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Dual-substituent-group-9-fluorenone compound-containing organic light-emitting device and application thereof

A technology of electroluminescent devices and compounds, applied in the field of organic electroluminescent devices, can solve the problems of high exciton utilization rate, high fluorescence radiation efficiency, efficiency roll-off, low S1 state radiation transition rate, etc., and achieve high efficiency , the effect of small energy gap difference

Active Publication Date: 2017-08-15
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) The T1 and S1 states of the designed molecule have strong CT features and a very small S1-T1 state energy gap, although high T can be achieved through the TADF process 1 →S 1 State exciton conversion rate, but at the same time lead to low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization rate and high fluorescence radiation efficiency;
[0007] (2) Even if doped devices have been used to alleviate the T-exciton concentration quenching effect, the efficiency of most TADF materials has a serious roll-off at high current densities.

Method used

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  • Dual-substituent-group-9-fluorenone compound-containing organic light-emitting device and application thereof
  • Dual-substituent-group-9-fluorenone compound-containing organic light-emitting device and application thereof
  • Dual-substituent-group-9-fluorenone compound-containing organic light-emitting device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 Compound 1

[0060]

[0061] 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%.

[0062] 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.

[0063] HPLC-MS: The theoretical molecular weight of the material is 542.16, and the actual molecular weight is 542.49.

Embodiment 2

[0064] Example 2 Compound 2

[0065]

[0066] 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%.

[0067] 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;

[0068] HPLC-MS: The theoretical molecular weight of the material is 642.19, and the actual molecular weight is 642.66.

Embodiment 3

[0069] Example 3 Compound 3

[0070]

[0071] 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%.

[0072] 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;

[0073] 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 dual-substituent-group-9-fluorenone compound-containing organic light-emitting device and an application thereof. The device comprises a hole transport layer, a light emitting layer and an electron transfer layer; the light emitting layer of the device adopts the material of the dual-substituent-group-9-fluorenone-group-containing compound which is as shown in the general formula (1). The adopted dual-substituent-group-9-fluorenone-group compound has relatively low triplet state and singlet state energy difference, so that energy transfer between host-guest materials can be realized easily; therefore, energy which is originally dissipated in a heat form can be obtained and utilized easily, thereby obtaining high efficiency of a device more easily; and furthermore, when a fluorescent material is selected as a doping material, the light emitting radiation of the doping material can be obtained more easily, thereby achieving long service life of the material more easily.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic electroluminescence device in which the light-emitting layer material is a disubstituent-9-fluorenone compound and an application thereof. 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 b...

Claims

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Application Information

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IPC IPC(8): H01L51/50H01L51/54C09K11/06H01L27/32
CPCC09K11/06C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1037C09K2211/1033H10K59/12H10K85/60H10K50/11H10K2102/3026
Inventor 李崇张兆超王立春
Owner JIANGSU SUNERA TECH CO LTD
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