CN109473558A - A kind of inert metal n-type dopant and its application in organic electroluminescence device - Google Patents
A kind of inert metal n-type dopant and its application in organic electroluminescence device Download PDFInfo
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Abstract
The invention belongs to organic electroluminescence device technical fields, and in particular to one kind is based on inert metal n-type dopant, and further discloses its application and its application in organic electroluminescence device as electron transport material dopant.It is of the present invention to be based on inert metal n-type dopant, including inert metal and with the ligand compound for matching bit function, the dopant is doped in conventional electrical transmission material of main part, the lumo energy of electron transport material can be effectively reduced, and then promote the injection of electronics, to significantly reduce the driving voltage of device, the efficiency of device is improved.
Description
Technical field
The invention belongs to organic electroluminescence device technical fields, and in particular to one kind is based on inert metal n-type doping
Agent, and its application as electron transport material dopant and its answering in organic electroluminescence device are further disclosed
With.
Background technique
Organic Light Emitting Diode (OLED) is a kind of multilayer organic thin film structure, can be by electroluminescent device.It is gathered around
There are many display characteristics and quality that surmount LCD (liquid crystal display) to have by good characteristics such as its low energy consumption and flexibilities
Good application prospect will become next-generation mainstream flat-panel monitor.
In OLED, the lumo energy of usually used electron transport material (ETM) is near -3.0eV, and metallic cathode
Work function be generally higher than 4.0eV, therefore, when electronics is directly injected into electron transfer layer from metallic cathode, there are biggish
Energy gap hinders the injection of electronics, so that device drive voltage is higher, while the electron hole for reach in luminescent layer is uneven,
It reduces device efficiency and shortens device lifetime.Therefore, it is possible to use the method for n-type doping is to improve the biography of electron transport material
Defeated characteristic reduces the lumo energy of electron transport material, and then promotes injection of the electronics from electrode.The mechanism of n-type doping is benefit
It is transferred an electron on the lumo energy of ETM with n- dopant, to realize the transfer of charge, improves free carrier concentration.
Since the lumo energy of electron transport material is in -3.0eV or so, this requires the work function of dopant must in 3.0eV hereinafter,
It could efficiently transfer an electron on the lumo energy of ETM.But general work function is less than the substance of 3.0eV, reproducibility
It is very strong, it is easy to it is aoxidized by the oxygen in air, therefore, the type of the presently found n-type dopant suitable for OLED
It is less.In the n-type dopant being currently known, the most commonly used is alkali metal, since the work function of alkali metal is respectively less than 3.0eV, because
Efficient n-type doping effect may be implemented in alkali metal and ETM codope by this.However, the performance of alkali metal is but especially living
Sprinkle, be easily oxidized in air, the metals such as sodium, potassium, caesium even can spontaneous combustion in air, therefore, it is difficult to store for a long time, and
And operation is also more inconvenient.It can although thermally decomposing the method in situ for generating active alkali metal in vacuum by alkali metal compound
To avoid active alkali metal is directly used in air, to enhance its aerial stability, however alkali metal compound
There is also serious phenomenon of deflation when decomposing in a vacuum, keep vacuum degree when evaporated film poor, lead to film forming and atmosphere
It is unstable, it is difficult to obtain practical application.Separately there are the companies such as the Saes of Japan by way of changing cladding to stablize this kind of work
Metal material is sprinkled, but such preparation process is then sufficiently complex, is also unfavorable for promoting the use of on a large scale.In contrast, inertia
Metal in air stablize by performance, can store and use for a long time, however since its work function is larger, it cannot occur between ETM
Electric charge transfer, therefore there is no the effect of n-type doping, not a kind of good n-type dopants.
Currently, having open report display that inert metal thin layer Ag is deposited on 1nm to Bphen or BCP, in interface Ag
It can have an effect with Bphen or BCP, to improve the injection of electronics.Although there is certain effect in this way, Ag passes through infiltration
Penetrate into Bphen[4,7- diphenyl -1,10- ferrosin] or BCP[2,9- dimethyl -4,9- diphenyl -1,10- ferrosin]
Amount it is limited, be only capable of being formed mechanism and indefinite that is compound, and acting in interface.Chinese patent CN201110325422.2
It is open to propose with active metal M doping ETM to realize n-type doping effect, wherein itself work function of this kind of active metal compared with
It is low, the n-type dopant of strong reducing property is directly served as, and unstable in air, it is difficult to which long-term storage and use are unfavorable for
Industrial production.
Summary of the invention
For this purpose, it is a kind of based on inert metal n-type dopant technical problem to be solved by the present invention lies in providing, it uses
Coordination occurs for ligand and inert metal with coordination ability instead as n-type dopant, the dopant and electron transport material
It answers, inert metal is promoted to lose the process of electronics, to reduce the work function of inert metal, inert metal is made also to be able to achieve and live
The similar n-type doping effect of metal is sprinkled, reduces the lumo energy of electron transport material, and then reduce the injection barrier of electronics, from
And it significantly reduces device drive voltage, improve device efficiency.
In order to solve the above technical problems, it is of the present invention be based on inert metal n-type dopant, including inert metal and
With the ligand compound for matching bit function；The inert metal and with bit function ligand compound mass ratio be 1-
50:100, and preferred 20:100.
The inert metal is the metal that stable in the air and work function is higher than 4.0eV.
The inert metal be titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu),
Zinc (Zn), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), lead (Pd), silver-colored (Ag), cadmium (Cd), tantalum (Ta),
One of tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), golden (Au), platinum (Pt), mercury (Hg) or in which several mixtures.
The inert metal be the stronger metallic atom of coordination ability, including cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru),
Silver-colored (Ag), iridium (Ir), gold one of (Au) or platinum (Pt) or in which several mixtures.
It is described that there is the structure as shown in following formula (L1)-formula (L16) with the ligand compound with bit function:
The invention also discloses the n-type dopants to be used to prepare the doping of organic electroluminescence device electron transfer layer
The application of material.
The invention also discloses a kind of organic electroluminescence devices, including substrate, and sequentially form on the substrate
Luminescent device, the luminescent device includes first electrode layer, luminescent layer, electron transfer layer and the second electrode lay；
The electron transfer layer includes electron-transport material of main part and the institute that is entrained in the electron-transport material of main part
The n-type dopant stated.
The n-type dopant is 1vol%-99vol% in the doping ratio of the electron transfer layer.
Preferably, doping ratio of the n-type dopant in the electron transfer layer is 5vol%-30vol%.
The device further includes that the hole injection layer being arranged between the first electrode layer and luminescent layer and/or hole pass
Hole blocking layer between defeated layer and the luminescent layer and electron transfer layer.
N-type dopant of the present invention include inert metal and with match bit function ligand compound, the ligand
Compound has with preferable with bit function, and the n-type dopant and existing conventional electrical transmission material are doped,
Using the coordination of the ligand compound, ETM and Mn+ can to that coordination occur to promote inert metal M to lose electronics,
Its work function is reduced, so that inert metal realizes the n-type doping effect similar with active alkali metal, improves electron transport material
Transmission characteristic reduces the injection barrier of electronics, enhances the injection of electronics.By the above mechanism of action, so that inert metal also can
Realize the similar n-type dopant in active metal, be a kind of new n-type doping thinking, can to avoid using active alkali metal,
Cheap, stable and efficient OLED device is prepared, the scope of application based on inert metal n-type doping has been further expanded.
The material that the present invention uses is inert metal, stable in the air, is stored and easy to use, can be repeatedly sharp
With being conducive to industrial production；And phenomenon of deflation is not present, vapor deposition atmosphere is relatively stable, can be produced in batches.The doping
After agent and electron transport material doping, the transmission characteristic of electron transport material is helped to improve, electron transport material is reduced
Lumo energy can preferably be matched with cathode, reduced electron injection barrier, improved the injection efficiency of electronics；Inert metal compared with
It is more, it can choose the lower inert metal of some vapor deposition temperature, select face than wide；Electron transport material is organic material,
Thermal stability is poor, after adulterating inorganic inert metal formation complex, significantly improves its thermal stability.
Detailed description of the invention
In order to make the content of the present invention more clearly understood, it below according to specific embodiments of the present invention and combines
Attached drawing, the present invention is described in further detail, wherein
Fig. 1 is the structural schematic diagram of organic electroluminescence device of the invention；
Fig. 2 is the performance test results of device described in the embodiment of the present invention 1；
Appended drawing reference indicates in figure are as follows: 01- substrate, 02- first electrode layer, and 03- the second electrode lay, 04- hole injection layer,
05- hole transmission layer, 06- luminescent layer, 07- hole blocking layer, 08- electron transfer layer.
Specific embodiment
The present invention can be embodied in many different forms, and should not be construed as limited to embodiment set forth herein.
On the contrary, providing these embodiments, so that the disclosure will be thorough and complete, and design of the invention will be fully conveyed to
Those skilled in the art, the present invention will only be defined by the appended claims.In the accompanying drawings, for clarity, the area Ceng He can be exaggerated
The size and relative size in domain.It should be understood that when element such as layer, region or substrate are referred to as " being formed in " or " setting
" another element "upper" when, which can be arranged directly on another element, or there may also be intermediary elements.
On the contrary, intermediary element is not present when element is referred to as on " being formed directly into " or " being set up directly on " another element.
Organic electroluminescence device as shown in Figure 1, including substrate 01, and the hair being sequentially formed on the substrate 01
Optical device, the luminescent device include first electrode layer 02 (anode), hole injection layer 04, hole transmission layer 05, luminescent layer 06,
Hole blocking layer 07, electron transfer layer 08 and the second electrode lay 03 (cathode)；
The electron transfer layer 08 includes known conventional electrical transmission material of main part and is entrained in the electron-transport master
N-type dopant in body material；The doping ratio of the n-type dopant is 1vol%-99vol%, preferably 5vol%-
30vol%.
It is described based on inert metal n-type dopant, including inert metal and with the ligand compound for matching bit function；
The inert metal and mass ratio with the ligand compound with bit function are 1-50:100, and preferably 20:100.
The inert metal is the metal that stable in the air and work function is higher than 4.0eV.
The inert metal be titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu),
Zinc (Zn), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), lead (Pd), silver-colored (Ag), cadmium (Cd), tantalum (Ta),
One of tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), golden (Au), platinum (Pt), mercury (Hg) or in which several mixtures.
The inert metal be the stronger metallic atom of coordination ability, including cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru),
Silver-colored (Ag), iridium (Ir), gold one of (Au) or platinum (Pt) or in which several mixtures.
It is described that there is the structure as shown in following formula (L1)-formula (L16) with the ligand compound with bit function:
The preparation process of organic electroluminescence device of the invention is compared with technology, the wherein preparation side of electron transfer layer 08
Method is conventional vacuum evaporation technology.
The evaporation rate of metal should be relatively slow, is 0.1 angstroms per second, under this rate, the material of main part of electron transfer layer and doping
Material is more abundant with contacting between the compound and inert metal of coordination property, so that inert metal M and ligand L igand
Disperse in material of main part ETM more uniform, is conducive to compound.
Embodiment 1
The structure of single-electron device:
ITO/Bphen (100nm)/Ag or Au:ETM:Ligand=(1:1:10,1:1:5,1:2:5,1:2:10,5-
100nm)/Al；
First electrode layer 02 (anode ITO)/hole blocking layer 07 (Bphen)/08 (x%M-Ligand- of electron transfer layer
ETM)/the second electrode lay 03 (cathode Al).
The material of main part ETM structure such as following formula (a) of electron transfer layer in the present embodiment, the inert metal of doping be Ag or
Au。
As shown in Fig. 2, device 1 is the corresponding curve of ETM/Al, device 2 is the corresponding curve of Ag-ETM-Ligand1/Al,
Device 3 is the corresponding curve of Ag-ETM-Ligand2/Al, and device 4 is the corresponding curve of Au-ETM-Ligand1/Al, and device 5 is
The corresponding curve of Au-ETM-Ligand2/Al, the cathode of device 1-5 are Al, in which:
1 electron transfer layer 08 of device is electron transport material shown in formula (a) (undope n-type dopant)；
The electron transport material that electron transfer layer 08 (20%M-Ligand-ETM) in device 2 uses is Ag-Ligand1
Dopant and ETM codope, doping ratio 20vol%, i.e., doped with 20 angstroms of n- in 100 angstroms of electron-transport material of main part
Type dopant；The n- dopant includes ligand compound shown in the inert metal Ag that mass ratio is 1:1 and formula (L6)；
The electron transport material that electron transfer layer 08 (40%M-Ligand-ETM) in device 3 uses is Ag-Ligand2
Dopant and ETM codope, doping ratio 40vol%, i.e., doped with 40 angstroms of n- in 100 angstroms of electron-transport material of main part
Type dopant；The n- dopant includes ligand compound shown in the inert metal Ag that mass ratio is 1:1 and formula (L16)；
The electron transport material that electron transfer layer 08 (60%M-Ligand-ETM) in device 4 uses is Au-Ligand1
Dopant and ETM codope, doping ratio 60vol%, i.e., doped with 60 angstroms of n- in 100 angstroms of electron-transport material of main part
Type dopant；The n- dopant includes ligand compound shown in the inert metal Au that mass ratio is 1:2 and formula (L6)；
The electron transport material that electron transfer layer 08 (30%M-Ligand-ETM) in device 5 uses is Au-Ligand2
Dopant and ETM codope, doping ratio 30vol%, i.e., doped with 30 angstroms of n- in 100 angstroms of electron-transport material of main part
Type dopant；The n- dopant includes ligand compound shown in the inert metal Au that mass ratio is 1:1 and formula (L16)；
Above-mentioned device 1, device 2, device 3, device 4 and 5 current density voltage curve figure of device are shown in Fig. 2, can be with by Fig. 2
Find out using n-type dopant of the present invention and routine ETM material of main part codope as electron transfer layer, height may be implemented
The electron injection of effect.
Embodiment 2
Device architecture:
ITO/HAT-CN(10nm)/NPB(30nm)/Alq3(30nm)/Bphen (20nm)/x%M-Ligand-ETM
10nm/Ag；
First electrode layer 02 (anode ITO), hole injection layer 04 (HAT-CN), hole transmission layer 05 (NPB), luminescent layer 06
(Alq3), hole blocking layer 07 (Bphen), electron transfer layer 08 (x%M-Ligand-ETM), 03 (cathode of the second electrode lay
Ag)。
The material of main part of electron transfer layer described in the present embodiment is TPBI, has structure as follows:
The selection of the material of main part of electron transfer layer described in the present embodiment, the inert metal of doping, ligand compound, with
And the composition ratio x% and doping ratio of the dopant see the table below 1 respectively, and be doped to comparing device with existing active metal
Part.
The selection of each device material of table 1
| Device number | M | Ligand | M:Ligand | ETM | It mixes and compares vol% |
| Device 6 | Cu | Formula 6 | 20% | TPBI | 10% |
| Device 7 | Ag | Formula 6 | 20% | TPBI | 10% |
| Device 8 | Au | Formula 6 | 20% | TPBI | 10% |
| Device 9 | Pd | Formula 6 | 20% | TPBI | 10% |
| Device 10 | Ir | Formula 6 | 20% | TPBI | 10% |
| Device 11 | Pt | Formula 6 | 20% | TPBI | 10% |
| Device 12 | Ru | Formula 6 | 20% | TPBI | 10% |
| Device 13 | Rh | Formula 6 | 20% | TPBI | 10% |
| Device 14 | Fe | Formula 6 | 20% | TPBI | 10% |
| Control device 1 | Ag | Nothing | - | TPBI | 10% |
| Control device 2 | Cs | TPBI | 10% |
As it can be seen that the n-type dopant and existing conventional electrical transmission material are doped by scheme of the present invention, benefit
It, can be by ETM and M with the coordination of the ligand compoundn+Coordination occurs to promote inert metal M to lose electronics, drops
Its low work function improves the biography of electron transport material so that inert metal realizes the n-type doping effect similar with active alkali metal
Defeated characteristic reduces the injection barrier of electronics, enhances the injection of electronics.
Embodiment 3
Device architecture:
ITO/HATCN(10nm)/NPB(30nm)/Alq3(30nm)/Bphen (20nm)/x%M-Ligand-ETM
10nm/Mg:Ag/Ag；
First electrode layer 02 (anode ITO), hole injection layer 04 (HATCN), hole transmission layer 05 (NPB), luminescent layer 06
(Alq3), hole blocking layer 07 (Bphen), electron transfer layer 08 (x%M-Ligand-ETM), the second electrode lay 03 (cathode Mg:
Ag/Ag)。
The material of main part of electron transfer layer described in the present embodiment has structure (all H of R) shown in following (b):
The selection of the material of main part of electron transfer layer described in the present embodiment, the inert metal of doping, ligand compound, with
And the composition ratio x% and doping ratio of the dopant see the table below 2 respectively, and be doped to comparing device with existing active metal
Part.
The selection of each device material of table 2
| Device number | M | Ligand | M:Ligand | ETM | It mixes and compares vol% |
| Device 15 | Cu | Formula 6 | 20% | ETM(b) | 10% |
| Device 16 | Ag | Formula 6 | 20% | ETM(b) | 10% |
| Device 17 | Au | Formula 6 | 20% | ETM(b) | 10% |
| Device 18 | Pd | Formula 6 | 20% | ETM(b) | 10% |
| Device 19 | Ir | Formula 6 | 20% | ETM(b) | 10% |
| Device 20 | Pt | Formula 6 | 20% | ETM(b) | 10% |
| Device 21 | Ru | Formula 6 | 20% | ETM(b) | 10% |
| Device 22 | Rh | Formula 6 | 20% | ETM(b) | 10% |
| Device 23 | Fe | Formula 6 | 20% | ETM(b) | 10% |
| Control device 3 | Ag | Nothing | - | ETM(b) | 10% |
| Control device 4 | Cs | ETM(b) | 10% |
As it can be seen that the device performance of the present invention doped with the dopant is better than the performance of prior art control device.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. one kind is based on inert metal n-type dopant, which is characterized in that including inert metal and with the ligand for matching bit function
Compound；The inert metal and with bit function ligand compound mass ratio be 1-50:100.
2. according to claim 1 be based on inert metal n-type dopant, which is characterized in that the inert metal is in sky
Stable and work function is higher than the metal of 4.0eV in gas.
3. according to claim 2 be based on inert metal n-type dopant, which is characterized in that the inert metal is titanium
(Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), zirconium (Zr), niobium (Nb), molybdenum
(Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), lead (Pd), silver (Ag), cadmium (Cd), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium
(Ir), one of golden (Au), platinum (Pt), mercury (Hg) or in which several mixtures.
4. according to claim 3 be based on inert metal n-type dopant, which is characterized in that the inert metal is coordination
The stronger metallic atom of ability, including cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru), silver-colored (Ag), iridium (Ir), golden (Au) or platinum
Or in which several mixtures one of (Pt).
5. it is according to claim 1-4 be based on inert metal n-type dopant, which is characterized in that it is described have match
The ligand compound of bit function has the structure as shown in following formula (L1)-formula (L16):
6. the described in any item n-type dopants of claim 1-5 are used to prepare the doping of organic electroluminescence device electron transfer layer
The application of material.
7. a kind of organic electroluminescence device, including substrate (01), and luminescent device on the substrate is sequentially formed, institute
Stating luminescent device includes first electrode layer (02), luminescent layer (06), electron transfer layer (08) and the second electrode lay (03)；Its feature
It is,
The electron transfer layer (08) include electron-transport material of main part and be entrained in the electron-transport material of main part as
The described in any item n-type dopants of claim 1-5.
8. organic electroluminescence device according to claim 7, which is characterized in that the n-type dopant is in the electronics
Doping ratio in transport layer is 1vol%-99vol%.
9. organic electroluminescence device according to claim 8, which is characterized in that the n-type dopant is in the electronics
Doping ratio in transport layer is 5vol%-30vol%.
10. according to the described in any item organic electroluminescence devices of claim 7-9, which is characterized in that the device further includes
The hole injection layer (04) and/or hole transmission layer (05) being arranged between the first electrode layer (02) and luminescent layer (06),
And the hole blocking layer (07) between the luminescent layer (06) and electron transfer layer (08).
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| CN112614955A (en) * | 2020-12-17 | 2021-04-06 | 北京维信诺科技有限公司 | Organic light emitting diode, display panel, preparation methods and display device |
| CN113611805A (en) * | 2020-08-14 | 2021-11-05 | 广东聚华印刷显示技术有限公司 | Light emitting device, method of manufacturing the same, and light emitting apparatus |
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