CN109473558B - N-type dopant of inert metal and application thereof in organic electroluminescent device - Google Patents
N-type dopant of inert metal and application thereof in organic electroluminescent device Download PDFInfo
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Abstract
The invention belongs to the technical field of organic electroluminescent devices, and particularly relates to an n-type dopant based on inert metal, and further discloses application of the n-type dopant as an electron transport material dopant and application of the n-type dopant in an organic electroluminescent device. The n-type dopant based on the inert metal comprises the inert metal and a ligand compound with a coordination function, and the dopant is doped in a conventional electron transport host material, so that the LUMO energy level of the electron transport material can be effectively reduced, the injection of electrons is promoted, the driving voltage of a device is remarkably reduced, and the efficiency of the device is improved.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent devices, and particularly relates to an n-type dopant based on inert metal, and further discloses application of the n-type dopant as an electron transport material dopant and application of the n-type dopant in an organic electroluminescent device.
Background
An Organic Light Emitting Diode (OLED) is a device of a multilayer organic thin film structure that can emit light by electroluminescence. The display has various display characteristics and quality superior to those of an LCD (liquid crystal display), has good application prospect by virtue of excellent characteristics such as low energy consumption, flexibility and the like, and becomes a next-generation main flat panel display.
In an OLED, a commonly used Electron Transport Material (ETM) has a LUMO level around-3.0 eV, while the work function of a metal cathode is generally greater than 4.0eV, and thus, when electrons are directly injected from the metal cathode into an electron transport layer, there is a large energy gap to hinder the injection of electrons, so that a device driving voltage is high, while electron-hole reaching into a light emitting layer is unbalanced, decreasing device efficiency and shortening device lifetime. Therefore, an n-type doping method may be used to improve the transport characteristics of the electron transport material, lower the LUMO level of the electron transport material, and thus facilitate the injection of electrons from the electrode. The mechanism of n-type doping is to transfer electrons to the LUMO level of the ETM using an n-dopant, thereby achieving charge transfer and increasing the free carrier concentration. Since the LUMO level of the electron transporting material is around-3.0 eV, this requires that the work function of the dopant must be below 3.0eV in order to efficiently transfer electrons to the LUMO level of the ETM. However, substances having a work function of less than 3.0eV are generally very reductive and easily oxidized by oxygen in the air, and thus, there are few types of n-type dopants that have been found to be suitable for use in OLEDs. Among the currently known n-type dopants, alkali metals are most commonly used, and since the work functions of the alkali metals are all less than 3.0eV, co-doping the alkali metals with ETM can achieve a highly efficient n-type doping effect. However, alkali metals are particularly active and are very easily oxidized in air, and metals such as sodium, potassium and cesium can spontaneously combust in air, so that the alkali metals are difficult to store for a long time and are inconvenient to operate. Although the method of in-situ generation of active alkali metal by the alkali metal compound in vacuum thermal decomposition can avoid the direct use of active alkali metal in air to enhance the stability of the active alkali metal in air, the alkali metal compound also has a serious outgassing phenomenon during the vacuum decomposition, so that the vacuum degree during the film evaporation is poor, the film forming property and the atmosphere are unstable, and the practical application is difficult to obtain. In addition, the companies such as Saes in japan stabilize such active metal materials by changing the coating method, but such a preparation process is very complicated and is not suitable for wide-scale popularization and use. In contrast, inert metals are stable in air and can be stored and used for a long time, but because of their large work function, no charge transfer can occur with ETM, and therefore they do not have n-type doping effect and are not a good n-type dopant.
At present, there is a public report that an inert metal thin layer Ag is evaporated on Bphen or BCP by 1nm, and the Ag can react with the Bphen or BCP at an interface to improve the injection of electrons. Although this has some effect, the amount of Ag that enters Bphen [ 4, 7-diphenyl-1, 10-phenanthroline ] or BCP [ 2, 9-dimethyl-4, 9-diphenyl-1, 10-phenanthroline ] by permeation is limited, and only a complex can be formed at the interface, and the mechanism of action is unclear. Chinese patent CN201110325422.2 discloses that ETM is doped with active metal M to realize n-type doping effect, wherein the active metal has low work function itself, directly acts as n-type dopant with strong reducibility, is unstable in air, is difficult to store and use for a long time, and is not beneficial to industrial production.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide an n-type dopant based on an inert metal, wherein a ligand with coordination capacity and the inert metal are used as the n-type dopant, the dopant and an electron transport material generate a coordination reaction to promote the process of losing electrons of the inert metal, so that the work function of the inert metal is reduced, the inert metal can realize an n-type doping effect similar to that of an active metal, the LUMO energy level of the electron transport material is reduced, the injection barrier of electrons is further reduced, and the driving voltage of a device is remarkably reduced, and the efficiency of the device is improved.
In order to solve the above technical problems, the inert metal-based n-type dopant according to the present invention includes an inert metal and a ligand compound having a coordination function; the mass ratio of the inert metal to the ligand compound with the coordination function is 1-50: 100, and preferably 20: 100.
the inert metal is a metal that is stable in air and has a work function higher than 4.0 eV.
The inert metal is one or a mixture of several of 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), gold (Au), platinum (Pt) and mercury (Hg).
The inert metal is a metal atom with strong coordination capacity, and comprises one or a mixture of several of cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru), silver (Ag), iridium (Ir), gold (Au) or platinum (Pt).
The ligand compound having a coordinating function has a structure represented by the following formula (L1) -formula (L16):
the invention also discloses application of the n-type dopant in preparing a doping material of an electron transport layer of an organic electroluminescent device.
The invention also discloses an organic electroluminescent device, which comprises a substrate and a luminescent device sequentially formed on the substrate, wherein the luminescent device comprises a first electrode layer, a luminescent layer, an electron transport layer and a second electrode layer;
the electron transport layer includes an electron transport host material and the n-type dopant doped in the electron transport host material.
The doping proportion of the n-type dopant in the electron transport layer is 1vol% -99 vol%.
Preferably, the doping ratio of the n-type dopant in the electron transport layer is 5vol% to 30 vol%.
The device further comprises a hole injection layer and/or a hole transport layer arranged between the first electrode layer and the light-emitting layer, and a hole blocking layer arranged between the light-emitting layer and the electron transport layer.
The n-type dopant comprises an inert metal and a ligand compound with a coordination function, wherein the ligand compound has a better coordination function, the n-type dopant is doped with the conventional electron transport material, and by utilizing the coordination function of the ligand compound, ETM and Mn + can be subjected to coordination to promote the inert metal M to lose electrons and reduce the work function of the inert metal M, so that the inert metal realizes an n-type doping effect similar to that of active alkali metal, the transport property of the electron transport material is improved, the injection barrier of electrons is reduced, and the injection of electrons is enhanced. Through the action mechanism, the inert metal can also realize an N-type dopant similar to the active metal, so that the method is a new N-type doping idea, active alkali metal can be avoided, the OLED device which is cheap, stable and efficient is prepared, and the application range of the inert metal-based N-type doping is further expanded.
The material adopted by the invention is inert metal, which is stable in air, convenient to store and use, can be repeatedly utilized and is beneficial to industrial production; and no gassing phenomenon exists, the evaporation atmosphere is relatively stable, and batch production can be carried out. After the dopant is doped with the electron transport material, the transmission characteristic of the electron transport material is improved, the LUMO energy level of the electron transport material is reduced, the electron transport material can be better matched with a cathode, an electron injection barrier is reduced, and the electron injection efficiency is improved; the inert metal is more, some inert metals with lower evaporation temperature can be selected, and the selection range is wider; the electron transport material is an organic material, has poor thermal stability, and is doped with inorganic inert metal to form a complex, so that the thermal stability of the complex is obviously improved.
Drawings
In order that the present disclosure may be more readily and clearly understood, the following detailed description of the present disclosure is provided in connection with specific embodiments thereof and the accompanying drawings, in which,
FIG. 1 is a schematic structural view of an organic electroluminescent device according to the present invention;
FIG. 2 shows the results of performance testing of the device described in example 1 of the present invention;
the reference numbers in the figures denote: 01-substrate, 02-first electrode layer, 03-second electrode layer, 04-hole injection layer, 05-hole transport layer, 06-light-emitting layer, 07-hole blocking layer, 08-electron transport layer.
Detailed Description
This invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete and will fully convey the concept of the invention to those skilled in the art, and the present invention will only be defined by the appended claims. In the drawings, the size and relative sizes of layers and regions may be exaggerated for clarity. It will be understood that when an element such as a layer, region or substrate is referred to as being "formed on" or "disposed on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly formed on" or "directly disposed on" another element, there are no intervening elements present.
The organic electroluminescent device as shown in fig. 1 comprises a substrate 01, and a light-emitting device formed on the substrate 01 in sequence, wherein the light-emitting device comprises a first electrode layer 02 (anode), a hole injection layer 04, a hole transport layer 05, a light-emitting layer 06, a hole blocking layer 07, an electron transport layer 08 and a second electrode layer 03 (cathode);
the electron transport layer 08 includes a known conventional electron transport host material and an n-type dopant doped in the electron transport host material; the doping proportion of the n-type dopant is 1vol% to 99vol%, preferably 5vol% to 30 vol%.
The inert metal-based n-type dopant includes an inert metal and a ligand compound having a coordination function; the mass ratio of the inert metal to the ligand compound with the coordination function is 1-50: 100, and preferably 20: 100.
the inert metal is a metal that is stable in air and has a work function higher than 4.0 eV.
The inert metal is one or a mixture of several of 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), gold (Au), platinum (Pt) and mercury (Hg).
The inert metal is a metal atom with strong coordination capacity, and comprises one or a mixture of several of cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru), silver (Ag), iridium (Ir), gold (Au) or platinum (Pt).
The ligand compound having a coordinating function has a structure represented by the following formula (L1) -formula (L16):
the preparation process of the organic electroluminescent device is the same as that of the prior art, wherein the preparation method of the electron transport layer 08 is the conventional vacuum evaporation technology.
The evaporation rate of the metal is relatively low and is 0.1 angstrom/second, and at the rate, the contact between the compound with coordination performance of the main material and the doping material of the electron transport layer and the inert metal is relatively sufficient, so that the inert metal M and the Ligand are dispersed in the main material ETM more uniformly, and the composite is facilitated.
Example 1
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)/electron transport layer 08 (x% M-Ligand-ETM)/second electrode layer 03 (cathode Al).
The host material ETM of the electron transport layer in this embodiment has the following structure (a), and the doped inert metal is Ag or Au.
As shown in FIG. 2, the curve corresponding to ETM/Al is shown in the device 1, the curve corresponding to Ag-ETM-Ligand1/Al is shown in the device 2, the curve corresponding to Ag-ETM-Ligand2/Al is shown in the device 3, the curve corresponding to Au-ETM-Ligand1/Al is shown in the device 4, the curve corresponding to Au-ETM-Ligand2/Al is shown in the device 5, and the cathodes of the devices 1-5 are all made of Al, wherein:
the electron transport layer 08 of the device 1 is an electron transport material represented by formula (a) (i.e., is not doped with an n-type dopant);
the electron transport layer 08 (20% M-Ligand-ETM) in the device 2 adopts an electron transport material of Ag-Ligand1 dopant and ETM co-doping, and the doping proportion is 20 vol%, namely, the electron transport main body material with 100 angstroms is doped with 20 angstroms of n-type dopant; the n-dopant comprises the following components in a mass ratio of 1: 1 and a ligand compound represented by formula (L6);
the electron transport layer 08 (40% M-Ligand-ETM) in the device 3 adopts an electron transport material of Ag-Ligand2 dopant and ETM co-doping, and the doping proportion is 40 vol%, namely 100 angstroms of electron transport main body material is doped with 40 angstroms of n-type dopant; the n-dopant comprises the following components in a mass ratio of 1: 1 and a ligand compound represented by formula (L16);
the electron transport layer 08 (60% M-Ligand-ETM) in the device 4 adopts an electron transport material of Au-Ligand1 dopant and ETM co-doping, and the doping proportion is 60 vol%, namely, the electron transport main body material with 100 angstroms is doped with 60 angstroms of n-type dopant; the n-dopant comprises the following components in a mass ratio of 1: 2 and a ligand compound represented by the formula (L6);
the electron transport layer 08 (30% M-Ligand-ETM) in the device 5 adopts an electron transport material of Au-Ligand2 dopant and ETM co-doping, and the doping proportion is 30vol%, namely, 100 angstroms of electron transport host material is doped with 30 angstroms of n-type dopant; the n-dopant comprises the following components in a mass ratio of 1: 1 and a ligand compound represented by the formula (L16);
the current density-voltage curve of the devices 1, 2, 3, 4 and 5 is shown in fig. 2, and it can be seen from fig. 2 that the n-type dopant of the present invention and the conventional ETM host material are co-doped to serve as an electron transport layer, so that efficient electron injection can be achieved.
Example 2
The device structure is as follows:
ITO/HAT-CN(10nm)/NPB(30nm)/Alq3(30nm)/Bphen(20nm)/x％M-Ligand-ETM10nm/Ag；
first electrode layer 02 (anode ITO), hole injection layer 04(HAT-CN), hole transport layer 05(NPB), and light-emitting layer 06 (Alq)3) A hole blocking layer 07(Bphen), an electron transport layer 08 (x% M-Ligand-ETM), and a second electrode layer 03 (cathode Ag).
The host material of the electron transport layer in this embodiment is TPBI, and has the following structure:
the selection of the host material, the doped inert metal, and the ligand compound of the electron transport layer in this embodiment, and the composition ratio x% and the doping ratio of the dopant are shown in table 1 below, respectively, and the existing active metal doping is used as a comparison device.
TABLE 1 selection of device materials
| Device numbering | M | Ligand | M：Ligand | ETM | The mixing ratio is 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％ |
| Comparison device 1 | Ag | Is free of | - | |
10％ |
| Comparison device 2 | Cs | TPBI | 10％ |
As can be seen, the scheme of the invention dopes the n-type dopant with the conventional electron transport material, and the coordination of the ligand compound is utilized to mix ETM and Mn+The coordination action is carried out to promote the inert metal M to lose electrons, the work function of the inert metal M is reduced, the inert metal realizes the n-type doping effect similar to that of active alkali metal, the transmission characteristic of the electron transmission material is improved, the injection barrier of electrons is reduced, and the injection of electrons is enhanced.
Example 3
The device structure is as follows:
ITO/HATCN(10nm)/NPB(30nm)/Alq3(30nm)/Bphen(20nm)/x％M-Ligand-ETM10nm/Mg:Ag/Ag；
first electrode layer 02 (anode ITO), hole injection layer 04(HATCN), hole transport layer 05(NPB), and light-emitting layer 06 (Alq)3) A hole blocking layer 07(Bphen), an electron transport layer 08 (x% M-Ligand-ETM), and a second electrode layer 03 (cathode Mg: Ag/Ag).
The host material of the electron transport layer in this example has a structure (R is all H) as shown in (b) below:
the selection of the host material, the doped inert metal, and the ligand compound of the electron transport layer in this embodiment, and the composition ratio x% and the doping ratio of the dopant are shown in table 2 below, respectively, and the existing active metal doping is used as a comparison device.
TABLE 2 selection of device materials
| Device numbering | M | Ligand | M：Ligand | ETM | The mixing ratio is |
| 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％ |
| Comparison device 3 | Ag | Is free of | - | ETM(b) | 10％ |
| Comparison device 4 | Cs | ETM(b) | 10％ |
It can be seen that the performance of the devices doped with the dopants of the present invention is superior to the performance of the prior art control devices.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (6)
1. An n-type dopant based on an inert metal, characterized by comprising an inert metal and a ligand compound having a coordination function; the mass ratio of the inert metal to the ligand compound with the coordination function is 1-50: 100, respectively;
the inert metal is a metal which is stable in air and has a work function higher than 4.0 eV;
the inert metal is one or a mixture of several of 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), gold (Au), platinum (Pt) and mercury (Hg);
the ligand compound having a coordinating function has a structure represented by the following formula (L1) -formula (L16):
2. use of an n-type dopant according to claim 1 for the preparation of a doping material for the electron transport layer of an organic electroluminescent device.
3. An organic electroluminescent device comprising a substrate (01), and a light-emitting device formed on the substrate in this order, the light-emitting device comprising a first electrode layer (02), a light-emitting layer (06), an electron transport layer (08), and a second electrode layer (03); it is characterized in that the preparation method is characterized in that,
the electron transport layer (08) comprises an electron transport host material and the n-type dopant of claim 1 doped in the electron transport host material.
4. The organic electroluminescent device according to claim 3, wherein the doping ratio of the n-type dopant in the electron transport layer is 1vol% to 99 vol%.
5. The organic electroluminescent device according to claim 4, wherein the doping ratio of the n-type dopant in the electron transport layer is 5vol% to 30 vol%.
6. The organic electroluminescent device according to any of claims 3 to 5, characterized in that the device further comprises a hole injection layer (04) and/or a hole transport layer (05) arranged between the first electrode layer (02) and the light-emitting layer (06), and a hole blocking layer (07) between the light-emitting layer (06) and the electron transport layer (08).
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| CN103594659A (en) * | 2012-08-17 | 2014-02-19 | 海洋王照明科技股份有限公司 | Organic electroluminescent device and preparation method thereof |
| CN107464885A (en) * | 2016-06-06 | 2017-12-12 | 清华大学 | A kind of organic electroluminescence device |
| CN107464884A (en) * | 2016-06-06 | 2017-12-12 | 清华大学 | A kind of laminated organic electroluminescent device |
| CN108269936A (en) * | 2016-12-30 | 2018-07-10 | 昆山国显光电有限公司 | A kind of electrode and its preparation method and application |
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| CN103594659A (en) * | 2012-08-17 | 2014-02-19 | 海洋王照明科技股份有限公司 | Organic electroluminescent device and preparation method thereof |
| CN107464885A (en) * | 2016-06-06 | 2017-12-12 | 清华大学 | A kind of organic electroluminescence device |
| CN107464884A (en) * | 2016-06-06 | 2017-12-12 | 清华大学 | A kind of laminated organic electroluminescent device |
| CN108269936A (en) * | 2016-12-30 | 2018-07-10 | 昆山国显光电有限公司 | A kind of electrode and its preparation method and application |
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