CN111180599B - Mixture, organic electroluminescent device containing mixture and application of mixture - Google Patents
Mixture, organic electroluminescent device containing mixture and application of mixture Download PDFInfo
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Abstract
The invention provides a mixture, an organic electroluminescent device containing the same and application thereof, wherein the mixture comprises a free radical and a triarylamine compound; wherein the free radical is selected from TEMPO derivative free radicals. The mixture provided by the invention is used as a hole injection layer of an electroluminescent device, so that the luminous efficiency of the device is improved, and the service life of the device is prolonged.
Description
Technical Field
The invention belongs to the technical field of electroluminescence, and relates to a mixture, an organic electroluminescent device containing the mixture and application of the organic electroluminescent device.
Background
In recent years, OLED display and lighting have been increasingly known. It has been applied in the fields of television and vehicle. HIS forecasts that the market size of OLED displays for automobiles worldwide has increased 114 times in 2018-2022, and by 2022 the market size of OLED on-board displays will increase to $ 3.43 billion. The structure and the functional layer of the OLED have great influence on the performance of the OLED. A typical OLED includes an anode, a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, EML, ETL are thin films formed of organic and/or organometallic compounds. The roughness of the ITO (indium tin oxide conductive glass) substrate surface directly affects the light emitting efficiency of the device, resulting in reduced driving life, short circuit of the device, etc. Usually, a hole injection layer is added between the ITO glass and the hole transport layer to overcome the energy barrier of the interface, so that the service life of the device is prolonged.
CN102292839A discloses an OLED stability and organic light emitting device improved by a doped hole transport layer, the device comprising an anode and a cathode, a first organic layer located between the anode and the cathode, the first organic layer being a light emitting layer comprising a first organic light emitting material, the device further comprising a second organic layer located between the anode and the first organic layer, the second organic layer being a non-light emitting layer, the second organic layer comprising an organic small molecule hole transport material having a concentration of 50 to 99wt%, and an organic small molecule electron transport material having a concentration of 0.1 to 5wt%, which gives an OLED device having a higher stability but a lower light emitting efficiency.
The lifetime of organic electroluminescent devices still needs to be improved, and the lifetime is very important for commercial applications. Therefore, it is required to develop an organic light emitting device that can improve the lifetime of the device and has higher light emitting efficiency.
Disclosure of Invention
The invention aims to provide a mixture, an organic electroluminescent device containing the mixture and application of the mixture. The mixture provided by the invention is used as a hole injection layer of an electroluminescent device, so that the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a mixture comprising free radicals and a triarylamine compound;
wherein the free radical is selected from TEMPO derivative free radicals.
In the invention, the free radical can obtain electrons from the arylamine compound to form radical anions, the triarylamine compound loses electrons to form arylamine cations, the hole concentration is improved, the hole transmission speed is accelerated, and meanwhile, the arylamine compound is pre-oxidized by the free radical to obtain stable arylamine cations, so that the service life of an organic electroluminescent device applying the mixture provided by the invention can be prolonged.
In the present invention, the difference between the reduction potential of the radical and the oxidation potential of the triarylamine-based compound is 0.05 to 0.35V, for example, 0.10V, 0.15V, 0.20V, 0.25V, 0.30V, and more preferably 0.1 to 0.3V.
In the present invention, the reduction potential of the radical is-0.2 to 1.2V, for example, -0.1V, 0V, 0.2V, 0.4V, 0.5V, 0.6V, 0.8V, 1.0V, etc., preferably-0.2 to 0.8V.
In the present inventionThe oxidation and reduction potentials are relative to Fc/Fc in tetrahydrofuran + And (4) measuring.
In the present invention, the molar ratio of the radical to the triarylamine-based compound is (0.01-0.3): 1, for example, 0.02.
The molar ratio of the free radical to the triarylamine compound is within the limited range of the invention, so that the finally obtained organic electroluminescent device has better current efficiency and longer service life, and if the content of the free radical is too high or too low, the current efficiency can be reduced, and the service life of the device can be reduced.
In the present invention, the free radical is selected from:
any one or a combination of at least two of them.
Preferably, the triarylamine compound is selected from:
In a second aspect, the present invention provides a use of a mixture according to the first aspect in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially disposed.
Wherein the composition of the hole injection layer comprises the mixture of the first aspect.
Preferably, the organic electroluminescent device is top-emitting or bottom-emitting.
Preferably, the constituent material of the light emitting layer includes any one of a red light emitting material, a blue light emitting material, or a green light emitting material, or a combination of at least two thereof.
Preferably, the organic electroluminescent device further comprises an electron blocking layer, wherein the electron blocking layer is positioned between the hole transport layer and the light emitting layer.
Preferably, the organic electroluminescent device further comprises a hole blocking layer, wherein the hole blocking layer is positioned between the electron transport layer and the light emitting layer.
Preferably, the hole injection layer has a thickness of 1-20nm, such as 3nm, 5nm, 8nm, 10nm, 12nm, 15nm, 18nm, etc., preferably 5-15nm.
Preferably, the hole transport layer has a thickness of 100-200nm, such as 110nm, 120nm, 130nm, 140nm, 150nm, 180nm, etc., preferably 100-150nm.
Preferably, the thickness of the light-emitting layer is 10-100nm, such as 20nm, 30nm, 40nm, 50nm, 60nm, 70nm, 80nm, 90nm, etc., preferably 20-80nm.
Preferably, the thickness of the electron transport layer is 10-50nm, such as 20nm, 30nm, 40nm, and the like.
Preferably, the thickness of the electron injection layer is 0.5-5nm, such as 1nm, 2nm, 3nm, 4nm, etc., preferably 0.5-2nm.
Preferably, the organic electroluminescent device is structured as a top-emitting, cathode having a thickness of 10-20nm, such as 12nm, 14nm, 15nm, 16nm, 18nm, etc.
Preferably, the organic electroluminescent device is structured as a top-emitting, cathode having a thickness of 75-85nm, such as 78nm, 80nm, 82nm, etc.
Preferably, the electron blocking layer has a thickness of 50-100nm, such as 60nm, 70nm, 80nm, 90nm, etc., preferably 50-80nm.
Preferably, the hole blocking layer has a thickness of 1 to 20nm, such as 2nm, 4nm, 5nm, 8nm, 10nm, 12nm, 14nm, 18nm, etc., preferably 1 to 10nm.
In the invention, the anode can be selected from low work function substances, can be a transparent or reflective electrode, can be ITO, IZO, snO2 and ZnO, and can also be Mg, al, mg-Ag, au and the like.
Free radicals may be selected from materials disclosed in j.org.chem.2012,77,1789-1797, j.am.chem.soc.2012,134,4537-4540, phys.chem.chem.phys.,2010,12,5841-5845, without passing through 5841.
Preferably, the material of the HOLE TRANSPORT layer is referred to EP2628778B1 (HOLE TRANSPORT MATERIALS HAVING A SULFUR-CONTAINING GROUP).
Preferably, common electron barrier materials such as TCTA:
preferably, the light emitting layer may be selected from a phosphorescent light emitting material or a fluorescent light emitting material, and may be composed of a host-guest material, and the mass ratio of the host to the guest is 1.
The host material may be Alq3, 4' -N, N ' -dicarbazole-biphenyl (4, 4' -N, N ' -dicarbazole-biphenyl, CBP), poly (N-vinylcarbazole) (PVK), 9,10-di (naphthalene-2-yl) Anthracene (AND), 4' -tris (carbazol-9-yl) triphenylamine (TCTA), 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (TPBI), 3-tert-butyl-9, 10-di-phenylxanthene (TBADN), tyrylene (DSA), bis (2- (2-hydroxyphenyl) benzothiazoliate) zinc (2- (2-hydroxyphenyl) benzene (Zn, BTZ) 2 )。
Wherein AND is
TPBI of
TBADN is
The guest material may be a phosphorescent or fluorescent light emitting material:
phosphorescent red guest materials such as PtOEP, ir (piq) 3 、Btp 2 Ir(acac)：
The phosphorescent green guest material has Ir (ppy) 3 、Ir(ppy) 2 (acac)、Ir(mpyp) 3 ：
The green fluorescent guest material is G-1:
the blue phosphorescent guest material is F 2 Irpic、(F 2 ppy) 2 Ir(tmd)、Ir(dfppz) 3 ：
Fluorescent blue guest material B-1:
the hole blocking layer has good hole blocking capability and comprises oxazole derivatives, triazole derivatives and phenanthroline derivatives.
The electron transport layer material is selected from aryl, heteroaryl, alkyl substituted phosphorus oxide compound, or 1, 10-phenanthroline derivative; or the above compound is added with lithium halide or lithium organic compound, the mass ratio is 10-70wt%, preferably 20-60wt%, and more preferably 40-60wt%.
Common phosphorus oxygen compounds:
commonly used 1, 10-phenanthroline derivatives:
the lithium organic compound is commonly used:
preferably, the material of the electron injection layer is selected from KF, liF, naCl, li 2 O, mg, etc., or consist of a lithium halide or an organic compound of lithium.
The cathode is selected from metals, alloys or conductive compounds, such as Mg: ag, al, li, mg, al: li, mg: in, and the like.
A commonly used CPL (light extraction layer material) is N, N, N ', N' -tetra-biphenylyl-biphenyl diamine
N4, N4 '-bis ([ 1,1' -biphenyl)]-4-yl) -N4, N4 '-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]-4,4' -diamine
And the like.
In a fourth aspect, the present invention provides the use of an organic electroluminescent device according to the fourth aspect in a display device or a lighting device.
Compared with the prior art, the invention has the following beneficial effects:
(1) In the invention, the free radical can obtain electrons from the arylamine compound to form radical anions, the triarylamine compound loses electrons to form arylamine cations, the hole concentration is improved, the hole transmission speed is accelerated, and meanwhile, the arylamine compound is pre-oxidized by the free radical to obtain stable arylamine cations, so that the service life of an organic electroluminescent device applying the mixture provided by the invention can be prolonged;
(2) The OLED device prepared by the mixture provided by the invention has higher current efficiency and longer service life, wherein the current efficiency is more than 6.18cd/A, the service life of a blue fluorescence light-emitting device is more than 24h, and the service life of a phosphorescence red light-emitting device is more than 63 h.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device provided in embodiment 1 of the present invention;
wherein, 1-anode; 2-a hole injection layer; 3-a hole transport layer; 4-a light-emitting layer; 5-an electron transport layer; 6-electron injection layer; 7-a cathode; 8-substrate.
FIG. 2 is a schematic structural view of an organic electroluminescent device provided in example 17 of the present invention;
among them, 9-hole blocking layer; 10-electron blocking layer.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitation of the present invention.
Example 1
A top-emission and phosphorescence red light emitting device, as shown in figure 1, comprises an anode 1, a hole injection layer 2 (10 nm), a hole transport layer 3 (150 nm), an organic light emitting layer 4 (40 nm), an electron transport layer 5 (30 nm), an electron injection layer 6 (1 nm) and a cathode 7 in sequence from bottom to top on a substrate 8.
Wherein, the anode material is ITO (ITO/Ag/ITO); hole injection layerThe material is Z-1; the hole transport layer material is J-13; the organic light-emitting layer material is selected from 5wt% Ir (piq) 3 CBP; the electron transport layer material is selected from BPhen: liQ =1 (mass ratio); the material of the electron injection layer is LiQ; the cathode material is Mg: ag =9 (mass ratio), and a CPL (light extraction material, N, N, N ', N' -tetra-biphenyl diamine is selected) layer is evaporated on the cathode material.
The preparation method comprises the following steps:
(1) Substrate cleaning: carrying out ultrasonic treatment on the ITO (ITO/Ag/ITO) coated electrode substrate in an aqueous cleaning agent (the components and concentration of the aqueous cleaning agent are that glycol solvent is less than or equal to 10wt percent and triethanolamine is less than or equal to 1wt percent), washing in deionized water, and carrying out ultrasonic treatment in a water-based solvent system under the conditions of acetone: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1.
(2) Vapor deposition organic light emitting device
Placing the glass substrate with anode layer in vacuum chamber, and vacuumizing to 1 × 10 -6 To 2X 10 -4 Pa, evaporating a hole injection layer in two evaporation sources in a co-evaporation mode, wherein the total evaporation thickness is 10nm;
evaporating a hole transport layer on the hole injection layer at the evaporation rate of 0.1nm/s and the evaporation film thickness of 150nm;
a luminescent layer is evaporated on the hole transport layer in a vacuum evaporation mode, and the total film thickness of the evaporation layer is 40nm;
vacuum evaporating an electron transport layer on the luminescent layer in a co-evaporation mode, wherein the BPhen evaporation rate is 0.05nm/s, the LiQ evaporation rate is 0.05nm/s, and the total evaporation film thickness is 30nm;
a LiQ layer is vacuum evaporated on the electron transport layer and is an electron injection layer of the device, the evaporation rate is 0.05nm/s, and the total film thickness of evaporation is 1nm;
and (3) evaporating Mg and Ag on the electron injection layer to be used as a cathode layer of the device, performing vacuum evaporation in a co-evaporation mode, wherein the evaporation rate of Mg is 0.09nm/s, the evaporation rate of Ag is 0.01nm/s, the total film thickness of evaporation is 15nm, and then evaporating a CPL (80 nm) layer on the electron injection layer to obtain the OLED device.
Examples 2 to 4
The difference from example 1 is that the molar ratio of the hole injection layer material Z-1.
Example 5
The difference from example 2 is that the hole injection layer material is Z-1 j-16=0.03 (molar ratio).
Example 6
The difference from example 2 is that the hole injection layer material was Z-1 j-21=0.03 (molar ratio).
Example 7
The difference from example 2 is that the hole injection layer material is Z-1 j-22=0.03 (molar ratio).
Example 8
The difference from example 2 is that the hole injection layer material is Z-2 j-13=0.03 (molar ratio).
Example 9
The difference from example 2 is that the hole injection layer material is Z-3 j-13=0.03 (molar ratio).
Example 10
The difference from example 2 is that the hole injection layer material is Z-5 j-13=0.03 (molar ratio).
Example 11
The difference from example 2 is that the hole injection layer material is Z-6 j-13=0.03 (molar ratio).
Example 12
The difference from example 2 is that the hole injection layer material is Z-7 j-13=0.03 (molar ratio).
Example 13
The difference from example 2 is that, in this example, as shown in fig. 2, a hole blocking layer 9 (HB-1, 5 nm) is provided between the electron transport layer 5 and the light emitting layer 4, and an electron blocking layer 10 (TCTA, 60 nm) is provided between the hole transport layer 3 and the light emitting layer 4.
The preparation method comprises the following steps:
(1) Substrate cleaning: reference is made to example 1.
(2) Preparation of organic light emitting device
With anode layerPlacing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -6 To 2X 10 -4 Pa, evaporating a hole injection layer in two evaporation sources in a co-evaporation mode, wherein the total evaporation thickness is 10nm;
evaporating a hole transport layer (consisting of J-13) on the hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 150nm;
evaporating an electron blocking layer (composed of TCTA) between the hole transport layers at the evaporation rate of 0.1nm/s and the evaporation film thickness of 60nm;
vacuum evaporating a luminescent layer on the electron barrier layer in a co-evaporation mode, wherein the total film thickness of the evaporation layer is 40nm;
evaporating a hole blocking layer on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 5nm;
a layer of electron transport layer is evaporated on the hole blocking layer in a vacuum evaporation mode, the BPhen evaporation rate is 0.05nm/s, the LiQ evaporation rate is 0.05nm/s, and the total evaporation film thickness is 30nm;
a LiQ layer is vacuum evaporated on the electron transport layer and is an electron injection layer of the device, the evaporation rate is 0.05nm/s, and the total film thickness of evaporation is 1nm;
mg and Ag are evaporated on the electron injection layer to be used as a cathode layer of the device, and the device is subjected to vacuum evaporation in a co-evaporation mode, wherein the evaporation rate of Mg is 0.09nm/s, the evaporation rate of Ag is 0.01nm/s, the total film thickness of evaporation is 15nm, and CPL (the thickness is 80 nm) is evaporated on the electron injection layer.
Example 14
A bottom-emission and phosphorescence red light emitting device comprises an anode, a hole injection layer (10 nm), a hole transport layer (150 nm), an organic light emitting layer (40 nm), an electron transport layer (30 nm), an electron injection layer (1 nm) and a cathode (80 nm) from bottom to top on a substrate.
Wherein, the anode material is ITO; the hole injection layer material is Z-1; the hole transport layer material is J-13; the organic light-emitting layer material was selected from 5wt% Ir (piq) 3 CBP; the electron transport layer material is BPhen; the material of the electron injection layer is LiF; the cathode material is Al.
The preparation process is referred to example 1.
Example 15
A bottom-emitting and blue-light fluorescent light-emitting device comprises an anode, a hole injection layer (10 nm), a hole transport layer (150 nm), an organic light-emitting layer (40 nm), an electron transport layer (30 nm), an electron injection layer (1 nm) and a cathode (80 nm) from bottom to top on a substrate in sequence.
Wherein, the anode material is ITO; the hole injection layer material is Z-1; the hole transport layer material is J-13; the organic luminescent layer material is B-1; the electron transport layer material is BPhen; the material of the electron injection layer is LiF; the cathode material is Al.
The preparation process is referred to example 1.
Comparative example 1
The difference from example 2 is that the hole injection layer material in this comparative example is NDP-9 j-13=0.03 (mass ratio).
Comparative example 2
The difference from example 1 is that the hole injection layer material in this comparative example is Z-1.
Comparative example 3
The difference from example 1 is that the hole injection layer material in this comparative example is J-13.
Performance testing
The organic light emitting devices provided in examples 1 to 15 and comparative examples 1 to 3 were subjected to performance tests as follows:
the characteristics of the device such as current, voltage, brightness, service life and the like are synchronously tested by adopting a PR 650 spectrum scanning luminance meter and a KeithleyK 2400 digital source meter system;
and (3) testing conditions are as follows: the current density is 10mA/cm 2 Room temperature.
The test results are shown in table 1:
TABLE 1
According to the embodiment and the performance test, the organic electroluminescent device provided by the invention has higher current efficiency and longer service life.
As is clear from the comparison between example 1 and examples 2 to 4, the molar ratio of the radical to the triarylamine compound in the present invention is preferably in the range of 0.01 to 0.3, and when the molar ratio of the radical to the triarylamine compound is in the range of 0.02 to 0.08, the current efficiency is 6.19cd/A or more, and the service life is 78 hours or more. As is clear from comparison between example 1 and example 13, when the electron blocking layer and the hole blocking layer are increased, the current efficiency and the lifetime can be greatly improved. As is clear from the comparison of example 1 and comparative example 1, the advantageous effects of the present invention are not achieved unless the mixture of the present invention is selected. As can be seen from the comparison of example 1 and comparative examples 2 to 3, the hole injection layer of the present invention is a mixture of a radical and a triarylamine compound, and neither of them is sufficient.
The applicant states that the mixture, the organic electroluminescent device comprising the mixture and the application of the mixture are illustrated by the above embodiments, but the invention is not limited to the above process steps, i.e. the invention does not depend on the above process steps to be implemented. It will be apparent to those skilled in the art that any modifications to the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific forms, etc., are within the scope and disclosure of the present invention.
Claims (16)
1. A mixture comprising a free radical and a triarylamine compound;
wherein the free radical is selected from TEMPO derivative free radicals;
the free radical is selected from:
2. The mixture according to claim 1, wherein the difference between the reduction potential of the free radical and the oxidation potential of the triarylamine compound is 0.05-0.35V.
3. The mixture according to claim 2, wherein the difference between the reduction potential of the free radicals and the oxidation potential of the triarylamine compound is 0.1-0.3V.
4. The mixture according to claim 1 or 2, wherein the radical has a reduction potential of-0.2 to 1.2V.
5. The mixture according to claim 4, wherein the radical has a reduction potential of-0.2 to 0.8V.
6. The mixture according to any one of claims 1 to 3, wherein the molar ratio of the free radicals to the triarylamine compound is (0.01-0.3): 1.
7. The mixture according to claim 6, wherein the molar ratio of the free radicals to the triarylamine compound is (0.01-0.1): 1.
8. The mixture according to claim 7, wherein the molar ratio of the free radicals to the triarylamine compound is (0.02-0.08): 1.
9. The mixture according to claim 1, wherein the triarylamine compound is selected from the group consisting of:
10. Use of a mixture according to any of claims 1 to 9 in an organic electroluminescent device.
11. An organic electroluminescent device is characterized by comprising an anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode which are sequentially arranged;
wherein the composition of the hole injection layer comprises the mixture of any one of claims 1 to 9.
12. The organic electroluminescent device according to claim 11, wherein the organic electroluminescent device is top-emitting or bottom-emitting.
13. The organic electroluminescent device as claimed in claim 11, wherein the constituent material of the light-emitting layer comprises any one of a red light-emitting material, a blue light-emitting material or a green light-emitting material or a combination of at least two of them.
14. The organic electroluminescent device of claim 11, further comprising an electron blocking layer between the hole transport layer and the light emitting layer.
15. The organic electroluminescent device of claim 11, further comprising a hole blocking layer between the electron transport layer and the light emitting layer.
16. Use of an organic electroluminescent device according to any of claims 11 to 15 in a display device or a lighting device.
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