Organic compound with ketone structure as mother nucleus and application thereof in OLED device

An organic compound and compound technology, applied to the application of organic light-emitting diodes, based on the compound field with the ketone structure as the core, can solve the problem of difficult exciton utilization, high fluorescence radiation efficiency, low S1 state radiation transition rate, and efficiency rollover. To solve the problem of downgrading, achieve the effect of avoiding agglomeration, good industrialization prospects, and increasing orbital overlap

Inactive Publication Date: 2018-02-02
VALIANT 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 compound with ketone structure as mother nucleus and application thereof in OLED device
  • Organic compound with ketone structure as mother nucleus and application thereof in OLED device
  • Organic compound with ketone structure as mother nucleus and application thereof in OLED device

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Effect test

Embodiment 1

[0043] The synthesis of embodiment 1 intermediate A

[0044]

[0045]Under a nitrogen atmosphere, weigh the raw material I and dissolve it in tetrahydrofuran, then add the raw material II and tetrakis(triphenylphosphine) palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above reactants at a reaction temperature of 70- At 90°C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain intermediate B;

[0046] The molar ratio of raw material I to raw material II is 1:1.0 to 1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material I is 0.001 to 0.02:1, and the molar ratio of potassium carbonate to raw material I is 1.0 to 2.0:1 , the ratio of tetrahydrofuran to raw material I is 1g:10-3...

Embodiment 2

[0054] The synthesis of embodiment 2 compound 01

[0055]

[0056] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol of intermediate A1, 0.015mol of raw material B1, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150ml toluene, heated to 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 99.12% and a yield of 48.90%.

[0057] Elemental analysis structure (molecular formula C 39 h 23 NO 2 ): theoretical value C, 87.13; H, 4.31; N, 2.61; 0, 5.95; test value: C, 87.15; H, 4.29; N, 2.58; ESI-MS(m / z)(M + ): The theoretical value is 537.17, and the measured molecular weight is 537.23.

Embodiment 3

[0058] The synthesis of embodiment 3 compound 10

[0059]

[0060] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol intermediate A2, 0.015mol raw material B2, 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 97.62% and a yield of 50.82%.

[0061] Elemental analysis structure (molecular formula C 39 h 23 NO 2 ): theoretical value C, 87.13; H, 4.31; N, 2.61; 0, 5.95; test value: C, 87.11; ESI-MS(m / z)(M + ): The theoretical value is 537.17, and the measured molecular weight is 537.21.

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Abstract

The present invention discloses an organic compound with a ketone structure as a mother nucleus and application thereof in an organic electroluminescent device, the organic compound has the characteristics that Delta Est< 0.2 eV, and a 2.7 eV< T1< 3.0 eV, the organic compound is connected with aromatic heterocyclic groups for destruction of molecular symmetry, molecular crystallinity is destructed, intermolecular aggregation can be avoided, and the organic compound has good film-forming properties. When the organic compound is used as an emitting layer material of an organic light-emitting diode, the OLED device using the compound has good photoelectric properties and can meet the requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound based on a ketone structure as the core and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic Light Emitting Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat-panel display product at home and abroad. Domain, low operating voltage (3 ~ 10V), thin panel (less than 1mm) and rollable characteristics. OLED is hailed as the star flat panel display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and its future is limitless. [0003] The principle of OLED light emission is that by applying an external voltage, holes and electrons are injected from the anode and cathode after overcoming the interface energy barrier, and enter the HOMO energy level of the hole transport layer and the LUMO energy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D491/153C07D209/94C07D209/80H01L51/54C09K11/06
CPCC09K11/06C07D209/80C07D209/94C07D403/10C07D491/153C09K2211/1088C09K2211/1029C09K2211/1007C09K2211/1011H10K85/615H10K85/6574H10K85/6572H10K85/657
Inventor 蔡啸张兆超李崇唐丹丹
Owner VALIANT CO LTD
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