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A boron-containing compound, display panel and display device

A boron compound and display panel technology, applied in the field of display panels and display devices, and boron-containing compounds, can solve the problems of high production costs, phosphorescent material efficiency roll-off, unfavorable mass production, etc., to improve device efficiency, reduce overlap, Enhanced effect of reverse crossing

Active Publication Date: 2022-02-15
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.
[0016] 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

[0062]

[0063] In a 250ml three-necked flask, add 3.56g (20mmol) of phenanthrene, that is, compound 1, compound 2, that is, 1.56g (20mmol) of benzene, and 1.78g (24mmol) of glyoxylic acid, mix and cool to 0°C, and then slowly add loaded trifluoro Methanesulfonic acid polyvinylpyrrolidone PVP-TfOH (3 g), the reaction mixture was warmed up to room temperature and stirred, and the reaction progress was monitored by TLC (hexane / ethyl acetate=3:1). After the reaction was complete, the mixture was poured into ice water, neutralized with saturated sodium bicarbonate, and extracted with ether (3×15 mL). The combined organic extracts were washed with water and washed with anhydrous Na 2 SO 4 After drying, the solvent was removed by evaporation in vacuo and the crude product was purified by column chromatography on silica gel using hexane / ethyl acetate as eluent. Add 75ml of thionyl chloride to the obtained product and mix coldly, heat the reaction mixture under reflux for 3 hours...

Embodiment 2

[0089]

[0090] Add compound 7 (1.95g) and diethyl ether (30mL) into a 250ml three-necked flask, replace with nitrogen three times, cool down to -78°C, control the temperature below -65°C and slowly add n-BuLi (0.34g) dropwise after the temperature reaches, After the dropwise addition was complete, stir for 30 minutes, then dissolve compound 8-2 (1.79 g) in 30 mL of toluene, slowly add it dropwise to the reaction solution, and naturally rise to room temperature for 6 hours after the dropwise addition, and add ice water (500 mL) to quench the reaction solution after the reaction. The reaction was quenched, and DCM (40mL*2) was added for extraction, and finally extracted once with saturated brine, and the collected organic phase was rotary evaporated to obtain a light yellow solid. 15 mL of toluene was added for thermal dissolution and crystallization to obtain compound M2.

[0091] 1 H NMR (400MHz, Chloroform) δ8.92 (d, J = 2.0Hz, 15H), 8.84 (s, 7H), 7.87 (t, J = 34.0Hz, 21...

Embodiment 3

[0094]

[0095] Add compound 7 (1.95g) and diethyl ether (30mL) into a 250ml three-necked flask, replace with nitrogen three times, cool down to -78°C, control the temperature below -65°C and slowly add n-BuLi (0.34g) dropwise after the temperature reaches, After the dropwise addition was complete, stir for 30min, then dissolve compound 8-3 (1.72g) in 30mL of toluene, slowly add dropwise to the reaction solution, after the dropwise addition, naturally rise to room temperature and react for 6h, after the reaction, add ice water (500mL) to quench The reaction was quenched, and DCM (40mL*2) was added for extraction, and finally extracted once with saturated brine, and the collected organic phase was rotary evaporated to obtain a light yellow solid. 15 mL of toluene was added for thermal dissolution and crystallization to obtain compound M3.

[0096] 1 H NMR (400MHz, Chloroform) δ9.15–8.82(m,35H),7.87(t,J=34.0Hz,43H),7.73(d,J=3.5Hz,7H),7.74–7.61(m,45H) ,7.50(s,8H),7.42(s,6H),...

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Abstract

The present application discloses a boron-containing compound, the general structure of which is shown in formula I: wherein, R is an electron donor, selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl. The boron-containing compound provided by the present invention is a new type of boron heterocyclic organic small molecule luminescent material, which avoids the aggregation of the compound and the direct accumulation of conjugated planes to form π aggregation or exciton by accessing groups with large steric hindrance. associations, thereby improving the luminous 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): C07F5/02C09K11/06H01L27/32
CPCC07F5/02C07F5/025C09K11/06C09K2211/1007C09K2211/1011C09K2211/1096C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092H10K59/10
Inventor 瞿星权汪奎叶添昇
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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