Benzoxazine compound, organic electroluminescent device, and electronic device

A benzoxazine and compound technology, which is applied in the field of organic electroluminescent materials to achieve the effects of good film formation, improved current efficiency, and difficulty in crystallization

Inactive Publication Date: 2020-04-21
SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, OLED display technology has been applied in fields such as mobile phones and tablet computer screens, and is expected to be widely used in large-size display applications such as TVs in the future. However, due to the current luminous efficiency and service life of OLED devices, there are still certain limitations. need further improvement

Method used

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  • Benzoxazine compound, organic electroluminescent device, and electronic device
  • Benzoxazine compound, organic electroluminescent device, and electronic device
  • Benzoxazine compound, organic electroluminescent device, and electronic device

Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0070] The preparation example is used to illustrate the synthesis of starting material A.

[0071]

[0072]Add raw material 1 (56.4g, 0.206mol, CAS: 189748-25-2) and dichloromethane (500ml) into the reaction flask, heat up to 25°C under stirring, and add zinc powder (14.82g, 0.227mol), filter after reacting for 1h, add concentrated sulfuric acid (40.38g, 0.412mol) to the filtrate and stir for 30min, slowly add 1L of ice water to it, separate liquids, extract the aqueous phase with dichloromethane, wash the organic phase with water until neutral It was dried with anhydrous sodium sulfate, concentrated to dryness, and recrystallized with petroleum ether to obtain 42.9 g of solid material A with a purity of >98% and a yield of 69%. m / z=227.16[M+H] + ;Elemental analysis calculated value C 8 h 6 BrNO 2 , Theoretical C, 42.14; H, 2.65; Br, 35.04; N, 6.14; O, 14.03, Found C, 42.12; H, 2.64;

Embodiment 1

[0073] Embodiment 1: the synthesis of compound 2

[0074] (1)

[0075]

[0076] Under nitrogen atmosphere, raw material A (50g, 0.219mol) and tetrahydrofuran (500ml) were added to the reaction flask, and then water (100ml), potassium carbonate (60.61g, 0.438mol), raw material B were added in sequence 1 (43.37g, 0.219mol), tetrakis(triphenylphosphine)palladium (1.27g, 0.001mol), warming up to 80°C, stirring for 15h, the reaction was completed, adding water after cooling, extracting with dichloromethane, and extracting the extract with Dry over sodium sulfate for 1h, filter, concentrate the filtrate to dryness under reduced pressure, and recrystallize with ethanol to obtain 42.9g of Intermediate A 1 , purity > 98%, yield 65%.

[0077] (2)

[0078]

[0079] Intermediate A 1 (42.9g, 0.142mol) was added to the reaction flask under a nitrogen atmosphere, and then the raw material C was added in sequence 1 (33.18g, 0.142mol), DMF (429ml), 1,10-phenanthroline (0.28g, 0.0014...

Embodiment 2

[0086] Embodiment 2: the synthesis of compound 5

[0087] (1)

[0088]

[0089] Under nitrogen atmosphere, raw material A (50g, 0.219mol) and tetrahydrofuran (500ml) were added to the reaction flask, and then water (100ml), potassium carbonate (60.61g, 0.438mol), raw material B were added in sequence 2 (26.7g, 0.219mol), tetrakis(triphenylphosphine)palladium (1.27g, 0.001mol), warming up to 80°C, stirring for 13h, the reaction was completed, adding water after cooling, extracting with dichloromethane, extracting the extract with Dry over sodium sulfate for 1 hour, filter, concentrate the filtrate to dryness under reduced pressure, and recrystallize with ethanol to obtain 32.06g of Intermediate A 2 , purity > 98%, yield 65%.

[0090] (2)

[0091]

[0092] Intermediate A 2 (32.06g, 0.142mol) was added to the reaction flask under a nitrogen atmosphere, and then the raw materials C were added in sequence 2 (29.40g, 0.142mol), DMF (320.6ml), 1,10-phenanthroline (0.28g, 0...

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Abstract

The invention belongs to the field of organic electroluminescent materials, and provides a benzoxazine compound, an organic electroluminescent device and an electronic device. The benzoxazine compoundhas a structure as shown in a chemical formula 1 which is described in the specification. In the chemical formula 1, Q1 and Q2 are respectively and independently selected from the group consisting ofa substituted or unsubstituted aryl group of C6-C30 and a substituted or unsubstituted heteroaryl group of C3-C30. When the compound provided by the invention is applied to an OLED device as a luminescent material, the current efficiency, the power efficiency and the external quantum efficiency of the device can be improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to a benzoxazine compound, an organic electroluminescence device and an electronic device comprising the compound. Background technique [0002] Organic electroluminescence (OLED) devices have been widely used in some electronic products as early as 2003 due to their characteristics of lightness, lightness, power saving, self-luminescence, low voltage requirements and high power saving efficiency. Its whole structure includes hole transport layer (HTL), light emitting layer (EL), electron transport layer (ETL), wrapped into a sandwich structure. When the power is supplied to an appropriate voltage, positive holes and negative charges will combine in the light-emitting layer to produce light. According to different formulas, three primary colors of red, green and blue RGB will be produced to form basic colors. [0003] At present, OLED display technology has been...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D413/14C09K11/06H01L51/54H01L51/50
CPCC07D413/14C07D413/04C09K11/06C09K2211/1033C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1011H10K85/622H10K85/615H10K85/654H10K85/657H10K85/6576H10K85/6572H10K85/6574H10K50/16
Inventor 张文高昌轩王金平
Owner SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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