Compounds adopting dibenzo six-membered heterocyclic rings as cores and applications thereof

A technology of six-membered heterocycles and compounds, which is applied in the application field of organic compounds and organic electroluminescent devices, can solve problems such as performance differences, achieve high glass transition temperature, improve current efficiency and life, and reduce efficiency roll-off Effect

CN108164470AInactive Publication Date: 2018-06-15JIANGSU SUNERA TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2018-06-15
Estimated Expiration
Not applicable · inactive patent

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Abstract

Organic compounds adopting dibenzo six-membered heterocyclic rings as cores and applications thereof in organic electroluminescence devices are disclosed. The compounds have high glass transition temperatures and molecular thermal stability, proper HOMO and LUMO energy levels and high Eg. Through optimization of device structures, photoelectric properties of OLED devices can be effectively improved and service lifetime of the OLED devices can be effectively prolonged.
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Description

technical field

[0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with a dibenzo-6-membered heterocyclic ring 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 ele...

Examples

Embodiment 1

[0048] Embodiment 1: the synthesis of compound 3:

[0049] synthetic route:

[0050]

[0051] In a 250mL three-neck flask, under nitrogen atmosphere, add 0.02mol 2-bromo-10-H-phenoxazine, 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 raw material A1.

[0052] In a 250mL three-neck flask, under nitrogen protection, add 0.03mol 3-bromophenazine, 0.036mol 9,9-dimethylacridine, 150mL toluene and stir to mix, then add 0.09mol sodium tert-butoxide, 0.015mol Pd 2 (dba) 3 , 0.015mol tri-tert-butylphosphine, heated to 120°C, and refluxed for 24 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotar...

Embodiment 2

[0056] Embodiment 2: the synthesis of compound 6:

[0057] synthetic route:

[0058]

[0059] In a 250mL three-necked flask, under nitrogen protection, add 0.03mol 2-bromo-9,9-dimethylacridine, 0.036mol carbazole, 150mL toluene and stir to mix, then add 0.09mol sodium tert-butoxide, 0.015mol PD 2 (dba) 3 , 0.015mol tri-tert-butylphosphine, heated to 120°C, and refluxed 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 the intermediate M2;

[0060] Weigh 0.01mol of the above-obtained intermediate M2 and 0.015mol of raw material A1 and dissolve them in 150mL of anhydrous toluene, add 0.02mol of sodium tert-butoxide and 10 -4 mol Pd(dppf)Cl 2 , heated to reflux for 15 hours, sampling point plate, the raw material reacted completely; naturally cooled to room temperature (20 ~ 25 ° C), filtered, collected the filtrate and carried...

Embodiment 3

[0063] Embodiment 3: the synthesis of compound 16:

[0064] synthetic route:

[0065]

[0066] In a 250mL three-neck flask, under nitrogen protection, add 0.03mol 3-bromophenazine, 0.036mol carbazole, 150mL toluene and stir to mix, then add 0.09mol sodium tert-butoxide, 0.015mol Pd 2 (dba) 3 , 0.015mol tri-tert-butylphosphine, heated to 120°C, and refluxed 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 the intermediate M2;

[0067] Weigh 0.01mol of intermediate M3 obtained above and 0.015mol of raw material A1 and dissolve in 150mL of anhydrous toluene, add 0.02mol of sodium tert-butoxide and 10 -4 mol Pd(dppf)Cl 2 , heated to reflux for 15 hours, sampling point plate, the raw material reacted completely; naturally cooled to room temperature (20 ~ 25 ° C), filtered, collected the filtrate and carried out vacuum rotary evap...