CN109524571B - Method for realizing N-type doping of electron transport material based on inert metal and application thereof - Google Patents

Method for realizing N-type doping of electron transport material based on inert metal and application thereof Download PDF

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CN109524571B
CN109524571B CN201811142500.3A CN201811142500A CN109524571B CN 109524571 B CN109524571 B CN 109524571B CN 201811142500 A CN201811142500 A CN 201811142500A CN 109524571 B CN109524571 B CN 109524571B
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段炼
宾正杨
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Tsinghua University
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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Abstract

The present invention belongs to the field of organic electroluminescent device technologyThe field, in particular to a method for realizing N-type doping of an electron transport material based on inert metal, and further discloses application of the method in preparing an organic electroluminescent device. The method for realizing N-type doping of the electron transport material based on the inert metal utilizes the ligand compound with the coordination function to be connected with the existing general electron transport material, so that groups with coordination performance are added to the general electron transport material, the general electron transport material has the coordination function, and the coordination function of the general electron transport material and M can be utilizedn+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.

Description

Method for realizing N-type doping of electron transport material based on inert metal and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent devices, and particularly relates to a method for realizing N-type doping of an electron transport material based on inert metal, and further discloses application of the method in preparation of 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 present invention is to provide a method for realizing N-type doping of an electron transport material based on an inert metal, wherein a ligand compound with coordination ability is adopted to perform a reaction connection with an existing electron transport material, and a group with coordination ability is added to the existing electron transport material, so that the electron transport material can perform a coordination reaction with the inert metal, and the inert metal is promoted to lose electrons, thereby reducing the work function of the inert metal, enabling the inert metal to also realize an N-type doping effect similar to that of an active metal, so as to reduce the LUMO energy level of the electron transport material, further reduce the injection barrier of electrons, thereby significantly reducing the driving voltage of a device, and improving the efficiency of the device.
The invention further discloses application of the method in preparing an organic electroluminescent device.
In order to solve the technical problems, the method for realizing N-type doping of the electron transport material based on the inert metal comprises the step of connecting a ligand with coordination performance and a group with electron transport performance through a chemical bond to obtain the electron transport material with strong coordination performance, wherein the electron transport material can realize N-type doping based on the transition metal.
The ligand having a coordinating function has a structure represented by the following formula (L1) -formula (L15):
Figure GDA0001962532950000031
the group with the electron transport property is chemically connected with any group of the ligand with the coordination property.
The invention also discloses application of the method for realizing N-type doping of the electron transport material based on the inert metal in preparation 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 comprises the electron transport host material obtained by the method and inert metal doped in the electron transport host material.
In the electron transport layer, the doping proportion of the inert metal is 1vol% -99 vol%.
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 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 invention also discloses a method for preparing the organic electroluminescent device, and the preparation of the electron transport layer comprises the step of obtaining the electron transport main body material with coordination performance according to the method and the step of adding the inert metal as a doping material.
The method for realizing N-type doping of the electron transport material based on the inert metal utilizes the ligand with coordination performance to be connected with the group with the electron transport performance in the prior art through a chemical bond, so that a plurality of groups with coordination performance are added to the general electron transport material, the general electron transport material further has the coordination function, and the coordination function of the general electron transport material and Mn + can be utilized to generate the coordination function to promote the inert metal M to lose electrons so as to reduce the work function of the inert metal M, so that the inert metal realizes the N-type doping effect similar to that of active alkali metal, the transmission characteristic of the electron transport material is effectively improved, the injection barrier of electrons is reduced, and the injection of electrons is enhanced. Through the action mechanism, a general material only having an electron transmission performance can realize the N-type doping effect based on the inert metal, an N-type doping effect similar to that of the active metal is obtained, the application range of the N-type doping based on the inert metal is expanded, the N-type doping method is a new N-type doping idea, the use of the active alkali metal can be avoided, the OLED device which is cheap, stable and efficient is prepared, and the application range of the N-type doping based on the inert metal is further expanded.
The material adopted by the invention is transition 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. The electron transport material subjected to coordination modification is doped with inert metal, so that 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, the 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.
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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 performance test results of the device of example 3 of the present invention;
FIG. 3 is the results of performance testing of the device prepared in example 3;
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 comprises an electron transport host material having coordination properties obtained by chemically bonding a known conventional electron transport material with a ligand compound having a coordination function, and an inert metal doped in the electron transport host material; the doping proportion of the inert metal is 1vol% -99vol%, preferably 5 vol% -30 vol%.
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 having a coordinating function has a structure represented by the following formula (L1) -formula (L15):
Figure GDA0001962532950000061
the electron transport material may be chemically bonded to any group of the ligand compound, and the bonding method may be a feasible method known in the art, and specifically may include an organic synthesis method, such as carbon-carbon bond coupling.
The preparation process of the organic electroluminescent device is the same as that of the prior art, wherein the preparation step of the electron transport layer 08 is the conventional vacuum co-evaporation and other steps.
The evaporation rate of the metal is controlled to be lower and 0.1 angstrom/second, and at the rate, the contact between the compound with coordination performance of the main body material and the doping material of the electron transport layer and the inert metal is more sufficient, so that the inert metal M is more uniformly dispersed in the electron transport main body material, and the compound is favorable for compounding.
Example 1
In the embodiment, the ETM1-ETM7 electron transport material shown in the following structure is connected by adopting the ligand with coordination performance shown in a formula (L6), and the electron transport main body material ETM 1-Phen-ETM 7-Phen with coordination performance is prepared.
The specific preparation method of ETM1-Phen comprises the following steps:
Figure GDA0001962532950000071
taking 5.0g of 4, 7-dibromonorphin, 6.2g of 1-naphthalene boric acid, 6.1g of potassium carbonate and 1.29g of tetrakis (triphenylphosphine) palladium (0) in a 500ml round-bottom flask, adding 100ml of toluene, 50ml of water and 50ml of ethanol, stirring, introducing nitrogen, heating to 90 ℃, reacting for 48 hours, cooling to terminate the reaction, separating, extracting the organic phase with dichloromethane, performing rotary evaporation on the organic phase, dissolving with dichloromethane/a small amount of methanol solution, and sublimating in a partition manner to obtain the product.
The specific preparation method of ETM2-Phen comprises the following steps:
Figure GDA0001962532950000072
(ii) a The specific preparation method of ETM3-Phen comprises the following steps:
Figure GDA0001962532950000081
the specific preparation method of ETM4-Phen comprises the following steps:
Figure GDA0001962532950000082
the specific preparation method of ETM5-Phen comprises the following steps:
Figure GDA0001962532950000083
the specific preparation method of ETM6-Phen comprises the following steps:
Figure GDA0001962532950000084
the specific preparation method of ETM7-Phen comprises the following steps:
Figure GDA0001962532950000085
example 2
Structure of single-electron device:
ITO/Bphen(100nm)/ETM1-Phen(5-30％w.t.％，5-100nm)/Al；
first electrode layer 02 (anode ITO)/hole blocking layer 07 (Bphen)/electron transport layer 08 (x% ETM 1-Phen-ETM 7-Phen)/second electrode layer 03 (cathode Al);
the host material of the electron transport layer in this embodiment is ETM1-Phen, and the doped inert metal is Ag.
As shown in FIG. 2, device 1 is a curve corresponding to ETM/Al;
the device 2 is a curve corresponding to ETM 1-Phen/Al;
the device 3 is a curve corresponding to ETM 2-Phen/Al;
the device 4 is a curve corresponding to ETM 3-Phen/Al;
the device 5 is a curve corresponding to ETM 4-Phen/Al;
the device 6 is a curve corresponding to ETM 5-Phen/Al;
the device 7 is a curve corresponding to ETM 6-Phen/Al;
the device 8 is a curve corresponding to ETM 7-Phen/Al;
the cathodes of devices 1-2 were all Al, wherein:
device 1 electron transport layer 08 is shown as an electron transport material ETM (i.e., not doped with an inert metal);
the electron transport layer 08 (20% ETM1-Phen) in the device 2 adopts an electron transport material of ETM1-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, the electron transport host material ETM1-Phen with 100 angstroms is doped with inert metal Ag with 20 angstroms.
The electron transport layer 08 (20% ETM2-Phen) in the device 3 adopts an electron transport material of ETM2-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, 20 angstroms of inert metal Ag is doped in 100 angstroms of electron transport host material ETM 2-Phen;
the electron transport layer 08 (20% ETM3-Phen) in the device 4 adopts an electron transport material of ETM3-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, 20 angstroms of inert metal Ag is doped in 100 angstroms of electron transport host material ETM 3-Phen;
the electron transport layer 08 (20% ETM4-Phen) in the device 5 adopts an electron transport material of ETM4-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, 20 angstroms of inert metal Ag is doped in 100 angstroms of electron transport host material ETM 4-Phen;
the electron transport layer 08 (20% ETM5-Phen) in the device 6 adopts an electron transport material of ETM5-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, 20 angstroms of inert metal Ag is doped in 100 angstroms of electron transport host material ETM 5-Phen;
the electron transport layer 08 (20% ETM6-Phen) in the device 7 adopts an electron transport material of ETM6-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, 20 angstroms of inert metal Ag is doped in 100 angstroms of electron transport host material ETM 6-Phen;
the electron transport layer 08 (20% ETM7-Phen) in the device 8 adopts an electron transport material of ETM7-Phen doped with inert metal Ag, and the doping proportion is 20 vol%, namely, the electron transport host material ETM7-Phen with 100 angstroms is doped with inert metal Ag with 20 angstroms.
The current density-voltage curve diagram of the devices 1-8 is shown in fig. 2, and it can be seen from fig. 2 that the method of the present invention can realize N-type doping of inert metal of conventional ETM host material, and can realize efficient electron injection of electron transport layer.
Example 3
The device structure is as follows:
ITO/HAT-CN(10nm)/NPB(30nm)/Alq3(30nm)/Bphen(20nm)/x％M-ETM-Ligand 10nm/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-ETM-Ligand), and a second electrode layer 03 (cathode Ag).
The main material ETM-Ligand of the electron transport layer, the doped inert metal M and the doping ratio in this embodiment are shown in table 1 below, and the existing active metal doping is used as a comparison device.
TABLE 1 selection of device materials
Figure GDA0001962532950000101
Figure GDA0001962532950000111
The performance of the device is tested, the test result is shown in figure 3, and the result shows that the performance of the device prepared by the electron transport main body material with coordination performance is superior to that of the conventional electron transport material device in the prior art.
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 (7)

1. 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 obtained by a method of realizing N-type doping of an electron transport material based on an inert metal and the inert metal doped in the electron transport host material;
the method for realizing N-type doping of the electron transport material based on the inert metal comprises the steps of connecting a ligand with coordination performance and a group with electron transport performance through a chemical bond to obtain the electron transport material with strong coordination performance, wherein the electron transport material can realize N-type doping based on transition metal; the ligand having a coordination function has a structure represented by the following formula (L1) -formula (L4), (L7) -formula (L15):
Figure DEST_PATH_IMAGE001
the group with the electron transport property is chemically connected with any group of the ligand with the coordination property.
2. The organic electroluminescent device according to claim 1, wherein the doping ratio of the inert metal in the electron transport layer (08) is 1vol% to 99 vol%.
3. An organic electroluminescent device according to claim 1 or 2, characterized in that the inert metal is a metal which is stable in air and has a work function higher than 4.0 eV.
4. The organic electroluminescent device according to claim 3, wherein the inert metal is one or a mixture 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).
5. The organic electroluminescent device according to claim 4, wherein the inert metal is a metal atom with a strong coordination ability, and comprises one or a mixture of cobalt (Co), nickel (Ni), copper (Cu), ruthenium (Ru), silver (Ag), iridium (Ir), gold (Au) or platinum (Pt).
6. The organic electroluminescent device according to claim 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) arranged between the light-emitting layer (06) and the electron transport layer (08).
7. A method of manufacturing an organic electroluminescent device according to any one of claims 1 to 6, characterized in that the preparation of the electron transport layer (08) comprises a step of obtaining an electron transport host material with coordinating properties according to the method of claim 1 or 2, and a step of adding the inert metal as a dopant material.
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