CN110526825B - Compound with structure of isoflexor and triarylamine as core and application thereof - Google Patents

Compound with structure of isoflexor and triarylamine as core and application thereof Download PDF

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CN110526825B
CN110526825B CN201810513477.8A CN201810513477A CN110526825B CN 110526825 B CN110526825 B CN 110526825B CN 201810513477 A CN201810513477 A CN 201810513477A CN 110526825 B CN110526825 B CN 110526825B
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CN110526825A (en
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李崇
张小庆
张兆超
王芳
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound taking an isoflexor and triarylamine structure as a core, a preparation method and application thereof, wherein the structure of the compound is shown as a general formula (1); the compound provided by the invention has higher glass transition temperature and molecular thermal stability, appropriate HOMO and LUMO energy levels and higher mobility, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.

Description

Compound with structure of isoflexor and triarylamine as core and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic compound with a main structure containing an alloplex and triarylamine structure and application thereof in an organic electroluminescent device.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect.
The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to 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 are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
At present, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, but compared with actual product application requirements, the light emitting efficiency, the service life, and other performances of the OLED device need to be further improved.
The research on the improvement of the performance of the OLED light emitting device includes: 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 the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the OLED photoelectric functional material are needed to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transport materials and luminescent materials, further, the charge injection transport materials can be divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the luminescent materials can be divided into main luminescent materials and doping materials.
In order to fabricate high-performance OLED light-emitting devices, various organic functional materials are required to have good photoelectric properties, for example, as charge transport materials, good carrier mobility, high glass transition temperature, etc. as well as host materials for light-emitting layers, which require good ambipolarity, appropriate HOMO/LUMO energy levels, etc.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in the devices with different structures can also be completely different.
Therefore, in order to meet the industrial application requirements of the current OLED device, and the requirements of different functional film layers and the photoelectric properties of the device, a more suitable and high-performance OLED functional material or material combination must be selected to realize the comprehensive properties of high efficiency, long service life and low voltage of the device. In terms of the actual requirements of the current OLED display illumination industry, the development of the current OLED materials is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop higher-performance organic functional materials as material enterprises.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides a compound with an isoflexor and triarylamine structure as a core and an application thereof in an organic electroluminescent device. The compound is not easy to crystallize, has higher heat-resistant stability and higher hole mobility, and obviously improves the service life and the efficiency of a device.
The technical scheme of the invention is as follows:
a compound with an alloprene and triarylamine structure as a core is disclosed, wherein the structure of the compound is shown as a general formula (1):
Figure BDA0001673269600000021
in the general formula (1), ar represents a single bond, phenylene, naphthylene, biphenylene, C 1-20 Phenylene substituted by a linear or branched alkyl radical, C 5-10 One of heteroarylenes;
the R is 1 、R 2 Each independently represents substituted or unsubstituted C 6-60 One of an aryl group, a substituted or unsubstituted 5-to 60-membered heteroaryl group containing one or more heteroatoms; the heteroatom is nitrogen, oxygen or sulfur;
the R represents a structure shown in a general formula (2) or a general formula (3):
Figure BDA0001673269600000031
in the general formula (3), a represents
Figure BDA0001673269600000032
Wherein, X 1 、X 2 Respectively is oxygen atom, sulfur atom, selenium atom, C 1-10 Straight-chain alkyl-substituted alkylene, C 1-10 Branched alkyl-substituted alkylene, C 6-60 Aryl-substituted alkylene, C 1-10 Straight or branched chain alkyl substituted amine, C 6-60 One of aryl substituted amine groups;
* Represents a structure represented by the general formula (2) or the general formula (3) and the general formula (1) through C L1 -C L2 Key, C L3 -C L4 Key, C L4 -C L5 Key, C L5 -C L6 Key, C L7 -C L8 Key, C L’1 -C L’2 Key, C L’3 -C L’4 Key, C L’4 -C L’5 C L’5 -C L’6 Key, C L’6 -C L’7 Bond or C L’7 -C L’8 A linked attachment site;
and n is 1, 2 or 3.
Further preferably, R is 1 、R 2 Respectively expressed as:
Figure BDA0001673269600000033
Figure BDA0001673269600000034
any one of the above.
Preferably, the structure of the compound is one of general formulas (4) to (11):
Figure BDA0001673269600000041
the specific structure of the compound is preferably:
Figure BDA0001673269600000042
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Figure BDA0001673269600000051
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Figure BDA0001673269600000061
/>
Figure BDA0001673269600000071
/>
Figure BDA0001673269600000081
/>
Figure BDA0001673269600000091
/>
Figure BDA0001673269600000101
/>
Figure BDA0001673269600000111
Figure BDA0001673269600000112
any one of the above. A preparation method of the compound, which comprises the following two conditions:
(a) When Ar is a single bond, the preparation reaction formula is
Figure BDA0001673269600000121
(1) Taking a reactant I and a reactant II as raw materials and toluene as a solvent, wherein the dosage of the toluene is 30-50 ml per gram of the reactant I, and the molar ratio of the reactant I to the reactant II is 1.0-1.5;
(2) Adding Pd into the reaction system in the step (1) 2 (dba) 3 And P (t-Bu) 3 To prepare a reaction system; wherein, the Pd 2 (dba) 3 In a molar ratio to reactant I of 0.005 to 0.01, said P (t-Bu) 3 The molar ratio of the reactant I to the reactant I is 1.5-3.0;
(3) Under the protection of nitrogen, reacting the reaction system in the step (2) at 95-110 ℃ for 10-24 hours, naturally cooling to room temperature, filtering the reaction solution, performing reduced pressure rotary evaporation on the filtrate, and passing through a neutral silica gel column to obtain a target compound;
(b) When Ar represents a single bond, the reaction equation is as follows:
Figure BDA0001673269600000122
(1) Taking a reactant I and an intermediate II as raw materials, and taking ethanol and toluene as solvents, wherein the ratio of the toluene to the ethanol is 2.8-1.2, the dosage of the toluene is 30-50 ml for each gram of the reactant I, and the molar ratio of the reactant I to the intermediate II is 1.0-1.5;
(2) Adding Pd (PPh) into the reaction system in the step (1) 3 ) 4 And sodium carbonate to prepare a reaction system; wherein, the Pd (PPh) 3 ) 4 The molar ratio of the potassium carbonate to a reactant I is 0.005-0.01;
(3) Under the protection of nitrogen, reacting the reaction system in the step (2) at 95-110 ℃ for 10-24 h, naturally cooling to room temperature, filtering the reaction solution, performing reduced pressure rotary evaporation on the filtrate, and passing through a neutral silica gel column to obtain a target compound;
the synthesis reaction equation of the intermediate II:
Figure BDA0001673269600000131
the preparation process comprises the following steps:
(1) Weighing an intermediate reactant II and a reactant III, and dissolving with toluene; then adding Pd 2 (dba) 3 、P(Ph) 3 Sodium tert-butoxide; reacting the mixed solution of the reactants at 95-110 ℃ for 10-24 h under inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate I; the molar ratio of the reactant II to the reactant III is 1.0-1.5, pd 2 (dba) 3 Molar ratio to reactant II is 0.006 to 0.02P (Ph) 3 The molar ratio of the sodium tert-butoxide to the reactant II is 0.006 to 0.02, and the molar ratio of the sodium tert-butoxide to the reactant II is 1.0 to 3.0;
(2) Weighing intermediate I, bis (pinacolato) diboron and Pd (dppf) Cl in the atmosphere of nitrogen 2 Dissolving potassium acetate in toluene, reacting for 12-24 hours at 100-120 ℃, sampling a sample, completely reacting, naturally cooling, filtering, rotatably steaming filtrate to obtain a crude product, and passing through a neutral silica gel column to obtain an intermediate II; the molar ratio of the intermediate I to the bis (pinacolato) diboron is 2:1-1.5, and the intermediate I and Pd (dppf) Cl 2 The molar ratio of the intermediate I to the potassium acetate is 1:2-2.5, and the molar ratio of the intermediate I to the potassium acetate is 1.
At least one functional layer of the organic electroluminescent device contains the compound taking an isoflexor and triarylamine structure as a core.
The hole transport layer material of the organic electroluminescent device is the compound taking an isoflexor and triarylamine structure as a core.
A lighting or display element comprising the organic electroluminescent device.
The beneficial technical effects of the invention are as follows:
the p-pi conjugated effect in the compound has strong hole transmission capability, and the high hole transmission rate can improve the efficiency of an organic electroluminescent device; the asymmetric triarylamine structure in the compound can reduce the crystallinity of molecules, reduce the planarity of the molecules and prevent the molecules from moving on the plane, thereby improving the thermal stability of the molecules. The aryl of the compound is bent into a mother nucleus and is connected with the nitrogen-containing branched chain, the structure has higher dielectric constant, so that the compound has higher refractive index, and simultaneously, after the material is formed into a film, all branched chains can be mutually crossed to form a film layer with high compactness, thereby reducing the leakage current of the material after the application of an OLED device and prolonging the service life of the device. .
The structure of the compound enables the distribution of electrons and holes in the luminescent layer to be more balanced, and under the proper HOMO energy level, the hole injection and transmission performance is improved; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; when the aryl group is used as a hole transmission functional layer material of an OLED light-emitting device, the aryl group and the branched chain in the range of the invention can effectively improve the hole transmission capability, thereby improving the exciton utilization rate, reducing the voltage of the device, improving the current efficiency of the device and prolonging the service life of the device.
When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, and the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved. The compound has good application effect and industrialization prospect in OLED luminescent devices.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
in the figure, 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is hole transport, 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, and 9 is a cathode reflective electrode layer.
FIG. 2 is a graph of the efficiency of OLED devices of the present invention measured at different temperatures.
Fig. 3 is a graph showing reverse voltage leakage current test curves of the devices manufactured in example 1 and comparative example 1.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
Example 1: synthesis of intermediate I:
Figure BDA0001673269600000141
weighing an intermediate reactant II and a reactant III, and dissolving the intermediate reactant II and the reactant III by using toluene; then adding Pd 2 (dba) 3 、P(Ph) 3 Sodium tert-butoxide; reacting the mixed solution of the reactants at 95-110 ℃ for 10-24 hours under inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate I; the molar ratio of the reactant II to the reactant III is 1.0-1.5, and Pd 2 (dba) 3 Molar ratio to intermediate reactant II is 0.006 to 0.02P (Ph) 3 The molar ratio of the sodium tert-butoxide to the reactant II is 0.006-0.02, and the molar ratio of the sodium tert-butoxide to the reactant II is 1.0-3.0;
taking the intermediate I-1 as an example:
Figure BDA0001673269600000151
weighing 0.02mol of reactant II-1 and 0.03mol of reactant III-1, and dissolving with toluene; then 0.0002molPd was added 2 (dba) 3 、0.0004molP(Ph) 3 0.09mol of sodium tert-butoxide; reacting the mixed solution of the reactants at 95 ℃ for 24 hours under the inert atmosphere, naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is produced, and passing through a neutral silica gel column to obtain a target product intermediate I-1; HPLC purity 99.53%, yield 75.5%; HRMS (EI) (high resolution mass spectrometry): theoretical value is 555.1562, found 555.1578.
Example 2: and (3) synthesis of an intermediate II:
Figure BDA0001673269600000152
weighing intermediate I, bis (pinacolato) diboron and Pd (dppf) Cl in the atmosphere of nitrogen 2 Dissolving potassium acetate in toluene, reacting for 12-24 hours at 100-120 ℃, sampling a sample, completely reacting, naturally cooling, filtering, rotatably steaming filtrate to obtain a crude product, and passing through a neutral silica gel column to obtain an intermediate II; the molar ratio of the intermediate I to the bis (pinacolato) diboron is 2:1-1.5, and the intermediate I and Pd (dppf) Cl 2 The molar ratio of the intermediate I to the potassium acetate is 1:2-2.5.
Taking the intermediate II-1 as an example:
Figure BDA0001673269600000153
weighing 0.02mol of intermediate I-1,0.012mol of bis (pinacolato) diboron and 0.0002mol of Pd (dppf) Cl in the atmosphere of nitrogen 2 Dissolving 0.05mol of potassium acetate in toluene, reacting for 12h at 120 ℃, sampling a sample point plate, completely reacting, naturally cooling, filtering, rotatably steaming filtrate to obtain a crude product, and passing through a neutral silica gel column to obtain an intermediate II-1; HPLC purity 99.35%, yield 76.3%; elemental analysis Structure (molecular formula C) 33 H 26 BNO 3 ): theoretical value C,80.01; h,5.29; b,2.18; n,2.83; o,9.69; test values are: c,80.01; h,5.28; b,2.18; n,2.84; o,9.69.ESI-MS (M/z) (M +): theoretical value is 495.38, found 495.29.
The synthesis starting materials for intermediate I and intermediate II required in the examples are shown in table 1:
TABLE 1
Figure BDA0001673269600000161
Example 3: synthesis of Compound 3:
Figure BDA0001673269600000162
adding 0.01mol of reactant I-1,0.012mol of reactant II-1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10 -5 molPd 2 (dba) 3 ，5×10 -5 molP(t-Bu) 3 Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the target product with the HPLC purity of 99.76% and the yield of 75.3%. HRMS (EI): the molecular weight of the material is 743.3552, and the measured molecular weight is 743.3549.
Example 4: synthesis of Compound 5:
Figure BDA0001673269600000171
compound 5 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-2, the desired product is obtained with a purity of 95.6% in 79% yield, HRMS (EI): calcd for 743.3552, found 743.3556.
Example 5: synthesis of compound 17:
Figure BDA0001673269600000172
adding 0.01mol of intermediate reactant I-1 and 0.015mol of intermediate II-1 into a 250ml three-necked bottle, and adding toluene and ethyl alcohol in a volume ratio of 2:1Dissolving an alcohol mixed solvent; under inert atmosphere, 0.02mol Na is added 2 CO 3 Aqueous solution (2M), 0.0001mol Pd (PPh) 3 ) 4 (ii) a And (3) reacting the mixed solution of the reactants for 10 to 24 hours at the reaction temperature of between 95 and 110 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target product with the purity of 99.80 percent and the yield of 74.3 percent. HRMS (EI): calcd for 819.3865, found 819.3815.
Example 6: synthesis of compound 26:
Figure BDA0001673269600000181
/>
compound 26 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-3, the desired product is obtained in 97.6% purity, yield 85%, HRMS (EI): calcd for 727.3239, found 727.3258.
Example 7: synthesis of compound 36:
Figure BDA0001673269600000182
compound 36 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-4, the desired product is obtained in 99.45% purity and 71% yield, HRMS (EI): calcd for 717.3032, found 717.3084.
Example 8: synthesis of compound 50:
Figure BDA0001673269600000183
compound 50 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-5 and reactant II-1 is replaced with reactant II-2, the desired product is obtained with a purity of 98.45% and a yield of 71%, HRMS (EI): calcd for 637.2770, found 637.2715.
Example 9: synthesis of compound 52:
Figure BDA0001673269600000191
compound 52 was prepared as in example 3, except that reactant I-1 was replaced with reactant I-5 and reactant II-1 was replaced with reactant II-3 to give the desired product in 97.65% purity and 78% yield, HRMS (EI): calcd for 637.2770, found 637.2758.
Example 10: synthesis of compound 73:
Figure BDA0001673269600000192
compound 73 was prepared as in example 3, except that reactant II-1 was replaced with reactant II-3, the desired product was obtained in 97.65% purity and 78% yield, HRMS (EI): calcd for 703.3239, found 703.3258.
Example 11: synthesis of compound 75:
Figure BDA0001673269600000193
compound 75 was prepared as in example 3, except that reactant I-1 was replaced with reactant I-2 and reactant II-1 was replaced with reactant II-3 to give the desired product in 98.99% purity and 69% yield, HRMS (EI): calcd for 703.3239, found 703.3248.
Example 12: synthesis of compound 87:
Figure BDA0001673269600000201
compound 87 is prepared as in example 6, except that reactant I-6 is substituted for I-1 and intermediate II-2 is substituted for intermediate II-1, the desired product is obtained in 98.99% purity and in 69% yield, as determined by HRMS (EI): calcd for 779.3552, found 779.3598.
Example 13: synthesis of compound 105:
Figure BDA0001673269600000202
/>
compound 105 was prepared as in example 6, except that reactant I-1 was replaced with reactant I-3 and intermediate II-1 was replaced with intermediate II-3, the target product was 98.25% pure and 69% yield, HRMS (EI): calcd for 763.3239, found 763.3216.
Example 14: synthesis of compound 106:
Figure BDA0001673269600000203
compound 106 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-4 and reactant II-1 is replaced with reactant II-3, the desired product is 99.16% pure in 81% yield, HRMS (EI): calcd for 677.2719, found 677.2733.
Example 15: synthesis of compound 117:
Figure BDA0001673269600000211
compound 117 was prepared as in example 3, except that reactant I-1 was replaced with reactant I-5 and reactant II-1 was replaced with reactant II-4 to give the desired product in 98.56% purity and 73% yield, HRMS (EI): calcd for 647.2613, found 647.2627.
Example 16: synthesis of compound 136:
Figure BDA0001673269600000212
compound 136 is prepared as in example 3, except that reactant I-1 is replaced with reactant I-7 and reactant II-1 is replaced with reactant II-5 to give the desired product in 99.56% purity and 83% yield, HRMS (EI): calcd for 703.3239, found 703.3226.
The compound of the invention is used in a light-emitting device and can be used as a hole transport layer material. The compounds prepared in the above embodiments of the present invention are respectively tested for thermal performance, T1 level, and HOMO level, and the test results are shown in table 2.
TABLE 2
Figure BDA0001673269600000213
Figure BDA0001673269600000221
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of Germany Chi-resistant company), and the heating rate is 10 ℃/min; the thermogravimetric loss temperature Td is a temperature at which 1% of the weight is lost in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, japan, and the nitrogen flow rate is 20mL/min; the triplet state energy level T1 is tested by an F4600 fluorescence spectrometer of Hitachi, and the test condition of the material is 2X 10-5 toluene solution; the highest occupied molecular orbital HOMO energy level and the lowest occupied molecular orbital LUMO energy level are tested by a photoelectron emission spectrometer (AC-2 type PESA) and are tested in an atmospheric environment;
the hole mobility was measured by a linear carrier-pressurization 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 an initial current in an equilibrium state, the transient current changes along with the increase of a linear boosting signal, and when the changing current reaches a maximum value, the current carrier is completely extracted, and the time required by the process is tmax. Finally, the formula can be followed:
Figure BDA0001673269600000222
and calculating the magnitude of the carrier mobility, wherein tmax is the time for the change current to reach the maximum value, d is the measured thickness, A is the slope of the linear boosting signal, and mu is the mobility.
As can be seen from the data in Table 2, the organic compound of the present invention has a high glass transition temperature, which can improve the phase stability of the material film, and further improve the service life of the device; the light-emitting diode has a proper T1 energy level, so that the energy loss of a light-emitting layer can be blocked, and the light-emitting efficiency of the device is improved; the appropriate HOMO energy level can solve the problem of injection of carriers and can reduce the voltage of the device. Therefore, the compound taking the structure of the isoflexor and the triarylamine as the core is applied to the hole transport layer of the OLED device, and can effectively improve the luminous efficiency and the service life of the device.
The effect of the compound synthesized according to the present invention as a hole transport layer in a device is explained in detail below by device examples 1 to 14 and device comparative example 1. Device examples 2 to 14 and device comparative example 1 were compared with device example 1 in that the manufacturing processes of the devices were completely the same, and the same substrate material and electrode material were used, and the film thicknesses of the electrode materials were also kept the same, except that the hole transport layer was changed in the devices. The device stack structure is shown in table 3, and the performance test results of each device are shown in tables 4 and 5.
Device example 1
As shown in FIG. 1, device examples used ITO as the anode, al as the cathode, CBP and Ir (ppy) 3 The compound 2 prepared by the embodiment of the invention is used as a hole transport layer, TPBI is used as an electron transport layer material, and LiF is used as an electron injection layer material. The specific manufacturing steps are as follows:
cleaning the ITO anode layer 2 on the transparent 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;
evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
the compound 3 prepared by the embodiment of the invention is evaporated with a hole transport layer material by a vacuum evaporation way on the hole injection layer 3, the thickness is 60nm, and the layer is a hole transport layer 4;
evaporating an electron blocking material TCTA (thermal transfer coating) on the hole transport layer 4 in a vacuum evaporation mode, wherein the thickness of the TCTA is 20nm, and the TCTA is an electron blocking layer 5;
a luminescent layer 6 is vapor-plated on the electron blocking layer 5, the main material is CBP, the doping material is Ir (ppy) 3, the mass ratio of the CBP to the Ir (ppy) 3 is 9:1, and the thickness is 30nm;
a hole blocking/electron transporting material TPBI is evaporated on the luminescent layer 6 in a vacuum evaporation mode, the thickness is 40nm, and the organic material of the layer is used as a hole blocking/electron transporting layer 7;
an electron injection layer LiF is vacuum evaporated on the hole blocking/electron transport layer 7, the thickness of the electron injection layer LiF is 1nm, and the electron injection layer is an electron injection layer 8;
on the electron injection layer 8, a cathode Al (100 nm) is vacuum-evaporated, and this layer is a cathode reflective electrode layer 9.
After the electroluminescent device was fabricated according to the above procedure, IVL data and light decay life of the device were measured, and the results are shown in table 4. The molecular structural formula of the related material is shown as follows:
Figure BDA0001673269600000231
TABLE 3
Figure BDA0001673269600000241
/>
Figure BDA0001673269600000251
TABLE 4
Figure BDA0001673269600000252
As can be seen from the device data results in table 4, the organic light emitting device of the present invention has a greater improvement in both efficiency and lifetime compared to OLED devices of known materials.
In order to compare the efficiency attenuation conditions of different devices under high current density, the efficiency attenuation coefficient is defined
Figure BDA0001673269600000254
It is shown that the drive current is 100mA/cm 2 The ratio between the difference between the maximum efficiency μ 100 of the device and the maximum efficiency μm of the device and the maximum efficiency, < > or >>
Figure BDA0001673269600000255
The larger the value, the more serious the efficiency roll-off of the device is, and conversely, the problem that the device rapidly decays under high current density is controlled. The efficiency attenuation factors->
Figure BDA0001673269600000256
The results of the measurement are shown in Table 5:
TABLE 5
Figure BDA0001673269600000253
/>
Figure BDA0001673269600000261
From the data in table 5, it can be seen from the comparison of the efficiency attenuation coefficients of the examples and the comparative examples that the organic light emitting device of the present invention can effectively reduce the efficiency roll-off.
Further, the efficiency of the OLED device prepared by the material of the invention is stable when the OLED device works at low temperature, and the efficiency test is carried out on the devices obtained in device examples 2, 5 and 11 and device comparative example 1 at the temperature range of-10-80 ℃, and the obtained results are shown in Table 6 and FIG. 2.
TABLE 6
Figure BDA0001673269600000262
As can be seen from the data in table 6 and fig. 2, device examples 2, 5, and 11 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1, the efficiency is high at low temperature, and the efficiency is smoothly increased during the temperature increase process.
In order to further test the beneficial effects produced by the compound of the present invention, the devices fabricated in device example 1 and device comparative example 1 of the present invention were tested for leakage current of reverse voltage, and the test data is shown in fig. 3, which shows that, as shown in fig. 3, the device fabricated in device example 1 and device comparative example 1 using the compound of the present invention has a smaller leakage current and a more stable current curve, so that the material of the present invention has a longer service life after being applied to device fabrication.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (3)

1. A compound with an alloplex and triarylamine structure as a core is characterized in that the specific structure of the compound is as follows:
Figure FDA0003956994620000011
any one of the above.
2. An organic electroluminescent device containing the compound of claim 1, wherein the hole transport layer of the organic electroluminescent device is a compound having an isoflexor and triarylamine structure as a core.
3. A lighting or display element comprising the organic electroluminescent device according to claim 2.
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