons for this, for example, to reduce the required area for a given standard of illumination (office lighting should deliver 500 lm/m2). Another reason is the increased field of application demanding higher brightness levels for certain applications.
- Driving OLEDs to high brightness requires high current power supplies complicating driving electronics and power distribution and markedly degrades lifetime.
- making single layer white devices requires stack design compromises in order to accommodate multiple emissive species which can reduce efficiency and lifetime. Even if successful, this may still not meet the more stringent spectral requirements of some applications, such as obtaining a desired colour gamut of an OLED display screen.
- Stacking OLEDs, often with emission colours, on top of one another is a well-established technique for evaporated OLEDs to address these issues.
- the OLEDs are connected together by charge generation layers which interconvert electrons and holes using either doped or metallic layers. These layers often take the form of a metal oxide hole injection layer in conjunction with an n-doped electron transport layer.
- a common technique to produce stacked OLED devices is by means of thermal evaporation of the consecutive layers.
- a disadvantage of such evaporation methods is that they are to be carried out in a high vacuum.
- thermal evaporation has limited throughput due to low material deposition rates, requires precise temperature control, and contamination may occur from refractory metals that alloy with the evaporation materials.
- a method of manufacturing a stacked organic light emitting diode (OLED) device comprising the steps of: providing a carrier; forming a first organic light emitting diode on the carrier by means of solution printing of consecutive diode layers of said first organic light emitting diode; forming one or more charge injection layers on the first organic light emitting diode; forming a second organic light emitting diode on the carrier by means of solution printing of consecutive diode layers of said second organic light emitting diode;
- step of forming of the one or more charge injection layers comprises a step of performing atomic layer deposition for depositing at least one of the one or more charge injection layers.
- the invention is based on the insight that by using solution printing or solution coating to create the various OLED devices that are to be stacked, the stacked OLED devices may be manufactured under atmospheric pressure conditions. This greatly increases the possibilities of industrializing the method of manufacturing, making it available on a much larger scale for many applications.
- the step of forming the one or more charge injection layers comprises at least one step of atomic layer deposition (ALD).
- ALD atomic layer deposition
- This technique may also be applied at atmospheric pressure conditions, and further allows precise control the layer thickness of the layer deposited.
- the combination of consecutive solution printing steps and an atomic layer deposition step in between enables the protection of the layers underneath the ALD layer from being damaged by a solvent that is used for performing the solution printing step for the second OLED device. This is because ALD allows the use of materials for the charge injection layers that are insoluble to solvents used for solution printing.
- These materials include but are not limited to: zinc oxide (ZnOx), titanium oxide (TiOx), aluminum zinc oxide (AlZn x O y ), lithium zinc oxide (ZnLi x O y ), magnesium zinc oxide (ZnMg y O x ), lithium titanium oxide (TiLixOy), magnesium titanium oxide (TiMgyOx), magnesium potassium titanium oxide (TiMgxKyOz), nickel oxide (NiO x ), tungsten oxide (WO x ) and molybdenum oxide (MoO x ) in all possible atomic ratios.
- the atomic layer deposition step to be performed is a fast atomic layer deposition method.
- Fast atomic layer deposition is a method of performing atomic layer deposition by relatively moving a substrate or carrier subsequently past one or more precursor or reactor gas sources for performing the atomic layer deposition method in a fast and efficient manner.
- the technique of fast atomic layer deposition is for example described in WO 2010/024671.
- fast ALD fast atomic layer deposition technique
- spatial ALD the precursors are dosed simultaneously and continuously, but at different half-reaction zones. The substrate moves between these zones where the half- re actions take place.
- the fast ALD steps described may also be applied as a roll-to-roll process, further increasing the performance and yield of the manufacturing method and highly suitable for industrialization.
- the fast atomic layer deposition method as described above in combination with the solution printing method for providing the first OLED device and the second OLED device, provides a very efficient and fast manner of manufacturing the stacked OLED device in accordance with the invention.
- the ALD deposited charge injection layer enables the formation of a protective layer between the first OLED device and the second OLED device by a suitable choice of materials.
- the solvent from the second OLED device layer in that case may not damage the first OLED device during manufacturing, because the first device layer is covered by the protective ALD deposited charge injection layer during manufacturing.
- each of the first and the second (and any further) organic light emitting diode is a multilayer device.
- the second and further OLED devices are formed on top of the previous OLED devices, separated by means of the charge injection layers being formed comprising at least one atomic layer deposition step.
- any of the other layers may be formed using ALD as well.
- the step of forming the one or more charge injection layers comprises, in accordance with an embodiment, at least one of a step of forming an electron injection layer or a step of forming a hole injection layer. Any one or more of these steps of forming the electron injection layer or the hole injection layer, or both steps, may be performed using an atomic layer deposition step.
- atomic layer deposition allows the application of different materials than by means of solution printing. In case not all of the one or more charge injection layers is created by means of atomic layer deposition, the use of solution printing for providing the other of the one or more charge injection layers would provide a complementary alternative that allows the deposition of suitable materials.
- An electron injection layer as mentioned above may comprise at least one of the group comprising an n-doped material layer comprising a dopant such as an amine, a conjugated organic dopant, a metal salt or a low workfunction metal such as cesium, lithium or magnesium; a metal oxide such as zinc oxide (ZnOx), titanium oxide (TiOx), aluminum zinc oxide (AlZn x O y ), lithium zinc oxide (ZnLi x O y ), magnesium zinc oxide (ZnMgyOx), lithium titanium oxide (TiLi x O y ), magnesium titanium oxide
- a dopant such as an amine, a conjugated organic dopant, a metal salt or a low workfunction metal such as cesium, lithium or magnesium
- a metal oxide such as zinc oxide (ZnOx), titanium oxide (TiOx), aluminum zinc oxide (AlZn x O y ), lithium zinc oxide (ZnLi x O y ), magnesium zinc oxide (ZnMgy
- TiMgyOx magnesium potassium titanium oxide
- TiMg x K y O z magnesium potassium titanium oxide
- a metal or metallic layer such as aluminum (AT), aluminum zinc oxide (AlZnO), or titanium nitride (TiN).
- a hole injection layer as mentioned above may comprise at least one of the group comprising an p-doped material layer comprising a dopant such as 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) or Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7, 10, ll-hexacarbonitrile (HAT-CN or LG- 101); poly-3,4-ethylenedioxythiophene - PEDOT -; a metal oxide such as nickel oxide (NiOx) tungsten oxide (WOx), molybdenum oxide (MoOx); a metal such as silver (Ag) or gold (Au).
- a dopant such as 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) or Dipyrazino[2,3-f:2',3'
- an apparatus for manufacturing a stacked organic light emitting diode (OLED) device comprising a support unit for supporting a carrier for forming thereon the stacked organic light emitting diode; a first solution printing unit for forming a first organic light emitting diode on the carrier by means of solution printing of consecutive diode layers of said first organic light emitting diode; a thin layer deposition unit for forming one or more charge injection layers on the first organic light emitting diode; and at least one of a second solution printing unit, or a transport unit for providing the carrier back to the first solution printing unit, for forming a second organic light emitting diode on the carrier by means of solution printing of consecutive diode layers of said second organic light emitting diode; wherein the thin layer deposition unit comprises an atomic layer deposition unit for depositing at least one of the one or more charge injection layers by means of an atomic layer deposition step.
- a stacked organic light emitting diode device manufactured using the method as described hereinabove.
- Figure 1 schematically illustrates a method in accordance with an embodiment of the present invention
- Figure 2 schematically illustrates a stacked organic light emitting diode device in accordance with an embodiment of the present invention.
- FIG 1 schematically illustrates a method 1 for manufacturing a stacked organic light emitting diode (OLED) device, in accordance with an embodiment of the present invention.
- the method starts at step 5 and includes a step 8 of providing a carrier substrate for the OLED device to be produced.
- the carrier substrate provided in step 8 may be any suitable type of substrate for providing an OLED, for example a glass carrier, metal or a polymer.
- any kind of preprocessing step e.g. manufacturing of the carrier substrate, surface modification of the substrate, or another step, maybe performed. This is not further described herein.
- the method 1 in accordance with the present invention consecutively at least comprises the steps of providing a carrier (step 8), the forming of a first organic light emitting diode on the carrier (step 9), the forming of one or more charged injection layers on the first OLED (steps 12 and 14), and the forming of a second OLED (step 16). At least one of these steps, in particular at least one of the steps 12 and 14 of forming the one or more charge injection layers, is performed using an atomic layer deposition method for depositing at least one of the charge injection layers.
- a first OLED is formed in step 9 by the following consecutive steps.
- an anode is deposited in step 25 in the form of a transparent conductor.
- a hole transmission layer is deposited on top of the anode.
- an emissive layer is deposited in step 28.
- an electron transport layer is deposited in step 30.
- Solution printing may be performed at atmosphere pressure and is therefore particularly useful for industrializing the manufacturing of a stacked OLED device in accordance with the present invention.
- a single printing machine may be used to consecutively print each of the layers in steps 25, 26, 28 and 30.
- any one or more of the steps 25-30 may be performed by an individual printing machine for solution printing of the respective layer.
- step 12 When the first OLED device is formed in step 9, one or more charge injection layers are to be created on top of the first OLED.
- an electron injection layer is deposited on top of the electron transport layer (ETL) deposited in step 30.
- Step 12 is performed, in the embodiment in figure 1, by means of an atomic layer deposition method.
- Atomic layer deposition may be performed at atmospheric pressure, and has been developed into a deposition technique that may be performed in an industrialized process.
- the ALD method may be a roll-to-roll type ALD method.
- step 14 a hole injection layer is deposited on top of the electron injection layer also by means of atomic layer deposition.
- any of the steps 12 or 14 may be performed also by means of solution printing, but in that case the solvent which is used through printing the respective material must be an orthogonal solvent with respect to the layer underneath.
- the use of atomic layer deposition is
- Atomic layer deposition may be performed at low temperatures ( ⁇ 473k ( ⁇ 200°C)). These temperatures are compatible with low cost plastic substrates like PEN (Polyethylene naphthalate ) and PET (Polyethylene terephthalate ), and will not damage previously deposited OLED layers.
- the atomic layer deposition is done at pressures that are somewhat reduced in comparison to atmospheric pressure.
- This reduced pressure is present inside the deposition head, but the deposition head itself can be placed in an atmospheric pressure environment. Therefore, there is no need to establish a vacuum to perform the ALD method.
- the manufacturing method as a whole can thus be carried out at moderate temperatures and under atmospheric pressure. This is an important advantage as it allows one to perform the whole manufacturing process in a cost effective manner, making industrialization possible.
- step 14 the method continues with the solution printing of a second organic light emitting diode (second OLED).
- second OLED organic light emitting diode
- the forming of the second OLED is illustrated in figure 1 with the consecutive steps 32, 35, 37 and 40.
- step 32 a hole transport layer is deposited on top of the hole injection layer that was formed in step 14.
- the hole injection layer may be created using a material which is not dissolvable in the solvent used for solution printing for the HTL of the second OLED. Therefore, step 32 will not damage the hole injection layer underneath.
- step 35 an emissive layer is deposited by means of solution printing.
- an electrode transport layer is formed and the second OLED is finished by the depositing of a cathode in step 40.
- the depositing of the cathode may, for example, include anyone of evaporation, sputtering, or solution printing or coating - although it may be appreciated that synergy is achieved by using a method such as solution printing or coating that can be applied at atmospheric pressure.
- the end of the method 1 in accordance with a first embodiment is indicated with reference numeral 23.
- the steps 25, 26, 28, 30, 32, 35, 37 and 40 are performed using a solution printing method. It may be appreciated that any one or more of these solution printing steps may be replaced by an atomic layer deposition step as well.
- the stacked OLED 50 consists of a substrate 52 on top of which a transparent conductor 55 has been deposited.
- the carrier substrate 52 may be a glass carrier or a polymer, while the transparent electrode 55 forming the anode may be made of a suitable conductive material such as (but not limited to) indium tin oxide (ITO).
- the stacked OLED 50 of the present invention comprises a hole transportation layer (HTL) 56.
- the hole transportation layer may be made of any suitable material, known to the skilled person.
- good candidate materials for the hole transportation layer may be any of the following: arylamines, isoindole, fluorenes, TPD (N,N-diphenyl-N,N-bis(3-methylphenyl)- l, l- biphenyl-4,4-diamine), NPB (l,4-bis(l-naphthylphenylamino)biphenyl), a-NPD (N, N'- di(naphthalen-2-yl)-N, N'-diphenyl-benzidine), m-MTDATA (4,4',4"-tris(3- methylphenylphenylamino) triphenylamine); TCTA (4,4',4"-Tris(carbazol-9-yl)- triphenylamine), 3DTAPBP (2,2'-bis(3-(N,N-di-p-tolylamino
- a hole injection layer (not shown) may be present.
- the hole injection layer may for example comprise poly(3,4-ethylenedioxythiophene)- tetramethacrylate (PEDOT-TMA) or poly(3,4-ethylenedioxythiophene)
- PEDOT-PSS poly(styrenesulfonate)
- an emission layer 57 is provided using again a solution printing process, e.g. step 28.
- metal chelates such as Alq3 (tris(8- hydroxyquinoline) aluminium), Ir(ppy)3 (factris(2-phenylpyridine) iridium) in CPB (4,4-N,N-dicarbazole-biphenyl), Fir Pic (Bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2- carboxypyridyl)iridium(III)) in DCzPPy (2,2'-bis(3-(N,N-di-p- tolylamino)phenyl)biphenyl), or Ir(pic)3 (Tris(l-phenylisoquinoline)iridium(III));
- the stacked OLED 50 of the present invention comprises a electron transport layer (ETL) 58, also created by means of a solution printing step , e.g. step 30.
- the electron transport layer (ETL) 58 may be suitably selected by the skilled person from known alternatives, such as: ETLs (e.g. diazoles, boranes, phenanthrolines, carbazoles, pyridyls), BCP bathocuproine (2, 9 -dimethyl- 4, 7- diphenyl-l.
- an electron injection layer 60 is deposited by means of atomic layer deposition in step 12.
- the electron injection layer may comprise an n-doped material layer comprising a dopant such as an amine, a conjugated organic dopant, a metal salt, or a low work function metal such as cesium, lithium or magnesium, a metal oxide such as zinc oxide (ZnOx), titanium oxide (TiOx), aluminum zinc oxide (AlZn x O y ), lithium zinc oxide (ZnLixOy), magnesium zinc oxide (ZnMgyOx), lithium titanium oxide (TiLixOy), magnesium titanium oxide (TiMgyOx), or magnesium potassium titanium oxide (TiMgxKyOz); a metal or metallic layer such as aluminium (AT), aluminium zinc oxide (AlZnO) or titanium nitride (TiN).
- a dopant such as an amine, a conjugated organic dopant, a metal salt, or a low work function metal such as cesium, lithium
- the hole injection layer 62 may be deposited by means of atomic layer deposition step 14.
- the hole injection layer may comprise at least one of the group comprising an p-doped material layer comprising a dopant such as 2,3,5,6-tetrafluoro- 7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) or dipyrazino[2,3-f:2',3'-h]quinoxaline- 2,3,6, 7, 10, 11-hexacarbonitrile (HAT-CN or LG-101); poly-3,4-ethylenedioxythiophene - PEDOT -; a metal oxide such as nickel oxide (NiO x ) tungsten oxide (WO x ),
- MoO x molybdenum oxide
- Au gold
- a second organic light emitting diode layer may be deposited consisting again of a hole transport layer (HTL) 65, an emissive layer (68) and an electron transport layer 70.
- HTL 65, emissive layer 68 and ETL 70 may be comprised of the same materials that were also used for the first OLED such as to increase the light yield in the same spectral bandwidth.
- different materials may be used such as to target a different emission spectrum.
- a cathode layer 72 is deposited on top of the electron transport layer 70.
- the cathode may be made of any suitable conductive material such as a metal or the like.
- any number of further organic light emitting diodes may be created on top of the second OLED.
- charge injection layers such as electron injection layers 60 and hole injection layer 62 are to be created such as to allow interconversion of electrons and holes in between each two subsequent OLEDs.
- the OLEDs created on top of each other may be of a same or different emission spectrum as mentioned above.
- An apparatus for performing the method of the present invention and for creating an OLED stack in accordance with the present invention may consist of one or more solution printing machines and at least one atomic layer deposition
- each of the solution printed layers may be printed using an individual printing machine.
- the use of a separate printing machine for each of the consecutive layers prevents these layers from being polluted by any materials that may undesirably retain in a printing machine of a previous layer.
- the use of a single printing machine with a purging method for cleaning the printing heads may economically be a more attractive solution.
- the use of individual printing machines for each of the materials to be deposited could be advantageous in view of the above.
- the method can be performed at atmospheric pressure (or at a different pressure if this would be desired), and at regular ambient or moderate temperatures (e.g. 293k, or ⁇ 480k).
- temperatures may also be elevated or lowered by the skilled person.
- Typical temperatures for performing ALD may be 270k to 900k (e.g. ⁇ 0°C to 650°C), for example 293k (20°C), 373k (100°C), 473k (200°C), 493k (220°C), 573k (300°C), 673k (400°C), 773k (500°C).
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EP15715489.9A EP3117022A1 (en) | 2014-03-14 | 2015-03-13 | Method of manufacturing a stacked organic light emitting diode, stacked oled device, and apparatus for manufacturing thereof. |
JP2016575288A JP2017509132A (en) | 2014-03-14 | 2015-03-13 | Method for manufacturing stacked organic light emitting diode, stacked OLED device, and apparatus for manufacturing the same |
CN201580014328.1A CN106104840A (en) | 2014-03-14 | 2015-03-13 | Manufacture method and apparatus and the OLED device of stacking of the Organic Light Emitting Diode of stacking |
US15/124,211 US20170018742A1 (en) | 2014-03-14 | 2015-03-13 | Method of manufacturing a stacked organic light emitting diode, stacked oled device, and apparatus for manufacturing thereof |
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US20170018742A1 (en) * | 2014-03-14 | 2017-01-19 | Nederlandse Organisatie Voor Toegepast- Natuurwetenschappelijk Onderzoek Tno | Method of manufacturing a stacked organic light emitting diode, stacked oled device, and apparatus for manufacturing thereof |
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US11654454B2 (en) | 2015-10-09 | 2023-05-23 | Asm Ip Holding B.V. | Vapor phase deposition of organic films |
JP7299289B2 (en) | 2015-10-09 | 2023-06-27 | エーエスエム アイピー ホールディング ビー.ブイ. | Vapor deposition of organic films |
JP2023120310A (en) * | 2015-10-09 | 2023-08-29 | エーエスエム・アイピー・ホールディング・ベー・フェー | Vapor phase deposition of organic films |
JP7383192B2 (en) | 2015-10-09 | 2023-11-17 | エーエスエム・アイピー・ホールディング・ベー・フェー | Vapor phase deposition of organic films |
US12134108B2 (en) | 2015-10-09 | 2024-11-05 | Asm Ip Holding B.V. | Vapor phase deposition of organic films |
US12138654B2 (en) | 2015-10-09 | 2024-11-12 | Asm Ip Holding B.V. | Vapor phase deposition of organic films |
US11728175B2 (en) | 2016-06-01 | 2023-08-15 | Asm Ip Holding B.V. | Deposition of organic films |
US12205820B2 (en) | 2016-06-01 | 2025-01-21 | Asm Ip Holding B.V. | Deposition of organic films |
US12170197B2 (en) | 2017-02-14 | 2024-12-17 | Asm Ip Holding B.V. | Selective passivation and selective deposition |
Also Published As
Publication number | Publication date |
---|---|
CN106104840A (en) | 2016-11-09 |
EP3117022A1 (en) | 2017-01-18 |
TW201539830A (en) | 2015-10-16 |
US20170018742A1 (en) | 2017-01-19 |
JP2017509132A (en) | 2017-03-30 |
EP2918701A1 (en) | 2015-09-16 |
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