CN1988203B - Organic luminescence display device and method of manufacturing the same - Google Patents
Organic luminescence display device and method of manufacturing the same Download PDFInfo
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- CN1988203B CN1988203B CN2006101690851A CN200610169085A CN1988203B CN 1988203 B CN1988203 B CN 1988203B CN 2006101690851 A CN2006101690851 A CN 2006101690851A CN 200610169085 A CN200610169085 A CN 200610169085A CN 1988203 B CN1988203 B CN 1988203B
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- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000004020 luminiscence type Methods 0.000 title abstract 2
- 238000002347 injection Methods 0.000 claims abstract description 81
- 239000007924 injection Substances 0.000 claims abstract description 81
- 239000002019 doping agent Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 26
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- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 23
- 238000000151 deposition Methods 0.000 claims description 19
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
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- 150000001412 amines Chemical class 0.000 claims description 9
- 150000001538 azepines Chemical class 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- -1 heterocyclic radical Chemical class 0.000 claims description 7
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- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- 230000000737 periodic effect Effects 0.000 description 3
- 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
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 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
- 239000010405 anode material Substances 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 230000005284 excitation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 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
- 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
- 230000000007 visual effect Effects 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
An organic luminescence display device having an emission layer between a first electrode and a second electrode is disclosed. One embodiment of the device includes: a first hole injection layer and a second hole injection layer between the first electrode and the emission layer; and a charge generation layer doped with a p-type dopant between the first hole injection layer and the second hole injection layer. The device has a reduced driving voltage and an enhanced efficiency and lifetime.
Description
The cross reference of related application
The application requires the rights and interests of korean patent application No.10-2005-0126101 that submits on December 20th, 2005 in Korea S Department of Intellectual Property and the No.10-2005-0129922 that submitted on December 26th, 2005, and the disclosure that this paper introduces them in full as a reference.
Technical field
The disclosure relates to oganic light-emitting display device and manufacture method thereof, more specifically, relates to oganic light-emitting display device and its manufacture method with charge generation layer.
Background technology
Electroluminescence (EL) equipment is the spontaneous emission display device, owing to its advantage such as wide visual angle, high contrast and short response time receive much attention.According to the material of the emission layer that is used to form EL equipment, EL equipment is divided into inorganic EL equipment and organic el device.Organic el device has good brightness and driving voltage and short response time.Organic el device can also color image display.
Usually, oganic light-emitting display device has the anode that is formed on the substrate.Organic el device also comprises hole transport layer (HTL), emission layer (EML), electron transfer layer (ETL) and the negative electrode that stacks gradually on anode.Here, HTL, EML and ETL comprise the organic film that is formed by organic compound.
Above-described organic el device can be by following work.Between anode and negative electrode, apply voltage.Then, by hole transport layer from the anode injected hole to emission layer.Inject electronics to emission layer by electron transfer layer from negative electrode.Electronics and hole be combination more each other in emission layer, forms the exciton with the energy state of exciting thus.Exciton can make the fluorescence molecule emission light of emission layer when excitation state turns back to ground state.
In top-emission type oganic light-emitting display device, the equipment profile is thick more, and microcavity effect is just good more.Microcavity effect is meant the phenomenon that depends on light travel path in equipment from the display device wavelength of light emitted.In addition, has the image deflects minimum that the equipment of thick profile can make particle cause.
But, when the gross thickness of equipment increased, the increase of driving voltage can appear, and this may be a problem.In order to make its maximizing efficiency, a kind of suitable light path need be provided, it allows light to have wavelength near its original wavelength.The thickness of organic layer that can be by changing equipment is adjusted light path.Usually, organic layer is thick more, and optical wavelength is long more.The thick of organic layer is red (R) emission layer, and the thinnest part of organic layer is blue (B) emission layer.Thickness range has preferably periodic thickness, and can obtain maximum light ejection efficiency.One-period thickness is too thin and can not prevent because the emission of the difference that causes of particle.Two periodic thicknesses are too thick and can not prevent the rising of driving voltage, even two periodic thicknesses can prevent because the emission of the difference that particle causes.
Summary of the invention
One aspect of the present invention provides a kind of oganic light-emitting display device, comprising: first electrode; Second electrode; Be inserted in the emission layer between first and second electrodes; Be inserted in first hole injection layer between first electrode and the emission layer; Be inserted in second hole injection layer between first hole injection layer and the emission layer; Be inserted in the charge generation layer between first hole injection layer and second hole injection layer, charge generation layer is doped with p-type dopant.
Charge generation layer can comprise the compound of representing with formula 1:
Formula 1
Wherein R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3); And wherein R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester.
P-type dopant can comprise and is selected from six itrile group six azepines, three penylenes (hexanitrilehexaazatriphenylene), tetrafluoro-four cyano quino bismethane (tetrafluoro-tetraacyanoquinodimethane, F
4-TCNQ), FeCl
3, F
16At least a in CuPc and the metal oxide.Metal oxide can comprise and is selected from vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) and tin indium oxide (ITO) at least a.P-type dopant can have lowest unoccupied molecular orbital (LUMO) energy level.In first and second hole injection layers at least one can comprise the material with highest occupied molecular orbital (HOMO) energy level.Difference in lowest unoccupied molecular orbital (LUMO) energy level of p-type dopant and first and second hole injection layers between highest occupied molecular orbital (HOMO) energy level of the material of at least one can be between pact-2eV peace treaty+2eV.
Equipment can comprise a large amount of pixels, and charge generation layer can form the shared layer of at least two pixels.Charge generation layer can have approximately
-Yue
Thickness.Charge generation layer can have approximately
-Yue
Thickness.
Oganic light-emitting display device also can comprise the hole transport layer that is inserted between first electrode and the emission layer, and is inserted in hole blocking layer, electron transfer layer and the electron injecting layer between the emission layer and second electrode at least one.Oganic light-emitting display device also can comprise the electron transfer layer that is inserted between second electrode and the emission layer.Oganic light-emitting display device also can comprise substrate, and wherein first electrode is formed on the substrate.Oganic light-emitting display device also can comprise the electron injecting layer that is inserted between the electron transfer layer and second electrode.Oganic light-emitting display device also can comprise the hole blocking layer that is inserted between electron transfer layer and the emission layer.
Another aspect of the present invention provides a kind of electronic equipment that comprises above-mentioned oganic light-emitting display device.
Another aspect of the present invention provides a kind of method of making oganic light-emitting display device, and this method comprises: form first hole injection layer on first electrode; Form charge generation layer on first hole injection layer, charge generation layer is doped with p-type dopant; With formation second hole injection layer on charge generation layer.
This method also can comprise: form emission layer on second hole injection layer; With formation second electrode on emission layer.This method also can comprise: form hole transport layer after forming second hole injection layer and before forming emission layer; With after forming emission layer and form at least one that forms before second electrode in hole blocking layer, electron transfer layer and the electron injecting layer.
Charge generation layer can comprise the compound of representing with formula 1:
Formula 1
Wherein R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3); And wherein R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester.
P-type dopant can comprise and is selected from six itrile groups, six azepines, three penylenes, tetrafluoro-four cyano quino bismethane (F
4-TCNQ), FeCl
3, F
16At least a in CuPc and the metal oxide.Metal oxide can be and is selected from vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) and tin indium oxide (ITO) at least a.P-type dopant can have lowest unoccupied molecular orbital (LUMO) energy level.In first and second hole injection layers at least one can comprise the material with highest occupied molecular orbital (HOMO) energy level.Difference in lowest unoccupied molecular orbital (LUMO) energy level of p-type dopant and first and second hole injection layers between highest occupied molecular orbital (HOMO) energy level of the material of at least one can be between pact-2eV peace treaty+2eV.
Forming charge generation layer can comprise making and be heated by resistive vapour deposition, electron-beam vapor deposition, laser beam vapour deposition or sputtering sedimentation.Charge generation layer can have approximately
-Yue
Thickness.
Another aspect of the present invention provides a kind of oganic light-emitting display device and its manufacture method with driving voltage of reduction.
Another aspect of the present invention provides a kind of oganic light-emitting display device that has emission layer between first electrode and second electrode, and this equipment comprises: first hole injection layer between first electrode and emission layer and second hole injection layer; And the charge generation layer that is doped with p-type dopant between first hole injection layer and second hole injection layer.
Of the present invention also providing on the one hand is manufactured on the method that has the oganic light-emitting display device of emission layer between first electrode and second electrode, and this method comprises: form first hole injection layer on first electrode; On first hole injection layer, form the charge generation layer that is doped with p-type dopant; With formation second hole injection layer on charge generation layer.
Description of drawings
Will clearer above-mentioned and others of the present invention by being described in detail with reference to the attached drawings exemplary, wherein:
Fig. 1 is the cross-sectional view of oganic light-emitting display device; With
Fig. 2 A to 2C makes the cross-sectional view of the method for oganic light-emitting display device according to a kind of embodiment for diagram.
Embodiment
Hereinafter, will describe the disclosure in detail by some invention embodiment is described with reference to the accompanying drawings.
Be included in first hole injection layer and second hole injection layer between first electrode and the emission layer according to a kind of organic electroluminescent (EL) display device that between first electrode and second electrode, has emission layer of embodiment.Organic el device can comprise charge generation layer between first hole injection layer and second hole injection layer.Charge generation layer can be doped with p-type dopant.
Charge generation layer according to this embodiment can comprise the compound of representing with formula 1:
Formula 1
In formula 1, R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3) (wherein R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester).The example of the compound of formula 1 includes but not limited to the compound represented with following formula:
In the superincumbent formula, R ' has 1-60 carbon atom and alkyl, aryl or heterocycle for not replacing or being replaced by amine, acid amides, ether or ester.The organic material of the formation charge generation layer of representing with top formula only is used for illustration purpose, rather than is limited to this.
P-type dopant in the charge generation layer can be and is selected from six itrile groups, six azepines, three penylenes, tetrafluoro-four cyano quino bismethane (F
4-TCNQ), FeCl
3, F
16A kind of in CuPc and the metal oxide.Metal oxide can be vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) or tin indium oxide (ITO).
P-type dopant material can be the material that energy level is different from the energy level of the first and/or second hole injection layer material.Difference between highest occupied molecular orbital (HOMO) energy level of lowest unoccupied molecular orbital (LUMO) energy level of p-type dopant material and first hole injection layer and/or the second hole injection layer material can be pact-2eV to pact+2eV.
For example, six azepines, three penylenes have about 9.6eV to the HOMO energy level of about 9.7eV and the lumo energy of about 5.5eV.In addition, tetrafluoro-four cyano quino bismethane (F
4-TCNQ) have the HOMO energy level of about 8.53eV and the lumo energy of about 6.23eV.The first and second hole injection layer materials that use in the oganic light-emitting display device according to the present embodiment have the HOMO energy level of about 4.5eV to about 5.5eV.Therefore, when using six azepines, three penylenes as p-type dopant material, the difference between the HOMO energy level of the lumo energy of charge generation layer and the first hole injection layer material or the second hole injection layer material is that pact-1.0eV is to 0eV.In addition, when using tetrafluoro-four cyano quino bismethane (F
4-during TCNQ) as the p-type dopant material in the charge generation layer, the difference between the HOMO energy level of the lumo energy of charge generation layer and first hole injection layer or second hole injection layer is approximately-0.73 to about 1.73eV.
By using charge generating material between first hole injection layer and second hole injection layer, to form charge generation layer, can reduce the driving voltage of oganic light-emitting display device.
According to a kind of embodiment, can make formation charge generation layers such as being heated by resistive vapour deposition, electron-beam vapor deposition, laser beam vapour deposition, sputtering sedimentation.Charge generation layer can be formed by the compound of representing with formula 1, and the R ' in its Chinese style 1 is C unsubstituted or that replaced by amine, acid amides, ether or ester
5-C
60Alkyl.Can form charge generation layer by ink jet printing, spin coating, blade coating, roller coat etc.In these methods, use solution to replace using CVD (Chemical Vapor Deposition) method to form charge generation layer.
In one embodiment, charge generation layer can form each shared layer of a plurality of pixels.Charge generation layer can have approximately
-Yue
Thickness, randomly about
-Yue
When the thickness of charge generation layer less than
The time, the charge generation effect is lower.When the thickness that produces layer greater than
The time, cause driving voltage to increase or crosstalk owing to leakage current occurring.
Oganic light-emitting display device according to current embodiment also can comprise hole transport layer between first electrode and emission layer.This equipment also can comprise at least one in hole blocking layer, electron transfer layer and the electron injecting layer between the emission layer and second electrode.
According to another embodiment, provide to be manufactured on the method that has the oganic light-emitting display device of emission layer between first electrode and second electrode, this method comprises: form first hole injection layer on first electrode; On first hole injection layer, form the charge generation layer that is doped with p-type dopant; With formation second hole injection layer on charge generation layer.To describe method now in detail according to the manufacturing oganic light-emitting display device of present embodiment.
Fig. 2 A to 2C illustrates the method according to the manufacturing oganic light-emitting display device of an embodiment.At first, deposition anode (first electrode) material forms anode on substrate.Here, can use any substrate of oganic light-emitting display device that is applicable to as substrate.The example of substrate can include but not limited to have good transparency, surface flatness, the easily glass or the transparent plastic substrate of the property handled and water proofing property.Anode material can comprise tin indium oxide (ITO), indium zinc oxide (IZO), the tin oxide (SnO of high work function metal (〉=about 4.5eV) or transparent and highly conductive
2), zinc oxide (ZnO) etc.
First hole is injected (HIL) layer and can be formed on the anode.Can form first hole injection layer by thermal evaporation hole injection layer material in high vacuum.In other embodiments, can use the material of solution form.In these embodiments, can be by spin coating, dip-coating, blade coating, ink jet printing or heat transfer, organic vapor phase deposition cambium layer such as (OVPD).
As mentioned above, can use vacuum heat deposition, spin coating etc. to form first hole injection layer (HIL).The thickness of first hole injection layer can be approximately
-Yue
When the thickness of first hole injection layer less than
The time, the hole injection properties descends.When the thickness of first hole injection layer greater than
The time, driving voltage increases.In a kind of embodiment of top emission structure oganic light-emitting display device, the thickness of first hole injection layer can be at about 1000-approximately
Scope in.
The first hole injection layer examples of material includes but not limited to that copper phthalocyanine (CuPc) or T_Starburst amine series are as TCTA, m-MTDATA, IDE406 (can obtain from Tokyo IdemitsuKosan company) etc.Be the chemical formula of CuPc, TCTA and m-MTDATA below.
Can on first hole injection layer, form charge generation layer.The material of formation charge generation layer can be but is not limited to use the compound of representing as shown in the formula 1:
Formula 1
In formula 1,, R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3).R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester.
Charge generation layer can be doped with p-type dopant.P-type dopant can be and is selected from six itrile groups, six azepines, three penylenes, tetrafluoro-four cyano quino bismethane (F
4-TCNQ), FeCl
3, F
16At least a in CuPc and the metal oxide.Metal oxide can be vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) or tin indium oxide (ITO).
Can be heated by resistive deposited charge on first hole injection layer such as vapour deposition, electron-beam vapor deposition, laser beam vapour deposition, sputter and produce layer material and form charge generation layer by making.Charge generation layer can form the shared layer of a plurality of pixels.Charge generation layer can have approximately-
Approximately
Thickness, randomly about
-Yue
When the thickness of charge generation layer less than
The time, the charge generation effect reduces.When the thickness of charge generation layer greater than
The time, driving voltage increases.
Can form second hole injection layer (HIL) by the deposition second hole injection layer material on charge generation layer.Can make ins all sorts of ways forms the 2nd HIL as vacuum heat deposition, spin coating etc.Material to second hole injection layer does not have particular restriction, but can be identical with the used material of first hole injection layer.The thickness of second hole injection layer can be approximately
-Yue
When the thickness of second hole injection layer less than
The time, the hole-transfer characteristic descends.When the thickness of second hole injection layer greater than
The time, driving voltage increases.
Can randomly form hole transport layer (HTL) by deposition hole-transfer layer material on second hole injection layer.Can make ins all sorts of ways forms HTL as vacuum heat deposition, spin coating etc.The hole transport layer examples of material includes but not limited to N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-[1, the 1-xenyl]-4,4 '-diamines (TPD), N, N '-two (naphthalene-1-yl)-N, N '-diphenylbenzidine (α-NPD), IDE 320 (can obtain) etc. from Idemitsu Kosan company.The thickness of hole transport layer can be approximately
-Yue
When the thickness of hole transport layer less than
The time, the hole-transfer characteristic descends.When the thickness of hole transport layer greater than
The time, driving voltage increases.
Can on hole transport layer, form emission layer (EML).The method that forms emission layer is not had particular restriction, and can make ins all sorts of ways forms emission layer as vacuum moulding machine, ink jet printing, laser induced thermal imaging, photoetching, organic vapor phase deposition (OVPD) etc.The thickness of emission layer can be about 100-approximately
When the thickness of emission layer less than
The time, its efficient and life-span reduce.When the thickness of emission layer greater than
The time, driving voltage increases.Can randomly form HBL by using aforesaid vacuum moulding machine or being spin-coated on the material that deposits formation hole blocking layer (HBL) on the emission layer.The material that forms HBL is not had particular restriction, have electron transport ability and the ionization potential material higher than emitting compound but can be.The examples of material that forms HBL comprises Balq, BCP, TPBI etc.The thickness of hole blocking layer can be approximately
-Yue
When the thickness of hole blocking layer less than
The time, the hole barrier characteristic is poor, causes efficient to reduce.When the thickness of hole blocking layer greater than
The time, driving voltage increases.
Can use vacuum moulding machine or be spin-coated on and form electron transfer layer (ETL) on the hole blocking layer.Material to electron transfer layer does not have particular restriction, and can be Alq3.The thickness of electron transfer layer can be approximately
-Yue
When the thickness of electron transfer layer less than
The time, reduce equipment life.When the thickness of electron transfer layer greater than
The time, driving voltage increases.
In addition, can on electron transfer layer, form electron injecting layer (EIL) optionally.The material that forms electron injecting layer can be LiF, NaCl, CsF, Li
2O, BaO, Liq etc.The thickness of electron injecting layer can be approximately
-Yue
When the thickness of electron injecting layer less than
The time, can not be used as electron injecting layer effectively.When the thickness of electron injecting layer greater than
The time, it is used as insulating barrier, thereby has high driving voltage.
Subsequently, can form negative electrode (or second electrode) by on electron injecting layer, depositing the metal that is used to form negative electrode.Can use vacuum heat deposition, sputter, metal-organic chemical vapor deposition etc. to form negative electrode.The example that is used to form the metal of negative electrode includes but not limited to lithium (Li), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) and magnesium-Yin (Mg-Ag).
As mentioned above, the oganic light-emitting display device according to the present embodiment comprises anode, first hole injection layer, charge generation layer, second hole injection layer, hole transport layer, emission layer, electron transfer layer, electron injecting layer and negative electrode.This equipment also can comprise the intermediate layer between above-mentioned layer two.This equipment also can comprise electronic barrier layer between emission layer and hole transport layer.
Hereinafter, will the disclosure be described in more detail in conjunction with the following examples.These embodiment only are used for the illustrative purpose, and are not intended to limit the scope of the invention.
Embodiment 1
Will be as the 15 Ω/cm of anode
2(
) Corning ito glass substrate (can be from Corning, Inc., Corning, NY obtains) cuts to 50mm * 50mm * 0.7mm, and each personal ultrasonic washing 5 minutes in isopropyl alcohol and pure water respectively, uses UV and ozone clean 30 minutes then.
Vacuum moulding machine m-MTDATA forms on substrate
The first thick hole injection layer.Use the resistance heat vapour deposition on first hole injection layer, deposit extremely as six azepines, three penylenes of the material of formation charge generation layer
Thickness.Vacuum deposited copper m-MTDATA forms on charge generation layer
The second thick hole injection layer.Vacuum moulding machine N on second hole injection layer, N '-two (1-naphthyl)-N, N '-diphenylbenzidine (α-NPD) form
Thick hole transport layer.
Use organic vapor phase deposition (OVPD) to form thickness approximately
Emission layer.Deposition electron transport materials A lq3 forms on emission layer
Thick electron transfer layer.Vacuum moulding machine successively on electron transfer layer
LiF (electron injecting layer) and
Mg-Ag alloy (negative electrode) form the LiF/Al electrode, so just finished oganic light-emitting display device.
Embodiment 2
Make oganic light-emitting display device by the mode identical, except the thickness of charge generation layer is with embodiment 1
Embodiment 3
Make oganic light-emitting display device by the mode identical, except the thickness of charge generation layer is with embodiment 1
The comparative example 1
Will be as the 15 Ω/cm of anode
2(
) Corning ito glass substrate cuts to 50mm * 50mm * 0.7mm, and each personal ultrasonic washing 5 minutes in isopropyl alcohol and pure water respectively, uses UV and ozone clean 30 minutes then.
Vacuum moulding machine m-MTDATA forms on substrate
Thick hole injection layer.Vacuum moulding machine N on hole injection layer, N '-two (1-naphthyl)-N, N '-diphenylbenzidine (α-NPD) form
Thick hole transport layer.
Use organic vapor phase deposition (OVPD) to form thickness approximately
Emission layer.Deposition electron transport materials A lq3 forms on emission layer
Thick electron transfer layer.Vacuum moulding machine successively on electron transfer layer
LiF (electron injecting layer) and
Mg-Ag alloy (negative electrode) form the LiF/Al electrode, so just made oganic light-emitting display device as shown in Figure 1.
Measurement is according to driving voltage, efficient and the life-span of the oganic light-emitting display device of embodiment 1 to 3 and comparative example's 1 manufacturing, and the result is presented in the following table 1.
Table 1
| Driving voltage (V) | Efficient (cd/A) | Life-span (hour) | |
| Embodiment 1 | 5.73 | 27.18 | 1,500 |
| Embodiment 2 | 5.71 | 26.90 | 1,500 |
| Embodiment 3 | 5.60 | 26.85 | 1,500 |
| The comparative example 1 | 7.59 | 26.79 | 1,000 |
In embodiment 1 to 3, driving voltage is 5.73-5.60V, and in comparative example 1, driving voltage is 7.59V.In addition, in embodiment 1 to 3, at 1900cd/m
2Brightness under efficient be 27.18-26.90cd/A, in comparative example 1, at 1900cd/m
2Brightness under efficient be 26.85cd/A.
In addition, the life-span is defined as brightness and is reduced to the 50% needed time of original intensity.In embodiment 1 to 3, at 9500cd/m
2Under life-span be about 1500 hours, in comparative example 1, at 9500cd/m
2Under life-span be about 1000 hours.Therefore, the life-span that can find out embodiment 1-3 is comparative example 1 about 1.5 times of life-span.
Comprise charge generation layer according to oganic light-emitting display device of the present disclosure, thereby reduced the driving voltage of oganic light-emitting display device, and improved its efficient and life-span.
Although the embodiment of reference example specifically describes and has described the disclosure, but those ordinarily skilled in the art can be recognized, only otherwise break away from as the following the spirit and scope of the present invention that claim limited, can make the various variations on form and the details.
Claims (23)
1. oganic light-emitting display device comprises:
First electrode;
Second electrode;
Be inserted in the emission layer between first and second electrodes;
Be inserted in first hole injection layer between first electrode and the emission layer;
The charge generation layer that forms on first hole injection layer, this charge generation layer are doped with p-type dopant; And
Second hole injection layer that on described charge generation layer, forms.
2. the oganic light-emitting display device of claim 1, wherein charge generation layer comprises the compound of representing with formula 1:
Formula 1
Wherein R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3); With
Wherein R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester.
3. the oganic light-emitting display device of claim 1, wherein p-type dopant comprises and is selected from six itrile groups, six azepines, three penylenes, tetrafluoro-four cyano quino bismethane (F
4-TCNQ), FeCl
3, F
16At least a in CuPc and the metal oxide.
4. the oganic light-emitting display device of claim 3, wherein metal oxide comprises and is selected from vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) and tin indium oxide (ITO) at least a.
5. the oganic light-emitting display device of claim 1, wherein p-type dopant has lowest unoccupied molecular orbital (LUMO) energy level, wherein at least one in first and second hole injection layers comprises the material of (HOMO) energy level that has highest occupied molecular orbital, and wherein in the lowest unoccupied molecular orbital of p-type dopant (LUMO) energy level and first and second hole injection layers difference between highest occupied molecular orbital (HOMO) energy level of the material of at least one-2eV and+2eV between.
6. the oganic light-emitting display device of claim 1, wherein this equipment comprises a large amount of pixels, and wherein charge generation layer forms the shared layer of at least two pixels.
7. the oganic light-emitting display device of claim 1, wherein charge generation layer has
Thickness.
8. the oganic light-emitting display device of claim 1, wherein charge generation layer has
Thickness.
9. the oganic light-emitting display device of claim 1 also comprises the hole transport layer that is inserted between first electrode and the emission layer, and is inserted in hole blocking layer, electron transfer layer and the electron injecting layer between the emission layer and second electrode at least one.
10. the oganic light-emitting display device of claim 1 also comprises the electron transfer layer that is inserted between second electrode and the emission layer.
11. the oganic light-emitting display device of claim 10 also comprises substrate, wherein first electrode is formed on the substrate.
12. the oganic light-emitting display device of claim 11 also comprises the electron injecting layer that is inserted between the electron transfer layer and second electrode.
13. the oganic light-emitting display device of claim 12 also comprises the hole blocking layer that is inserted between electron transfer layer and the emission layer.
14. an electronic equipment comprises the oganic light-emitting display device of claim 1.
15. a method of making oganic light-emitting display device, this method comprises:
On first electrode, form first hole injection layer;
Form charge generation layer on first hole injection layer, this charge generation layer is doped with p-type dopant; With
On charge generation layer, form second hole injection layer.
16. the method for claim 15 also comprises:
On second hole injection layer, form emission layer; With
On emission layer, form second electrode.
17. the method for claim 16 also comprises:
After forming second hole injection layer and before forming emission layer, form hole transport layer; With
Form at least one in hole blocking layer, electron transfer layer and the electron injecting layer after forming emission layer and before formation second electrode.
18. the method for claim 15, wherein charge generation layer comprises the compound of representing with formula 1:
Formula 1
Wherein R is itrile group (CN), sulfuryl (SO
2R '), sulfoxide group (SOR '), sulfonamide base (SO
2NR '
2), sulfonic group (SO
3R '), nitro (NO
2) or trifluoromethyl (CF
3); With
Wherein R ' has 1-60 carbon atom and alkyl, aryl or heterocyclic radical for not replacing or being replaced by amine, acid amides, ether or ester.
19. the method for claim 15, wherein p-type dopant comprises and is selected from six itrile groups, six azepines, three penylenes, tetrafluoro-four cyano quino bismethane (F
4-TCNQ), FeCl
3, F
16At least a in CuPc and the metal oxide.
20. the method for claim 19, wherein metal oxide is for being selected from vanadium oxide (V
2O
5), rheium oxide (Re
2O
7) and tin indium oxide (ITO) at least a.
21. the method for claim 15, wherein p-type dopant has lowest unoccupied molecular orbital (LUMO) energy level, wherein at least one in first and second hole injection layers comprises the material of (HOMO) energy level that has highest occupied molecular orbital, and wherein in the lowest unoccupied molecular orbital of p-type dopant (LUMO) energy level and first and second hole injection layers difference between highest occupied molecular orbital (HOMO) energy level of the material of at least one-2 and+2eV between.
22. the method for claim 15 wherein forms charge generation layer and comprises making and be heated by resistive vapour deposition, electron-beam vapor deposition, laser beam vapour deposition or sputtering sedimentation.
23. the method for claim 15, wherein charge generation layer has
Thickness.
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| KR100922758B1 (en) * | 2008-02-20 | 2009-10-21 | 삼성모바일디스플레이주식회사 | An organic light emitting device |
| KR101146193B1 (en) * | 2010-02-23 | 2012-05-24 | 경희대학교 산학협력단 | Organic Semiconductor Device and Its Manufacturing Method |
| KR101135541B1 (en) | 2010-04-01 | 2012-04-13 | 삼성모바일디스플레이주식회사 | Organic light emitting diode device |
| EP2562838A1 (en) * | 2010-04-20 | 2013-02-27 | Sumitomo Chemical Company, Limited | Organic light-emitting element |
| CN103180993B (en) * | 2010-11-09 | 2016-01-27 | 皇家飞利浦电子股份有限公司 | Organic electroluminescence device |
| CN102969459A (en) * | 2012-10-23 | 2013-03-13 | 上海大学 | Organic electroluminescent device and manufacturing method thereof |
| KR102090702B1 (en) * | 2013-01-28 | 2020-05-28 | 삼성디스플레이 주식회사 | Organic light emitting device |
| CN104253226A (en) * | 2013-06-26 | 2014-12-31 | 海洋王照明科技股份有限公司 | An organic light-emitting device and a preparation method thereof |
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