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Five-membered ring substituted compound with xanthone as core and use thereof

A technology of xanthone and compound, applied in the field of semiconductor, can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, 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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  • Five-membered ring substituted compound with xanthone as core and use thereof
  • Five-membered ring substituted compound with xanthone as core and use thereof
  • Five-membered ring substituted compound with xanthone as core and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1 Synthesis of compound C03

[0065]

[0066] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015mol compound A1, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 99.70% and a yield of 42.10%.

[0067] HPLC-MS: The molecular weight of the material is 694.23, and the measured molecular weight is 694.26.

Embodiment 2

[0068] Example 2 Synthesis of Compound C05

[0069]

[0070] In a 250ml four-neck flask, add 0.01mol 2-bromo-xanthone, 0.015molA2, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.60% and a yield of 56.20%.

[0071] HPLC-MS: The molecular weight of the material is 644.25, and the measured molecular weight is 644.32.

Embodiment 3

[0072] Example 3 Synthesis of Compound C11

[0073]

[0074] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015molA3, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.20% and a yield of 42.30%.

[0075] HPLC-MS: The molecular weight of the material is 811.32, and the measured molecular weight is 811.46.

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Abstract

The invention discloses a five-membered ring substituted compound with xanthone as a core and a use thereof. According to the compound, xanthone 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 present invention relates to the field of semiconductor technology, in particular to a xanthone-based compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat panel display product at home and abroad. This is because OLED displays have self-luminous, wide viewing angle (up to 175°), short response time, high luminous efficiency, and wide color. Domain, low working voltage (3~10V), thin panel (can be less than 1mm) and rollable characteristics. OLED is hailed as the star flat display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and the future is limitless. [0003] The principle of OLED light emission is by applying an external voltage. After holes and electrons overcome the interface barrier, they are injec...

Claims

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Application Information

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IPC IPC(8): C07D209/80C07D311/86C07D405/04C07D405/10C07D405/12C07D405/14C07D407/04C07D407/10C07D407/14C07D409/04C07D409/12C07D409/14C07D413/10C07D413/14C07D471/04C07D487/04C07D491/048C07D491/056C07D493/04C07D495/04C07D498/04H01L51/54
CPCC07D209/80C07D311/86C07D405/04C07D405/10C07D405/12C07D405/14C07D407/04C07D407/10C07D407/14C07D409/04C07D409/12C07D409/14C07D413/10C07D413/14C07D471/04C07D487/04C07D491/048C07D491/056C07D493/04C07D495/04C07D498/04H10K85/636H10K85/6576H10K85/6574H10K85/657H10K85/6572C09K11/06
Inventor 徐凯陈棪李崇张兆超叶中华张小庆王立春
Owner JIANGSU SUNERA TECH CO LTD
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