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Compound, display panel and electronic equipment

A compound and an independent technology, applied in the field of organic electroluminescent materials, can solve the problems of unfavorable large-scale production, efficiency roll-off, and low production cost, so as to improve luminous efficiency and working life, improve luminous efficiency, and increase the strength of the oscillator Effect

Active Publication Date: 2020-02-07
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triplet Excited State T of Phosphorescent Materials 1 Direct radiative decay to the ground state S 0 , due to the heavy atom effect, the intramolecular intersystem crossing can be enhanced through spin coupling, and 75% of the triplet excitons can be directly utilized, thus realizing the S 1 and T 1 Jointly participated in the emission, the theoretical maximum internal quantum yield can reach 100%; according to the Lambertian luminescence mode, the light extraction efficiency is about 20%, so the EQE of the OLED device based on the phosphorescent material can reach 20%; but the phosphorescent material is basically Ir , Pt, Os, Re, Ru and other heavy metal complexes, the production cost is high, which is not conducive to large-scale production; and at high current density, the phosphorescent material has a serious efficiency roll-off phenomenon, and the stability of the phosphorescent device is not good.
The two triplet excitons of the TTA material interact and recombine to generate a higher energy level singlet excited state molecule and a ground state molecule; but two triplet excitons produce a singlet state exciton, so the theoretical maximum internal quantum yield is only It can reach 62.5%; in order to prevent a large efficiency roll-off phenomenon, the concentration of triplet excitons needs to be regulated in this process
TADF materials are mainly organic compounds, do not require rare metal elements, have low production costs, can be chemically modified by various methods, and have great application prospects, but currently there are few types of TADF materials disclosed, and their performance cannot reach that of OLED devices. Requirements

Method used

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  • Compound, display panel and electronic equipment
  • Compound, display panel and electronic equipment
  • Compound, display panel and electronic equipment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160] This embodiment provides a compound with the following structure:

[0161]

[0162] Its preparation method comprises the following steps:

[0163]

[0164] Under nitrogen protection, compound S1 (1.5mmol), S2 (3.2mmol), [Pd 2 (dba) 3 ]·CHCl 3 (0.05mmol) and HP(tBu) 3 ·BF 4 (0.1mmol) was added into a 100mL two-necked flask, and 30mL of toluene was injected into the two-necked flask (through N 2 15min deoxygenation), and then add 2.5mL concentration of 1M K 2 CO 3 Aqueous solution (pass N in advance 2 15min deoxygenation), stirring overnight at room temperature; after the reaction, add 20mL deionized water, and then drop a few drops of 2M HCl; extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography, and finally the intermediate product ...

Embodiment 2

[0171] This embodiment provides a compound with the following structure:

[0172]

[0173] Its preparation method comprises the following steps:

[0174]

[0175] Under the condition of -78°C, S1 (1.8mmol) was dissolved in ether (100mL), and n-BuLi (3.9mmol) n-hexane solution was added dropwise into the solution; the reaction solution was continuously stirred for 2h, and slowly heated to room temperature, stirred at room temperature for 1 h. The reaction solution was cooled to -78°C again, and 90 mL of S5 (3.8 mmol) in toluene was added dropwise with stirring; the temperature was slowly raised to room temperature and stirred overnight. All the solvent was distilled off under reduced pressure, and the crude product was collected. The crude product was washed with methanol (3 x 40 mL) and pentane (3 x 40 mL), respectively, and the crude product was collected again. The crude product was purified by silica gel chromatography, using a mixed solvent of n-hexane and chlorof...

Embodiment 3

[0182] This embodiment provides a compound with the following structure:

[0183]

[0184] Its preparation method comprises the following steps:

[0185]

[0186] Under nitrogen protection, compound S1 (2.25mmol), S7 (4.8mmol), [Pd 2(dba) 3 ]·CHCl 3 (0.1mmol) and HP(tBu) 3 ·BF 4 (0.2mmol) was added into a 250mL two-necked flask; 60mL of toluene was injected into the two-necked flask (passed N in advance 2 15min deoxygenation), and then added dropwise 4mL concentration of 1M K 2 CO 3 Aqueous solution (pass N in advance 2 15min deoxygenation), stirred overnight at room temperature; after the reaction, add 35mL deionized water, and then drop a few drops of 2M HCl; extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography, and finally the interme...

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Abstract

The invention provides a compound, a display panel comprising the compound and electronic equipment. The compound is provided with a structure shown in the formula I, wherein X<1> and X<2> are respectively selected from O, S and N, D<1> and D<2> refer to electron-donating groups, and A<1> and A<2> refer to electron-accepting groups. The display panel comprises an OLED device, wherein the OLED device comprises an anode, a cathode and at least one organic thin film layer located between the anode and the cathode; each organic thin film layer comprises a luminous layer; each luminous layer comprises the compound; and the compound is used as a main material or a doped material or a co-doped material. According to the compound, through molecular structure design, delta(EST) is lowered, an efficient reverse intersystem crossing process is realized, and the compound has typical TADF characteristics; and when the compound is used as a luminous layer material of the OLED device, the luminous efficiency of the OLED device can be improved, and the working life of the OLED device can be prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a compound, a display panel and electronic equipment including the compound. Background technique [0002] Organic electroluminescent technology is an emerging technology with broad application prospects in the field of optoelectronics. Compared with traditional inorganic electroluminescent devices, organic electroluminescent devices (Organic Light Emitting Diode, OLED) have ultra-thin, self-luminous, and wide viewing angle. , fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, etc., have been widely used in industries such as flat panel display, flexible display, solid state lighting and vehicle display. At present, OLED has entered the stage of industrialization, and the development of high-performance organic photoelectric materials is still the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07F5/02C07D519/00C07F9/6561C07F9/6571C07F9/6578C07F9/6596C07D493/04C07D495/04H01L51/50H01L51/54H01L27/32H10K99/00
CPCC07D487/04C07F5/027C07D519/00C07F9/6561C07F9/657163C07F9/6578C07F9/6596C07D493/04C07D495/04H10K59/10H10K85/626H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K50/12H10K85/658C07F9/5329H10K50/11H10K2101/20C07F5/02H10K85/322H10K85/631H10K50/15H10K50/18H10K50/171
Inventor 高威代文朋张磊肖文静牛晶华林沙
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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