Thermally activated delayed fluorescent materials and application thereof

A technology of heat-activated delayed and fluorescent materials, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of limiting the application space of phosphorescent materials, expensive phosphorescent materials, etc., and achieve excellent film stability and molecular quality , Excellent effect of device efficiency

Inactive Publication Date: 2018-08-10
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The efficiency of phosphorescent devices is higher than that of fluorescent devices. However, phosphorescent devices also have their disadvantages. For example, phosphorescent materials are mainly complexes containing noble meta

Method used

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  • Thermally activated delayed fluorescent materials and application thereof
  • Thermally activated delayed fluorescent materials and application thereof
  • Thermally activated delayed fluorescent materials and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1 compound C01:

[0036]

[0037] Preparation of intermediate B1: In a 500mL three-necked flask, add raw material A1 (6.0g, 0.015mol, CAS-RN: 74129-87-6), raw material 9,9-dimethylacridine (8.78g, 0.042mol) , copper powder (2.5g, 0.04mol), potassium carbonate (8.3g, 0.06mol), o-dichlorobenzene (180g), under the protection of nitrogen, heat up to 160°C, keep the temperature for 32 hours, cool down to 25°C, add tetrahydrofuran 120g, suction filtration, collect filtrate, remove solvent under reduced pressure, obtain B1 crude product 15.4g, the gained crude product is purified by silica gel column chromatography, eluent is n-hexane: dichloromethane=1:1 (v / v), Obtained 7.4g of B1 fine product, yield 75%, high resolution mass spectrum, positive ion mode, molecular formula C 44 h 36 N 2 S 2 , the theoretical value is 656.2320, and the test value is 656.2327.

[0038] Preparation of compound C01: In a 500mL three-necked flask, add compound ...

Embodiment 2

[0039] The preparation of embodiment 2 compound C02:

[0040]

[0041] Using phenoxazine as a raw material, refer to the method described in Example 1 to prepare compound C02, and obtain 1.7 g of the target object, high-resolution mass spectrum, positive ion mode, molecular formula C 38 h 24 N 2 o 6 S 2 , theoretical value 668.1076, test value 668.1071, elemental analysis (C 38 h 24 N 2 o 6 S 2 ), theoretical value C: 68.25, H: 3.62, N: 4.19, O: 14.35, S: 9.59, measured value C: 68.27, H: 3.66, N: 4.17, O: 14.30, S: 9.60.

Embodiment 3

[0042] The preparation of embodiment 3 compound C03:

[0043]

[0044] Using 5-phenyl-5,10-dihydrodiazaxanthene as a raw material, refer to the method described in Example 1 to prepare compound C03, and obtain 1.9 g of the target compound, high-resolution mass spectrometry, positive ion mode, molecular formula C 50 h 34 N 4 o 4 S 2 , theoretical value 818.2021, test value 818.2027, elemental analysis (C 50 h 34 N 4 o 4 S 2 ), theoretical value C: 73.33, H: 4.18, N: 6.84, O: 7.81, S: 7.83, measured value C: 73.36, H: 4.18, N: 6.83, O: 7.80, S: 7.83.

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Abstract

The invention relates to thermally activated delayed fluorescent materials and an application thereof. A molecular structure of the materials provided by the invention has a very small triplet state-singlet state energy level difference, a suitable molecular energy level and good film stability; and thermal activation delay fluorescent luminescence can be realized, and the materials are used as aluminescent layer of an organic electroluminescent device to be used in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and in particular relates to a small molecule organic electroluminescence material capable of realizing heat-activated delayed fluorescent light emission, and relates to the application of the material in the field of organic electroluminescence. Background technique [0002] Organic electroluminescent diode (OLED) was produced in the 1980s. It has many advantages such as self-illumination, wide viewing angle, fast response speed, wide color gamut, and flexible display. After 30 years of continuous development, the OLED The technology has gradually matured. At present, organic electroluminescent technology has been widely used in many products such as smart phones, flat-panel TVs, and virtual reality. [0003] Organic electroluminescent devices are current-driven light-emitting devices. According to different light-emitting mechanisms, they can be divided into two types: fluorescent dev...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D219/02C07D265/38C07D241/46C07D209/86C09K11/06H01L51/54
CPCC09K11/06C07D209/86C07D219/02C07D241/46C07D265/38C07D495/04C07C2603/40C09K2211/1092C09K2211/1033C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1029H10K85/622H10K85/626H10K85/6576H10K85/657H10K85/6572
Inventor 盛磊李子澍高树坤李小梅胡葆华柏忠源
Owner VALIANT CO LTD
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