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Compound with anthrone as core and use thereof

A compound, anthrone technology, applied in the fields of organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of difficult exciton utilization, high fluorescence radiation efficiency, low S1 state radiation transition rate, efficiency roll-off, etc.

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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  • Compound with anthrone as core and use thereof
  • Compound with anthrone as core and use thereof
  • Compound with anthrone as core and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] The synthesis of embodiment 1 compound C02

[0066]

[0067] In a 250ml four-neck flask, add 0.01mol 3-(4-bromophenyl)-10,10-dimethyl-10H-anthrone, 0.015mol compound A1, 0.03mol tert-butanol under nitrogen atmosphere Sodium, 1 x 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 98.28% and a yield of 56.55%.

[0068] HPLC-MS: The molecular weight of the material is 628.25, and the measured molecular weight is 628.29.

Embodiment 2

[0069] The synthesis of embodiment 2 compound C07

[0070]

[0071] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-(3-bromophenyl)-10,10-dimethyl-10H-anthrone, 0.015molA2, 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 97.58% and a yield of 45.61%.

[0072] HPLC-MS: The molecular weight of the material is 579.26, and the measured molecular weight is 579.31.

Embodiment 3

[0073] The synthesis of embodiment 3 compound C11

[0074]

[0075] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 3-bromo-10,10-dimethyl-10H-anthrone, 0.015molA3, 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 97.49% and a yield of 46.2%.

[0076] HPLC-MS: The molecular weight of the material is 567.18, and the measured molecular weight is 567.21.

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Abstract

The invention discloses a compound with anthrone as a core and a use thereof. According to the compound, anthrone is a mother nucleus and is connected to an aromatic heterocyclic group so that molecular symmetry is destroyed, molecule crystallinity is destroyed, intermolecular aggregation is avoided and good film-forming performances are obtained. The compound as a light-emitting layer material is used for an organic light-emitting diode. An OLED device prepared from the compound has good photoelectric properties and can satisfy the requirements of the panel manufacturing companies.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an anthrone-based compound 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 level of the electron t...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D209/86C07D493/14C07D493/04C07D307/91C07D471/04C07D265/38C07D209/88C07D413/14C07D401/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D209/86C07D209/88C07D265/38C07D307/91C07D401/04C07D413/14C07D471/04C07D487/04C07D493/04C07D493/14C07D519/00C09K11/06C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1029H10K85/656H10K85/654H10K85/657H10K85/6572H10K50/12
Inventor 陈棪李崇徐凯张兆超叶中华张小庆王立春
Owner JIANGSU SUNERA TECH CO LTD
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