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Organic electroluminescent device containing acridine spiro anthrone compound, and application of organic electroluminescent device

An electroluminescent device, acridine spiroanthrone technology, applied in the field of organic electroluminescent devices, can solve difficult problems such as high exciton utilization rate and high fluorescence radiation efficiency, efficiency roll-off, low S1 state radiation transition rate, etc. , to achieve high efficiency

Active Publication Date: 2017-08-25
VALIANT CO LTD
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  • 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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  • Organic electroluminescent device containing acridine spiro anthrone compound, and application of organic electroluminescent device
  • Organic electroluminescent device containing acridine spiro anthrone compound, and application of organic electroluminescent device
  • Organic electroluminescent device containing acridine spiro anthrone compound, and application of organic electroluminescent device

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Experimental program
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Effect test

Embodiment 1

[0063] The synthesis of embodiment 1 compound 1

[0064]

[0065] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromodibenzofuran, 0.025mol acridinosiroanthrone, 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, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 99.2% and a yield of 67.00%.

[0066] Elemental analysis structure (molecular formula C 38 h 23 NO 2 ): theoretical value C, 86.84; H, 4.41; N, 2.66; O, 6.09; test value: C, 86.91; H, 4.44; N, 2.70;

[0067] HPLC-MS: The molecular weight of the material is 525.17, and the measured molecular weight is 525.71.

Embodiment 2

[0068] The synthesis of embodiment 2 compound 2

[0069]

[0070] In a 250ml four-necked flask, under a nitrogen atmosphere, add 0.01mol 2-(4-bromophenyl)-dibenzofuran, 0.025mol acridine spiroanthrone, 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, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product with a purity of 99.0% and a yield of 69.00%.

[0071] Elemental analysis structure (molecular formula C 44 h 27 NO 2 ): theoretical value C, 87.83; H, 4.52; N, 2.33; O, 5.32; test value: C, 87.88; H, 4.46; N, 2.30;

[0072] HPLC-MS: The molecular weight of the material is 601.20, and the measured molecular weight is 601.76.

Embodiment 3

[0073] The synthesis of embodiment 3 compound 4

[0074]

[0075] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 9-(4-bromophenyl)-9H-carbazole, 0.025mol acridine spiroanthrone, 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, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 95.8% and a yield of 74.00%.

[0076] Elemental analysis structure (molecular formula C 44 h 28 N 2 O): Theoretical value C, 87.97; H, 4.70; N, 4.66; O, 2.66; Test value: C, 87.96; H, 4.65; N, 4.63;

[0077] HPLC-MS: The molecular weight of the material is 600.22, and the measured molecular weight is 600.79.

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Abstract

The invention discloses an organic electroluminescent device containing an acridine spiro anthrone compound, and the organic electroluminescent device comprises a hole transmission layer, a light-emitting layer, and an electron transmission layer. The material of the light-emitting layer of the device contains an acridine spiro anthrone group compound, and the structural formula of the compound is shown in a general formula (1). The acridine spiro anthrone group compound is smaller in triplet state and singlet state energy difference, so the compound can achieve the energy transmission between host-guest materials easily, enables the energy which is originally dissipated in a mode of heat to be easy to obtain and use, and improves the radiative transition efficiency of the light-emitting layer, thereby enabling the device to be able to obtain high efficiency in an easier way. Furthermore, when the doped material is a fluorescent material, the light-emitting radiation of the doped material is easier to obtain, and the service life of the material is enabled to be long.

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 acridine-spirone anthrone compound and an application thereof. 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...

Claims

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Application Information

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IPC IPC(8): H01L51/54H01L51/50
CPCH10K85/623H10K50/11
Inventor 李崇徐凯张兆超
Owner VALIANT CO LTD
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