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Ketone structure-cored organic compound and application thereof to OLED (organic light emitting diode) devices

An organic compound and compound technology, applied to the application of organic light-emitting diodes, based on the compound field of ketone structure, can solve the problem of efficiency roll-off, difficult exciton utilization rate and high fluorescence radiation efficiency, low S1 state radiation transition rate, etc. problems, to achieve the effect of increasing orbital overlap, avoiding aggregation, and good industrialization prospects

Inactive Publication Date: 2019-04-05
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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  • Ketone structure-cored organic compound and application thereof to OLED (organic light emitting diode) devices
  • Ketone structure-cored organic compound and application thereof to OLED (organic light emitting diode) devices
  • Ketone structure-cored organic compound and application thereof to OLED (organic light emitting diode) devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of Example 1 Intermediate B

[0064]

[0065] Under nitrogen atmosphere, weigh raw material I and dissolve it in tetrahydrofuran, then add raw material III and tetrakis(triphenylphosphine) palladium, stir the mixture, add potassium carbonate aqueous solution again, and keep the mixed solution of the above reactants at a reaction temperature of 70- At 90°C, heat under reflux for 5-20 hours. After the reaction was completed, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and the obtained residue was purified by silica gel column to obtain Intermediate B;

[0066] The molar ratio of raw material I to raw material III is 1:1.0 to 1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to intermediate II is 0.001 to 0.02:1, and the molar ratio of potassium carbonate to raw material I is 1.0 to 2.0: 1. The ratio of tetrahydrofu...

Embodiment 2

[0074] The synthesis of embodiment 2 compound C01

[0075]

[0076] A 250ml four-necked bottle, in a nitrogen atmosphere, add 0.01mol 2-bromo-10,10-dimethyl-10H-anthrone, 0.015mol A1, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1 × 10 -4 mol tri-tert-butylphosphine, 150 ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete, naturally cooled, filtered, the filtrate was rotary evaporated, passed through a silica gel column to obtain the target product with a purity of 99.40% and a yield of 46.90%.

[0077] Elemental analysis structure (molecular formula C 40 H 28 N 2 O): Theoretical C, 86.93; H, 5.11; N, 5.07; O, 2.89; Tested: C, 86.95; H, 5.09; N, 5.09; O, 2.87. ESI-MS(m / z)(M + ): The theoretical value is 522.22, and the measured molecular weight is 522.24.

Embodiment 3

[0078] The synthesis of embodiment 3 compound C05

[0079]

[0080] A 250ml four-necked bottle, in a nitrogen atmosphere, add 0.01mol 2-bromo-10,10-dimethyl-10H-anthrone, 0.015mol A2, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1 × 10 -4 mol tri-tert-butylphosphine, 150 ml of toluene, heated to reflux for 24 hours, sampled 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 97.62% and a yield of 50.82%.

[0081] Elemental analysis structure (molecular formula C 34 H 23 NO 2 ): Theoretical C, 85.51; H, 5.11; N, 5.07; O, 2.89; Tested: C, 85.51; H, 4.85; N, 2.93; O, 6.70. ESI-MS(m / z)(M + ): The theoretical value is 477.17, and the measured molecular weight is 477.19.

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Abstract

The invention discloses a ketone structure-cored organic compound and application thereof to organic light emitting devices. The ketone structure-cored organic compound is characterized in that deltaEst<0.2eV, and 2.7 eV<T1<3.0 eV; when connected with heteroaromatic groups, the ketone structure-cored organic compound can break molecular symmetry to break molecular crystallization property, avoidintermolecular aggregation and accordingly achieve good film-forming performance. The ketone structure-cored organic compound can be applied to organic light emitting diodes as a luminescent layer material; OLED devices with the ketone structure-cored organic compound can achieve high photoelectric properties and meet the demands of panel manufacturers.

Description

technical field [0001] The present invention relates to the technical field of semiconductors, in particular to a compound based on a ketone structure and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat panel display product at home and abroad, because OLED display has self-luminous, wide viewing angle (over 175°), short response time, high luminous efficiency, wide color Domain, low operating voltage (3 ~ 10V), thin panel (can be less than 1mm) and can be rolled and other characteristics. OLED has been hailed as the star flat display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and the future is boundless. [0003] The principle of OLED light emission is that by applying an external voltage, holes and electrons are injected from ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D209/94C07D221/18C07D405/04C07D405/10C07D471/04C07D487/04C07D491/048C07D491/153C07D495/04C09K11/06H01L51/54
CPCC09K11/06C07D209/80C07D209/94C07D221/18C07D405/04C07D405/10C07D471/04C07D487/04C07D491/048C07D491/153C07D495/04C09K2211/1029C09K2211/1092C09K2211/1088H10K85/631H10K85/636H10K85/657H10K85/6574H10K85/6572
Inventor 蔡啸唐丹丹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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