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Carbazole pyridine compound and applications thereof

A technology of carbazolpyridine and compounds, which is applied in the field of organic electroluminescent materials, can solve the problems of low triplet energy level, poor thermal stability, and insufficient glass transition temperature, and achieve long device life and good luminescent performance.

Inactive Publication Date: 2019-04-19
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, currently commonly used host materials in this field generally have insufficient glass transition temperature, poor thermal stability, and low triplet energy level. Therefore, it is urgent to develop phosphorescent compounds with higher thermal stability and triplet energy level. main material

Method used

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  • Carbazole pyridine compound and applications thereof
  • Carbazole pyridine compound and applications thereof
  • Carbazole pyridine compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: the synthesis of compound (A-4)

[0086]

[0087] 2,6-Dibromo-pyridine (2.35g, 10mmol) and carbazole (3.7g, 22mmol) were added to a round bottom flask, then 0.5g of cuprous iodide, 0.5g of cyclohexanediamine, anhydrous phosphoric acid Potassium 8.3g, toluene 200mL, after evacuating nitrogen, heat up to 110 degrees, react for 24 hours, cool to room temperature, add 100mL water, dichloromethane separate liquid extraction three times, combine the organic phase, concentrate the organic phase after drying, and mix with silica gel Sample through the column. 2.9 g of solid intermediate (M-1) were obtained.

[0088]

[0089] Add intermediate (M-1) (0.41g, 1mmol), acetone (0.03g, 0.5mmol), hydrogen fluoride (0.2g 10mmol) into the sealed tube, replace the air in the glove box, heat to 130 degrees, and react for 24 hours , after cooling, the mixture was added to water, separated and extracted three times with dichloromethane, the organic phases were combined,...

Embodiment 2

[0091] Embodiment 2: the synthesis of compound (A-5)

[0092]

[0093] Add 2,6-dibromo-4-fluoro-pyridine (2.53g, 10mmol) and carbazole (3.7g, 22mmol) into a round bottom flask, then add 0.5g of cuprous iodide and 0.5g of cyclohexanediamine , anhydrous potassium phosphate 8.3g, toluene 200mL, after evacuating nitrogen, heat up to 110 degrees, react for 24 hours, cool to room temperature, add 100mL of water, separate liquid extraction with dichloromethane three times, combine organic phases, dry and concentrate organic phase, the silica gel was mixed and the sample was passed through the column. 2.7 g of solid intermediate (M-2) was obtained.

[0094]

[0095] Add diphenylmethane (0.34g, 2mmol) into 10mL of anhydrous tetrahydrofuran, and add dropwise into the tetrahydrofuran dispersion of sodium hydride (0.24g of sodium hydride, 10mL of tetrahydrofuran) at zero temperature, and stir for 1 hour after the dropwise addition is completed. The tetrahydrofuran solution (M-2, 0...

Embodiment 3

[0099] Embodiment 3: the synthesis of compound (A-6)

[0100]

[0101] The synthesis method is similar to that of Example 2, except that diphenylmethane is replaced by di-p-tolylmethane.

[0102] 1 H NMR (400MHz, Solvent: CDCl3) δppm: 8.12(8H), 7.85(8H), 7.45(8H), 7.35(18H), 7.13(8H), 7.06(4H), 2.30(6H).

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a carbazole pyridine compound and applications thereof. The provided compound has a structure represented by the formula (I). The compound has a high triplet level and can be used as the host material of a phosphorescence organic light emitting device, in particular, a blue light phosphorescence organic lightemitting device. Compared with a 2,6-dicarbazole pyridine host material, which is commonly used in the field, a device prepared from the provided carbazole pyridine compound has a good light emittingperformance, at the same time, the service life of the device is long, and the compound can be used in industry.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a carbazole pyridine compound and its application. Background technique [0002] The use of organic materials to prepare various functional devices, especially for photoelectrically responsive functional devices, such as common organic electroluminescent devices, organic solar cell devices, organic field effect transistor devices and organic photosensitive sensor devices, has attracted more and more attention. . Organic electroluminescence devices have various structures. For the light-emitting layer, host-guest doping can be used to improve device efficiency and lifetime. The host material receives energy and transmits it to the guest, and the guest material emits a corresponding spectrum after receiving the energy. Different host and object materials can achieve different colors of luminescence. The common host material in this field is CBP, and the commo...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C09K2211/1007C09K2211/1029H10K85/6572H10K50/11
Inventor 黄达
Owner AAC TECH NANJING
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