Organic aromatic compound and application of organic aromatic compound in organic electroluminescent device

An aromatic compound and compound technology, applied in organic chemistry, electrical solid devices, electrical components, etc., can solve the problems of low S1 state radiation transition rate, difficult exciton utilization rate, high fluorescence radiation efficiency, and efficiency roll-off, etc. Good prospects for industrialization, avoiding agglomeration, increasing the effect of track overlap

Active Publication Date: 2017-03-01
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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  • Organic aromatic compound and application of organic aromatic compound in organic electroluminescent device
  • Organic aromatic compound and application of organic aromatic compound in organic electroluminescent device
  • Organic aromatic compound and application of organic aromatic compound in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of compound 01

[0049]

[0050] The concrete synthetic route of this compound is provided now:

[0051]

[0052] 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 16 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 98.7% and a yield of 62.8.00%.

[0053] Elemental analysis structure (molecular formula C 50 h 23 N 2 o 2 ): theoretical value C, 86.68; H, 4.66; N, 4.04; O, 4.62; test value: C, 86.80; H, 4.57; N, 3.92;

[0054] HPLC-MS: The molecular weight of the material is 692.8, and the measured molecular weight is 692.3.

Embodiment 2

[0055] Embodiment 2: the synthesis of compound 04

[0056]

[0057] The concrete synthetic route of this compound is provided now:

[0058]

[0059] 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 of tri-tert-butylphosphine, 200ml of toluene, heating and reflux for 20 hours, sampling point plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 98.2% and a yield of 70.05%.

[0060] Elemental analysis structure (molecular formula C 56 h 37 N 3 O): theoretical value C, 87.59; H, 4.86; N, 5.47; O, 2.08; tested value: C, 87.45; H, 4.66; N, 5.31;

[0061] HPLC-MS: The molecular weight of the material is 767.91, and the measured molecular weight is 761.54.

Embodiment 3

[0062] Embodiment 3: the synthesis of compound 05

[0063]

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

[0065]

[0066] 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 tri-tert-butylphosphine, 250ml toluene, heated to reflux for 20 hours, sampled and spotted, reacted completely, naturally cooled, filtered, filtrate rotary evaporated, passed through a silica gel column to obtain the target product with a purity of 97.8% and a yield of 68.2%.

[0067] Elemental analysis structure (molecular formula C 56 h 37 N 3 O): Theoretical value C, 87.59; H, 4.86; N, 5.47; O, 2.08; Test value: C, 87.42;

[0068] HPLC-MS: The molecular weight of the material is 767.91, and the measured molecular weight is 761.61.

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Abstract

The invention discloses an organic aromatic compound and an application of the organic aromatic compound in an organic electroluminescent device, and the compound has good film forming ability. The compound as a luminescent layer material can be used on the organic electroluminescent device, the organic electroluminescent device by using the compound has good photoelectric property, and is suitable for and satisfies the application requirements of a panel manufacture enterprise.

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 Applications(China)
IPC IPC(8): C07D405/04C07D405/10C07D401/10C07D401/14C07D221/20C07D491/048C07D487/04C07D491/153C07D491/147C07D409/04C07D495/04C07D487/14C07D413/14C07D417/14C07D405/14C07D409/14C09K11/06H01L51/54
CPCC09K11/06C07D221/20C07D401/10C07D401/14C07D405/04C07D405/10C07D405/14C07D409/04C07D409/14C07D413/14C07D417/14C07D487/04C07D487/14C07D491/048C07D491/147C07D491/153C07D495/04C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1007C09K2211/1011H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 李崇叶中华张兆超王立春徐凯于凯朝
Owner JIANGSU SUNERA TECH CO LTD
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