Quinazoline derivative and application thereof in organic electroluminescent device

A technology of electroluminescent devices and derivatives, which is applied in the field of white light lighting, can solve the problems of preparation process limitations and limited applications, and achieve the effect of good spectral stability

Inactive Publication Date: 2013-08-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the research on smart light-emitting materials has become a hot topic in the past decade, its application in the field of organic electroluminescence is very limited due to the limitation of preparation process.

Method used

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  • Quinazoline derivative and application thereof in organic electroluminescent device
  • Quinazoline derivative and application thereof in organic electroluminescent device
  • Quinazoline derivative and application thereof in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: the synthesis of intermediate

[0017] In a 500 mL three-necked flask, add 100 mL (100 mmol) of a 1 M tetrahydrofuran solution of phenylmagnesium bromide, add 100 mL of dry diethyl ether, and heat to reflux in an oil bath at 45°C. A solution of 5.91 g (50 mmol) of 2-cyanoaniline in 50 mL of dry ether was added dropwise thereto over 30 minutes. After further reflux for 1.5 hours, it was cooled to 0°C in an ice-water bath. Then, a solution of 13.2 g (60 mmol) of 4-bromobenzoyl chloride in 100 mL of dry ether was added dropwise, and heated to reflux in an oil bath at 45° C. for 2 hours. After the reaction was completed, the mixture was cooled to 0° C. in an ice-water bath, and saturated aqueous ammonium chloride solution was added. The precipitate was taken out by filtration, washed with a small amount of methanol, and then vacuum-dried to obtain 7.59 g of an intermediate (yield 42%).

Embodiment 2

[0018] Embodiment 2: the synthesis of compound (1) and (2)

[0019] Under nitrogen conditions, add palladium acetate 25mg and tri-tert-butylphosphine 0.1 mL, heated to reflux for 4 hours. After stopping the reaction, the solvent was removed, and the residual substance was separated on a silica gel column with dichloromethane as the eluent to obtain compound (1). 1H NMR (300MHz; CDCl 3 ):δ8.93(d,J=8.4Hz,2H),8.27(d,J=8.7Hz,1H),8.18(m,3H),7.91–7.98(m,3H),7.74–7.78(m, 2H),7.59–7.66(m,4H),7.54(d,J=8.4Hz,2H),7.41–7.47(m,2H),7.28–7.34(m,2H).

[0020] The synthesis of compound (2) is the same as that of compound (1), just replace carbazole with diphenylamine. 1H NMR (300MHz; CDCl 3 ):δ8.54(d,J=7.8Hz,2H),8.12(d,J=8.7Hz,2H),7.85–7.89(m,3H),7.57–7.60(m,3H),7.50–7.55( m,1H),7.25-7.31(m,4H),7.18(d,J=8.7Hz,6H),7.05–7.10(m,2H).

Embodiment 3

[0021] Example 3: Light-emitting device [ITO / NPB / TCTA / (1) / TPBI / LiF / Al]

[0022] On the glass substrate coated with ITO anode, the hole transport layer NPB (40nm), the electron blocking layer TCTA (5nm), the compound (1) is the light emitting layer (15nm), the electron transport layer TPBI (45nm), and the electron injection Layer LiF (1nm), Al cathode (100nm). Maintain a pressure of 5×10 during the evaporation process -6 Pa. The fabricated device has a turn-on voltage of 3.2V and a maximum brightness of 1945cd m -2 , the maximum current efficiency is 0.93cd A -1 , the maximum energy efficiency is 0.88lm W -1 , the luminous peak is at 445nm, which is blue light emission.

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Abstract

The invention relates to a quinazoline derivative and an application thereof in an organic electroluminescent device, belonging to the technical field of white light illumination in organic electroluminescence. By adopting the quinazoline derivative, a white light organic electroluminescent device with better CIE coordinates and better spectrum stability can be obtained by carrying out doping evaporation on the quinazoline derivative and solid acid namely camphorsulfonic acid (CSA) with strong acidity and high stability under a high-vacuum-degree condition. Although the data performance of the current device is not ideal enough, the preparation method and process are first cases, and a new idea for synthesizing a white light material and preparing devices in the future is provided.

Description

technical field [0001] The invention belongs to the technical field of white light illumination in organic electroluminescence, and specifically relates to two kinds of quinazoline derivatives with simple structures and the application of these two materials in organic electroluminescence devices. Background technique [0002] Organic light-emitting solids have attracted increasing attention in the field of organic electroluminescence (OLED) due to their potential applications in solid-state lighting and flat-panel displays (see C.W. Tang, S.A. Vanslyke, Appl. Phys. Lett. 1987, 51,913), and the performance of white lighting is even more striking. So far, there have been many methods and means to realize white light emission of organic electroluminescence. These include mixing and doping different light-emitting guests into the same light-emitting layer (see B.W.D'Andrade, R.J.Holmes, S.R.Forrest, Adv. Mater. 2004, 16, 624.), and introducing different light-emitting material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D239/74C09K11/06H01L51/54
CPCY02B20/181Y02B20/00
Inventor 张红雨王悦
Owner JILIN UNIV
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