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A kind of organic electroluminescent device containing ketone and nitrogen heterocyclic compound and its application

A compound and nitrogen heterocyclic technology, applied in the field of organic electroluminescent devices, can solve the problems of high exciton utilization rate and high fluorescence radiation efficiency, efficiency roll-off, low S1 state radiation transition rate, etc., to achieve high efficiency, The effect of a small energy gap difference

Active Publication Date: 2018-12-28
VALIANT 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 through 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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  • A kind of organic electroluminescent device containing ketone and nitrogen heterocyclic compound and its application
  • A kind of organic electroluminescent device containing ketone and nitrogen heterocyclic compound and its application
  • A kind of organic electroluminescent device containing ketone and nitrogen heterocyclic compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 Compound 1

[0060]

[0061] The concrete synthetic route of this compound is provided now:

[0062]

[0063] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.015mol9H-5-oxa-9,13b-diaza-naphthalene[3,2,1-de ] anthracene, 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, 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 98.2% and a yield of 70.00%.

[0064] HPLC-MS: The molecular weight of the material is 452.15, and the measured molecular weight is 452.22.

Embodiment 2

[0065] Example 2 Compound 2

[0066]

[0067] The concrete synthetic route of this compound is provided now:

[0068]

[0069] In a 250ml four-necked flask, add 0.01mol biphenyl-4-yl-(3-bromophenyl)methanone, 0.015mol 9H-5-oxa-9,13b-diazepine under nitrogen atmosphere -Naphth[3,2,1-de]anthracene, 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, 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 99.0% and a yield of 72.00%.

[0070] HPLC-MS: The molecular weight of the material is 528.18, and the measured molecular weight is 528.62.

Embodiment 3

[0071] Example 3 Compound 7

[0072]

[0073] The concrete synthetic route of this compound is provided now:

[0074]

[0075] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol (4-bromophenyl)-triphenylen-2-yl-methanone, 0.015mol 9,9-dimethyl-5H,9H- 5,13b-diaza-naphthalene[3,2,1-de]anthracene, 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, 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 76.00%.

[0076] HPLC-MS: The molecular weight of the material is 628.25, and the measured molecular weight is 628.67.

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Abstract

The invention discloses an organic electroluminescent device containing a ketone and a nitrogen heterocyclic compound. The device includes a hole transport layer, a light-emitting layer, and an electron transport layer. The compound, the structural formula of the compound is shown in general formula (1). The material containing ketones and nitrogen heterocyclic rings in the present invention has a smaller triplet and singlet energy difference, so it is easy to realize energy transfer between host and guest materials, so that the energy originally lost in the form of heat can be easily used, and the light-emitting layer can be improved. Radiation transition 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 luminescent 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 electroluminescence device in which the light-emitting layer material is a ketone and nitrogen heterocyclic 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 bo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/52H01L51/54C09K11/06
CPCC09K11/06C09K2211/1029C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1092C09K2211/1088H10K85/6572H10K85/657H10K50/11
Inventor 李崇徐凯张兆超
Owner VALIANT CO LTD
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