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Soluble resin substituted anthryl deep blue-light emitting material and preparation and application thereof

A blue-light material and soluble technology, which is applied in the direction of luminescent materials, semiconductor/solid-state device manufacturing, electrical components, etc., can solve the problems of lower efficiency and easy quenching of luminescence, and achieve inhibition of aggregation, good film shape stability, and good heat dissipation. The effect of stability

Active Publication Date: 2019-02-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The soluble branch-substituted anthracenyl deep blue light material of the present invention uses phenyl-bridged dianthryl as the core, and introduces electron-withdrawing or electron-deficient end groups while using soluble dendron-substituted aryl end groups, which solves the problem of existing problems. The luminescence of anthracenyl blue light materials in the solid state is easy to quench, which promotes electron injection and transmission, which is conducive to reducing the efficiency roll-off of blue light materials at high current densities, and improves the solubility of light-emitting materials, which is conducive to synthesis and purification.

Method used

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  • Soluble resin substituted anthryl deep blue-light emitting material and preparation and application thereof
  • Soluble resin substituted anthryl deep blue-light emitting material and preparation and application thereof
  • Soluble resin substituted anthryl deep blue-light emitting material and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1, anthracenyl blue light material CN-1

[0048] An anthracenyl TTA blue light material CN-1[4-(10-(4-(10-(4,4"-bis-tert-butyl-[1,1':3',1"-triphenyl]- 5'-yl) anthracene-9-yl) phenyl) anthracene-9-yl) benzonitrile], its structure is as follows:

[0049]

[0050] The preparation method of the anthracenyl blue light material CN-1 comprises the following steps:

[0051] Step 1, the preparation of 4-(anthracene-9-yl)benzonitrile:

[0052]

[0053] Under nitrogen atmosphere, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (10.7g, 46.7mmol), 9 -Bromoanthracene (12.6g, 49mmol), potassium carbonate aqueous solution (30mL, 2M) was added to tetrahydrofuran (150mL), stirred for 20min, and tetrakis(triphenylphosphine) palladium (180mg, 0.155mmol) was added, overnight at 70°C Reaction, tetrahydrofuran was distilled off under reduced pressure, then extracted and dried, separated and purified by silica gel column to obtain a golden yellow solid (eluent: PE / ...

Embodiment 2

[0071] Example 2, anthracenyl blue light material Py-2

[0072] An anthracenyl blue light material Py-2[3-(10-(4-(10-(4,4"-di-tert-butyl-[1,1':3',1"-triphenyl]- 5'-yl) anthracene-9-yl) phenyl) anthracene-9-yl) pyridine], its structure is as follows:

[0073]

[0074] The preparation method of the anthracenyl blue light material Py-2 comprises the following steps:

[0075] Step 1, the preparation of 3-(anthracene-9-yl)pyridine:

[0076]

[0077] Under nitrogen atmosphere, pyridine-3-boronic acid (2.5g, 20mmol), 9-bromoanthracene (8.5g, 24mmol), potassium carbonate solution (20mL, 2M), ethanol (10mL) were added to toluene (50mL), After 20min, tetrakis(triphenylphosphine)palladium (160mg, 0.14mmol) was added and heated to reflux for 12h. After the reaction, the toluene was distilled off under reduced pressure, extracted and dried, and purified by silica gel column separation (PE / DCM). 2 g of white solid were obtained (yield 51%).

[0078] Step 2, the preparation of 3-(10-...

Embodiment 3

[0086] Example 3, anthracenyl blue light material Q-3

[0087] An anthracenyl blue light material Q-3[2-(4-(10-(4-(10-(4,4"-di-tert-butyl-[1,1':3',1"-terphenyl ]-5'-yl) anthracene-9-yl) phenyl) anthracene-9-yl) phenyl) quinoline], its structure is as follows:

[0088]

[0089] The preparation method of the anthracenyl blue light material Q-3 comprises the following steps:

[0090] Step 1, the preparation of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline:

[0091]

[0092] Under nitrogen atmosphere, dissolve 2-(4-bromophenyl)quinoline (3.5g, 12.3mmol), bis-pinacol borate (4.7g, 18.5mmol), potassium acetate (3.6g, 36mmol) In 50mL tetrahydrofuran, after degassing for 20min, add bis(triphenylphosphine)palladium dichloride (100mg, 0.142mmol), and heat to reflux overnight for reaction. Recrystallization afforded 3 g of product (73% yield).

[0093] Proton NMR spectrum analysis results: 1 H NMR (500MHz, CDCl 3 )δ8.26-8.15 (m, 4H), 7.97 (d, J = 8.2Hz, 2...

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Abstract

The invention belongs to the technical field of blue-light electroluminescent materials and discloses a soluble resin substituted anthryl deep blue-light emitting material and preparation and the application thereof. The structural formula of the anthryl deep blue-light emitting material is I, wherein R is one of electricity absorbing structural units. The invention also discloses a preparation method of the anthryl deep blue-light emitting material. The soluble resin substituted anthryl deep blue-light emitting material has the characteristics of being good in solubility, thermal stability, film shape stability and easy to synthesize and purify and the like. In a non-doped electroluminescence device, the material shows a high light-emitting efficiency and a low-efficiency roll-off, and has an important application prospect.

Description

technical field [0001] The invention belongs to the technical field of blue photoluminescent materials, and relates to organic molecular blue photoluminescent materials, in particular to a soluble branch-substituted anthracenyl deep blue material and its preparation method and application. Application of the anthracene-based deep blue light material of the invention in electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) are leading the development of information display and lighting technologies due to their advantages of self-luminescence, flexibility, and low energy consumption. Compared with green and red light materials, designing high-efficiency and high-stable blue light-emitting electroluminescent materials is of great significance for OLED display, especially OLED lighting. [0003] Blue light materials can be divided into traditional blue light fluorescent materials, blue light phosphorescent materials, TADF (thermally ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07D213/16C07D215/04C09K11/06H01L51/54
CPCC09K11/06C07C255/50C07D213/16C07D215/04C09K2211/1029C09K2211/1011C09K2211/1007H10K85/626H10K85/654H10K85/6572
Inventor 朱旭辉彭灵魏鑫峰王梅王林叶曹镛
Owner SOUTH CHINA UNIV OF TECH
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