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Liquid crystal compound containing 1, 3-dioxolane and difluoro-methylenedioxy linking group and preparation method and application of liquid crystal compound

A compound, phenylene technology, applied in liquid crystal compounds and application fields, can solve the problems of lowering the clearing point of liquid crystal

Inactive Publication Date: 2013-05-08
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although difluoromethyleneoxy (CF 2 O) Liquid crystal molecules as bridges have the advantages mentioned above, but -CF 2 The introduction of O-group will greatly reduce the clearing point of liquid crystal

Method used

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  • Liquid crystal compound containing 1, 3-dioxolane and difluoro-methylenedioxy linking group and preparation method and application of liquid crystal compound
  • Liquid crystal compound containing 1, 3-dioxolane and difluoro-methylenedioxy linking group and preparation method and application of liquid crystal compound
  • Liquid crystal compound containing 1, 3-dioxolane and difluoro-methylenedioxy linking group and preparation method and application of liquid crystal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1, compound 1-d shown in formula I (o is not 0)

[0063]

[0064] step 1

[0065]

[0066] Add 400ml toluene (solvent), 74g (0.4mol) p-bromobenzaldehyde (reactant), 100g (1.6mol) ethylene glycol (reactant), 2.06g (12mmol) p-toluenesulfonic acid (dehydrating agent) to 1L three-necked flask , reflux and divide water for dehydration reaction for 4 hours, no more water will come out, distill the solvent under reduced pressure, dissolve it with petroleum ether, pass through a preheated silica gel column, rinse with petroleum ether, and concentrate the chromatographic solution to obtain a light yellow liquid ( 1-a) 92g, GC: 97%, yield: 98%.

[0067] step 2

[0068]

[0069] Add 92g (0.4mol) (1-a) (reactant), 70g (0.44mol) 3,5-difluorophenylboronic acid (reactant), 300ml toluene (solvent), 300ml ethanol (solvent) to a 2L three-necked flask, 300ml of water (solvent), 53g (0.5mol) of sodium carbonate (alkali), filled with nitrogen to replace the air, added...

Embodiment 2

[0088] Example 2, compound 2-c shown in formula I (o is 0)

[0089]

[0090] step 1

[0091]

[0092] Add 400ml toluene (solvent), 57g (0.4mol) 3,5-difluorobenzaldehyde (reactant), 100g (1.6mol) ethylene glycol (reactant), 2.06g (12mmol) p-toluenesulfonic acid to 1L three-necked flask (dehydrating agent), reflux and divide water for dehydration reaction for 4 hours, no more water will come out, distill the solvent under reduced pressure, dissolve with petroleum ether, pass through the preheated silica gel column, rinse with petroleum ether, and concentrate the chromatographic solution to obtain 75 g of light yellow liquid (2-a), GC: 97%, yield: 98%.

[0093] step 2

[0094]

[0095] Add 75g (0.4mol) (2-a) (reactant) and 500ml tetrahydrofuran (solvent) into a 1L three-neck flask, fill with nitrogen to replace the air, place in a low temperature tank and cool down with liquid nitrogen, when it drops to -60°C, add dropwise 175ml (0.44mol) of 2.5M hexane solution of n-...

Embodiment 3

[0109] With reference to the method of Examples 1 and 2, only the reactant substituents are replaced according to the corresponding substituents in the product to obtain the compound shown in the following formula:

[0110]

[0111] GC: 99.75%

[0112] mp: 43°C

[0113] cp: 21°C

[0114] MS: m / z (%) 472 (M + 4) 325(100) 251(35)

[0115] 1 HNMR (CDCl 3 / TMS):7.383~7.534(dd,4H),7.192~7.280(d,2H),7.062~7.144(d,2H),5.745(s,1H),3.881~4.083(m,3H),1.312~1.323 (d,3H).

[0116] Δn[589nm, 20°C]: 0.147

[0117] Δε[1KHz,20℃]:24.5

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Abstract

The invention provides a liquid crystal compound containing a 1, 3-dioxolane and difluoro-methylenedioxy linking group and a preparation method and application of the liquid crystal compound. The compound is represented by the formula I, and has high Delta Epsilon and a high cool point. The synthesis method of the compound is simple in process and low in production cost, and has a critical actual significance to blending of a liquid crystal mixer.

Description

technical field [0001] The invention belongs to the field of liquid crystal compounds and applications, and relates to a liquid crystal compound containing substituted 1,3-dioxolane and difluoromethyleneoxy linking groups, a preparation method and application thereof. Background technique [0002] Liquid crystal materials are developing rapidly with the development of LCD devices, gradually developing from biphenyl nitriles, esters, oxygen-containing heterocyclic benzenes, and pyrimidine ring liquid crystal compounds to cyclohexyl (bi)benzenes, tolanes, Ethyl bridging bonds and various fluorine-containing aromatic ring liquid crystal compounds continue to meet the performance requirements of STN and TFT-LCD. [0003] With difluoromethyleneoxy (CF 2 O) The liquid crystal molecule as a bridge was first proposed in 1990. Due to the introduction of more F atoms into the molecule and the increase of bridging groups, the rotational viscosity γ was reduced 1 , increased molecular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/22C09K19/34C09K19/46
Inventor 张兴员国良周兴丹李正强华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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