Arylamine derivative and organic light-emitting device thereof

A technology of organic light-emitting devices and derivatives, which is applied in the direction of light-emitting materials, organic chemistry, and electric solid-state devices. Good film-forming effect

Inactive Publication Date: 2020-04-07
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, hole transport layer materials, electron transport layer materials, host materials, dopant materials, fluorescent luminescent materials and phosphorescent luminescent materials have been developed very maturely, but the development types of capping layer materials (Capping Layer) are relatively single, and the effect not ideal

Method used

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  • Arylamine derivative and organic light-emitting device thereof
  • Arylamine derivative and organic light-emitting device thereof
  • Arylamine derivative and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0122] The preparation and formation methods of each layer in the organic light-emitting device are not particularly limited, and vacuum evaporation method, spin coating method, vapor deposition method, blade coating method, laser thermal transfer method, electrospray coating method, and slit coating method can be used. Any one of the method and the dip coating method, the method of vacuum evaporation is preferably used in the present invention.

[0123] The organic light-emitting device of the present invention can be widely used in the fields of panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal lamp and the like.

Synthetic example 1

[0131] [Synthesis Example 1] Synthesis of Compound 1

[0132]

[0133] Synthesis of Intermediate 1-1

[0134] Under nitrogen protection, weigh 3-chloroiminodibenzyl (18.83g, 0.082mol), compound 2-(4-bromophenyl) benzoxazole (24.08g, 0.083mol), cuprous iodide (7.8 g, 0.041mol), ethylenediamine (2.8mL, 0.041mol) and cesium carbonate (80g, 0.246mol), and were added to toluene (250mL) in the above order, and stirred at reflux. Extraction with ethyl acetate, distillation under reduced pressure, dichloromethane and hexane to get intermediate 1-1 (28.78g, 83%). HPLC detection solid purity ≧99.3%.

[0135] Synthesis of Intermediate 1-2

[0136] Under nitrogen protection, toluene (600mL), 4-(2-benzoxazolyl)aniline (44.15g, 0.21mol), 1-bromobenzene (32.97g, 0.21mol), acetic acid Palladium (0.61 g, 0.0027 mol), sodium tert-butoxide (33.7 g, 0.351 mol) and tri-tert-butylphosphine (10.8 mL of a 1.0 M solution in toluene, 0.0108 mol). And react under the condition of reflux for 2 ho...

Synthetic example 2

[0142] [Synthesis Example 2] Synthesis of Compound 12

[0143]

[0144] The 4-bromophenylboronic acid in Synthesis Example 1 was replaced by equimolar e-12, and the other steps were the same to obtain compound 12 (36.33 g, yield about 84%), and the purity of the solid was detected by HPLC ≧99.0%.

[0145] Mass Spectrum m / z: 864.39 (calculated: 864.35). Theoretical element content (%)C 61 h 44 N 4 o 2 : C, 84.70; H, 5.13; N, 6.48; O, 3.70 The measured element content (%): C, 84.70; H, 5.14; N, 6.47; O, 3.70. 1 H NMR (600MHz, DMSO) (δ, ppm): 7.96(d,1H), 7.93(d,1H), 7.89–7.85(m,2H), 7.83–7.78(m,3H), 7.75(d,1H ),7.66–7.62(m,5H),7.60–7.56(m,2H),7.43(d,1H),7.40–7.33(m,7H),7.26(dd,1H),7.25–7.22(m,1H ),7.20(ddd,1H),7.15(dd,1H),7.13(d,1H),7.08(dd,2H),7.03-6.98(m,2H),6.96(dd,1H),6.81(td, 1H), 3.07(s, 4H), 1.67(d, 6H). The above results confirmed that the obtained product was the target product.

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Abstract

The invention relates to the technical field of organic photoelectric materials, and provides an arylamine derivative and an organic light-emitting device thereof. The arylamine derivative has a specific structure, so that the arylamine derivative has a relatively high glass transition temperature, good thermal stability and higher stability, and the prepared organic light-emitting device has theadvantage of long service life. Besides, the arylamine derivative is high in refractive index, can effectively solve the problem of total emission at the interface of an ITO film and a glass substrateand the interface of the glass substrate and the air, reduce total emission loss and waveguide loss in the OLED device, and improve light extraction efficiency, thereby improving light emitting efficiency of the organic light emitting device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an aromatic amine derivative and an organic light-emitting device thereof. Background technique [0002] OLED is called organic light-emitting diode or organic light-emitting display. As an emerging application technology in the display field, it has a series of advantages. OLED is light and thin, has unique foldable and bending characteristics, and can realize transparent display, which will greatly expand its application range. OLED is self-illuminating, with high contrast and bright colors. OLED is all solid state and has good shock resistance. OLEDs operate in a wide temperature range, as low as -40°C and as high as 80°C. OLEDs have a wide range of viewing angles, generally up to 160°. There are many OLED materials, a wide range of choices, and strong plasticity. OLED does not require an external backlight source and is more energy-efficient. OLED do...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D417/14C07D403/14C07D413/12C07D403/12C09K11/06H01L51/50H01L51/54
CPCC07D413/14C07D417/14C07D403/14C07D413/12C07D403/12C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H10K85/615H10K85/622H10K85/624H10K85/623H10K85/657H10K85/6576H10K85/6572H10K50/00
Inventor 赵倩刘喜庆韩春雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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