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Dibenzothiophene derivative and organic light-emitting device thereof

An organic light-emitting device, dibenzothiophene technology, applied in the direction of light-emitting materials, organic chemistry, electric solid devices, etc., can solve the problems of the light-emitting layer cannot be effectively combined, the uniformity of the film is destroyed, and the hole and electron injection is unbalanced. , to achieve the effect of reducing the quenching phenomenon of aggregated state fluorescence, enhancing the electron donating ability, and making the synthesis simple and easy to operate.

Active Publication Date: 2020-11-03
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Crystallization will destroy the uniformity of the film, and at the same time destroy the good interfacial contact between the hole transport layer, the anode and the organic layer, resulting in a decrease in the efficiency and life of the device.
And the mobility of the holes is too low, which will make the injection of holes and electrons unbalanced, and the two cannot be effectively combined in the light-emitting layer, resulting in a decrease in the luminous efficiency of the organic light-emitting device.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0112] 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, slit coating method can be used. Either of the cloth method and the dip coating method, the method of vacuum vapor deposition is preferably used in the present invention.

[0113] 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.

Embodiment 1

[0121] [Example 1] Synthesis of Compound 1

[0122]

[0123] Step1: Synthesis of intermediate A-1

[0124] Under nitrogen protection, toluene (600mL), a-1 (benzidine) (35.54g, 0.21mol), b-1 (67.46g, 0.21mol), palladium acetate (0.61g, 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 hours. After the reaction stopped, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, recrystallized with methanol, filtered with suction and rinsed with methanol to obtain a recrystallized solid to obtain intermediate A-1 (67.08g, the yield was about 78 %), HPLC detection solid purity >= 98.4%.

[0125] Step2: Synthesis of intermediate B-1

[0126] Under nitrogen protection, toluene solvent (600ml), c-1 (42.03g, 108mmol), intermediate A-1 (49.14g, 120mmol), Pd 2 (dba) 3 (3.98g, 4.35mol), BINAP (2.02g,...

Embodiment 2

[0132] [Example 2] Synthesis of compound 2

[0133]

[0134] Replace a-1 (benzidine) in Step 1 of Synthesis Example 1 with equimolar a-2, and the other steps were the same to obtain compound 2 (20.90 g, the yield of Step 4 was about 79%), and the solid purity was detected by HPLC > 99.4%.

[0135] Mass Spectrum m / z: 755.29 (Theoretical: 755.26). Theoretical element content (%)C 56 h 37 NS: C, 88.97; H, 4.93; N, 1.85; S, 4.24 Measured element content (%): C, 88.98; H, 4.92; N, 1.84; S, 4.25. 1 H NMR (600MHz, CDCl 3)(δ,ppm):8.15(d,1H),8.09–8.02(m,2H),7.99–7.92(m,3H),7.91–7.83(m,4H),7.80(dt,3H),7.78– 7.64 (m, 5H), 7.56 (td, 3H), 7.51–7.40 (m, 6H), 7.34–7.21 (m, 5H), 7.12 (dd, 2H), 7.04–7.02 (m, 3H). 1 H NMR details are attached figure 2 shown. The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides a dibenzothiophene derivative and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. According to the invention, dibenzothienyl biphenyl fluorenyl is used as a substituent group to be connected with a triarylamine structure, so that the electron donating capability of the compound is further enhanced, and the compound has good hole transport performance and is a good hole transport material. The dibenzothiophene derivative provided by the invention has a special rigid condensed ring structure, can relatively limit the movement of the whole group, significantly reduces the aggregation-state fluorescence quenching phenomenon of the material and improves the stability. In addition, the derivative has good film-forming property and is simple to synthesize and easy to operate, and can be widely applied to the fields of panel display, illumination light sources, organic solar cells, organic photoreceptors ororganic thin film transistors and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a dibenzothiophene 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 the following characteristics: the material uses organic matter / polymer, so the material selection range is wide, and any color from red light to blue light can be realized Compared with field emission displays, plasma display devices, and flat-panel displays such as liquid crystal displays, it has the characteristics of low driving voltage, only 3V to 12V DC voltage; high luminous brightness and luminous efficiency; wide luminous viewing angle, responsive Fast speed; ultra-thin, light weight, fully cured active light-emitting; can be made on a flexible substrate, the device can be bent; wide operating temper...

Claims

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Application Information

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IPC IPC(8): C07D333/76C07D409/12C07D413/12C09K11/06H01L51/54
CPCC07D333/76C07D409/12C07D413/12C09K11/06C09K2211/1092C09K2211/1033C09K2211/1029C09K2211/1007C09K2211/1011H10K85/615H10K85/657H10K85/6574H10K85/6576H10K85/6572Y02E10/549
Inventor 韩春雪周雯庭孙月
Owner CHANGCHUN HYPERIONS TECH CO LTD
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