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An organic electroluminescent device containing azaphenyl compound and its application

An electroluminescent device, azaphenyl technology, applied in the field of semiconductors, can solve the problems of high exciton utilization rate and high fluorescence radiation efficiency, low S1 state radiation transition rate, efficiency roll-off, etc., to achieve high efficiency Effect

Active Publication Date: 2020-02-21
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) The T1 and S1 states of the designed molecule have strong CT features and a very small S1-T1 state energy gap, although high T can be achieved by the TADF process 1 →S 1 State exciton conversion rate, but at the same time lead to low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization rate and high fluorescence radiation efficiency;
[0007] (2) Even if doped devices have been used to alleviate the T-exciton concentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • An organic electroluminescent device containing azaphenyl compound and its application
  • An organic electroluminescent device containing azaphenyl compound and its application
  • An organic electroluminescent device containing azaphenyl compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1 Compound 1

[0065]

[0066] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,6-dibromo-2-phenyl-pyrimidine, 0.025mol 9,10-dihydro-9,9-dimethylacridine, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 - 4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled on a plate, and 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 99.2% and a yield of 66.00%.

[0067] Elemental analysis structure (molecular formula C 40 h 34 N 4 ): theoretical value C, 84.18; H, 6.00; N, 9.82; test value: C, 84.19; H, 6.04; N, 9.77.

[0068] HPLC-MS: The molecular weight of the material is 570.28, and the measured molecular weight is 570.80.

Embodiment 2

[0069] Example 2 Compound 2

[0070]

[0071] Add 0.01mol 3-biphenyl-4-yl-2,5-dibromo-pyrazine, 0.025mol 10H-phenoxazine, 0.03mol sodium tert-butoxide to a 250ml four-necked flask under nitrogen atmosphere , 1×10 -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 96.8% and a yield of 68.30%.

[0072] Elemental analysis structure (molecular formula C 40 h 26 N 4 o 2 : Theoretical value C, 80.79; H, 4.41; N, 9.42; O, 5.38; Test value: C, 80.82; H, 4.40; N, 9.41;

[0073] HPLC-MS: The molecular weight of the material is 594.21, and the measured molecular weight is 594.62.

Embodiment 3

[0074] Example 3 Compound 3

[0075]

[0076] Add 0.01mol 4-biphenyl-4-yl-3,6-dibromo-pyrazine, 0.025mol 10H-phenoxazine, 0.03mol sodium tert-butoxide to a 250ml four-necked flask under nitrogen atmosphere , 1×10 -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 95.0% and a yield of 72.30%.

[0077] Elemental analysis structure (molecular formula C 40 h 26 N 4 o 2 : Theoretical value C, 80.79; H, 4.41; N, 9.42; O, 5.38; Test value: C, 80.80; H, 4.36; N, 9.47;

[0078] HPLC-MS: The molecular weight of the material is 594.21, and the measured molecular weight is 594.69.

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Abstract

The invention discloses an organic electroluminescent device containing an azaphenyl compound, which comprises a hole transport layer, a light-emitting layer, and an electron transport layer, and the material of the light-emitting layer of the device comprises a compound containing an azaphenyl group , the structural formula of the compound is shown in general formula (1). Because the azaphenyl group material of the present invention has a smaller energy difference between the triplet state and the singlet state, it is easy to realize the energy transfer between the host and guest materials, so that the energy originally lost in the form of heat is easy to be used, and the radiative transition of the light-emitting layer is improved. Efficiency, so that it is easier to obtain high efficiency of the device, and further, when the dopant material is selected as a fluorescent material, it is easier to obtain the luminous radiation of the dopant material, so that it is easier to obtain a long life of the material.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic electroluminescent device whose light-emitting layer material is an azaphenyl compound and its application. 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-emit...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/14C07D413/14C07D498/04C07D491/048C07D417/14C07D519/00H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D413/14C07D417/14C07D491/048C07D498/04C07D519/00C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1033C09K2211/1037C09K2211/1029H10K85/653H10K85/655H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 李崇徐凯张兆超
Owner JIANGSU SUNERA TECH CO LTD
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