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Compound taking anthranone as core and application of compound in organic electroluminescent devices

A technology of light-emitting devices and compounds, applied to organic light-emitting diodes, the field of compounds containing anthrone, can solve the problems of low S1 state radiation transition rate, difficult exciton utilization rate, high fluorescence radiation efficiency, efficiency roll-off and the like , to achieve good film formation and fluorescence quantum efficiency, avoid aggregation, and increase the effect of orbital overlap

Inactive Publication Date: 2017-08-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • Compound taking anthranone as core and application of compound in organic electroluminescent devices
  • Compound taking anthranone as core and application of compound in organic electroluminescent devices
  • Compound taking anthranone as core and application of compound in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Compound 1

[0052] The concrete synthetic route of this compound is provided now:

[0053]

[0054] In a 250ml four-necked flask, add 0.01mol 3-(4-bromophenyl)-10,10-dimethyl-10H-anthrone, 0.03mol 9,9-dimethylacridine under nitrogen atmosphere Pyridine, 0.03mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 - 4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 95.2% and a yield of 77.00%.

[0055] HPLC-MS: The molecular weight of the material is 505.24, and the measured molecular weight is 505.29.

Embodiment 2

[0056] Example 2 Compound 2

[0057]

[0058] The concrete synthetic route of this compound is provided now:

[0059]

[0060] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-(3-bromophenyl)-10,10-dimethyl-10H-anthrone, 0.03mol phenoxazine, 0.03mol tert-butyl Sodium alkoxide, 1 x 10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.20% and a yield of 73.50%.

[0061] HPLC-MS: The molecular weight of the material is 479.19, and the measured molecular weight is 479.46.

Embodiment 3

[0062] Example 3 Compound 4

[0063]

[0064] The concrete synthetic route of this compound is provided now:

[0065]

[0066] In a 250ml four-necked flask, add 0.01mol 3,6-dibromo-10,10-diphenyl-10H-anthrone, 0.03mol 5-phenylphenazine, 0.03mol tert-butyl Sodium alkoxide, 1 x 10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.1% and a yield of 73.60%.

[0067] HPLC-MS: The molecular weight of the material is 858.34, and the measured molecular weight is 858.52.

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Abstract

The invention discloses a compound taking anthranone as a core and an application of the compound in organic electroluminescent devices. The compound has the characteristics that molecules are not prone to crystallization and not prone to aggregation and the film forming property is good, and the thermal stability of the material can be improved due to rigid radicals in the molecules. The compound disclosed by the invention is applied to the organic electroluminescent devices as a luminescent layer material, and manufactured organic electroluminescent devices have good photoelectric properties and can meet the requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing anthrone and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-e...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D219/02C07D221/20C07D221/18C07D265/34C07D241/38C07D265/38C07D279/22C07D241/48C07D471/04C07D497/04C07D413/04C07D401/04C07D491/048C07D513/04C07D491/056C07D498/04C07D519/00C07D498/14H01L51/50H01L51/54
CPCC09K11/06C07D219/02C07D221/18C07D221/20C07D241/38C07D241/48C07D265/34C07D265/38C07D279/22C07D401/04C07D413/04C07D471/04C07D491/048C07D491/056C07D497/04C07D498/04C07D498/14C07D513/04C07D519/00C09K2211/1088C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044H10K85/656H10K85/654H10K85/6572H10K85/657H10K50/12
Inventor 李崇徐凯张兆超
Owner VALIANT CO LTD
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