Aromatic compound and organic light-emitting diode containing aromatic compound

A technology of aromatic compounds and light-emitting diodes, which is applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of slow development of luminous efficiency and luminous life of blue luminescent materials, and achieve the improvement of external quantum efficiency and high quantum efficiency. Efficiency, the effect of excellent thermal stability

Active Publication Date: 2017-08-29
郑建鸿
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with red luminescent materials and green luminescent materials, the development of blue luminescent materials in terms of luminous efficiency and luminous lifetime is relatively slow, so the development of novel blue luminescent materials with high luminous efficiency and long life is currently extremely Goals to work on

Method used

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  • Aromatic compound and organic light-emitting diode containing aromatic compound
  • Aromatic compound and organic light-emitting diode containing aromatic compound
  • Aromatic compound and organic light-emitting diode containing aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0087] Synthesis Example 1: Synthesis of Intermediate I-1

[0088] [Reaction scheme 1]

[0089]

[0090] 4-(diphenylamino)benzaldehyde (4-(diphenylamino)benzaldehyde) (2.73g, 10.0mmol) and 4-bromobenzyl phosphate diethyl (diethyl(4-bromobenzyl)phosphonate) (3.53g, 11.5mmol) was placed in a double-necked flask, vacuumized and fed with nitrogen, and then 20mL of anhydrous tetrahydrofuran (THF) was added; under ice-cooling, potassium tert-butoxide (t-BuOK) dissolved in THF (30mL) ) (3.36g, 30mmole) was slowly added and mixed, and reacted at 0°C for 15 minutes. The solvent was removed by concentration under reduced pressure, and then purified by column chromatography (n-hexane:dichloromethane=9:1) to obtain a yellow intermediate product I-1 ((E)-4-(4-bromostyryl)- N,N-diphenylaniline) (3.71 g, 87% yield).

[0091] 1 H NMR (400MHz, CDCl3, δ): 7.45 (d, J = 8.4Hz, 2H), 7.36 (d, J = 8.8Hz, 2H), 7.34 (d, J = 8.8Hz, 2H), 7.28-7.24 ( m, 4H), 7.11(d, J=7.6Hz, 4H), 7.05-7.01(m, 5H)...

Synthetic example 2

[0094] Synthesis example 2: the synthesis of intermediate product 1-2

[0095] [Reaction scheme 2]

[0096]

[0097] 4-(bis(4-fluorophenyl)amine)benzaldehyde (4-(bis(4-fluorophenyl)amino)benzaldehyde) (4.64g, 15mmol) and 4-bromobenzyl phosphate diethyl (diethyl(4 -bromobenzyl)phosphonate) (5.07g, 16.5mmol) was placed in a two-necked flask, vacuumized and nitrogen was introduced, and 20mL of anhydrous tetrahydrofuran (THF) was added; Potassium tert-butoxide (t-BuOK) (5.0 g, 45 mmol) was slowly added and mixed, and reacted at 0° C. for 15 minutes. The solvent was removed by concentration under reduced pressure, and then purified by column chromatography (n-hexane:dichloromethane=9:1) to obtain a yellow intermediate product I-2 ((E)-4-(4-bromostyryl)- N,N-bis(4-fluorophenyl)aniline) (6.17 g, 89% yield).

[0098] 1 H NMR (400MHz, CDCl 3 ,δ):7.44(d,J=8.4Hz,2H),7.33(d,J=8.8Hz,2H),7.32(d,J=8.8Hz,2H),7.06-6.92(m,11H),6.88 (d,J=16Hz,1H).

[0099] 13 C NMR (100MHz, CDCl 3 ,δ...

Synthetic example 3

[0101] Synthesis example 3: the synthesis of intermediate product 1-3

[0102] [Reaction scheme 3]

[0103]

[0104] 4-(1-naphthalenyl(phenyl)amine)carbaldehyde (4-(naphthalen-1-yl(phenyl)amino)benzaldehyde) (2.87g, 8.9mmol l) and 4-bromobenzyl diethyl phosphate (diethyl(4-bromobenzyl)phosphonate)(3.0g, 9.76mmol) was placed in a two-necked flask, vacuumized and fed with nitrogen, and then 20mL of anhydrous tetrahydrofuran (THF) was added; Potassium tert-butoxide (t-BuOK) (2.24 g, 20 mmol) in THF (30 mL) was slowly added and mixed, and reacted at 0° C. for 15 minutes. The solvent was removed by concentration under reduced pressure, and then purified by column chromatography (n-hexane:dichloromethane=9:1) to obtain a yellow intermediate product I-3 ((E)-N-(4-(4- bromostyryl)phenyl)-N-phenylnaphthalen-1-amine) (2.67 g, 63% yield).

[0105] 1 H NMR (400MHz, CDCl 3 ,δ):7.91-7.86(m,2H),7.77(d,J=8.0Hz,1H),7.48-7.29(m,10H),7.22-6.94(m,8H),6.85(d,J=16Hz ,1H).

[0106] 13 C N...

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Abstract

Disclosed are an aromatic compound shown in the chemical formula 1 and an organic light-emitting diode containing the aromatic compound. In the chemical formula 1, A, Ar2, R1, R2 and m are same as that in the embodiment. The aromatic compound has characteristics of blue luminescence, high quantum efficiency, and excellent thermal stability. Moreover, the aromatic compound can be applied to a luminescent layer or hole transport layer of an organic light emitting diode, can improve the external quantum efficiency, the maximum brightness, current efficiency and power efficiency of the organic light emitting diode, and prolongs the service life of the organic light emitting diode.

Description

technical field [0001] The present invention relates to a compound and an organic light emitting diode comprising it, in particular to an aromatic compound and an organic light emitting diode comprising it. Background technique [0002] Organic light-emitting diode (OLED) flat-panel displays have advantages such as wider viewing angles, faster response time, and thinner volume than liquid crystal displays, and are currently being used in large-area, high-brightness, and full-color displays. [0003] In order to develop a full-color flat-panel display, developing stable and high-efficiency light-emitting materials (red, green, blue) is the main goal of current OLED research. However, compared with red luminescent materials and green luminescent materials, the development of blue luminescent materials in terms of luminous efficiency and luminous lifetime is relatively slow, so the development of novel blue luminescent materials with high luminous efficiency and long life is cu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C211/56C07C211/58C07D209/86C07D209/88C07D403/10C09K11/06H01L51/54
CPCC09K11/06C07C211/54C07C211/56C07C211/58C07D209/86C07D209/88C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1059H10K85/633H10K85/631H10K85/654H10K85/6572H10K50/11
Inventor 郑建鸿陈奕翔吴奕靓
Owner 郑建鸿
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