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A kind of organic aromatic compound and its application

A technology for aromatic compounds and compounds, applied in the fields of organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc. Achieve the effect of increasing orbital overlap, good film formation and fluorescence quantum efficiency, and avoiding aggregation

Active Publication Date: 2019-04-09
JIANGSU SUNERA TECH 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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  • A kind of organic aromatic compound and its application
  • A kind of organic aromatic compound and its application
  • A kind of organic aromatic compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: the synthesis of compound 01

[0051]

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

[0053]

[0054] In a 250ml four-necked flask, under a nitrogen atmosphere, add 0.012mol of intermediate A, 0.01mol of acridine spiroanthrone, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 250ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 98.6% and a yield of 65.4%.

[0055] Elemental analysis structure (molecular formula C 50 h 32 N 2 o 3 ): theoretical value C, 84.73; H, 4.55; N, 3.95; O, 6.77; test value: C, 84.57; H, 4.45; N, 3.87;

[0056] HPLC-MS: The molecular weight of the material is 708.80, and the measured molecular weight is 708.40.

Embodiment 2

[0057] Embodiment 2: the synthesis of compound 06

[0058]

[0059] The concrete synthetic route of this compound is provided now:

[0060]

[0061] In a 250ml four-neck flask, under an atmosphere of nitrogen gas, add 0.012mol of intermediate B, 0.01mol of acridine spiroanthrone, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 250ml toluene, heating and reflux for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product with a purity of 98.5% and a yield of 65.7%.

[0062] Elemental analysis structure (molecular formula C 59 h 41 N 3 o 1 ): theoretical value C, 87.70; H, 5.11; N, 5.20; O, 1.98; test value: C, 87.60; H, 5.04; N, 5.09;

[0063] HPLC-MS: The molecular weight of the material is 807.98, and the measured molecular weight is 807.67.

Embodiment 3

[0064] Embodiment 3: the synthesis of compound 16

[0065]

[0066] The concrete synthetic route of this compound is provided now:

[0067]

[0068] In a 250ml four-neck flask, under an atmosphere of nitrogen gas, add 0.012mol of intermediate C, 0.01mol of acridine spiroanthrone, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 250ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 97.8% and a yield of 70.1%.

[0069] Elemental analysis structure (molecular formula C 56 h 34 N 2 o 3 ): theoretical value C, 85.91; H, 4.38; N, 3.58; O, 6.13; test value: C, 85.78; H, 4.43; N, 3.54;

[0070] HPLC-MS: The molecular weight of the material is 782.88, and the measured molecular weight is 782.95.

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Abstract

The invention discloses an organic aromatic compound with acridine spirone anthrone as the core and its application in organic electroluminescent devices. It has the characteristics of good film-forming properties. The compound of the present invention is applied to an organic electroluminescent device as a light-emitting layer material, and the organic electroluminescent device using the compound of the present invention has good photoelectric performance, and can better adapt to and meet the application requirements of panel manufacturers.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic aromatic compound with acridinium spiroanthrone as the core, 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 el...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D411/04C07D413/04C07D401/14C07D401/04C07D491/048C07D491/056C07D491/052C07D498/04C07D513/04C07D487/04C07D221/20C07D498/14C07D491/147C07D409/04C07D409/10C07D417/10C07D417/04C07D401/10C07D495/04C07D405/10C07D403/10C07D413/10C07D417/14C07D413/14C07D421/14C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D221/20C07D401/04C07D401/10C07D401/14C07D403/10C07D405/04C07D405/10C07D409/04C07D409/10C07D411/04C07D413/04C07D413/10C07D413/14C07D417/04C07D417/10C07D417/14C07D421/14C07D487/04C07D491/048C07D491/052C07D491/056C07D491/147C07D495/04C07D498/04C07D498/14C07D513/04C09K2211/1029C09K2211/1044C09K2211/104C09K2211/1037C09K2211/1033C09K2211/1092C09K2211/1088H10K85/636H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 王立春叶中华李崇张兆超徐凯于凯朝
Owner JIANGSU SUNERA TECH CO LTD
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