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Bis-carbazole pyridine compound and applications thereof

A biscarbazolpyridine and compound technology, applied in the field of organic electroluminescent materials, can solve the problems of low triplet energy level, insufficient glass transition temperature, poor thermal stability, etc., and achieve good luminescence performance, long device life, and reaction The effect of simple steps

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

[0006] However, the common host materials in the prior art generally have insufficient glass transition temperature, poor thermal stability, and low triplet energy level. Therefore, it is urgent to develop phosphorescent materials with higher thermal stability and triplet energy level. Compound host material

Method used

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  • Bis-carbazole pyridine compound and applications thereof
  • Bis-carbazole pyridine compound and applications thereof
  • Bis-carbazole pyridine compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114]

[0115] 2,6-Difluoro-4-bromopyridine (1.93g, 10mmol) and carbazole (3.7g, 22mmol) were added to a round bottom flask, and then potassium tert-butoxide (2.46g, 22mmol), N-methyl Pyrrolidone 20mL, 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, mix the sample with silica gel and pass through the column . 2.3 g of solid intermediate (M-1) were obtained.

[0116]

[0117] 9,9-dihydrofluorene (1mmol), intermediate (M-1) (2mmol), potassium tert-butoxide (2mmol), palladium acetate (5mol%), tricyclohexylphosphine (10mol%), anhydrous toluene 50mL, reacted at 80°C for 24 hours, cooled to room temperature, separated and extracted three times with dichloromethane, combined the organic phase, dried and concentrated the organic phase, mixed with silica gel and passed through the column ...

Embodiment 2

[0119]

[0120] Compound (X-2) (1mmol), intermediate (M-1) (2mmol), potassium tert-butoxide (2mmol), palladium acetate (5mol%), tricyclohexylphosphine (10mol%), anhydrous toluene 50mL , reacted at 80°C for 24 hours, cooled to room temperature, separated and extracted three times with dichloromethane, combined the organic phases, dried and concentrated the organic phases, mixed with silica gel and passed through the column to obtain 0.33 g of compound (A-3).

[0121] 1H NMR (400MHz, Solvent: DMSO-d6) δppm: 8.53(2H), 8.36(8H), 7.64(2H), 7.44-7.38(8H), 7.33-7.24(22H).

[0122]

Embodiment 3

[0124]

[0125] Compound (X-3) (1mmol), intermediate (M-1) (2mmol), potassium tert-butoxide (2mmol), palladium acetate (5mol%), tricyclohexylphosphine (10mol%), anhydrous toluene 50mL , reacted at 80°C for 24 hours, cooled to room temperature, separated and extracted three times with dichloromethane, combined the organic phase, concentrated the organic phase after drying, mixed the sample with silica gel and passed through the column to obtain 0.43 g of compound (B-1).

[0126] 1H NMR (400MHz, Solvent: DMSO-d6) δppm: 8.37(8H), 7.54(2H), 7.41(8H), 7.33-7.24(22H), 7.14(2H), 7.04(2H).

[0127]

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a bis-carbazole pyridine compound and applications thereof. The provided compound has a structure representedby the formula (I), has a high triplet energy level, and can be used as a host material of a phosphorescence organic light emitting device (OLED), in particular, a blue phosphorescence OLED. Comparedwith a 2,6-bicarbazole pyridine host material commonly used in the field, a device prepared from provided bis-carbazole pyridine compound has a good light emitting performance and a long service lifeand can be used in industry.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a biscarbazolpyridine 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. Examples of common host materials include CBP, and examples...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D471/04C07D405/14C07D409/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D405/14C07D409/14C07D471/04C07F7/08C09K2211/1011C09K2211/1029C09K2211/1007C09K2211/1092C09K2211/1088H10K85/622H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/40H10K50/11
Inventor 黄达
Owner AAC TECH NANJING
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