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Compound based on xanthone and application thereof

A technology of xanthones and compounds, applied in 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. problem, to achieve the effect of improving high exciton utilization rate and high fluorescence radiation efficiency, good industrialization prospects, and reducing efficiency roll-off

Active Publication Date: 2016-12-14
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 based on xanthone and application thereof
  • Compound based on xanthone and application thereof
  • Compound based on xanthone and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Compound C01

[0045]

[0046] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 3-(4-bromophenyl)-xanthone, 0.02mol compound A1, 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, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.56% and a yield of 57%.

[0047] Elemental analysis structure (molecular formula C 40 h 27 NO 3 ): Theoretical value: C, 84.34; H, 4.78; N, 2.46; O, 8.43 Tested value: C, 84.39; H, 4.80; N, 2.46;

[0048] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 40 h 27 NO 3 , theoretical value: 569.20, test value: 569.64.

Embodiment 2

[0049] Example 2 Compound C02

[0050]

[0051] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 3-(3-bromophenyl)-xanthone, 0.02mol compound A1, 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, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.326% and a yield of 48%.

[0052] Elemental analysis structure (molecular formula C 40 h 27 NO 3 ): Theoretical value: C, 84.34; H, 4.78; N, 2.46; O, 8.43 Test value: C, 84.45; H, 4.71; N, 2.52;

[0053] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 40 h 27 NO 3 , theoretical value: 569.20, test value: 569.68.

Embodiment 3

[0054] Example 3 Compound C07

[0055]

[0056] In a 250ml three-neck flask, under nitrogen atmosphere, add 0.01mol 3-(4-bromonaphthalene-1-yl)-xanthone, 0.02mol compound A2, 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, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.6% and a yield of 45%.

[0057] Elemental analysis structure (molecular formula C 44 h 29 NO 3 ): Theoretical value: C,85.28; H,4.72; N,2.26; O,7.75 Tested value: C,85.34; H,4.80; N,2.36; O,7.50.

[0058] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 44 h 29 NO 3 , theoretical value: 619.21, test value: 619.71.

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Abstract

The invention discloses a compound based on xanthone and application thereof. The compound uses xanthone as a parent nucleus, which is connected to a heteroaromatic group, so as to destroy the molecular symmetry, and thus further destroy the crystallinity of molecules and avoid the aggregation between molecules. The compound based on xanthone has good film-forming property, and can be applied to organic light emitting diode as a luminescent layer; and the OLED device using the compound based on xanthone has good photoelectric property, 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 xanthone-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 tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D471/04C07D487/04C07D413/04C07D413/10C07D498/04C07D491/056C07D405/04C07D405/10C07D491/153C07D471/06C07D498/06C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D405/04C07D405/10C07D413/04C07D413/10C07D471/04C07D471/06C07D487/04C07D491/048C07D491/056C07D491/153C07D498/04C07D498/06C07D519/00C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088H10K85/615H10K85/657H10K85/6572H10K85/6574
Inventor 王元勋迟鹏利石宇
Owner JIANGSU SUNERA TECH CO LTD
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