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SO2-containing spiro pyrrolocarbazole compound and application thereof

A technology of rolocarbazoles and compounds, which is applied in the field of organic electroluminescence display, can solve problems such as triplet annihilation, triplet-polaron annihilation, and efficiency decline, so as to reduce driving voltage, improve photoelectric performance, Effect of High Film Stability

Inactive Publication Date: 2022-01-11
北京云基科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the lifetime of the excited state of phosphorescent materials is long, and triplet-triplet annihilation and triplet-polaron annihilation are easy to form when the triplet exciton concentration is high, which seriously reduces the efficiency.

Method used

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  • SO2-containing spiro pyrrolocarbazole compound and application thereof
  • SO2-containing spiro pyrrolocarbazole compound and application thereof
  • SO2-containing spiro pyrrolocarbazole compound and application thereof

Examples

Experimental program
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preparation example Construction

[0044]According to the preparation method provided by the present invention, those skilled in the art can use known common means to realize, such as further selecting a suitable catalyst and solvent, determining a suitable reaction temperature, time, etc., which are not particularly limited in the present invention. The solvents, catalysts, bases and other raw materials used in the preparation process can be synthesized through open commercial channels or methods known in the art.

[0045] Using the preparation method provided by the invention, a series of compounds represented by general formula (I) were prepared.

[0046] Synthesis of Intermediates M1~M8

[0047] Synthesis of intermediate M1

[0048]

[0049] The synthetic route is as follows:

[0050]

[0051] The synthesis process comprises the following specific steps:

[0052] (1) Add 2-bromo-6-iodobiphenyl (35.8g, 0.10mol) and anhydrous tetrahydrofuran into a dry 1L three-necked flask under nitrogen protection....

Embodiment 1

[0085] The synthesis of embodiment 1 compound I-1

[0086]

[0087] The synthetic route is as follows:

[0088]

[0089] The preparation process includes: taking a 1L three-neck flask, equipped with magnetic stirring, adding potassium tert-butoxide (11.2g, 0.1mol), carbazole (16.7g, 0.1mol) and 400ml of toluene in sequence after nitrogen replacement; adding ( 0.4 g, 2 mmol) tri-tert-butylphosphine and (0.2 g, 1 mmol) palladium acetate. After the addition, heat up to 85°C; start to add dropwise a solution consisting of (64.7g, 0.1mol) M1 and 100ml of toluene, control the temperature at 80-120°C for 4 hours, and the reaction ends. Adjust to neutrality, separate the organic phase, extract, dry, perform column chromatography, and spin dry the solvent to obtain 61.52 g of light yellow solid with a yield of about 75%.

[0090] Product MS (m / e): 734.2; Elemental analysis (C 51 h 30 N 2 o 2S): theoretical value C: 83.36%, H: 4.11%, N: 3.81%; measured value C: 83.30%, H: 4....

Embodiment 2

[0091] Synthesis of Example 2 Compound I-14

[0092]

[0093] The synthetic route is as follows:

[0094]

[0095] The preparation process includes: adding M1 (64.7g, 0.1mol), 9-(4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (36.9g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 250mL, ethanol 150mL, water 100mL , the reaction system was protected by nitrogen replacement and added Pd(PPh 3 ) 4 (11.5g, 10mmol), magnetically stirred and heated to reflux reaction (system temperature 70-80°C) for 3 hours, and the reaction was stopped. The solvent was evaporated by subtraction, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, petroleum ether / ethyl acetate (2:1) column chromatography, spin-dried solvent, ethyl acetate beating, filtered to obtain 69.85g product I-14 , yield 86.2%.

[0096] Product MS (m / e): 810.23; Elemental analysis (C 57 h 34 N 2 o 2 S): theoretical value C: 84.42%, H: 4.23%, N: 3.45%; meas...

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Abstract

The invention relates to the technical field of organic electroluminescent display, particularly discloses an organic material of a SO2-containing spiro pyrrolocarbazole compound, and also discloses an application of the organic material in an organic electroluminescent device. The SO2-containing spiro pyrrolocarbazole compound provided by the invention is shown as a general formula (I), can be applied to the field of organic electroluminescence, and can be used as a luminescent layer main body material. The compound with the structure provided by the invention is applied to an OLED device, the driving voltage can be reduced, and the luminous efficiency of the device can be improved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence display, in particular to a novel SO-containing 2 The spiro-ring pyrrolocarbazole compound, also relates to its application in organic electroluminescent devices. Background technique [0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescence display devices (OLEDs). Among them, OLEDs have a series of advantages such as self-luminescence, low-voltage DC drive, light and thin power saving, full curing, wide viewing angle, and rich colors. Comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/10C07D519/00H01L51/00H01L51/50H10K99/00
CPCC07D495/10C07D519/00H10K85/657H10K85/6572H10K50/11
Inventor 黄春雪李仲庆梁现丽杭德余曹占广班全志段陆萌
Owner 北京云基科技股份有限公司
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