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Quinazoline triazole derivative and application thereof in field of organic electroluminescence

A compound and unsubstituted technology, applied in the field of new organic heterocyclic compounds, can solve the problem of not specifically disclosing organic electroluminescent compounds, etc., and achieve the effects of wide energy gap, simple device structure, and improved energy level

Active Publication Date: 2019-05-31
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above references do not specifically disclose an organic electroluminescent compound in which quinazolinotriazole is introduced as an electron-deficient group into the host material structure

Method used

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  • Quinazoline triazole derivative and application thereof in field of organic electroluminescence
  • Quinazoline triazole derivative and application thereof in field of organic electroluminescence
  • Quinazoline triazole derivative and application thereof in field of organic electroluminescence

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the preparation of compound C1

[0055]

[0056] Preparation of Compound 1-1

[0057] 2,4-Dichloroquinazoline (500g, 2.5mol) was dissolved in a 10L ethanol flask, and hydrazine hydrate (470g, 7.5mol, 80% aqueous solution) was added dropwise at 5°C under stirring, and the temperature was kept below 10°C. After the dropwise addition, the mixture was naturally raised to room temperature for 1 hour, and the obtained solid was filtered with suction, washed with water and ethanol, and dried in the air to obtain compound 1-1 (415 g, 86%) as an off-white solid.

[0058] Preparation of compound 1-2 (reference J.Heterocyclic chem.27,497,1990)

[0059] Compound 1-1 (200g, 1.03mol) was added to a flask containing 2L of ethanol, and benzaldehyde (120g, 1.13mol) was added dropwise under stirring at room temperature. After the addition was complete, the stirring reaction was continued for 30 minutes, and the resulting solid was filtered and washed with ethanol and ...

Embodiment 2

[0066] Embodiment 2: the preparation of compound C2

[0067]

[0068] Preparation of compound 2-1

[0069] Compound 1-1 (20g, 103mmol) was added to a flask containing 200mL of ethanol, and phenyl-p-methylformaldehyde (15g, 125mmol) was added dropwise under stirring at room temperature. Rinse with n-hexane and dry to obtain compound 2-1 (19.8 g, 65%) as a yellow solid.

[0070] Preparation of compound 2-2

[0071] Compound 2-1 (19.8g, 67mmol) was added to a flask containing 200L of ethanol, and iodobenzene acetate (25.8g, 80.1mmol) was added in batches under stirring at room temperature. Stirring was continued for 1.5 hours after the addition, and TLC showed that the reaction was complete. After adding 200 mL of n-hexane and stirring for 5 minutes, the resulting solid was suction-filtered, rinsed with n-hexane, and dried as a light brown solid compound 2-2 (14.6 g, 74%).

[0072] Preparation of compound C2

[0073] Compound 2-2 (7.35g, 25mmol), compound 1-4 (10g, 23.64mm...

Embodiment 3

[0074] Embodiment 3: the preparation of compound C6

[0075]

[0076] Preparation of compound 3-1

[0077] Compound 1-1 (20g, 103mmol) was added to a flask containing 200mL of ethanol, and 3-formaldehyde pyridine (13.3g, 125mmol) was dropped under stirring at room temperature. Rinse with n-hexane and dry to obtain compound 3-1 (16.3 g, 56%) as a yellow solid.

[0078] Preparation of compound 3-2

[0079] Compound 3-1 (16.3g, 57.6mmol) was added to a flask containing 200L of ethanol, and iodobenzene acetate (22.3g, 69.1mmol) was added in batches under stirring at room temperature. Stirring was continued for 1.5 hours after the addition, and TLC showed that the reaction was complete. After adding 200 mL of n-hexane and stirring for 5 minutes, the obtained solid was suction-filtered, rinsed with n-hexane, and dried to obtain light brown solid compound 3-2 (10 g, 70%).

[0080] Preparation of compound C6

[0081] Add compound 2-2 (7.03g, 25mmol), compound 1-4 (10g, 23.64mmo...

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Abstract

The invention discloses a quinazoline triazole derivative as shown in formula (1) and application thereof in organic light-emitting materials. The quinazoline triazole derivative is high in glass-transition temperature, high in melting point and high in carrier transport and light-emitting efficiency. An organic electroluminescence device which is low in drive voltage and high in light-emitting efficiency is obtained by applying the quinazoline triazole derivative to a host material using an organic light-emitting functional layer as the light-emitting layer.

Description

technical field [0001] The invention relates to a new organic heterocyclic compound, in particular to a new class of quinazolinotriazole derivatives and their application in organic electroluminescent devices. Background technique [0002] In 1998, Professor Ma Yuguang of Jilin University prepared an electrophosphorescent device by doping poly-N-vinylcarbazole (PVK) with an osmium complex [Os(CN)2(PPh3)2bpy] (Synthetic Metals, 1998, 94: 245-248). In the same year, Thomson and Forrest cooperated to dope the phosphorescent material platinum octaethylporphyrin (PtOEP) in 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer of the electroluminescent device, so that the internal quantum efficiency and external quantum efficiency were improved respectively. to 23%, 4% (Nature, 1998, 395: 151-154; Appl. Phys. Lett., 1999, 75: 4-6). Since then, organic light-emitting devices based on phosphorescent metal complexes have developed rapidly. Different from traditional organ...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D519/00C07D491/048C07D495/04C09K11/06H01L51/50H01L51/54
Inventor 孙恩涛范洪涛刘嵩张向慧
Owner BEIJING ETERNAL MATERIAL TECH
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