Compound taking carbazole as core, and applications thereof in organic light-emitting devices

A compound and carbazole technology, applied in the application field of organic electroluminescent devices, can solve the problems of different performance, achieve high glass transition temperature, reduce efficiency roll-off, and improve hole injection/transport performance

Inactive Publication Date: 2018-06-26
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 taking carbazole as core, and applications thereof in organic light-emitting devices
  • Compound taking carbazole as core, and applications thereof in organic light-emitting devices
  • Compound taking carbazole as core, and applications thereof in organic light-emitting devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of compound 7:

[0045] synthetic route:

[0046]

[0047] In a 250mL three-neck flask, under an atmosphere of nitrogen gas, add 0.02mol 2-bromocarbazole, 0.03mol bromobenzene, 0.04mol sodium tert-butoxide, 10 -4 mol Pd 2 (dba) 3 , 10 -4 mol P(t-Bu) 3 and 200mL of toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials reacted completely; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , to obtain the target product raw material A1;

[0048] In a 250mL three-necked flask, under nitrogen protection, add 0.03mol dibenzofuran-2-amine, 0.04mol 2-(3-bromonaphthyl) propan-2-ol, 150mL toluene and stir to mix, then add 0.05mol t- Sodium butoxide, 0.0015mol Pd 2 (dba) 3 , 0.0015mol tri-tert-butylphosphine, heated to 115°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the ...

Embodiment 2

[0053] Embodiment 2: the synthesis of compound 8:

[0054] synthetic route:

[0055]

[0056]

[0057] In a 250mL three-neck flask, under nitrogen protection, add 0.04mol 9,9-dimethyl-9H-fluoren-3-ol, add 100mL acetic acid, stir and dissolve at room temperature, and slowly add 0.05 mol Br 2 50 mL of acetic acid solution, stirred at room temperature for 12 hours. Add NaOH aqueous solution (2mol / L) to neutralize to neutral, solid precipitates out, filter to take filter cake, dry under vacuum, pass through neutral silica gel column to obtain 4-bromo-9,9-dimethyl-9H-fluorene -3-ol;

[0058] In a 250mL three-neck flask, under nitrogen protection, add 0.04mol 4-bromo-9,9-dimethyl-9H-fluoren-3-ol, add 30% ammonia water (volume ratio) 100mL, heat to 80°C for reaction 6 hours. The system was cooled to room temperature, and evaporated under reduced pressure (-0.09MPa, 120°C), and passed through a neutral silica gel column to obtain 4-amino-9,9-dimethyl-9H-fluoren-3-ol;

[00...

Embodiment 3

[0063] Embodiment 3: the synthesis of compound 14:

[0064] synthetic route:

[0065]

[0066] In a 250mL three-neck flask, under nitrogen protection, add 0.04mol 9,9-dimethyl-9H-fluoren-3-ol, add 100mL acetic acid, stir and dissolve at room temperature, and slowly add 0.05 mol Br 2 50mL of acetic acid solution, stirred at room temperature for 12 hours; added NaOH aqueous solution (2mol / L) to neutralize to neutrality, solid precipitated, filtered to take filter cake, dried under vacuum, and passed through a neutral silica gel column to obtain 2-bromo-9 ,9-Dimethyl-9H-fluoren-3-ol;

[0067] In a 250mL three-neck flask, under nitrogen protection, add 0.04mol 2-bromo-9,9-dimethyl-9H-fluoren-3-ol, add 30% ammonia water (volume ratio) 100mL, heat to 80°C for reaction 6 hours; the system was cooled to room temperature, vacuum rotary evaporation (-0.09MPa, 120°C), and passed through a neutral silica gel column to obtain 2-amino-9,9-dimethyl-9H-fluoren-3-ol;

[0068] In a 250mL...

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Abstract

The invention discloses a compound taking carbazole as a core, and applications thereof in organic light-emitting devices. The structure of the compound is represented by formula I, is relatively highin glass transition temperature and molecular heat stability, possesses appropriate HOMO and LUMO energy level, and relatively high Eg, and is capable of improving the photoelectric properties of OLEDs and prolonging the service life of OLEDs through device structure optimization.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with carbazole 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. [0003] 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 the positive...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D403/04C07D413/04C07D413/14C07D417/04C07D471/04C07D471/06C07D471/14C07D487/06C07D487/14C07D491/048C07D491/056C07D491/153C07D495/04C07D498/04C07D498/06C07D498/14C07D513/04C07D513/06C07D519/00H01L51/54
CPCC07D401/04C07D401/14C07D403/04C07D413/04C07D413/14C07D417/04C07D471/04C07D471/06C07D471/14C07D487/06C07D487/14C07D491/048C07D491/056C07D491/153C07D495/04C07D498/04C07D498/06C07D498/14C07D513/04C07D513/06C07D519/00H10K85/657H10K85/6572
Inventor 缪康健张兆超张小庆李崇
Owner VALIANT CO LTD
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