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Pyrimidine liquid crystal compound with high birefringence and preparation method thereof

A technology of compounds and intermediates, which is applied in the field of pyrimidine liquid crystal compounds and their preparation, can solve problems such as high viscosity, melting point and clearing point, and affect liquid crystal mixing and compatibility, and achieve weak interaction, reduced thickness, and broad The effect of applying the foreground

Inactive Publication Date: 2014-11-05
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Strongly polar terminal groups often lead to higher viscosity, melting point and clearing point, affecting the mixing and compatibility of liquid crystals

Method used

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  • Pyrimidine liquid crystal compound with high birefringence and preparation method thereof
  • Pyrimidine liquid crystal compound with high birefringence and preparation method thereof
  • Pyrimidine liquid crystal compound with high birefringence and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of compound Ia

[0045]

[0046] Take R as X is The formula I compound of the present invention introduces the synthetic method of the pyrimidine liquid crystal compound containing isothiocyanate group as an example:

[0047] 1. Synthesis of intermediate m1-1:

[0048]

[0049]Add 2.26g (12mmol) of 4-pentyloxyphenylacetylene and 2.84g (10mmol) of 2-iodo-5-bromopyrimidine into a 250ml three-necked flask, add 50ml of tetrahydrofuran and 50ml of triethylamine to completely dissolve the raw materials, and pass argon After gas sonication for 30 minutes, 105 mg of tetrakis(triphenylphosphine) palladium, 57 mg of cuprous iodide, and 75 mg of triphenylphosphine were added, and the mixture was incubated at 35° C. under argon gas for 8 hours. After the reaction, the solvent was distilled off and purified by column chromatography. 2.79 g of white solid m1-1 was obtained with a yield of 81%.

[0050] 2. Synthesis of intermediate m2-1:

[00...

Embodiment 2

[0059] Embodiment 2: the synthesis of compound Ib

[0060]

[0061] Take R as -O-C 5 h 11 , X is The formula I compound of the present invention introduces the synthetic method of the pyrimidine liquid crystal compound containing isothiocyanate group as an example:

[0062] 1. Synthesis of intermediate m1-2:

[0063]

[0064] Add 5.22g (30mmol) of 5-bromo-2-hydroxypyrimidine into a 100mL three-necked flask, then add 30mL of N-N-dimethylformamide (DMF), and stir. Then 12ml of deionized water, 0.25g of tetrabutylammonium bromide, and 6.21g (45mmol) of potassium carbonate were added respectively. The temperature was raised to 65° C., and then 6 g (40 mmol) of n-pentane bromide was added dropwise. After the dropwise addition was completed, the reaction was carried out under temperature control for 4 hours. After the reaction, wash with water, extract, distill off the solvent, and purify by column chromatography. 5.71 g of white solid m1-2 was obtained, with a yield o...

Embodiment 3

[0074] Embodiment 3: the synthesis of compound Ic

[0075]

[0076] Take R as -O-C 5 h 11 , X is The formula I compound of the present invention introduces the synthetic method of the pyrimidine liquid crystal compound containing isothiocyanate group as an example:

[0077] 1. Synthesis of intermediate m1-2:

[0078]

[0079] Add 4.35g (25mmol) of 5-bromo-2-hydroxypyrimidine into a 100mL three-necked flask, then add 25mL of N-N-dimethylformamide (DMF), and stir. Then 10 mL of deionized water, 0.21 g of tetrabutylammonium bromide, and 5.17 g (37.5 mmol) of potassium carbonate were added respectively. The temperature was raised to 65° C., and then 5 g (33 mmol) of n-pentane bromide was added dropwise. After the dropwise addition was completed, the reaction was carried out under temperature control for 4 hours. After the reaction, wash with water, extract, distill off the solvent, and purify by column chromatography. Obtained 4.82g white solid m1-2, yield 79%.

[0...

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PUM

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Abstract

The invention discloses a pyrimidine liquid crystal compound with high birefringence and a preparation method thereof. The compound has a structure as shown a formula I, wherein R represents one of alkoxy, alkyl phenyl, alkoxyl phenyl, alkylbenzene acetylene, and alkoxy phenylacetylene; and X is one of phenyl, phenyl acetylene, biphenyl and biphenyl acetylene. The compound has the advantages of a long pi-electron conjugated system, introduction of isothiocyano group to the end group, lower dipole moment and viscosity than cyano group, high resistivity and voltage conservation rate, weak interactions of the internal molecules, and prevention of the formation of bipolymer. The compound of the present invention has high birefringence rate and is a liquid crystal material and optical material with excellent performance.

Description

technical field [0001] The invention relates to a class of pyrimidine liquid crystal compounds containing isothiocyanate groups and a preparation method thereof, belonging to the technical field of liquid crystal compounds. Background technique [0002] In recent years, liquid crystal materials with high birefringence have received extensive attention. High birefringence liquid crystal materials have important applications in display devices such as polymer dispersed liquid crystals, spatial light modems, and directional reflections. In addition, high birefringence liquid crystal materials also have its application prospects in optoelectronic devices such as steering laser beams and communication variable attenuators. Liquid crystal materials with high birefringence are classified according to molecular weight, including small molecule high birefringence liquid crystal materials and polymer high birefringence liquid crystal materials. For the characteristics of liquid crys...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C07D239/34C09K19/34
CPCC07D239/26C07D239/34C09K19/3469
Inventor 杨槐赵玉真张兰英贺泽民李辰悦
Owner PEKING UNIV
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