Benzopyran-4-ketone organic electroluminescence material, as well as preparation method and application of material

A benzopyran and luminescent technology, which is applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of efficiency roll-off, difficult high exciton utilization rate and high fluorescence radiation efficiency, and low S1 state radiative transition Speed ​​and other issues, to achieve the effect of power efficiency and external quantum efficiency improvement, good application effect, and good industrialization prospect

Inactive Publication Date: 2017-05-31
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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 A high T1→S1 state exciton conversion rate is achieved through the TADF process, but at the same time it leads to a low S1 state radiative transition rate. Therefore, it is difficult to achieve both (or simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) even Doped devices have been used to alleviate the T-exciton concentration quenching effect, and most devices made of TADF materials have a serious efficiency roll-off at high current densities

Method used

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  • Benzopyran-4-ketone organic electroluminescence material, as well as preparation method and application of material
  • Benzopyran-4-ketone organic electroluminescence material, as well as preparation method and application of material
  • Benzopyran-4-ketone organic electroluminescence material, as well as preparation method and application of material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Compound C05

[0045]

[0046] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 6-bromo-7-methyl-benzopyran-4-one, 0.02mol compound A1, 0.03mol sodium tert-butoxide, 1×10- 4mol Pd 2 (dba) 3 , 1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated and refluxed for 24 hours, sampled and spotted, cooled naturally, 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 34 h 22 N 2 o 2 ): Theoretical value: C,83.25; H,4.52; N,5.71; O,6.52 Tested value: C,83.29; H,4.52; N,5.66; O,6.53.

[0048] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 34 h 22 N 2 o 2 , theoretical value: 490.1681, test value: 490.1683.

Embodiment 2

[0049] Example 2 Compound C08

[0050]

[0051] In a 250ml three-neck flask, add 0.01mol 6-(4-bromophenyl)-7-methyl-chromen-4-one, 0.02mol compound A2, 0.03mol tert-butanol under nitrogen atmosphere Sodium, 1×10-4mol Pd 2 (dba) 3 , 1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampled and spot plated, cooled naturally, 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 37 h 27 NO 2 ): Theoretical value: C, 85.85; H, 5.26; N, 2.71; Test value: C, 85.75; H, 5.23; N, 2.73.

[0053] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 37 h 23 NO 2 , theoretical value: 517.2042, test value: 517.2046.

Embodiment 3

[0054] Example 3 Compound C19

[0055]

[0056] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 6-bromo-7-methyl-benzopyran-4-one, 0.02mol compound A3, 0.03mol sodium tert-butoxide, 1×10- 4mol Pd 2 (dba) 3 , 1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampled and spotted, cooled naturally, 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 34 h 19 NO 4 ): Theoretical value: C, 80.78; H, 3.79; N, 2.77; O, 12.66 Test value: C, 80.74; H, 3.80; N, 2.78;

[0058] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 34 h 19 NO 4 , theoretical value: 505.1314, test value: 505.1318.

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Abstract

The invention discloses a benzopyran-4-ketone organic electroluminescence material, as well as a preparation method and application of the material. A structural formula of the organic electroluminescence material is as shown in description. The benzopyran-4-ketone organic electroluminescence material provided by the invention is applied to an OLED luminescent device, so that the current efficiency, power efficiency and outer quantum efficiency of the device are greatly improved. The benzopyran-4-ketone organic electroluminescence material provided by the invention has a good application effect and good industrialized prospect.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to a benzopyran-4-one organic electroluminescent material and a preparation method and application thereof. 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. 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. 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 transport layer respectively; Driven by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D495/04C07D487/04C07D491/048C07D209/94C07D491/153C07D491/147C07D487/14C07D491/056C07D498/04C07D413/04C07D471/04C07D498/14C07D513/14C07D487/06C07D498/06C07D405/10C09K11/06H01L51/54
CPCC09K11/06C07D209/94C07D405/04C07D405/10C07D413/04C07D471/04C07D487/04C07D487/06C07D487/14C07D491/048C07D491/056C07D491/147C07D491/153C07D495/04C07D498/04C07D498/06C07D498/14C07D513/14C09K2211/1088C09K2211/1044C09K2211/1033C09K2211/1029H10K85/6574H10K85/6572H10K85/657
Inventor 王元勋石宇高自良巨成良胡葆华孙利
Owner VALIANT CO LTD
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