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Azulene derivative

A derivative, chamomile technology, applied in the field of organic electroluminescent compounds, can solve the problems of large hole transport layer voltage drop, complex industrial production process, low glass transition temperature, etc., to achieve high device efficiency and excellent market potential , the effect of high glass transition temperature

Inactive Publication Date: 2018-01-12
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such materials have the following disadvantages in terms of processability: during vapor deposition and coating processes, premature deposition occurs, thus complicating industrial production processes
[0005] In addition, the hole transport layer or hole injection layer materials in the prior art often have the following defects: low hole mobility, low glass transition temperature, and under thicker thickness conditions, the hole transport layer large voltage drop etc.

Method used

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  • Azulene derivative
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Preparation of Compound 1

[0052]

[0053] Add Intermediate 1 (5.7g, 20.0 mmol) and Intermediate 2 (13.0g, 45mmol), and 10ml of 2M aqueous sodium carbonate and 10ml of tetrahydrofuran into a round-bottomed flask containing 200 ml of toluene, and vent with argon. After 30 minutes, the catalyst tetrakis (triphenylphosphine) palladium (140 mg, 1.2 mmol) was quickly added, and the temperature was raised to 90 ° C under stirring conditions, and the reaction was carried out for 12 hours, and then cooled to room temperature; then ethyl acetate and deionized water were added , extract and combine the organic phases, and dry with anhydrous magnesium sulfate, reduce pressure, concentrate, and finally use silica gel column chromatography, the eluent is petroleum ether: dichloromethane=3:1, to obtain pure compound 1 (10.9 g, 17.8mmol), the yield was 89%.

[0054] High resolution mass spectrum (FAB) of compound 1 (C46H34N2) (m / z): [M] + The detected value is 614.2722...

Embodiment 2

[0055] Example 2 Preparation of Compound 3

[0056] Step 1: Synthesis of Intermediate 6

[0057]

[0058] Intermediate 4 (8.5 g, 50 mmol) and Intermediate 5 (12.4 g, 50 mmol) were dissolved in 200 ml of toluene, and after stirring for 30 minutes, sodium tert-butoxide (480 mg, 5mmol), 3-tert-butylphosphine (1.1g, 5mmol) and bis(dibenzylideneacetone) palladium (864 mg, 1.5 mmol), heated to 100°C, reacted overnight, cooled to room temperature, added water and dichloro Stir with methane, extract and combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and finally use silica gel column chromatography with petroleum ether as the eluent to obtain pure intermediate 6 (12.5 g, 37.5 mmol). The yield 75%.

[0059] HRMS (FAB) (m / z) of Intermediate 6 (C24H17NO): [M] + The detected value is 335.1310 and the theoretical value is 335.1320.

[0060] Step 2: Synthesis of Intermediate 7

[0061]

[0062] Intermediate 6 (12.5g, 37.5 mmol) ...

Embodiment 3

[0072] Example 3 Preparation of Compound 6

[0073]

[0074] Add intermediate 3 (5.7 g, 20.0 mmol) and intermediate 2 (13.0 g, 45 mmol), and 10 ml of 2M aqueous sodium carbonate solution and 10 ml of tetrahydrofuran into a round-bottomed flask filled with 200 ml of toluene, and argon After degassing for 30 minutes, the catalyst tetrakis(triphenylphosphine)palladium (140 mg, 1.2 mmol) was quickly added, and the temperature was raised to 90 ° C under stirring conditions. After 12 hours of reaction, it was cooled to room temperature, and ethyl acetate and deionized water, extract and combine the organic phases, and dry with anhydrous magnesium sulfate, concentrate under reduced pressure, and finally use silica gel column chromatography, the eluent is petroleum ether: dichloromethane=3:1, to obtain pure compound 6 (11.3g, 18.4mmol), the yield was 92%.

[0075] High resolution mass spectrum (FAB) of compound 6 (C46H34N2) (m / z): [M] + The detected value is 614.2722 and the theo...

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Abstract

The invention provides an azulene derivative, which has a structure represented by the formula (I). In the formula (I), L1, L2, L3, and L4 individually exist or not; when L1, L2, L3, and L4 exit, L1,L2, L3, and L4 are selected from aryl groups with a cyclization carbon number of 6-30 and heterocyclic aryl groups with a cyclization carbon number of 6-30; R1 to R8 are selected from H, a halogen atom, a cyano group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C3-C20 cycloalkyl group, a C3-C20 halogenated cycloalkyl group, a C1-C20 alkoxyl group, a C1-C20 silicyl group, an aryloxylgroup with a cyclization carbon number of 6-30, an aryl group with a cyclization carbon number of 6-30 and a heterocyclic aryl group with a cyclization carbon number of 6-30; and p, q, m, and n individually represent 0 or 1. The azulene derivative has high hole mobility and thermal stability. An OLED device prepared from the azulene derivative has the advantages of high efficiency, low turn-on voltage, and longer service life, and thus the azulene derivative has a great application value and wide market prospect.

Description

technical field [0001] The invention relates to an organic electroluminescent compound, in particular to an azulene derivative. Background technique [0002] Organic Light-Emitting Diodes (Organic Light-Emitting Diodes, hereinafter referred to as "OLED") have the characteristics of self-luminescence, compared with liquid crystal display technology, it has high contrast, wide viewing angle, fast response, low power consumption, and good color reproducibility As well as the huge advantages of being able to realize flexible devices, it has been widely commercialized in the fields of display and lighting. [0003] With the development of organic electroluminescent materials, arylamine derivatives known in the prior art are often used as hole transport and injection materials. Such commonly used arylamine derivatives are disclosed in WO2016017594 and WO2016013184. The operating voltage of hole transport materials in the prior art often increases with the thickness of the hole tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/54C07C211/57C07D307/91C09K11/06H01L51/54
Inventor 王历平
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD