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Compound, application thereof and organic light-emitting device comprising compound

A compound and selected technology, applied in the field of organic electroluminescent devices, can solve the problems that the performance needs to be further improved

Active Publication Date: 2020-07-07
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The organic electroluminescent device prepared by using the thermally activated delayed fluorescent material has an external quantum efficiency of 8.54% to 11.64%, a maximum current efficiency of 11.24cd / A, and a maximum power efficiency of 16.34Lm / W. Item performance still needs to be further improved

Method used

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  • Compound, application thereof and organic light-emitting device comprising compound
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  • Compound, application thereof and organic light-emitting device comprising compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0153] Synthesis of compound M1:

[0154]

[0155] (1) Synthesis of intermediate M1-1

[0156] Add 67.5g (150mmol) of 2-bromo-1-(2-bromophenyl)-4-iodobenzene and 20.9g (100mmol) of 9,9-dimethylacridine into a freshly dried 2000mL two-necked bottle , then add 20.7g (150mmol) of anhydrous potassium carbonate, 19.0g (100mmol) of cuprous iodide, 180g (100mmol) of phenanthroline and 1200mL of dry N,N-dimethylformamide (DMF), room temperature After stirring for 0.5 hours, the temperature was raised to 130 degrees Celsius to continue the reaction for 10 hours. After the reaction was completed, it was lowered to room temperature, and the solvent in the reaction system was distilled off under reduced pressure. The crude product was dissolved in 500 mL of dichloromethane and washed with a large amount of water. The organic phase was dried with anhydrous sodium sulfate and then concentrated. Dichloromethane:petroleum ether=1:10 was used as the eluent for column chromatography to obt...

preparation example 2

[0164] Synthesis of Compound M2:

[0165] The difference from Preparation Example 1 is that 9,9-dimethylacridine was replaced by 9,9-diphenylacridine in an equivalent amount to obtain 3.2 g of product M2 with a yield of 50.8%. The molecular mass determined by mass spectrometry is: 635.21 (calculated value: 635.20); theoretical element content (%) C 44 h 30 NO 2 P: C, 83.13; H, 4.76; N, 2.20; O, 5.03; P, 4.87. Measured element content (%): C, 83.11; H, 4.75; N, 2.19.

[0166] The above analysis results indicated that the obtained product was the expected product.

preparation example 3

[0168] Synthesis of compound M10:

[0169] The difference with Preparation Example 1 is that 2-bromo-1-(2-bromophenyl)-4-iodobenzene is replaced by bis(2-bromo-4-iodophenyl)methane of equal substance amount to obtain 2.4 g product M10, the yield is 34.6%.

[0170] The molecular mass determined by mass spectrometry is: 718.30 (calculated value: 718.27); theoretical element content (%) C 49 h 39 N 2 o 2 P: C, 81.87; H, 5.47; N, 3.90; O, 4.45; P, 4.31. Measured element content (%): C, 81.89; H, 5.45; N, 3.87.

[0171] The above analysis results indicated that the obtained product was the expected product.

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Abstract

The invention provides a compound, application thereof and an organic light-emitting device comprising the compound. The compound has a structure as shown in a formula (I), wherein carbonyl, a phosphorus atom, a phosphine oxide group, a phosphine sulfur group or a phosphine selenium group jointly serve as an acceptor group; the application of the compound is as a material of a light-emitting layerin an organic light-emitting device; the organic light-emitting device comprises a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, wherein the compound is contained in the organic layer. The compound has good electron transport capability, proper carrier mobility and low injection energy barrier, and can effectively reduce the turn-onvoltage and improve the luminous efficiency when used in organic electroluminescent devices.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound and its application, and an organic electroluminescence device containing it. Background technique [0002] Organic light-emitting diodes (OLEDs) have many advantages such as self-illumination, wide viewing angle, low power consumption, and high contrast, so they have a wide range of applications in white lighting, flexible displays, ultra-thin displays, and transparent displays. [0003] Due to the large energy level difference between the singlet state and the triplet state, traditional fluorescent materials can only use 25% of the singlet state excitons to emit light, and OLEDs consume a lot of power. Phosphorescent materials containing heavy metals can simultaneously utilize singlet and triplet excitons to emit light due to the spin-orbit coupling effect of the heavy atom effect, and the internal quantum utilization rate can reach up to 100%. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C09K11/06H01L51/54
CPCC07F9/65685C09K11/06C09K2211/1029C09K2211/1096C09K2211/104C09K2211/1033C09K2211/1037H10K85/657H10K85/6572H10K85/40
Inventor 魏金贝高文正李国孟孙磊
Owner BEIJING ETERNAL MATERIAL TECH
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