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Compounds containing naphthyl substituted pyridazine structural unit, and preparation method and application thereof

A compound and a technology for preparation steps are applied in the field of new compounds containing naphthyl-substituted pyridazine structural units and their preparation fields, and can solve problems such as the gap between practical applications and the like

Active Publication Date: 2014-07-02
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently known materials with practical value and potential are still very limited. In particular, organic materials with excellent comprehensive indicators are in urgent need of research and development. Green materials are developing the fastest and can basically meet the needs of commercialization and practicality. Red and blue materials There are many problems, and there is still a distance from practical application

Method used

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  • Compounds containing naphthyl substituted pyridazine structural unit, and preparation method and application thereof
  • Compounds containing naphthyl substituted pyridazine structural unit, and preparation method and application thereof
  • Compounds containing naphthyl substituted pyridazine structural unit, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Embodiment 1, compound preparation of

[0081] step 1: Synthesis

[0082]

[0083] Into the 250mL reaction flask, put 58.1mmol of 2-naphthoic acid and 40mL of ethanol, then heat to reflux, add 2mL of thionyl chloride dropwise, and reflux for 6 hours after the dropwise addition. Then the reaction solution was spin-dried to obtain a colorless liquid product, yield: 90%.

[0084] Step 2: Synthesis

[0085]

[0086] Into a 250mL reaction flask, put 52.4mmol of compound 1a obtained in Step 1 of Example 1, 104.8mmol of NaH and 100mL of THF, and heat to maintain reflux. A solution of 78.7 mmol ethyl acetate in 30 mL THF was added dropwise, and after the dropwise addition was completed, the reaction was refluxed for 8 hours. Add 100ml of saturated aqueous solution of sodium chloride and 50mL of ethyl acetate to the system, stir and separate the liquids, extract the aqueous phase twice with 30mL of ethyl acetate, wash the organic phase twice with 30mL of saturat...

Embodiment 2

[0117] Embodiment 2, compound Synthesis

[0118] Step 1-step 7 is the same as embodiment 1.

[0119] Step 8: Synthesis

[0120]

[0121] In this step, referring to step 8 of Example 1, the methyl bromide in Step 8 of Example 1 was replaced with bromobenzene, and other operations were the same as Step 8 of Example 1 to prepare the target compound with a yield of 66%.

[0122] Step 9: Synthesis

[0123]

[0124] For this step, refer to step 9 of Example 1, replace 1h in step 9 of Example 1 with compound 2h obtained in step 8 of Example 2, and other operations are the same as step 9 of Example 1 to prepare the target compound, yield: 58% .

[0125] Step 10: Synthesis

[0126]

[0127] This step refers to step 10 of Example 1, replaces 1i in step 10 of Example 1 with compound 2i obtained in step 9 of Example 2, and other operations are the same as step 10 of Example 1 to prepare the target compound, yield: 71% .

[0128] 1 H NMR (CDCl 3,300MHz): δ=8.76...

Embodiment 3

[0134] Embodiment 3, compound Synthesis

[0135] step 1: Synthesis

[0136]

[0137] This step refers to step 1 of Example 1, and the 2-naphthoic acid in step 1 of Example 1 is replaced by 1-methyl 2-naphthoic acid, and other operations are the same as step 1 of Example 1 to prepare the target compound. The yield : 92%.

[0138] Step 2: Synthesis

[0139]

[0140] For this step, refer to step 2 of Example 1, replace 1a in step 2 of Example 1 with compound 3a obtained in step 1 of Example 3, and other operations are the same as step 2 of Example 1 to prepare the target compound, yield: 86% .

[0141] Step 3: Synthesis

[0142]

[0143] For this step, refer to step 3 of Example 1, replace 1b in step 3 of Example 1 with compound 3b obtained in step 2 of Example 3, and other operations are the same as step 3 of Example 1 to prepare the target compound, yield: 77% .

[0144] Step 4: Synthesis

[0145]

[0146] This step refers to step 4 of Example ...

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Abstract

The invention discloses compounds containing naphthyl substituted pyridazine structural unit, and a preparation method and application thereof. The structural general formula of the compounds containing naphthyl substituted pyridazine structural unit is disclosed as Formula I. The compounds disclosed as Formula I have proper nuclear magnetic detection; and in order to solve the problems of less research on near-infrared materials and deficiency in high-efficiency high-stability near-infrared luminescent materials at present stage, the invention provides a series of near-infrared luminescent materials containing naphthyl substituted pyridazine structure. The compounds have the advantages of accessible raw material, simple preparation process and high overall yield, and have important application value for researching development and application of near-infrared materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a new compound containing a naphthyl-substituted pyridazine structural unit, a preparation method and an application thereof. Background technique [0002] For organic electroluminescence (referred to as OLED) and related research, as early as 1963, Pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display And other advantages, can be widely used in flat panel displays and surface l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/26C09K11/06H01L51/54
CPCC09K11/06C07D237/26C09K2211/1044H10K85/615H10K85/654H10K85/6572
Inventor 郭剑隋岩曹建华华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD