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A boron-containing compound, display panel and display device

A boron compound and display panel technology, applied in the fields of compounds containing group 3/13 elements of the periodic table, organic chemistry, chemical instruments and methods, etc., can solve the problem that the quantum yield can only reach 62.5%, and the stability of phosphorescent devices is not stable Good, phosphorescent material efficiency roll-off and other issues, to achieve the effect of low cost, reduce overlap, and improve luminous efficiency

Active Publication Date: 2022-04-01
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, phosphorescent materials are basically heavy metal complexes such as Ir, Pt, Os, Re, Ru, etc., and the production cost is high, which is not conducive to large-scale production.
At high current density, there is a serious efficiency roll-off phenomenon in phosphorescent materials, and the stability of phosphorescent devices is not good
[0013] Triplet-triplet annihilation (TTA) materials: two adjacent triplet excitons, recombine to generate a higher-energy singlet excited state molecule and a ground state molecule, but two triplet excitons produce a singlet exciton , so the theoretical maximum internal quantum yield can only reach 62.5%
However, few TADF materials have been discovered so far, and new TADF materials that can be used in OLED devices need to be developed urgently.

Method used

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  • A boron-containing compound, display panel and display device
  • A boron-containing compound, display panel and display device
  • A boron-containing compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073]

[0074] Add 6.84g (20mmol) of the compound dibromoimine-2-bromophenyl, 100ml THF and 1.2g magnesium strips sequentially into a 250ml three-necked flask, replace with nitrogen, heat to 50°C and stir for 30min. Dissolve 4.38g (20mmol) of the compound dimethyltin chloride in 60ml of toluene, and slowly add the solution dropwise to the reaction system. After the dropwise addition, it will naturally rise to room temperature and react for 6h. After the reaction is completed, add 60ml of ice water to quench the reaction. The reaction solution was extracted with DCM (100ml*3) and saturated brine (100ml*2) respectively, and the organic phase was rotary evaporated to obtain an oily product, which was recrystallized using TOL (toluene) / EtOH to obtain a solid compound 1.

[0075] MALDI-TOF: 330.90.

[0076] 1 H NMR (400MHz, Chloroform) δ7.42(s,1H),7.31(s,1H),7.16(s,1H),7.06(s,1H),1.44(s,6H).

[0077] 13 C NMR (100MHz, Common NMR Solvents) δ149.97(s), 144.21(s), 126.15(s), 12...

Embodiment 2

[0092]

[0093] Add 8.70 g (20 mmol) of compound 4 into the reaction flask, add diethyl ether (50 mL) to dissolve, and replace with nitrogen three times. Cool down to -78°C, and when the temperature reaches, control the temperature below -65°C and slowly add n-BuLi8.04mL (2.5M, 20mmol) dropwise, and stir for 30min after the dropwise addition is complete. Then 6.37 g (20 mmol) of compound 6 was dissolved in 60 mL of toluene, and slowly added dropwise to the reaction solution. After the dropwise addition was completed, it was naturally raised to room temperature for 6 h. After the reaction was completed, 100 mL of ice water was added to quench the reaction. Then add DCM (80mL*2) for extraction, and finally extract once with saturated brine. The collected organic phase was rotary evaporated, and the product was purified by column chromatography (mobile phase n-hexane:dichloromethane=3:1) to obtain compound M2.

[0094] MALDI-TOF: 593.05.

[0095] 1 H NMR (400MHz, Chlorofor...

Embodiment 3

[0099]

[0100] In a 250mL three-necked flask, 5.45g (20mmol) of compound 2, 8.43g (25mmol) of compound 7, 150mL of toluene, 9.21g (40mmol) of cesium carbonate, and 0.23g of tetrakis (triphenylphosphine) palladium ( 0.2 mmol) and 40.5 mg (0.2 mmol) of tri-tert-butylphosphine, and then reacted at 120° C. for 24 hours under a nitrogen atmosphere. Cool to room temperature, pour the reaction solution into 200mL ice water, extract three times with dichloromethane, combine the organic phases, spin dry the solvent and apply the sample by dry method, column chromatography (dichloromethane:n-hexane, v:v=1:1) After separation and purification, compound 8 was obtained.

[0101] MALDI-TOF: 484.01.

[0102] 1 H NMR (400MHz, Chloroform-d) δ8.12 (dd, J = 7.4, 1.6Hz, 2H), 8.00 (ddd, J = 7.2, 3.3, 1.4Hz, 2H), 7.89 (dd, J = 7.5, 1.5 Hz,1H),7.61–7.53(m,4H),7.50(td,J=7.5,1.5Hz,1H),7.44(t,J=7.4Hz,1H),7.40–7.22(m,6H),7.19 (dd,J=7.5,1.6Hz,1H).

[0103] 13 C NMR(100MHz,Chloroform-d)δ163.36,1...

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Abstract

The application discloses a boron-containing compound, the general structure of which is as follows: for the definition of each substituent, please refer to the description. The boron-containing compound of the invention has TADF characteristics, and can utilize the triplet state excitons that are forbidden by traditional fluorescent molecular transitions to emit light, thereby improving device efficiency.

Description

technical field [0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a boron-containing compound, a display panel and a display device. Background technique [0002] According to the light-emitting mechanism, there are mainly four kinds of materials that can be used for OLED light-emitting layer: [0003] 1. Fluorescent material [0004] The singlet excited state S1 of the material returns to the ground state S0 by radiative transition. [0005] 2. Phosphorescent materials [0006] The triplet excited state T1 directly radiatively decays to the ground state S0 (Nature, 1998, 395, 151). [0007] 3. Triplet-triplet annihilation (TTA) materials [0008] Two triplet excitons interact to generate a singlet exciton, which transitions back to the ground state S0 through radiative transition (Adv. Funct. Mater., 2013, 23, 739). [0009] 4. Thermally Active Delayed Fluorescence (TADF) materials [0010] When the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1029C09K2211/104C09K2211/1059C09K2211/1033C09K2211/1037C09K2211/1044H10K85/636H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/657H10K50/11
Inventor 汪奎
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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