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Compound with aza-spirofluorene structure as mother nucleus and application of compound on organic electroluminescent devices

A compound and organic compound technology, applied in the application field of organic electroluminescent devices, can solve problems such as performance differences

Inactive Publication Date: 2019-07-02
VALIANT 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 with aza-spirofluorene structure as mother nucleus and application of compound on organic electroluminescent devices
  • Compound with aza-spirofluorene structure as mother nucleus and application of compound on organic electroluminescent devices
  • Compound with aza-spirofluorene structure as mother nucleus and application of compound on organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of compound 1

[0054]

[0055] In a 500mL three-neck flask, under nitrogen protection, add 0.03mol raw material A-1, 0.03mol raw material B-1, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide and 0.09mol triphenylphosphine, 0.0015mol Pd 2 (dba) 3 , heated to 110°C, reflux reaction for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain compound 1. The HPLC purity was 99.3%, and the yield was 76.3%;

[0056] Elemental analysis structure (molecular formula C 44 h 29 N 3 O): theoretical value C, 85.83; H, 4.75; N, 6.82; tested value: C, 85.81; H, 4.76; N, 6.81. MS m / z: 615.28[M+H] + , theoretical value: 615.74.

Embodiment 2

[0057] Embodiment 2: the synthesis of compound 15

[0058]

[0059]

[0060] In a 500mL three-neck flask, under nitrogen protection, add 0.03mol raw material B-2, 0.03mol p-dibromobenzene, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide and 0.09mol triphenylphosphine, 0.0015mol Pd 2 (dba) 3 , heated to 110°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced-pressure rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate C-1;

[0061] In a 250mL three-neck flask, under the protection of nitrogen, add 0.02mol intermediate C-1, 0.03mol biboronic acid pinacol ester, 0.05mol potassium carbonate, 0.002mol Pd 3 (PPh) 4 and 100ml of toluene / water (volume ratio=5:1), stir and mix, heat to 80°C, react for 24 hours, take a sample point plate, it shows that there is no intermediate C-1 remaining, and the reaction is complete; naturally coo...

Embodiment 3

[0064] Embodiment 3: the synthesis of compound 27

[0065]

[0066]

[0067] In a 500mL three-neck flask, under the protection of nitrogen, add 0.03mol raw material B-3, 0.03mol m-dibromobenzene, 250mL toluene and stir to mix, then add 0.09mol potassium tert-butoxide and 0.09mol triphenylphosphine, 0.0015mol Pd 2 (dba) 3 , heated to 120°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced-pressure rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate C-2;

[0068] In a 250mL three-neck flask, under the protection of nitrogen, add 0.02mol of intermediate C-2, 0.03mol of pinacol borate, 0.05mol of potassium carbonate, 0.002mol of Pd 3 (PPh) 4 and 100ml toluene / water (volume ratio = 5:1), stir and mix, heat to 80°C, react for 24 hours, take a sample point plate, it shows that there is no intermediate C-2 remaining, and the reaction is complete; naturally...

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Abstract

The invention discloses a compound with an aza-spirofluorene structure as a mother nucleus and an application of the compound on organic electroluminescent devices. According to the compound, the aza-spirofluorene structure is used as a nucleus, and the compound has the characteristics of difficult crystallization and difficult gathering among molecules and excellent film-forming property. When the compound is used as a luminescent layer material or an electron barrier layer material of an organic electroluminescent device, current efficiency of the device is greatly improved; and meanwhile, the service life of the device is remarkably improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with an azaspirofluorene structure as the core and its application in organic electroluminescent devices. 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. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D471/10C07D513/04C07D491/107C07D491/20C07D495/04C07D417/14C07D401/04C09K11/06H01L51/50H01L51/54
CPCC07D519/00C07D471/10C07D513/04C07D491/107C07D491/20C07D495/04C07D417/14C07D401/04C09K11/06C09K2211/1029C09K2211/1088C09K2211/1033C09K2211/1037C09K2211/1092H10K85/654H10K85/6572H10K85/657H10K50/00
Inventor 繆康健张兆超李崇庞羽佳
Owner VALIANT CO LTD
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