CN113528125B - Host material and organic electroluminescent device comprising same - Google Patents

Host material and organic electroluminescent device comprising same Download PDF

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CN113528125B
CN113528125B CN202111083752.5A CN202111083752A CN113528125B CN 113528125 B CN113528125 B CN 113528125B CN 202111083752 A CN202111083752 A CN 202111083752A CN 113528125 B CN113528125 B CN 113528125B
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organic electroluminescent
electroluminescent device
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CN113528125A (en
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叶绪兵
赵晓宇
高春吉
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

The invention provides a main partA bulk material and an organic electroluminescent device including the same, the host material including at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 below and the second host compound is represented by formula 2 below:
Figure DEST_PATH_IMAGE001

Description

Host material and organic electroluminescent device comprising same
Technical Field
The present invention relates to a host material, and more particularly, to a host material and an organic electroluminescent device including the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have excellent performance and certain application value, but as a host material in an organic electroluminescent device, the host material has good hole transport performance except that the triplet state energy level is higher than that of a guest material, and energy reverse transfer for exciton transition release is prevented. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
In order to overcome the disadvantages of the prior art, it is an object of the present invention to provide a host material and an organic electroluminescent device including the same, which has excellent luminous efficiency and lifetime.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the present invention provides a host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 below and the second host compound is represented by formula 2 below:
Figure 346356DEST_PATH_IMAGE001
Figure 201179DEST_PATH_IMAGE002
wherein Ar is1、Ar2、Ar3And Ar4Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
X1、X2and X3Each independently selected from carbon or nitrogen;
y1 and Y2 are each independently selected from nitrogen (N) or oxygen (O);
L1selected from single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene.
Preferably, the first host compound is represented by any one of the following formulae 1-1 to 1-4:
Figure 184179DEST_PATH_IMAGE003
wherein Ar is1、Ar2And Ar3Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
x1, X2, and X3 are each independently selected from carbon or nitrogen.
More preferably, the first host compound is any one of, but not limited to:
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Figure 869178DEST_PATH_IMAGE005
Figure 894903DEST_PATH_IMAGE006
Figure 834040DEST_PATH_IMAGE007
Figure 236203DEST_PATH_IMAGE008
Figure 373923DEST_PATH_IMAGE009
Figure 803505DEST_PATH_IMAGE010
Figure 495518DEST_PATH_IMAGE011
Figure 435792DEST_PATH_IMAGE012
Figure 162439DEST_PATH_IMAGE013
Figure 795546DEST_PATH_IMAGE014
Figure 738969DEST_PATH_IMAGE015
Figure 217355DEST_PATH_IMAGE016
Figure 798509DEST_PATH_IMAGE017
Figure 336938DEST_PATH_IMAGE018
Figure 269121DEST_PATH_IMAGE019
Figure 49733DEST_PATH_IMAGE020
Figure 750973DEST_PATH_IMAGE021
Figure 725882DEST_PATH_IMAGE022
Figure 879783DEST_PATH_IMAGE023
Figure 965551DEST_PATH_IMAGE024
Figure 754253DEST_PATH_IMAGE025
Figure 634484DEST_PATH_IMAGE026
Figure 275681DEST_PATH_IMAGE027
Figure 899561DEST_PATH_IMAGE028
Figure 575393DEST_PATH_IMAGE029
Figure 125060DEST_PATH_IMAGE030
Figure 253553DEST_PATH_IMAGE031
Figure 415545DEST_PATH_IMAGE032
Figure 680304DEST_PATH_IMAGE033
Figure 666452DEST_PATH_IMAGE034
Figure 282241DEST_PATH_IMAGE035
Figure 513502DEST_PATH_IMAGE036
Figure 632768DEST_PATH_IMAGE037
Figure 25703DEST_PATH_IMAGE038
Figure 627324DEST_PATH_IMAGE039
Figure 131117DEST_PATH_IMAGE040
Figure 636048DEST_PATH_IMAGE041
Figure 934305DEST_PATH_IMAGE042
Figure 524687DEST_PATH_IMAGE043
Figure 330706DEST_PATH_IMAGE044
preferably, the second host compound is represented by any one of the following formulae 2-1 to 2-3:
Figure 424564DEST_PATH_IMAGE045
wherein Ar is4And Ar5Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
L1is a single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene.
More preferably, the second host compound is any one of, but not limited to:
Figure 424881DEST_PATH_IMAGE046
Figure 971400DEST_PATH_IMAGE047
Figure 348155DEST_PATH_IMAGE048
Figure 795055DEST_PATH_IMAGE049
the invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and the organic functional layer contains the host material.
Preferably, the organic functional layer is a light-emitting layer, and the light-emitting layer further contains a dopant.
More preferably, the mass ratio of the host material to the dopant is 10:1 to 100: 1.
More preferably, the mass ratio of the first host compound to the second host compound in the host material is 1:9 to 9: 1.
The invention provides a host material, which comprises at least one first host compound and at least one second host compound, wherein an electron-rich heterocyclic chain structure in the host compound structure has great influence on the photoelectric properties of the whole compound molecule, and is beneficial to reducing unnecessary vibration energy loss, so that high-efficiency light emission is realized. By adjusting substituent groups, the complex has better thermal stability and chemical properties. In addition, the preparation method of the various main compounds is simple, the raw materials are easy to obtain, and the industrial requirements can be met.
The host compound disclosed by the invention is prepared into a device, and particularly used as a host material, the device has the advantages of low driving voltage, high luminous efficiency and the like, and is obviously superior to the conventional common OLED device.
Detailed Description
The organic electroluminescent device of the present invention preferably comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode. The term "organic functional layer" refers to all layers disposed between an anode and a cathode in an organic electroluminescent device, and the organic functional layer may be a layer having a hole property and a layer having an electron property, for example, the organic functional layer includes one or more of a hole injection layer, a hole transport layer, a hole injection and transport functional layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection functional layer.
The hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties of the present invention may include an electron-generating substance in addition to a conventional hole injection substance, a conventional hole transport substance, and a substance having both hole injection and hole transport properties. For example, the organic functional layer is an emissive layer, and the emissive layer includes one or more of phosphorescent hosts, fluorescent hosts, phosphorescent dopants, and fluorescent dopants. The compound for the organic electroluminescent device can be used as a fluorescent main body, can also be used as fluorescent doping, and can be used as the fluorescent main body and the fluorescent doping at the same time.
The light-emitting layer of the present invention may be a red, yellow or blue light-emitting layer. And when the luminescent layer is a red luminescent layer, the compound for the organic electroluminescent device is used as a red main body, so that the organic electroluminescent device with high efficiency, high resolution, high brightness and long service life can be obtained.
The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited, wherein the red phosphorescent compound is used as a host material of the light-emitting layer.
The dopant in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material is not particularly limited, but may be preferably selected from a metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallized complex compound selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
Specific examples of the dopant compound are as follows, but are not limited thereto.
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Figure 88DEST_PATH_IMAGE051
Figure 914954DEST_PATH_IMAGE052
Figure 216361DEST_PATH_IMAGE053
In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma and ion plating methods, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, and flow coating methods may be used.
When a solvent is used in the wet film forming method, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which a material forming each layer can be dissolved or diffused and in which there is no problem in film forming ability.
In addition, the compound represented by formula 1 and the compound represented by formula 2 may be subjected to film formation in the above-listed methods, typically by a co-evaporation method or a mixed evaporation method.
The present disclosure may provide a display system by including a plurality of host materials. In addition, it is possible to produce a display system or an illumination system by using the organic electroluminescent device of the present disclosure. In particular by using the various host compound materials of the present disclosure it is possible to produce display systems, for example for smartphones, tablet computers, notebooks, PCs, TVs, or cars, or to produce lighting systems, for example outdoor or indoor lighting systems.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and other methods and materials for preparing the organic electroluminescent device known to those skilled in the art may be used in addition to the host compound represented by formula 1.
Examples
Example 1: synthesis of Compounds 1-18
(1) Synthesis of intermediate 1-1-2
Figure 558480DEST_PATH_IMAGE054
Compounds (1-18-2) (7.9 g, 23.7mmol), 1-18-1(6.53g, 21.6mmol), tetrakis (triphenylphosphine) palladium (1.2g, 1.0mmol), potassium carbonate (7.5g, 59mmol) were added) 90mL of toluene, 30mL of ethanol, and 30mL of distilled water were added to the reaction vessel, and the reaction was stirred at 120 ℃ for 4 hours. After completion of the reaction, methanol was added dropwise to the mixture, and the resulting solid was filtered. The obtained solid was purified by recrystallization through column chromatography to obtain the compound 1-18-3(5.4g, yield: 53%). LC-MS: M/Z469.13 (M)+)。
2) Synthesis of Compounds 1-18
Compound A (10.1 g, 23.7mmol), 1-18-3(10.2g, 21.6mmol), tetrakis (triphenylphosphine) palladium (1.2g, 1.0mmol), potassium carbonate (7.5g, 59mmol), 90mL of toluene, 30mL of ethanol, and 30mL of distilled water were added to a reaction vessel and the reaction was stirred at 120 ℃ for 4 hours. After completion of the reaction, methanol was added dropwise to the mixture, and the resulting solid was filtered. The obtained solid was purified by recrystallization through column chromatography to obtain compounds 1 to 18(9.5g, yield: 60%). LC-MS: M/Z728.26 (M)+)。
Example 2: synthesis of Compounds 1-39
Figure 345171DEST_PATH_IMAGE055
Compounds 1 to 39 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compounds 1 to 18 to give compounds 1 to 39(8.9g, yield: 67%). LC-MS: M/Z616.19 (M)+)。
Example 3: synthesis of Compounds 2-83
Figure 798149DEST_PATH_IMAGE056
Compounds 2 to 83 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compounds 1 to 18, to give compounds 2 to 83(11.1g, yield: 63%). LC-MS: M/Z817.28 (M)+)。
Example 4: synthesis of Compounds 3-45
Figure 986685DEST_PATH_IMAGE057
Compounds 3 to 45 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compounds 1 to 18 to give compounds 3 to 45(9.8g, yield: 68%). LC-MS: M/Z666.21 (M)+)。
Example 5: synthesis of Compounds 4-91
Figure 732661DEST_PATH_IMAGE058
Compounds 4 to 91 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compounds 1 to 18 to give compounds 4 to 91(9.5g, yield: 54%). LC-MS: M/Z742.24 (M)+)。
Example 6: synthesis of Compounds 4-96
Figure 6648DEST_PATH_IMAGE059
Compounds 4 to 96 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compounds 1 to 18 to give compounds 4 to 96(9.2g, yield: 51%). LC-MS: M/Z716.22 (M)+)。
< Experimental example 1> production of organic light-emitting device
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed, and then placed in a vacuum chamber with a standard pressure set at 1X 10-6And (4) supporting. Thereafter evaporating HIL-1 on an ITO substrate to form a first Hole Injection Layer (HIL) having a thickness of 1150 a, evaporating HIL-2 on the first hole injection layer to form a second hole injection layer having a thickness of 50 a, evaporating HTL-1 on the second hole injection layer to form a Hole Transport Layer (HTL) having a thickness of 800 a, continuing to evaporate EB-1 on the hole transport layer to form an Electron Blocking Layer (EBL) having a thickness of 150 a, and depositing the host materials of the invention (i.e., inventive compounds 1-18 and 5) on the electron blocking layer-28) co-evaporating with a guest compound (RD-1) to form an emitting layer (EML) having a thickness of 400 a (wherein inventive compounds 1-18 and 5-28 are mixed evaporated in a 3: 2 mass ratio with a mass ratio of host material to RD-1 of 98: 2) and finally a hole blocking layer (HB) having a thickness of 30 a and an electron transport layer (ET) having a thickness of 400 a were formed sequentially from HB-1 and ET-1, respectively, and then cathodes EI-1(5 a) and Al 1000 a were evaporated, thereby manufacturing an organic electroluminescent device.
Figure 263317DEST_PATH_IMAGE060
Figure 40780DEST_PATH_IMAGE061
Figure 724702DEST_PATH_IMAGE062
2. Second embodiment
An organic electroluminescent device of the second embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 1 to 39 from compounds 1 to 18 of the first embodiment.
3. Third embodiment
An organic electroluminescent device of the third embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 2 to 83 from compounds 1 to 18 of the first embodiment.
4. Fourth embodiment
An organic electroluminescent device of the fourth embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 3 to 45 from compounds 1 to 18 of the first embodiment.
5. Fifth embodiment
An organic electroluminescent device of the fifth embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 4 to 91 from compounds 1 to 18 of the first embodiment.
6. Sixth embodiment
An organic electroluminescent device of the sixth embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 4 to 96 from compounds 1 to 18 of the first embodiment.
7. Comparative example 1
The organic electroluminescent device of comparative example 1 was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compound Ref-1/5-28 from the compounds 1-18/5-28 of the first embodiment.
8. Comparative example 2
The organic electroluminescent device of comparative example 2 was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compound Ref-1/5-36 from the compounds 1-18/5-28 of the first embodiment. The organic electroluminescent device was fabricated using standard methods known in the art at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic electroluminescent devices prepared in the examples and comparative examples of the present invention.
TABLE 1
Figure 718941DEST_PATH_IMAGE063
As shown in table 1, the organic electroluminescent device comprising the specific compound combination according to the present disclosure as a host material has higher luminous efficiency and longer life characteristics than the organic electroluminescent device of the comparative substance.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (5)

1. A host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is any one of:
Figure FDA0003353594950000011
Figure FDA0003353594950000021
Figure FDA0003353594950000031
Figure FDA0003353594950000041
Figure FDA0003353594950000051
Figure FDA0003353594950000061
Figure FDA0003353594950000071
Figure FDA0003353594950000081
Figure FDA0003353594950000091
Figure FDA0003353594950000101
Figure FDA0003353594950000111
Figure FDA0003353594950000121
Figure FDA0003353594950000131
Figure FDA0003353594950000141
Figure FDA0003353594950000151
Figure FDA0003353594950000161
Figure FDA0003353594950000171
Figure FDA0003353594950000181
Figure FDA0003353594950000191
wherein the second host compound is any one of:
Figure FDA0003353594950000201
Figure FDA0003353594950000211
2. an organic electroluminescent device comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the organic functional layer comprises the host material of claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic functional layer is a light-emitting layer further comprising a dopant therein.
4. The organic electroluminescent device according to claim 3, wherein the mass ratio of the host material to the dopant is 10:1 to 100: 1.
5. The organic electroluminescent device according to claim 4, wherein the mass ratio of the first host compound to the second host compound in the host material is 1:9 to 9: 1.
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