Aryl pyridine ring-contained carbazole compounds and application thereof

A technology of compound and pyridine ring, which is applied in the field of new compounds, can solve the problems of large differences in luminous efficiency and achieve high electron and hole mobility and good thermal stability.

Active Publication Date: 2012-03-14
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is worth noting that most host materials still use FIrpic as a dye to realize blue phosphorescent devices, and the luminous efficiency of FIrpic blue phosphorescent devices with different host materials varies greatly.

Method used

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  • Aryl pyridine ring-contained carbazole compounds and application thereof
  • Aryl pyridine ring-contained carbazole compounds and application thereof
  • Aryl pyridine ring-contained carbazole compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The synthesis of embodiment 1 intermediate

[0065] (1) Synthesis of M101

[0066]

[0067] 25.85g 2,6-dibromopyridine, 13.20g phenylboronic acid and 0.55g Pd(PPh 3 ) 4 Dissolve in a mixture of 330mL toluene and 220mL ethanol, dissolve 24.2g potassium carbonate in 110mL water and add to the above reaction solution, stir and react at 70°C for 1.5h, then add 2.75g phenylboronic acid, react for another 0.5h, monitor by TLC end point of the reaction. After the reaction was completed, the organic phase was separated, washed three times with water and washed with anhydrous Na 2 SO 4 Carry out column chromatography after drying, eluent is sherwood oil: methylene chloride=20: 1 (V 1 / V 2 ), to obtain 15.60 g of white solid. MS (m / e): 234, yield 61.0%.

[0068] (2) Synthesis of M102

[0069]

[0070] 33.84g of 2-iodo-5-bromopyridine, 15.95g of phenylboronic acid and 0.55g of Pd(PPh 3 ) 4 Dissolve in a mixture of 330mL toluene and 220mL ethanol, dissolve 24.2g po...

Embodiment 2

[0138] The synthesis of embodiment 2 target product 1-1

[0139]

[0140] 47.9g M116, 55.3g 3-pyridineboronic acid and 1.15g Pd(PPh 3 ) 4 Dissolve in a mixture of 500mL toluene and 220mL ethanol, dissolve 24.2g potassium carbonate in 110mL water and add to the above reaction solution, stir and react at 70°C for 3h, and monitor the end point of the reaction by TLC. After the reaction was completed, the organic phase was separated, washed three times with water and washed with anhydrous Na 2 SO 4 Carry out column chromatography after drying, eluent is sherwood oil: methylene chloride=20: 1 (V 1 / V 2), to obtain 37.92g of white solid. MS (m / e): 474, yield 80.0%. Elemental analysis (C 33 h 22 N 4 ): theoretical value C: 83.52%, H: 4.67%, N: 11.81%; measured value C: 83.61%, H: 4.68%, N: 11.71%.

Embodiment 3

[0141] The synthesis of embodiment 3 target product 1-2

[0142] Using M116 and 2-pyridineboronic acid as raw materials, compound 1-2 was obtained through the same reaction as in Example 2. MS (m / e): 474, elemental analysis (C 33 h 22 N 4 ): theoretical value, C: 83.52%, H: 4.67%, N: 11.81%; measured value C: 83.62%, H: 4.69%, N: 11.69%.

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PUM

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Abstract

The invention relates to a compound with a general formula represented by formula (1). In the formula (1), Ar1, Ar2 and Ar3 are substituent groups, at least two groups of the substituent groups are pyridine ring-contained C5-60 aromatic groups, the residual groups is respectively and independently selected from hydrogen, a C1-C40 alkyl group, a C5-50 aromatic group, a nitrogen-contained C5-50 heterocyclic ring, and n is 1 or 2. The invention also relates to a purpose of the compounds in organic electroluminescent devices, especially electrophosphorescent devices as a matrix material of phosphorescent adulterants in the electrophosphorescent devices.

Description

technical field [0001] The invention relates to a novel compound and its application in the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescence (hereinafter referred to as OLED) and corresponding research began as early as the 1960s. In 1963, p.pope and others first discovered the electroluminescence phenomenon of organic single crystal anthracene, but due to the limitation of technical conditions, its driving voltage was as high as 400V, which failed to attract widespread attention. In 1987, C.W.Tang et al. of Kodak Corporation of the United States made an amorphous film device by vapor-depositing Alq3 and HTM-2, which reduced the driving voltage to less than 20V, and OLED attracted the attention of the world (US4356429). Due to the advantages of high brightness, wide viewing angle, fast photoelectric response, low voltage, low power consumption, rich colors, high contrast, light and thin structure, and simple p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K11/06H01L51/54
Inventor 邱勇李银奎黄雨鹏乔娟段炼
Owner TSINGHUA UNIV
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