CN113563316B - Aromatic amine derivative and application thereof - Google Patents

Aromatic amine derivative and application thereof Download PDF

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CN113563316B
CN113563316B CN202010352120.3A CN202010352120A CN113563316B CN 113563316 B CN113563316 B CN 113563316B CN 202010352120 A CN202010352120 A CN 202010352120A CN 113563316 B CN113563316 B CN 113563316B
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hole transport
light emitting
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aromatic amine
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CN113563316A (en
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庞羽佳
张兆超
李崇
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Jiangsu Sunera Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

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  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to an aromatic amine derivative and application thereof, belonging to the technical field of semiconductors, and the structure of the compound provided by the invention is shown as a general formula (I): the invention also discloses application of the compound. The compound provided by the invention has stronger hole transmission capability, and improves hole injection and transmission performance under proper HOMO energy level; under the proper LUMO energy level, the electron blocking function is also realized, and the recombination efficiency of excitons in the light-emitting layer is improved; when the organic light-emitting diode is used as a light-emitting functional layer material of an OLED light-emitting device, the utilization rate and the radiation efficiency of excitons can be effectively improved by matching with the branched chains in the range of the invention.

Description

Aromatic amine derivative and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to an aromatic amine derivative and application thereof.
Background
The organic electroluminescent (OLED: organicLightEmissionDiodes) device technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, wherein various functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer act through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
At present, the OLED display technology has been applied to the fields of smart phones, tablet computers and the like, and further expands to the large-size application fields of televisions and the like, but compared with the actual product application requirements, the OLED display technology has the advantages that the luminous efficiency, the service life and the like of OLED devices are further improved. The studies on the improvement of the performance of the OLED light emitting device include: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the functional material of the OLED with higher performance is created.
When the organic OLED device is applied to a display apparatus, the organic OLED device is required to have a long life and high efficiency, particularly, a blue light device (compared with red and green light emitting devices) of a blue pixel region, which has a higher driving voltage and a shorter life. In order to prolong the service life of the blue pixel and reduce the driving voltage, the requirements on the phase stability and the thermal stability of the cavity transmission type material film are improved.
At present, the phase stability and the thermal stability of a film of a hole transport material are generally poor, and devices prepared from the materials still have the problems of high voltage and short service life, so that the materials with ideal phase stability and thermal stability of the film are required to be developed, thereby prolonging the service life of a blue light device and reducing the voltage of the device.
Disclosure of Invention
In view of the above problems in the prior art, the applicant provides an aromatic amine derivative and application thereof. The compound has higher hole mobility and proper HOMO energy level, and has stronger film phase stability and molecular thermal stability, so that the service life of an OLED device can be effectively prolonged, and the device voltage can be reduced.
The first aspect of the invention provides an aromatic amine derivative, which has a structure shown in a general formula (1):
r 1 is represented by a structure shown in a general formula (2), a general formula (3) and a general formula (4);
R, R 4 are each independently represented as phenyl, naphthyl or biphenyl;
R 2 represents a hydrogen atom, a phenyl group, a naphthyl group or a biphenyl group, and R 1 represents a structure represented by the general formula (4), R 2 cannot represent a hydrogen atom;
r 3 represents phenyl, biphenyl, terphenyl, phenylnaphthyl, biphenylnaphthyl or diphenylnaphthyl;
L represents a single bond, phenyl, naphthyl or biphenyl.
Preferably, the general formula (1) may be represented by any one of structures represented by general formulae (III-1) to (III-3):
R, R 4 are each independently represented as phenyl, naphthyl or biphenyl;
R 2 represents a hydrogen atom, a phenyl group, a naphthyl group or a biphenyl group, and R 2 in the general formula (III-3) is not represented as a hydrogen atom.
R 3 represents phenyl, biphenyl, terphenyl, phenylnaphthyl, biphenylnaphthyl or diphenylnaphthyl;
l represents a single bond, phenyl, naphthyl or biphenyl;
Further preferred, the specific structure of the derivative is as follows:
The second aspect of the invention provides application of the aromatic amine derivative in preparing an organic electroluminescent device.
A third aspect of the present invention is to provide an organic electroluminescent device comprising a cathode, an anode and an organic functional layer between the cathode and the anode, the organic functional layer containing the aromatic amine derivative.
A fourth aspect of the present invention is to provide an organic electroluminescent device, the organic functional layer comprising an electron blocking layer having such a feature that the electron blocking layer contains the aromatic amine derivative.
A fifth aspect of the present invention is to provide an organic electroluminescent device having such a feature that the organic functional layer includes a hole injection layer, a hole transport auxiliary layer, a light emitting layer, and an electron transport region, the hole transport auxiliary layer being adjacent to the light emitting layer, the hole injection layer including a P-doped material and an organic material, the hole transport layer including the same organic material as the hole injection layer, the hole transport auxiliary layer including an aromatic amine derivative, the hole auxiliary layer including one or two materials.
A sixth aspect of the present invention provides a full-color display device, which includes, in order from bottom to top, a substrate, a first electrode, an organic functional layer, and a second electrode, the organic functional layer including: a hole transport region located over the first electrode; a light emitting layer on the hole transporting region, the light emitting layer having a red light emitting layer, a green light emitting layer and a blue light emitting layer patterned in a red pixel region, a green pixel region and a blue pixel region, respectively; an electron transport region located over the light emitting layer; the hole transport region comprises a hole injection layer, a hole transport layer and a hole transport auxiliary layer from bottom to top in sequence, the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit have a common hole injection layer and a hole transport layer, and the hole transport region comprises the aromatic amine derivative shown in the general formula (1).
A seventh aspect of the present invention is to provide an illumination or display element having such features, including the above-described organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
In the case of a compound having high symmetry and a compound having high planarity, which contains a plurality of aryl groups in a molecule, crystallization tends to occur to block a crucible port for vapor deposition or crystallization occurs to cause a thin film defect, which results in low device yield in the production of an OLED device. The high sublimation temperature can lead to the problems of vapor deposition decomposition, uneven vapor deposition and the like, and the problems of shorter service life of devices and the like. Compared with the compound in the comparative patent (CN 108658953A, CN108368077A, KR 1020180063707A), the compound provided by the invention has relatively poorer flatness, so that the compound of the invention is not easy to generate the problem of blocking, has higher glass transition temperature and lower evaporation temperature, has better film phase stability, and can effectively improve the problem of poorer service life of devices;
the compound also has higher triplet state energy level, can effectively block exciton diffusion, and improves the exciton recombination efficiency of a luminescent layer;
The compound of the present application has high electron tolerance due to the inclusion of an arylamine group, and the EB layer is located next to the light-emitting layer, so that the material of the EB layer has high electron tolerance, and can inhibit the degradation (such as reduction or prevention) of the material caused by electrons not consumed in the light-emitting layer, thereby enabling the OLED device to have long life.
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device using the materials of the present invention;
Wherein 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking/electron transport layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a CPL layer.
FIG. 2 shows the results of experiments on crystallization of comparative compounds EB-5 and EB-6 of compound 4 of the present application.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention.
All materials in the examples described below were purchased from tobacco stand Mo Run fine chemicals Co., ltd.
Preparation of reactant A-1
(1) To a three-necked flask, 0.01mol of raw material I-1, 0.012mol of raw material I-2, 0.02mol of potassium carbonate and 5X 10 -5mol Pd(PPh3)4 were added, and then 250ml of toluene and 50ml of ethanol were added to dissolve the materials, and the mixture was refluxed for 4 hours with stirring, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and spin-evaporating the filtrate until no fraction is present. The resulting material was purified by column on silica gel (petroleum ether as eluent) to give intermediate II-1.
(2) To a three-necked flask, 0.01mol of intermediate II-1, 0.012mol of raw material I-3, 0.02mol of potassium carbonate and 5X 10 -5molPd(PPh3)4 were added, and then 250ml of toluene and 50ml of ethanol were added to dissolve the mixture, and the mixture was refluxed for 4 hours with stirring, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and spin-evaporating the filtrate until no fraction is present. The resulting material was purified by silica gel column (petroleum ether as eluent) to give intermediate II-2.
(3) To a three-necked flask, 0.01mol of intermediate II-2 and 0.012 molN-bromosuccinimide were added, and then 100ml of dimethylformamide was added to dissolve the intermediate, and the mixture was heated to 60℃and refluxed with stirring for 12 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, adding 100ml of 1mol/LNaOH solution, stirring, filtering and drying to obtain an aqueous intermediate II-3.
(4) To a three-necked flask, 0.01mol of intermediate II-3 and 0.015molNaH were added, followed by dissolution by addition of 80ml of dimethyl sulfone, heating to 140℃and stirring reflux for 5 hours, and the reaction was observed by TLC until the reaction was complete, and the solution was delaminated. Naturally cooling to room temperature, separating liquid, filtering and drying to obtain an intermediate II-4.
(5) Into a three-necked flask, 0.01mol of intermediate II-4, 0.012mol of raw material I-4, 0.02mol of potassium carbonate and 5X 10 -5molPd(PPh3)4 were added, then 250ml of toluene and 50ml of ethanol were added to dissolve them, and the mixture was refluxed for 4 hours with stirring, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and spin-evaporating the filtrate until no fraction is present. The resulting material was purified by silica gel column (petroleum ether as eluent) to afford intermediate II-5.
(6) To a three-necked flask, 0.01mol of intermediate II-5, 0.012mol of raw material I-5, 0.02mol of potassium carbonate and 5X 10 -5molPd(PPh3)4 were added, and then 250ml of toluene and 50ml of ethanol were added to dissolve the mixture, and the mixture was refluxed for 4 hours with stirring, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and spin-evaporating the filtrate until no fraction is present. The resulting material was purified by silica gel column (petroleum ether as eluent) to afford intermediate II-6.
The preparation of the other reactant A was similar to that of reactant A-1, except for the different starting materials used.
Preparation of reactant C-1
(1) To a three-necked flask, 0.01mol of raw material I-6, 0.012mol of raw material I-7, 0.02mol of potassium carbonate and 5X 10 -5mol Pd(PPh3)4 were added, and then 250ml of toluene and 50ml of ethanol were added to dissolve the materials, and the mixture was refluxed for 4 hours with stirring, and the reaction was observed by TLC until the reaction was completed. Naturally cooling to room temperature, filtering, and spin-evaporating the filtrate until no fraction is present. The resulting material was purified by column on silica gel (petroleum ether as eluent) to give intermediate II-6.
(2) Adding 0.01mol of intermediate II-6,0.01mol of raw material I-8 and 150ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5molPd2(dba)3,5×10-5molP(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide to remain, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain a reactant C-1.
The preparation of the other reactant C is similar to that of reactant C-1, except for the different starting materials used.
Example 1
Preparation of Compound 4
(1) Adding 0.01mol of reactant A-1,0.012mol of reactant B-1 and 150ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5molPd2(dba)3,5×10-5molP(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide to remain, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain an intermediate II-7;
(2) Adding 0.01mol of intermediate II-7,0.012mol of reactant C-1 and 150ml of toluene into a three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5molPd2(dba)3,5×10-5molP(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide residue, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain the compound 4.
Examples 2 to 22
The procedure for the preparation of compound 4 was repeated to synthesize the following compounds except that reactant A, reactant B and reactant C, as set forth in Table 1-1 below, were used, and the test results are also set forth in the following Table.
TABLE 1-1
For structural analysis of the compounds prepared in examples 1 to 22, molecular weight was measured by LC-MS, and 1H-NMR was measured by dissolving the prepared compound in a deuterated chloroform solvent and using a 500MHz NMR apparatus.
The nuclear magnetic data are shown in the following tables 1-2:
TABLE 1-2
The compound of the invention is used in a light-emitting device, can be used as a hole transport layer material and also can be used as an electron blocking layer material. The compounds prepared in the above examples of the present invention were tested for thermal properties, T1 energy level, HOMO energy level and hole mobility, respectively, and the test results are shown in table 2:
TABLE 2
Note that: the triplet state energy level T1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test condition of the material is toluene solution of 2 x 10 -5 mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the thermal weight loss temperature Td is a temperature at which the weight loss is 1% in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), tested as an atmospheric environment; eg was tested by a dual beam UV-Vis spectrophotometer (model: TU-1901); hole mobility test the materials of the present invention were fabricated into single charge devices and tested using the SCLC method.
As can be seen from the above table data, the organic compound of the present invention has a more suitable HOMO energy level, and can be applied to a hole transport layer or an electron blocking layer.
The effect of the OLED materials synthesized according to the present invention in the application to devices will be described in detail below with reference to device examples 1 to 30 and device comparative examples 1 to 4. The device examples 1-30 of the present invention were identical in device fabrication process to the device comparative examples 1-4, and the same substrate materials and electrode materials were used, and the film thickness of the electrode materials was also kept uniform, except that the hole transport layer materials or electron blocking layer materials in the devices were replaced.
Device comparative example 1
The preparation process comprises the following steps:
As shown in fig. 1, the transparent substrate layer 1 is washed with an ITO anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in order to remove organic residues on the surface of the anode layer. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, HT-1 was evaporated to a thickness of 120nm as a hole transport layer 4. Subsequently EB-3 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping proportion of the doping material is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the luminescent layer 6, the ET-1 and the Liq are continuously evaporated, and the mass ratio of the ET-1 to the Liq is 1:1. The vacuum deposition film of the material has a thickness of 30nm, and the vacuum deposition film is a hole blocking/electron transport layer 7. On the hole blocking/electron transporting layer 7, a LiF layer having a film thickness of 1nm, which is an electron injecting layer 8, was produced by a vacuum vapor deposition apparatus. On the electron injection layer 8, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as a cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as CPL layer 10.
Device examples 1-30: device examples 1-30 were prepared in the same manner as device comparative example 1, except that the electron blocking layer organic material was an organic compound of the present application.
Device comparative examples 2-4: device comparative examples 2 to 4 were prepared in the same manner as in device comparative example 1, except that the following organic materials were used for the electron blocking layer.
The molecular structural formula of the related material is shown as follows:
After the OLED light emitting device is completed as described above, the anode and cathode are connected by a well-known driving circuit, and the current efficiency of the device, the light emission spectrum, and the lifetime of the device are measured.
TABLE 3 Table 3
TABLE 4 Table 4
Note that: the voltage, current efficiency and color coordinates were tested using an IVL (Current-Voltage-Brightness) test system (Freund's scientific instruments, st., inc.), with a current density of 10mA/cm 2 at the time of testing; the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95% at a particular brightness (blue light: 1000nits; green light: 10000nits; red light: 5000 nits).
As can be seen from the device data results, the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over OLED devices of known materials, as compared to the device comparative examples.
To illustrate the stable phase of the film phase of the inventive subject matter, a film accelerated crystallization experiment was performed on inventive subject matter 4 with a comparative compound: evaporating different materials on alkali-free glass in a vacuum evaporation mode, packaging in a glove box (water oxygen content is less than 0.1 ppm), placing a packaged sample under the condition of (temperature is 85 ℃ and 115 ℃), and observing the surface morphology of the film by a microscope (LEICA, DM8000M and 5 x 10 multiplying power) periodically, wherein the surface morphology of the material is shown in figure 2;
As can be seen from the results of crystallization experiments of comparative compounds EB-5 and EB-6 of the compound 4 of the present application in FIG. 2, the surface morphology of the thin film of the compound 4 of the present application is unchanged regardless of whether the compound 4 of the present application is subjected to a standing experiment at 85 ℃ or 115 ℃, which indicates that the compound of the present application has excellent film phase stability; the EB-5 and EB-6 compound films have black spots at 85 ℃, and the black spots on the surfaces of the films at 115 ℃ become larger or even the whole film becomes black completely; from this, it can be judged that the compound of the present application has more excellent film phase stability than the comparative compounds EB-5 and EB-6.

Claims (6)

1. An aromatic amine derivative is characterized by comprising the following specific structures:
2. an organic electroluminescent device comprising a cathode, an anode and an organic functional layer, wherein the organic functional layer is located between the cathode and the anode, characterized in that at least one organic functional layer of the organic electroluminescent device comprises the aromatic amine derivative according to claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic functional layer comprises an electron blocking layer, wherein the electron blocking layer contains the aromatic amine derivative according to claim 1.
4. The organic electroluminescent device according to claim 2, wherein the organic functional layer comprises a hole injection layer, a hole transport auxiliary layer, a light emitting layer and an electron transport region, the hole transport auxiliary layer is adjacent to the light emitting layer, the hole injection layer comprises a P-doped material and an organic material, the hole transport layer comprises the same organic material as the hole injection layer, wherein the hole transport auxiliary layer contains the aromatic amine derivative according to claim 1, and the hole transport auxiliary layer comprises one or two materials.
5. A full-color display device, which sequentially comprises a substrate, a first electrode, an organic functional layer and a second electrode from bottom to top, wherein the organic functional layer comprises: a hole transport region located over the first electrode; a light emitting layer on the hole transporting region, the light emitting layer having a red light emitting layer, a green light emitting layer and a blue light emitting layer patterned in a red pixel region, a green pixel region and a blue pixel region, respectively; an electron transport region located over the light emitting layer; the hole transport region comprises a hole injection layer, a hole transport layer and a hole transport auxiliary layer from bottom to top in sequence, wherein the hole injection layer comprises a P-type doping material, and the red pixel unit, the green pixel unit and the blue pixel unit have a common hole injection layer and a hole transport layer and are provided with respective hole transport auxiliary layers, and the hole transport region is characterized in that the hole transport region contains the aromatic amine derivative of claim 1.
6. A lighting or display element comprising the organic electroluminescent device as claimed in any one of claims 2 to 4.
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