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A kind of red light thermally activated delayed fluorescent material and organic electroluminescent device

A heat-activated delay and fluorescent material technology, applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve the problems of unfriendly environment, unstable performance, low durability, etc., and achieve high radiation transition rate and good stability , Improve the effect of efficiency and stability

Active Publication Date: 2019-02-19
KUNSHAN GO VISIONOX OPTO ELECTRONICS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For this reason, the present invention aims at the problems of unstable performance, low durability, high cost and unfriendly environment of existing red phosphorescent material devices, and further provides a kind of red light thermally activated delayed fluorescent material whose singlet-triplet energy gap (ΔE ST ) is very small, the triplet excitons can be transformed into singlet excitons to emit light through reverse intersystem jumping (RIST), which can improve the efficiency and stability of red OLED devices

Method used

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  • A kind of red light thermally activated delayed fluorescent material and organic electroluminescent device
  • A kind of red light thermally activated delayed fluorescent material and organic electroluminescent device
  • A kind of red light thermally activated delayed fluorescent material and organic electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Synthetic method of the structural compound shown in formula (1-1): under nitrogen range, 4,5-difluoro-1,2-dicyanobenzene (5mmol), phenoxazine (18mmol), Pd 2 (dba) 3 (0.8mmol), NaOtBu (30mmol) and tBu 3 P·HBF 4 (0.8 mmol) was put into 100 mL of dimethylformamide DMF and stirred overnight at a temperature of 80°C. The reaction was quenched by adding 10 mL of cold water to the mixture. After the mixture was cooled to room temperature, the product formula (1-1) was purified by vacuum filtration, followed by column chromatography, and the product was dried in vacuum. Yield: 69%.

[0053] Mass spectrometry gave molecular weight: 490.14.

[0054] The relative molecular mass percentage of each element obtained by elemental analysis: C, 78.36; H, 3.70; N, 11.42; O, 6.52.

Embodiment 2

[0056] Synthetic method of the structural compound shown in formula (1-2): the reactant phenoxazine is replaced by phenothiazine, and through the same synthetic method as in Example 1, the structural compound shown in formula (1-2) is obtained, and the yield is 79% .

[0057] Mass spectrometry gave molecular weight: 522.10.

[0058] The relative molecular mass percentage of each element obtained by elemental analysis: C, 73.54; H, 3.47; N, 10.72; S, 12.27.

Embodiment 3

[0060] Synthesis method of the compound with the structure shown in formula (1-3): the reactant phenoxazine is replaced by 9,9-dimethylacridine, and the structure shown in formula (1-3) is obtained through the same synthesis method as in Example 1 Compound, yield 82%.

[0061] Mass spectrometry gave molecular weight: 542.25.

[0062] The relative molecular mass percentage of each element obtained by elemental analysis: C, 84.10; H, 5.57; N, 10.32.

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Abstract

A red-light thermally activated delayed fluorescent material of the present invention has a general formula of the structure shown in formula (I), wherein one substituent in R1-R5 is a cyano group, two are hydrogen groups, and the remaining two substituents are the same Or different, respectively selected from electron-donating groups, the electron-donating groups are phenoxazinyl, phenothiazinyl, 9,9-dimethylacridinyl, 9-methylphenazinyl, 9- Phenylphenazinyl, 4-phenoxazinyl-1-phenyl, 4-phenothiazinyl-1-phenyl, 4-(9,9-dimethyl)acridinyl-1-phenyl, One or more of 4-(9-methyl)phenazinyl-1-phenyl or 4-(9-phenyl)phenazinyl-1-phenyl. The invention also relates to an organic electroluminescence device, which comprises a luminescent layer, and the luminescent dye of the luminescent layer is the thermally activated delayed fluorescent material. The singlet-triplet energy gap (ΔEST) of thermally activated delayed fluorescent materials is very small, and triplet excitons can be transformed into singlet excitons to emit light through reverse intersystem jumping (RIST), which can improve the efficiency of red OLED devices and stability. .

Description

technical field [0001] The invention relates to a light emitting layer material, in particular to a red light heat activated delayed fluorescent material which can be used in the light emitting layer and an organic electroluminescent device with the red light heat activated delayed fluorescent material. Background technique [0002] Organic Light Emitting Diode (OLED) is a current-driven light-emitting device that uses organic materials as active materials. Specifically, organic semiconductor materials and organic light-emitting materials are driven by electric fields through carrier injection and Composite technology that leads to luminescence. Unlike inorganic materials, organic materials have the characteristics of low synthesis cost, adjustable function, flexibility, and good film-forming properties. Moreover, devices based on organic materials are generally simple in fabrication process, easy to be prepared in a large area, and are environmentally friendly, and can ado...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/38C07D279/22C07D219/14C07D241/48C09K11/06H01L51/54
CPCC09K11/06C07D219/14C07D241/48C07D265/38C07D279/22C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1029C09K2211/1007C09K2211/1011H10K85/657H10K85/6572H10K50/00
Inventor 段炼张云阁刘嵩赵菲
Owner KUNSHAN GO VISIONOX OPTO ELECTRONICS CO LTD