CN100455152C - Organic electro-luminescence device - Google Patents
Organic electro-luminescence device Download PDFInfo
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- CN100455152C CN100455152C CNB2005100870509A CN200510087050A CN100455152C CN 100455152 C CN100455152 C CN 100455152C CN B2005100870509 A CNB2005100870509 A CN B2005100870509A CN 200510087050 A CN200510087050 A CN 200510087050A CN 100455152 C CN100455152 C CN 100455152C
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Abstract
The present invention relates to an organic electroluminescent device which aims to improve the capability of electron injection of the device and to have the advantages of high efficiency, low working voltage and long service life. The organic electroluminescent device of the present invention comprises a basal plate, an anode and a cathode, an organic luminous medium layer between the anode and the cathode, and an electron injection layer positioned between the cathode and the organic luminous medium layer, wherein the electron injection layer comprises an organic salt with a boron atom as a coordination center, and the molecular formula of the organic salt is MBL4, wherein M represents alkali metal or alkali earth metal, B represents the boron atom, L represents a monodentate ligand or a double-dentate ligand. The present invention has the advantages that the efficiency of the electron injection from the cathode to an organic layer in the device is improved, the brightness and the luminous efficiency of the device are enhanced, the service life of the device is prolonged, and the starting voltage and the working voltage of the device are lowered.
Description
Technical field
The present invention relates to a kind of organic electroluminescence device (OLED), comprise a kind of novel electron implanted layer material.
Background technology
A series of advantages such as display of organic electroluminescence has from main light emission, low-voltage DC driven, solidifies entirely, the visual angle is wide, color is abundant, compare with LCD, display of organic electroluminescence does not need backlight, the visual angle is big, power is low, and its response speed can reach 1000 times of LCD, and its manufacturing cost but is lower than the LCD of equal resolution, therefore, display of organic electroluminescence has broad application prospects.
The general structure of organic light-emitting device comprises successively: matrix, anode, organic layer, negative electrode, organic function layer comprises emission layer (EML) again, can also comprise hole injection layer (HIL) and/or hole transmission layer (HTL) between anode and emission layer, and electron transfer layer between emission layer and negative electrode (ETL) and/or electron injecting layer (EIL), can also comprise hole blocking layer (HBL) between emission layer and electron transfer layer etc.
The operation principle of OLED is as follows: when voltage puts between anode and the negative electrode, the hole is injected into the emission layer by hole injection layer and hole transmission layer from anode, electronics is injected into the emission layer by electron injecting layer and electron transfer layer from negative electrode simultaneously, the hole and the electronics that are injected in the emission layer are compound at emission layer, thereby produce exciton (exciton), when excitation state changes ground state into, these excitonic luminescences.For the OLED device, general, the ability of hole transport is better than electron transport ability 10-1000 doubly, and this can cause the decrease in efficiency of device and life-span to reduce.In order to obtain the OLED of high-luminous-efficiency, just must balance hole injection rate and electronics injection rate.
The metal of employing low work function such as calcium, magnesium, magnesium silver alloy etc. can effectively improve the electronics injection rate as negative electrode, but it is subject to the water oxygen corrosion, causes the performance degradation of device.Kodak is at patent US5,776,622, US6,278,236 and document L.S.Hung, C.W.Tang and M.G.Mason, Appl.Phys.Lett.70 discloses a kind of two-layer cathode may technology in 152 (1997), uses the halide of alkali metal or alkaline-earth metal to improve the electronics injectability, obtained efficient and stable extraordinary device, the negative electrode that preferred version lithium fluoride and aluminium constitute is widely used at present.But the existence of halogen atom can cause luminous quencher in the device.
In the prior art, developed the electron injecting layer material between organic layer and metallic cathode, what have selects inorganic material for use, what have selects inorganic organic complex salt for use, as the oxide of alkali metal or alkaline-earth metal, the fluoride of lanthanide series metal and oxide, alkali-metal acetate (C.Ganzorig, K.Suga and M.Fujihira, Mater.Sci.Eng.B.85,140 (2001)), alkali-metal acetate acetonide (US6,558,817) or the like.
Summary of the invention
The objective of the invention is to propose a kind of electroluminescent device that uses the novel electron injection material, by the injection rate of hole in the balancing device and electronics, it is low to guarantee that device obtains operating voltage, efficient height, long superperformance of life-span.
A kind of organic luminescent device, comprise substrate, anode and negative electrode, and between this to the organic light emitting medium layer between the electrode, also comprise the electron injecting layer between negative electrode and organic light emitting medium layer, it is characterized in that, this electron injecting layer comprises with the boron atom being the organic salt of coordination center, and its molecular formula is: MBL
4, wherein, M represents alkali metal or alkaline-earth metal, and B represents the boron atom, and L is monodentate ligand or bidentate ligand.
Wherein alkali-metal is the organic salt of coordination center with the boron atom, and what preferably comprise lithium is the organic salt of coordination center with the boron atom, caesium be the organic salt of coordination center with the boron atom.
Alkaline-earth metal be the organic salt of coordination center with the boron atom, what preferably comprise magnesium is the organic salt of coordination center with the boron atom, calcium be the organic salt of coordination center with the boron atom, barium be the organic salt of coordination center with the boron atom.
Is the organic salt MBL of coordination center as the electron injecting layer material with the boron atom
4In ligand L preferably from replacing or unsubstituted following groups: oxine, 2-methyl-oxine, 8-hydroxy benzo pyrazine, 4-hydroxyl-1, (2-hydroxy phenyl) benzoxazole, 2-(2-hydroxy phenyl) benzimidazole, 2-(2-hydroxy phenyl) benzothiazole, 10-hydroxy benzo quinoline or pyridine-2-formic acid, substituting group is selected from alkyl, aromatic group for 5-naphthyridines, 5-hydroxyl-quinoxaline, 2-.
The electron injecting layer material is most preferred to be four (oxine) lithium borate, four (2-methyl-oxine) lithium borate, four (8-hydroxy benzo pyrazine) lithium borate, four (oxine) boric acid caesium, four (2-methyl-oxine) boric acid caesium, four (8-hydroxy benzo pyrazine) boric acid caesium.
The electron injecting layer thickness range is 0.1nm to 2nm, and most preferred range is 0.1nm to 1nm.
Cathode material is selected Al for use, Ca, Ba, a kind of in Mg or the Mg:Ag alloy.
Beneficial effect of the present invention: improved the efficient that electronics injects to organic layer from negative electrode in the device, brightness, luminous efficiency and the life-span of having improved device, that has reduced device plays bright voltage and operating voltage.
Description of drawings
Fig. 1 is the basic block diagram of organic electroluminescence device of the present invention.
Fig. 2 is the current density-voltage curve of embodiment 1 and Comparative Examples 1 and Comparative Examples 2.
Fig. 3 is the brightness-voltage curve of embodiment 1 and Comparative Examples 1 and Comparative Examples 2.
Fig. 4 is the efficient-current density curve of embodiment 1 and Comparative Examples 1 and Comparative Examples 2.
Fig. 5 is the electron injecting layer surfaces A FM Top phasor of embodiment 1 and Comparative Examples 1 and Comparative Examples 2.
Fig. 6 is the electron injecting layer surfaces A FM Phase phasor of embodiment 1 and Comparative Examples 1 and Comparative Examples 2.
Fig. 7 is embodiment 1 and 1 life-span of Comparative Examples correlation curve.
Fig. 8 is the current density-voltage curve of embodiment 2 and Comparative Examples 1 and Comparative Examples 2.
Fig. 9 is the brightness-voltage curve of embodiment 2 and Comparative Examples 1 and Comparative Examples 2.
Figure 10 is the efficient-current density curve of embodiment 2 and Comparative Examples 1 and Comparative Examples 2.
Embodiment
Basic structure in the organic luminescent device that the present invention proposes as shown in Figure 1, wherein: 10 be transparent base, can be glass or flexible substrate, a kind of material in flexible substrate employing polyesters, the polyimides compounds; 20 is first electrode layer (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 ITO, zinc oxide, zinc tin oxide or gold, copper, silver, the optimized ITO that is chosen as, organic conductive polymer are preferably a kind of material in polythiophene/polyvinylbenzenesulfonic acid sodium (hereinafter to be referred as PEDOT:PSS), the polyaniline (hereinafter to be referred as PANI); 30 is the second electrode lay (cathode layer, metal level), 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, or the electrode layer that alternately forms of metal and metal fluoride; 40 is hole injection layer HIL (nonessential), and its host material can adopt copper phthalocyanine (CuPc), and the insulator polymer of doping adopts polytetrafluoroethylene (Teflon); 50 is hole transmission layer HTL, can adopt the arylamine class and the branch polymer same clan to hang down molecular material, is preferably NPB; 60 is organic luminous layer EML, generally adopts small molecule material, can be fluorescent material, as metal organic complex (as Alq3, Gaq
3, Al (Saph-q) or Ga (Saph-q)) compounds, can be doped with dyestuff in this small molecule material, doping content is the 0.01wt%～20wt% of small molecule material, dyestuff is generally a kind of material in aromatic condensed ring class (as rubrene), Coumarins (as DMQA, C545T) or two pyrans class (as DCJTB, the DCM) compound, the luminescent layer material also can adopt carbazole derivates such as CBP, polyvinylcarbazole (PVK), but Doping Phosphorus photoinitiator dye in this material is as three (2-phenylpyridine) iridium (Ir (PPy)
3), two (2-phenylpyridine) (acetylacetone,2,4-pentanedione) iridium (Ir (ppy)
2(acac)), octaethylporphyrin platinum (PtOEP) etc.; 70 is electron transfer layer, and materials used is the micromolecule electron transport material also, is generally metal organic complex (as Alq
3, Gaq
3, Al (Saph-q), BAlq or Ga (Saph-q)), aromatic condensed ring class (as pentacene, perylene) or o-phenanthroline class (as Bphen, BCP) compound; 80s is an electron injecting layer, for being the organic salt MBL of coordination center with the boron atom
4
For the purpose of reference, list the abbreviation of the organic material that relates in this specification and the full name table of comparisons as follows:
To provide some embodiment below also in conjunction with the accompanying drawings, specific explanations technical scheme of the present invention.Should be noted that the following examples only are used for helping to understand invention, rather than limitation of the present invention.
Embodiment 1:(device number: 1)
Glass/anode/NPB/Alq
3/LiBq
4/Al (1)
The concrete preparation method of organic electroluminescence device that preparation has above structural formula (1) is as follows:
1. utilize the ultrasonic and ultrasonic method of deionized water of the washing agent boil that glass substrate is cleaned, and be placed on infrared lamp under and dry, at evaporation one deck anode material on glass, thickness is 80～280nm;
2. the above-mentioned glass substrate that has anode is placed in the vacuum chamber, be evacuated to 5.0 * 10
-3The continuation evaporation hole transmission layer NPB on above-mentioned anode tunic of Pa, evaporation speed is 0.1nm/s, the evaporation thickness is 50nm;
3. on hole transmission layer, continue evaporation one deck Alq
3Material is as the electron transfer layer of device, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
4. on electron transfer layer, continue evaporation one deck LiBq
4As the electron injecting layer of device, its evaporation speed is 0.03-0.05nm/s, and the evaporation total film thickness is 1.0nm;
5. last, on above-mentioned electron transfer layer, continue the cathode layer of evaporating Al as device, its evaporation speed is 5-10nm/s, the evaporation total film thickness is 100nm.
The device that embodiment 1 is prepared, current density (as Fig. 2), brightness (as Fig. 3), current efficiency (as Fig. 4) all are higher than Comparative Examples 1, and are higher than Comparative Examples 2 far away.And playing bright voltage and operating voltage all decreases.It is 3.1V that embodiment 1 described device plays bright voltage (voltage when device brightness is 1cd/m2), and brightness is 9786cd/m during 12V
2, current efficiency is 3.39cd/A, is 3.5V and Comparative Examples 1 described device plays bright voltage, brightness is 6712cd/m during 12V
2, current efficiency is 3.35cd/A.
Embodiment is longer than Comparative Examples 1 described device 1 described device lifetime, Fig. 7 shown two not packaging original intensity under constant current state be 1000cd/m
2The life-span normalized curve.As can be seen from the figure, not the described device of Feng Zhuan embodiment partly the time of declining be 12 hours, and not the encapsulation Comparative Examples 1 described device be 8.5 hours.If above-mentioned two devices are encapsulated, partly the time of declining is expected to prolong.Because with respect to LiF, boracic metal organic salt evaporation condition is controlled easily, and filming performance is good, so the device of preparation plays bright voltage and operating voltage all decreases, and the current efficiency height, the life-span is long.
Fig. 5 and Fig. 6 have shown the Comparative Examples 2 that does not prepare the Al metal electrode respectively, the dynamic force mode atomic force microscopy of Comparative Examples 1 and embodiment 1 described device cathodes electron injecting layer (AFM in dynamic forcemode) surface topography map (Top mutually) with differ figure (Phase mutually).Top can reflect the surface undulation degree mutually, and Phase has write down needle point when vibration initial phase of atomic force microscope and feedback differing between mutually mutually, this differs and influenced by surface topography, interaction in needle point and surface mass is relevant, can distinguish the not homophase of different materials or same material.As deposition 0.7nm LiF or 1.0nm LiBq on the Alq3 film
4The time very little because thickness is extremely thin to the influence of Top surface topography, as seen from Figure 5 (b) and (c) in layer of substance is arranged attached to the Alq3 surface, and (b) be difficult to find out with (c) difference.But 0.7nm LiF or 1.0nm LiBq
4With respect to Alq
3Can produce enough phase shifts on the surface, promptly can be observed the deposition conditions of different materials on the surface, as can be seen from Figure 6, with respect to Alq
3Phase phase (d) (it is very big that phase is influenced by surface topography mutually, and therefore (d) duplicated Alq
3Island structure), (e) He (f) apparent in view difference is arranged, 0.7nm LiF (e) has only covered a surperficial part, and the part A lq that has
3Layer exposes out, and 1.0nm LiBq
4Much then even, except some Alq
3The peak is not by LiBq
4Cover.Uniform LiBq
4Film at evaporation can produce bigger effective electron behind the Al electrode and inject area, improve device performance, can effectively reduce Al and Alq simultaneously
3Directly contact, and this contact is to cause one of major reason that descends device lifetime, therefore with respect to the device of Comparative Examples 1, the device of embodiment 1 has the long life-span.
Embodiment 2:(device number: 2)
Preparation process is LiBq with embodiment 1
4Thickness is 0.5nm.The device current density (Fig. 8) of embodiment 2, brightness (Fig. 9) and current efficiency (Figure 10) are higher than Comparative Examples 2, but are lower than Comparative Examples 1.
Embodiment 3:(device number: 3)
Preparation process is LiBq with embodiment 1
4Thickness is 0.1nm.
Embodiment 4:(device number: 4)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (2-methyl-oxine) lithium borate of 1.0nm.
Embodiment 5:(device number: 5)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (the 8-hydroxy benzo pyrazine) lithium borate of 1.0nm.
Embodiment 6:(device number: 6)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (oxine) boric acid caesium of 2.0nm.
Embodiment 7:(device number: 7)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (2-methyl-oxine) the boric acid caesium of 1.0nm.
Embodiment 8:(device number: 8)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (oxine) line borate of 1.0nm.
Embodiment 9:(device number: 9)
Preparation process is with embodiment 1, and just electron injecting layer adopts thick four (2-methyl-oxine) antifungin of 1.0nm.
Comparative Examples 1:(device number: to 1)
Glass/anode/NPB/Alq
3/ LiF/Al (to 1)
Method according to embodiment 1 prepares the organic electroluminescence device with above structural formula (to 1), and difference is to use LiF to substitute LiBq during step 4.
4, its evaporation speed 0.03-0.05nm/s, the evaporation thickness is 0.7nm.
Comparative Examples 2:(device number: to 2)
Glass/anode/NPB/Alq
3/ Al (to 2)
Method according to embodiment 1 prepares the organic electroluminescence device with above structural formula (to 1), and difference is being removed electron injecting layer LiBq
4
The performance parameter of the foregoing description device is as shown in the table:
What embodiment provided is the organic electroluminescence device that contains anode layer, luminescent layer, cathode interface electron injecting layer and cathode layer device architecture, the common technique personnel of this area it should be understood that, one or more layers the organic electroluminescence device that further contains in the functional layers such as hole transmission layer, electron transfer layer, hole blocking layer also is fine, or adopts the device architecture of top outgoing also to be fine.Thought of the present invention is to insert the electron injecting layer that the ultra-thin organic salt by alkali metal containing or alkaline earth metal cation constitutes between metallic cathode and luminescent layer or metallic cathode and electron transfer layer, can effectively improve electronics injects, and then current density, brightness, the life-span of improving device, reduced bright voltage and operating voltage.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to the foregoing description and accompanying drawing, and under the guiding of the present invention's design, those skilled in the art can carry out various modifications and improvement, and claims have been summarized scope of the present invention.
Claims (12)
1. organic luminescent device, comprise substrate, anode and negative electrode, and between this to the organic light emitting medium layer between the electrode, also comprise the electron injecting layer between negative electrode and organic light emitting medium layer, it is characterized in that, this electron injecting layer comprises with the boron atom being the organic salt of coordination center, and its molecular formula is: MBL
4Wherein, M represents alkali metal or alkaline-earth metal, B represents the boron atom, L is monodentate ligand or bidentate ligand, be selected from following groups: oxine, 2-methyl-oxine, 8-hydroxy benzo pyrazine, 4-hydroxyl-1,5-naphthyridines, 5-hydroxyl-quinoxaline, 2-(2-hydroxy phenyl) benzoxazole, 2-(2-hydroxy phenyl) benzimidazole, 2-(2-hydroxy phenyl) benzothiazole, 10-hydroxy benzo quinoline or pyridine-2-formic acid.
2. according to the described device of claim 1, it is characterized in that electron injecting layer comprises that alkali-metal is the organic salt of coordination center with the boron atom.
3. according to claim 1 or 2 described devices, it is characterized in that what electron injecting layer comprised lithium is the organic salt of coordination center with the boron atom.
4. according to claim 1 or 2 described devices, it is characterized in that what electron injecting layer comprised caesium is the organic salt of coordination center with the boron atom.
5. according to the described device of claim 1, it is characterized in that what electron injecting layer comprised alkaline-earth metal is the organic salt of coordination center with the boron atom.
6. according to claim 1 or 5 described devices, it is characterized in that what electron injecting layer comprised magnesium is the organic salt of coordination center with the boron atom.
7. according to claim 1 or 5 described devices, it is characterized in that what electron injecting layer comprised calcium is the organic salt of coordination center with the boron atom.
8. according to the described device of claim 1, it is characterized in that the electron injecting layer material is four (oxine) lithium borate, four (2-methyl-oxine) lithium borate, four (8-hydroxy benzo pyrazine) lithium borate.
9. according to the described device of claim 1, it is characterized in that the electron injecting layer material is four (oxine) boric acid caesium, four (2-methyl-oxine) boric acid caesium, four (8-hydroxy benzo pyrazine) boric acid caesium.
10. according to the described device of claim 1, it is characterized in that the electron injecting layer thickness range is 0.1nm to 2nm.
11., it is characterized in that the electron injecting layer thickness range is 0.1nm to 1nm according to the described device of claim 10.
12. according to the described device of claim 1, it is characterized in that cathode material is selected Al for use, Ca, Ba, a kind of in Mg or the Mg:Ag alloy.
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| JP2005142122A (en) * | 2003-11-10 | 2005-06-02 | Canon Inc | Organic light emitting element having metal borate or organic boron compound of metal |
| US20050123789A1 (en) * | 2003-12-05 | 2005-06-09 | Vargas J. R. | Organic element for electroluminescent devices |
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| JP2005142122A (en) * | 2003-11-10 | 2005-06-02 | Canon Inc | Organic light emitting element having metal borate or organic boron compound of metal |
| US20050123789A1 (en) * | 2003-12-05 | 2005-06-09 | Vargas J. R. | Organic element for electroluminescent devices |
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Address after: No. 1 East Road, Beijing, Haidian District ocean building, first floor 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 |