CN110498790B - Organic light-emitting composite material and organic electroluminescent device containing same - Google Patents

Organic light-emitting composite material and organic electroluminescent device containing same Download PDF

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CN110498790B
CN110498790B CN201810469420.2A CN201810469420A CN110498790B CN 110498790 B CN110498790 B CN 110498790B CN 201810469420 A CN201810469420 A CN 201810469420A CN 110498790 B CN110498790 B CN 110498790B
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organic compound
organic
compound
organic light
emitting composite
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CN110498790A (en
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李崇
赵鑫栋
张兆超
叶中华
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Jiangsu Sunera Technology Co Ltd
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Abstract

The present invention relates to an organic light-emitting composite material comprising a host material comprising at least one first organic compound and at least one second organic compound and a guest material which is a phosphorescent compound or a fluorescent compound, characterized in that the difference between the singlet level and the triplet level of the first organic compound is not more than 0.2eV, preferably not more than 0.15eV, more preferably not more than 0.1 eV; the difference between the singlet level and the triplet level of the second organic compound is not less than 0.1eV, preferably not less than 0.2eV, and more preferably not less than 0.3 eV. The material can be used as a luminescent layer to improve the efficiency and the service life of an organic electroluminescent device. The invention also relates to a high-efficiency long-life organic electroluminescent device and a lighting or display element containing the organic luminescent composite material.

Description

Organic light-emitting composite material and organic electroluminescent device containing same
Technical Field
The present invention relates to an organic light emitting composite material. Specifically, the present invention relates to an organic light emitting composite material comprising at least one first organic compound and at least one second organic compound as host materials and a phosphorescent compound or a fluorescent compound as guest materials. The invention also relates to a high-efficiency long-life organic electroluminescent device and a lighting or display element containing the organic luminescent composite material.
Background
In recent years, organic electroluminescent devices have become hot spots for research and development. The organic electroluminescent device is considered to have a great application potential in the field of next-generation flat panel display because of being capable of realizing ultra-thin and ultra-light weight, having a fast response speed to an input signal and realizing low-voltage direct current driving, and has received wide attention in recent years.
The basic structure of an organic electroluminescent device comprises opposing cathode and anode electrodes and a light-emitting layer sandwiched between the cathode and anode electrodes. Organic electroluminescent devices are based on the following light-emitting mechanism: when a voltage is applied between two electrodes sandwiching a light-emitting layer, holes from an anode and electrons from a cathode are recombined in the light-emitting layer to form excitons, and the excitons relax to a ground state to release energy to form photons.
In an organic electroluminescent device, a light-emitting layer generally requires a host material doped with a guest material to obtain higher energy transfer efficiency and fully exert the light-emitting potential of the guest material. In order to obtain higher host-guest energy transfer efficiency, the combination of host-guest materials and the balance degree of electrons and holes in the host materials are key factors for obtaining high-efficiency devices. The carrier mobility of electrons and holes in the existing main body material often has large difference, so that an exciton recombination region deviates from a light-emitting layer, the carrier balance degree in the device is influenced, and the existing device is low in efficiency, poor in stability and short in service life.
In order to improve the efficiency, stability and lifetime of organic electroluminescent devices, device structure improvement and new material development must be performed to meet the requirements of future flat panel displays and lighting.
Therefore, there is a need to develop materials for organic electroluminescent devices having more excellent properties.
Disclosure of Invention
An object of the present invention is to provide an organic light emitting composite material capable of improving the efficiency and lifetime of an organic electroluminescent device as a light emitting layer, the organic light emitting composite material comprising a host material comprising at least one first organic compound and at least one second organic compound and a guest material which is a phosphorescent compound or a fluorescent compound, characterized in that,
the difference between the singlet level and the triplet level of the first organic compound is not more than 0.2eV, preferably not more than 0.15eV, more preferably not more than 0.1 eV;
the difference between the singlet level and the triplet level of the second organic compound is not less than 0.1eV, preferably not less than 0.2eV, and more preferably not less than 0.3 eV.
In another aspect, the present invention also provides an organic electroluminescent device comprising:
a first electrode and a second electrode opposed to each other,
a light-emitting layer comprising the organic light-emitting composite material, which is located between the first electrode and the second electrode,
a hole transport region between the first electrode and the light emitting layer,
an electron transport region between the second electrode and the light emitting layer,
wherein the hole transport region comprises a combination of one or more of a hole injection layer, a hole transport layer, an electron blocking layer; the electron transport region comprises one or more of an electron injection layer, an electron transport layer, and a hole blocking layer in combination.
In another aspect, the present invention also relates to the use of the organic light emitting composite material of the present invention as described above for an organic electroluminescent device.
In a further aspect, the invention also relates to a lighting or display element comprising said organic electroluminescent device.
The organic electroluminescent device made of the organic luminescent composite material has the advantages of high efficiency and long service life.
In the organic light emitting composite material of the present invention, the host material is composed of two materials, wherein the first compound has a small singlet-triplet energy level difference (Δ E)st) The thermally activated delayed fluorescence material of (1). The thermal activation delayed fluorescent material can realize effective reverse intersystem crossing, reduce the concentration of triplet excitons of a host material, reduce the quenching probability of the triplet excitons and improve the stability of a device.
The second compound of the present invention is a compound having a carrier mobility different from that of the first compound. Due to the large difference of the mobility of electrons and holes in a single host material, the carrier balance degree in the device is often influenced, so that the efficiency and stability of the device are poor, and the service life of the device is short. When a second compound with the carrier mobility different from that of the first compound is introduced, carriers in the main body material can be balanced, so that exciton recombination efficiency in the light-emitting layer is improved, and device efficiency is improved.
Meanwhile, the triplet energy level of the second compound is higher than the singlet energy level of the first compound (S1), so that energy return of the first compound and the guest material can be effectively prevented, and the efficiency, stability and service life of the device are further improved.
The organic electroluminescent device containing the organic luminescent composite material has good application effect and good industrialization prospect.
Drawings
Fig. 1 is a schematic view of an embodiment of an organic electroluminescent device of the present invention, in which:
1. substrate
2. Anode
3. Hole injection layer
4. Hole transport layer
5. Electron blocking layer
6. Luminescent layer
7. Electron transport layer
8. Electron injection layer
9. Cathode electrode
Detailed Description
Hereinafter, the embodiments shown in the present specification will be described in detail.
In the context of the present invention, HOMO means the highest occupied orbital of a molecule and LUMO means the lowest unoccupied orbital of a molecule, unless otherwise indicated. In addition, the "difference in HOMO energy levels" and "difference in LUMO energy levels" referred to in the present specification mean a difference in absolute value of each energy value. Furthermore, in the context of the present invention, the HOMO and LUMO energy levels are represented by absolute values, and the comparison between the energy levels is also a comparison of their absolute values, the skilled person knowing that the larger the absolute value of an energy level, the lower the energy of that energy level.
In the context of the present invention, unless otherwise indicated, the singlet (S1) energy level means the singlet lowest excited state energy level of the molecule, and the triplet (T1) energy level means the triplet lowest excited state energy level of the molecule. In addition, "difference in triplet energy level", and "difference between singlet and triplet energy levels" referred to in the present specification mean a difference in absolute value of each energy value. In addition, the difference between the energy levels is expressed in absolute values. The singlet and triplet energy levels can be measured by fluorescence and phosphorescence spectra, respectively, as is well known to those skilled in the art.
It will be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening elements may also be present. Further, it will be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present.
In one aspect, the present invention provides an organic light emitting composite material capable of improving efficiency and lifetime of an organic electroluminescent device as a light emitting layer, the organic light emitting composite material comprising a host material and a guest material, the host material comprising at least one first organic compound and at least one second organic compound, the guest material being a phosphorescent compound or a fluorescent compound, characterized in that,
the difference between the singlet level and the triplet level of the first organic compound is not more than 0.2eV, preferably not more than 0.15eV, more preferably not more than 0.1 eV;
the difference between the singlet level and the triplet level of the second organic compound is not less than 0.1eV, preferably not less than 0.2eV, and more preferably not less than 0.3 eV.
In a preferred embodiment, the singlet level of the first organic compound is less than the triplet level of the second organic compound, and the difference is not less than 0.1eV, preferably not less than 0.15eV, more preferably not less than 0.2 eV;
the first organic compound and the second organic compound have different carrier transport characteristics.
In the organic light emitting composite material of the present invention, the host material is composed of two materials, wherein the first compound has a small singlet-triplet energy level difference (Δ E)st) The thermally activated delayed fluorescence material of (1). The thermal activation delayed fluorescent material can realize effective reverse intersystem crossing, reduce the concentration of triplet excitons of a host material, reduce the quenching probability of the triplet excitons and improve the stability of a device. The second compound is a compound with different carrier mobility from the first compound, and can balance carriers in the main body material, so that exciton recombination efficiency in the light-emitting layer is improved, and device efficiency is improved. Meanwhile, the triplet energy level of the second compound is higher than the singlet energy level of the first compound (S1), so that energy return of the first compound and the guest material can be effectively prevented, and the efficiency, stability and service life of the device are further improved.
In the present invention, there is no particular limitation on the selection of the first organic compound and the second organic compound constituting the host material as long as their singlet and triplet energy levels and carrier mobility satisfy the above conditions.
In a preferred embodiment, the absolute value of the LUMO level of the first organic compound is larger than the absolute value of the LUMO level of the second organic compound, and the difference is not less than 0.1eV, preferably not less than 0.2 eV;
the absolute value of the difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is not more than 1.0eV, preferably not more than 0.6eV, more preferably not more than 0.4 eV.
In a preferred embodiment, the LUMO level of the first organic compound is in the range of 2.5 to 3.5eV, preferably in the range of 2.7 to 3.1 eV; the LUMO level of the second organic compound is in the range of 2.0 to 3.0eV, preferably in the range of 2.3 to 2.7 eV.
In a preferred embodiment, the HOMO level of the first organic compound is in the range of 5.0-6.5eV, preferably in the range of 5.5-6.0 eV; the HOMO level of the second organic compound is in the range of 5.0-6.5eV, preferably in the range of 5.5-6.5 eV.
In a preferred embodiment, the first organic compound has an electron mobility greater than a hole mobility, and the second organic compound has an electron mobility less than a hole mobility.
In a preferred embodiment, the first organic compound has an electron mobility less than a hole mobility, and the second organic compound has an electron mobility greater than a hole mobility.
In a preferred embodiment, the first organic compound is selected from the following compounds:
Figure BDA0001662883510000051
Figure BDA0001662883510000061
the second organic compound is selected from the following compounds:
Figure BDA0001662883510000071
Figure BDA0001662883510000081
in a particularly preferred embodiment, the first organic compound is selected from compounds having the following structural formula:
Figure BDA0001662883510000082
in a particularly preferred embodiment, the second organic compound is selected from compounds having the following structural formula:
Figure BDA0001662883510000091
there is no particular limitation on the weight ratio of the first organic compound and the second organic compound constituting the host material. In a preferred embodiment, the weight ratio of the first organic compound and the second organic compound is from 5:1 to 1:5, and the weight ratio of the first organic compound and the second organic compound is from 9:1 to 1:9, preferably from 7:3 to 3:7, preferably from 4:1 to 1:4, preferably from 3:1 to 1:3, more preferably from 2:1 to 1:2, more particularly 1: 1.
In the present invention, there is no particular limitation on the selection of the guest material. The guest material may be a phosphorescent compound or a fluorescent compound, wherein the fluorescent compound includes a thermally activated delayed fluorescence material. Wherein the difference between the singlet state energy level and the triplet state energy level of the thermally activated delayed fluorescence material is not more than 0.2 eV.
In a preferred embodiment, the guest material is selected from compounds having the following structural formula:
Figure BDA0001662883510000092
there is no particular limitation on the weight ratio of the constituent host and guest materials. In a preferred embodiment, the guest material is present in an amount of 0.5 to 20 wt%, preferably 1 to 15 wt%, more preferably 2 to 12 wt%, relative to the weight of the host material, based on the weight of the host material.
In the present invention, the first organic compound: a second organic compound: the guest material (weight ratio) is (80-20): (20-80): (1-20), preferably (70-30): (30-70): (6-18), more preferably (70-30): (30-70): (8-12), more preferably (70-30): (30-70): 12, more preferably 50: 50: (8-12), most preferably 50: 50: 12.
in another aspect, the invention relates to an organic electroluminescent device comprising
A first electrode and a second electrode opposed to each other,
a light emitting layer between the first electrode and the second electrode,
a hole transport region between the first electrode and the light emitting layer,
an electron transport region between the second electrode and the light emitting layer,
wherein the light-emitting layer comprises the organic light-emitting composite of the present invention as described above,
wherein the hole transport region comprises a combination of one or more of a hole injection layer, a hole transport layer, an electron blocking layer; the electron transport region comprises one or more of an electron injection layer, an electron transport layer, and a hole blocking layer in combination.
In one embodiment, the first electrode may be an anode and the second electrode may be a cathode.
Generally, in an organic light emitting device, electrons are injected from a cathode and transported to a light emitting layer, and holes are injected from an anode and transported to the light emitting layer.
In a preferred embodiment, the anode comprises a metal, metal oxide or a conductive polymer. For example, the anode can have a work function in the range of about 3.5 to 5.5 eV. Illustrative examples of conductive materials include carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, other metals, and alloys thereof; zinc oxide, indium oxide, tin oxide, Indium Tin Oxide (ITO),Indium zinc oxide and other similar metal oxides; and mixtures of oxides and metals, e.g. ZnO, Al and SnO2Sb. Both transparent and non-transparent materials can be used as anode materials. For a structure emitting light to the anode, a transparent anode may be formed. Herein, transparent means a degree to which light emitted from the organic material layer is transparent, and the transmittance of light is not particularly limited.
For example, when the organic light emitting device of the present specification is a top emission type and an anode is formed on a substrate before an organic material layer and a cathode are formed, not only a transparent material but also a non-transparent material having excellent light reflectivity may be used as an anode material. In another embodiment, when the organic light emitting device of the present specification is of a bottom emission type and the anode is formed on the substrate before the organic material layer and the cathode are formed, a transparent material is required to be used as an anode material, or a non-transparent material is required to be formed as a thin film which is thin enough to be transparent.
In a preferred embodiment, as for the cathode, a material having a small work function is preferable as a cathode material so that electron injection can be easily performed.
For example, in the present specification, a material having a work function ranging from 2eV to 5eV may be used as the cathode material. The cathode may comprise a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; materials having a multilayer structure, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
The cathode may be formed using the same material as the anode. In this case, the cathode may be formed using the anode material as described above. In addition, the cathode or anode may comprise a transparent material.
The organic light emitting device of the present invention may be a top emission type, a bottom emission type, or a both-side emission type, depending on the material used.
In a preferred embodiment, the organic light emitting device of the present invention comprises a hole injection layer. The hole injection layer may preferably be disposed between the anode and the light emitting layer. The hole injection layer is formed of a hole injection material known to those skilled in the art. The hole injection material is a material that easily receives holes from the anode at a low voltage, and the HOMO of the hole injection material is preferably located between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include, but are not limited to, metalloporphyrin-based organic materials, oligopolythiophene-based organic materials, arylamine-based organic materials, hexacarbonitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, organic-based materials, anthraquinone-based conductive polymers, polyaniline-based conductive polymers, polythiophene-based conductive polymers, or the like.
In a preferred embodiment, the organic light emitting device of the present invention comprises a hole transport layer. The hole transport layer may preferably be disposed between the hole injection layer and the light emitting layer, or between the anode and the light emitting layer. The hole transport layer is formed of a hole transport material known to those skilled in the art. The hole transport material is preferably a material having high hole mobility, which is capable of transferring holes from the anode or the hole injection layer to the light-emitting layer. Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having a bonding portion and a non-bonding portion.
In a preferred embodiment, the organic light emitting device of the present invention further comprises an electron blocking layer. The electron blocking layer may preferably be disposed between the hole transport layer and the light emitting layer, or between the hole injection layer and the light emitting layer, or between the anode and the light emitting layer. The electron blocking layer is formed of an electron blocking material known to those skilled in the art, such as EB 1.
In a preferred embodiment, the organic light emitting device of the present invention comprises an electron injection layer. The electron injection layer may preferably be disposed between the cathode and the light emitting layer. The electron injection layer is formed of an electron injection material known to those skilled in the art. The electron injection layer may be formed using, for example, an electron accepting organic compound. Here, as the electron accepting organic compound, known optional compounds may be used without particular limitation. As such organic compounds, there can be used: polycyclic compounds, such as p-terphenyl or quaterphenyl or derivatives thereof; polycyclic hydrocarbon combinationSubstances such as naphthalene, tetracene, coronene, chrysene, anthracene, diphenylanthracene or phenanthrene, or derivatives thereof; or a heterocyclic compound, for example, phenanthroline, bathophenanthroline, phenanthridine, acridine, quinoline, quinoxaline or phenazine, or a derivative thereof. Inorganic materials may also be used for formation, including, but not limited to, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; LiF, LiO2、LiCoO2、NaCl、MgF2、CsF、CaF2、BaF2、NaF、RbF、CsCl、Ru2CO3、YbF3Etc.; and materials having a multilayer structure, e.g. LiF/Al or LiO2Al, etc.
In a preferred embodiment, the organic light emitting device of the present invention comprises an electron transport layer. The electron transport layer may preferably be disposed between the electron injection layer and the light emitting layer, or between the cathode and the light emitting layer. The electron transport layer is formed of an electron transport material known to those skilled in the art. The electron transport material is a material capable of easily receiving electrons from the cathode and transferring the received electrons to the light emitting layer. Materials with high electron mobility are preferred. Specific examples of the electron transport material include, but are not limited to, 8-hydroxyquinoline aluminum complex; comprising Alq3A complex of (8-hydroxyquinoline) aluminum); an organic radical compound; and hydroxyflavone metal complexes; and mixtures of ET1 and Liq in a mass ratio of 8:2 to 2:8, preferably 7:3 to 3:7, preferably 5:4 to 4:5, for example 1: 1.
In a preferred embodiment, the organic light emitting device of the present invention further comprises a hole blocking layer. The hole blocking layer may preferably be disposed between the electron transport layer and the light emitting layer, or between the electron injection layer and the light emitting layer, or between the cathode and the light emitting layer. The hole blocking layer is a layer that reaches the cathode by preventing injected holes from passing through the light emitting layer, and may be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP (2, 9-dimethyl-4, 7-biphenyl-1, 10-phenanthroline), aluminum complexes, and the like, but are not limited thereto.
In a preferred embodiment, the hole blocking layer may be the same layer as the electron transport layer.
In addition, according to an embodiment of the present specification, the organic light emitting device may further include a substrate. In particular, in the organic light emitting device, the first electrode or the second electrode may be provided on the substrate. There is no particular limitation on the substrate. The substrate may be a rigid substrate, such as a glass substrate, or may be a flexible substrate, such as a flexible film-shaped glass substrate, a plastic substrate, or a film-shaped substrate.
The organic light emitting device of the present invention can be produced using the same materials and methods known in the art. For example, the organic light emitting device of the present invention may be manufactured by sequentially depositing a first electrode, one or more organic material layers, and a second electrode on a substrate. Specifically, the organic light emitting device can be produced by the following steps: depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a Physical Vapor Deposition (PVD) process (e.g., sputtering or e-beam evaporation) to form an anode; forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer on the anode; followed by deposition thereon of a material that can be used to form the cathode. In addition, an organic light emitting device may also be fabricated by sequentially depositing a cathode material, one or more organic material layers, and an anode material on a substrate. In addition, during the manufacture of the organic light emitting device, the organic light emitting composite material of the present invention may be formed into an organic material layer using a solution coating method in addition to a physical vapor deposition method. As used in this specification, the term "solution coating method" means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
There is no particular limitation on the thickness of each layer, and those skilled in the art can determine it as needed and as the case may be.
In a preferred embodiment, the thickness of the light-emitting layer and optionally of the hole-injecting layer, the hole-transporting layer, the electron-blocking layer and the electron-transporting layer, the electron-injecting layer, respectively, is from 0.5 to 150nm, preferably from 1 to 100 nm.
In a preferred embodiment, the thickness of the light-emitting layer is from 20 to 80nm, preferably from 30 to 60 nm.
The organic electroluminescent device containing the organic luminescent composite material has the advantages of higher device efficiency and longer service life.
The invention also relates to a lighting or display element comprising said organic electroluminescent device.
Furthermore, the present invention relates to the use of the organic light-emitting composite material of the present invention as described above for an organic electroluminescent device.
Examples
The present invention will be described in more detail below with reference to production examples, but the scope of the present invention is not limited by these production examples.
The various materials used in the examples and comparative examples are commercially available or can be obtained by methods known to those skilled in the art.
The molecular structural formula of the related material is shown as follows:
Figure BDA0001662883510000141
wherein the results of the respective energy level measurements of the host material and the guest material are as follows:
h1: HOMO was 5.86eV, LUMO was 3.09eV, S1 was 2.78eV, T1 was 2.71eV, Δ EstIs 0.07 eV;
h2: HOMO was 5.68eV, LUMO was 2.76eV, S1 was 2.78eV, T1 was 2.73eV, Δ Est0.05 eV;
h3: HOMO was 5.9eV, LUMO was 2.95eV, S1 was 2.8eV, T1 was 2.72eV, Δ EstIs 0.08 eV;
h4: HOMO was 5.82eV, LUMO was 2.80eV, S1 was 2.82eV, T1 was 2.71eV, Δ Est0.11 eV;
h20: HOMO was 6.01eV, LUMO was 2.58eV, S1 was 3.52eV, T1 was 2.94eV, Δ Est0.58 eV;
h21: HOMO was 5.6eV, LUMO was 2.42eV, S1 was 3.45eV, T1 was 2.98eV, Δ EstIs 0.47eV；
DP-1: HOMO was 5.41eV, LUMO was 2.71eV, S1 was 2.62eV, T1 was 2.45eV, Δ Est0.17 eV;
DP-2: HOMO was 5.51eV, LUMO was 2.9eV, S1 was 2.61eV, T1 was 2.48eV, Δ EstIs 0.13 eV;
and (3) CBP: HOMO was 6.17Ev, LUMO was 2.73eV, S1 was 3.2eV, T1 was 2.52eV, Δ Est0.68 eV;
the measuring method comprises the following steps:
the HOMO energy level is measured by an IPS-3 ionization energy measuring system, and the measuring steps are as follows: a sample film is evaporated on the ITO full-face glass to be 60 nm; placing the sample in a sample table of an IPS-3 ionization energy testing system, and vacuumizing to 5x10-2Pa; applying voltage on the sample, detecting the electrons emitted from the surface of the sample, and feeding back in the form of current; and (4) obtaining the ionization energy of the electrons through curve fitting, namely obtaining the HOMO value of the sample.
The LUMO energy level is obtained by indirectly measuring the band gap of a sample through calculation, and the measuring steps are as follows: a sample thin film is evaporated to 60nm on blank glass, the absorption of a sample is measured by an ultraviolet-visible spectrophotometer, the absorption wavelength of the sample is obtained through absorption cut-off edges, then the band gap of the sample is converted by E-1240/lambda, and the LUMO value of the sample can be obtained through the difference between the HOMO energy level and the band gap of the sample.
The S1 energy level and the T1 energy level are obtained by measuring the normal temperature and low temperature PL spectra of the sample, and the measuring steps are as follows: a mixed single film of the above materials was prepared in a vacuum evaporation chamber, and then a normal-temperature PL spectrum and a low-temperature PL spectrum of the above single film were measured, respectively. The normal temperature PL spectrum irradiates the surface of a sample through a 325nm laser light source, and the emergent light of the sample is detected to obtain the peak wavelength of an excitation spectrum. Low temperature PL Spectroscopy the peak wavelength of the excitation spectrum was obtained by cooling the sample to 35K, irradiating the sample surface with a 325nm laser light source, and detecting the emitted light. Then, the formula E is 1240/lambda to convert S1、T1To yield Δ EstThe value of (c).
The carrier mobility (hole mobility and electron mobility) measurement results of the host materials are shown in the following table:
TABLE 1
Name of Material Hole mobility (cm)2/V·S) Electron mobility (cm)2/V·S)
H1 5.32×10-4 3.45×10-2
H2 5.12×10-4 5.24×10-2
H3 4.58×10-4 2.38×10-2
H4 2.89×10-4 6.45×10-2
H20 8.76×10-3 2.01×10-3
H21 7.98×10-3 1.52×10-3
CBP 8.23×10-3 1.02×10-3
The measuring method comprises the following steps:
hole mobility and electron mobility were measured by a linear carrier pumping method, and the measurement steps were as follows:
preparing a single charge device from a sample, applying a positive periodic pulse linear increasing voltage to the single charge device, and instantaneously extracting carriers in the single charge device while linearly increasing the voltage, wherein the time for the voltage duration is more than or equal to the carrier degree; the single charge device has initial current in balance state, transient current changes with time along with the increase of linear boosting signal, when the changing current reaches the maximum value, the current carrier is completely extracted, and the time required by the process is tmax. Finally, the formula can be followed:
Figure BDA0001662883510000161
calculating the order of magnitude of the carrier mobility, tmaxTo vary the time for the current to reach the maximum, d is the measured thickness, a is the slope of the linear boost signal, and μ is the mobility.
Comparative example 1:
the device structure is shown in fig. 1, and the specific preparation process of the device is as follows:
cleaning the ITO anode layer 2 on the transparent glass substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes; drying the ITO glass substrate, placing the ITO glass substrate in a vacuum cavity until the vacuum degree is less than 2 multiplied by 10-6Torr, evaporating a mixture of HT1 and P1 with the film thickness of 10nm on the ITO anode layer 2, wherein the mass ratio of HT1 to P1 is 97:3, and the layer is a hole injection layer 3; next, HT1 was evaporated to a thickness of 80nm to form a hole transport layer4; then evaporating EB1 with the thickness of 20nm, wherein the layer is used as an electron blocking layer 5; further, 40nm of the light emitting layer 6 was evaporated: the method comprises the following steps of (1) taking CBP as a host material and DP-1 as a green phosphorescent doped dye (guest material), wherein the mass ratio of the CBP to the DP-1 is 100:12, and performing rate control through a film thickness meter; further evaporating ET1 and Liq (lithium hydroxyquinoline) with the thickness of 40nm on the light-emitting layer 6, wherein the mass ratio of the ET1 to the Liq is 1:1, and the organic material of the layer is used as a hole blocking/electron transporting layer 7; vacuum evaporating LiF with the thickness of 1nm on the hole blocking/electron transporting layer 7, wherein the layer is an electron injection layer 8; on the electron injection layer 8, a cathode Al (80nm) was vacuum-evaporated, which was a cathode electrode layer 9.
The results of measuring IVL data, luminance decay lifetime of the device are shown in Table 3, in which the external quantum efficiency was measured by an integrating sphere (model C9920-12) test system and LT95 lifetime was measured using an OLED lifetime tester (model M6000, Nanjing Bo luxury Yonghuai electronic technology Co., Ltd.).
Comparative example 2:
the electroluminescent device was prepared in the same manner as in comparative example 1 above, except that the guest material was changed in comparative example 2. The results of measuring IVL (current-voltage-luminance characteristic) data and luminance decay lifetime of the device are shown in table 3.
Comparative examples 3 to 10
The electroluminescent device was completed in the same manner as in comparative example 1 above, except that the host material in comparative examples 3 to 10 was the first organic compound of the present invention. The results of measuring the IVL data and the luminance decay lifetime of the device are shown in Table 3. The device compositions of comparative examples 1-10 are shown in table 2.
TABLE 2
Figure BDA0001662883510000181
The device measurement performance results of comparative examples 1 to 10 are shown in table 3.
TABLE 3
Numbering External quantum efficiency (10 mA/cm)2) Maximum external quantum efficiency LT95 Life (h)
Comparative example 1 11.8％ 14.8％ 98
Comparative example 2 8.2％ 13.6％ 46
Comparative example 3 12.5％ 15.4％ 168
Comparative example 4 13.2％ 16.1％ 157
Comparative example 5 12.8％ 15.9％ 148
Comparative example 6 11.9％ 14.2％ 162
Comparative example 7 13.1％ 16.3％ 76
Comparative example 8 12.8％ 15.8％ 86
Comparative example 9 14.2％ 16.6％ 82
Comparative example 10 13.6％ 15.2％ 79
As can be seen from the data in the table, comparative examples 3-10 have smaller difference in singlet-triplet energy levels (Δ E) with the present invention than comparative examples 1-2st) Compared with the traditional material (the difference between the singlet state and the triplet state is larger than 0.15eV) which is used as the main material, the device efficiency and the device stability of the thermal activation delayed fluorescence material (H1-H4) which is used as the main material are obviously improved. The main reason is to have a smaller Δ EstThe thermal activation delayed fluorescent material can realize effective reverse intersystem crossing, reduce the concentration of triplet excitons of a main material, reduce the quenching probability of the triplet excitons and improve the stability of a device.
Examples 1 to 16
The electroluminescent device was completed in the same manner as in comparative example 1 above, except that the host materials in examples 1 to 16 contained two organic compounds (a first organic compound and a second organic compound), wherein the singlet and triplet energy levels and the carrier mobility were within the range of the present invention. The results of measuring the IVL data and the luminance decay lifetime of the device are shown in Table 5.
The device compositions of examples 1-16 are shown in table 4.
TABLE 4
Figure BDA0001662883510000191
Figure BDA0001662883510000201
The device measurement performance results of examples 1-16 are shown in table 5.
TABLE 5
Figure BDA0001662883510000202
Figure BDA0001662883510000211
As can be seen from the data in the table, in examples 1 to 16, compared with comparative examples 3 to 10 in Table 3, the device efficiency and the lifetime are significantly improved by using the host material formed by matching the two materials. For example, the external quantum efficiency is 10mA/cm2The efficiency and lifetime of an electroluminescent device made of the following dual bodies are significantly improved:
Figure BDA0001662883510000212
specifically, taking inventive example 1 as an example, the external quantum efficiency of the device obtained using the combination of two organic compounds (H1 and H20) as host materials was improved from 12.5% to 18.4% (an improvement of 47.2%) and the lifetime was improved from 168H to 256H (an improvement of 52.4%) compared to the device obtained using one organic compound H1 alone as host material in comparative example 3. The efficiency and lifetime of the device are significantly improved. The main reason is that the mobility of electrons and holes in a single main body material has a certain difference, which often affects the balance of carriers in the device, resulting in poor efficiency and stability and short service life of the device. When a second compound with the carrier mobility different from that of the first compound is introduced, carriers in the main body material can be balanced, so that exciton recombination efficiency in the light-emitting layer is improved, and device efficiency is improved. Meanwhile, the first compound has a small singlet-triplet energy level difference (Δ E)st) The material can realize effective reverse intersystem crossing, reduce the concentration of triplet excitons of the host material, reduce the quenching probability of the triplet excitons and improve the stability of the device. In addition, the triplet energy level of the second compound is higher than the singlet energy level of the first compound (S1), so that energy return of the first compound and the guest material can be effectively prevented, and the efficiency, stability and lifetime of the device are further improved.

Claims (19)

1. An organic light-emitting composite material comprising a host material comprising at least one first organic compound and at least one second organic compound and a guest material which is a phosphorescent compound or a fluorescent compound,
the difference between the singlet state energy level and the triplet state energy level of the first organic compound is not more than 0.2 eV;
the difference between the singlet state energy level and the triplet state energy level of the second organic compound is not less than 0.1 eV;
wherein the first organic compound is selected from the following compounds:
Figure FDA0003285162500000011
Figure FDA0003285162500000021
the second organic compound is selected from the following compounds:
Figure FDA0003285162500000022
2. the organic light-emitting composite material according to claim 1,
the first organic compound and the second organic compound have different carrier transport characteristics.
3. The organic light-emitting composite material of claim 1, wherein the difference between the singlet and triplet energy levels of the first organic compound is no greater than 0.15 eV.
4. The organic light-emitting composite material according to claim 3, wherein the difference between the singlet energy level and the triplet energy level of the first organic compound is not more than 0.1 eV.
5. The organic light-emitting composite material according to claim 1, wherein the difference between the singlet energy level and the triplet energy level of the second organic compound is not less than 0.2 eV.
6. The organic light-emitting composite material according to claim 5, wherein the difference between the singlet energy level and the triplet energy level of the second organic compound is not less than 0.3 eV.
7. The organic light-emitting composite material according to claim 1,
an absolute value of a LUMO level of the first organic compound is larger than an absolute value of a LUMO level of the second organic compound, and a difference thereof is not less than 0.1 eV;
the absolute value of the difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is not more than 1.0 eV.
8. The organic light-emitting composite material according to claim 7,
the absolute value of the LUMO level of the first organic compound is larger than the absolute value of the LUMO level of the second organic compound, and the difference is not less than 0.2 eV.
9. The organic light-emitting composite material according to claim 7,
the absolute value of the difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is not more than 0.6 eV.
10. The organic light-emitting composite material according to claim 9,
the absolute value of the difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is not more than 0.4 eV.
11. The organic light-emitting composite of claim 1, wherein the first organic compound has an electron mobility greater than a hole mobility and the second organic compound has an electron mobility less than a hole mobility;
or the first organic compound has an electron mobility less than a hole mobility, and the second organic compound has an electron mobility greater than a hole mobility.
12. The organic light-emitting composite material according to claim 1, wherein the weight ratio of the first organic compound to the second organic compound is 9:1 to 1: 9.
13. The organic light-emitting composite material according to claim 12, wherein the weight ratio of the first organic compound to the second organic compound is 7:3 to 3: 7.
14. The organic light-emitting composite material of claim 1, wherein the fluorescent compound comprises a thermally activated delayed fluorescence material, and wherein the difference between the singlet energy level and the triplet energy level of the thermally activated delayed fluorescence material is no greater than 0.2 eV.
15. The organic light-emitting composite of claim 1, wherein the guest material is present in an amount of 0.5 to 20 wt% relative to the weight of the host material, based on the weight of the host material.
16. The organic light-emitting composite of claim 15, wherein the guest material is present in an amount of 1 to 15 wt% relative to the weight of the host material, based on the weight of the host material.
17. The organic light-emitting composite of claim 16, wherein the guest material is present in an amount of 2 to 12 wt% relative to the weight of the host material, based on the weight of the host material.
18. An organic electroluminescent device comprising the organic light-emitting composite of any one of claims 1 to 17, comprising:
a first electrode and a second electrode opposed to each other,
a light-emitting layer comprising the organic light-emitting composite material, which is located between the first electrode and the second electrode,
a hole transport region between the first electrode and the light emitting layer,
an electron transport region between the second electrode and the light emitting layer,
wherein the hole transport region comprises a combination of one or more of a hole injection layer, a hole transport layer, an electron blocking layer; the electron transport region comprises one or more of an electron injection layer, an electron transport layer, and a hole blocking layer in combination.
19. A lighting or display element comprising the organic electroluminescent device according to claim 18.
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