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Preparation and application of novel umbrella-type light-emitting material with pyrrole structure

A luminescent material, pyrrole technology, applied in organic chemistry, semiconductor/solid-state device manufacturing, electrical components, etc., can solve the problems of luminous efficiency and service life that cannot satisfy device manufacturers, achieve good industrialization prospects, improve efficiency, reduce The effect of drive voltage

Inactive Publication Date: 2019-03-12
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, OLED organic light-emitting materials cannot meet the requirements of device manufacturers in terms of luminous efficiency and service life. It is particularly important to research and develop a high-performance OLED light-emitting material.

Method used

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  • Preparation and application of novel umbrella-type light-emitting material with pyrrole structure
  • Preparation and application of novel umbrella-type light-emitting material with pyrrole structure
  • Preparation and application of novel umbrella-type light-emitting material with pyrrole structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of intermediate

[0025]

[0026] In a 1000ml three-necked flask, add 40.0g of raw material A (303mmol) and 62.9g of raw material B (939mmol) under the condition of nitrogen gas, add 167g of K2CO3 (1210mmol), 400ml of NMP, heat up to 160 ℃ ~ 170 ℃, keep warm for 15h, TLC Detect that the reaction of the raw materials is complete; cool down to room temperature, filter, rinse the filter cake with NMP, remove the solvent, pass the filtrate through a silica gel column, and rotate the column solution under reduced pressure. Recrystallized with toluene to obtain 68 g of white substance C with a yield of 82.2% and a purity of 98% by HPLC. The molar ratio of the raw material A to the raw material B is 1:3.1, and the molar ratio of the raw material A to K2CO3 is 1:4

[0027] In a 1000ml three-necked flask, under nitrogen gas flow, add 60g of Substance C (219mmol), add 600ml of dichloroethane, and lower the temperature to 0-5°C. Then elemental brom...

Embodiment 2

[0029] Embodiment 2: the synthesis of compound 1

[0030]

[0031] The specific synthetic route of compound 1

[0032]

[0033] Under the protection of nitrogen, weigh 45g of intermediate I (127.7mmol), 31.6g of raw material D (127.7mmol), 33.8g of sodium carbonate (319mmol), 62g of ethanol, 78.8g of water (78.8ml), 143.4mg of Pd (OAC) 2 (0.638mmol), 608mgX-phos (1.28mmol), stirred and mixed with toluene, heated to 85-90°C, refluxed for 5-10 hours, sampling and pointing the plate, it showed that there was no intermediate 1 remaining, and the reaction was complete; naturally cooled to Filter at room temperature, pass the filtrate through a silica gel column, and rotary evaporate the column solution under reduced pressure until there is no fraction. The crude product is a gray solid, which is refined with toluene and dried to obtain 47g of compound 1. Yield: 77.3%, HPLC: 99.9%, HPLC-MS: The theoretical molecular weight of compound 1 is 475.5, and the actual detection resu...

Embodiment 3

[0034] Embodiment 3: the synthesis of compound 5

[0035]

[0036] The specific synthetic route of compound 5

[0037]

[0038] Under the protection of nitrogen, weigh 50g intermediate I (141.95mmol), sodium carbonate 37.61g (354.88mmol), water 87ml, catalyst 318.7mg Pd(OAC) 2 (1.42mmol), 1350mg X-phos (2.84mmol). After the addition of the materials, mix them evenly with toluene, heat to 90-100°C, add the THF solution of the raw materials E dropwise at this temperature (weigh 33.1g (156.2mmol) of the raw materials E in a 500ml Erlenmeyer flask, and mix them with tetrahydrofuran uniform to clear). Control the temperature at 90-100°C and add dropwise. After the dropwise addition is completed, keep warm and reflux at 90-100°C. The sampling plate shows that there is no intermediate remaining, and the reaction is complete. After washing the organic phase with water and drying it, it was passed through a silica gel column, and the column liquid was desolvated under reduced ...

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Abstract

The invention discloses preparation and an application of a novel umbrella-type light-emitting material with a pyrrole structure. The umbrella-type organic compound with the pyrrole structure has goodmolecular stability, a prepared OLED (organic light-emitting diode) device has superior photoelectric properties, high heat stability, low driving voltage and high efficiency, the service life of thedevice is prolonged, and the requirements of device manufacturers can be effectively met. The structure of the organic compound is as shown in a general formula (1), Ar is indicated as substituted orunsubstituted C6-60 aryl and 5-60 heterogeneous aryl containing one or more heteroatom, and the heteroatoms are nitrogen, oxygen or sulfur.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an umbrella-shaped organic compound material containing a pyrrole structure and its application in OLED light-emitting displays or lighting devices. technical background [0002] Organic Light Emitting Diode (OLED) is referred to as OLED display. Compared with liquid crystal display, OLED display has high brightness, thin volume, fast response, low power consumption, stable performance, high contrast, wide viewing angle, full color, and operating temperature range. Wide and other characteristics, highlighting a very superior application prospect in the field of display and lighting. [0003] Most OLED devices adopt a "sandwich" structure. The structure is composed of multiple functional layers with different roles, which are the anode layer of transparent metal oxide (usually indium tin oxide ITO), hole transport layer (HTL), light emitting layer (EML), e...

Claims

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Application Information

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IPC IPC(8): C07D207/323C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14H01L51/54
CPCC07D207/323C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 徐发往徐瑜璘张恒李彦龙张鑫于灏
Owner 烟台九目化学股份有限公司
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