Platinum complex derivative containing intramolecular high-entropy charge transfer and application thereof
By introducing high-entropy charge transfer in molecules into organic narrowband luminescent materials, the problems of long exciton lifetime and unbalanced charge carrier transfer in existing materials are solved, and the effects of high efficiency, narrow half-maximum width and short exciton lifetime are achieved. It is suitable for high-performance organic electroluminescent devices.
Patent Information
- Application Number
- CN202510023521.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-01-07
- Publication Date
- 2025-04-18
AI Technical Summary
Existing organic narrowband luminescent materials have long exciton lifetimes and unbalanced charge carrier transmission, resulting in efficiency roll-off and cannot meet the needs of high luminescence efficiency, narrow half-maximum width and short exciton lifetime.
Using platinum complex derivatives containing high entropy charge transfer in the molecule, a luminescent material with high color purity, high efficiency, and short exciton lifetime is constructed by introducing multiple resonance effect-induced luminescent units and units based on platinum complexes.
It realizes the characteristics of high efficiency, narrow luminescence spectrum and short exciton lifetime, reduces efficiency roll-off, and is suitable for wide color gamut and high efficiency organic electroluminescent devices.
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Figure CN119841870A_ABST
Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a platinum complex derivative containing intramolecular high entropy charge transfer and an application thereof. Background Art
[0002] Organic electroluminescent devices (OLEDs) have shown unique potential and advantages in the field of flat panel displays and solid-state lighting due to their advantages such as low power consumption, high contrast, wide viewing angle, ultra-high definition, and flexibility. As the core component of OLEDs, the luminescent layer material determines the key indicators of the device through its luminescent performance. With the increasing demand for the clarity of display products, display technology needs to be met as much as possible. The current color gamut standard of ultra-high-definition television signals has higher requirements for the color purity of luminescent materials. In recent years, the development of luminescent materials with narrow half-width characteristics has become a hot spot in the development of OLED luminescent materials. Compared with traditional fluorescent materials, phosphorescent materials, and electron donor-acceptor (DA) thermally activated delayed fluorescent materials (TADF), multi-resonance thermally activated delayed fluorescent materials (MR-TADF) have a rigid skeleton with short-range charge transfer and weakened bonding / anti-bonding characteristics, which is conducive to reducing the structural relaxation of the excited state, the vibration coupling between the singlet ground state and the singlet excited state, and the reorganization energy, thereby achieving a small half-width and Stokes shift. At present, organic narrow-band luminescent materials mainly include two types: boron-containing and boron-free (containing carbonyl or indole and carbazole derivatives). However, the above materials usually show a long exciton lifetime and unbalanced charge carrier transport, which leads to a significant efficiency roll-off in the device. Therefore, it is urgent to develop an organic light-emitting material system with high luminous efficiency, narrow half-peak width, and short exciton lifetime. In order to maintain a narrow emission spectrum, the molecule needs to have a rigid multi-resonance structure. In order to improve the luminous efficiency, more charge transfer pathways are required, tending to high entropy, so as to capture more excitons to participate in the radiative recombination process. Summary of the invention
[0003] In order to solve the above problems, the present invention provides a platinum complex derivative comprising intramolecular high entropy charge transfer and application thereof.
[0004] To achieve the above object, the present invention adopts the following technical solutions:
[0005] A platinum complex derivative comprising intramolecular high entropy charge transfer, the platinum complex derivative comprising intramolecular high entropy charge transfer comprises a light-emitting unit induced by a multiple resonance effect and a unit based on a platinum complex, and the platinum complex derivative comprising intramolecular high entropy charge transfer is shown in the general formula (1):
[0006]
[0007] Among them, the A unit is selected from a boron atom or a nitrogen atom; R1, R2 and R3 are the same or different; a, b and c are independently selected from 0 or 1, and a+b+c is greater than or equal to 2; I, II and III are the same or different, and each is independently selected from one or more five-membered rings or six-membered rings or heterocycles, or a condensed system composed of one or more five-membered rings or six-membered rings or heterocycles; IV is a unit based on a platinum complex.
[0008] Preferably, IV is selected from the group represented by formula (5) or formula (6);
[0009]
[0010]
[0011] in, represents the connection point with unit I in formula (1); substituents L1, L2, L3 and L4 are the same or different and are selected from hydrogen atoms, substituted or unsubstituted C 1~12 Alkyl, C 6~18 Aryl or C 5-18 A fused system consisting of a heteroaryl group, one or more five-membered rings or six-membered rings or heterocyclic rings; L5 is selected from C 1~12 Alkyl, C 6~18 Aryl or C 5-18 The heteroaryl group.
[0012] Preferably, when the A unit is a boron atom, R1, R2 and R3 are each independently selected from a carbon atom, an oxygen atom, a sulfur atom, a selenium atom, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; the light-emitting unit has the structural characteristics of formula (2):
[0013]
[0014] Wherein, L6 and L7 are the same or different and are independently selected from C 1-12 alkyl, one or more five-membered rings or six-membered rings or heterocyclic rings, a fused system consisting of one or more five-membered rings or six-membered rings or heterocyclic rings, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; D is selected from carbon atom, oxygen atom, sulfur atom, selenium atom, N-(C 6-14 Aryl), N-(C 6-14 Aryl) and the condensed system of the phenyl group where L6 is located, C 1-6 Alkyl substituted 6-membered heteroaryl, C 1-6 A condensed system of an alkyl-substituted 6-membered heteroaryl group and the phenyl group where L6 is located; E is selected from a hydrogen atom, a carbon atom, an oxygen atom, N-(C 6-14Aryl), C 1-6 Alkyl substituted 6-membered heteroaryl; --- indicates connection or non-connection.
[0015] Preferably, when the A unit is a nitrogen atom, R1 and R2 are selected from carbonyl groups, and R3 is selected from hydrogen atoms, carbon atoms, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; the light-emitting unit has the structural features of formula (3) or formula (4):
[0016]
[0017] wherein L8 and L9 are the same or different and are independently selected from C1-12 alkyl, one or more five-membered rings or six-membered rings or heterocycles, a fused system consisting of one or more five-membered rings or six-membered rings or heterocycles, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; E is selected from a carbon atom or a carbonyl group; --- indicates connection or non-connection.
[0018] Preferably, the platinum complex derivative comprising intramolecular high entropy charge transfer has a structure as shown in any of the following:
[0019]
[0020]
[0021]
[0022]
[0023] An application of a platinum complex derivative containing intramolecular high entropy charge transfer, wherein the platinum complex derivative containing intramolecular high entropy charge transfer is applied to an organic electroluminescent device; the organic electroluminescent device comprises an anode, an organic functional layer, an organic light-emitting layer and a cathode; the organic functional layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer; the platinum complex derivative containing intramolecular high entropy charge transfer is located in the organic light-emitting layer as a light-emitting material.
[0024] After adopting the above technical solution, the present invention has the following beneficial effects:
[0025] 1. The platinum complex derivatives containing intramolecular high entropy charge transfer of the present invention are used as luminescent materials, and the luminescent units induced by the multiple resonance effect are introduced into the units based on the platinum complexes. By modifying the multiple resonance units and the complex ligands, luminescent materials with high color purity, high efficiency and short exciton lifetime are constructed, and applied to organic electroluminescent devices. The luminescent materials obtained by the present invention have the characteristics of high efficiency, narrow luminescence spectrum and short exciton lifetime, which provides an effective molecular design strategy for preparing wide color gamut, high efficiency and low efficiency roll-off devices, and has broad application prospects.
[0026] 2. The present invention utilizes the high utilization rate of excitons in the complex unit to construct a long-range energy transfer channel between the intramolecular complex unit and the multiple resonance unit, suppressing the concentration quenching effect caused by the aggregation of triplet excitons, while ensuring high-efficiency, narrow emission band luminescence, achieving a short exciton lifetime and promoting rapid reverse intersystem crossing.
[0027] 3. The complex luminescent material described in the present invention has a definite molecular structure, is easy to synthesize, and can be mass-produced.
[0028] 4. The organic light-emitting material described in the present invention can be used as a light-emitting layer and applied to an electroluminescent device to achieve electroluminescent performance with high efficiency, high color purity and small efficiency roll-off. BRIEF DESCRIPTION OF THE DRAWINGS
[0029] Figure 1 This is a transient life graph of the final product obtained in Example 1 of the present invention;
[0030] Figure 2 is a schematic structural diagram of an organic electroluminescent device of the present invention;
[0031] Figure 3 The electroluminescence spectrum of the device prepared by using the final product obtained in Example 1 of the present invention;
[0032] Figure 4 This is a graph showing the external quantum efficiency of a device prepared using the final product of Example 1 of the present invention. DETAILED DESCRIPTION
[0033] In order to make the purpose, technical solution and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.
[0034] like Figures 1 to 4 shown.
[0035] Example 1: Synthesis of Compound 1-1
[0036] The synthetic route of compound A1 is as follows:
[0037]
[0038] Under nitrogen atmosphere, compound 1 (2.71 g, 8 mmol), 1-(3-bromophenyl)-1H-pyrazole (1.78 g, 8 mmol), and cesium carbonate (10.42 g, 32 mmol) were added to a 250 mL three-necked reaction bottle in sequence, and the evacuation and nitrogen filling were repeated three times. Then, ultra-dry DMF solvent (80 mL) was added, and the mixture was heated to 100 ° C and refluxed with stirring for 24 hours. After the reaction was completed and cooled to room temperature, the reaction solution was extracted with ethyl acetate and washed with deionized water. The combined organic phase was then washed with saturated brine several times, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to dryness. The crude product was further purified by column chromatography to obtain a white solid A1 (2.50 g, yield: 65%).
[0039] MS (EI): m / z 480.06 [M + ]; Combustion method element analysis: C 17 H 13 BN2O3 (%) calculated value: C, 64.88; H, 3.56; Br, 16.60; N, 11.64; O, 3.32. Found value: C, 64.90; H, 3.60; Br, 16.98; N, 11.71; O, 3.39.
[0040] The synthetic route of compound A2 is as follows:
[0041]
[0042] Under nitrogen atmosphere, bis(1,5-cyclooctadiene) dimethoxyiridium (39.8 mg, 0.06 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (32.2 mg, 0.12 mmol), and boric acid pinacol ester (1.57 g, 6.2 mmol) were added to the ultra-dry THF solution containing compound 2 (2.50 g, 6 mmol) in sequence, and the solution was evacuated and filled with nitrogen three times, and heated under reflux and stirred for 24 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane and deionized water, and the combined organic phase was dried with anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was further purified by column chromatography to obtain a yellow solid A2 (2.77 g, yield: 85%).
[0043] MS(EI): m / z 542.23[M + ]; Combustion method element analysis: C 36 H 28B2N2O2 (%) calculated value: C, 79.74; H, 5.20; B, 3.99; N, 5.17; O, 5.90 Found value: C, 79.72; H, 5.18; B, 4.01; N, 5.21; O, 5.84.
[0044] The synthetic route of compound A3 is as follows:
[0045]
[0046] Compound A1 (962.7 mg, 2 mmol), A2 (1.2 g, 2 mmol), KOAC (694 mg, 18 mmol), THF / H2O (18 mL / 4 mL) mixture were added to a 50 mL double-necked flask, and Pd(PPh3)4 (92 mg, 0.1 mmol) was finally added, and refluxed at 70 ° C for 24 h under N2 atmosphere. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product compound A3 (1.22 g, yield: 75%) as a light yellow solid.
[0047] MS(EI): m / z 816.28[M + ]; Combustion method element analysis: C 56 H 33 BN6O (%) calculated value: C, 82.35; H, 4.07; B, 1.32; N, 10.29; O, 1.96 Found value: C, 82.31; H, 4.11; B, 1.29; N, 10.21; O, 2.01.
[0048] The synthetic route of compound 1-1 is as follows:
[0049]
[0050] In a double-necked flask, add A3 compound (816.8 mg, 1 mmol), potassium chloroplatinate (456.6 mg, 1.1 mmol), tetrabutylammonium bromide (32.3 mg, 0.1 mmol), acetic acid (40 mL), replace nitrogen at least three times, and stir at room temperature for 24 hours. Then transfer the reaction flask to an oil bath and reflux at 110 ° C for three days. After the reaction is completed and returned to room temperature, slowly add deionized water (40 mL), stir for 5-10 minutes, filter the precipitate, and wash with deionized water three times. The solid product is dried by vacuum rotary evaporation and separated by silica gel column chromatography to obtain the product compound 1-1 (454.4 mg, yield: 45%) as a light yellow solid.
[0051] MS (EI): m / z 1009.23 [M + ]; Combustion method element analysis: C 56 H 31 BN6OPt (%) calculated values: C, 66.61; H, 3.09; B, 1.07; N, 8.32; O, 1.58; Pt, 19.32. Found values: C, 66.63; H, 3.11; B, 1.12; N, 8.21; O, 1.49; Pt, 19.30.
[0052] Example 2: Synthesis of Compound 1-3
[0053] The synthetic route of compound B1 is as follows:
[0054]
[0055] 2-Bromocarbazole (3.69 g, 15 mmol), 2-fluoropyridine (1.75 g, 18 mmol), and cesium carbonate (14.6 g, 45 mmol) were added to a 250 mL three-necked reaction bottle in sequence, and the reaction was repeated three times by vacuuming and filling with nitrogen. Then, ultra-dry DMF solvent (70 mL) was added, and the reaction was heated to 180 ° C and refluxed with stirring for 24 hours. After the reaction was completed and cooled to room temperature, the reaction solution was extracted with a mixture of deionized water and dichloromethane, and washed with deionized water. The combined organic phase was washed with saturated brine several times, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was further purified by column chromatography to obtain a white solid B1 (4.18 g, yield: 72%).
[0056] MS(EI): m / z 322.01[M + ]; Combustion method element analysis: C 17 H 11 Calculated value of BrN2(%): C, 63.18; H, 3.43; Br, 24.72; N, 8.67 Found: C, 63.23; H, 3.40; Br, 24.68; N, 8.61.
[0057] The synthetic route of compound B2 is as follows:
[0058]
[0059] Under nitrogen atmosphere, B1 (1.94 g, 6 mmol), 3-iodophenol (1.32 g, 6 mmol), cesium carbonate (7.82 g, 24 mmol), and ultra-dry DMF solvent (40 mL) were added to a 250 mL double-necked flask in sequence, heated to reflux at 100°C for 12 hours, and ventilated three times. After the reaction returned to room temperature, the reaction mixture was extracted (dichloromethane / deionized water), and the combined organic phase was washed with saturated brine, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to dryness. The crude product was further purified by column chromatography to obtain a white solid B2 (2.27 g, yield: 82%).
[0060] MS (EI): m / z 462.02 [M + ]; Combustion method element analysis: C 23 H 15 IN2O (%) calculated value: C, 59.76; H, 3.27; I, 27.45; N, 6.06; O, 3.46 Found value: C, 59.79; H, 3.36; I, 27.28; N, 5.91; O, 3.51.
[0061] The synthetic route of compound B3 is as follows:
[0062]
[0063] B2 (1.03 g, 2 mmol), 4-bromopyrazole (323.3 mg, 2.2 mmol), CuI (7.7 mg, 0.04 mmol), trans-1,2-cyclohexanediamine (45.7 mg, 0.4 mmol), K2CO3 (580.5 mg, 4.2 mmol) were added to a 100 mL double-necked flask in sequence, 15 mL of ultra-dry 1,4-dioxane was added, nitrogen was replaced three times, heated to 110 ° C and refluxed for 48 h, after the reaction was completed, cooled to room temperature, deionized water and dichloromethane were added to the reaction mixture for extraction, the organic phases were combined, dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain an oily product B3 (693.1 mg, yield: 72%).
[0064] MS (EI): m / z 480.06 [M + ]; Combustion method element analysis: C 26 H 17 Calculated value of BrN4O (%): C, 64.88; H, 3.56; Br, 16.6; N, 11.64; O, 3.32. Found value: C, 64.90; H, 3.49; Br, 16.5; N, 11.65; O, 3.29.
[0065] The synthetic route of compound B4 is as follows:
[0066]
[0067] Under nitrogen atmosphere, B3 (722 mg, 1.5 mmol), A2 (813.4 mg, 1.5 mmol), KOAC (1.32 g, 13.5 mmol), THF / H2O (18 mL / 4 mL) were added to a 100 mL double-necked flask, and Pd(PPh3)4 (86.6 mg, 0.075 mmol) was added at last. The mixture was replaced with nitrogen more than three times and refluxed at 70°C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product B4 (808.6 g, yield: 66%) as a white solid.
[0068] MS(EI): m / z 816.28[M + ]; Combustion method element analysis: C 56 H 33 BN6O (%) calculated value: C, 82.35; H, 4.07; B, 1.32; N, 10.29; O, 1.96. Found value: C, 82.33; H, 4.11; B, 1.35; N, 10.35; O, 2.02.
[0069] The synthetic route of compound 1-3 is as follows:
[0070]
[0071] In a double-necked flask, add B4 compound (408.4 mg, 0.5 mmol), potassium chloroplatinate (228.3 mg, 0.55 mmol), tetrabutylammonium bromide (16.1 mg, 0.05 mmol), acetic acid (30 mL), replace nitrogen at least three times, and stir at room temperature for 24 hours. Then transfer the reaction flask to an oil bath and reflux at 110 ° C for three days. After the reaction is completed and returned to room temperature, slowly add deionized water (40 mL), stir for 5-10 minutes, filter the precipitate, and wash with deionized water three times. The solid product is dried by vacuum rotary evaporation and separated by silica gel column chromatography to obtain the product compound 1-3 (217.1 mg, yield: 43%) as a light yellow solid.
[0072] MS (EI): m / z 1009.23 [M + ]; Combustion method element analysis: C 56 H 31BN6OPt (%) calculated values: C, 66.61; H, 3.09; B, 1.07; N, 8.32; O, 1.58; Pt, 19.32. Found values: C, 66.70; H, 3.14; B, 1.09; N, 8.27; O, 1.62; Pt, 19.28.
[0073] Example 3: Synthesis of Compound 1-10
[0074] The synthetic route of compound C1 is as follows:
[0075]
[0076] Under nitrogen atmosphere, compound 1 (1.69 g, 5 mmol), 1-(3-bromo-5-(tert-butyl)phenyl)-1H-imidazole (1.53 g, 5.5 mmol), and cesium carbonate (6.51 g, 20 mmol) were added to a double-necked flask in sequence, and the nitrogen was replaced at least three times, and then heated to reflux at 150°C with stirring for 24 h. The reaction mixture was extracted with ethyl acetate / deionized water, and the combined organic phase was dried over anhydrous Na2SO4, and the solid product was evaporated under reduced pressure and dried, and separated by silica gel column chromatography to obtain compound C1 (1.50 g, yield: 56%).
[0077] MS (EI): m / z 536.12 [M + ]; Combustion method element analysis: C 30 H 25 Calculated value of BrN4O (%): C, 67.04; H, 4.69; N, 10.42; Br, 14.87; O, 2.98 Found value: C, 67.10; H, 4.72; N, 10.48; Br, 14.91; O, 3.01.
[0078] The synthetic route of compound C2 is as follows:
[0079]
[0080] C1 (913.7 mg, 1.7 mmol), CB (1.53 g, 2.0 mmol), KOAC (1.50 g, 15.3 mmol) were added to a 100 mL double-necked flask, and a mixture of THF / H2O (20 mL / 4.5 mL) was added to a 100 mL double-necked flask. Finally, Pd(PPh3)4 (98.2 mg, 0.085 mmol) was added under a nitrogen atmosphere, and the nitrogen was replaced more than three times, and refluxed at 70 ° C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain a white product C2 (1.10 g, yield: 59%).
[0081] MS (EI): m / z 1096.59 [M + ]; Combustion method element analysis: C 76 H 73 BN6O (%) calculated value: C, 83.19; H, 6.71; B, 0.99; N, 7.66; O, 1.46 Found value: C, 83.21; H, 6.72; B, 0.10; N, 7.59; O, 1.41.
[0082] The synthetic route of compound C3 is as follows:
[0083]
[0084] Under nitrogen atmosphere, C2 compound (877.8 mg, 0.8 mmol), iodomethane (136.3 mg, 0.96 mmol), acetone (8 mL) were added to a double-necked flask in sequence, and the nitrogen was replaced at least three times, and then stirred at room temperature for 48 h. The solid product was evaporated and dried under reduced pressure, and the compound (743.3 mg, 0.678 mmol) obtained by silica gel column chromatography was directly used for the next step reaction, and MeOH / H2O (6 mL / 4 mL) was added, and stirred at room temperature for 30 min until the solid was completely dissolved, and then ammonium hexafluorophosphate (122.2 mg, 0.75 mmol) was added to the reaction bottle, and stirring was continued for 72 h at room temperature, and the precipitate was filtered and washed with deionized water and ethanol to obtain C3 compound (684 mg, yield: 68%).
[0085] MS (EI): m / z 1256.58 [M + ]; Combustion method element analysis: C 77 H 76BF6N6OP (%) calculated values: C, 73.56; H, 6.09; B, 0.86; F, 9.07; N, 6.68; O, 1.27; P, 2.46. Found values: C, 74.22; H, 5.98; B, 0.83; N, 6.71; O, 1.32; P, 2.51.
[0086] The synthetic route of compound 1-10 is as follows:
[0087]
[0088] C3 (628.6 mg, 0.5 mmol), (1,5-cyclooctadiene) platinum (II) dichloride (196.5 mg, 0.53 mmol), sodium acetate (123 mg, 1.5 mmol) were added to a high pressure reaction bottle containing THF (30 mL), nitrogen was replaced more than three times, and the reaction was carried out at 120 ° C for 48 h. After the reaction was completed and cooled to room temperature, it was concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product 1-10 (248 mg, yield: 38%) as a light yellow solid.
[0089] MS (EI): m / z 1304.57 [M + ]; Combustion method element analysis: C 77 H 74 BN6OPt (%) calculated values: C, 70.85; H, 5.71; B, 0.83; N, 6.44; O, 1.23; Pt, 14.94. Found values: C, 70.90; H, 5.75; B, 0.79; N, 6.39; O, 1.25; P, 15.01.
[0090] Example 4: Synthesis of Compound 2-2
[0091] The synthetic route of compound D1 is as follows:
[0092]
[0093] Compound 4 (922.5 mg, 2 mmol), KOAC (588.8 mg, 6 mmol), biboronic acid pinacol ester (1.01 g, 4 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (73.2 mg, 0.1 mmol), ultra-dry 1,4-dioxane solvent (60 mL) were added to a 250 mL double-necked reaction bottle, and nitrogen was replaced more than three times, and refluxed at 120 ° C for 48 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with deionized water and dichloromethane. The collected organic phase was dried with anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain product D1 (843.7 mg, yield: 83%) as a light yellow solid.
[0094] MS (EI): m / z 508.30 [M + ]; Combustion method element analysis: C 32 H 38 B2O4 (%) calculated value: C, 75.62; H, 7.54; B, 4.25; O, 12.59. Found value: C, 75.96; H, 7.88; B, 4.18; O, 12.63.
[0095] The synthetic route of compound D2 is as follows:
[0096]
[0097] Compound D1 (762.4 mg, 1.5 mmol), A2 (1.2 g, 1.5 mmol), KOAC (722.0 mg, 1.5 mmol), THF / H2O (13.5 mL / 3 mL) mixture were added to a 50 mL double-necked flask, and finally Pd(PPh3)4 (86.7 mg, 0.075 mmol) was added, and refluxed at 70 ° C for 24 h under N2 atmosphere. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product compound D2 (775.0 g, yield: 66%) as a light yellow solid.
[0098] MS (EI): m / z 508.30 [M + ]; Combustion method element analysis: C 52 H 43 BN4O3 (%) calculated value: C, 79.79; H, 5.54; B, 1.38; N, 7.16; O, 6.13 Found value: C, 79.86; H, 5.63; B, 1.41; N, 7.14; O, 6.10.
[0099] The synthetic route of compound 2-2 is as follows:
[0100]
[0101] In a double-necked flask, add D2 compound (782.7 mg, 1 mmol), potassium chloroplatinate (456.6 mg, 1.1 mmol), tetrabutylammonium bromide (32.3 mg, 0.1 mmol), acetic acid (45 mL), replace nitrogen at least three times, and stir at room temperature for 24 hours. Then transfer the reaction flask to an oil bath and reflux at 110 ° C for three days. After the reaction is completed and returned to room temperature, slowly add deionized water (45 mL), stir for 5-10 minutes, filter the precipitate, and wash it three times with deionized water. The solid product is dried by vacuum rotary evaporation and separated by silica gel column chromatography to obtain the product compound 2-2 (477.9 mg, yield: 49%) as a white solid.
[0102] MS (EI): m / z 975.29 [M + ]; Combustion method element analysis: C 52 H 41 BN4O3Pt(%) calculated values: C, 64.00; H, 4.24; B, 1.11; N, 5.74; O, 4.92; Pt, 19.99. Measured values: C, 63.94; H, 4.23; B, 1.16; N, 5.80; O, 4.84; Pt, 20.01.
[0103] Example 5: Synthesis of Compound 2-6
[0104] The synthetic route of compound E1 is as follows:
[0105]
[0106] 2-Bromocarbazole (3.69 g, 15 mmol), 2-fluoro-5-phenylpyridine (3.11 g, 18 mmol), and cesium carbonate (14.6 g, 45 mmol) were added to a 250 mL three-necked reaction bottle in sequence, and the reaction was vacuumed and filled with nitrogen three times. Then, ultra-dry DMF solvent (75 mL) was added, and the reaction was heated to 180 ° C and refluxed for 24 hours. After the reaction was completed and cooled to room temperature, the reaction solution was extracted with a mixture of deionized water and dichloromethane, and washed with deionized water. The combined organic phase was washed with saturated brine several times, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was further purified by column chromatography to obtain a white solid B1 (5.46 g, yield: 72%).
[0107] MS (EI): m / z 398.04 [M + ]; Combustion method element analysis: C 23 H 15Calculated value for BrN2(%): C, 69.19; H, 3.79; Br, 20.01; N, 7.02 Found: C, 69.21; H, 3.69; Br, 20.09; N, 6.99.
[0108] The synthetic route of compound E2 is as follows:
[0109]
[0110] Under nitrogen atmosphere, E1 (2.79 g, 7 mmol), 3-iodophenol (1.54 g, 7 mmol), cesium carbonate (9.12 g, 28 mmol), and ultra-dry DMF solvent (70 mL) were added to a 250 mL double-necked flask in sequence, heated to reflux at 100°C for 12 hours, and ventilated three times. After the reaction returned to room temperature, the reaction mixture was extracted (dichloromethane / deionized water), and the combined organic phase was washed with saturated brine, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to dryness. The crude product was further purified by column chromatography to obtain a white solid B2 (2.93 g, yield: 78%).
[0111] MS (EI): m / z 538.05 [M + ]; Combustion method element analysis: C 29 H 19 IN2O (%) calculated value: C, 64.70; H, 3.56; I, 23.57; N, 5.20; O, 2.97 Found value: C, 64.30; H, 3.51; I, 23.44; N, 5.12; O, 3.01.
[0112] The synthetic route of compound E3 is as follows:
[0113]
[0114] E2 (1.34 g, 2.5 mmol), 4-bromopyrazole (404.2 mg, 2.75 mmol), CuI (9.5 mg, 0.05 mmol), trans-1,2-cyclohexanediamine (57.1 mg, 0.5 mmol), K2CO3 (725.6 mg, 5.25 mmol) were added to a 100 mL double-necked flask, 20 mL of ultra-dry 1,4-dioxane was added, nitrogen was replaced three times, heated to 110 ° C and refluxed for 48 h, after the reaction was completed, cooled to room temperature, deionized water and dichloromethane were added to the reaction mixture for extraction, the organic phases were combined, dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain an oily product E3 (933.7 mg, yield: 67%).
[0115] MS (EI): m / z 538.05 [M+ ]; Combustion method element analysis: C 32 H 21 Calculated value of BrN4O (%): C, 68.95; H, 3.80; Br, 14.33; N, 10.05; O, 2.87 Found value: C, 69.01; H, 3.81; Br, 43.44; N, 9.98; O, 2.79.
[0116] The synthetic route of compound E4 is as follows:
[0117]
[0118] Under nitrogen atmosphere, E3 (1.11 g, 2 mmol), D1 (1.01 g, 2 mmol), KOAC (1.76 g, 18.0 mmol), THF / H2O (25 mL / 5.5 mL) were added to a 100 mL double-necked flask, and Pd(PPh3)4 (116 mg, 0.1 mmol) was added at last. The nitrogen was replaced more than three times and refluxed at 70°C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product compound E4 (1.18 g, yield: 69%) as a light yellow solid.
[0119] MS (EI): m / z 858.37 [M + ]; Combustion method element analysis: C 58 H 47 BN4O3 (%) calculated value: C, 81.11; H, 5.52; B, 1.26; N, 6.52; O, 5.59. Found value: C, 81.18; H, 5.50; B, 1.33; N, 6.48; O, 5.62.
[0120] The synthetic route of compound 2-6 is as follows:
[0121]
[0122] In a double-necked flask, add E4 compound (601.2 mg, 0.7 mmol), potassium chloroplatinate (319.6 mg, 0.77 mmol), tetrabutylammonium bromide (22.6 mg, 0.07 mmol), acetic acid (35 mL), replace nitrogen at least three times, and stir at room temperature for 24 hours. Then transfer the reaction flask to an oil bath and reflux at 110 ° C for three days. After the reaction is completed and returned to room temperature, slowly add deionized water (40 mL), stir for 5-10 minutes, filter the precipitate, and wash with deionized water three times. The solid product is dried by vacuum rotary evaporation and separated by silica gel column chromatography to obtain the product compound 1-3 (316.6 mg, yield: 43%) as a light yellow solid.
[0123] MS (EI): m / z 1051.32 [M + ]; Combustion method element analysis: C 58 H 45 BN4O3Pt(%) calculated values: C, 66.23; H, 4.31; B, 1.03; N, 5.33; O, 4.56; Pt, 18.55. Found values: C, 66.30; H, 4.28; B, 1.11; N, 5.29; O, 4.54; Pt, 18.51.
[0124] Example 6: Synthesis of Compound 2-13
[0125] The synthetic route of compound E5 is as follows:
[0126]
[0127] C3 (1.18 g, 2.2 mmol), D1 (1.27 g, 2.5 mmol), KOAC (1.94 g, 19.8 mmol) were added to a 100 mL double-necked flask, and a mixture of THF / H2O (30 mL / 7.0 mL) was added to a 100 mL double-necked flask. Finally, Pd(PPh3)4 (127 mg, 0.11 mmol) was added under a nitrogen atmosphere, and nitrogen was replaced more than three times, and refluxed at 70 ° C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product E5 (1.18 g, yield: 64%) as a white solid.
[0128] MS(EI): m / z 838.41[M + ]; Combustion method element analysis: C 56 H 51BN4O3 (%) calculated value: C, 80.18; H, 6.13; B, 1.29; N, 6.68; O, 5.72. Found value: C, 80.22; H, 6.09; B, 1.26; N, 6.72; O, 5.68.
[0129] The synthetic route of compound E6 is as follows:
[0130]
[0131] Under nitrogen atmosphere, E5 compound (671.0 mg, 0.8 mmol), iodomethane (136.3 mg, 0.96 mmol), and acetone (8 mL) were added to a double-necked flask in sequence, and the nitrogen was replaced at least three times, and then stirred at room temperature for 48 h. The solid product was evaporated and dried under reduced pressure, and the compound (743.3 mg, 0.678 mmol) obtained by silica gel column chromatography was directly used for the next step reaction, and MeOH / H2O (6 mL / 4 mL) was added, and stirred at room temperature for 30 min until the solid was completely dissolved, and then ammonium hexafluorophosphate (122.2 mg, 0.75 mmol) was added to the reaction bottle, and stirring was continued for 72 h at room temperature, and the precipitate was filtered and washed with deionized water and ethanol to obtain E6 compound (487.4 mg, yield: 61%).
[0132] MS(EI): m / z 998.39[M + ]; Combustion method element analysis: C 57 H 54 BF6O3P (%) calculated value: C, 83.19; H, 6.71; B, 0.99; N, 7.66; O, 1.46 Found value: C, 83.21; H, 6.72; B, 0.10; N, 7.59; O, 1.41.
[0133]
[0134] E6 (628.6 mg, 0.4 mmol), (1,5-cyclooctadiene) platinum (II) dichloride (161.0 mg, 0.43 mmol), sodium acetate (98.4 mg, 1.2 mmol) were added to a high pressure reaction bottle containing THF (30 mL), replaced with nitrogen more than three times, and reacted at 120 ° C for 48 h. After the reaction was completed, it was cooled to room temperature and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product 2-13 (184.3 mg, yield: 44%) as a white solid.
[0135] MS (EI): m / z 1046.38 [M + ]; Combustion method element analysis: C 57 H52 BN4O3Pt(%) calculated values: C, 65.39; H, 5.01; B, 1.03; N, 5.35; O, 4.58; Pt, 18.63. Found values: C, 65.41; H, 5.06; B, 0.99; N, 5.59; O, 4.61; Pt, 18.58.
[0136] Example 7: Synthesis of Compound 3-2
[0137] The synthetic route of compound F-1 is as follows:
[0138]
[0139] Compound 5 (1.13 g, 3 mmol), KOAC (883.3 mg, 9 mmol), biboronic acid pinacol ester (1.52 g, 6 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (109.8 mg, 0.15 mmol), ultra-dry 1,4-dioxane solvent (70 mL) were added to a 250 mL double-necked reaction bottle, and nitrogen was replaced more than three times, and refluxed at 120 ° C for 48 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with deionized water and dichloromethane. The collected organic phase was dried with anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product F-1 (990.5 mg, yield: 78%) as a light yellow solid.
[0140] MS (EI): m / z 423.16 [M + ]; Combustion method element analysis: C 26 H 22 BNO4 (%) calculated value: C, 73.78; H, 5.24; B, 2.55; N, 3.31; O, 15.12. Found value: C, 73.81; H, 5.16; B, 2.58; N, 3.34; O, 15.15.
[0141] The synthetic route of compound F-2 is as follows:
[0142]
[0143] Under nitrogen atmosphere, F1 (846.5 mg, 2 mmol), B3 (962.7 mg, 2 mmol), KOAC (1.77 g, 18.0 mmol), THF / H2O (20 mL / 4.5 mL) were added to a 100 mL double-necked flask, and Pd(PPh3)4 (116 mg, 0.1 mmol) was added at last. The mixture was replaced with nitrogen more than three times and refluxed at 75°C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with ethyl acetate and deionized water. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product F-2 (851.3 g, yield: 61%) as a white solid.
[0144] MS (EI): m / z 697.21 [M + ]; Combustion method element analysis: C 46 H 27 Calculated value of N5O3 (%): C, 79.18; H, 3.90; N, 10.04; O, 6.88. Found value: C, 79.21; H, 3.94; N, 10.11; O, 6.80.
[0145] The synthetic route of compound 3-2 is as follows:
[0146]
[0147] In a double-necked flask, add F-2 compound (558.2 mg, 0.8 mmol), potassium chloroplatinate (365.3 mg, 0.88 mmol), tetrabutylammonium bromide (25.8 mg, 0.08 mmol), acetic acid (35 mL), replace nitrogen at least three times, and stir at room temperature for 24 hours. Then transfer the reaction flask to an oil bath and reflux at 110 ° C for three days. After the reaction is completed and returned to room temperature, slowly add deionized water (44 mL), stir for 5-10 minutes, filter the precipitate, and wash with deionized water three times. The solid product is dried by vacuum rotary evaporation and separated by silica gel column chromatography to obtain the product compound 1-3 (292.2 mg, yield: 41%) as a light yellow solid.
[0148] MS (EI): m / z 890.16 [M + ]; Combustion method element analysis: C 46 H 25 Calculated values for N5O3Pt (%): C, 62.02; H, 2.83; N, 7.86; O, 5.39; Pt, 21.90 Found values: C, 61.97; H, 2.78; N, 7.80; O, 5.34; Pt, 21.83.
[0149] Example 8: Synthesis of Compound 3-5
[0150] The synthetic route of compound F-3 is as follows:
[0151]
[0152] C3 (1.61 g, 3 mmol), F-1 (1.44 g, 3.4 mmol), KOAC (2.65 g, 27 mmol) were added to a 100 mL double-necked flask, and a mixture of THF / H2O (35 mL / 8.0 mL) was added to a 100 mL double-necked flask. Finally, Pd(PPh3)4 (173.3 mg, 0.15 mmol) was added under a nitrogen atmosphere, and the nitrogen was replaced more than three times, and refluxed at 70 ° C for 24 h. After the reaction was completed and cooled to room temperature, the reaction mixture was extracted with saturated brine and ethyl acetate. The collected organic phase was dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain the product F-3 (1.60 g, yield: 71%) as a white solid.
[0153] MS(EI): m / z 753.27[M + ]; Combustion method element analysis: C 50 H 35 Calculated value of N5O3 (%): C, 79.66; H, 4.68; N, 9.29; O, 6.37 Found: C, 79.58; H, 4.72; N, 9.20; O, 6.29.
[0154]
[0155] Under nitrogen atmosphere, F-3 compound (753.86 mg, 1 mmol), iodomethane (170.3 mg, 1.2 mmol), and acetone (10 mL) were added to a double-necked flask in sequence, and the nitrogen was replaced at least three times, and then stirred at room temperature for 48 h. The solid product was evaporated and dried under reduced pressure, and the compound (632.40 mg, 0.84 mmol) obtained by silica gel column chromatography was directly used for the next step reaction, and MeOH / H2O (8 mL / 5.3 mL) was added, and stirred at room temperature for 30 min until the solid was completely dissolved, and then ammonium hexafluorophosphate (151.6 mg, 0.93 mmol) was added to the reaction bottle, and stirred at room temperature for 72 h, and diluted with deionized water, and the precipitate was filtered, and washed with deionized water and ethanol to obtain F-4 compound (657.9 mg, yield: 72%).
[0156] MS(EI): m / z 998.39[M + ]; Combustion method element analysis: C 51 H 38Calculated value of F6N5O3P(%): C, 67.03; H, 4.19; F, 12.47; N, 7.66; O, 5.25; P, 3.39 Found value: C, 67.05; H, 4.11; F, 12.41; N, 7.61; O, 5.18; P, 3.30.
[0157]
[0158] F-4 (639.7 mg, 0.7 mmol), (1,5-cyclooctadiene) platinum (II) dichloride (276.8 mg, 0.74 mmol), sodium acetate (173.3 mg, 2.1 mmol) were added to a high pressure reaction bottle containing THF (40 mL), replaced with nitrogen more than three times, and reacted at 120 ° C for 48 h. After the reaction was completed, it was cooled to room temperature and concentrated by rotary evaporation. The crude product was further separated by silica gel column chromatography to obtain a white product 3-5 (236.6 mg, yield: 35%).
[0159] MS (EI): m / z 1304.57 [M + ]; Combustion method element analysis: C 50 H 36 Calculated values for N5O4Pt (%): C, 62.17; H, 3.76; N, 7.25; O, 6.63; Pt, 20.20 Found values: C, 61.54; H, 3.75; N, 7.19; O, 6.59; P, 20.18.
[0160] The transient fluorescence spectrum of the compound 1-1 molecule of Example 1 was measured by Edinburgh-steady-state / transient fluorescence spectrometer FLS980, as shown in FIG. Figure 1 As shown. Figure 2 As shown, the thin film structure is used to prepare an organic electroluminescent device. The specific steps are: the indium tin oxide glass substrate is ultrasonically treated with acetone, ethanol, and deionized water for 10 minutes, then blown dry with a nitrogen gun, and then subjected to ultraviolet ozone treatment for 20 minutes. Then, the substrate is sent to a vacuum evaporation chamber and the substrate is subjected to the following steps: Figure 2 The structure shown is subjected to vapor deposition of various functional layers, and then encapsulated with UV-curing adhesive, and finally the sample is taken out to conduct an electroluminescent performance test in the air. Figure 2In the invention, glass substrate 1, anode 2 (indium tin oxide), hole injection layer 3 (molybdenum oxide), hole transport layer 4 (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline], TAPC), exciton blocking layer 5 (1,3-bis(carbazole-9-yl)benzene, mCP), light-emitting layer 6 (a mixed film of the high entropy charge transfer guest and host material of the present invention), hole blocking layer 7 (bis[2-((oxy)diphenylphosphino)phenyl]ether, DPEPO), electron transport layer 8 (3',1"-terphenyl-3,3"-diyldipyridine, TmPyPB), electron injection layer 9 (8-hydroxyquinoline-lithium, Liq) and cathode layer 10 (aluminum). The brightness, spectrum and voltage-current curve of the device are obtained by simultaneously collecting the spectral brightness meter PhotoResearch735 and the voltage-current source Keithley 2400 at one time. The current efficiency, power efficiency, external quantum efficiency and color coordinates can be obtained by converting and correcting the above data.
[0161] The above is only a preferred specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed by the present invention should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.
Claims
1. A platinum complex derivative comprising intramolecular high entropy charge transfer, characterized in that The platinum complex derivative containing intramolecular high entropy charge transfer includes a light-emitting unit induced by a multiple resonance effect and a unit based on a platinum complex. The platinum complex derivative containing intramolecular high entropy charge transfer is shown in general formula (1): Among them, the A unit is selected from a boron atom or a nitrogen atom; R1, R2 and R3 are the same or different; a, b and c are independently selected from 0 or 1, and a+b+c is greater than or equal to 2; I, II and III are the same or different, and each is independently selected from one or more five-membered rings or six-membered rings or heterocycles, or a condensed system composed of one or more five-membered rings or six-membered rings or heterocycles; IV is a unit based on a platinum complex.
2. A platinum complex derivative comprising intramolecular high entropy charge transfer as claimed in claim 1, characterized in that: IV is selected from the group represented by formula (5) or formula (6); in, represents the connection point with unit I in formula (1); substituents L1, L2, L3 and L4 are the same or different and are selected from hydrogen atoms, substituted or unsubstituted C 1~12 Alkyl, C 6~18 Aryl or C 5-18 A fused system consisting of a heteroaryl group, one or more five-membered rings or six-membered rings or heterocyclic rings; L5 is selected from C 1~12 Alkyl, C 6~18 Aryl or C 5-18 The heteroaryl group.
3. A platinum complex derivative comprising intramolecular high entropy charge transfer as claimed in claim 1, characterized in that: When the A unit is a boron atom, R1, R2 and R3 are each independently selected from a carbon atom, an oxygen atom, a sulfur atom, a selenium atom, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; the light-emitting unit has the structural characteristics of formula (2): Wherein, L6 and L7 are the same or different and are independently selected from C 1-12 alkyl, one or more five-membered rings or six-membered rings or heterocyclic rings, a fused system consisting of one or more five-membered rings or six-membered rings or heterocyclic rings, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; D is selected from carbon atom, oxygen atom, sulfur atom, selenium atom, N-(C 6-14 Aryl), N-(C 6-14 Aryl) and the fused system of the phenyl group where L6 is located, C 1-6 Alkyl substituted 6-membered heteroaryl, C 1-6 A condensed system of an alkyl-substituted 6-membered heteroaryl group and the phenyl group where L6 is located; E is selected from a hydrogen atom, a carbon atom, an oxygen atom, N-(C 6-14 Aryl), C 1-6 Alkyl substituted 6-membered heteroaryl; --- indicates connection or non-connection.
4. A platinum complex derivative comprising intramolecular high entropy charge transfer as claimed in claim 1, characterized in that: When the A unit is a nitrogen atom, R1 and R2 are selected from carbonyl groups, and R3 is selected from hydrogen atoms, carbon atoms, oxygen atoms, sulfur atoms, selenium atoms, carbonyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; the light-emitting unit has the structural features of formula (3) or formula (4): wherein L8 and L9 are the same or different and are independently selected from C1-12 alkyl, one or more five-membered rings or six-membered rings or heterocycles, a fused system consisting of one or more five-membered rings or six-membered rings or heterocycles, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted C 6~60 Aryl, substituted or unsubstituted C 5~60 Heteroaryl; E is selected from a carbon atom or a carbonyl group; --- indicates connection or non-connection.
5. A platinum complex derivative comprising intramolecular high entropy charge transfer as claimed in claim 1, characterized in that: The platinum complex derivative comprising intramolecular high entropy charge transfer has a structure as shown in any of the following:
6. Use of a platinum complex derivative comprising intramolecular high entropy charge transfer as claimed in any one of claims 1 to 5, characterized in that: The platinum complex derivative containing intramolecular high entropy charge transfer is applied to an organic electroluminescent device; the organic electroluminescent device comprises an anode, an organic functional layer, an organic light-emitting layer and a cathode; the organic functional layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer; the platinum complex derivative containing intramolecular high entropy charge transfer is located in the organic light-emitting layer as a light-emitting material.