CN110577510B - Compound based on bis-dimethyl fluorene substituted aniline and organic electroluminescent device prepared from compound - Google Patents

Compound based on bis-dimethyl fluorene substituted aniline and organic electroluminescent device prepared from compound Download PDF

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CN110577510B
CN110577510B CN201910332387.3A CN201910332387A CN110577510B CN 110577510 B CN110577510 B CN 110577510B CN 201910332387 A CN201910332387 A CN 201910332387A CN 110577510 B CN110577510 B CN 110577510B
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hole transport
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CN110577510A (en
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李崇
赵四杰
张兆超
徐浩杰
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound based on bis-dimethyl fluorene substituted aniline and an organic electroluminescent device prepared from the compound. The compound is used as HIT or EB material to be applied to an organic electroluminescent device, and the luminescent device using the compound has good photoelectric performance and can better adapt to and meet the application requirements of panel manufacturing enterprises.

Description

Compound based on bis-dimethyl fluorene substituted aniline and organic electroluminescent device prepared from compound
Technical Field
The invention relates to the technical field of semiconductors, in particular to an arylamine compound containing bisdimethylfluorene in a 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 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
In view of the above problems in the prior art, the applicant of the present invention provides a compound based on bis (dimethylfluorene) substituted aniline and an organic electroluminescent device prepared from the compound. The compound contains a structure of poly-substituted aniline connected with bisdimethylfluorene, 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 optimization of the device structure.
The technical scheme of the invention is as follows:
a compound based on bis-dimethyl fluorene substituted aniline has a structure shown as a general formula (I):
Figure BDA0002038115290000021
wherein R is1Represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl and substituted or unsubstituted carbazolinyl; m represents a number 1 or 2;
l represents one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluorenyl, and a substituted or unsubstituted dibenzofuranylene;
r represents a structure shown in a general formula (II), a general formula (III) or a general formula (IV):
Figure BDA0002038115290000031
in the general formula (II), X represents an oxygen atom, a sulfur atom, a selenium atom, -C (R)4)(R5)-、-N(R6) -or-Si (R)7)(R8)-；R4～R8Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl and pyrazinyl; r4And R5、R7And R8Can be bonded to each other to form a ring;
in the general formula (II) and the general formula (III), Z is represented by CH or N, which may be the same or different at each occurrence;
in the case of bonding of the general formula (II) and L, Z represents a carbon atom;
in the general formula (IV), R2、R3Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl and substituted or unsubstituted carbazolinyl;
the substituent is halogen, cyano, C1-10An alkyl group.
The preferred specific structural formula of the compound based on the bis-dimethyl fluorene substituted aniline is as follows:
Figure BDA0002038115290000032
Figure BDA0002038115290000041
Figure BDA0002038115290000051
Figure BDA0002038115290000061
Figure BDA0002038115290000071
Figure BDA0002038115290000081
Figure BDA0002038115290000091
Figure BDA0002038115290000101
Figure BDA0002038115290000111
Figure BDA0002038115290000121
Figure BDA0002038115290000131
Figure BDA0002038115290000132
any one of the above.
An organic electroluminescent device comprising at least one functional layer containing the compound based on bisdimethylfluorene-substituted aniline.
The functional layer is a light-emitting layer and/or an electron blocking layer and/or a hole injection layer and/or a hole transport layer.
A lighting or display element comprising the organic electroluminescent device.
The beneficial technical effects of the invention are as follows:
1. the compound contains a structure of poly-substituted aniline connected with bisdimethylfluorene, 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 prolong the service life of the OLED device through optimization of the device structure.
2. The compound is an organic light-emitting functional layer material, the material has the characteristics of difficult intermolecular crystallization, difficult aggregation and good film forming property, and the rigid group in the molecule of the compound can improve the thermal stability of the material.
3. The compound structure of the invention ensures that the distribution of electrons and holes in the luminescent layer is more balanced, and under the proper HOMO energy level, the hole injection/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 light-emitting layer.
4. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
Drawings
FIG. 1 is a schematic diagram of the application of the compounds of the present invention to an OLED device;
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 luminescent layer, 7 is an electron transport layer, 8 is an electron injection layer, and 9 is a cathode reflection electrode layer.
FIG. 2 shows the current efficiencies of the OLED devices of the embodiment of the present invention and the OLED device of the comparative example 1 at the temperature range of-10 to 80 ℃.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
Synthesis of intermediates
Preparation of intermediate C-1
Figure BDA0002038115290000141
In a 500ml three-necked flask, 0.05mol of the raw material A-1 and 0.05mol of the raw material B-1 were placed under a nitrogen atmosphere, and a mixed solvent (300ml of toluene and 90ml of H) was added2O) dissolving it, introducing nitrogen, stirring for 1 hour, and adding 0.1mol of K2CO3、0.005mol Pd(PPh3)4The reaction was heated to 90 ℃ for 8 hours, and the reaction was observed by Thin Layer Chromatography (TLC) until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and decompressing the organic phaseRotary evaporation to no distillate. The resulting material was purified by silica gel column to give intermediate C-1 in 99.4% purity and 87% yield.
Elemental analysis Structure (molecular formula C)24H15BrO): theoretical value C, 72.19; h, 3.79; br, 20.01; o, 4.01; test values are: c, 72.16; h, 3.77; br, 20.04; and O, 4.03.
ESI-MS (M/z) (M +): theoretical value is 399.29, found 399.47.
Preparation of intermediate C-2
Figure BDA0002038115290000151
The procedure for the synthesis of intermediate C-2 is similar to that of intermediate C-1 except that compound B-1 is replaced with compound B-2;
elemental analysis Structure (molecular formula C)30H19BrO): theoretical value C, 75.80; h, 4.03; br, 16.81; o, 3.37; test values are: c, 75.78; h, 4.05; br, 16.79; and O, 3.39.
ESI-MS (M/z) (M +): theoretical value is 475.38, found 475.16.
Preparation of intermediate C-3
Figure BDA0002038115290000152
The procedure for the synthesis of intermediate C-3 is similar to that of intermediate C-1 except that compound B-1 is replaced with compound B-3;
elemental analysis Structure (molecular formula C)30H19BrO): theoretical value C, 75.80; h, 4.03; br, 16.81; o, 3.37; test values are: c, 75.78; h, 4.04; br, 16.79; and O, 3.40.
ESI-MS (M/z) (M +): theoretical value is 475.38, found 475.04.
Preparation of intermediate C-4
Figure BDA0002038115290000161
The procedure for the synthesis of intermediate C-4 is similar to that of intermediate C-1 except that compound A-1 is replaced with compound A-2 and compound B-1 is replaced with compound B-4;
elemental analysis Structure (molecular formula C)27H21Br): theoretical value C, 76.24; h, 4.98; br, 18.78; test values are: c, 76.22; h, 5.01; br, 18.77.
ESI-MS (M/z) (M +): theoretical value is 425.37, found 425.09.
Preparation of intermediate C-5
Figure BDA0002038115290000162
The procedure for the synthesis of intermediate C-5 is similar to that of intermediate C-4 except that compound A-2 is replaced with compound A-3;
elemental analysis Structure (molecular formula C)30H20BrN): theoretical value C, 75.95; h, 4.25; br, 16.84; n, 2.95; test values are: c, 75.93; h, 4.25; br, 16.83; and N, 2.98.
ESI-MS (M/z) (M +): theoretical value is 474.40, found 474.18.
Preparation of intermediate C-6
Figure BDA0002038115290000163
In a 500ml three-necked flask, 0.005mol of the raw material A-4, 0.006mol of the raw material B-4, 0.01mol of sodium tert-butoxide, 3X 10-4mol Pd(dba)2And 1.2X 10-3And (3) adding 60ml of toluene to dissolve the tri-tert-butylphosphine, heating to reflux, reacting for 4 hours, and observing the reaction by TLC until the reaction is complete. And naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction is obtained. The resulting material was purified by silica gel column to give intermediate C-6 in 99.8% purity and 86% yield.
Element classificationStructure (molecular formula C)24H16BrN): theoretical value C, 72.37; h, 4.05; br, 20.06; n, 3.52; test values are: c, 72.34; h, 4.07; br, 20.04; and N, 3.55.
ESI-MS (M/z) (M +): theoretical value is 398.30, found 398.92.
Preparation of intermediate C-7
Figure BDA0002038115290000171
The procedure for the synthesis of intermediate C-7 is similar to that of intermediate C-1 except that compound A-1 is replaced with compound A-5;
elemental analysis Structure (molecular formula C)30H20BrN): theoretical value C, 75.95; h, 4.25; br, 16.84; n, 2.95; test values are: c, 75.92; h, 4.27; br, 16.82; and N, 2.98.
ESI-MS (M/z) (M +): theoretical value is 474.40, found 473.86.
Preparation of intermediate C-8
Figure BDA0002038115290000172
The procedure for the synthesis of intermediate C-8 is similar to that of intermediate C-6 except that compound B-4 is replaced with compound B-5;
elemental analysis Structure (molecular formula C)30H18BrNO): theoretical value C, 73.78; h, 3.72; br, 16.36; n, 2.87; o, 3.28; test values are: c, 73.75; h, 3.73; br, 16.35; n, 2.89; and O, 3.29.
ESI-MS (M/z) (M +): theoretical value is 488.38, found 487.69.
Preparation of intermediate C-9
Figure BDA0002038115290000181
The procedure for the synthesis of intermediate C-9 is similar to that of intermediate C-4 except that compound A-2 is replaced with compound A-6;
elemental analysis Structure (molecular formula C)30H21Br): theoretical value C, 78.09; h, 4.59; br, 17.32; test values are: c, 78.07; h, 4.62; br, 17.31.
ESI-MS (M/z) (M +): theoretical value is 461.40, found 460.29.
Preparation of intermediate C-10
Figure BDA0002038115290000182
The procedure for the synthesis of intermediate C-10 is similar to that of intermediate C-4 except that compound A-2 is replaced with compound A-7;
elemental analysis Structure (molecular formula C)24H15BrO): theoretical value C, 72.19; h, 3.79; br, 20.01; o, 4.01; test values are: c, 72.17; h, 3.81; br, 20.00; and O, 4.02.
ESI-MS (M/z) (M +): theoretical value is 399.29, found 400.18.
Preparation of intermediate C-11
Figure BDA0002038115290000183
The procedure for the synthesis of intermediate C-11 is similar to that of intermediate C-4 except that compound A-2 is replaced with compound A-8;
elemental analysis Structure (molecular formula C)23H14BrNO): theoretical value C, 69.02; h, 3.53; br, 19.96; n, 3.50; o, 4.00; test values are: c, 69.00; h, 3.54; br, 19.94; n, 3.52; and O, 4.01.
ESI-MS (M/z) (M +): theoretical value is 400.28, found 400.86.
Preparation of intermediate C-12
Figure BDA0002038115290000191
The procedure for the synthesis of intermediate C-12 is similar to that of intermediate C-1 except that compound A-1 is replaced with compound A-9 and compound B-1 is replaced with compound B-6;
elemental analysis Structure (molecular formula C)29H18BrNO): theoretical value C, 73.12; h, 3.81; br, 16.77; n, 2.94; o, 3.36; test values are: c, 73.09; h, 3.82; br, 16.75; n, 2.96; and O, 3.38.
ESI-MS (M/z) (M +): theoretical value is 476.37, found 475.86.
Preparation of intermediate C-13
Figure BDA0002038115290000192
The procedure for the synthesis of intermediate C-13 is similar to that of intermediate C-1 except that compound A-1 is replaced with compound A-10;
elemental analysis Structure (molecular formula C)29H19BrN2): theoretical value C, 73.27; h, 4.03; br, 16.81; n, 5.89; test values are: c, 73.25; h, 4.05; br, 16.80; and N, 5.90.
ESI-MS (M/z) (M +): theoretical value is 475.39, found 474.86.
Preparation of intermediate C-14
Figure BDA0002038115290000193
The procedure for the synthesis of intermediate C-14 is similar to that of intermediate C-4 except that compound A-2 is replaced with compound A-11;
elemental analysis Structure (molecular formula C)29H20BrN): theoretical value C, 75.33; h, 4.36; br, 17.28; n, 3.03; test values are: c, 75.31; h, 4.37; br, 17.27; and N, 3.05.
ESI-MS (M/z) (M +): theoretical value is 462.39, found 461.58.
Preparation of intermediate C-15
Figure BDA0002038115290000201
The procedure for the synthesis of intermediate C-15 is similar to that of intermediate C-1 except that compound A-1 is replaced with compound A-12;
elemental analysis Structure (molecular formula C)35H23BrN2): theoretical value C, 76.23; h, 4.20; br, 14.49; n, 5.08; test values are: c, 76.21; h, 4.22; br, 14.48; and N, 5.09.
ESI-MS (M/z) (M +): theoretical value is 551.49, found 550.37.
Example 1: synthesis of Compound 3
Figure BDA0002038115290000202
To a 500ml three-necked flask, 0.005mol of the prepared intermediate C-1, 0.006mol of the starting material D, 0.01mol of sodium tert-butoxide, 3X 10-4molPd(dba)2And 1.2X 10-3And (3) adding 60ml of toluene to dissolve the tri-tert-butylphosphine, heating to reflux, reacting for 4 hours, and observing the reaction by TLC until the reaction is complete. And naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction is obtained. The resulting material was purified by silica gel column to give the title target product in 99.7% purity and 81% yield.
Elemental analysis Structure (molecular formula C)54H41NO): theory C, 90.09; h, 5.74; n, 1.95; o, 2.22; test values are: c, 90.06; h, 5.72; n, 1.98; o, 2.24.
ESI-MS(m/z)(M+): theoretical value is 719.93, found 720.27.
The procedure of example 1 was repeated to prepare the following compounds, except that intermediate C as listed in table 1 below was used:
TABLE 1
Figure BDA0002038115290000211
Figure BDA0002038115290000221
Figure BDA0002038115290000231
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 thermal properties and HOMO levels of compounds 3, 9, 33, 34, 44, 54, 71, 79, 82, 99, 111, 124, 162, 166, 176, 232, 241, 246, 260, and 262 of the present invention were measured, and the results are shown in table 2.
TABLE 2
Figure BDA0002038115290000232
Figure BDA0002038115290000241
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 different HOMO energy levels and can be applied to different functional layers, and the compound based on the polysubstituted aniline-grafted bisdimethylfluorene has 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.
The application effect of the synthesized OLED material in the device is explained in detail through device examples 1-20 and device comparative example 1. Compared with the device embodiment 1, the device embodiments 2-20 and the device comparative example 1 have the same manufacturing process, adopt the same substrate material and electrode material, keep the film thickness of the electrode material consistent, and are different in that the hole transport layer material or the electron blocking layer material in the device is replaced. The current efficiency, color and LT95 lifetime test results at 5000nit luminance of the devices obtained in each example are shown in table 3. Efficiency attenuation coefficient of the resulting device
Figure BDA0002038115290000242
The test results of (2) are shown in Table 4. The current test results of the resulting devices are shown in table 5.
Device example 1
Transparent glass is used as a substrate layer 1, ITO with a thickness of 150nm is coated thereon as an anode layer 2, which is washed, i.e., sequentially subjected to alkali washing, pure water washing, and then drying, and then subjected to ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the washed ITO anode layer 2, HAT-CN having a thickness of 10nm was deposited as a hole injection layer 3 by a vacuum deposition apparatus. The compound 3 prepared in preparation example 1 was then evaporated to a thickness of 60nm as a hole transport layer 4. EB-1 was then deposited as an electron blocking layer 5 with a thickness of 20 nm. And then, carrying out vacuum evaporation on the electron blocking layer to obtain a light-emitting layer 6 with the thickness of 30nm, wherein the light-emitting layer uses host materials GH-1 and GH-2 and doping materials GD-1, and the mass ratio of GH-1, GH-2 and GD-1 is 45:45: 10. Then, ET-1 and Liq having a thickness of 40nm were successively vacuum-evaporated on the light-emitting layer as the electron transporting layer 7, and the mass ratio of ET-1 to Liq was 1: 1. Then, lithium fluoride (LiF) having a thickness of 1nm was vacuum-deposited on the electron transport layer as the electron injection layer 8. Finally, aluminum (Al) with a thickness of 100nm was vacuum-evaporated on the electron injection layer as the cathode layer 9. The molecular structural formula of the related material is shown as follows:
Figure BDA0002038115290000251
device example 2
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used compound 9 prepared in preparation example 2 as a hole transport material.
Device example 3
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 33 prepared in preparation example 3 as a hole transport material.
Device example 4
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used compound 34 prepared in preparation example 4 as a hole transport material.
Device example 5
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 44 prepared in preparation example 5 as a hole transport material.
Device example 6
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 54 prepared in preparation example 6 as a hole transport material.
Device example 7
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 71 prepared in preparation example 7 as a hole transport material.
Device example 8
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 79 prepared in preparation example 8 as a hole transport material.
Device example 9
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 82 prepared in preparation example 9 as a hole transport material.
Device example 10
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 99 prepared in preparation example 10 as a hole transport material.
Device example 11
The procedure of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material; electron blocking layer 5 the compound 111 prepared in preparation example 11 was used as an electron blocking material.
Device example 12
The procedure of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material; electron blocking layer 5 the compound 124 prepared in preparation example 12 was used as an electron blocking material.
Device example 13
The procedure of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material; electron blocking layer 5 the compound 162 prepared in preparation example 13 was used as an electron blocking material.
Device example 14
The procedure of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material; electron blocking layer 5 the compound 166 prepared in preparation example 14 was used as an electron blocking material.
Device example 15
The procedure of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material; electron blocking layer 5 the compound 176 prepared in preparation example 15 was used as an electron blocking material.
Device example 16
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 232 prepared in preparation example 16 as a hole transport material.
Device example 17
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 241 prepared in preparation example 17 as a hole transport material.
Device example 18
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 246 prepared in preparation example 18 as a hole transport material.
Device example 19
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 260 prepared in preparation example 19 as a hole transport material.
Device example 20
The procedure of device example 1 described above was repeated except that the hole transport layer 4 used the compound 262 prepared in preparation example 20 as a hole transport material.
Device comparative example 1
The process of device example 1 above was repeated except that hole transport layer 4 used HT-1 as the hole transport material.
TABLE 3
Figure BDA0002038115290000271
Figure BDA0002038115290000281
Note: the life test system is an OLED device life tester which is researched by the owner of the invention together with Shanghai university.
As can be seen from the results in table 3, compared with comparative example 1, the OLED device prepared by the embodiment of the present invention has a great improvement in both efficiency and lifetime, and particularly, the driving lifetime of the device is greatly improved.
TABLE 4
Figure BDA0002038115290000282
The results in table 4 show that, compared with comparative example 1, the OLED device manufactured in the embodiment of the present invention has a relatively gentle efficiency roll-off trend at a high current density, and provides a good prospect for industrialization.
Table 5 shows the current efficiency test results of the OLED devices of device examples 1, 10 and 15 and comparative example 1 at the interval of-10 to 80 ℃.
TABLE 5
Figure BDA0002038115290000291
The results of table 5 are plotted as figure 2. As can be seen from table 5 and fig. 2, the OLED device according to the embodiment of the present invention has not only high low-temperature efficiency but also a smooth increase in efficiency during a temperature increase, as compared to comparative example 1.
Finally, the above embodiments are only used to illustrate the technical solution of the present invention and are not limited. Modifications and equivalents of the present invention may be made by those skilled in the art without departing from the spirit and scope of the present invention, and are intended to be included within the scope of the appended claims.

Claims (5)

1. A compound based on bis-dimethyl fluorene substituted aniline is characterized in that the specific structural formula of the compound is as follows:
Figure FDA0003286520910000011
Figure FDA0003286520910000021
Figure FDA0003286520910000031
Figure FDA0003286520910000041
Figure FDA0003286520910000042
any one of the above.
2. An organic electroluminescent device comprising at least one functional layer containing the compound based on bisdimethylfluorene-substituted aniline according to claim 1.
3. The organic electroluminescent device according to claim 2, characterized in that the functional layer is a light-emitting layer and/or an electron blocking layer and/or a hole injection layer and/or a hole transport layer.
4. An organic electroluminescent device comprising an electron blocking layer containing a compound represented by:
Figure FDA0003286520910000051
5. a lighting or display element, characterized in that the element comprises an organic electroluminescent device as claimed in claim 2 or 3.
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KR20200122116A (en) 2019-04-17 2020-10-27 엘지디스플레이 주식회사 Novel compound and organic light emitting device
CN112552225B (en) * 2019-09-26 2023-09-05 江苏三月科技股份有限公司 Triarylamine organic compound with carbazole as core and application thereof
CN112778253B (en) * 2019-11-07 2024-02-09 北京鼎材科技有限公司 Organic compound and organic electroluminescent device containing the same
US20220246848A1 (en) * 2020-01-23 2022-08-04 Lg Chem, Ltd. Organic light emitting device
CN113416164B (en) * 2020-04-28 2022-04-19 江苏三月科技股份有限公司 Carbazole-containing organic compound and application thereof
CN111440156A (en) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
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CN112194612A (en) * 2020-10-15 2021-01-08 濮阳惠成电子材料股份有限公司 Synthesis method of photoelectric material intermediate N- (7-bromo-9, 9-dimethylfluorene-2-yl) carbazole
US20240083836A1 (en) * 2020-12-18 2024-03-14 Merck Patent Gmbh Materials for electronic devices
CN112961134B (en) * 2021-02-04 2023-04-07 吉林奥来德光电材料股份有限公司 Organic light-emitting auxiliary layer material, preparation method and application thereof, and organic electroluminescent device
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110386894A (en) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 A kind of hole mobile material and its application

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106688119B (en) * 2014-07-09 2019-07-23 保土谷化学工业株式会社 Organic electroluminescence device
KR102307238B1 (en) * 2014-12-26 2021-10-01 솔루스첨단소재 주식회사 Organic compound and organic electroluminescent device comprising the same
KR102065817B1 (en) * 2016-06-02 2020-01-13 주식회사 엘지화학 Organic light emitting device
KR102111149B1 (en) * 2016-11-11 2020-05-14 주식회사 엘지화학 Organic light emitting device
KR20190011090A (en) * 2017-07-24 2019-02-01 주식회사 동진쎄미켐 Novel compound and organic electroluminescent divice including the same
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Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110386894A (en) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 A kind of hole mobile material and its application

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