CN113620951B - Phosphorescent compound, preparation method thereof and organic electroluminescent device - Google Patents

Phosphorescent compound, preparation method thereof and organic electroluminescent device Download PDF

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CN113620951B
CN113620951B CN202111048253.2A CN202111048253A CN113620951B CN 113620951 B CN113620951 B CN 113620951B CN 202111048253 A CN202111048253 A CN 202111048253A CN 113620951 B CN113620951 B CN 113620951B
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phosphorescent compound
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汪康
张雪
黄悦
马晓宇
林文晶
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Olide Shanghai Photoelectric Material Technology Co ltd
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Abstract

The invention is applicable to the technical field of organic electroluminescent materials, and provides a phosphorescent compound, a preparation method thereof and an organic electroluminescent device. The structural general formula of the phosphorescent compound is as follows:
Figure DDA0003251808880000011
wherein R is 1 、R 2 、R 3 、R 4 Each independently hydrogen, C1-C10 alkyl, cyano, amine, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; x is a bond, O, S, CR 5 R 6 Or NR 7 ；R 5 、R 6 Each independently is a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group; r, R 7 Each independently is a C6-C30 arylene or C3-C20 heteroarylene. The organic electroluminescent device manufactured by the phosphorescent compound has improved driving voltage, luminous efficiency, service life and glass transition temperature.

Description

Phosphorescent compound, preparation method thereof and organic electroluminescent device
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a phosphorescent compound, a preparation method of the phosphorescent compound and an organic electroluminescent device.
Background
The Organic electronic device is typically represented by an Organic Light Emitting device, and a typical example of the Organic Light Emitting device is an Organic Light Emitting Diode (OLED). The organic light emitting diode is a current-driven light emitting device using an organic material as an active material, and particularly, the organic light emitting diode is a technology of OLED display in which an organic semiconductor material and an organic light emitting material are driven by an electric field to emit light through carrier injection and recombination, and has the advantages of being thin in thickness, simple in structure, free of a backlight source, capable of emitting light actively, low in power consumption, wide in viewing angle, high in response speed and the like, and is considered as a strong competitor of the next generation display technology.
The OLED emission is divided into two modes, i.e., fluorescence emission and phosphorescence emission, and it is theorized that the ratio of a singlet excited state to a triplet excited state due to recombination of charges is 1: therefore, when a small-molecule fluorescent material is used, the total energy available for light emission is only 25%, and the remaining 75% of the energy is lost by the triplet excited non-light-emitting mechanism, so that the internal quantum efficiency limit of the fluorescent material is considered to be 25%. In phosphorescence emission, singlet and triplet excitons are utilized, and only singlet excitons are utilized as opposed to fluorescent materials, and efficient utilization of triplet excitons in proportions up to 75% enables a phosphorescent-material-based PhOLED to theoretically achieve 100% internal quantum efficiency. In recent three years, phosphorescent materials gradually replace traditional fluorescent materials, and become hot spots for research on OLED luminescent materials.
A light emitting material may be prepared by combining a host material with a dopant to improve color purity, light emitting efficiency, and stability. The host material greatly affects the efficiency and performance of the organic light emitting device, and it is important to develop a novel host material that meets the requirement of practicality. However, the phosphor materials are complex, time-consuming and have a short lifetime, so that further development of the phosphor materials is urgently needed. Therefore, the application provides a phosphorescent compound, a preparation method thereof and an organic electroluminescent device.
Disclosure of Invention
The embodiments of the present invention are directed to providing a phosphorescent compound, a method for preparing the same, and an organic electroluminescent device, and are intended to solve the problems in the prior art pointed out in the background art.
The embodiment of the invention is realized by a phosphorescent compound, and the structural general formula of the phosphorescent compound is shown as the following general formula I:
Figure BDA0003251808870000021
wherein R is 1 、R 2 、R 3 、R 4 Each independently is hydrogen, C1-C10 alkyl, cyano, amine, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;
x is a chemical bond, O, S, CR 5 R 6 Or NR 7 ；
R 5 、R 6 Each independently is a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;
R、R 7 each independently is a C6-C30 arylene or C3-C20 heteroarylene;
R 1 -R 4 the substituted position is any position on the benzene ring, and the number of the substituted positions is an integer of 0-4.
As another preferable scheme of the embodiment of the invention, the structural general formula of the phosphorescent compound is general formula I-1 to general formula I-10:
Figure BDA0003251808870000031
as another preferable mode of the embodiment of the present invention, R is 1 、R 2 、R 3 、R 4 Each independently hydrogen, methyl, ethyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, quinoxalinyl, or amino;
R 1 、R 2 、R 3 or R 4 May be fused with its adjacent aromatic ring to form a ring or substituted.
As another preferable mode of the embodiment of the present invention, R is 5 、R 6 Each independently is methyl, ethyl, propyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; r is 7 Is cyclohexyl or phenylNaphthyl, biphenyl, methylbenzene or terphenyl.
As another preferable mode of the embodiment of the present invention, R is phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracyl, pyrenyl, perylenyl, triphenylenyl, fluoranthenyl, triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, or quinoxalinyl, and any of the following groups:
Figure BDA0003251808870000041
Figure BDA0003251808870000051
Figure BDA0003251808870000061
as another preferable mode of the embodiment of the present invention, the chemical structural formula of the phosphorescent compound is one of formula 1 to formula 156:
Figure BDA0003251808870000071
Figure BDA0003251808870000081
Figure BDA0003251808870000091
Figure BDA0003251808870000101
Figure BDA0003251808870000111
Figure BDA0003251808870000121
Figure BDA0003251808870000131
another objective of the embodiments of the present invention is to provide a preparation method of the phosphorescent compound, which comprises the following synthetic route:
Figure BDA0003251808870000132
the method specifically comprises the following steps:
under the protective atmosphere, placing a reactant A-I, a reactant B-I, tetrakis (triphenylphosphine palladium) and potassium carbonate in a solvent for reaction; after the reaction is finished, purifying the obtained product to obtain an intermediate C-I;
under a protective atmosphere, the intermediate C-I, pd (OAc) is added 2 、Pcy 3 And potassium carbonate, put into solvent and react; after the reaction is finished, the mixture is washed and extracted, and the obtained organic layer is eluted and purified to obtain the phosphorescent compound with the general structural formula I.
Preferably, it comprises the following steps:
(1) In a reaction flask, under nitrogen protection, reactants a-I (1.0 eq), reactants B-I (2.2 eq), tetrakis (triphenylphosphine palladium) (0.01 eq), potassium carbonate (2.5 eq), and solvent were added: toluene/ethanol/water (volume ratio 3; after the reaction is finished, cooling to room temperature, filtering, and recrystallizing and purifying the obtained solid by toluene to obtain an intermediate C-I;
(2) In a reaction flask, under the protection of nitrogen, adding the intermediate C-I (1.0 eq), pd (OAc) 2 (0.01eq)、Pcy 3 (0.02 eq), potassium carbonate (3.0 eq) and DMF solvent, and reacting at 150 ℃ for 12h; after completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate; with magnesium sulfateThe resulting organic layer was dried and the solvent was removed therefrom by a rotary evaporator, and the organic layer was purified by evaporation with dichloromethane: the volume ratio of petroleum ether is 1: (1-9) as an eluent, and purifying by using a chromatographic column to obtain the phosphorescent compound with the structural general formula I.
Another object of the embodiments of the present invention is to provide a phosphorescent compound prepared by the above method.
Another object of an embodiment of the present invention is to provide an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, where the organic layer includes a light-emitting layer, the light-emitting layer includes a host material and a dopant material, and the phosphorescent compound is used as the host material. The organic electroluminescent device is manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate, and can be manufactured by the following conventional methods: physical Vapor Deposition (PVD) methods such as sputtering or electron beam evaporation.
As another preferable mode of the embodiment of the present invention, at least one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer are provided between the anode and the cathode.
Among them, the anode preferably includes a material having a high work function, such as Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO).
The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and has high hole mobility.
The electron blocking layer may be disposed between the hole transport layer and the light emitting layer.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons.
Preferably, the light emitting layer comprises a host material and a dopant material; the mass ratio of the main material to the doping material is 90-99.5:0.5-10;
preferably, the host material is divided into a phosphorescent host material and a fluorescent host material, and the phosphorescent compound is preferably used as the phosphorescent host material.
The doping material may include fluorescent doping and phosphorescent doping.
The phosphorescent dopant material includes a phosphorescent material of a metal complex of iridium, platinum, or the like. For example, ir (ppy) 3 Isogreen phosphorescent materials, FIrpic, FIr 6 Iso-blue phosphorescent material and Btp 2 Red phosphorescent materials such as Ir (acac).
As the hole-blocking layer material, a compound having a hole-blocking effect known in the art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but the invention is not limited thereto.
The electron transport layer may function to facilitate electron transport. Compounds having an electron transporting action well known in the art, for example, al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; hydroxyflavone-metal complexes, and the like.
The electron injection layer may function to promote electron injection. Has the ability of transporting electrons and prevents excitons generated in the light emitting layer from migrating to the hole injection layer.
The cathode is preferably a material having a small work function so that electrons are smoothly injected into the organic material layer. Such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
compared with the existing phosphorescent material, the organic electroluminescent device prepared by adopting the phosphorescent compound as the main material has the advantages that the driving voltage, the luminous efficiency, the service life and the glass transition temperature are all improved, and the practicability of the organic electroluminescent device can be improved. In addition, the preparation method of the phosphorescent compound provided by the embodiment of the invention has the advantages of simple synthesis process and higher product yield.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
Specific implementations of the present invention are described in detail below with reference to specific embodiments.
Example 1 Synthesis of phosphorescent Compound 1
This example provides a phosphorescent compound, which is prepared as follows:
Figure BDA0003251808870000171
(1) In a reaction flask, under nitrogen protection, add reactant A-1 (100 mmol), reactant B-1 (220 mmol), tetrakis (triphenylphosphine palladium) (1 mmol), toluene: ethanol: water =600mL:400mL:400mL of potassium carbonate (250 mmol) and reacting at the temperature of 80 ℃ for 8h; after the reaction was completed, it was cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain intermediate C-1 (56.5g, ms;
(2) In a reaction flask, under the protection of nitrogen, adding intermediate C-1 (70 mmol), pd (OAc) 2 (0.07mmol)，Pcy 3 (1.4 mmol), potassium carbonate (210 mmol) and DMF (700 mL) at 150 ℃ for 12h; after completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate; the resulting organic layer was then dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator, and the organic layer was purified by evaporation with dichloromethane: the volume ratio of petroleum ether is 1: (1-9) as an eluent, and purification by a column chromatography gave phosphorescent compound 1 (39.3 g, yield: 86%).
The phosphorescent compound 1 thus obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: theoretical value 652.80; the test value was 652.68.
Elemental analysis (unit:%):
theoretical value: c,86.48; h,4.94; n,8.58;
test values are: c,86.49; h,4.93; and N,8.58.
Example 2 Synthesis of phosphorescent Compound 52
Figure BDA0003251808870000181
(1) In a reaction flask, under nitrogen protection, add reactant a-52 (100 mmol), reactant B-52 (220 mmol), tetrakis (triphenylphosphine palladium) (1 mmol), toluene: ethanol: water =600mL:400mL:400mL of potassium carbonate (250 mmol) and reacting at the temperature of 80 ℃ for 8h; after the reaction was completed, it was cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain intermediate C-52 (73.2g, ms 915.31, yield: 80%);
(2) In a reaction flask, under the protection of nitrogen, the intermediate C-52 (70 mmol), pd (OAc) is added 2 (0.07mmol)，Pcy 3 (1.4 mmol), potassium carbonate (210 mmol) and DMF (700 mL) at 150 ℃ for 12h; after completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate; the resulting organic layer was then dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator, and the organic layer was purified by evaporation with dichloromethane: the volume ratio of petroleum ether is 1: (1-9) as an eluent, and purification by a column chromatography gave phosphorescent compound 52 (51.8 g, yield: 84%).
The compound 52 thus obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: theoretical value is 880.07; the test value was 880.42.
Elemental analysis (unit:%):
theoretical value: c,87.35; h,4.70; n,7.96;
test values are: c,87.33; h,4.70; and N,7.94.
Example 3 Synthesis of phosphorescent Compound 100
Figure BDA0003251808870000191
(1) In a reaction flask, under nitrogen protection, add reactant a-100 (100 mmol), reactant B-100 (220 mmol), tetrakis (triphenylphosphine palladium) (1 mmol), toluene: ethanol: water =600mL:400mL:400mL of potassium carbonate (250 mmol) and reacting at the temperature of 80 ℃ for 8h; after the reaction was completed, it was cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain intermediate C-100 (49.0 g, ms;
(2) In a reaction flask, under the protection of nitrogen, adding intermediate C-100 (70 mmol), pd (OAc) 2 (0.07mmol)，Pcy 3 (1.4 mmol), potassium carbonate (210 mmol) and DMF (700 mL) at 150 ℃ for 12h; after completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate; the resulting organic layer was then dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator, and the organic layer was purified by evaporation with dichloromethane: the volume ratio of petroleum ether is 1: (1-9) as an eluent, and purification by a column chromatography gave phosphorescent compound 100 (33.2 g, yield: 80%).
The obtained phosphorescent compound 100 was subjected to detection analysis, and the results were as follows:
mass spectrometry test: theoretical value is 592.72; the test value was 592.54.
Elemental analysis (unit:%):
theoretical value: c,81.06; h,4.08; n,9.45; s,5.41
Test values are: c,81.07; h,4.08; n,9.44; and S,5.40.
Example 4 Synthesis of phosphorescent Compound 121
Figure BDA0003251808870000201
(1) In a reaction flask, under nitrogen protection, add reactant a-121 (100 mmol), reactant B-121 (220 mmol), tetrakis (triphenylphosphine palladium) (1 mmol), toluene: ethanol: water =600mL:400mL:400mL of potassium carbonate (250 mmol) and reacting at the temperature of 80 ℃ for 8h; after the reaction was completed, it was cooled to room temperature, filtered, and the obtained solid was purified by recrystallization from toluene to obtain intermediate C-121 (62.6 g, ms 813.27, yield: 77%);
(2) In a reaction flask, under the protection of nitrogen, the intermediate C-121 (70 mmol), pd (OAc) is added 2 (0.07mmol)，Pcy 3 (1.4 mmol), potassium carbonate (210 mmol) and DMF (700 mL) at 150 ℃ for 12h; after completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate; the resulting organic layer was then dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator, and the organic layer was purified by evaporation with dichloromethane: the volume ratio of petroleum ether is 1: (1-9) as an eluent, and purification by a column chromatography gave phosphorescent compound 121 (44.1 g, yield: 81%).
The obtained phosphorescent compound 121 was subjected to detection analysis, and the results were as follows:
mass spectrometry test: theoretical value is 777.29; the test value was 777.21.
Elemental analysis (unit:%):
theoretical value: c,86.46; h,4.54; n,9.00;
test values are: c,86.45; h,4.55; and N,9.01.
Examples 5 to 30
Since the general structural formula is the general formula I in the summary of the invention, the synthetic routes and principles of the preparation methods of other phosphorescent compounds are the same as those of the above-listed example 1, and only the raw materials need to be replaced with the corresponding reactants of the target products, and the amounts of the reactants are adjusted according to the corresponding stoichiometric ratios, so that the corresponding phosphorescent compounds can be obtained, which are not exhaustive, the present invention examples refer to the preparation methods of examples 1 to 4 to complete the synthesis of the phosphorescent compounds 4, 8, 13, 18, 23, 30, 36, 44, 50, 56, 62, 70, 76, 82, 89, 95, 99, 106, 110, 116, 120, 124, 130, 136, 144 and 150, and the mass spectra, the molecular formulas and the yields are shown in table 1.
TABLE 1
Examples Phosphorescent compounds Molecular formula Theoretical value of mass spectrum Mass spectrometric test values Yield%
Example 5 4 C 44 H 26 N 4 610.72 610.34 78
Example 6 8 C 45 H 28 N 4 624.75 624.81 79
Example 7 13 C 45 H 27 N 3 609.73 609.57 86
Example 8 18 C 48 H 28 N 4 660.78 660.58 82
Example 9 23 C 49 H 29 N 5 687.81 687.84 84
Example 10 30 C 57 H 33 N 5 O 803.93 803.33 86
Example 11 36 C 52 H 32 N 4 712.86 712.62 86
Example 12 44 C 37 H 21 N 3 507.60 507.41 82
Example 13 50 C 65 H 39 N 7 918.08 918.47 82
Example 14 56 C 53 H 33 N 3 711.87 711.47 85
Example 15 62 C 44 H 26 N 4 610.72 610.75 79
Example 16 70 C 62 H 37 N 5 O 868.01 868.78 85
Example 17 76 C 57 H 33 N 5 OS 835.99 835.45 80
Example 18 82 C 45 H 28 N 4 S 656.81 642.74 81
Example 19 89 C 61 H 37 N 7 S 900.08 900.07 80
Example 20 95 C 61 H 37 N 5 S 872.06 872.14 80
Example 21 99 C 41 H 25 N 3 S 591.73 591.47 84
Example 22 106 C 44 H 26 N 4 S 642.78 642.65 84
Example 23 110 C 68 H 43 N 5 O 946.13 896.48 84
Example 24 116 C 63 H 38 N 6 S 911.10 911.20 78
Example 25 120 C 52 H 31 N 7 753.87 753.51 86
Example 26 124 C 58 H 37 N 5 803.97 803.65 81
Example 27 130 C 47 H 32 N 4 652.80 652.47 82
Example 28 136 C 61 H 38 N 6 S 887.08 887.53 84
Example 29 144 C 49 H 32 N 4 S 708.88 708.62 80
Example 30 150 C 50 H 28 N 6 712.82 712.80 81
In addition, it should be noted that other phosphorescent compounds of the present application can be obtained by the preparation method according to the above-mentioned examples, and therefore, they are not listed here.
Device example 1:
the embodiment of the device provides an organic electroluminescent device, and the specific preparation method comprises the following steps:
(1) An ITO/Ag/ITO film (the thickness of ITO is 14nm, the thickness of Ag is 150 nm) used on a glass substrate of an OLED device is put into distilled water to be cleaned for 2 times, and ultrasonic washing is carried out for 30 minutes each time; then repeatedly washing with distilled water for 2 times, and washing with ultrasonic wave for 10 minutes each time; after the cleaning with distilled water is finished, respectively washing the raw materials with ultrasonic waves in solvents such as isopropanol, acetone and methanol in sequence and then drying the raw materials; then, the mixture was washed for 5 minutes by a plasma cleaner and then sent to an evaporator.
(2) The compounds HT and P-dose (3%) were introduced into the cell of the vacuum vapor deposition apparatus, and then the pressure in the cell of the apparatus was controlled to 10 -6 And (7) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 10nm on the ITO substrate. Next, the compound HT was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a hole transport layer having a thickness of 130nm on the hole injection layer.
(3) Then, the compound EBL was introduced into the cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming an electron blocking layer having a thickness of 10nm on the hole transport layer. The phosphorescent compound 1 provided in example 1 was introduced into one cell of a vacuum vapor deposition apparatus as a phosphorescent host, and the compound Dopant was introduced into the other cell as a phosphorescent Dopant material. The doping ratio of the phosphorescent host material and the phosphorescent dopant material is 97: and 3, forming a light-emitting layer with the thickness of 20nm on the electron blocking layer.
(4) Performing vacuum evaporation on the luminescent layer to obtain ET and Liq as electron transport layers (35nm, 50%); yb with a thickness of 1.0nm was vacuum-deposited on the electron transport layer to form an electron injection layer. And (3) performing vacuum evaporation on the electron injection layer to form magnesium and silver as cathodes, wherein the weight ratio of the magnesium to the silver is 1: and 9, evaporating a CPL layer on the cathode in vacuum with the thickness of 18nm to obtain an organic electroluminescent device, wherein the evaporation thickness is 70 nm.
The structure of the prepared organic electroluminescent device is as follows:
ITO/Ag/ITO/HT: p-dopant (10nm, 3%)/HT (130 nm)/EBL (10 nm)/Compound 1: dopan (20nm, 2%)/ET: liq (35nm, 50%)/Yb (1 nm)/Mg: ag (18nm, 1.
Wherein, the chemical structural formula of the partial raw materials is as follows:
Figure BDA0003251808870000241
device example 2-device example 156
By referring to the above-mentioned methods, the compound 1 used in device example 1 was replaced with the compounds 2 to 156, respectively, as electron transport layers, to prepare corresponding organic electroluminescent devices.
Comparative device example 1 to comparative device example 4
By referring to the above-mentioned methods, the compound 1 used in device example 1 was replaced with comparative compounds 1 to 4, respectively, to prepare corresponding organic electroluminescent devices.
Figure BDA0003251808870000242
Figure BDA0003251808870000251
The organic electroluminescent device prepared above was applied with forward DC bias voltage, and the organic electroluminescent characteristics were measured at a luminance of 6000cd/m using PR-650 photometry equipment of Photo Research corporation 2 The lifetime of T95 was measured under the conditions using a lifetime measuring apparatus available from McScience. The results are shown in Table 2.
TABLE 2
Figure BDA0003251808870000252
Figure BDA0003251808870000261
Figure BDA0003251808870000271
Figure BDA0003251808870000281
Figure BDA0003251808870000291
As can be seen from Table 2, the organic electroluminescent devices prepared using the phosphorescent compounds of the present invention as host materials have improved properties in terms of driving voltage, luminous efficiency, lifetime, and glass transition temperature, as compared to the organic electroluminescent devices prepared using the comparative compounds 1 to 4.
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 and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.

Claims (7)

1. A phosphorescent compound, wherein the phosphorescent compound has a general structural formula of formula I:
Figure FDA0003749955670000011
wherein R is 1 、R 2 、R 3 、R 4 Each independently is hydrogen;
x is O, S, CR 5 R 6 Or NR 7 ；
R 5 、R 6 Each independently is C1-C6 alkyl, C6-C30 aryl, or C3-C30 heteroaryl;
R、R 7 each independently is a C6-C30 aryl or C3-C20 heteroaryl;
R 1 -R 4 the substituted position is any position on the benzene ring, and the number of the substituted positions is an integer of 0-4.
2. The phosphorescent compound according to claim 1, wherein the structural formula of the phosphorescent compound is from formula I-1 to formula I-8
Figure FDA0003749955670000012
3. The phosphorescent compound according to claim 1, wherein R is 5 、R 6 Each independently is methyl, ethyl, propyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; r 7 Phenyl, naphthyl, biphenyl.
4. The phosphorescent compound according to claim 1, wherein R is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, an anthracyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a fluoranthenyl group, a triazinyl group, a pyrimidinyl group, a pyridyl group, a quinazolinyl group, a quinolyl group or a quinoxalinyl group, and any one of the following groups:
Figure FDA0003749955670000021
Figure FDA0003749955670000031
Figure FDA0003749955670000041
5. the phosphorescent compound of claim 1, wherein the chemical structural formula of the phosphorescent compound is one of the following:
Figure FDA0003749955670000042
Figure FDA0003749955670000051
Figure FDA0003749955670000061
Figure FDA0003749955670000071
Figure FDA0003749955670000081
6. a method for preparing a phosphorescent compound according to any one of claims 1 to 5, wherein the synthesis route is:
Figure FDA0003749955670000082
the method specifically comprises the following steps:
under the protective atmosphere, placing a reactant A-I, a reactant B-I, tetrakis (triphenylphosphine palladium) and potassium carbonate in a solvent for reaction; after the reaction is finished, purifying the obtained product to obtain an intermediate C-I;
under a protective atmosphere, the intermediate C-I, pd (OAc) is added 2 、Pcy 3 And potassium carbonate, put into solvent and react; after the reaction is finished, the mixture is washed and extracted, and the obtained organic layer is eluted and purified to obtain the phosphorescent compound with the general structural formula I.
7. An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, the organic layer comprising an emission layer comprising a host material and a dopant material, the phosphorescent compound according to any one of claims 1 to 5 as the host material; at least one or more layers of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer are arranged between the anode and the cathode.
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