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Electroluminescent material and application thereof

An electroluminescent material, a secondary substitution technology, applied in the direction of luminescent materials, circuits, electrical components, etc., to achieve the effect of good thermal stability, good thermal stability, and high triplet energy level

Active Publication Date: 2013-08-07
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The research on organic electroluminescent materials first began in the 1960s, but it has not been paid attention to by people.

Method used

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  • Electroluminescent material and application thereof
  • Electroluminescent material and application thereof
  • Electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Synthesis of 1,3-bis[3-(9-diphenyltriazine)carbazole]benzene (compound 2, DTCZP)

[0060]

[0061] Step 1: Mix 3-bromocarbazole (12.3g, 0.05mol), 3,5-diphenyliodotriazine (21.54g, 0.06mol), potassium tert-butoxide (11.2g, 0.1mol), Toluene (150g) was added to the three-neck flask in turn, nitrogen gas was passed through the reaction flask for 30 minutes, then cuprous iodide (1.9g, 0.01mol) and o-phenanthroline (0.9g, 0.005mol) were added, and the reaction was refluxed for 8h to stop the reaction. After cooling down to room temperature, filter the filter cake with 200mL H 2 0. Rinse with 150mL o-xylene to obtain 17.88g of white solid, yield 75%. MS [m / z]: [M + ]=476.12,478.14.

[0062] Step 2: Mix 3-bromo-9-(3,5-diphenyltriazine)carbazole (9.54g, 0.02mol), m-diphenylboronic acid (1.66g, 0.01mol), potassium carbonate (4.14g, 0.03 mol), DMF (100mL) were added to the three-necked flask in turn, and Pd (PPh 3 ) 4 (0.23g, 0.2mmol), heated to reflux for 12h,...

Embodiment 2

[0063] Example 2: Synthesis of 1,4-bis{4-[5-(3,5-diphenyltriazine)benzofuran]}benzene (compound 19, DTBFuP)

[0064]

[0065] Step 1: Mix 4-benzofuranboronic acid (2.55g, 0.012mol), 3,5-diphenyliodotriazine (3.59g, 0.01mol), potassium tert-butoxide (2.24g, 0.02mol), o Pd(PPh 3 ) 4 (0.12g, 0.1mmol), reflux reaction for 6h, TLC showed that the reaction of raw materials was complete, and the reaction was stopped. Suction filtration, the filtrate is spin-dried and column chromatography obtains light yellow solid 3.39g, yield 85%, MS [m / z]: [M + ]=399.28.

[0066] Step 2: Add TBFu (2.39g, 6mmol) and THF (30g) into a three-necked flask, blow nitrogen gas to cool down to -78°C, add n-butyl lithium in n-hexane solution (3.27mL, 7.2mmol) dropwise, and add dropwise over 10 minutes Finished; keep at -78°C for 30 minutes, then raise the temperature to -30°C for 2 hours; then cool down to -78°C and add trimethyl borate (1.25g, 12mmol) dropwise, and add dropwise for 5 minutes; warm u...

Embodiment 3

[0068] Example 3: Synthesis of DTCZQu (Compound 56)

[0069]

[0070] Step 1: Add 4-bromo-2-iodonitrobenzene (32.8g, 0.1mol), 1-naphthaleneboronic acid (18.92g, 0.11mol), toluene (200g), methanol (200g) into the three-necked flask in sequence, and then Potassium carbonate (27.6g, 0.2mol) was added to the reaction flask as a 2M aqueous solution. Add Pd(PPh 3 ) 4 (1.2g, 1mmol), reflux reaction for 6h, TLC showed that the reaction of raw materials was complete, and the reaction was stopped. Add 100g of ethyl acetate to the reaction system, extract and separate, wash the organic phase with 100g of water and 100g of saturated brine respectively, dry with anhydrous sodium sulfate and spin dry, obtain 20.3g of light yellow solid by column chromatography, yield 62%, MS [m / z]: [M + ]=327.07.

[0071] Step 2: Add DTCZQu-A (19.68g, 0.06mol) and o-dichlorobenzene (200g) into a three-neck flask, blow nitrogen gas to raise the temperature to reflux, keep the reaction for 24h, cool d...

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Abstract

The invention relates to an electroluminescent material. According to the invention, diphenyl triazine is adopted as a ligand, and is subjected to a substitution reaction with aromatic heterlcyclic ring, such that a compound comprising two heterlcyclic rings is obtained. The aromatic heterlcyclic ring is carbazole, benzocarbazole, dibenzothiophene or dibenzofuran. The two heterlcyclic ring compounds are directly connected or connected through aromatic groups. According to the invention, the diphenyl triazine material has high triplet-state energy level and good thermal stability. Also, the carbazole, benzocarbazole, dibenzothiophene or dibenzofuran structure generally has high triplet-state energy level. The two are connected, and a dimeric structure is further prepared through other groups. When the novel structure is adopted as a phosphorescent main material and is used in an electroluminescent material, good photoelectric property is provided. The material can be used as an excellent blue phosphorescent main material.

Description

technical field [0001] The invention relates to an electroluminescent material and its application, in particular to a diphenyltriazine-substituted biheterocyclic compound electroluminescent material and its application in organic light emitting diodes. Background technique [0002] As a new generation of display technology, organic electroluminescent materials (OLED) have the following characteristics: a wide range of material selection, which can realize any color display from red to blue; low driving voltage, only 3-12V DC voltage; luminous brightness and luminous High efficiency; wide luminous viewing angle, fast response speed; in addition, it has the advantages of being ultra-thin and can be made on a flexible panel. [0003] The research on organic electroluminescent materials first began in the 1960s, but has not been paid attention to by people. Until 1987, Tang et al. from Eastern Kodak Company invented a sandwich structure device, using an organic small molecule ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/14C07D487/04C07D405/14C07D409/14H01L51/54
Inventor 石宇任辉彩张鑫鑫吴同川张钊高志峰
Owner VALIANT CO LTD
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