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1,2,4-oxadiazole compound as well as preparation method and application thereof

A technology of compound, Z1-A1-Z2, applied in 1 field

Active Publication Date: 2013-03-20
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But so far, oxadiazole derivatives with low ASE threshold and high carrier mobility have not been reported yet.

Method used

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  • 1,2,4-oxadiazole compound as well as preparation method and application thereof
  • 1,2,4-oxadiazole compound as well as preparation method and application thereof
  • 1,2,4-oxadiazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1, the preparation of compound 4-(5-trifluoromethyl-1,2,4-oxadiazolyl)phenol

[0067] step 1: Synthesis

[0068]

[0069] Into a 250mL reaction bottle, put 5.3mmol of 4-cyanophenol, 8.0mmol of hydroxylamine hydrochloride and 10.6mmol of sodium bicarbonate, put in 30mL of ethanol, and react under reflux at 80°C for 6h. Add 100 mL of water and 20 mL of ethyl acetate to the system, stir and separate the liquids, extract the aqueous phase twice with 30 mL of ethyl acetate, wash the organic phase twice with 30 mL of saturated brine, combine the organic phases, and spin dry to obtain a white solid. Yield: 95%.

[0070] Step 2: Synthesis

[0071]

[0072] Into a 250mL reaction flask, put 2.0mmol of 4-aminoximimophenol and 2.3mmol of trifluoroacetic anhydride in step 1, put in 50mL of toluene, and reflux at 110°C for ring closure reaction for 4h. The solvent was spin-dried, passed through a silica gel column, and washed with petroleum ether to obtain a...

Embodiment 2

[0076] Embodiment 2, the synthesis of compound 3-(2,6-difluoro-4-methoxyphenyl)-5-trifluoromethyl-1,2,4-oxadiazole

[0077] This embodiment refers to Example 1, and the 4-cyanophenol in step 1 is replaced by 2,6-difluoro-4-methoxybenzonitrile, and the 4-aminoximimophenol in step 2 is replaced by 2,6 -difluoro-4-methoxyaminoximinylbenzene, other operations are the same as in Example 1, and the target compound 3-(2,6-difluoro-4-methoxyphenyl)-5-trifluoromethyl- 1,2,4-oxadiazole.

[0078] step 1: Synthesis

[0079]

[0080] Yield: 90%.

[0081] Step 2: Synthesis

[0082]

[0083] Yield: 88%

[0084] The NMR data of this compound were measured: 1 H NMR (CDCl 3 , 300 MHz): δ = 6.53-6.56 (d, 2H), 3.82 (s, 3H). As can be seen from the above, the structure of the colorless liquid product is correct, and it is the compound 3-(2,6-difluoro-4-methoxyphenyl)-5-trifluoromethyl-1,2,4- Oxadiazole

[0085]

[0086] The liquid crystal performance data of this compound w...

Embodiment 3

[0087] Embodiment 3, the synthesis of compound 3-(4-butoxy-2-fluorophenyl)-5-trifluoromethyl-1,2,4-oxadiazole

[0088] This example refers to Example 1, and the 4-cyanophenol in step 1 is replaced by 2-fluoro-4-butoxybenzonitrile, and the 4-aminoximiphenol in step 2 is replaced by 2-fluoro-4- Butoxyaminoximine base benzene, other operation is the same as embodiment 1, prepares target compound 3-(4-butoxy group-2-fluorophenyl)-5-trifluoromethyl-1,2,4-oxadiazole .

[0089] step 1: Synthesis

[0090]

[0091] Yield: 94%.

[0092] Step 2: Synthesis

[0093]

[0094] Yield: 81%

[0095] The NMR data of this compound were measured: 1 H NMR (CDCl 3 , 300MHz): δ=8.05-8.10(m, 1H), 6.80-6.84(m, 2H), 4.04-4.06(t, 2H), 1.72-1.78(m, 2H), 1.42-1.45(m, 2H) , 0.88-091 (t, 3H). As can be seen from the above, the white solid product has a correct structure and is the compound 3-(4-butoxyl-2-fluorophenyl)-5-trifluoromethyl-1,2,4-oxadiazole shown in formula I

[0096]

[0...

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Abstract

The invention discloses a 1,2,4-oxadiazole compound and a preparation method and application thereof. The structural general formula of the compound is shown in a formula I. The preparation method comprises the following steps of: when RB is -CF3, performing a ring closing reaction between aminooxime substituted hydrocarbon shown by a formula IV and trifluoroacetic anhydride to obtain the compound shown by formula I when RB is -CF3, namely the compound shown by a formula V; and when RB is not -CF3, under the condition that the pH value of the reaction system is 8-14, uniformly mixing the aminooxime substituted hydrocarbon shown by the formula IV and 1-hydroxybenzotriazole (HOBt) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) and carboxylic acid shown by a formula VI to conduct a ring closing reaction, wherein the compound shown by the formula I when RB is not -CF3 is obtained after the reaction. The compound disclosed by the invention is correct through nuclear magnetic detection, can be used as liquid crystal display material and OLED (Organic Light-Emitting Diode) material, and has important application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a 1,2,4-oxadiazole compound and a preparation method and application thereof. Background technique [0002] With the continuous development of liquid crystal display technology, liquid crystal displays are more and more widely used in people's production and life. Due to the higher and higher requirements for the quantity and quality of text and image display, people have higher and higher requirements for the physical properties of the liquid crystal display liquid (mixed liquid crystal) and the performance of optoelectronic technology. [0003] Liquid crystal compounds should meet the following requirements: photothermal and electrochemical stability, wide range of nematic phase, low viscosity, fast photoelectric response speed and low driving voltage. [0004] Oxadiazole compounds are one of the most widely used electron transport and luminescent materials. Due to the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/06C09K11/06C09K19/34H01L51/54
Inventor 郭剑曹建华隋岩华瑞茂
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD