CN101944572A - Method for manufacturing organic electroluminescence device - Google Patents
Method for manufacturing organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a method for manufacturing an organic electroluminescence device. The organic electroluminescence device comprises a substrate, an anode, a polymer layer, a micromolecule luminous layer, a cavity blocking layer, an electronic transmission layer and a cathode from bottom to top. Before the spin-coating of the micromolecule luminous layer, the spin-coating and refining of the polymer layer by using solvent/non-solvent system solution are performed to remove polymers which are still dissoluble in the polymer layer, so that the left polymer cannot be dissolved in a mixed solvent system, the spin-coating of the micromolecule luminous layer is facilitated, the damage of solvents on the polymer layer during the spin-coating of the micromolecule layer is prevented and a clear interface structure is formed to improve the performance of the device. The method solves the problem of the dissolubility of the solvents on polymer layer materials during the preparation of a double-layer device by a wet process and is also suitable for the wet preparation of other devices. The provided solvent system has university and is suitable for any polymer/micromolecule system with certain dissolubility in organic solvents.
Description
Technical field
The present invention relates to the organic electroluminescence device field, especially relate to double-deck electroluminescent device of polymer/micromolecule of a kind of wet method preparation and preparation method thereof.
Background technology
Along with the development of information communication industry is quickened, require to have the display element of height performance.Wherein, as display element of future generation, organic electroluminescent device (hereinafter to be referred as OLED) has been subjected to paying close attention to widely.
Advantages such as DC driven, curing entirely, wide visual angle, low-power, the response speed of active illuminating, low-voltage are fast because OLED has, low cost, thereby have broad application prospects.Development through nearly more than two decades is obtaining rapid development aspect the improvement of material development and device architecture, organic electroluminescence device has been applied to small display curtain products such as MP3 and mobile phone.In order further to widen the purposes of OLED, currently luminous efficiency, glow color, the exploitation of durability functional material and the exploitation of full-color demonstration have actively been carried out improving.
From the people such as C.W.Tang of Kodak company since the bi-layer devices structure (Appl.Phys.Lett., 51,913, (1987)) of report in 1987, Alq
3Become the star molecule in the luminescent material, and the version of multilayer device receives publicity more and more also.Prepare at present method that multilayer device adopts evaporation more with micromolecule according to the order of device architecture progressively evaporation to substrate, finally obtain a complete device.But because therefore higher should not the production on a large scale of cost of easy crystallization of micromolecule and evaporation process adopt the technology of wet method film forming to be much accounted of gradually.The key technology that wet processing prepares multilayer device is to guarantee that one deck used solvent in preparation back is less to the dissolubility of preceding layer of material, otherwise can't accurately control the thickness of each layer.Because polymer with the difference of micromolecule dissolving, adopts the multilayer device of polymer/small molecule structure to realize easily than preparing multilayer device with micromolecule merely.
Because the cost of wet method fabricate devices is lower, the method that wet method prepares bilayer or multilayer device more and more receives publicity.But wet method prepares multilayer device and has a very big difficult problem: in the time of spin coating second layer material, solvent may influence ground floor, has destroyed the sandwich construction of device thus, influences the performance of device.Increasing research also is devoted to address this problem, and (Adv.Mater.16 (2004) 823 in order to the comparatively superior multilayer device of processability; Appl.Phys.Lett.89 (2006) 3143519; Adv.Mater.17 (2005) 274; Appl.Phys.Lett.90/20 (2007) 203513; Adv.Mater.10 (1998) 769; Synth.Met.91 (1997) 331; Appl.Surf.Sci.253 (2007) 3378; Appl.Phys.Lett.88 (2006) 163501).But in these reports, the process more complicated of the fabricate devices that has, need be by some other extra processing procedure such as photo-crosslinking, template transfer etc.; The preparation process that has is only at some specific material and corresponding solvent, and the process or the system that do not have versatility prepare these multilayer devices.
Summary of the invention
At the problems referred to above, the invention provides a kind of preparation method of organic electroluminescence device, generally to be applicable to polymer/micromolecule device.
To achieve these goals, solution of the present invention is:
A kind of preparation method of organic electroluminescence device, the organic electroluminescence device structure is substrate, anode, polymeric layer, micromolecule luminescent layer, hole blocking layer, electron transfer layer and negative electrode from bottom to top, before spin coating micromolecule luminescent layer, with the solvent/non-solvent system solution polymeric layer is carried out the spin coating purification operations earlier.Still can dissolved polymers in the polymer tunic in order to remove.Sheng Xia polymer will can not be dissolved in the mixed solvent system like this, help spin coating micromolecule luminescent layer.Thereby solvent is to the destruction of polymeric layer when preventing spin coating micromolecule layer, forms clear interfacial structure to improve device performance.
Described solvent/non-solvent system comprises two or more solvent, wherein contain a kind of non-solvent at least, the percent by volume that non-solvent accounts for whole dicyandiamide solution is lower than 30%, described solvent and non-solvent are selected from aromatic solvent, alkyl solvent, alcohol-based solvent, ketone-based solvent, halogen solvent, ether solvent and ester group solvent, described solvent is can the dissolve polymer layer and the organic solvent of micromolecule luminescent layer, non-solvent be can not the dissolve polymer layer organic solvent.
Described substrate is glass, polyesters compound, polysulfones compound or poly-phthalimide compounds.
Described anode is a kind of metal oxide in tin indium oxide, zinc oxide or the tin oxide, or a kind of metal in gold, copper, silver or the zinc.
Described polymeric layer is the polymer with hole injection/transmission performance, and is conjugation, the non-conjugated polymeric thing for preparing in the solution mode.Described polymer is selected from Polyvinyl carbazole (PVK), poly-fluorenes (PF) and derivative thereof, polyphenyl (PPP) and derivative thereof, or polyphenylene ethylene (PPV) and derivative thereof.
The single luminescent layer that described micromolecule luminescent layer is formed for the organic molecule luminescent material, or the mixture of organic molecule luminescent material, or being doped with the small-molecule mixture of fluorescence or phosphorescent coloring, described organic molecule luminescent material is selected from metal organic complex (as Alq
3, Gaq
3The derivative of quinoline aluminum) and some other common luminous organic materials, derivative as benzidine, aryl replaces the derivative of triphenylamine, the derivative of bithiophene, diphenylethyllene aryl analog derivative perylene analog derivative, anthracene derivative, the spiral shell fluorenes, many fluorene kind derivatives, silicone based derivative, machine boron analog derivative, the derivative of adjacent phenanthroline derivative and biphenyl carbazole, described fluorescence or phosphorescent coloring are selected from styryl aryl analog derivative, quinacridone analog derivative perylene class, the fluorenes class, spiral shell fluorenes class, the Coumarins derivative, iridium, the complex of platinum etc., the polyphenylene ethylene vinyl derivative, silicone based, derivatives such as organic boron class.
Described hole blocking layer be adjacent phenanthroline derivative, phenyl by the derivative of heterocyclic substituted such as imidazoles, 1,3, the derivative of 4-oxadiazoles and the derivative of quinoline aluminum, described adjacent phenanthroline derivative is BCP, Bphen; Phenyl is TPBi by the derivative of heterocyclic substituted such as imidazoles; 1,3, the derivative of 4-oxadiazoles is PBD; The derivative of quinoline aluminum is two (2-methyl-8-quinolyl)-4-benzene substituting phenol base-aluminium.
The material of described electron transfer layer is selected from a kind of in benzene-like compounds, oxazole compounds, triazole class compounds, benzene sulphur diazoles compound, pyridine compounds and their, pyrazine compounds, pyrimidines, quinolines or the aromatic condensed ring compounds that metal organic complex, adjacent phenanthroline compounds, furodiazole compound, imidazoles replace, and described metal organic complex is Alq
3, Znq
2Or Bebq
2Adjacent phenanthroline compounds is BCP or BPhen; The furodiazole compound is PBD; The benzene-like compounds that imidazoles replaces is TPBi.
Described negative electrode is metal electrode, alloy electrode or metal fluoride and metal composite electrode, and described metal electrode is selected from lithium, magnesium, aluminium, calcium, strontium, indium; Described alloy electrode be selected from lithium, magnesium, aluminium, calcium, strontium, indium respectively with the alloy of copper, gold, silver; Described metal fluoride and metal composite electrode are LiF/Al.
Concrete preparation process is as follows:
A. be carved with the cleaning of the glass substrate of anode layer in advance: the washing agent of utilization heat is ultrasonic to be cleaned transparent conduction base sheet anode layer glass with the ultrasonic method of deionized water, places it in oven dry under the infrared lamp after the cleaning;
B. the preparation of polymeric layer: the anode layer glass of above-mentioned cleaning, drying is placed on the sol evenning machine, the method spin-coating film of the organic solution of polymer with static batching will be configured, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film, dried again;
C. the preparation of micromolecule luminescent layer: substrate spin coating and that do after the dried is placed on the sol evenning machine, elder generation's spin coating solvent/non-solvent system solution on polymeric layer, can dissolved polymers to remove still, spin coating organic molecule luminescent material mixture solution then, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film is done dried again;
D. the preparation of hole blocking layer: substrate spin coating and that do after the dried is put in the vacuum evaporation chamber evaporation hole blocking layer on luminescent layer;
E. the preparation of electron transfer layer: in vacuum chamber, keep air pressure constant, the evaporation electron transfer layer;
F. the preparation of negative electrode: keep chamber pressure constant, the evaporation negative electrode.
After adopting such scheme, the present invention is from deliquescent angle, consider the dissolubility difference of layers of material in different solvents, be devoted to seek a kind of organic solvent or the dicyandiamide solution little or insoluble, to realize the preparation of double layer material the dissolubility of ground floor material.In preparation process, protect the integrity of ground floor by special method.Wherein, solvent has certain dissolubility to polymer, and stronger to micromolecular solvability, is the primary solvent of spin coating micromolecule luminescent layer; Non-solvent does not have solvability to polymer, and it mainly acts on is the solubility parameters of regulation system, reduces the dissolubility of dicyandiamide solution to polymer.Non-solvent can be a dissolving micromolecule solvent, also can not dissolve micromolecule, if satisfy polymer is not dissolved just passable.This dicyandiamide solution can be the mixed system of two kinds of solvents, also can be three or more mixed system.A little less than containing a kind of volatility in the dicyandiamide solution, when polymer is had certain deliquescent solvent, the pattern of the film that obtains better and the performance of device comparatively superior.
The method that the wet method that relates among the present invention prepares the double-deck electroluminescent device of polymer/micromolecule has solved wet method well and has prepared that solvent is to the solubility problem of polymeric layer material in the bi-layer devices, and it is applicable to the wet method preparation of other device.Dicyandiamide solution provided by the present invention has versatility, is applicable to any certain deliquescent polymer/micromolecule system that has in organic solvent.In addition, the present invention provides a kind of new approaches that reduce the device manufacturing cost for the preparation bi-layer devices.
Description of drawings
Fig. 1 is a white light organic electroluminescent device structural representation of the present invention;
Fig. 2 is that the brightness of the prepared device of NPB of different quality percentage in embodiment 1 luminescent layer is with change in voltage situation curve chart;
Fig. 3 is that the current efficiency of the prepared device of NPB of different quality percentage in embodiment 1 luminescent layer is with change in voltage situation curve chart;
Fig. 4 be among the embodiment 2 in the luminescent layer brightness of the prepared device of NPB of different quality percentage and electric current with change in voltage situation curve chart;
Fig. 5 be among the embodiment 2 in the luminescent layer current efficiency of the prepared device of NPB of different quality percentage with change in voltage situation curve chart.
The figure number explanation
1 transparent conduction base sheet, 2 first electrode layers (anode layer)
3 polymeric layers, 4 organic molecule luminescent layers
5 hole blocking layers, 6 electron transfer layers
7 the second electrode lays (cathode layer), 8 DC power supply
Embodiment
With reference now to Fig. 1,, the preferred structure of electroluminescent device of the present invention is as follows:
Glass (plastics) substrate/ITO/ polymeric layer/micromolecule luminescent layer/hole blocking layer/electron transfer layer/cathode layer.
According to the said structure formula, be described below in conjunction with the detailed execution mode of preparation process of device:
(1) is carved with ITO (Indium Tin Oxides in advance, the cleaning of glass substrate indium tin metal oxide): the washing agent of utilization heat is ultrasonic to be cleaned the transparent conduction base sheet ito glass with the ultrasonic method of deionized water, place it in oven dry under the infrared lamp after the cleaning, wherein the ITO film above the conductive substrate is as the anode layer of device, the square resistance of ITO film is 5 Ω～100 Ω, and thickness is 80～280nm;
(2) preparation of polymeric layer: the ito glass of above-mentioned cleaning, drying is placed on the sol evenning machine, the method spin-coating film of the chlorobenzene solution of PVK with static batching will be configured, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film, do dried under proper condition, thickness is 20～80nm;
(3) preparation of micromolecule luminescent layer: substrate spin coating and that do after the dried is placed on the sol evenning machine, elder generation's dicyandiamide solution of spin coating on polymeric layer, can dissolved polymers to remove still, the micromolecular solution of spin coating then, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film, do dried under proper condition, thickness is 20～80nm, and felicity condition is dry down;
(4) preparation of hole blocking layer: substrate spin coating and that do after the dried is put in the vacuum evaporation chamber evaporation one deck hole blocking layer on luminescent layer;
(5) preparation of electron transfer layer: in vacuum chamber, keep air pressure constant, evaporation one deck electron transfer layer;
(6) preparation of negative electrode: keep chamber pressure constant, the Al of the LiF of evaporation 0.5nm and 100nm is a negative electrode successively.
Embodiment 1:
Refer now to above-mentioned implementation step, the present invention is that mixed solvent system prepares polymer/micromolecule bi-layer devices with chloroform and n-hexane earlier, and wherein the volume ratio of chloroform and n-hexane is 70: 30, and the structure of the electroluminescent device of first embodiment is as follows:
Glass/IT0/PVK (40nm)/NPB:Alq
3(40nm)/BCP (10nm)/Alq
3(30nm)/LiF (0.5nm)/Al (80nm).
(1) is carved with the cleaning of the glass substrate of ITO in advance: utilize the ultrasonic and ultrasonic method of deionized water of the washing agent of heat that the transparent conduction base sheet ito glass is cleaned, place it in oven dry under the infrared lamp after the cleaning, wherein the ITO film above the conductive substrate is as the anode layer of device, the square resistance of ITO film is 5 Ω～100 Ω, and thickness is 80nm～280nm;
(2) preparation of polymeric layer: the ito glass of above-mentioned cleaning, drying is placed on the sol evenning machine, the method spin-coating film of the chlorobenzene solution of PVK with static batching will be configured, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film, do dried under proper condition, thickness is 40nm;
(3) preparation of luminescent layer: substrate spin coating and that do after the dried is placed on the sol evenning machine, and dicyandiamide solution of spin coating on polymeric layer earlier still can dissolved polymers, spin coating NPB and Alq then to remove
3Mixture solution, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film is done dried under proper condition, and thickness is 40nm, and felicity condition is dry down;
(4) preparation of hole blocking layer: substrate spin coating and that do after the dried is put in the vacuum evaporation chamber, and the BCP of evaporation 10nm is a hole blocking layer on luminescent layer;
(5) preparation of electron transfer layer: in vacuum chamber, keep air pressure constant, the Alq of evaporation 30nm
3Be electron transfer layer;
(6) preparation of the preparation of negative electrode: keep chamber pressure constant, the Al of the LiF of evaporation 0.5nm and 100nm is a negative electrode successively.
Fig. 2 is that the brightness of the prepared device of NPB of different quality percentage in embodiment 1 luminescent layer is with change in voltage situation curve chart;
Fig. 3 is that the current efficiency of the prepared device of NPB of different quality percentage in embodiment 1 luminescent layer is with change in voltage situation curve chart;
Embodiment 2:
According to the program fabricate devices identical with example 1, different is that dicyandiamide solution is changed to chloroform, n-hexane and 1, the mixed system of 2-dichloroethanes, and percent by volume is 60: 30: 10.
Fig. 4 is that the brightness of the prepared device of NPB of different quality percentage in embodiment 2 luminescent layers and electric current are with change in voltage situation curve chart (solid dot is represented electric current, and hollow dots is represented brightness);
Fig. 5 is that the efficient of the prepared device of NPB of different quality percentage in embodiment 2 luminescent layers is with change in voltage situation curve chart.
Claims (10)
1. the preparation method of an organic electroluminescence device, the organic electroluminescence device structure is substrate, anode, polymeric layer, micromolecule luminescent layer, hole blocking layer, electron transfer layer and negative electrode from bottom to top, it is characterized in that: before spin coating micromolecule luminescent layer, with the solvent/non-solvent system solution polymeric layer is carried out the spin coating purification operations earlier.
2. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described solvent/non-solvent system comprises two or more solvent, wherein contain a kind of non-solvent at least, the percent by volume that non-solvent accounts for whole dicyandiamide solution is lower than 30%, described solvent and non-solvent are selected from aromatic solvent, the alkyl solvent, alcohol-based solvent, ketone-based solvent, the halogen solvent, ether solvent and ester group solvent, described solvent is can the dissolve polymer layer and the organic solvent of micromolecule luminescent layer, non-solvent be can not the dissolve polymer layer organic solvent.
3. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described substrate is glass, polyesters compound, polysulfones compound or poly-phthalimide compounds.
4. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described anode is a kind of metal oxide in tin indium oxide, zinc oxide or the tin oxide, or a kind of metal in gold, copper, silver or the zinc.
5. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described polymeric layer is the polymer with hole injection/transmission performance, described polymer is selected from Polyvinyl carbazole, poly-fluorenes and derivative thereof, polyphenyl and derivative thereof, or polyphenylene ethylene and derivative thereof.
6. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: the single luminescent layer that described micromolecule luminescent layer is formed for the organic molecule luminescent material, or the mixture of organic molecule luminescent material, or be doped with the small-molecule mixture of fluorescence or phosphorescent coloring, described organic molecule luminescent material is selected from the derivative of quinoline aluminum, the derivative of benzidine, aryl replaces the derivative of triphenylamine, the derivative of bithiophene, diphenylethyllene aryl analog derivative perylene analog derivative, anthracene derivative, the spiral shell fluorenes, many fluorene kind derivatives, silicone based derivative, machine boron analog derivative, the derivative of adjacent phenanthroline derivative and biphenyl carbazole, described fluorescence or phosphorescent coloring are selected from styryl aryl analog derivative, quinacridone analog derivative perylene class, the fluorenes class, spiral shell fluorenes class, the Coumarins derivative, iridium, the complex of platinum etc., the polyphenylene ethylene vinyl derivative, silicone based, or organic boron analog derivative.
7. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described hole blocking layer is that adjacent phenanthroline derivative, phenyl are by the derivative of heterocyclic substituted such as imidazoles, 1,3, the derivative of 4-oxadiazoles and the derivative of quinoline aluminum, described adjacent phenanthroline derivative is BCP, Bphen; Phenyl is TPBi by the derivative of heterocyclic substituted such as imidazoles; 1,3, the derivative of 4-oxadiazoles is PBD; The derivative of quinoline aluminum is two (2-methyl-8-quinolyl)-4-benzene substituting phenol base-aluminium.
8. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: the material of described electron transfer layer is selected from a kind of in benzene-like compounds, oxazole compounds, triazole class compounds, benzene sulphur diazoles compound, pyridine compounds and their, pyrazine compounds, pyrimidines, quinolines or the aromatic condensed ring compounds that metal organic complex, adjacent phenanthroline compounds, furodiazole compound, imidazoles replace, and described metal organic complex is Alq
3, Znq
2Or Bebq
2Adjacent phenanthroline compounds is BCP or BPhen; The furodiazole compound is PBD; The benzene-like compounds that imidazoles replaces is TPBi.
9. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: described negative electrode is metal electrode, alloy electrode or metal fluoride and metal composite electrode, and described metal electrode is selected from lithium, magnesium, aluminium, calcium, strontium, indium; Described alloy electrode be selected from lithium, magnesium, aluminium, calcium, strontium, indium respectively with the alloy of copper, gold, silver; Described metal fluoride and metal composite electrode are LiF/Al.
10. the preparation method of a kind of organic electroluminescence device as claimed in claim 1, it is characterized in that: preparation process is as follows:
A. be carved with the cleaning of the glass substrate of anode layer in advance: the washing agent of utilization heat is ultrasonic to be cleaned transparent conduction base sheet anode layer glass with the ultrasonic method of deionized water, places it in oven dry under the infrared lamp after the cleaning;
B. the preparation of polymeric layer: the anode layer glass of above-mentioned cleaning, drying is placed on the sol evenning machine, the method spin-coating film of the organic solution of polymer with static batching will be configured, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film, dried again;
C. the preparation of micromolecule luminescent layer: substrate spin coating and that do after the dried is placed on the sol evenning machine, elder generation's spin coating solvent/non-solvent system solution on polymeric layer, can dissolved polymers to remove still, spin coating organic molecule luminescent material mixture solution then, the thickness that the rotating speed of concentration, sol evenning machine by control solution and even glue time are controlled spin-coated thin film is done dried again;
D. the preparation of hole blocking layer: substrate spin coating and that do after the dried is put in the vacuum evaporation chamber evaporation hole blocking layer on luminescent layer;
E. the preparation of electron transfer layer: in vacuum chamber, keep air pressure constant, the evaporation electron transfer layer;
F. the preparation of negative electrode: keep chamber pressure constant, the evaporation negative electrode.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110957431A (en) * | 2019-11-29 | 2020-04-03 | 香港大学深圳研究院 | Platinum complex-based organic light-emitting device suitable for wet preparation |
| CN113517417A (en) * | 2021-04-23 | 2021-10-19 | 光华临港工程应用技术研发(上海)有限公司 | Method for manufacturing organic light emitting display device and organic light emitting display device |
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| JP2007214066A (en) * | 2006-02-13 | 2007-08-23 | Seiko Epson Corp | Manufacturing method of organic electroluminescent device |
| US20080074037A1 (en) * | 2006-06-28 | 2008-03-27 | Seiko Epson Corporation | Organic semiconductor device, method for producing organic semiconductor device, organic electroluminescent device, and method for producing organic electroluminescent device |
| CN101339977A (en) * | 2008-08-19 | 2009-01-07 | 西安交通大学 | Hole injection layer of organic small molecular and electroluminescent device thereof |
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| CN1930922A (en) * | 2004-03-11 | 2007-03-14 | 出光兴产株式会社 | Organic electroluminescent device, method of manufacturing the same, and organic solution |
| JP2007214066A (en) * | 2006-02-13 | 2007-08-23 | Seiko Epson Corp | Manufacturing method of organic electroluminescent device |
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| CN101339977A (en) * | 2008-08-19 | 2009-01-07 | 西安交通大学 | Hole injection layer of organic small molecular and electroluminescent device thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110957431A (en) * | 2019-11-29 | 2020-04-03 | 香港大学深圳研究院 | Platinum complex-based organic light-emitting device suitable for wet preparation |
| CN113517417A (en) * | 2021-04-23 | 2021-10-19 | 光华临港工程应用技术研发(上海)有限公司 | Method for manufacturing organic light emitting display device and organic light emitting display device |
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Application publication date: 20110112 |