Compound with ketone as core, preparation method and application of compound

A compound and general formula technology, applied in the application field of organic electroluminescent devices, can solve difficult problems such as high exciton utilization rate and high fluorescence radiation efficiency, low S1 state radiation transition rate, efficiency roll-off, etc.

Inactive Publication Date: 2019-10-29
JIANGSU SUNERA TECH 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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  • Compound with ketone as core, preparation method and application of compound
  • Compound with ketone as core, preparation method and application of compound
  • Compound with ketone as core, preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0191] Example 1 Preparation of Compound 1

[0192] Preparation of intermediate A1

[0193]

[0194] In a 250mL three-necked flask, blow nitrogen, add 0.01mol of raw material M-1, 0.012mol of raw material N-1, 150mL of toluene and ethanol mixed solvent (including toluene 100mL, ethanol 50mL), stir and mix, then add 0.02mol potassium carbonate Solution (2M), 1×10 -4 molPd(PPh 3 ) 4 , Heating to 120℃, refluxing reaction for 24h, sampling point plate, showing that no bromine is left, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85℃), and passed through a neutral silica gel column , To obtain intermediate I-1;

[0195] Dissolve 0.01 mol of intermediate I-1 in 100 mL of o-dichlorobenzene, add triphenylphosphine, react at 180°C for 12-24 hours, cool to room temperature after the reaction, filter, spin-evaporate the filtrate, and pass through a silica gel column to obtain Intermediate A1.

[019...

Embodiment 3

[0210] Example 3 Preparation of Compound 55

[0211] Preparation of intermediate C1

[0212]

[0213] In a 250mL three-necked flask, blow nitrogen, add 0.01mol intermediate A1, 0.012mol raw material K1, 150mL toluene, stir and mix, and then add 6×10 -5 mol Pd 2 (dba) 3 , 6×10 -5 mol of triphenylphosphine, 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 24h, sampling point plate showed that no bromide remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated to no distillate. Neutral silica gel column to obtain intermediate IIIx;

[0214] Under the protection of nitrogen, 0.01mol intermediate IIIx, 0.0075mol bis(pinacol) diboron, 0.0005molPd(dppf)Cl 2 , 0.025mol potassium acetate was dissolved in toluene, reacted at 105°C for 24h, sampling point plate, reaction was complete, natural cooling, filtration, and filtrate rotary evaporation to obtain crude product, pass through neutral silica gel column to ...

Embodiment 5

[0226] Example 5 Preparation of Compound 219

[0227]

[0228] The preparation method of compound 219 is the same as that of Example 2, except that intermediate A3 is substituted for intermediate A2. Elemental analysis structure (molecular formula C 33 H 17 N 3 O 3 ): Theoretical value: C, 78.72; H, 3.40; N, 8.35; O, 9.53; Test value: C, 78.72; H, 3.41; N, 8.35; O, 9.52. ESI-MS (m / z) (M+): The theoretical value is 503.52, and the measured value is 503.50.

[0229] The preparation process of Example 5 was repeated, and the following compounds were prepared through Examples 6-25, except that the raw materials I and Intermediate A listed in Table 9 below were used:

[0230] Table 9

[0231]

[0232]

[0233]

[0234]

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PUM

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Abstract

The invention discloses a compound with ketone as the core, a preparation method and application of the compound. The compound has small delta Est, reverse interstitial leaping of energy is facilitated, and the compound has a high triplet state energy level (T1) and appropriate HOMO and LUMO energy levels, and is suitable for being used as a main material of a luminescent layer of an organic electroluminescence device; and in addition, the compound has the strong group rigidity, and has the characteristics of difficult crystallization and difficult aggregation among molecules and good film formation. The compound is applied to an OLED device as an organic electroluminescence functional layer material, the current efficiency, the power efficiency and the external quantum efficiency of the device are all greatly improved, and meanwhile, the service life of the device is obviously prolonged.

Description

Technical field [0001] The present invention relates to the field of semiconductor technology, in particular to a compound with a ketone as the core, a preparation method of the compound and its application in organic electroluminescence devices. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and its application prospects are very broad. [0003] However, traditional organic fluorescent materials can only emit light with 25% singlet excitons formed by electrical excitation, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, which is far behind the efficiency of phosphorescent devices. Although the phosphorescent material enhances the intersystem crossing due to the strong spin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/54
CPCC07D519/00H10K85/636H10K85/654H10K85/657
Inventor 吴秀芹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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