Naphtho-thioxanthene derivative as well as preparation method and application thereof

A technology for naphthothanthene and derivatives, which is applied in the field of naphthothanthene derivatives and their preparation, can solve the problems of underappreciated, low driving voltage luminous efficiency and the like, and achieves improved luminous efficiency and excellent electron transport capability. , the preparation method is simple

Inactive Publication Date: 2017-01-25
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1963, Pope et al. from New York University in the United States observed luminescence when a voltage of several hundred volts passed through an anthracene crystal. However, due to the high driving voltage and low luminous efficiency, this technology was not taken seriously at that time.

Method used

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  • Naphtho-thioxanthene derivative as well as preparation method and application thereof
  • Naphtho-thioxanthene derivative as well as preparation method and application thereof
  • Naphtho-thioxanthene derivative as well as preparation method and application thereof

Examples

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preparation example Construction

[0041] The present invention also provides a preparation method of naphthothioxanthene derivatives, comprising:

[0042] Under the protection of nitrogen, the compound represented by the intermediate formula A or the compound represented by the intermediate formula B is subjected to a coupling reaction to obtain a naphthothioxanthene derivative represented by formula I or formula II;

[0043]

[0044] The R 1 , R 2 , R 3 , R 4 The selection of the groups is the same as above, and will not be repeated here.

[0045] According to the intermediate A of the present invention, it is prepared according to the following method:

[0046] (1) Nitrating the thioxanthone shown in formula A-1 with nitric acid to obtain the disubstituted nitro compound shown in formula A-2;

[0047] (2) The compound shown in formula A-2 and carbon tetrabromide are subjected to a Corey-Fuchs dibromoalkenylation reaction in the presence of triphenylphosphine to obtain a dibromoalkene compound shown i...

Embodiment 1

[0064] Embodiment 1: the preparation of intermediate A

[0065] (1) Synthesis of Compound A-2: Add 150ml of fuming nitric acid into a 500ml reaction flask, cool to about 5°C in an ice-water bath, add 21.2g (0.1mol) of thioxanthone (Compound A-1) in batches under stirring ), control the reaction temperature not to exceed 10°C, keep the temperature of the reaction solution at 5°C after adding the reactant, and react for about 30min. The reactant was poured into ice water, stirred vigorously, and filtered with suction. The filter cake was washed with water, dried and recrystallized to obtain compound A-2 with a yield of 80%.

[0066] (2) Synthesis of Compound A-3: 22.6g of Compound A-2 (0.075mol) and 50g of carbon tetrabromide (0.15mol) were added to a 500ml dry reaction flask, and 250ml of Benzene was dried, stirred for 5 min, and 78.6 g of triphenylphosphine (0.3 mol) was added. Stir the reaction mixture at 150°C and react for 48 hours. After the reaction system is cooled, a...

Embodiment 2

[0072] Embodiment 2: the preparation of intermediate B

[0073] (1) Synthesis of compound B-2: This step is basically the same as step (2) in Example 1, except that compound B-1 is used instead of A-2, and the yield is 68%.

[0074] (2) Synthesis of compound B-3: under nitrogen protection, add 2.6g zinc powder (0.04mol), a small amount of iodine and 100ml dry DMF in a 250ml reaction flask, add 5g ethyl bromoacetate (0.03mol) after stirring, Heat to 60°C, stir for 3h, filter the solution into another 250ml reaction flask, add 3.68g of compound B-2 (0.01mol) and 0.55g of Pd (PPh 3 ) 4 (5%eq.), heated to 120°C, reacted for 15h. It was extracted with ethyl acetate, separated and dried, and compound B-3 was obtained after column chromatography with a yield of 60%.

[0075] (3) Preparation of Compound B-4: Dissolve 38.2g of Compound B-3 (0.1mol) in 100ml of THF, add 100ml of an aqueous solution containing 12g of LiOH (0.5mol), and stir at room temperature until clear. The volume...

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Abstract

The invention provides a naphtho-thioxanthene derivative as well as a preparation method and application thereof, belonging to the technical field of organic optoelectronic materials. The material takes naphtho-thioxanthene groups as a center for connecting two conjugate non-planar structures, thus having good electron transmission ability and greatly improving luminous efficiency; therefore, the material can be used for preparing an organic light-emitting device (OLED), and more particularly, the OLED taking the material as an electron transport material or a light-emitting layer main body material is superior to the existing commonly-used OLED. The invention also provides the preparation method of the naphtho-thioxanthene derivative; the preparation method is simple, thus being suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a naphthothioxanthene derivative and its preparation method and application. Background technique [0002] Organic Light Emitting Diode (OLED) is a current-driven light-emitting device that uses organic materials as active materials. Specifically, organic semiconductor materials and organic light-emitting materials are driven by electric fields through carrier injection and Composite technology that leads to luminescence. The research on the phenomenon of organic electroluminescence began in the 1960s. In 1963, Pope et al. from New York University in the United States observed luminescence when a voltage of several hundred volts passed through an anthracene crystal. However, due to the high driving voltage and low luminous efficiency, this technology was not taken seriously at that time. In 1987, C.W.Tang et al. of Kodak Corporation of the United States ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/04C07D409/14C07D519/00C07D417/14C07D413/14H01L51/54
CPCC07D335/04C07D409/14C07D413/14C07D417/14C07D519/00H10K85/656H10K85/6565H10K85/626H10K85/654H10K85/6576H10K85/6572H10K85/657
Inventor 赵倩郭建华
Owner CHANGCHUN HYPERIONS TECH CO LTD
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