CN110323360B - Organic electroluminescent device and application thereof - Google Patents

Organic electroluminescent device and application thereof Download PDF

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CN110323360B
CN110323360B CN201910213669.1A CN201910213669A CN110323360B CN 110323360 B CN110323360 B CN 110323360B CN 201910213669 A CN201910213669 A CN 201910213669A CN 110323360 B CN110323360 B CN 110323360B
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陈海峰
李崇
张兆超
唐丹丹
庞羽佳
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Jiangsu Sunera Technology Co Ltd
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract

The invention belongs to the technical field of semiconductors, and particularly relates to a semiconductor deviceAn organic electroluminescent device and application thereof, comprising a cathode reflective electrode layer and an ITO anode layer, wherein at least one organic thin film layer is arranged between the cathode reflective electrode layer and the ITO anode layer, and the organic thin film layer contains a compound taking triaminobenzene as a core; the structure of the compound with the triaminobenzene as the core is shown as a general formula (1):
Figure DDA0002001337570000011
the compound takes the benzene as a core, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.

Description

Organic electroluminescent device and application thereof
Technical Field
The invention belongs to the technical field of semiconductors, and particularly relates to an organic electroluminescent device and application thereof.
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 like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices 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 photoelectric functional material of the OLED are required 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 transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission 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 transmission material, a light emitting material, an electron transmission 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 material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
The present invention provides an organic electroluminescent device and an application thereof to solve the above technical problems. The compound takes the benzene as a core, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme for solving the technical problems is as follows:
an organic electroluminescent device comprises a cathode reflective electrode layer and an ITO anode layer, wherein at least one organic thin film layer is arranged between the cathode reflective electrode layer and the ITO anode layer, and the organic thin film layer contains a compound taking triaminobenzene as a core; the structure of the compound with the triaminobenzene as the core is shown as a general formula (1):
Figure BDA0002001337550000031
in the general formula (1), Ar1、Ar2、Ar3、Ar4、Ar5、Ar6Are each independently represented by C1～C10Phenyl, unsubstituted or substituted by straight-chain or branched alkyl radicals, C1～C10Biphenyl, C, substituted or unsubstituted by a linear or branched alkyl radical1～C10One of a linear or branched alkyl substituted or unsubstituted naphthyl;
ar is1、Ar2、Ar3、Ar4、Ar5、Ar6Can also be expressed as a structure shown in the following general formula (2),
Figure BDA0002001337550000032
in the general formula (2), R1、R2、R3、R4、R5、R6、R7、R8Any one of them is a single bond, and the others are independently a hydrogen atom or C1～C10One of a linear or branched alkyl group;
x is O, S, C1～C10Methylene, C, substituted by linear or branched alkyl groups6～C15Methylene, C, substituted by aryl radicals6～C15One of the imino groups substituted by aryl.
Further, when Ar is1、Ar2、Ar3、Ar4、Ar5、Ar6In the case where not in the structure of the general formula (2), Ar1、Ar2、Ar3、Ar4、Ar5、Ar6At least two of them are represented by C1～C10A straight or branched alkyl substituted or unsubstituted biphenyl group having at least one C1～C10The straight or branched alkyl substituted or unsubstituted biphenyl group is not attached para; when Ar is1、Ar2、Ar3、Ar4、Ar5、Ar6When one or two of them are represented by the general formula (2), and X is C1～C10When methylene is substituted by a straight-chain or branched alkyl group, Ar1、Ar2、Ar3、Ar4、Ar5、Ar6At least one of them being C1～C10A straight or branched alkyl group substituted or unsubstituted biphenyl group, and C1～C10The straight or branched alkyl substituted or unsubstituted biphenyl group is not attached in the para position.
Further, Ar is1、Ar2、Ar3、Ar4、Ar5、Ar6Each independently selected from the following structures:
Figure BDA0002001337550000041
Figure BDA0002001337550000042
wherein R is9～R36Is shown as H, C1～C10Straight or branched chain alkyl.
Further, the triaminobenzene-based compound corresponds to any one of the following general formulae (3) to (7):
Figure BDA0002001337550000043
Figure BDA0002001337550000051
wherein R is37～R48Is shown as H, C1～C10Straight or branched chain alkyl.
Further, the specific compound of the general formula (1) has the structural formula:
Figure BDA0002001337550000052
Figure BDA0002001337550000061
Figure BDA0002001337550000071
Figure BDA0002001337550000081
Figure BDA0002001337550000091
Figure BDA0002001337550000101
Figure BDA0002001337550000111
Figure BDA0002001337550000121
Figure BDA0002001337550000131
Figure BDA0002001337550000141
Figure BDA0002001337550000142
any one of them.
Further, the preparation method of the compound taking triaminobenzene as the core comprises the following steps:
Figure BDA0002001337550000143
weighing intermediate M and intermediate N, dissolving with toluene, and adding Pd2(dba)3Triphenylphosphine and potassium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 90-110 ℃ for 10-24 hours under the inert atmosphere, cooling, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target compound; the dosage of the toluene is 30-50mL of toluene used per gram of the intermediate M; the molar ratio of the intermediate N to the intermediate M is 1 (1.0-1.5); the Pd2(dba)3The molar ratio of the sodium tert-butoxide to the intermediate M is (2.0-3.0): 1; the molar ratio of the triphenylphosphine to the intermediate M is (2.0-3.0): 1.
Further, the organic thin film layer includes a hole transport layer.
The invention also provides a display element comprising the organic electroluminescent device.
The invention has the beneficial effects that:
1. the compound is a pyromellitic compound, and the branched chain comprises a triarylamine structure, so that the compound has strong hole transport capacity and high hole mobility, can be used as a hole transport material, and the high hole transport rate can improve the efficiency of an organic electroluminescent device; under a proper LUMO energy level, the organic electroluminescent device also plays a role in blocking electrons, improves the recombination efficiency of excitons in a light-emitting layer, reduces the efficiency roll-off under high current density, reduces the voltage of the device, improves the current efficiency of the device and prolongs the service life of the device.
2. The compound takes the benzene as the center, 3 connected branched chains are radial, and after the material is formed into a film, all the branched chains can be mutually crossed to form a high-compactness film layer, so that the leakage current of the material after the application of an OLED device is reduced, and the service life of the device is prolonged.
3. When the compound is applied to an OLED device, the structure of the device is optimized, so that high film stability can be kept, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.
4. The compound provided by the invention has higher glass transition temperature and molecular thermal stability, appropriate HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
fig. 2 is a graph of current efficiency versus temperature.
Fig. 3 is a graph showing reverse voltage leakage current test curves of the devices manufactured in example 1 and comparative example 1.
In the drawings, the components represented by the respective reference numerals are listed below:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, first hole transport layer, 5, second hole transport layer, 6, luminescent layer, 7, electron transport layer, 8, electron injection layer, 9, cathode reflection electrode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1:
synthesis of intermediate N
Figure BDA0002001337550000161
Weighing raw material I and raw material II, dissolving with toluene, and adding Pd2(dba)3Triphenylphosphine and potassium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 90-110 ℃ for 10-24 hours under the inert atmosphere, cooling, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a target compound; the molar ratio of the raw material I to the raw material II is 1 (1.0-1.5); pd2(dba)3The molar ratio of the sodium tert-butoxide to the raw material I is (0.006-0.02) to 1, and the molar ratio of the sodium tert-butoxide to the raw material I is (2.0-3.0) to 1; the molar ratio of triphenylphosphine to the raw material I is (2.0-3.0): 1; 50-100mL of toluene were added to 1g of starting material I.
Synthesis example of intermediate N-1:
Figure BDA0002001337550000162
a250 ml three-neck flask was charged with 0.01mol of 1-aniline, 0.012mol of 2-bromobiphenyl, 0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen gas-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 12 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate N-1; elemental analysis Structure (molecular formula C)18H15N): theoretical value C, 88.13; h, 6.16; n, 5.71; test values are: c, 88.12; h, 6.16; and N, 5.72. ESI-MS (M/z) (M)+): theoretical value is 245.12, found 245.88.
Intermediate N-2, intermediate N-3, intermediate N-4, intermediate N-5 and intermediate N-6 were prepared according to the procedure for the preparation of intermediate N-1 in example 1, using the following substitution of starting materials as shown in Table 1 below:
TABLE 1
Figure BDA0002001337550000163
Figure BDA0002001337550000171
Preparation of intermediate Ar according to the procedure for preparation of intermediate N1And Ar2。
Synthesis of intermediate M
Figure BDA0002001337550000181
Weighing raw material III and intermediate Ar1Dissolving in toluene, adding Pd2(dba)3Triphenylphosphine and potassium tert-butoxide; under inert atmosphere, the mixed solution of the reactants is put at the reaction temperatureReacting at 90-110 ℃ for 10-24 hours, cooling, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate A; the molar ratio of the raw material III to the intermediate Ar1 is 1 (1.0-1.5); pd2(dba)3The molar ratio of the sodium tert-butoxide to the raw material III is (0.006-0.02) to 1, and the molar ratio of the sodium tert-butoxide to the raw material III is (2.0-3.0) to 1; the molar ratio of triphenylphosphine to the raw material III is (2.0-3.0): 1; 50-100mL of toluene were added to 1g of starting material III.
Weighing intermediate A and intermediate Ar2, dissolving with toluene, and adding Pd2(dba)3Triphenylphosphine and potassium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 90-110 ℃ for 10-24 hours under the inert atmosphere, cooling, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate M; the molar ratio of the intermediate A to the intermediate Ar2 is 1 (1.0-1.5); pd2(dba)3The molar ratio of the intermediate A to the intermediate A is (0.006-0.02) to 1, and the molar ratio of the sodium tert-butoxide to the intermediate A is (2.0-3.0) to 1; the molar ratio of triphenylphosphine to intermediate A is (2.0-3.0): 1; 1g of intermediate A was added to 50-100mL of toluene.
Synthesis example of intermediate M-1:
Figure BDA0002001337550000182
a250 ml three-necked flask was charged with 0.01mol of the starting material III, 0.012mol of intermediate Ar1-1, 0.03mol of potassium tert-butoxide, and 1X 10 under a nitrogen atmosphere-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 12 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate A-1; elemental analysis Structure (molecular formula C)18H13Br2N): theoretical value C, 53.63; h, 3.25; br, 39.64; n, 3.47; test values are: c, 53.62; h, 3.25; br, 39.65; and N, 3.47. ESI-MS (M/z) (M)+): theoretical value is 400.94, found 401.80.
A250 ml three-necked flask was charged with 0.01mol of intermediate A-1, 0.012mol of intermediate Ar2-1, 0.03mol of tert-butyl under an atmosphere of nitrogen gasPotassium butoxide, 1X 10-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine (mol) and 150mL of toluene for 12 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate M-1; elemental analysis Structure (molecular formula C)36H27BrN2): theoretical value C, 76.19; h, 4.80; br, 14.08; n, 4.94; test values are: c, 76.19; h, 4.80; br, 14.09; and N, 4.93. ESI-MS (M/z) (M)+): theoretical value is 566.14, found 566.91.
Intermediate M-2, intermediate M-3, intermediate M-4, intermediate M-5, intermediate M-6 and intermediate M-7 were prepared according to the procedure described above for intermediate M-1, using the following starting materials in the following Table 2 instead:
TABLE 2
Figure BDA0002001337550000191
Figure BDA0002001337550000201
Example 2: synthesis of Compound 6:
Figure BDA0002001337550000202
a250 mL three-necked flask was charged with 0.01mol of intermediate M-1, 0.012mol of intermediate N-1, 0.03mol of potassium tert-butoxide, and 1X 10 under a nitrogen atmosphere-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150ml toluene for 12 hr, sampling the sample, and reacting completely; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain a compound 9; elemental analysis Structure (molecular formula C)54H41N3): theoretical value C, 88.61; h, 5.65; n, 5.74; test values are: c, 88.62; h, 5.65; n, 5.73. ESI-MS (M/z) (M)+): theoretical value is 731.33, found 731.66.
Example 3: synthesis of compound 18:
Figure BDA0002001337550000211
compound 18 is prepared as in example 2, except that intermediate M-2 is substituted for intermediate M-1 and intermediate N-2 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)66H49N3): theoretical value C, 89.66; h, 5.59; n, 4.75; test values are: c, 89.67; h, 5.59; n, 4.74. ESI-MS (M/z) (M)+): theoretical value is 883.39, found 883.57.
Example 4: synthesis of compound 27:
Figure BDA0002001337550000212
compound 27 can be prepared as in example 2, except that intermediate M-2 is substituted for intermediate M-1 and intermediate N-3 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)58H43N3): theoretical value C, 89.08; h, 5.54; n, 5.37; test values are: c, 89.07; h, 5.54; n, 5.38. ESI-MS (M/z) (M)+): theoretical value is 781.35, found 781.74.
Example 5: synthesis of compound 40:
Figure BDA0002001337550000213
compound 40 is prepared as in example 2, except that intermediate M-3 is substituted for intermediate M-1 and intermediate N-4 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)63H49N3): theoretical value C, 89.22; h, 5.82; n, 4.95; test values are: c, 89.23; h, 5.82; and N, 4.95. ESI-MS (M/z) (M)+): theoretical value is 847.39, found 847.85.
Example 6: synthesis of compound 54:
Figure BDA0002001337550000221
compound 54 is prepared as in example 2, except that intermediate M-4 is substituted for intermediate M-1 and intermediate N-5 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)66H53N3): theoretical value C, 89.25; h, 6.02; n, 4.73; test values are: c, 89.24; h, 6.02; n, 4.74. ESI-MS (M/z) (M)+): theoretical value is 887.42, found 887.64.
Example 7: synthesis of compound 72:
Figure BDA0002001337550000222
compound 72 is prepared as in example 2, except that intermediate M-5 is substituted for intermediate M-1 and intermediate N-5 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)61H47N3): theoretical value C, 89.13; h, 5.76; n, 5.11; test values are: c, 89.12; h, 5.76; and N, 5.12. ESI-MS (M/z) (M)+): theoretical value is 821.38, found 821.71.
Example 8: synthesis of compound 90:
Figure BDA0002001337550000223
compound 90 is prepared as in example 2, except that intermediate M-6 is substituted for intermediate M-1 and intermediate N-5 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)70H55N3): theoretical value C, 89.61; h, 5.91; n, 4.48; test values are: c, 89.62; h, 5.91; and N, 4.47. ESI-MS (M/z) (M)+): theoretical value is 937.44, found 937.69.
Example 9: synthesis of compound 111:
Figure BDA0002001337550000231
compound 111 can be prepared as in example 2, except that intermediate M-7 is substituted for intermediate M-1 and intermediate N-6 is substituted for intermediate N-1; elemental analysis Structure (molecular formula C)63H47N3O): theoretical value C, 87.77; h, 5.50; n, 4.87; o, 1.86; test values are: c, 87.78; h, 5.50; n, 4.87; o, 1.85. ESI-MS (M/z) (M)+): theoretical value is 861.37, found 861.83.
The organic compound of the present invention is used in a light-emitting device, and can be used as a hole transport layer material. The T1 energy level, thermal property, and HOMO energy level were measured for compounds 6, 18, 27, 40, 54, 72, 90, 111, 156, 162, 171, 180, 201, 233, and 252 of the present invention, respectively, and the results are shown in table 3.
TABLE 3
Figure BDA0002001337550000232
Figure BDA0002001337550000241
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of (4); the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in an atmospheric environment.
The data in the table show that the organic compound has a proper HOMO energy level and can be applied to a hole transport layer, and the organic compound taking the pyromellitic dianhydride as the core has a higher triplet state energy level and higher thermal stability, so that the efficiency and the service life of the manufactured OLED device containing the organic compound are improved.
Preparing a device:
the effect of the use of the synthesized compound of the present invention as a material for a hole transport layer and an electron blocking layer in a device is explained in detail below by device examples 1 to 17 and device comparative example 1. Device examples 2 to 17 and device comparative example 1 compared with device example 1, 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 and the electron blocking layer were 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
Device examples used ITO as the anode, Al as the cathode, CBP and Ir (ppy)3The materials are mixed and doped according to the weight ratio of 90:10 to be used as a light-emitting layer material, HAT-CN is used as a hole injection layer material, the compound 6 prepared in the embodiment of the invention is used as a hole transport layer and an electron blocking layer material, 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:
a) 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; b) 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; c) evaporating a second hole transport layer material NPB on the hole injection layer 3 in a vacuum evaporation mode, wherein the thickness of the second hole transport layer material NPB is 60nm, and the second hole transport layer material NPB is a second hole transport layer 4; d) on the second hole transport layer 4, a first hole transport layer material, a compound 6 prepared in the embodiment of the present invention, is evaporated by vacuum evaporation, the thickness of which is 20nm, and the layer is a first hole transport layer 5; e) a luminescent layer 6 is vapor-deposited on the first hole transport layer 5, the main material is CBP, the doping material is Ir (ppy)3CBP and Ir (ppy)3The mass ratio of (1) to (9) is 30 nm; f) 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; g) in the skyVacuum evaporation of an electron injection layer LiF with the thickness of 1nm is carried out on the hole blocking/electron transport layer 7, and the layer is an electron injection layer 8; h) on the electron injection layer 8, cathode Al (100nm) was vacuum-evaporated, and this layer was 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 BDA0002001337550000251
device examples 2-17 and comparative example 1
The device of device examples 2 to 17 and comparative example 1 were completely the same as those of device example 1 in terms of the manufacturing process, and the same substrate material and electrode material were used, and the film thickness of the electrode material was kept the same, except that the material used for the hole transporting/electron blocking layer was different. See table 4 for specific data.
TABLE 4
Figure BDA0002001337550000261
Figure BDA0002001337550000271
The efficiency and lifetime data for each of the examples and comparative examples are shown in table 5.
TABLE 5
Figure BDA0002001337550000272
Figure BDA0002001337550000281
It can be seen from the device data results of table 5 that the organic light emitting device of the present invention achieves a greater improvement in driving voltage, efficiency, and lifetime over OLED devices of known materials.
In order to compare the efficiency attenuation of different devices under high current density, the efficiency attenuation coefficient phi is defined and expressed, and the efficiency attenuation coefficient phi represents that the driving current is 100mA/cm2The larger the phi value is, the more serious the efficiency roll-off of the device is, and otherwise, the problem of rapid attenuation of the device under high current density is controlled. The attenuation coefficient of efficiency phi was measured for each of the device examples 1 to 17 and comparative example 1, and the results are shown in Table 6:
TABLE 6
Figure BDA0002001337550000282
Figure BDA0002001337550000291
From the data in table 6, it can be seen from the comparison of the efficiency roll-off 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 is stable when the OLED device works at low temperature, the efficiency test is carried out on the device examples 1, 4 and 8 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 7 and the figure 2.
TABLE 7
Figure BDA0002001337550000292
Figure BDA0002001337550000301
As can be seen from the data in table 7 and fig. 2, device examples 1, 4, and 8 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 steadily increased during the temperature increase process.
In order to further test the beneficial effects of the compound of the present invention, the devices fabricated in the device example 1 and the device comparative example 1 were tested for leakage current under reverse voltage, and the test data is shown in fig. 3, which is a graph showing that, as shown in fig. 3, the device example 1 using the compound of the present invention has a smaller leakage current and a more stable current curve than the device fabricated in the device comparative example 1, so that the material of the present invention has a longer service life after being applied to the 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 (4)

1. An organic electroluminescent device is characterized by comprising a cathode reflective electrode layer and an ITO anode layer, wherein at least one organic thin film layer is arranged between the cathode reflective electrode layer and the ITO anode layer, and the organic thin film layer contains a compound taking triaminobenzene as a core; the structure of the compound with the triaminobenzene as the core is shown as a general formula (5):
Figure FDA0002722137030000011
in the general formula (5), Ar is1、Ar2、Ar3、Ar4、Ar5Each independently selected from the following structures:
Figure FDA0002722137030000012
wherein R is9～R18、R22～R24、R45～R48Is shown as H, C1～C10Straight or branched chain alkyl.
2. The organic electroluminescent device according to claim 1, wherein the specific compound of the formula (5) has the structural formula:
Figure FDA0002722137030000013
Figure FDA0002722137030000021
Figure FDA0002722137030000031
Figure FDA0002722137030000041
Figure FDA0002722137030000051
Figure FDA0002722137030000061
Figure FDA0002722137030000062
any one of them.
3. The organic electroluminescent device as claimed in claim 1, wherein the organic thin film layer comprises an ITO anode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode reflective electrode layer, the hole transport layer comprises a first hole transport layer and a second hole transport layer, and the first hole transport layer or the second hole transport layer contains a compound with triaminobenzene as a core.
4. A display element comprising the organic electroluminescent device according to any one of claims 1 to 3.
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