CN111320565A - Organic material, preparation method thereof and organic electroluminescent device - Google Patents

Organic material, preparation method thereof and organic electroluminescent device Download PDF

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CN111320565A
CN111320565A CN202010150528.2A CN202010150528A CN111320565A CN 111320565 A CN111320565 A CN 111320565A CN 202010150528 A CN202010150528 A CN 202010150528A CN 111320565 A CN111320565 A CN 111320565A
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organic material
formula
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CN111320565B (en
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李建行
李明
郎兴旺
赵阔
丁聪
赵大斌
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

The invention discloses an organic material, a preparation method thereof and an organic electroluminescent device, belonging to the field of chemical synthesis and photoelectric materials, and the structural general formula is as follows:
Figure DDA0002402282160000011
in the formula, Ar1、Ar2、Ar3And Ar4Each independently is one of hydrogen, deuterium, halogen, cyano, aryl and heteroaryl;Ar3and Ar4Independently form a C6-C14 aromatic ring or a C4-C18 heteroaromatic ring with other substituents on the ring. According to the embodiment of the invention, the specific heterocyclic combination is selected, and the obtained organic material can improve the hole transmission efficiency after being used for an organic electroluminescent device, well block excitons, ensure that the energy level collocation is matched, and balance holes and electrons in the device, so that the starting voltage of the device can be reduced, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Organic material, preparation method thereof and organic electroluminescent device
Technical Field
The invention relates to the field of chemical synthesis and photoelectric materials, in particular to an organic material, a preparation method thereof and an organic electroluminescent device.
Background
The organic electroluminescent device has an all-solid-state structure, organic electroluminescent materials are the core and the foundation of the device, and the development of new materials is the source power for promoting the continuous progress of the electroluminescent technology. The original material preparation and device optimization are also the research hotspots of the current organic electroluminescent industry, and researchers gradually change the mechanism of an organic layer in a device from a single layer to a multi-layer structure in order to manufacture an organic light-emitting device with high efficiency. The organic electroluminescent device is designed into a multilayer structure, because the moving speeds of holes and electrons are different, a hole injection layer, a hole transmission layer, an exciton blocking layer, a luminescent layer, a hole blocking layer, an electron transmission layer and an electron injection layer are properly designed, the transmission efficiency of the holes and the electrons is improved, the holes and the electrons in the device are balanced, and the luminous efficiency is improved.
However, at present, the hole transport layer, the exciton blocking layer or the hole transport layer and the exciton blocking layer have the problems of not fast mobility, low hole transport efficiency, and not being able to block excitons, which results in the phenomena of high starting voltage, low efficiency, short device lifetime, and the like of the organic electroluminescent device, and thus, there is a need to research an organic material with excellent performance.
Disclosure of Invention
An object of an embodiment of the present invention is to provide an organic material to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an organic material having a general structural formula of formula I:
Figure BDA0002402282150000011
in the formula, Ar1、Ar2、Ar3And Ar4Each independently is one of hydrogen, deuterium, halogen, cyano, aryl and heteroaryl; ar (Ar)3And Ar4Independently form a C6-C14 aromatic ring or a C4-C18 heteroaromatic ring with other substituents on the ring.
Preferably, the aryl group is independently one of benzene, biphenyl, terphenyl, naphthalene, anthracene, and fluorene.
Preferably, the chemical structural formula of the organic material is one of formula L001 to formula L096:
Figure BDA0002402282150000021
Figure BDA0002402282150000031
Figure BDA0002402282150000041
Figure BDA0002402282150000051
Figure BDA0002402282150000061
Figure BDA0002402282150000071
Figure BDA0002402282150000081
Figure BDA0002402282150000091
Figure BDA0002402282150000101
Figure BDA0002402282150000111
Figure BDA0002402282150000121
Figure BDA0002402282150000131
Figure BDA0002402282150000141
another object of an embodiment of the present invention is to provide a method for preparing the organic material, which includes the following steps:
reacting a compound A with a general formula II and a compound B with a general formula III to obtain an intermediate C with a general formula IV;
reacting the intermediate C with a compound D with a general formula V to obtain the organic material;
Figure BDA0002402282150000142
wherein X is halogen.
Preferably, the step of reacting compound a of formula II with compound B of formula III to obtain intermediate C of formula IV specifically comprises:
under the protection atmosphere, mixing a compound A with a general formula II, a compound B with a general formula III, toluene and sodium tert-butoxide, and then adding tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine for reaction to obtain an intermediate C with a general formula IV.
The specific synthetic route is as follows:
Figure BDA0002402282150000151
preferably, the step of reacting the intermediate C with the compound D having the formula V to obtain the organic material specifically includes:
and mixing the intermediate C, a compound D with a general formula V, toluene and sodium tert-butoxide in a protective atmosphere, and adding tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine for reaction to obtain the organic material.
The specific synthetic route is as follows:
Figure BDA0002402282150000152
another object of an embodiment of the present invention is to provide an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein part or all of the organic layer includes the above organic material.
Preferably, the organic layer comprises a hole transport layer and/or an exciton blocking layer comprising the organic material.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
according to the embodiment of the invention, the specific heterocyclic combination is selected, and the obtained organic material can improve the hole transmission efficiency after being used for an organic electroluminescent device, well block excitons, ensure that the energy level collocation is matched, and balance holes and electrons in the device, so that the starting voltage of the device can be reduced, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
This example provides an organic material having a chemical formula of formula L001 in the summary of the invention, and the reaction route of the preparation method of the organic material is as follows:
Figure BDA0002402282150000161
Figure BDA0002402282150000171
the specific preparation method comprises the following steps:
1) weighing compound A-01(29.9mmol, 10g) and compound B-01(27.2 mmol 1, 6.3g) into a reaction system under the protection of nitrogen, adding 200ml toluene, adding 5.2g sodium tert-butoxide, replacing nitrogen once, adding 0.5g tris (dibenzylideneacetone) dipalladium and 0.3g 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring the absence of the raw material B-01 by TLC spot plate, cooling to 25 ℃, drying the reaction liquid by 100g anhydrous sodium sulfate, passing the organic phase through a silica gel funnel of 200g silica gel, spinning the filtrate of the organic phase to no liquid outflow, adding 100ml dichloromethane for dissolving, performing column chromatography (200-300 mesh, 400g) of a developing agent DCM (PE is 1: 1), spinning the receiving liquid to no liquid outflow, adding petroleum ether, stirring for 20 minutes, leaching the filter cake by using petroleum ether, the filter cake was vacuum dried to give intermediate C-01 as a white powder (8.6g, 65% yield); intermediate C-01, having an HPLC purity of greater than 99%, calculated for mass spectrometry of 486.62, test value of 486.60, calculated for elemental analysis: 88.86 percent of C; 5.39 percent of H; 5.76 percent of N; the elemental analysis test values were: 88.85 percent of C; 5.40 percent of H; and 5.80 percent of N.
2) Weighing intermediate C-01(17.7mmol, 8.6g) and compound D-01(19.5 mmol 1, 5.3g) into a reaction system under the protection of nitrogen, adding 170ml of toluene, adding 3.4g of sodium tert-butoxide, replacing primary nitrogen, adding 0.33g of tris (dibenzylideneacetone) dipalladium and 0.15g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material C-01 remains by a TLC point plate, cooling to 25 ℃, performing suction filtration, leaching a filter cake by petroleum ether, performing vacuum drying on the filter cake, heating the product by 80ml of toluene to 110 ℃, reducing the temperature to 25 ℃ to precipitate, performing suction filtration, leaching the filter cake by petroleum ether, and performing vacuum drying at 50 ℃ to obtain an organic material L001(4.8g, the yield of 40%) of white-like powder. The organic material had an HPLC purity of greater than 99.5%, calculated mass spectrum of 678.88, test value of 678.90; the calculated value of the element analysis is as follows: 90.23 percent of C; 5.64 percent of H; 4.13 percent of N; the elemental analysis test values were: 90.20 percent of C; 5.60 percent of H; and 4.10 percent of N.
Example 2
This example provides an organic material having a chemical formula of formula L006 in the summary of the invention, and the reaction route of the preparation method of the organic material is as follows:
Figure BDA0002402282150000181
the specific preparation method comprises the following steps:
1) weighing a compound A-06(29.9mmol, 10g) and a compound B-06(27.2 mmol 1, 6.3g) into a reaction system under the protection of nitrogen, adding 200ml toluene, adding 5.2g sodium tert-butoxide, replacing nitrogen once, adding 0.5g tris (dibenzylideneacetone) dipalladium and 0.3g 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material B-06 remains by a TLC point plate, cooling to 25 ℃, drying a reaction solution by 100g anhydrous sodium sulfate, passing an organic phase through a silica gel funnel of 200g silica gel, rotating an organic phase filtrate until no liquid flows out, adding 100ml dichloromethane for dissolving, carrying out column chromatography (200-300 meshes, 400g) of a developing agent DCM (PE is 1:1, rotating a receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20 minutes, leaching a filter cake by using petroleum ether, drying the filter cake in vacuum to obtain an intermediate C-06(7.2g, yield 55%) of white powder; the HPLC purity of the intermediate C-06 is more than 99 percent; calculated mass spectrum 486.62; the test value was 486.60. The calculated value of the element analysis is as follows: 88.86 percent of C; 5.39 percent of H; 5.76 percent of N; the elemental analysis test values were: 88.85 percent of C; 5.40 percent of H; and 5.80 percent of N.
2) Weighing an intermediate C-06(14.8mmol, 7.2g) and a compound D-06(16.28 mmol 1, 5.3g) into a reaction system under the protection of nitrogen, adding 150ml of toluene, adding 2.7g of sodium tert-butoxide, replacing primary nitrogen, adding 0.3g of tris (dibenzylideneacetone) dipalladium and 0.13g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material C-06 remains by a TLC point plate, cooling to 25 ℃, performing suction filtration, leaching a filter cake by petroleum ether, performing vacuum drying on the filter cake, heating the product by 80ml of toluene to 110 ℃, reducing to 25 ℃ to separate out, performing suction filtration, leaching the filter cake by petroleum ether, and performing vacuum drying at 50 ℃ to obtain an organic material L006(5.4g, the yield of 50%) of white-like powder; the HPLC purity of the organic material is greater than 99.5%; calculated mass spectrum 728.94; the test value was 728.94. The calculated value of the element analysis is as follows: 90.63 percent of C; 5.53 percent of H; 3.84 percent of N; the test values are: 90.60 percent of C; 5.50 percent of H; and 3.80 percent of N.
Example 3
This example provides an organic material, the chemical structural formula of which is formula L023 in the summary of the invention, and the reaction route of the preparation method of the organic material is as follows:
Figure BDA0002402282150000191
Figure BDA0002402282150000201
the specific preparation method comprises the following steps:
1) weighing a compound A-23(29.9mmol, 10g) and a compound B-23(27.2 mmol 1, 6.3g) into a reaction system under the protection of nitrogen, adding 200ml of toluene, adding 5.2g of sodium tert-butoxide, replacing nitrogen once, adding 0.5g of tris (dibenzylideneacetone) dipalladium and 0.3g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material B-06 remains by a TLC point plate, cooling to 25 ℃, drying a reaction liquid by 100g of anhydrous sodium sulfate, passing an organic phase through a silica gel funnel of 200g of silica gel, rotating an organic phase filtrate until no liquid flows out, adding 100ml of dichloromethane for dissolving, carrying out column chromatography (200-300 meshes, 400g) of a developing agent DCM (PE is 1: 1), rotating a receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20 minutes, leaching a filter cake by using petroleum ether, the filter cake was vacuum dried to give intermediate C-23 as a white powder (8.6g, 65% yield); the HPLC purity of the intermediate C-23 is more than 99 percent; calculated mass spectrum 486.62; the test value was 486.60. The calculated value of the element analysis is as follows: 88.86 percent of C; 5.39 percent of H; 5.76 percent of N; the element analysis test value is 88.85 percent; 5.40 percent of H; and 5.80 percent of N.
2) Weighing an intermediate C-23(17.7mmol, 8.6g) and a compound D-23(19.5 mmol 1, 6.2g) into a reaction system under the protection of nitrogen, adding 170ml of toluene, adding 3.4g of sodium tert-butoxide, replacing primary nitrogen, adding 0.33g of tris (dibenzylideneacetone) dipalladium and 0.15g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material C-23 remains by a TLC point plate, cooling to 25 ℃, performing suction filtration, leaching a filter cake by petroleum ether, performing vacuum drying on the filter cake, heating the product by 100ml of toluene to 110 ℃, reducing the temperature to 25 ℃ to separate out, performing suction filtration, leaching the filter cake by petroleum ether, and performing vacuum drying at 50 ℃ to obtain an organic material L023(5.8g, the yield of 45%) of white-like powder; the HPLC purity of the organic material is greater than 99.5%; calculated mass spectrum 728.94; the test value was 728.94. The calculated value of the element analysis is as follows: 90.63 percent of C; 5.53 percent of H; 3.84 percent of N; the test values are: 90.60 percent of C; 5.50 percent of H; and 3.80 percent of N.
Example 4
This example provides an organic material having a chemical formula of formula L056 in the summary of the invention, and the reaction route of the preparation method of the organic material is as follows:
Figure BDA0002402282150000211
the specific preparation method comprises the following steps:
1) weighing a compound A-56(26mmol, 10g) and a compound B-23(23.6 mmol 1, 5.5g) into a reaction system under the protection of nitrogen, adding 200ml toluene, adding 4.5g sodium tert-butoxide, replacing nitrogen once, adding 0.4g tris (dibenzylideneacetone) dipalladium and 0.2g 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that the raw material B-56 is not remained by a TLC point plate, cooling to 25 ℃, drying a reaction solution by 100g anhydrous sodium sulfate, passing an organic phase through a silica gel funnel of 200g silica gel, rotating an organic phase filtrate until no liquid flows out, adding 100ml dichloromethane for dissolving, carrying out column chromatography on a solution (200-300 meshes, 400g) by taking a developing agent DCM: PE (1: 1), rotating the liquid until no liquid flows out, adding petroleum ether for stirring for 20 minutes, filtering a filter cake, eluting by petroleum ether, the filter cake was vacuum dried to give intermediate C-56 as a white powder (7.6g, 60% yield); the HPLC purity of the intermediate C-56 is more than 99 percent, and the calculated mass spectrum value is 536.68; the test value was 536.70. The calculated value of the element analysis is as follows: 89.52 percent of C; 5.26 percent of H; 5.22 percent of N; the elemental analysis test values were: 89.50 percent of C; 5.30 percent of H; and 5.20 percent of N.
2) Weighing an intermediate C-56(14.2mmol, 7.6g) and a compound D-56(15.6 mmol 1, 4.3g) into a reaction system under the protection of nitrogen, adding 170ml of toluene, adding 2.7g of sodium tert-butoxide, replacing primary nitrogen, adding 0.26g of tris (dibenzylideneacetone) dipalladium and 0.13g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material C-56 remains by a TLC point plate, cooling to 25 ℃, performing suction filtration, leaching a filter cake by petroleum ether, performing vacuum drying on the filter cake, heating the product by 100ml of toluene to 110 ℃, reducing the temperature to 25 ℃ to separate out, performing suction filtration, leaching the filter cake by petroleum ether, and performing vacuum drying at 50 ℃ to obtain an organic material L056(4.4g, the yield being 42%) of white-like powder; the organic material had an HPLC purity of greater than 99.5% calculated on the mass spectrum of 728.94; the test value was 728.94. The calculated value of the element analysis is as follows: 90.63 percent of C; 5.53 percent of H; 3.84 percent of N; the elemental analysis test values were: 90.60 percent of C; 5.50 percent of H; and 3.80 percent of N.
Example 5
This example provides an organic material having a chemical formula of formula L077 in the summary of the invention, and the reaction route of the preparation method of the organic material is as follows:
Figure BDA0002402282150000221
Figure BDA0002402282150000231
the specific preparation method comprises the following steps:
1) weighing a compound A-77(32.4mmol, 10g) and a compound B-77(29.5 mmol 1, 6.1g) into a reaction system under the protection of nitrogen, adding 200ml toluene, adding 5.7g sodium tert-butoxide, replacing nitrogen once, adding 0.54g tris (dibenzylideneacetone) dipalladium and 0.24g 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material B-56 remains by a TLC point plate, cooling to 25 ℃, drying a reaction solution by 100g anhydrous sodium sulfate, passing an organic phase through a silica gel funnel of 200g silica gel, rotating an organic phase filtrate until no liquid flows out, adding 100ml dichloromethane for dissolving, performing column chromatography (200-300 meshes, 400g) on a developing agent DCM (PE is 1: 1), rotating a receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20 minutes, leaching a filter cake by using petroleum ether, the filter cake was vacuum dried to give intermediate C-77 as a white powder (7.7g, 60% yield); the HPLC purity of the intermediate C-77 is more than 99 percent; calculated mass spectrum 434.54; the test value was 434.50. The calculated value of the element analysis is as follows: 89.52 percent of C; 5.26 percent of H; 5.22 percent of N; the elemental analysis test values were: 89.50 percent of C; 5.30 percent of H; and 5.20 percent of N.
2) Weighing an intermediate C-77(17.7mmol, 7.7g) and a compound D-77(19.47 mmol 1, 5.3g) into a reaction system under the protection of nitrogen, adding 150ml of toluene, adding 3.4g of sodium tert-butoxide, replacing primary nitrogen, adding 0.32g of tris (dibenzylideneacetone) dipalladium and 0.14g of 50% tri-tert-butylphosphine under the protection of nitrogen, refluxing for 24 hours at 110 ℃ under the protection of nitrogen, monitoring that no raw material C-77 remains by a TLC point plate, cooling to 25 ℃, performing suction filtration, leaching a filter cake by petroleum ether, performing vacuum drying on the filter cake, heating the product by 100ml of toluene to 110 ℃, reducing the temperature to 25 ℃ to precipitate, performing suction filtration, leaching the filter cake by using petroleum ether, and performing vacuum drying at 50 ℃ to obtain an organic material L077(5.5g, the yield being 50%) of white-like powder; the HPLC purity of the organic material is greater than 99.5%; calculated mass spectrum 626.80; the test value was 626.80. The calculated value of the element analysis is as follows: 90.06 percent of C; 5.47 percent of H; 4.47 percent of N; the elemental analysis test values were: 90.0 percent of C; 5.50 percent of H; n is 4.50 percent.
The synthetic routes and principles of the preparation methods of the other compounds with the general structural formulas of formula I in the summary of the invention are the same as those of the above-listed examples 1 to 5, so that the description is not exhaustive, and the invention selects 6 compounds (formula L012, L028, L035, L047, L062, L086 in the summary of the invention) as examples, and the corresponding mass spectrum test values and molecular formulas are shown in table 1 below.
TABLE 1
Structural formula of compound Molecular formula Calculated mass spectrum Mass spectrometric test values Final product yield
L012 C61H44N2 804.35 804.30 42％
L028 C61H44N2 804.35 804.40 45％
L035 C44H32N2 588.26 588.30 44％
L047 C47H34N2 626.27 626.30 50％
L062 C57H41N3 767.33 767.30 44％
L086 C58H44N2 768.35 768.30 49％
The embodiment of the invention also provides an organic electroluminescent device prepared by adopting the organic material provided by the embodiment, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode.
The organic material provided in the above embodiments can be used as a material for both the hole transport layer and the exciton blocking layer.
The organic electroluminescent device mentioned in the embodiments of the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used. In addition, the organic material provided by the embodiment of the invention can also be used for organic electronic devices using a principle similar to that of an organic electroluminescent device, such as an organic solar cell, an organic photoconductor, an organic transistor, and the like.
Specifically, the method for manufacturing the organic electroluminescent element described above can be referred to example 6.
Example 6
The embodiment provides a method for manufacturing an organic electroluminescent device, which includes the steps of:
(1) coating with a thickness of
Figure BDA0002402282150000251
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater.
(2) Firstly, evaporating CuPc on ITO (anode)
Figure BDA0002402282150000252
The organic material having the chemical formula of L001 provided in example 1 was then sequentially deposited
Figure BDA0002402282150000253
Mixture of host material compound H1 and dopant material compound Ir (piq)2acac in a 95:5 weight ratio
Figure BDA0002402282150000254
Then evaporating an electron transport layer 'Alq 3'
Figure BDA0002402282150000255
Evaporation of electron injection layer LiF
Figure BDA0002402282150000256
Deposition cathode Al
Figure BDA0002402282150000257
Thus obtaining the organic electroluminescent device.
Wherein the structural formula of the main substance compound H1 is as follows:
Figure BDA0002402282150000258
the dopant material compound Ir (piq)2acac has the formula:
Figure BDA0002402282150000259
the structural formula of Alq3 is:
Figure BDA0002402282150000261
with reference to the method provided in example 6, organic materials having chemical structural formulas L006, L023, L056, L077, L012, L028, L035, L047, L062, and L086 are respectively selected to replace the organic material having the structural formula L001 for evaporation, and a corresponding organic electroluminescent device is prepared.
Comparative example 1
This comparative example provides an organic electroluminescent device, and the only difference between the preparation method of the organic electroluminescent device and example 6 is that the organic electroluminescent device is vapor-deposited by using the existing organic compound NPB instead of the organic material having the chemical structural formula of L001. Wherein the structural formula of NPB is as follows:
Figure BDA0002402282150000262
the organic electroluminescent devices obtained in example 6 and comparative example 1 were tested for driving voltage, luminous efficiency, and T95 lifetime using a KEITHLEY model 2400 source measuring unit and a CS-2000 spectroradiometer, respectively, and the test results are shown in table 2 below.
TABLE 2
Figure BDA0002402282150000263
Figure BDA0002402282150000271
As can be seen from table 2 above, compared with the organic electroluminescent device made of the existing NPB material, the organic electroluminescent device made of the organic material provided in the embodiment of the present invention has significantly reduced driving voltage, significantly improved luminous efficiency and significantly improved lifetime.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (8)

1. An organic material having a general structural formula of formula I:
Figure FDA0002402282140000011
in the formula, Ar1、Ar2、Ar3And Ar4Each independently is one of hydrogen, deuterium, halogen, cyano, aryl and heteroaryl; ar (Ar)3And Ar4Independently form a C6-C14 aromatic ring or a C4-C18 heteroaromatic ring with other substituents on the ring.
2. An organic material as claimed in claim 1, wherein the aryl groups are independently one of benzene, biphenyl, terphenyl, naphthalene, anthracene and fluorene.
3. The organic material as claimed in claim 1, wherein the chemical structural formula of the organic material is one of formula L001 to formula L096:
Figure FDA0002402282140000012
Figure FDA0002402282140000021
Figure FDA0002402282140000031
Figure FDA0002402282140000041
Figure FDA0002402282140000051
Figure FDA0002402282140000061
Figure FDA0002402282140000071
Figure FDA0002402282140000081
Figure FDA0002402282140000091
Figure FDA0002402282140000101
Figure FDA0002402282140000111
Figure FDA0002402282140000121
Figure FDA0002402282140000131
4. a method for preparing an organic material according to any one of claims 1 to 3, comprising the steps of:
reacting a compound A with a general formula II and a compound B with a general formula III to obtain an intermediate C with a general formula IV;
reacting the intermediate C with a compound D with a general formula V to obtain the organic material;
Figure FDA0002402282140000132
wherein X is halogen.
5. The method for preparing an organic material according to claim 4, wherein the step of reacting the compound A having the formula II with the compound B having the formula III to obtain the intermediate C having the formula IV comprises:
under the protection atmosphere, mixing a compound A with a general formula II, a compound B with a general formula III, toluene and sodium tert-butoxide, and then adding tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine for reaction to obtain an intermediate C with a general formula IV.
6. The method for preparing an organic material according to claim 4, wherein the step of reacting the intermediate C with the compound D having the formula V to obtain the organic material specifically comprises:
and mixing the intermediate C, a compound D with a general formula V, toluene and sodium tert-butoxide in a protective atmosphere, and adding tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine for reaction to obtain the organic material.
7. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer partially or entirely comprises the organic material according to any one of claims 1 to 3.
8. An organic electroluminescent device according to claim 7, wherein the organic layer comprises a hole transport layer and/or an exciton blocking layer, said hole transport layer and/or exciton blocking layer comprising said organic material.
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