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Organic light emission diode device containing ketone and nitrogen heterocycle compound and application thereof

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

Active Publication Date: 2017-08-18
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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  • Organic light emission diode device containing ketone and nitrogen heterocycle compound and application thereof
  • Organic light emission diode device containing ketone and nitrogen heterocycle compound and application thereof
  • Organic light emission diode device containing ketone and nitrogen heterocycle compound and application thereof

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 light emission diode device containing a ketone and nitrogen heterocycle compound and an application thereof. The device comprises a hole transport layer, a light emission layer and an electron transport layer. The material of the light emission layer of the device comprises a compound comprising ketone and nitrogen heterocycle groups, and the structural formula of the compound is shown in the general formula (1). According to the ketone and nitrogen heterocycle material, due to a small triplet and singlet energy difference, energy transfer between host and guest materials can be realized easily, energy that is originally lost in a heat form is easily available, the radiative transition efficiency of the light emission layer is enhanced, and the high efficiency of the device can be acquired more easily. Further, when a fluorescent material is selected as a doped material, light emission radiation of the doped material is acquired more easily, and a long service life of the material can be acquired more easily.

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 Applications(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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