CN110746401A - Phosphorescent compound and organic light emitting diode device using the same - Google Patents

Phosphorescent compound and organic light emitting diode device using the same Download PDF

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CN110746401A
CN110746401A CN201910857812.0A CN201910857812A CN110746401A CN 110746401 A CN110746401 A CN 110746401A CN 201910857812 A CN201910857812 A CN 201910857812A CN 110746401 A CN110746401 A CN 110746401A
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phosphorescent compound
light emitting
phosphorescent
emitting diode
independently selected
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郑贤哲
赵晓宇
华万鸣
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Zhejiang Hua Hui Photoelectric Technology Co Ltd
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Abstract

The present invention relates to a phosphorescent compound and an organic light emitting diode device using the same, and more particularly, to a phosphorescent compound and an organic light emitting diode device using the sameAnd a soluble phosphorescent host compound having excellent color purity and high luminance and luminous efficiency and an OLED device using the same. A phosphorescent compound characterized by: the structural formula is shown as formula 1 or formula 2,
Figure DDA0002195807120000011
the present invention uses the phosphorescent compounds represented by structural formulae 1 and 2 as the light emitting layer of the organic light emitting diode device, having excellent color purity and brightness and prolonged durability effect.

Description

Phosphorescent compound and organic light emitting diode device using the same
Technical Field
The present invention relates to a phosphorescent compound and an organic light emitting diode device using the same, and more particularly, to a soluble phosphorescent host compound having excellent color purity and high luminance and light emitting efficiency and an OLED device using the same.
Background
Recently, the demand for flat panel displays (e.g., liquid crystal displays and plasma display panels) is increasing. However, these flat panel displays have a lower response time and a narrower viewing angle than Cathode Ray Tubes (CRTs).
An Organic Light Emitting Diode (OLED) device is one of the next-generation flat panel displays that can solve the above problems and have a small footprint.
The elements of the OLED device may be formed on a flexible substrate, such as a plastic substrate. In addition, OLED devices have advantages in view angle, driving voltage, power consumption, and color purity. Outside, the OLED device is sufficient to produce full color images.
In general, a light emitting diode of an OLED device includes an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Emitting Material Layer (EML), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode.
The OLED device emits light by: electrons and holes are injected into the light emitting compound layer from the cathode as an electron injection electrode and from the anode as a hole injection electrode, respectively, so that the electrons and the holes are recombined to generate excitons, and the excitons are made to transition from an excited state to a ground state.
The principle of 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.
When the light emitting material layer emits light corresponding to the energy band gap, singlet excitons having 0 spin and triplet excitons having 1 spin are generated in a ratio of 1: 3. The ground state of the organic material is a singlet state, which allows singlet excitons to transition to the ground state with accompanying light emission. However, since the triplet excitons cannot undergo transition accompanied by light emission, the internal quantum efficiency of the OLED device using the fluorescent material is limited to within 25%.
On the other hand, if the spin orbit coupling momentum is high, the singlet state and the triplet state are mixed so that an intersystem crossing occurs between the singlet state and the triplet state, and the triplet exciton may also transition to the ground state with accompanying light emission. The phosphorescent material may use triplet excitons and singlet excitons, so that an OLED device using the phosphorescent material may have an internal quantum efficiency of 100%.
Recently, iridium complexes, such as bis (2-phenylquinoline) (acetylacetonate) iridium (iii) (Ir (2-phq)2(acac)), bis (2-benzo [ b ] thiophen-2-ylpyridine) (acetylacetonate) iridium (iii) (Ir (btp)2(acac)), and tris (2-phenylquinoline) iridium (iii) Ir (2-phq)3 dopants have been introduced.
In order to obtain high current luminous efficiency (Cd/a) using a phosphorescent material, excellent internal quantum efficiency, high color purity, and long lifetime are required. In particular, referring to fig. 1, the higher the color purity, i.e., the higher cie (x), the worse the color sensitivity. As a result, it is very difficult to obtain light emission efficiency at high internal quantum efficiency. Therefore, there is a need for novel red phosphorescent compounds having excellent color purity (CIE (X) ≧ 0.65) and high luminous efficiency.
On the other hand, in addition to the iridium complex described above, for example, 4,4-N, N-Carbazole Biphenyl (CBP) or other metal complexes are used as the red phosphorescent compound. However, these compounds do not have ideal solubility in a solvent, and thus cannot form a light emitting layer by a solution process. The light emitting layer should be formed through a deposition process, and thus, the manufacturing process is very complicated and the process efficiency is very low. In addition, the amount of waste material in the deposition process is very large, resulting in increased production costs.
Disclosure of Invention
The present invention is directed to provide a phosphorescent compound and an organic light emitting diode device using the same to solve the disadvantages of the related art.
The technical scheme adopted by the invention for solving the technical problem is as follows:
a phosphorescent compound characterized by: the structural formula is shown as formula 1 and formula 2,
Figure BDA0002195807100000031
ar in the above formulae 1 and 21Independently selected from H, C6-C60 aryl, fluorenyl, C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, C3-C60 alicyclic and C6-C60 aromatic ring condensed ring group, C2-C20 alkenyl and C2-C20 alkynyl. L1 and L2 are independently selected from one of single bond, C6-C60 arylene group and fluorenylene group, C3-C60 alicyclic ring and C6-C60 aromatic ring condensed ring group, and C2-C60 heterocyclic group. X1-X2 are independently selected from N atoms or C atoms, wherein at least one of X1-X2 is N. Wherein ring A and ring B are selected from H, substituted or unsubstituted C6-C60 aryl. Further, Ar is2And Ar3One selected from H, C6-C60 aryl, fluorenyl, C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, C3-C60 alicyclic and C6-C60 aromatic ring condensed ring group, C2-C20 alkenyl and C2-C20 alkynyl.
Further, the structural formula 1 and the structural formula 2 are independently selected from compounds of any one of the following formulas 3 to 6:
Figure BDA0002195807100000041
further, the phosphorescent compound is independently selected from the following compounds:
Figure BDA0002195807100000051
Figure BDA0002195807100000061
Figure BDA0002195807100000071
Figure BDA0002195807100000081
Figure BDA0002195807100000091
Figure BDA0002195807100000101
Figure BDA0002195807100000121
Figure BDA0002195807100000141
Figure BDA0002195807100000151
Figure BDA0002195807100000161
Figure BDA0002195807100000171
Figure BDA0002195807100000181
Figure BDA0002195807100000191
Figure BDA0002195807100000201
Figure BDA0002195807100000211
Figure BDA0002195807100000231
Figure BDA0002195807100000241
Figure BDA0002195807100000271
Figure BDA0002195807100000281
Figure BDA0002195807100000291
further, 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 deposited in sequence, and the phosphorescent compound is used as a main material of the light emitting layer.
The invention has the advantages that: the present invention uses the phosphorescent compounds represented by formulas 1 and 2 as the light emitting layer of the organic light emitting diode device, having excellent color purity and luminance and a prolonged durability effect.
Drawings
FIG. 1 is a graph of chromaticity and visibility of light emitted from an organic electroluminescent diode.
FIG. 2 is a structural formula of compounds copper (II) phthalocyanine (CuPc), NPB, (mxmq)2Ir (acac), Alq3 and CBP used in an embodiment of the present invention.
Detailed Description
In order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further described with reference to the figures and the specific embodiments.
As the red phosphorescent compounds with the structural formulas shown as formula 1 and formula 2 have excellent color purity, high brightness and excellent luminous efficiency, the technical scheme and the achieved technical effects provided by the invention are proved by taking preparation methods and test results of RH-001, RH-017, RH-032, RH-061, RH-241 and RH-481 as examples.
In the following embodiments, NPB is 4,4 ' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl, CBP is 4,4 ' -N, N ' -dicarbakisbiphenyl, CuPc is copper phthalocyanine, LiF lithium fluoride, ITO is indium tin oxide, and Alq3 is tris (8-hydroxyquinoline) aluminum.
LC-MS, liquid chromatography-mass spectrometer, M/Z: ratio of number of protons/number of charges.
Examples of formation
1.1. Synthesis of intermediate Sub-1:
Figure BDA0002195807100000311
a2000 mL reaction flask was charged with 2-bromonitrobenzene (150.0g,742.5mmol), 2-aminophenylboronic acid pinacol ester (179.0g,816.8mmol), and tetrakis(triphenylphosphine) palladium (5 mol%), sodium bicarbonate (187.1g,2227.4mmol), ethylene glycol dimethyl ether (1200mL) and water (200 mL). The reaction system is heated to 90 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was passed through a silica gel column to obtain an intermediate, Sub-1(133.6g, yield 84%), LC-MS: M/Z215.2 (M + H)+。
2. Synthesis of intermediate Sub-2:
Figure BDA0002195807100000312
a2000 mL reaction flask was charged with a mixture of intermediate Sub-1(130.0g,606.9mmol), water (800mL) and concentrated hydrochloric acid (200mL) and heated to 60 ℃ to give a clear solution. The mixture was diazotized at 5 ℃ by addition of an aqueous solution (150mL) of sodium nitrite (46.1g,667.5 mmol). After stirring for 30 minutes, an aqueous solution (300mL) of potassium iodide (120.9g,728.2mmol) was added rapidly to the mixture, which was then heated slowly to boiling point and refluxed for 6 hours. After the reaction was completed, it was cooled to room temperature. The mixture was quenched by addition of saturated sodium sulfate solution and the pH was adjusted to 8-10 with saturated aqueous sodium hydroxide solution. The combined organic solvents were extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. Chromatography (ethyl acetate/petroleum ether-1/30) gave intermediate Sub-2(153.9g, 78% yield). LC-MS M/Z326.1(M + H)+。
3. Synthesis of intermediate Sub-3:
after intermediate Sub-2(150.0g,461.4mmol) in dry dichloromethane (1500mL), m-chloroperoxybenzoic acid (119.4g,692.1mmol) and trifluoromethanesulfonic acid (122.5mL,1384.2mmol) were added with stirring. The above mixture was stirred at room temperature for 2 hours. The dichloromethane was removed by rotary evaporation, then diethyl ether was added and the mixture stirred for 30 minutes and filtered. The collected solid was washed three times with ether and dried in vacuo to give intermediate Sub-3(172.4g, yield 79%). LC-MS: M/Z474.2(M+H)+。
4. Synthesis of intermediate Sub-4:
Figure BDA0002195807100000322
a2000 mL three-necked flask was charged with intermediate Sub-3(170.0g,359.3mmol), naphthalene-1, 8-diboronic acid (78.2g,395.2mmol), palladium acetate (10 mol%), potassium carbonate (124.1g,898.3mmol), ethylene glycol dimethyl ether (1000mL) and water (450 mL). The reaction system is heated to 120 ℃ and reacts for 14 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was then passed through a silica gel column to give intermediate Sub-4(41.8g, yield 36%). LC-MS: M/Z324.3 (M + H)+。
5. Synthesis of intermediate Sub-5:
Figure BDA0002195807100000331
a500 mL reaction flask was charged with intermediate Sub-4(40.0g,123.7mmol) and triethyl phosphite (200 mL). The reaction system is heated to 80 ℃ and reacts for 18 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product which was passed through a silica gel column to give an intermediate, Sub-5(20.9g, yield 58%), LC-MS: M/Z292.4 (M + H)+。
Synthesis of RH-001:
a250 mL three-necked flask was charged with intermediate I-1(3.0g,12.5mmol), intermediate Sub-5(4.0g,13.7mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (4.2g,37.4mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and concentratedThe crude product thus obtained was passed through a silica gel column to obtain RH-001(4.7g, yield 76%). LC-MS: M/Z496.6 (M + H)+。
Synthesis of RH-017:
Figure BDA0002195807100000341
a250 mL three-necked flask was charged with intermediate I-2(3.0g,7.6mmol), intermediate Sub-5(2.4g,8.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (2.6g,22.7mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 14 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through a silica gel column to give RH-017(3.6g, yield 72%). LC-MS: M/Z651.7 (M + H)+。
Synthesis of RH-032:
Figure BDA0002195807100000342
a250 mL three-necked flask was charged with intermediate I-3(3.0g,9.5mmol), intermediate Sub-5(3.0g,10.4mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.2g,28.4mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain RH-032(4.1g, yield 75%). LC-MS: M/Z572.7 (M + H)+。
Synthesis of RH-061:
Figure BDA0002195807100000351
a250 mL three-necked flask was charged with intermediate I-4(3.0g,12.5mmol), intermediate Sub-5(4.0g,13.7mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (4.2g,37.4mmol) and o-xylene (80 mL). Reaction System literThe temperature is raised to 120 ℃, and the reaction is carried out for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain RH-061(4.4g, yield 71%). LC-MS: M/Z496.6 (M + H)+。
Synthesis of RH-241:
Figure BDA0002195807100000352
a250 mL three-necked flask was charged with intermediate I-5(3.0g,10.3mmol), intermediate Sub-5(3.3g,11.3mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.5g,31.0mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 14 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain RH-241(4.1g, yield 73%). LC-MS: M/Z546.6 (M + H)+。
Synthesis of RH-481:
Figure BDA0002195807100000361
a250 mL three-necked flask was charged with intermediate I-6(3.0g,8.8mmol), intermediate Sub-5(2.8g,9.7mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.0g,26.4mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 14 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was then passed through a silica gel column to give RH-481(3.7g, yield 70%). LC-MS: M/Z596.7 (M + H)+。
Detailed description of the preferred embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
Subsequently placing the substrateIn a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrate
Figure BDA0002195807100000362
NPB
Figure BDA0002195807100000363
RH-001+(mxmq)2Ir(acac)((5％)
Figure BDA0002195807100000364
Alq3
Figure BDA0002195807100000365
LiF
Figure BDA0002195807100000366
And Al
Figure BDA0002195807100000367
The sequence of (a) and (b) forming layers of organic material. At 0.9mA, the brightness was equal to 1789d/m2 (5.3V). In this case, CIEx is 0.657 and CIEy is 0.341.
2. Second embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrateNPB
Figure BDA0002195807100000369
RH-017+(mxmq)2Ir(acac)(5％)
Figure BDA00021958071000003610
Alq3
Figure BDA0002195807100000371
LiF
Figure BDA0002195807100000372
And Al
Figure BDA0002195807100000373
The sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1711cd/m2(5.4V). At this time, CIEx is 0.658 and CIEy is 0.341.
3. Third embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrate
Figure BDA00021958071000003710
NPB
Figure BDA00021958071000003711
RH-032+(mxmq)2Ir(acac)(5％)Alq3LiF
Figure BDA00021958071000003714
And Al
Figure BDA00021958071000003715
The sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1768cd/m2(5.3V). At this time, CIEx is 0.658 and CIEy is 0.340.
4. Fourth embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrate
Figure BDA00021958071000003716
NPB
Figure BDA00021958071000003717
RH-061+(mxmq)2Ir(acac)(5％)
Figure BDA00021958071000003718
Alq3
Figure BDA00021958071000003719
LiF
Figure BDA00021958071000003720
And AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1752cd/m2(5.3V). In this case, CIEx is 0.657 and CIEy is 0.341.
5. Fifth embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrate
Figure BDA0002195807100000374
NPB
Figure BDA0002195807100000375
RH-241+(mxmq)2Ir(acac)(5％)Alq3
Figure BDA0002195807100000377
LiF
Figure BDA0002195807100000378
And Al
Figure BDA0002195807100000379
To form organic matterA layer of material. At 0.9mA, the luminance is equal to 1739cd/m2(5.4V). In this case, CIEx is 0.657 and CIEy is 0.341.
6. Sixth embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, CuPc was applied onto the ITO substrate
Figure BDA0002195807100000381
NPB
Figure BDA0002195807100000382
RH-481+(mxmq)2Ir(acac)(5％)
Figure BDA0002195807100000383
Alq3
Figure BDA0002195807100000384
LiF
Figure BDA0002195807100000385
And Al
Figure BDA0002195807100000386
The sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1698cd/m2(5.5V). At this time, CIEx is 0.658 and CIEy is 0.341.
7. Comparative example
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Using CuPc on ITO substrate
Figure BDA0002195807100000387
NPB
Figure BDA0002195807100000388
CPB+(mxmq)2Ir(acac)(5％)
Figure BDA0002195807100000389
Alq3
Figure BDA00021958071000003810
LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance was equal to 1409cd/m2(5.7V). In this case, CIEx is 0.657 and CIEy is 0.341.
It is shown in fig. 1 that the color purity of the organic electroluminescent device increases (i.e., the X value becomes larger as the chromaticity coordinate becomes larger) and the visibility decreases.
The characteristics of efficiency, chromaticity coordinates, and luminance according to the above-described embodiments and comparative examples are shown in table 1 below.
TABLE 1
Figure BDA00021958071000003813
Figure BDA0002195807100000391
As shown in table 1, the device operates at high efficiency at low voltage even when the color purity is high. Also, the current efficiency of the second embodiment is increased by 20% or more compared to the comparative example.
The foregoing shows and describes the general principles, essential 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 (4)

1. A phosphorescent compound characterized by: the structural formula is shown as formula 1 or formula 2,
Figure FDA0002195807090000011
ar1 in the formulas 1 and 2 is independently selected from one of C6-C60 aryl, fluorenyl, C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, C3-C60 alicyclic and C6-C60 aromatic ring condensed ring group, C2-C20 alkenyl and C2-C20 alkynyl; l1 and L2 are respectively and independently selected from one of a single bond, C6-C60 arylene and fluorenylene, C3-C60 alicyclic and C6-C60 aromatic ring condensed ring group, and C2-C60 heterocyclic group; X1-X2 are independently selected from N atoms or C atoms, wherein at least one of X1-X2 is N;
wherein ring A and ring B are selected from H, substituted or unsubstituted C6-C60 aryl;
wherein Ar is2And Ar3One selected from H, C6-C60 aryl, fluorenyl, C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, C3-C60 alicyclic and C6-C60 aromatic ring condensed ring group, C2-C20 alkenyl and C2-C20 alkynyl.
2. The phosphorescent compound according to any one of claim 1, wherein the formulae 1 and 2 are independently selected from any one of the structures of formulae 3 to 6:
Figure FDA0002195807090000012
3. the phosphorescent compound according to any one of claims 1 to 2, wherein: the phosphorescent compounds are independently selected from the following compounds:
Figure FDA0002195807090000021
Figure FDA0002195807090000031
Figure FDA0002195807090000041
Figure FDA0002195807090000051
Figure FDA0002195807090000061
Figure FDA0002195807090000071
Figure FDA0002195807090000091
Figure FDA0002195807090000101
Figure FDA0002195807090000121
Figure FDA0002195807090000131
Figure FDA0002195807090000141
Figure FDA0002195807090000151
Figure FDA0002195807090000161
Figure FDA0002195807090000171
Figure FDA0002195807090000181
Figure FDA0002195807090000211
Figure FDA0002195807090000231
Figure FDA0002195807090000241
Figure FDA0002195807090000261
4. an organic electroluminescent diode device using the phosphorescent compound according to any one of claims 1 to 3, characterized in that: the organic electroluminescent device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode, and the phosphorescent compound is used as a main material of the luminescent layer.
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