Organic electroluminescent material and its application

A technology selected from aromatic groups, applied in the field of organic electroluminescence display, can solve the problems of device performance attenuation, low luminous brightness and efficiency, and difficulty in actual production

Active Publication Date: 2006-10-04
TSINGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The basic structure of an organic EL device includes anode/hole injection and transport layer/organic light-emitt

Method used

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  • Organic electroluminescent material and its application
  • Organic electroluminescent material and its application
  • Organic electroluminescent material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0030] Preferred embodiment: the compounds of the present invention are all prepared by reacting aryl or heterocyclic aryl boronic acid with the precursor of dibromobenzoxadiazole compounds.

[0031] Preparation of raw material arylboronic acid:

[0032] Most of the aryl boronic acid raw materials used in the present invention are purchased from Bailingwei Company, and the parent body of dibromobenzoxadiazole and part of aryl boronic acid are synthesized according to the following method.

[0033] Synthesis of 4-biphenylboronic acid:

[0034] Reaction formula:

[0035]

[0036] Process: In a 100ml three-neck flask equipped with magnetic stirring, reflux condenser and nitrogen protection device, dissolve 5.83 grams of 4-bromobiphenyl (0.025mol) in 20mlTHF, add 0.85 grams of magnesium chips (0.035mol), 0.5ml bromoethane, warm to start the reaction, reflux for 2 hours. Cool 3.12 grams (3.25ml, 0.03mol) of trimethyl borate to -5°C to -10°C with an ice-salt bath, slowly add 4...

Embodiment 1

[0071] Example 1 4,7-diphenyl-2,1,3-benzoxadiazole (compound i-4)

[0072] Reaction formula:

[0073]

[0074] process:

[0075] In a 100mL three-necked flask equipped with a magnetic stirrer, a condensing reflux device and a nitrogen protection device, 4,7-dibromobenzoxadiazole (1.50 g, 5.2 mmol), anhydrous potassium carbonate (3.59 gram, 26.0mmol), 4-biphenylboronic acid (2.52 gram, 12.5mmol), two (triphenylphosphine) palladium dichloride (0.70 gram, 1.0mmol) and by toluene, ethanol and water (volume ratio is 3: 3:2) of the mixed solution consisting of 65 mL, heated to reflux under the protection of nitrogen, and reacted for 24 hours. Remove from heat and cool to room temperature.

[0076] Pour the reaction solution into 50 mL of water, filter under reduced pressure, rinse the filter cake with water and ethyl acetate in sequence, dry the solid, and recrystallize with toluene to obtain a yellow product.

[0077] Product MS (m / e): 424.2; Elemental analysis (C 30 h 20 ...

Embodiment 2

[0078] Example 2 4,7-bis(1-naphthyl)-2,1,3-benzoxadiazole (compound i-5)

[0079] Reaction formula:

[0080]

[0081] The process is the same as in Example 1, except that the raw material is replaced with 1-naphthylboronic acid to obtain a yellow product.

[0082] Product MS (m / e): 372.4; Elemental analysis (C 26 h 16 N 2 O): theoretical value C: 83.85, H: 4.33, N: 7.52; measured value C: 83.82, H: 4.30, N: 7.47.

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Abstract

The related new compound for an organic electroluminescent device with super performancehas structural formula as follow; wherein, n is integer within 1-4, Ar and Ar' are selected independently from H atom, substituted or unsubstituted aromatic base, or hetero-ring/ fused-ring /condensed-hetero-ring aromatic base, but not H atoms at one time; R1 and R2 are from halogen atom, substituted or unsubstituted alkyl/alkoxy/aminoalkyl/sulfuralkyl/aromatic/hetero- ring aromatic. This invention has well feature and wide application.

Description

technical field [0001] The invention relates to an organic electroluminescence material and its application in an organic electroluminescence device, belonging to the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescent devices (hereinafter referred to as organic EL) are widely used in various fields due to their ultra-thin, fully cured, self-luminous, fast response, good temperature characteristics, and flexible display. [0003] Research on organic EL began in the 1960s. In 1963, Pope et al. (J.Chem.Phys.1963, 38:2042~2043) studied the blue electroluminescence of anthracene single crystal (10~20μm), because the anthracene single crystal light-emitting layer was thick and the electrodes used Due to the constraints of materials (silver colloid and sodium chloride solution), the luminous starting voltage of the device is as high as 400V, and the efficiency and brightness are low. However, the discovery opens up a n...

Claims

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Application Information

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IPC IPC(8): C07D271/12C09K11/06H05B33/14
Inventor 邱勇李建仁李银奎高裕第
Owner TSINGHUA UNIV
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