CN101055920A - Organize EL part and its making method - Google Patents
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- CN101055920A CN101055920A CN 200710065096 CN200710065096A CN101055920A CN 101055920 A CN101055920 A CN 101055920A CN 200710065096 CN200710065096 CN 200710065096 CN 200710065096 A CN200710065096 A CN 200710065096A CN 101055920 A CN101055920 A CN 101055920A
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Abstract
The invention relates to an organic electroluminescence device, comprising an anode layer, an organic functional layer and a cathode layer in order, which is characterized in that a cathode decorative layer made of the alkali metal salt of nitrogenous fragrant phenol is also included between said organic functional layer and the cathode layer, wherein, the alkali metal salt is preferredly a metal cesium salt. The invention has gotten higher device performance when it is used in conjunction with the high work function metallic cathode, through the development of the cathode interface decorative material of membrane that has a high rejection membrane electron injection ability.
Description
Technical field
The present invention relates to the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field, relate in particular to a kind of organic elctroluminescent device that contains the cathodic modification layer and preparation method thereof.
Background technology
Organic electroluminescence device, claim Organic Light Emitting Diode (Organic light-emitting diodes again, OLEDs), be the luminous element that will have organic compound thin film preparation formation between two membrane electrodes (anode and negative electrode) of charge transfer function or electroluminescence function.OLED device cathodes electronics injects and improves most important to device efficiency and stability.In order to overcome the Schottky barrier at cathodic metal and organic semiconductor interface, a kind of effective method is to adopt low workfunction metal, promotes the electronics heat emission to inject.As at traditional N, N '-(Alpha-Naphthyl)-N, N '-phenyl benzidine (NPB)/three (oxine) aluminium (Alq
3) researcher adopts the Mg:Ag alloy in the bi-layer devices, low workfunction metal such as Li:Al alloy improve electronics as negative electrode and inject, but the low workfunction metal activity is strong, destroyed by airborne moisture and oxygen easily, this stability to the processing of cathodic metal in the device preparation process and device itself is all unfavorable.1997, people's such as Hung research group has developed the LiF/Al composite cathode, wherein evaporation LiF layer thickness only is 0.3-0.7nm, and this electronics that does not relate to the composite cathode of active metal injects mechanism and still has arguement at present, but the mechanism of comparatively generally acknowledging is at some organic semiconducting materials such as Alq
3Under existence condition, being reacted by the Al steam of thermal activation and LiF generates low workfunction metal Li, and this metal is generating moment and adjacent organic semiconducting materials (Alq
3) doping of n type takes place, be formed with the chemical species that are beneficial to the electronics injection, improve cathode electronics and inject.Based on the LiF/Al composite cathode, much the inorganic compound of other alkali metal, alkaline-earth metal or lanthanide series metal all adopts the method for vacuum evaporation to be applied to the OLED embellishing cathode interface.
2000, people such as Schmitz were used for the embellishing cathode interface of OLED device with a kind of complex oxine lithium (Liq) that contains alkali metal lithium, were used with metal A l and obtained excellent device performance.The organic coordination compound that oxine sodium and other much contain alkali metal Li or Na also was successfully synthesized afterwards and was used.This class organo-metallic compound is different with Inorganic Dielectric Material (as LiF), and this is as semi-conducting material, has certain electronic transmission performance, has that the evaporation temperature is low, optimal thickness big and advantage such as control easily as the embellishing cathode interface layer.According to the reaction mechanism of embellishing cathode interface, we can obtain such conclusion, and the metal work function of modifying interface material institute metal ion correspondence is low more, will generate corresponding low workfunction metal in the chemical reaction, inject favourable more to electronics.Alkali metal IA family is according to the order of Li, Na, K, Rb, Cs in periodic table, and metal work function reduces successively, and metal Cs work function in all known metal is minimum.Therefore it is more satisfactory developing the organic compound that contains the Cs ion.But Cs is because metallicity is very strong, is difficult to form complex with organic ligand, only can form organic alkoxide, phenates or metal carboxylate.Studies show that the simple organic salt of some of Cs as poor heat stability such as cesium acetate, benzoic acid caesiums, can decompose during vacuum evaporation, has limited its application.
The advantage of polymer organic electroluminescence device is that its preparation process can adopt the method for spin coating or inkjet printing, greatly reduces preparation cost, improves preparation efficiency.Recent research work finds that a lot of micromolecule organic materials also can be made solution, obtain OLED device efficiently with spin-coating method.No matter the spin on polymers device still is a spin coating micromolecule device, and present most negative electrodes still adopt vacuum deposition method.The OLED device that how to prepare no vacuum process becomes research workers' a challenge.The key for preparing antivacuum evaporation negative electrode is that exploitation has the embellishing cathode interface material that can get rid of the high electronics injectability of having of film, and high-work-function metal (as silver) is used as negative electrode and also can obtains higher device performance.
Summary of the invention
Purpose of the present invention provides a kind of not only can be used for vacuum evaporation, but also can be used to get rid of film and have OLED embellishing cathode interface material of excellent electronics injectability and preparation method thereof.
Further aim of the present invention is to provide a kind of organic electroluminescence device that adopts above-mentioned embellishing cathode interface material as the embellishing cathode interface layer.
Further object of the present invention is to provide a kind of preparation method of above-mentioned organic electroluminescence device.
A kind of organic electroluminescence device comprises anode layer, organic function layer and cathode layer successively, it is characterized in that, also comprises the cathodic modification layer that one deck is made up of the alkali metal salt of nitrogenous fragrant phenol between described organic function layer and the cathode layer.
In the used alkali metal salt of above-mentioned organic electroluminescence device, alkali metal can be in lithium, sodium, potassium, rubidium or the caesium any one, the preferable alloy caesium.
In the above-mentioned organic electroluminescence device, the general formula of the cesium salt of nitrogenous fragrant phenol is as follows:
R wherein
1Or R
2Independently be selected from hydrogen atom respectively, or be selected from replacement or unsubstituted alkyl, alkoxyl, nitro, cyano group, alkyl amino, alkylthio group, aromatic radical or heterocyclic aromatic base, preferred R
1Or R
2Be hydrogen atom or methyl, its structural formula following (protection scope of the present invention is not limited to following listed preferred structure):
In the above-mentioned organic electroluminescence device, another general formula of the cesium salt of nitrogenous fragrant phenol is as follows:
R wherein
1Or R
2Independently be selected from hydrogen atom respectively, or be selected from replacement or unsubstituted alkyl, alkoxyl, nitro, cyano group, alkyl amino, alkylthio group, aromatic radical or heterocyclic aromatic base, preferred R
1Or R
2Be hydrogen atom, methyl or methoxy, its structural formula following (protection scope of the present invention is not limited to following listed preferred structure):
In above-mentioned organic electroluminescence device, the cesium salt of nitrogenous fragrant phenol is to be obtained by nitrogenous fragrant phenol and cesium hydroxide prepared in reaction.
In above-mentioned organic electroluminescence device, cathode layer is a metal level, can select any metal of metal activity before aluminium, for example can be any in aluminium, calcium or the magnesium, preferable alloy aluminium.
A kind of preparation method of organic electroluminescence device is characterized in that, evaporation anode layer, organic function layer successively on the substrate, and preparation continues the evaporation cathode layer afterwards as the alkali metal salt of the nitrogenous fragrant phenol of cathodic modification layer on the organic function layer.
In the preparation method of above-mentioned organic electroluminescence device, can be that vacuum vapour deposition, spin coating are got rid of embrane method, dripped in embrane method or the ink-jet printing process any one as the preparation method of the alkali metal salt of the nitrogenous fragrant phenol of cathodic modification layer.
Description of drawings
The section of structure of Fig. 1 organic electroluminescence device of the present invention
Fig. 2 oxine caesium
1The H-NMR spectrogram
The mass spectral analysis spectrogram of Fig. 3 oxine caesium
The thermogravimetric analysis figure of Fig. 4 oxine caesium
Fig. 5 organic electroluminescence device current density of the present invention and voltage relationship figure
Fig. 6 organic electroluminescence device brightness of the present invention and voltage relationship figure
Fig. 7 organic electroluminescence device current efficiency of the present invention and current density graph of a relation.
Fig. 8 organic electroluminescence device of the present invention is at 150mA/cm
2Current efficiency under current density drives and the graph of a relation between the oxine caesium thickness
Embodiment
The present invention is described in further detail below in conjunction with the drawings and specific embodiments.
The cesium salt of nitrogenous fragrant phenol all is to be obtained by nitrogenous fragrant phenol and cesium hydroxide prepared in reaction among the present invention.At first be the preparation of (being called for short Csq) of oxine caesium, reaction equation is shown in equation (1):
Synthetic reaction adopts the device that has water knockout drum and spherical condensation tube, with cyclohexane give is the band aqua, the principle of utilizing cyclohexane and water to form azeotropic mixture will be reacted the water that generates and be removed, promote salt-forming reaction to carry out to positive direction, in preparation process, at first oxine is packed into the mixture that has the cesium hydroxide of a hydrone and have in the flask of water knockout drum and spherical condensation tube, 150 ℃ of oil bath reflux 12 hours, formation glassy yellow precipitation, filtering-depositing, wash several times with cyclohexane, 50 ℃ of vacuumizes are put into glove box after 5 hours and are preserved, and needn't be further purified, and finish preparation thus.
The nuclear-magnetism of the Csq for preparing (
1H-NMR, CDCl
3, 400MHz) spectrogram as shown in Figure 2, left side figure be the numbering of each hydrogen atom among the Csq among Fig. 2, right figure is the spectrum peaks that difference is numbered hydrogen atoms.The mass spectrum of Csq (MS, ESI) figure as shown in Figure 3, as seen from Figure 3, m/z is that 133.0 peak value is Cs
+Characteristic peak, m/z are that 146.1 peak is oxine part O in ionization process
-Generated the characteristic peak of monovalence cation respectively by protonated back with N.Results of elemental analyses represents, the Csq that crosses in air exposure contains two crystallizations water, and (the Csq molecular formula that contains two crystallizations water is: C9H6NOCs.2H2O, Theoretical Calculation obtains containing C element 34.53%, contains H element 3.22%, contains N element 4.47%.Experiment records and contains C element 35.07%, contains H element 3.10%, contains N element 4.49%, and experiment value and calculated value coincide in the experimental error scope).But thermogravimetric analysis shows these two crystallizations water and can remove by substep in heating process, be illustrated in figure 4 as the thermogravimetric analysis figure of Csq, to lose a crystallization water weightlessness at 105.4 ℃ be 91.69% to Csq as seen from the figure, losing two crystallization water weightlessness at 502.9 ℃ is 84.04%, theoretical weightlessness is 94.25% behind one of them crystallization water and the Csq that has two crystallizations water loses, the theoretical weightlessness that two crystallizations water all lose is 88.49%, within error range, coincide with the experimental result of thermogravimetric analysis, illustrate that Csq successively loses two crystallizations water in evaporate process, the film forming that distils then, so this material can be used as the organic light-emitting device electron injecting layer.
Be that the present invention contains the preparation process of Csq as the organic electroluminescence device of cathodic modification layer below, comprise following several steps:
(1) use cleaning agent, deionized water and organic solution to divide several steps to clean the glass substrate that has anode;
(2) by the method evaporation organic function layer of vacuum evaporation, comprise hole transmission layer, luminescent layer;
(3) continue to get rid of the cathodic modification layer that embrane method, an embrane method or ink-jet printing process prepare one deck oxine caesium by vacuum vapour deposition, spin coating;
(4) evaporation metal aluminium lamination afterwards.
Wherein substrate is a transparent substrate, can select glass or flexible substrate, and flexible substrate adopts a kind of material in polyester, the polyimides compounds; Anode layer can adopt inorganic material or organic conductive polymer, inorganic material is generally the higher metals of work function such as metal oxides such as tin indium oxide (ITO), zinc oxide, zinc-tin oxide or gold, copper, silver, preferred ITO, the organic conductive polymer is preferably a kind of material in polythiophene/polyvinylbenzenesulfonic acid sodium, the polyaniline; Hole transmission layer generally adopts the tri-arylamine group material, and the present invention is preferably N, N '-two-(1-naphthyl)-N, N '-diphenyl-1,1-xenyl-4,4-diamines (NPB); Organic luminous layer generally adopts small molecule material, can doping fluorescent material or phosphor material, and the preferred material of main part of the present invention is Alq
3Cathode layer generally adopts the alloy of the lower metal of work functions such as lithium, magnesium, calcium, strontium, aluminium, indium or they and copper, gold, silver, preferable alloy aluminium of the present invention.
Fig. 1 is the section of structure of organic electroluminescence device of the present invention, and wherein substrate 10, anode layer 20, hole transmission layer 30, luminescent layer 40, cathodic modification layer 50 and cathode layer 60.The device architecture of organic electroluminescence device is as follows in the embodiment of the invention:
Glass substrate/ITO/NPB (50nm)/Alq
3(70nm)/Csq/Al (150nm)
Csq adopts vacuum evaporation mode film forming, thickness is respectively 1,2,3,5,8,10,15nm, the current density-voltage relationship of device (J-V) and brightness-voltage relationship (L-V) are respectively as Fig. 5 and shown in Figure 6, as a comparison, adopting 0.5nm LiF is that the OLED device performance of electron injecting layer is also among the insertion figure.By finding out among Fig. 5 and Fig. 6, when Csq thickness during less than 5nm, its performance with adopt LiF suitable as the device performance of decorative layer; When Csq thickness surpasses 5nm, current density and voltage curve all move to the high voltage direction, but the current density of noticing 10nm Csq device is compared the curve of 8nm and 15nm Csq device and is all moved to the low-voltage direction with brightness curve, and driving voltage and Csq thickness relationship are not dull increasing.
Current efficiency-the current density of above-mentioned organic electroluminescence device (E-J) curve as shown in Figure 7, in order to know the variation tendency of display organic electroluminescence light emitting device current efficient more, with above-mentioned each device at 150mA/cm
2Current efficiency under current density drives and the relation table between the Csq thickness are shown among Fig. 8, in order better to compare, also draw device the current efficiency under this current density of LiF as electron injecting layer among Fig. 8.
As can be seen from Figure 7, the thickness of Csq is during less than 5nm, and device efficiency and LiF are suitable as the device efficiency of implanted layer; When Csq thickness was 8～10nm, device efficiency had obvious rising; And Csq thickness is when reaching 15nm, and device efficiency has obviously descended again.Fig. 8 has shown that clearly two peak values have appearred in the current efficiency of device along with Csq thickness increases, and first is at the 2nm place, and second at the 10nm place.The reason that two peak values occur is to change because the electronics of different-thickness Csq injects excitation, when Csq thickness during less than 5nm, the raising that electronics injects can be explained by chemical reaction mechanism, during the evaporation negative electrode, the Al steam that is activated has high reaction activity, can chemical reaction take place with Csq generate metal Cs, metal Cs immediately with quinoline part (among the Csq or Alq
3In the quinoline part because Csq is very thin, think that both of these case has) n takes place mixes and be formed with and be beneficial to the chemical species q that injects electronics
-, promote electronics to inject.When Csq was thin, the Cs that can participate in reaction seldom not enoughly formed effective electronics injecting structure, most of situation be Al directly and Alq
3React, device performance is not high.When Csq is thicker, because its electron transport ability is weaker than Alq
3, electric transmission there is certain inhibition, also can cause device efficiency to descend, so have optimal thickness at the 2nm place.Yet Csq is with to have strong dielectricity LiF different, this is as semiconductor, so this optimal thickness surpasses the optimal thickness 0.2-0.7nm of LiF, and thickness is increased to 5nm left and right sides device performance still obviously not to be reduced, suitable with 0.5nm LiF as the device performance of implanted layer, when Csq thickness surpasses 5nm, formed the continuous whole film.Because Csq is the very strong organic salt of a kind of polarity, permanently-polarised can take place under the electric field induction form dipole, electronics be injected strengthen, improved the coupling in electronics and hole, so the current efficiency of device increases by a fairly big margin, increased by 42% with respect to LiF current efficiency.Too thin being not enough to of Csq thickness forms enough dipoles, and too thick Csq itself has increased the electronics injection barrier, is unfavorable for that also electronics injects, so be that maximum appears in 10nm place current efficiency at Csq thickness.
Among the present invention with the cesium salt of nitrogenous fragrant phenol as the cathodic modification layer material, mainly based on such several reasons, the architecture of at first nitrogenous fragrant phenol cesium salt is proper, if system is too big or too little, all can decompose when vacuum sublimation; Secondly the purpose that contains N in the molecular system is the electron affinity that increases molecule, makes it can form stable anion structure, helps electronics and injects and transmit; Selecting phenols in addition, is because can form the acid organic substance of cesium salt alcohols, phenols and carboxylic acids to be arranged, but the aerial less stable of alcohols cesium salt, and the heating of carboxylic acids cesium salt is very easy to the decarboxylation carbonization, so phenols is proper; The most important is that the cesium salt of nitrogenous fragrant phenol of the present invention can stable in the airly exist in addition, and can vacuum evaporation, this almost has thermal instability with other a lot of organic salts of caesium compares and has significant advantage, and above-mentioned conclusion has also well been verified in a large amount of experiments.
Synthesizing of 2-methyl-oxine caesium (being called for short Csmq), synthetic method just replaces with 2-methyl-8 oxyquinoline with oxine with embodiment 1, and concrete reaction equation is shown in equation (2):
2-methyl-oxine caesium as the research of the preparation method of the organic electroluminescence device of cathodic modification layer and device performance also with embodiment 1.
Synthesizing of 2-phenyl imine methylphenol caesium (being called for short CsPIMP), synthetic method just replaces with 2-phenyl imine methylphenol with 8 oxyquinolines with embodiment 1, and concrete reaction equation is shown in equation (3):
As the research of the preparation method of the organic electroluminescence device of cathodic modification layer and device performance also with embodiment 1.
Synthesizing of 2-p-methylphenyl formimino group phenol caesium (being called for short CsTIMP), synthetic method just replaces with 2-p-methylphenyl formimino group phenol with oxine with embodiment 1, specifically reacts shown in equation (4):
As the research of the preparation method of the organic electroluminescence device of cathodic modification layer and device performance also with embodiment 1.
Synthesizing of 2-p-methoxyphenyl formimino group phenol caesium (being called for short CsMPIMP), synthetic method just replaces with 2-p-methoxyphenyl formimino group phenol with oxine with embodiment 1, specifically reacts shown in equation (5):
As the research of the preparation method of the organic electroluminescence device of cathodic modification layer and device performance also with embodiment 1.
Specific operation process is with above-mentioned embodiment 1-5, the difference part is the cesium salt material C sq of five kinds of nitrogenous fragrant phenol that the foregoing description 1-5 is prepared, Csmq, CsPIMP, CsTIMP, CsMPIMP is dissolved in cellosolvo with the concentration of 1mg/ml and gets rid of film preparation cathodic modification layer, and evaporation metal Al negative electrode is finished the device preparation afterwards.
Specific operation process is with above-mentioned embodiment 1-5, and the difference part is not adopt vacuum evaporation Al negative electrode, and adopts the method for coating Ag slurry to prepare metallic cathode.
Claims (12)
1, a kind of organic electroluminescence device comprises anode layer, organic function layer and cathode layer successively, it is characterized in that, also comprises the cathodic modification layer that one deck is made up of the alkali metal salt of nitrogenous fragrant phenol between described organic function layer and the cathode layer.
2, organic electroluminescence device according to claim 1 is characterized in that, described alkali metal salt is the metal cesium salt.
3, organic electroluminescence device according to claim 2 is characterized in that, the general formula of the cesium salt of described nitrogenous fragrant phenol is as follows:
R wherein
1Or R
2Independently be selected from hydrogen atom respectively, or be selected from replacement or unsubstituted alkyl, alkoxyl, nitro, cyano group, alkyl amino, alkylthio group, aromatic radical or heterocyclic aromatic base.
4, organic electroluminescence device according to claim 3 is characterized in that, described R
1Or R
2Be selected from hydrogen atom or methyl.
5, organic electroluminescence device according to claim 4 is characterized in that, the structural formula of the cesium salt of described nitrogenous fragrant phenol is as follows:
6, organic electroluminescence device according to claim 2 is characterized in that, the general formula of the cesium salt of described nitrogenous fragrant phenol is as follows:
R wherein
1Or R
2Independently be selected from hydrogen atom respectively, or be selected from replacement or unsubstituted alkyl, alkoxyl, nitro, cyano group, alkyl amino, alkylthio group, aromatic radical or heterocyclic aromatic base.
7, organic electroluminescence device according to claim 6 is characterized in that, described R
1Or R
2Be selected from hydrogen atom, methyl or methoxy.
8, organic electroluminescence device according to claim 7 is characterized in that, the structural formula of the cesium salt of described nitrogenous fragrant phenol is as follows:
9, according to the described organic electroluminescence device of the arbitrary claim of claim 1-8, it is characterized in that described cathode layer is a metal level, be selected from aluminium, magnesium or the silver any one.
According to the described organic electroluminescence device of the arbitrary claim of claim 2-8, it is characterized in that 10, the cesium salt of described nitrogenous fragrant phenol is to be obtained by nitrogenous fragrant phenol and cesium hydroxide prepared in reaction.
11, a kind of preparation method of organic electroluminescence device is characterized in that, evaporation anode layer, organic function layer successively on the substrate, and preparation continues the evaporation cathode layer afterwards as the alkali metal salt of the nitrogenous fragrant phenol of cathodic modification layer on the organic function layer.
12, organic light-emitting device preparation method according to claim 11 is characterized in that, the preparation method of the alkali metal salt of described nitrogenous fragrant phenol as the cathodic modification layer is that vacuum vapour deposition, spin coating are got rid of embrane method, dripped embrane method or ink-jet printing process.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101262045B (en) * | 2008-04-24 | 2010-11-10 | 清华大学 | An organic EL part and its making method |
| CN102270741A (en) * | 2010-06-04 | 2011-12-07 | 成功大学 | Organic optoelectronic semiconductor element and method for making same |
| CN101981725B (en) * | 2008-03-31 | 2012-12-12 | 住友化学株式会社 | Organic electroluminescence element, and method for production thereof |
| CN102931352A (en) * | 2012-11-07 | 2013-02-13 | 天津理工大学 | Organic photovoltaic cell with cesium trifluoroacetate as cathode modification layer and preparation |
| CN104201290A (en) * | 2014-08-22 | 2014-12-10 | 上海和辉光电有限公司 | Inverted type organic electroluminescence structure |
-
2007
- 2007-04-03 CN CNB200710065096XA patent/CN100527469C/en active Active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101981725B (en) * | 2008-03-31 | 2012-12-12 | 住友化学株式会社 | Organic electroluminescence element, and method for production thereof |
| CN101262045B (en) * | 2008-04-24 | 2010-11-10 | 清华大学 | An organic EL part and its making method |
| CN102270741A (en) * | 2010-06-04 | 2011-12-07 | 成功大学 | Organic optoelectronic semiconductor element and method for making same |
| CN102270741B (en) * | 2010-06-04 | 2013-07-17 | 成功大学 | Organic optoelectronic semiconductor element and method for making same |
| CN102931352A (en) * | 2012-11-07 | 2013-02-13 | 天津理工大学 | Organic photovoltaic cell with cesium trifluoroacetate as cathode modification layer and preparation |
| CN102931352B (en) * | 2012-11-07 | 2015-01-28 | 天津理工大学 | Organic photovoltaic cell with cesium trifluoroacetate as cathode modification layer and preparation |
| CN104201290A (en) * | 2014-08-22 | 2014-12-10 | 上海和辉光电有限公司 | Inverted type organic electroluminescence structure |
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Address after: Beijing, Haidian District on the East Road, No. 1 hospital building on the first floor of the ring Co-patentee after: Weixinnuo Science and Technology Co., Ltd., Beijing Address before: Rainbow Building, No. 11, information road, Beijing, Haidian District Co-patentee before: Weixinnuo Science and Technology Co., Ltd., Beijing |