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Compound based on 1,8-diazafluoren-9-one and application of compound

A compound, diaza technology, applied to compounds containing 1,8-diaza-9-fluorenone, the application field of organic electroluminescent devices, can solve the problem of efficiency roll-off, low S1 state radiation transition rate , Difficult exciton utilization and high fluorescence radiation efficiency, etc., to achieve the effect of increasing orbital overlap, good industrialization prospects, and avoiding aggregation

Active Publication Date: 2016-12-07
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 1,8-diazafluoren-9-one and application of compound
  • Compound based on 1,8-diazafluoren-9-one and application of compound
  • Compound based on 1,8-diazafluoren-9-one and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Compound 1

[0052] The concrete synthetic route of this compound is provided now:

[0053]

[0054] Add 0.01mol 3,6-dibromo-1,8-diaza-9-fluorenone, 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 99.2% and a yield of 75.00%.

[0055] Elemental analysis structure (molecular formula C 35 h 20 N 4 o 3 ): theoretical value C, 77.20; H, 3.70; N, 10.29; O, 8.81; test value: C, 77.29;

[0056] HPLC-MS: The molecular weight of the material is 544.15, and the measured molecular weight is 544.62.

Embodiment 2

[0057] Example 2 Compound 4

[0058]

[0059] The preparation method of compound 4 is the same as that of Example 1, except that the raw material 9,10-dihydro-9,9-dimethylacridine is used instead of 10H-phenoxazine.

Embodiment 3

[0060] Example 3 Compound 7

[0061] The concrete synthetic route of this compound is provided now:

[0062]

[0063] In a 250ml four-necked flask, add 0.01mol 3,6-bis-(4-bromophenyl)-1,8-diaza-9-fluorenone, 0.025mol 5-phenyl -10-hydrophenazine, 0.03mol sodium tert-butoxide, 1×10 -4 molPd 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 99.5% and a yield of 72.00%.

[0064] Elemental analysis structure (molecular formula C 59 h 38 N 6 O): theoretical value C, 83.67; H, 4.52; N, 9.92; O, 1.89; tested value: C, 83.73; H, 4.39; N, 9.90;

[0065] HPLC-MS: The molecular weight of the material is 846.31, and the measured molecular weight is 846.40.

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Abstract

The invention discloses a compound based on 1,8-diazafluoren-9-one and an application of the compound. According to the compound, the 1,8-diazafluoren-9-one is used as a mother nuclide, and two aromatic heterocyclic groups are connected to two sides of the 1,8-diazafluoren-9-one, so that crystallinity of molecules is destroyed, aggregation between the molecules is avoided, and good film forming performance is obtained. The compound disclosed by the invention is used as a luminescent layer material to be applied to an organic electroluminescent device, and the organic electroluminescent device applying the compound has favorable photoelectric properties and can meet requirements of panel manufacturing enterprises.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing 1,8-diaza-9-fluorenone 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 ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1044C09K2211/104C09K2211/1096C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1037C09K2211/1033H10K85/615H10K85/657H10K85/6572H10K50/00
Inventor 李崇徐凯张兆超
Owner JIANGSU SUNERA TECH CO LTD
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