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Novel organic electroluminescent material based on benzopyrroledione and application thereof

A technology of diketone benzopyrrole and electroluminescent materials, which is applied in the fields of luminescent materials, organic chemistry, circuits, etc., and can solve problems such as low efficiency and short device life

Active Publication Date: 2021-04-27
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These deficiencies directly lead to short device life and low efficiency of OLEDs / PLEDs, and become a "bottleneck" problem restricting the wide application of OLEDs / PLEDs.

Method used

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  • Novel organic electroluminescent material based on benzopyrroledione and application thereof
  • Novel organic electroluminescent material based on benzopyrroledione and application thereof
  • Novel organic electroluminescent material based on benzopyrroledione and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Synthesis of compound 1

[0022] 2-Hydroxy-2-phenylacetic acid (10g, 0.066mol), p-phenylenediamine (3.2g, 0.03mol) and chlorobenzene solution (100mL) were added to a 250mL single-necked bottle, and the mixture was heated to 130°C under nitrogen and stirred 18 hours. After the reactant was cooled to room temperature, it was poured into distilled water (100 mL); the mixture was washed with CH 2 Cl 2 (3×30mL) extraction; the organic layer was successively washed with water (60mL), dried, and evaporated under reduced pressure to remove the solvent; the residue was recrystallized with ethanol to obtain 7.3g of white solid (yield: 65%). 1 H NMR (CDCl 3 ,400M)δ:9.8(s,2H),7.57-7.52(m,4H),7.33-7.28(m,10H),6.02(s,2H),4.93(s,2H).

[0023] Synthesis of Compound 2

[0024] Compound 1 (6.0 g, 0.016 mol) and concentrated sulfuric acid (20 mL) were added into a 100 mL one-necked flask, and the mixture was stirred overnight at room temperature under nitrogen. After the...

Embodiment 2

[0034] Thermal stability test of H-DPP-CN in Example 1.

[0035]Under a nitrogen atmosphere, the heating rate was 20° C. / min, and the thermal stability of the compound H-DPP-CN was tested by a thermogravimetric analyzer. Depend on figure 1 It can be seen that the thermal decomposition temperature of the compound H-DPP-CN at a weight loss of 5% is greater than 400°C, indicating that the compound has good thermal stability and can be used to prepare electroluminescent devices by vacuum deposition.

Embodiment 3

[0037] The ultraviolet-visible absorption spectrum test of the compound H-DPP-CN in Example 1.

[0038] Compound H-DPP-CN was dissolved in toluene to form 10 -5 M solution, test the UV-Vis absorption spectrum of its solution at room temperature. Depend on figure 2 It can be seen that the compound H-DPP-CN has a strong UV-Vis absorption peak in the range of 300-450nm, which is mainly attributed to the transition absorption of π-π* in the molecule.

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Abstract

The invention discloses a novel organic electroluminescent material based on benzopyrroledione and application thereof. Benzopyrroledione is used as a skeleton, and a type of fused ring molecules with a larger conjugate plane are constructed through cyclization and other series reactions, so that the non-radiative transition of the molecules is reduced, and the luminous efficiency of the material is improved; electron donating groups and electron withdrawing groups are further introduced into the molecules to regulate and control the photophysical properties of the material; and an organic light-emitting device is prepared through a solution method by taking the material as a light-emitting layer doping agent, and the maximum external quantum efficiency (2.2%) is obtained.

Description

technical field [0001] The invention relates to a novel organic semiconductor material, in particular to a novel organic electroluminescent material based on diketone benzopyrrole and its application as a light-emitting layer material of an organic electroluminescent diode, belonging to the technical field of organic electroluminescent materials. [0002] technical background [0003] The 21st century is an era of information technology, and information has been closely integrated with the study, work and life of each of us. As a carrier of information transmission, displays play a pivotal role in our lives. In the field of various displays at present, liquid crystal display (LCD) occupies a leading position in the market due to its advantages such as mature production technology, high brightness, and low cost, but it also has disadvantages such as large size, high energy consumption, and inconvenient portability. In recent years, organic / polymer electroluminescent diodes (O...

Claims

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Application Information

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IPC IPC(8): C07D471/22C09K11/06H01L51/54
CPCC07D471/22C09K11/06C09K2211/1044H10K85/6572H10K50/11Y02E10/549
Inventor 王亚飞税新凤曹辰辉庞玉东
Owner 安徽秀朗新材料科技有限公司
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