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Compound with pyridine as core and application thereof in organic electroluminescence device

A compound, azabenzene technology, applied in the application field of organic electroluminescent devices, can solve the problems of low S1 state radiation transition rate, efficiency roll-off, difficult exciton utilization rate and high fluorescence radiation efficiency, etc. Film formation and fluorescence quantum efficiency, increasing orbital overlap, avoiding the effect of aggregation

Inactive Publication Date: 2016-12-14
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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  • Compound with pyridine as core and application thereof in organic electroluminescence device
  • Compound with pyridine as core and application thereof in organic electroluminescence device
  • Compound with pyridine as core and application thereof in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Compound 1

[0046]

[0047] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,6-dibromo-2-phenyl-pyrimidine, 0.025mol 9,10-dihydro-9,9-dimethylacridine, 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 on a plate, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.2% and a yield of 66.00%.

[0048] Elemental analysis structure (molecular formula C 40 h 34 N 4 ): theoretical value C, 84.18; H, 6.00; N, 9.82; test value: C, 84.19; H, 6.04; N, 9.77.

[0049] HPLC-MS: The molecular weight of the material is 570.28, and the measured molecular weight is 570.80.

Embodiment 2

[0050] Example 2 Compound 2

[0051]

[0052] Add 0.01mol 3-biphenyl-4-yl-2,5-dibromo-pyrazine, 0.025mol 10H-phenoxazine, 0.03mol sodium tert-butoxide to a 250ml four-necked flask under nitrogen atmosphere , 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 plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 96.8% and a yield of 68.30%.

[0053] Elemental analysis structure (molecular formula C 40 h 26 N 4 o 2 : Theoretical value C, 80.79; H, 4.41; N, 9.42; O, 5.38; Test value: C, 80.82; H, 4.40; N, 9.41;

[0054] HPLC-MS: The molecular weight of the material is 594.21, and the measured molecular weight is 594.62.

Embodiment 3

[0055] Example 3 Compound 3

[0056]

[0057] Add 0.01mol 4-biphenyl-4-yl-3,6-dibromo-pyrazine, 0.025mol 10H-phenoxazine, 0.03mol sodium tert-butoxide to a 250ml four-necked flask under nitrogen atmosphere , 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, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 95.0% and a yield of 72.30%.

[0058] Elemental analysis structure (molecular formula C 40 h 26 N 4 o 2 : Theoretical value C, 80.79; H, 4.41; N, 9.42; O, 5.38; Test value: C, 80.80; H, 4.36; N, 9.47;

[0059] HPLC-MS: The molecular weight of the material is 594.21, and the measured molecular weight is 594.69.

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Abstract

The invention discloses a compound with pyridine as a core and application thereof in an organic electroluminescence device. The compound has the advantages that molecules are not prone to crystallization or aggregation and have a good film-forming property. By means of rigid groups in the compound molecules, thermostability of the material can be improved, the compound can be used as a luminescent layer material applied to an OLED, and a manufactured OLED device has high photoelectric property and can meet the requirement of a panel manufacturing enterprise better.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with azabenzene as the core and its application as a light-emitting layer material in an organic electroluminescent device. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D413/14C07D417/14C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D401/14C07D413/14C07D417/14C07D519/00C09K2211/1088C09K2211/1092C09K2211/1037C09K2211/1044C09K2211/1029C09K2211/1033H10K85/653H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 李崇徐凯张兆超
Owner VALIANT CO LTD
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