Compound based on disubstituted-9-fluorenone and application thereof

A compound, double substitution technology, applied in organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency, etc. Achieve the effect of reducing efficiency roll-off, good industrialization prospects, improving high exciton utilization rate and high fluorescence radiation efficiency

Active Publication Date: 2017-08-18
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 disubstituted-9-fluorenone and application thereof
  • Compound based on disubstituted-9-fluorenone and application thereof
  • Compound based on disubstituted-9-fluorenone and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Compound 1

[0051]

[0052] In a 250mL three-neck flask, under nitrogen atmosphere, add 0.01mol (3.38g) 2,7-dibromo-9-fluorenone, 0.025mol (4.58g) compound M1, 0.03mol (2.88g) tert-butanol Sodium, 10 -4 mol(0.073g)Pd(dppf)Cl 2 , 180mL toluene, heated to reflux for 8 hours, sampled and plated, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained with a purity of 99% and a yield of 87%.

[0053] Elemental analysis structure (molecular formula C37H22N2O3): Theoretical value C, 81.90; H, 4.09; N, 5.16; O, 8.85 Test value: C, 81.98; H, 4.05; N, 5.08; O, 8.89.

[0054] HPLC-MS: The theoretical molecular weight of the material is 542.16, and the actual molecular weight is 542.49.

Embodiment 2

[0055] Example 2 Compound 2

[0056]

[0057] In a 250mL three-neck flask, under nitrogen atmosphere, add 0.01mol (3.38g) 2,7-dibromo-9-fluorenone, 0.025mol (5.83g) compound M2, 0.03mol (2.88g) tert-butanol Sodium, 10 -4 mol(0.073g)Pd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , to obtain the target product with a purity of 98% and a yield of 75%.

[0058] Elemental analysis structure (molecular formula C45H26N2O3): theoretical value C, 84.10; H, 4.08; N, 4.36; O, 7.47 test value: C, 84.13; H, 4.05; N, 4.33;

[0059] HPLC-MS: The theoretical molecular weight of the material is 642.19, and the actual molecular weight is 642.66.

Embodiment 3

[0060] Example 3 Compound 3

[0061]

[0062] In a 250mL three-neck flask, under nitrogen atmosphere, add 0.01mol (3.38g) 2,7-dibromo-9-fluorenone, 0.025mol (5.83g) compound M3, 0.03mol (2.88g) tert-butanol Sodium, 10 -4 mol(0.073g)Pd(dppf)Cl 2 , 180mL of toluene, heated to reflux for 10 hours, sampling point plate, the reaction was complete; naturally cooled, filtered, the filtrate was collected and subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography was carried out to obtain the target product with a purity of 99%. Yield 77%.

[0063] Elemental analysis structure (molecular formula C45H26N2O3): theoretical value C, 84.10; H, 4.08; N, 4.36; O, 7.47 test value: C, 84.09; H, 4.07; N, 4.33;

[0064] HPLC-MS: The theoretical molecular weight of the material is 642.19, and the actual molecular weight is 642.68.

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Abstract

The invention discloses a compound based on disubstituted-9-fluorenone and application thereof. The compound takes disubstituted-9-fluorenone as a mother nucleus, and two sides of disubstituted-9-fluorenone are connected with two aromatic heterocyclic groups, so that the crystallization of molecules is destroyed, aggregation between the molecules is avoided, and excellent film forming property is achieved. When applied to an OLED as a luminescent layer material, the compound has favorable photoelectric property.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a disubstituent-9-fluorenone and its application as a light-emitting layer material in an organic light-emitting diode. 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D221/18C07D241/46C07D265/34C07D265/38C07D279/22C07D279/36C07D293/10C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D221/18C07D241/46C07D265/34C07D265/38C07D279/22C07D279/36C07D293/10C07D519/00C09K2211/1037C09K2211/104C09K2211/1029C09K2211/1033H10K85/626H10K85/615H10K85/6572H10K85/657
Inventor 巨成良石宇刘英瑞
Owner JIANGSU SUNERA TECH CO LTD
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