Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

(Poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and preparation method and application thereof

A technology of substituents and alkyl groups, used in the synthesis and application of liquid crystal compounds

Active Publication Date: 2012-07-11
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since a single liquid crystal compound cannot meet the above requirements at the same time, it is required to use a variety of liquid crystal compounds with different properties to mix to meet the above performance requirements

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • (Poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and preparation method and application thereof
  • (Poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and preparation method and application thereof
  • (Poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] This example is the preparation of 2-((4-((4-ethoxyphenyl)ethynyl)phenyl)ethynyl)-1,3-difluoro-5-propylbenzene

[0054]

[0055] Step 1-1: Synthesis of the compound 4-(2,6-difluoro-4-propylphenyl)-2-methyl-3-butyn-2 alcohol shown in formula c

[0056]

[0057] Add 56.4 g of compound 1,3-difluoro-2-iodo-5-propylbenzene (0.2 mol) and 1 g of catalyst tetraphenylphosphine palladium (0.87 mmol, 0.4 mol%) in the three-necked flask With 50ml of tetrahydrofuran, the system was heated to 60°C under the protection of high-purity argon, and 21.8g (0.3mol) of 3-methyl-1-butyn-3-ol was added dropwise. After dropping, keep the temperature for coupling reaction for 5 hours, add saturated ammonium chloride aqueous solution to wash after cooling down, separate liquid extraction, separate through the column, and recrystallize from n-hexane to obtain the compound 4-(2,6-difluoro- 40.5 g (0.17 mol) of 4-propylphenyl)-2-methyl-3-butyn-2 alcohol, yield 85%.

[0058] Step 1-2: Synthes...

Embodiment 2

[0081] This example is the preparation of 5-ethyl-1,3-difluoro-2-((4-((4-methoxyphenyl)ethynyl)phenyl)ethynyl)benzene

[0082]

[0083] Step 1-1: Synthesis of 4-(4-ethyl-2,6-difluorophenyl)-2-methyl-3-butyn-2-ol

[0084]

[0085] Add 53.6 g of 5-ethyl-1,3-difluoro-2-iodobenzene (0.2 mol), 1 g of tetraphenylphosphine palladium (0.87 mmol, 0.4 mol%) and 50 ml of tetrahydrofuran into a three-necked flask, high-purity Under the protection of argon, the system was heated to 60°C, and 21.8 g (0.3 mol) of 3-methyl-1-butyn-3-ol was added dropwise. After dropping, keep the temperature for 5 hours, add saturated ammonium chloride aqueous solution to wash after cooling down, separate liquid extraction, separate through the column, and recrystallize from n-hexane to obtain the product 4-(4-ethyl-2,6-difluorophenyl)- 38.5 g (0.17 mol) of 2-methyl-3-butyn-2-ol.

[0086] Step 1-2: Synthesis of 5-ethyl-2-ethynyl-1,3-difluorobenzene

[0087]

[0088] 4-(4-Ethyl-2,6-difluorophenyl)-...

Embodiment 3

[0105] This example is the preparation of 4-((4-ethoxyphenyl)ethynyl)-4'-((2-fluoro-4-propylphenyl)ethynyl)biphenyl

[0106]

[0107] Step 1-1: Synthesis of 4-(2-fluoro-4-propylphenyl)-2-methyl-3-butyn-2-ol

[0108]

[0109] Add 52.8 g of 2-fluoro-1-iodo-4-propylbenzene (0.2 mol), 1 g of tetraphenylphosphine palladium (0.87 mmol, 0.4 mol%) and 50 ml of tetrahydrofuran into a three-necked flask, and protect the mixture with high-purity argon. The system was heated to 60° C., and 21.8 g (0.3 mol) of 3-methyl-1-butyn-3-ol was added dropwise. After dropping, keep the temperature for 5 hours, add saturated ammonium chloride aqueous solution to wash after cooling down, separate liquid extraction, separate through the column, and recrystallize from n-hexane to obtain the product 4-(2-fluoro-4-propylphenyl)-2-methanol 37.4 g (0.17 mol) of 3-butyn-2-ol.

[0110] Step 1-2: Synthesis of 1-ethynyl-2-fluoro-4-propylbenzene

[0111]

[0112] Put 4-(2-fluoro-4-propylphenyl)-2-met...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a (poly) fluorine substituted phenyl diacetylene (bi) phenyl derivative, and a preparation method and application thereof. The derivative has a structural general formula which is shown as a formula I. In the preparation process of a compound, a cross-coupling method is adopted, raw materials are easy to obtain, a synthesis route is simple, and the preparation method is suitable for large-scale industrial production. Meanwhile, the compound has high optical anisotropy (delta n), appropriate dielectric anisotropy (delta epsilon), high optical and chemical stability, can be used as the component of a liquid crystal composition and is used for adjusting the optical anisotropy (delta n) and the dielectric anisotropy (delta epsilon) of the liquid crystal composition, so the compound has certain application prospect in the aspect of liquid display.

Description

technical field [0001] The invention belongs to the field of synthesis and application of liquid crystal compounds, and relates to a (poly)fluorine-substituted phenyldiethynyl (bi)phenyl derivative and a preparation method and application thereof. Background technique [0002] With the rapid development of flat panel display technology, liquid crystal displays have received a lot of attention and been widely used in the field of flat panel displays. People put forward higher requirements on the performance of digital and image liquid crystal displays (Liquid Crystal Display, LCD). In recent decades, liquid crystal, as a special display material, has become a research hotspot in the field of applied chemistry, and has made continuous progress. [0003] According to the use requirements of liquid crystal display devices, liquid crystal materials should have certain performance requirements, such as wide nematic phase temperature range, low driving voltage, suitable optical an...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C43/225C07C41/30C07C25/24C07C17/266C09K19/18G02F1/1333
Inventor 李宁华瑞茂张兴卓晓曦杨增家王奎梁志安
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com