Compound containing anthrone and azacycle and application of compound to OLED

A compound, nitrogen heterocycle technology, applied in the field of compounds containing anthrone and nitrogen heterocycle, can solve different problems

Pending Publication Date: 2020-04-07
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compound containing anthrone and azacycle and application of compound to OLED
  • Compound containing anthrone and azacycle and application of compound to OLED
  • Compound containing anthrone and azacycle and application of compound to OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The synthesis of embodiment 1 intermediate M:

[0082]

[0083] (1) Under a nitrogen atmosphere, weigh raw material B and dissolve it in tetrahydrofuran, then add raw material C and tetrakis(triphenylphosphine)palladium, stir the mixture, then add potassium carbonate aqueous solution, and mix the above-mentioned reactants at the reaction temperature At 70-90°C, heat to reflux for 5-20 hours. After the reaction, cooling and adding water, the mixture was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, the obtained residue was purified by silica gel column to obtain intermediate I;

[0084] The molar ratio of raw material B to raw material C is 1:1.0~1.5, the molar ratio of tetrakis(triphenylphosphine) palladium to raw material B is 0.001~0.02:1, and the molar ratio of potassium carbonate to raw material B is 1.0~2.0 :1, the ratio of THF dosage to raw material B is 1g:10~30ml.

[00...

Embodiment 2

[0107] The synthesis of embodiment 2 intermediate S and intermediate T:

[0108] When X=O:

[0109]

[0110] Take the synthesis of intermediate S-1 as an example:

[0111]

[0112] The specific reaction process is:

[0113] (1) In a 500mL three-necked flask equipped with a Dean-Stark separator, feed nitrogen, add 0.1mol of raw material A, 0.2mol of potassium carbonate, 125ml of toluene, and 125ml of DMF, stir, reflux for 4 hours, and dehydrate, Until no more water is produced in the system, about 100 mL of toluene is removed by using a Dean-Stark separator. Naturally cooled to room temperature, 0.12 mol of raw material K was added, and the reaction was refluxed under nitrogen atmosphere for 24 hours. After the reaction, add 200ml of toluene to dilute the system, wash the organic phase with water (200mL water) 3 times with a separatory funnel, separate layers, take the organic phase and dry it with anhydrous sodium sulfate, filter, and the filtrate is rotary evaporated...

Embodiment 3

[0121] The synthesis of embodiment 3 intermediate O and intermediate P:

[0122] When Ar 3 and Ar 4 For methyl:

[0123]

[0124] Its specific reaction process is similar to that of intermediate T, except that raw material U is replaced by raw material V

[0125] When Ar 3 and Ar 4 When it is phenyl:

[0126]

[0127] Take the synthesis of intermediate P-1 as an example:

[0128]

[0129] The specific reaction process is:

[0130] (1) Under a nitrogen atmosphere, first dissolve 0.2 mol of raw material W in 200 ml of tetrahydrofuran, then add the freshly prepared tetrahydrofuran solution of Grignard reagent phenylmagnesium bromide dropwise to the reaction system, and react under reflux for 3 hours. to room temperature. Then the reaction mixture was slowly poured into dilute hydrochloric acid with a mass concentration of 10%, stirred for 15 minutes, separated, the organic phase was collected, dried, and the crude intermediate F obtained by rotary evaporation was...

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Abstract

The invention discloses a compound containing anthrone and azacycle and an application of the compound to an OLED. The compound contains anthrone and azacycle structures; anthrone and azacycle are both strong electron groups, and have deep HOMO energy level and high electron mobility, so that the compound is suitable for being used as a hole blocking material or an electron transport material, andcan also be used as a luminescent layer host material; besides, the compound is high in rigidity and has the characteristics of being not prone to crystallization and aggregation among molecules andgood in film-forming property, and after the compound serves as an organic electroluminescence functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing anthrone and nitrogen heterocycle and its application in OLED. 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. 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 of the OLED light-emitting device, and the positive and negative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C07D251/24C07D403/10C07D405/14C07D401/14C07D471/04C07D417/14C07D213/50C07D403/04C07D239/26C07D239/28C07D213/85C07D413/14C07D409/10C09K11/06H01L51/50H01L51/54
CPCC07D405/10C07D251/24C07D403/10C07D405/14C07D401/14C07D471/04C07D417/14C07D213/50C07D403/04C07D239/26C07D239/28C07D213/85C07D413/14C07D409/10C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/18H10K50/16H10K50/11
Inventor 殷梦轩李崇王芳谢丹丹
Owner JIANGSU SUNERA TECH CO LTD
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