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Compound, display panel and display device

A compound and unsubstituted technology, applied in the field of organic electroluminescence, can solve the problem of less materials, achieve high glass transition temperature, easy to obtain, and improve luminous efficiency

Active Publication Date: 2020-07-17
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few TADF materials have been found so far

Method used

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  • Compound, display panel and display device
  • Compound, display panel and display device
  • Compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0133] Synthesis of compound P001:

[0134] Synthesis of Intermediate X3:

[0135]

[0136] Under nitrogen atmosphere, X1 (21mmol), X2 (10mmol) and Pd(PPh 3 ) 4 (0.5 mmol) was added to 250 mL of anhydrous toluene, after deoxygenation for 10 min, the temperature was raised to 120° C., and the reaction was carried out for 24 h. After the reaction is completed, cool to room temperature, filter with diatomaceous earth, collect the filtrate and add dichloromethane (DCM), H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 Dry, collect the filtrate by suction filtration, spin off the solvent, and recrystallize the crude product to obtain the intermediate product X3 (8.5 mmol, 85%), which is verified by mass spectrometry and put into the next step;

[0137] Intermediate X3: LC-MS: m / z: Calculated: C 49 h 32 B 2 o 3 : 690.4, measured value: 689.9.

[0138] Synthesis of Intermediate X4:

[0139]

[0140] The X3 intermediate (10 mmol) ...

preparation example 2

[0155] Synthetic compound P008

[0156]

[0157] Under a nitrogen atmosphere, add 100mL of 1,4-dioxane solvent into a 250mL reaction flask, and then add K 2 CO 3 (12.5mmol) solution, intermediate reactants X5 (5mol), X7 (11mmol), and Pd (PPh 3 ) 4 (0.25 mmol), heated to 120°C, and reacted overnight. After the reaction is completed, cool to room temperature, add DCM, H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 After drying, the filtrate was collected by suction filtration, the solvent was spun off and purified by column chromatography to obtain compound P008 (4.2 mmol, 84%).

[0158] LC-MS: m / z: Calculated: C 85 h 52 B 2 N 2 o 2 : 1155.0, measured value: 1154.5.

[0159] 1 H NMR (400MHz, CDCl 3 )δ=8.26-8.23(m, 2H), 8.12-8.04(m, 4H), 7.79-7.65(m, 16H), 7.61-7.49(m, 14H), 7.46-7.29(m, 8H), 7.25- 7.13 (m, 4H), 7.10-6.89 (m, 4H).

[0160] Compound elemental analysis results: Calculated value: C 85 h 52 B 2 N 2 o 2...

preparation example 3

[0162] Synthetic compound P013

[0163]

[0164] Under nitrogen atmosphere, in 100mL of anhydrous toluene solvent, add intermediate reactants X5 (1mol), X8 (2.2mmol), sodium tert-butoxide (2.5mmol) and Pd in ​​sequence 2 (dba) 3 (0.05mmol), S-Phos (0.15mmol), heated to 110°C, and reacted overnight. After the reaction is completed, cool to room temperature, add DCM, H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 After drying, the filtrate was collected by suction filtration, the solvent was spun off and purified by column chromatography to obtain compound P013 (0.8 mmol, 80%).

[0165] LC-MS: m / z: Calculated: C 79 h 56 B 2 N 2 o 2 :1086.9, measured value: 1086.4.

[0166] 1 H NMR (400MHz, CDCl 3 ):δ=8.25(d,2H),8.10-8.01(m,4H),7.78-7.60(m,12H),7.59-7.47(m,12H),7.41-7.27(m,6H),7.25-7.10 (m, 4H), 7.08-6.89 (m, 4H), 1.68-1.65 (m, 12H).

[0167] Compound elemental analysis results: Calculated value: C 79 h 56 B 2 N 2 o ...

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Abstract

The present invention relates to a compound, a display panel and a display device, the compound has a structure represented by a formula I, the compound uses a spiro structure as a non-conjugated connection unit and a boron-containing group as an electron accepting group, and the groups are used as building blocks to obtain a light emitting compound having a narrower half-peak width and a higher color purity. A bipolar compound can be obtained by connecting an electron-donating group to the boron-containing spiro structure, and the bipolar compound can be used as a thermal activation delayed fluorescence material as a luminescent layer material, especially a doping material, and as a fluorescent host material or a phosphorescent host material. When the compound provided by the invention isapplied to an organic light-emitting device, low driving voltage and high light-emitting efficiency can be realized.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound, a display panel and a display device. Background technique [0002] With the development of electronic display technology, organic light-emitting devices (OLEDs) are widely used in various display devices, and the research and application of OLED light-emitting materials are also increasing. [0003] According to the light-emitting mechanism, the materials used for the OLED light-emitting layer mainly include the following four types: [0004] (1) fluorescent materials; (2) phosphorescent materials; (3) triplet-triplet annihilation (TTA) materials; (4) thermally activated delayed fluorescence (TADF) materials. [0005] For thermally activated delayed fluorescence (TADF) materials, when the energy level difference between the singlet excited state and the triplet excited state is small, reverse intersystem crossing (RISC) occurs inside the molecule...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1096C09K2211/104C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1033H10K85/636H10K85/657H10K85/6572H10K50/12H10K50/11H10K85/658H10K85/342H10K2101/10H10K2101/20Y02E10/549C07F5/02H10K85/40H10K85/633
Inventor 高威代文朋张磊冉佺牛晶华李侠
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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