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Aryl amine derivative containing carbazole and carboline and organic electroluminescent element containing aryl amine derivative

An arylamine and derivative technology, applied in the field of novel arylamine derivatives, can solve the problems of difficult to use organic light-emitting elements, and achieve the effect of improving lifespan

Inactive Publication Date: 2019-04-02
LAPTO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] NPB, which is mainly used as a hole-transporting material for the hole-transporting layer, has a glass transition temperature of 100°C or lower, making it difficult to use in organic light-emitting devices that require high current.

Method used

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  • Aryl amine derivative containing carbazole and carboline and organic electroluminescent element containing aryl amine derivative
  • Aryl amine derivative containing carbazole and carboline and organic electroluminescent element containing aryl amine derivative
  • Aryl amine derivative containing carbazole and carboline and organic electroluminescent element containing aryl amine derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: Synthesis of compound 3-1 (DC1A-md-C3)

[0073] The synthesis route of DC1A-md-C3 is shown below.

[0074]

[0075] Synthesis of Intermediate 1:

[0076] In a 250ml two-necked flask, add 7g (42mmol) of δ-carboline (δ-carboline), 9.3g (46mmol) of 1-bromo-3-nitrobenzene (1-bromo-3-nitrobenzene), 0.52g (3mmol) of CuI, 0.94g (5mmol) of 1,10-phenanthroline (1,10-phenanthroline), 22g (104mmol) of K 3 PO 4 , 120ml of two Dioxane, reflux at 80-100°C for 24 hours in a nitrogen atmosphere. After the reaction, the reactant was dissolved in dichloromethane (Methylene Chloride, MC) and filtered with diatomaceous earth (Celite). After the filtered solution was distilled under reduced pressure, extraction was performed with MC and distilled water. The extracted MC layer was washed with MgSO 4 After removing water, the solvent was distilled off under reduced pressure to obtain a yellow solid. From this solid, a white solid (1) (7.5 g, yield: 65%) was isolated ...

Embodiment 2

[0082] Embodiment 2: Synthesis of Compound 3-2 (C1A-md-DC3)

[0083] The synthesis route of C1A-md-DC3 is shown below.

[0084]

[0085] Synthesis of Intermediate 3:

[0086] In a 250ml two-necked flask, add 15g (89mmol) of carboline (δ-carboline), 37.8g (134mmol) of 1-bromo-3-iodobenzene (1-bromo-3-iodobenzene), 1.1g ( 5.79mmol) of CuI, 2g (11.13mmol) of 1,10-phenanthroline (1,10-phenanthroline), 47g (220mmol) of K 3 PO 4 , 300ml of two Dioxane, reflux at 80-100°C for 24 hours in a nitrogen atmosphere. After the reaction, the reactant was dissolved in MC and filtered through diatomaceous earth (Celite). The filtered solution was distilled under reduced pressure, and extracted with dichloromethane and distilled water. The extracted dichloromethane layer was washed with MgSO 4 After removing water, the solvent was distilled off under reduced pressure to obtain a yellow solid. From this solid, a white solid (3) (18.0 g, yield: 62%) was isolated by column chromatograp...

Embodiment 3

[0090] Embodiment 3: the synthesis of compound 3-3 (C3A-md-DC3)

[0091] The synthesis route of C3A-md-DC3 is shown below.

[0092]

[0093] In a 250ml two-necked flask, 0.6g (2.3mmol) of Intermediate 2, 1.7g (5mmol) of Intermediate 3, 0.67g (6.9mmol) of NaO t Bu was added into 100 ml of toluene, stirred in a nitrogen atmosphere, and the reaction temperature was raised to 80° C. and reacted for 1 hour. Add 0.07g (0.07mmol) of Pd to it 2 (dba) 3 , 0.02g (0.09mmol) of (tert-Bu) 3 P, react at 80°C for 4-5 hours. The above reaction liquid was filtered to remove the salt. The filtrate was distilled off to remove toluene, and the concentrate was separated with a column to obtain 1.1 g of compound 3-3 (C3A-md-DC3) (yield: 68%). The NMR analysis result of the obtained compound 3-3 (C3A-md-DC3) is as follows (with reference to Figure 4 ).

[0094] NMR analysis results: 1 H NMR(300MHz,DMSO)δ8.54(m,3H),8.28(d,3H),7.75(m,3H),7.65(m,12H),7.54(m,3H),7.44(m,6H) ,7.36(m,3H)

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Abstract

The invention provides an aryl amine derivative represented by the following chemical formula 1. In the following chemical formula 1, the definition of each substituent is the same as the definition of the specific embodiment of the invention.

Description

technical field [0001] The present invention relates to an arylamine derivative and an organic electroluminescent element comprising the arylamine derivative, in particular to an organic electroluminescent element with high luminous efficiency and a novel arylamine derivative used therein. Background technique [0002] In 1987, Tang and Van Slyke reported the use of organic light emitting diode (organic light emitting diode, OLED) after the multilayer thin film structure obtained high efficiency characteristics [Tang, C.W., Van Slyke, S.A.Appl.Phys.Lett.51,91 (1987)], because OLED not only has excellent characteristics as a next-generation display but also has the potential to be used in LCD backlighting and lighting, etc., a lot of research is going on [Kido, J., Kimura, M., and Nagai, K ., Science 267, 1332 (1995)]. [0003] In particular, in order to improve the luminous efficiency, various researches such as structural changes of devices and material development are bei...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1014C09K2211/1029C09K2211/1007H10K85/631H10K85/6572H10K50/15H10K50/17
Inventor 吴唯真韩甲钟
Owner LAPTO CO LTD
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