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Organic material and applications of organic material in organic electroluminescent devices

A technology of organic materials and organic light-emitting layers, applied in the field of organic electroluminescence display, can solve problems such as small molecular weight, easy crystallization of materials, and low glass transition temperature

Active Publication Date: 2018-09-28
北京燕化集联光电技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the generally small molecular weight of the currently reported electron transport materials, the glass transition temperature of the material is low. During the use of the material, repeated charge and discharge, the material is easy to crystallize, and the uniformity of the film is destroyed, thereby affecting the service life of the material.

Method used

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  • Organic material and applications of organic material in organic electroluminescent devices
  • Organic material and applications of organic material in organic electroluminescent devices
  • Organic material and applications of organic material in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Synthesis of (Compound 1)

[0092] The synthetic route is as follows:

[0093]

[0094] 1) Synthesis of compound 1-1

[0095] A 1000 ml three-necked flask was equipped with a magnetic stirrer. After argon replacement, 26.49 g of 1-bromo-4-iodobenzene (purity 99%, 0.094 mol) and THF 500 ml were added in sequence according to the above amounts. Add 38ml of n-BuLi (concentration 2.5M, 0.095mol) dropwise at -90°C, and then add 8.4g of anthraquinone (purity 99%, 0.04mol). 20h. Add 500m water for hydrolysis, separate the liquid, extract the water phase with dichloromethane, combine the organic layers, evaporate the solvent to dryness, add 600ml of acetic acid, 36g of KI and 36g of sodium hypophosphite, reflux, react for 20 hours, cool down, filter, and water After rinsing, 17.49 g of a yellow product was obtained with a purity of 99.5% and a yield of 90%.

[0096] 2) Synthesis of compound 1

[0097] N 2 Under gas protection, 9,10-bis-(4-bromophenyl)anthracene 16.53...

Embodiment 2

[0110] Synthesis of (Compound 2)

[0111] The synthetic route is as follows:

[0112]

[0113] 1) Synthesis of compound 2-1

[0114] N 2 Under gas protection, in a 500mL three-necked flask, 9.58g (0.034mol) of 4-bromoiodobenzene, 7.21g (0.034mol) of 2-(3-fluorophenyl) benzimidazolyl, and 2.6g of copper iodide (purity AR0.0136mol), piperidinecarboxylic acid 5.4g (purity AR0.0136mol), potassium carbonate 35g (purity AR0.254mol). Use 600ml of DMF, magnetically stir, reflux for 30 hours, let cool and filter, and boil the crude yellow solid product several times with ethanol to obtain 9.96g of yellow solid with a purity of 99.6% and a yield of 80%.

[0115] 2) Synthesis of compound 2-2

[0116] Add 73.20g 4-(2-(3-fluorophenyl) benzimidazolyl)bromobenzene (compound 1-1, 0.2mol) and 1000ml tetrahydrofuran into a 2L dry and clean three-necked flask, protect it with nitrogen, and cool down to - 80°C, add 80ml of butyllithium dropwise, and react for 1 hour under temperature co...

Embodiment 3

[0120] Embodiment 3: the synthesis of compound 3

[0121]

[0122] N 2 Under air protection, 11.52 g of 6,12-dibromochryl (purity 98%, 0.03 mol), 24.91 g of 4-(2-(3-fluorophenyl) benzimidazolyl) phenylboronic acid were added to a 1000 mL three-necked flask (purity 99%, 0.075mol), tetrakistriphenylphosphine palladium 0.69g (purity AR, 0.0006mol), potassium carbonate 25.88g (purity AR, 0.188mol), toluene 300ml, ethanol 50ml, water 50ml. The above materials are heated to reflux. After 30 hours, the reaction was stopped, allowed to cool, and filtered to obtain a yellow solid, which was recrystallized from THF and repeated twice. 19.21 g of light yellow product was obtained with a purity of 99.80% and a yield of 80%.

[0123] Product MS (m / e): 800.28; Elemental analysis (C 56 h 34 f 2 N 4 ): theoretical value C: 83.98%, H: 4.28%, F: 4.74%, N: 7.00%; measured value C: 83.97%, H: 4.29%, F: 4.72%, N: 7.02%

[0124] According to the technical solutions of Example 2 and Examp...

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PUM

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Abstract

The present invention relates to the field of organic electroluminescence (OLED) display, particularly to an organic material and applications of the organic material in organic electroluminescent devices. According to the present invention, the novel OLED material has a structure represented by a general formula I, and a class of novel OLED materials with electron transport property are obtainedby introducing a substituent (2-(3-fluorophenyl)phenylimidazole) with electron transport property into the active position of a fused ring aromatic compound by using the fused ring aromatic compound as the center and using fluorine atom-containing benzimidazole as the terminal group; and the materials have advantages of high electron mobility, good film stability and suitable molecular energy levels, can be used in the organic electroluminescence field, and can be used as electron transport materials. The general formula I is defined in the specification.

Description

technical field [0001] The invention relates to a novel organic material and its application in organic electroluminescence devices, belonging to the technical field of organic electroluminescence display. 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 electroluminescent display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backlight, has a wider v...

Claims

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Application Information

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IPC IPC(8): C07D235/18C07D417/14C07D471/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D235/18C07D417/14C07D471/04C09K2211/1044C09K2211/1051C09K2211/1007C09K2211/1011H10K85/623H10K85/624H10K85/622H10K85/615H10K85/657H10K85/6572H10K50/16
Inventor 班全志杭德余马天凯
Owner 北京燕化集联光电技术有限公司
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