A green phosphorescent dopant material, a preparation method thereof and an organic electroluminescent device

Abstract

The application provides a kind of green phosphorescent dopant material and its preparation method, organic electroluminescent device and organic electroluminescent device, the structural general formula of the green phosphorescent dopant material is chemical formula I, the green phosphorescent dopant material of the application introduces the OCN four-tooth ligand structure containing platinum, can effectively improve the stability of compound, further connects silane group on the parent core, the group has huge steric hindrance, hinders the close approach between Pt complex core plane, effectively weakens intermolecular pi-pi stacking effect, significantly reduces concentration quenching effect, more helps to improve carrier capture efficiency, improves device efficiency.The material of the application can obtain the device with higher luminous efficiency and longer service life while maintaining low driving voltage.

Description

TECHNICAL FIELD

[0001] The present application belongs to the field of organic electroluminescence, and relates to a green phosphorescent dopant material, a preparation method thereof, an organic electroluminescent device and an organic electroluminescent apparatus. BACKGROUND

[0002] It has been shown by research that transition metal complexes can be applied to phosphorescent OLEDs (phosphorescent OLEDs), and the phosphorescent material has a strong self-orbital coupling effect, which can utilize singlet and triplet excitons at the same time, so that the internal quantum efficiency of the phosphorescent electroluminescent device theoretically reaches 100%. Metal complex luminescent materials have been applied in the industry, and traditional industrialized phosphorescent OLED light-emitting layer dopant materials mainly use metal iridium complexes. However, metal platinum has a natural advantage over iridium in terms of price, and the complexes have excellent material stability due to their planarity, which has been greatly developed in recent years. In recent years, metal platinum complexes have shown properties that surpass iridium complexes. The synthesis steps of platinum complexes with ONCN tetradentate ligands are simple, and there are many modifiable sites, which can greatly improve the space. However, this structure is also prone to intermolecular π-π stacking interactions. This close packing can lead to exciton annihilation, and the excited states of adjacent molecules collide and deactivate, converting energy into heat or vibrational energy rather than emitting light (concentration quenching). It can also form excimers or excited state complexes, resulting in red shift and broadening of the emission spectrum, and reducing color purity. Therefore, it is an urgent need in the industry to develop a metal Pt complex as a green phosphorescent dopant material to achieve higher efficiency and longer service life of the device. SUMMARY

[0003] In view of the deficiencies of the prior art, the purpose of the present application is to provide a green phosphorescent dopant material, a preparation method thereof and an organic electroluminescent device. The green phosphorescent dopant material of the present application introduces an ONCN tetradentate ligand structure containing platinum, which can effectively improve the stability of the compound. Further, a silane group is connected to the parent nucleus. This group has a large steric hindrance, which prevents the close approach of the Pt complex core planes, effectively reduces the intermolecular π-π stacking interaction, significantly reduces the concentration quenching effect, and is more helpful to improve the carrier capture efficiency and improve the device efficiency. The material of the present application can maintain a low driving voltage while achieving a device with higher luminous efficiency and longer service life.

[0004] To achieve this purpose, the present application adopts the following technical solutions:

[0005] In one aspect, the present application provides a green phosphorescent dopant material, and the structure general formula of the green phosphorescent dopant material is chemical formula I:

[0006] ;

[0007] wherein,

[0008] Ring H is phenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl;

[0009] Ar is selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0010] R1, R2 are independently selected from hydrogen, deuterium, halogen, cyano, TMS (trimethylsilyl), trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C24 aryl;

[0011] R3 is independently selected from hydrogen, deuterium, halogen, cyano, TMS, trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, which contains at least one of the heteroatoms O, S, N, Si or Se;

[0012] n1 is selected from an integer of 0, 1, 2 or 3;

[0013] n2 is selected from an integer of 0, 1, 2, 3 or 4;

[0014] n3 is selected from an integer of 0, 1, 2, 3 or 4;

[0015] R4-R6 are independently selected from deuterium, halogen, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfido, sulfinyl, sulfonyl, phosphino, selenoalkyl, amino, boroalkyl, germanoalkyl, silylalkyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C1-C10 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C1-C10 heteroalkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or combinations thereof;

[0016] R7, R8are independently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C10alkyl, substituted or unsubstituted C1-C10heteroalkyl, substituted or unsubstituted C3-C10cycloalkyl, substituted or unsubstituted C1-C10heterocycloalkyl, substituted or unsubstituted C6-C30aryl, and substituted or unsubstituted C3-C30heteroaryl;

[0017] m is selected from an integer of 0, 1 or 2;

[0018] In the chemical formula I, two of the four bonds to the central metal Pt are coordination bonds and two are covalent bonds, the bond between the metal Pt and the two N is a coordination bond, the bond between Pt and the ring H is a covalent bond, and the bond between Pt and O is a covalent bond;

[0019] The hydrogen involved in the chemical formula I is not deuterated, partially deuterated or fully deuterated.

[0020] Further preferably, the ring H is phenyl;

[0021] Ar is selected from substituted or unsubstituted C6-C24aryl, substituted or unsubstituted C5-C24heteroaryl;

[0022] R1, R2are independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, TMS, trifluoromethyl, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-C6cycloalkyl, substituted or unsubstituted C6-C18aryl;

[0023] R3is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, TMS, trifluoromethyl, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-C6cycloalkyl, substituted or unsubstituted C6-C18aryl, substituted or unsubstituted C5-C24heteroaryl, which contains at least one of O, S, N, Si, Se as a heteroatom;

[0024] R4-R6are independently selected from the group consisting of deuterium, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-C6cycloalkyl, substituted or unsubstituted C1-C6heteroalkyl, substituted or unsubstituted C6-C18aryl, substituted or unsubstituted C5-C24heteroaryl, or a combination thereof;

[0025] R7, R8are independently selected from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C1-C6heteroalkyl, substituted or unsubstituted C3-C6cycloalkyl, substituted or unsubstituted C2-C5heterocycloalkyl, substituted or unsubstituted C6-C18aryl, and substituted or unsubstituted C5-C24heteroaryl.

[0026] The green phosphorescent dopant material further preferably has the general structure according to Formula I-A:

[0027] ;

[0028] wherein Ar1, Ar2are independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, TMS, trifluoromethyl, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C3-C6cycloalkyl, substituted or unsubstituted C6-C18aryl, substituted or unsubstituted C5-C24heteroaryl;

[0029] n9, n 10 are independently selected from the group consisting of 0, 1, 2, 3, 4 or 5.

[0030] Further preferably, R1, R2are independently selected from the group consisting of hydrogen, deuterium, cyano, TMS, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl.

[0031] Further preferred, R3is independently selected from the group consisting of hydrogen, deuterium, cyano, TMS, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisoxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted benzothiadiazolyl.

[0032] Further preferred, R4-R6are independently selected from the group consisting of deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl.

[0033] Further preferred, R7, R8are independently selected from the group consisting of deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl.

[0034] Further preferred, the green phosphorescent dopant material has a general structure of:

[0035] ;

[0036] Further preferred, Ar1, Ar2are independently selected from the group consisting of deuterium, cyano, TMS, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl.

[0037] In the present application, the "substituted" group in the substituted or unsubstituted is selected from one or at least two groups of the following substituents: deuterium, halogen group, cyano group, TMS, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, n-pentyl group, isopentyl group, neopentyl group, t-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, 1-methylhexyl group, cyclopropane, cyclobutane, cyclopentane, cyclohexane, phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorenyl group, dimethylfluorenyl group, phenanthryl group, anthryl group, indenyl group, triphenylene group, pyrenyl group, chrysenyl group, furanyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuranyl group, benzothienyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothienyl group, benzimidazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoisoxazolyl group, benzoxazolyl group, isoindolyl group, indolyl group, benzoindolyl group, benzothiadiazolyl group, carbazolyl group, benzocarbazolyl group, adamantyl group.

[0038] In the above technical solution, the green phosphorescent dopant material is preferably any one of the following structures, but is not limited thereto:

[0039] ;

[0040] ;

[0041] ;

[0042] ;

[0043] ;

[0044] ;

[0045] ;

[0046] ;

[0047] ;

[0048] wherein D represents deuterium.

[0049] The green phosphorescent dopant material of the present application can be prepared by a synthetic method known to those skilled in the art. Alternatively, the following reaction scheme is preferably used for the preparation.

[0050]

[0051] In the above formula, R 1-R8, n1-n3, m are defined as in the above chemical formula I, X represents or The asterisk represents the connection site of the group.

[0052] In comparison with the complex raw materials not disclosed, the classical Suzuki coupling reaction, the Friedel-Crafts reaction, the Ullmann-type amination reaction, the displacement reaction and the application to the present application will be adopted.

[0053] The specific preparation method is as follows:

[0054] The step 1 specifically includes the following process:

[0055] The raw material A (1.0 eq), the raw material B (1.0 eq), Na2S2O3 (0.05-0.1 eq) and DMF (N, N-dimethylformamide) are added into a three-necked flask, replaced by N2, and reacted at 70-90°C for 1-12h. After the reaction is determined to be completed by thin layer chromatography, ethyl acetate and water are added for extraction and separation to obtain an organic layer which is concentrated, and the mixture solution of cyclohexane / ethyl acetate (V / V=12:1-8:1) is used for column chromatography to purify to obtain the intermediate 1.

[0056] The step 2 specifically includes the following process:

[0057] The intermediate 1 (1.0 eq), the raw material C (2.0-4.0 eq), Cu (0.5 eq), CuI (0.5 eq), 1,10-phenanthroline (1.0 eq), cesium carbonate (2.0-4.0 eq) and anhydrous xylene are added into a three-necked flask, replaced by nitrogen, and reacted at 150-180°C for 8-40h in an oil bath, and then cooled to room temperature. After the reaction is directly filtered by using ethyl acetate as a washing agent to remove inorganic salts, the mixture solution of cyclohexane / ethyl acetate (V / V=12:1-8:1) is used for column chromatography to purify to obtain the intermediate 2.

[0058] The step 3 specifically includes the following process:

[0059] The raw material D (1.0-1.2 eq), the raw material E (1.0 eq), potassium carbonate (2.0-4.0 eq) and the mixed solution of toluene, ethanol and water (V:V:V:=3:1:1) are added into a three-necked flask, replaced by nitrogen, and then tetrakis(triphenylphosphine)palladium (0.01-0.03 eq) is added, and the temperature is increased to 70-95°C for reaction for 2-12h. After the reaction is detected by thin layer chromatography, the temperature is slightly reduced, water and dichloromethane are added for extraction and separation, and the organic phase is reserved for concentration. The mixture solution of dichloromethane and petroleum ether (V:V=1:3-1:12) is used for column chromatography to purify to obtain the intermediate 3.

[0060] The step 4 specifically includes the following process:

[0061] The intermediate 3 (1.0 eq), the raw material F (1.0-2.0 eq), potassium acetate (2.0-4.0 eq) and 1,4-dioxane are added into a three-necked flask, and then the flask is purged with nitrogen. Then, tris(dibenzylideneacetone)dipalladium (0.01-0.03 eq) and X-Phos (0.1-0.2 eq) are added into the flask, and the flask is heated to 110-120°C and stirred for 2-20 hours. After the reaction is completed, water and dichloromethane are added into the flask to separate the organic phase. The organic phase is concentrated, and then a mixture of dichloromethane and petroleum ether (V:V=1:3-1:8) is used to purify the intermediate 4 by column chromatography.

[0062] Step 5 specifically includes the following process:

[0063] The intermediate 4 (1.0-1.3 eq), the intermediate 2 (1.0 eq) and a mixture of toluene, ethanol and water (V:V:V=3:1:1) are added into a three-necked flask, and then the flask is purged with nitrogen. Then, tetrakis(triphenylphosphine)palladium (0.01-0.03 eq) and potassium carbonate (2.0-4.0 eq) are added into the flask, and the flask is heated to 70-95°C and stirred for 2-10 hours. After the reaction is completed, the temperature is slightly reduced, and water and dichloromethane are added into the flask to separate the organic phase. The organic phase is concentrated, and then a mixture of dichloromethane and petroleum ether (V:V=1:3-1:10) is used to purify the intermediate 5 by column chromatography.

[0064] Step 6 specifically includes the following process:

[0065] The intermediate 5 (1.0 eq), K2PtCl4 (1.0-1.3 eq), acetic acid and H2O are added into a reaction flask, and the mixture is refluxed for 10-36 hours. The refluxed mixture obtained is cooled to room temperature, and then the precipitate is filtered. The precipitate is dissolved in dichloromethane and washed with water, and then the organic phase is concentrated. A mixture of dichloromethane and petroleum ether (V:V=1:3-1:12) is used to purify the chemical formula I by column chromatography.

[0066] Another object of the present application is to provide an organic electroluminescent device, which comprises 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 comprises a light-emitting layer, and the light-emitting layer comprises the green phosphorescent dopant material as described above.

[0067] Preferably, the light-emitting layer comprises a host material and a dopant material, and the dopant material is the green phosphorescent dopant material as described above.

[0068] Preferably, the organic layer further comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, an electron transport layer, an electron injection layer, or a hole blocking layer.

[0069] The organic layer of the organic light emitting device of the present application can be formed as a single layer structure, but can also be formed as a multi-layer structure in which the organic layer contains two or more organic material layers. For example, the organic light emitting device of the present application can have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, etc. as the organic layer. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic material layers or a larger number of organic layers.

[0070] Except for the green phosphorescent dopant material of Formula I contained in the light emitting layer of the present application, there is no particular limitation on the materials for other layers in the OLED device.

[0071] The device described in the present application can be used in organic light emitting apparatuses, including but not limited to flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, laser printers, telephones, cell phones, photo albums, personal digital assistants (PDAs), wearable devices, notebook computers, digital cameras, video cameras, viewfinders, micro-displays, three-dimensional displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays tiled together, theater or venue screens, light therapy devices, and signage.

[0072] Compared with the prior art, the present application has the following beneficial effects:

[0073] The compound of the present application is based on the ONCN tetradentate ligand containing platinum as the mother nucleus, and further connected with a trimethylsilane group. The device using the compound has high luminous efficiency, long service life, and at the same time maintains a low driving voltage. The ONCN tetradentate ligand structure containing platinum has strong rigidity. Such strong coordination bond not only inhibits ligand dissociation, but also effectively improves the stability of the overall structure, thereby improving the service life of the device. There are more modification sites, which further connect other structures, so that the phosphorescence quantum yield of the green light device is improved, and the electroluminescent performance of the compound is effectively improved. The sigma electron-donating property of the further introduced silane group can improve the electron density of the Pt metal center and enhance the MLCT transition. The huge steric hindrance hinders the close approach between the core planes of the Pt complex, effectively reduces the intermolecular π-π stacking effect, significantly reduces the concentration quenching effect, allows the use of a higher doping concentration (usually can be increased to 10-20wt% or even higher) without losing efficiency or color purity, and is more helpful to improve the carrier capture efficiency and improve the device efficiency. Moreover, the large steric hindance silane group can also inhibit the twisting vibration of the complex plane structure to a certain extent, reduce the non-radiative deactivation channel, inhibit the non-radiative d-d transition, and prevent efficiency loss. At the same time, the type and number of substituents connected to the left N of the benzimidazole are adjusted to control the material performance. The effect of connecting large steric hindance alkyl (such as tert-butyl) to the para position of the benzene ring connected to the left N of the benzimidazole and connecting aryl (such as phenyl) to the ortho position is the best. BRIEF DESCRIPTION OF DRAWINGS

[0074] Figure 1 The nuclear magnetic resonance hydrogen spectrum of compound 1 provided for example 1 of the present application. DETAILED DESCRIPTION

[0075] The technical solutions of the present application will be further described through specific embodiments. Those skilled in the art should understand that the embodiments are only to help understand the present application, and should not be regarded as specific limitations on the present application.

[0076] In addition, it should be noted that the numerical values given in the following examples are as accurate as possible, but those skilled in the art understand that due to unavoidable measurement errors and experimental operation problems, each number should be understood as an approximate number, rather than an absolutely accurate number.

[0077] Example 1

[0078]

[0079] Step 1 specifically includes the following process:

[0080] In a reaction flask, add raw material A-1 (1.0 eq, CAS No.: 1575-36-6), raw material B-1 (1.0 eq, CAS No.: 37942-07-7), Na2S2O3 (0.1 eq) and DMF (N,N-dimethylformamide), replace N2, and react at 80°C for 4h. After determining the end of the reaction by thin layer chromatography, extract the solution with ethyl acetate and water to obtain an organic layer, concentrate, and purify by column chromatography using a mixed solution of cyclohexane / ethyl acetate (V / V=8:1) to obtain intermediate 1-1 (yield: 29.7%).

[0081] Step 2 specifically includes the following process:

[0082] In a reaction flask, add intermediate 1-1 (1.0 eq), raw material C-1 (3.0 eq, CAS No.: 2490476-18-9), Cu (0.5 eq), CuI (0.5 eq), 1,10-phenanthroline (1.0 eq), cesium carbonate (3.0 eq), and anhydrous xylene, replace N2, and react at an oil bath temperature of 160°C for 14h, then cool to room temperature. After direct suction filtration of the reaction with ethyl acetate as the eluent to remove inorganic salts, purify by column chromatography using a mixed solution of cyclohexane / ethyl acetate (V / V=7:1) to obtain intermediate 2-1 (yield: 58.4%).

[0083] Step 3 specifically includes the following process:

[0084] In a reaction flask, add raw material D-1 (1.0 eq, CAS No.: 2648406-99-7), raw material E-1 (1.0 eq, CAS No.: 1257879-78-9), potassium carbonate (2.0 eq), and a mixed solution of toluene, ethanol, and water (V:V:V:=3:1:1), replace N2, then add tetrakis(triphenylphosphine)palladium (0.01 eq), and react at 95°C for 3h. After detecting the reaction by thin layer chromatography and confirming the end of the reaction, slightly reduce the temperature, extract the solution with water and dichloromethane, retain the organic phase, concentrate, purify by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:5) to obtain intermediate 3-1 (yield: 78.2%).

[0085] Step 4 specifically includes the following process:

[0086] In a reaction flask, intermediate 3-1 (1.0 eq), raw material F-1 (1.5 eq, CAS No.: 73183-34-3), potassium acetate (3.0 eq) and 1,4-dioxane were added, and after nitrogen was passed, tris(dibenzylideneacetone)dipalladium (0.02 eq) and X-Phos (0.1 eq) were added, and the reaction was stirred at 120°C for 17 h. After the reaction was determined to be completed by thin layer chromatography, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V = 1:4) was used to purify by column chromatography to obtain intermediate 4-1 (yield: 82.1%).

[0087] Step 5 specifically includes the following process:

[0088] In a reaction flask, intermediate 4-1 (1.0 eq), intermediate 2-1 (1.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V = 3:1:1) were added, and after nitrogen was passed, tetrakis(triphenylphosphine)palladium (0.03 eq) and potassium carbonate (3.0 eq) were added, and the reaction was stirred at 95°C for 9 h. After the reaction was determined to be completed by thin layer chromatography, the temperature was slightly lowered, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V = 1:5) was used to purify by column chromatography to obtain intermediate 5-1 (yield: 81.0%).

[0089] Step 6 specifically includes the following process:

[0090] In a reaction flask, intermediate 5-1 (1.0 eq), K2PtCl4 (1.2 eq), acetic acid and H2O were added and refluxed for 21 h. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered, dissolved in dichloromethane and washed with water, and then the organic phase was retained and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) was used to purify by column chromatography to obtain compound 1 (yield: 57.4%).

[0091] The obtained compound 1 was detected and analyzed, and the results were as follows:

[0092] HPLC purity: >99.6%.

[0093] Mass spectrometry test: mass spectrometer of Waters XEVO TQD type, using ESI source.

[0094] Test value MS (ESI, m / Z): [M+H] + = 1025.28

[0095] Elemental analysis:

[0096] Calculated: C, 66.77; H, 5.80; N, 4.10; O, 1.56; Pt, 19.03; Si, 2.74;

[0097] Test: C, 66.39; H, 5.90; N, 4.21; O, 1.66; Pt, 19.15; Si, 2.83.

[0098] The nuclear magnetic resonance hydrogen spectrum of compound 1 is shown in Figure 1 .

[0099] Example 2

[0100]

[0101] The synthesis process of intermediate 2-2 in this example is the same as that of intermediate 2-1 in Example 1.

[0102] The raw material E is not prior art and needs to be synthesized in advance (corresponding to step 1-2), and the corresponding intermediate B is obtained.

[0103] Step 1 specifically includes the following process:

[0104] In the reaction bottle, raw material a (1.0 eq, CAS number: 73583-37-6), raw material b (1.0 eq, CAS number: 1398503-82-6), potassium carbonate (2.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V:=3:1:1) were added, and then tetrakis(triphenylphosphine)palladium (0.01 eq) was added after nitrogen was passed. The temperature was raised to 95°C and reacted for 3h; after the reaction was confirmed to be completed by thin layer chromatography, the temperature was slightly lowered, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, and then a mixed solution of dichloromethane and petroleum ether (V:V=1:5) was used to purify by column chromatography to obtain intermediate A (yield: 78.8%).

[0105] Step 2 specifically includes the following process:

[0106] In the reaction bottle, intermediate A (1.0 eq), raw material c (1.5 eq, CAS number: 73183-34-3), potassium acetate (3.0 eq) and 1,4-dioxane were added, and then tris(dibenzylideneacetone)dipalladium (0.02 eq) and X-Phos (2-bis(cyclohexylphosphino)-2',4',6'-triisopropylbiphenyl, 0.1 eq) were added after nitrogen was passed. The temperature was raised to 120°C and stirred for 16h; after the reaction was confirmed to be completed by thin layer chromatography, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, and then a mixed solution of dichloromethane and petroleum ether (V:V=1:5) was used to purify by column chromatography to obtain intermediate B (yield: 81.7%).

[0107] Step 3 specifically includes the following process:

[0108] In a reaction bottle, raw material D-2 (1.0 eq, CAS No.: 2648406-99-7), intermediate B (1.0 eq, CAS No.: 1257879-78-9), potassium carbonate (2.0 eq), and a mixed solution of toluene, ethanol, and water (V:V:V = 3:1:1) were added, nitrogen was passed, and then tetrakis(triphenylphosphine)palladium (0.01 eq) was added, and the temperature was raised to 95°C for reaction for 4h; after the reaction was confirmed to be completed by thin layer chromatography, the temperature was slightly lowered, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, a mixed solution of dichloromethane and petroleum ether (V:V = 1:5) was used to purify by column chromatography to obtain intermediate 3-2 (yield: 77.9%).

[0109] Step 4 specifically includes the following process:

[0110] In a reaction bottle, intermediate 3-2 (1.0 eq), raw material F-2 (1.5 eq, CAS No.: 73183-34-3), potassium acetate (3.0 eq), and 1,4-dioxane were added, nitrogen was passed, and then tris(dibenzylideneacetone)dipalladium (0.02 eq) and X-Phos (0.1 eq) were added, and the temperature was raised to 120°C for stirring reaction for 18h; after the reaction was confirmed to be completed by thin layer chromatography, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) was used to purify by column chromatography to obtain intermediate 4-2 (yield: 80.6%).

[0111] Step 5 specifically includes the following process:

[0112] In a reaction bottle, intermediate 4-2 (1.0 eq), intermediate 2-2 (1.0 eq), and a mixed solution of toluene, ethanol, and water (V:V:V = 3:1:1) were added, nitrogen was passed, and then tetrakis(triphenylphosphine)palladium (0.03 eq) and potassium carbonate (3.0 eq) were added, and the temperature was raised to 95°C for reaction for 10h; after the reaction was confirmed to be completed by thin layer chromatography, the temperature was slightly lowered, water and dichloromethane were added to separate the liquid, the organic phase was retained and concentrated, a mixed solution of dichloromethane and petroleum ether (V:V = 1:5) was used to purify by column chromatography to obtain intermediate 5-2 (yield: 81.4%).

[0113] Step 6 specifically includes the following process:

[0114] In a reaction bottle, intermediate 5-2 (1.0 eq), K2PtCl4 (1.2 eq), acetic acid and H2O were added and refluxed for 23 hours. The refluxed mixture thus obtained was cooled to room temperature, filtered to obtain a precipitate, the precipitate was dissolved in dichloromethane and washed by water, then the organic phase was reserved and concentrated, purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:6) to obtain compound 2 (yield: 57.1%).

[0115] The obtained compound 2 was detected and analyzed, and the results were as follows:

[0116] HPLC purity: >99.4%.

[0117] Mass spectrometry test: mass spectrometer of Waters XEVO TQD type, using ESI source.

[0118] Test value MS (ESI, m / Z): [M+H] + =1042.19

[0119] Elemental analysis:

[0120] Calculated value: C, 66.83; H, 6.19; N, 4.03; O, 1.53; Pt, 18.72; Si, 2.69;

[0121] Test value: C, 66.43; H, 6.30; N, 4.13; O, 1.65; Pt, 18.83; Si, 2.79.

[0122] In addition, it should be noted that other compounds of the present application can be obtained by referring to the synthesis method of the above-mentioned examples, so they will not be listed one by one here.

[0123] The organic electroluminescent composition and the organic electroluminescent device provided by the present application are specifically described below in combination with specific examples.

[0124] Device Example 1: Preparation of a green organic electroluminescent device

[0125] The structure of the prepared OLED device is: ITO anode / HIL / HTL / Prime / EML / HBL / ETL / EIL / cathode / CPL.

[0126] a. ITO anode: ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 1500 angstroms was cleaned in distilled water for 3 times, ultrasonic washing for 40 min, and then cleaned in distilled water for 3 times, ultrasonic washing for 20 min. After washing, the substrate was dried, and then transferred to a plasma cleaning machine for washing for 5 min. Then, the substrate was sent to an evaporation machine, and other functional layers were evaporated on the substrate as an anode.

[0127] b. HIL (hole injection layer): HT and P-dopant were vacuum evaporated at a rate of 1 angstrom / s, and the chemical formula of the HT and P-dopant is shown below. The evaporation rate ratio of the HT and P-dopant was 97:3, and the thickness was 10 nm.

[0128] c. HTL (hole transport layer): HT was vacuum evaporated on the hole injection layer at a rate of 1.5 angstrom / s, and the thickness was 130 nm as a hole transport layer.

[0129] d. Prime (light-emitting auxiliary layer): Prime was vacuum evaporated on the hole transport layer at a rate of 0.5 angstrom / s, and the thickness was 100 nm as a light-emitting auxiliary layer.

[0130] e. EML (light-emitting layer): Then, a double-host material (Host-1 and Host-2) and a doping material (compound 1 provided in the above example) were vacuum evaporated on the light-emitting auxiliary layer at a rate of 1 angstrom / s, and the thickness was 30 nm as a light-emitting layer. The ratio of Host-1 and Host-2 was 50:50, and the evaporation rate ratio of the double-host material and the doping material was 90:10.

[0131] f. HBL (hole blocking layer): A hole blocking layer HB was vacuum evaporated at a rate of 0.5 angstrom / s, and the thickness was 5 nm.

[0132] g. ETL (electron transport layer): ET and Liq were vacuum evaporated at a rate of 1 angstrom / s, and the thickness was 30 nm as an electron transport layer. The chemical formula of the ET is shown below. The evaporation rate ratio of the ET and Liq was 50:50.

[0133] h. EIL (electron injection layer): Yb film was evaporated at a rate of 0.5 angstrom / s, and the thickness was 1 nm to form an electron injection layer.

[0134] i. Cathode: Magnesium and silver were evaporated at a rate of 1 angstrom / s, and the thickness was 13 nm. The evaporation rate ratio of magnesium and silver was 1:9 to obtain an OLED device.

[0135] j. CPL (light out-coupling layer): CPL was vacuum deposited on the cathode as a light out-coupling layer with a thickness of 65 nm at a deposition rate of 1 A / s.

[0136] k. Subsequently, the substrate on which the deposition was completed was encapsulated. First, the cleaned cover plate was coated with UV glue using a coating device, and then the coated cover plate was moved to a pressing section, the substrate on which the deposition was completed was placed on the end of the cover plate, and finally the substrate and the cover plate were laminated under the action of a laminating device, and the UV glue was simultaneously cured by light.

[0137] The structures of HT, P-dopant, Host-1, Host-2, Prime, HB, ET, and CPL used in the above device embodiment 1 are shown below:

[0138] .

[0139] Referring to the method provided in the above device embodiment 1, the corresponding compounds in Table 1 were respectively selected to replace compound 1 to perform the deposition of the doped material layer, and the corresponding organic electroluminescent devices were prepared and were respectively recorded as device embodiments 2-102.

[0140] Device comparative examples 1-14:

[0141] This comparative example provides an organic electroluminescent device, and the only difference between the preparation method of the organic electroluminescent device and device embodiment 1 is that the organic electroluminescent device is deposited by using existing comparative compounds a-n to replace the doped material (compound 1) in the above device embodiment 1. The chemical structural formulas of the comparative compounds a-n are as follows:

[0142] .

[0143] Under the current density test condition of 20 mA / cm 2 The driving voltage, luminous efficiency, and lifetime of the organic electroluminescent devices obtained from the above device embodiments 1-102 and device comparative examples 1-14 were characterized, and the test results are shown in Table 1 below.

[0144] Table 1

[0145]

[0146]

[0147]

[0148] As can be seen from Table 1, the metal compound in the present application has excellent phosphorescent light emitting properties, and the organic electroluminescent device prepared therefrom has more excellent driving voltage, luminous efficiency and lifespan, and the performance is obviously improved compared with the organic electroluminescent device prepared from the comparative compound.

[0149] Generally, the device lifespan can be improved by 10%, and in the art, it can be considered that the compound has achieved significant performance improvement, the efficiency is improved by more than 5%, and it can be considered that the efficiency has been significantly improved.

[0150] At a current density of 20 mA / cm 2 Hereinafter, the efficiency of the compound of the present application is 172.5-178.5 cd / A, the luminous efficiency of the comparative compound is 157.5-162.6 cd / A, the efficiency is improved by 6.09%-13.33%, the lifespan of the compound of the present application is 225-263 h, and the lifespan of the comparative compound is 162-185 h, and the lifespan is improved by at least 21.62%. It can be seen that the compound of the present application has made significant progress in luminous efficiency and lifespan compared with the prior art.

[0151]

[0152] The comparative compound a and the compound 1 are parallel comparative examples, the difference between them is that in the comparative compound a, a tert-butyl group is connected to the benzene ring at the upper right corner of the right parent nucleus as a substituent, while in the compound 1 of the present application, a trimethylsilyl group (TMS) is connected to the benzene ring at the corresponding position as a substituent. The Pt complex parent nucleus has a planar tetragonal structure, which is prone to intermolecular π-π stacking interaction leading to concentration quenching, and the electronegativity of silicon atom is lower than that of carbon atom, which makes the methyl group on the silicon atom more inclined to push the electron density to the silicon atom through hyperconjugation (σ-hyperconjugation). Since the bonding orbital energy level of silicon and the directly connected atom (aromatic ring carbon) is high, these electrons are more likely to be donated to the metal center or the conjugated system. In addition, the Si-C bond is longer than the C-C bond, which makes the three methyl groups more separated in space. The huge steric hindrance of TMS prevents the close approach of the Pt complex core plane, effectively reducing the intermolecular π-π stacking interaction. Significantly reduce the concentration quenching effect, allow the use of higher doping concentration without loss of efficiency or color purity. More conducive to improve the carrier capture efficiency, improve the device efficiency. Moreover, the large steric hindrance TMS group can also inhibit the twisting vibration of the complex planar structure to some extent, reduce the non-radiative deactivation channel, inhibit the non-radiative d-d transition, and prevent efficiency loss.

[0153] In addition, compared with the comparative compound a having a tert-butyl group at the substitution site, in compound 1 having a trimethylsilyl (TMS) group, the short wavelength shift (blue shift) suitable for high color purity, the high glass transition temperature (Tg) and high melting temperature (Tm) characteristics caused by the improvement of thermal stability, and the effective regulation of π-π stacking interaction were confirmed, and the sublimation purification temperature was lower under the same conditions (as shown in Table 2 below). The improved thermal characteristics and lower deposition temperature can fully explain that the deposition material not only has excellent processability, but also can realize the long service life of the device.

[0154] Table 2

[0155]

[0156] (1) The related test instruments are as follows:

[0157] Ø 80 sublimation instrument: Model CM:ON-80.

[0158] Differential scanning calorimeter: Model DSC3500.

[0159] (2) The PL test conditions are as follows:

[0160] Emission start wavelength: 350 nm.

[0161] Emission end wavelength: 650 nm.

[0162] Excitation wavelength: 375 nm.

[0163] Sample concentration: 0.5 mg / mL diluted 100 times.

[0164] Solvent: Tetrahydrofuran.

[0165] The applicant declares that the green phosphor dopant material, the preparation method thereof, the organic electroluminescent device and the organic electroluminescent apparatus of the present application are illustrated by the above examples, but the present application is not limited to the above examples, that is, it does not mean that the present application must rely on the above examples to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of the selected materials of the present application, addition of auxiliary ingredients, selection of specific methods, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. A green phosphorescent dopant material, characterized in that, The general structure of the green phosphorescent dopant material is shown as formula I: ； wherein, the ring H is phenyl; Ar is selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl; R1, R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl; R3 is independently selected from hydrogen, deuterium, trimethylsilyl, trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; n1 is an integer selected from 0, 1, 2 or 3; n2 is an integer selected from 0, 1, 2, 3 or 4; n3 is an integer selected from 0, 1, 2, 3 or 4; R4-R6 are independently selected from deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6 aryl; R7, R8 are independently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6 aryl; m is an integer selected from 0, 1 or 2; in formula I, two of the four bonds connected to the central metal Pt are coordination bonds, and the other two are covalent bonds, the bonds between the metal Pt and the two N are coordination bonds, the bond between the Pt and the ring H is a covalent bond, and the bond between the Pt and the O is a covalent bond; the hydrogen involved in formula I is not deuterated, partially deuterated or fully deuterated; the "substituted" group in the substituted or unsubstituted group is selected from one or at least two groups of the following substituents: deuterium, halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, sec-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridyl group, dibenzofuranyl group, dibenzothiophenyl group.

2. The green phosphorescent dopant material according to claim 1, wherein Ar is selected from substituted or unsubstituted C6-C24 aryl; R1, R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl; R3 is independently selected from hydrogen, deuterium, trimethylsilyl, trifluoromethyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; R4-R6 are independently selected from deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6 aryl; R7, R8 are independently selected from hydrogen, deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6 aryl.

3. A green phosphorescent dopant material characterized in that, The general structure of the green phosphorescent dopant material is shown as formula I-A: ； wherein the ring H is phenyl; Ar1, Ar2are independently selected from the group consisting of hydrogen, deuterium, halogen radical, trimethylsilyl radical, substituted or unsubstituted C1-C6 alkyl radical, substituted or unsubstituted C3-C6 cycloalkyl radical, substituted or unsubstituted C6-C18 aryl radical; n9, n 10 an integer independently selected from 0, 1, 2, 3, 4, or 5; R1, R2are independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted methyl radical, substituted or unsubstituted ethyl radical, substituted or unsubstituted propyl radical, substituted or unsubstituted butyl radical, substituted or unsubstituted pentyl radical, substituted or unsubstituted hexyl radical, substituted or unsubstituted cyclopropyl radical, substituted or unsubstituted cyclobutyl radical, substituted or unsubstituted cyclopentyl radical, substituted or unsubstituted cyclohexyl radical; R3is independently selected from the group consisting of hydrogen, deuterium, trimethylsilyl radical, trifluoromethyl radical, substituted or unsubstituted methyl radical, substituted or unsubstituted ethyl radical, substituted or unsubstituted propyl radical, substituted or unsubstituted butyl radical, substituted or unsubstituted pentyl radical, substituted or unsubstituted hexyl radical, substituted or unsubstituted cyclopropyl radical, substituted or unsubstituted cyclobutyl radical, substituted or unsubstituted cyclopentyl radical, substituted or unsubstituted cyclohexyl radical, substituted or unsubstituted phenyl radical, substituted or unsubstituted biphenyl radical, substituted or unsubstituted naphthyl radical, substituted or unsubstituted phenanthryl radical, substituted or unsubstituted pyridyl radical, substituted or unsubstituted dibenzofuranyl radical, substituted or unsubstituted dibenzothiophenyl radical; n1is an integer selected from 0, 1, 2 or 3; n2is an integer selected from 0, 1, 2, 3 or 4; n3is an integer selected from 0, 1, 2, 3 or 4; R4-R6are independently selected from the group consisting of deuterium, substituted or unsubstituted methyl radical, substituted or unsubstituted ethyl radical, substituted or unsubstituted propyl radical, substituted or unsubstituted butyl radical, substituted or unsubstituted pentyl radical, substituted or unsubstituted hexyl radical, substituted or unsubstituted phenyl radical; R7, R8are independently selected from the group consisting of deuterium, substituted or unsubstituted methyl radical, substituted or unsubstituted ethyl radical, substituted or unsubstituted propyl radical, substituted or unsubstituted butyl radical, substituted or unsubstituted pentyl radical, substituted or unsubstituted hexyl radical, substituted or unsubstituted cyclopropyl radical, substituted or unsubstituted cyclobutyl radical, substituted or unsubstituted cyclopentyl radical, substituted or unsubstituted cyclohexyl radical, substituted or unsubstituted phenyl radical; m is an integer selected from 0, 1 or 2; In chemical formula I-A, two of the four bonds connecting the central metal Pt are coordination bonds, and the other two are covalent bonds. The bonds between the metal Pt and the two N are coordination bonds, the bond between the Pt and the ring H is a covalent bond, and the bond between the Pt and the O is a covalent bond; The hydrogen involved in chemical formula I-A is not deuterated, partially deuterated or fully deuterated; The "substituted" group in the substituted or unsubstituted is selected from one or at least two groups of substituents connected to the following groups: deuterium, halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridyl group, dibenzofuranyl group, dibenzothiophenyl group.

4. A green phosphorescent dopant material characterized in that, The structure general formula of the green phosphorescent dopant material is: ； Ar1, Ar2 are independently selected from deuterium, trimethylsilyl group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted pentyl group, substituted or unsubstituted hexyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group; n9, n 10 an integer independently selected from 0, 1, 2, 3, 4, or 5; R1, R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted pentyl group, substituted or unsubstituted hexyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group; R3 is independently selected from hydrogen, deuterium, trimethylsilyl group, trifluoromethyl group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted pentyl group, substituted or unsubstituted hexyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group; n1 is selected from an integer of 0, 1, 2 or 3; n2 is selected from an integer of 0, 1, 2, 3 or 4; n3 is selected from an integer of 0, 1, 2, 3 or 4; R4-R6 are independently selected from deuterium, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted pentyl group, substituted or unsubstituted hexyl group, substituted or unsubstituted phenyl group; R7, R8are independently selected from the group consisting of deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl; m is an integer selected from 0, 1 or 2; in chemical formula I-A-1 or I-A-2, two of the four bonds connecting the central metal Pt are coordination bonds, and the other two are covalent bonds, the metal Pt is coordinated with two N, the bond between Pt and ring H is a covalent bond, and the bond between Pt and O is a covalent bond; the hydrogen involved in chemical formula I-A-1 or I-A-2 is unsubstituted, partially deuterated or fully deuterated; the "substituted" group in the substituted or unsubstituted group is selected from one or at least two groups connected to the substituent: deuterium, halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridyl group, dibenzofuranyl group, dibenzothiophenyl group.

5. A green phosphorescent dopant material characterized in that, The green phosphorescent dopant material is any one of the following compounds: ； ； ； ； ； ； ； ； ； wherein D represents deuterium.

6. An organic electroluminescent device, characterized by The organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising a light-emitting layer, the light-emitting layer comprising the green phosphorescent dopant material according to any one of claims 1-5.

7. The organic electroluminescent device according to claim 6, characterized in that The light-emitting layer comprises a host material and a dopant material, and the dopant material is the green phosphorescent dopant material according to any one of claims 1-5.

8. The organic electroluminescent device according to claim 6, characterized in that The organic layer further comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, or a hole blocking layer.

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