Phenanthrene quinoxaline fluorescent compound and preparation method and application thereof, and electroluminescent device

A technology for electroluminescent devices and fluorescent compounds, which is applied in the fields of electro-solid devices, chemical instruments and methods, electrical components, etc., can solve the problems of red shift of the emission spectrum of fluorescent devices, low hole and electron transfer rate, etc. Efficiency, redshift reduction, and stability enhancement effects

Active Publication Date: 2014-01-29
TCL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

from figure 1 It can be found that the groups such as anthracene, naphthalene, phenanthrene, pyrene, and triacene used in blue-light fluorescent materials are all composed of carbon and hydrogen elements, and their hole and electron transport rates are relatively low, which needs to be further improved.
In addition, all groups except triacene have relatively good planarity. When its derivatives are applied to the light-emitting layer of fluorescent devices, they are easy to form π-π stacking, which causes red shift of the emission spectrum of fluorescent devices.

Method used

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  • Phenanthrene quinoxaline fluorescent compound and preparation method and application thereof, and electroluminescent device
  • Phenanthrene quinoxaline fluorescent compound and preparation method and application thereof, and electroluminescent device
  • Phenanthrene quinoxaline fluorescent compound and preparation method and application thereof, and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] When Ar = , the phenanthroxaline fluorescent compound is 3,6,10,13-tetraphenylphenanthroxaline (abbreviated as TPhPhZN), and its molecular structure is as follows: Figure 6 shown.

[0045] Its preparation method comprises the following steps:

[0046] a. Dissolve 3,6-dibromo-o-phenylenediamine (10.0 mmol), 3,6-dibromo-9,10-phenanthrenequinone (10.0 mmol) and sodium hydroxide (25.0 mmol) in absolute ethanol (50.0 ml), heated to 100°C and refluxed for 4 hours, a yellow solid precipitated out slowly, after the reaction was complete, cooled to room temperature, and filtered directly, the obtained yellow solid 3,6,10,13-tetrabromophenanthroxaline, Drying, directly used in the next reaction, yield: 95%. MS (APCI): theoretical value C 20 h 8 Br 4 N 2 : 591.7, experimental value, 593.2 (M+1) + .

[0047] b. Dissolve the solid 3,6,10,13-tetrabromophenanthroxaline (5.0 mmol) and phenylboronic acid (25.0 mmol) obtained above in toluene solution, and add potassium carbon...

Embodiment 2

[0049] When Ar = , the phenanthroxaline fluorescent compound is 3,6,10,13-tetrakis(1-naphthyl)phenanthroxaline (abbreviated as 1-TNaPhZN), and its molecular structure is as follows: Figure 7 shown.

[0050] Its preparation method comprises the following steps:

[0051] a. Dissolve 3,6-dibromo-o-phenylenediamine (10.0 mmol), 3,6-dibromo-9,10-phenanthrenequinone (10.0 mmol) and sodium hydroxide (25.0 mmol) in absolute ethanol (50.0 ml), heated to 100°C and refluxed for 4 hours, a yellow solid precipitated out slowly, after the reaction was complete, cooled to room temperature, and filtered directly, the obtained yellow solid 3,6,10,13-tetrabromophenanthroxaline, Drying, directly used in the next reaction, yield: 95%. MS (APCI): theoretical value C 20 h 8 Br 4 N 2 : 591.7, experimental value, 593.2 (M+1) + .

[0052] b. The solid 3,6,10,13-tetrabromophenanthroxaline (5.0 mmol) obtained above, 1- Naphthaleneboronic acid (25.0 mmol) was dissolved in toluene solution, po...

Embodiment 3

[0054] When Ar = , the phenanthroxaline fluorescent compound is 3,6,10,13-tetrakis(2-naphthyl)phenanthroxaline (abbreviated as 2-TNaPhZN), and its molecular structure is as follows: Figure 8 shown.

[0055] Its preparation method comprises the following steps:

[0056] a. Dissolve 3,6-dibromo-o-phenylenediamine (10.0 mmol), 3,6-dibromo-9,10-phenanthrenequinone (10.0 mmol) and sodium hydroxide (25.0 mmol) in absolute ethanol (50.0 ml), heated to 100°C and refluxed for 4 hours, a yellow solid precipitated out slowly, after the reaction was complete, cooled to room temperature, and filtered directly, the obtained yellow solid 3,6,10,13-tetrabromophenanthroxaline, Drying, directly used in the next reaction, yield: 95%. MS (APCI): theoretical value C 20 h 8 Br 4 N 2 : 591.7, experimental value, 593.2 (M+1) + .

[0057] b. The solid 3,6,10,13-tetrabromophenanthroxaline (5.0 mmol) obtained above, 2- Naphthaleneboronic acid (25.0 mmol) was dissolved in toluene solution, po...

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Abstract

The invention discloses a phenanthrene quinoxaline fluorescent compound and a preparation method and an application thereof, and an electroluminescent device. The molecular structural formula of the phenanthrene quinoxaline fluorescent compound is represented in the drawing. The structural formula of Ar is as the following. According to the invention, with a phenanthrene quinoxaline special electron transmission property, the compound is connected with a blue light luminescent group with high quantum efficiency, such that a more twisted molecular structure is realized, and pi-pi stacking among molecules is reduced. Also, luminescent layer cavity and electron transmission speeds are balanced, and the luminescent efficiency of the device is further improved. Therefore, device stability can be improved, and the device is provided with excellent electroluminescent performance. A high-efficiency full-color display can be developed. The compound can be widely applied in OLED large-screen display and OLED white lighting with high brightness requirement.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a phenanthroxaline fluorescent compound, a preparation method and application thereof, and an electroluminescence device. Background technique [0002] After more than 20 years of development of organic light-emitting diodes (OLED), more and more organic light-emitting materials have been developed, and some groups that were first used in blue-light fluorescent light-emitting materials have also been further improved, such as anthracene, naphthalene, phenanthrene , pyrene and triacene (structural formula such as figure 1 ) and so on have a relatively wide energy band width, which can well meet the requirements of blue-light fluorescent light-emitting materials. from figure 1 It can be found that groups such as anthracene, naphthalene, phenanthrene, pyrene, and triacene used in blue-light fluorescent materials are all composed of carbon and hydrogen elements, and their hole ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/38C09K11/06H01L51/54
CPCY02B20/181C09K11/06C07D241/38C09K2211/1044H10K85/615H10K85/6572Y02B20/00
Inventor 黄宏
Owner TCL CORPORATION
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