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Bicyclo[3,3,0]octane polymerizable compound

A compound and liquid crystal composition technology, applied in the liquid crystal field, can solve the problems of poor uniformity and low TFT display

Inactive Publication Date: 2016-07-27
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is mainly due to the fact that the polymerizable unit is too short for the UV sensitive wavelength, or there is no or insufficient tilt angle after illumination, or the uniformity of the polymerizable component is poor after illumination, or because the VHR after UV is not suitable for TFT display applications lower impact

Method used

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  • Bicyclo[3,3,0]octane polymerizable compound
  • Bicyclo[3,3,0]octane polymerizable compound
  • Bicyclo[3,3,0]octane polymerizable compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1, compound shown in preparation formula I1

[0068]

[0069] step 1

[0070]

[0071] Add 13g (0.54mol) magnesium chips into a 1L three-neck flask, 100mlTHF, fill with nitrogen to replace the air, heat to reflux, add dropwise a small amount of 91g (0.486)mol p-bromoanisole in 350mlTHF solution, after initiating the reaction, add it in one hour Complete, and then reflux for half an hour to obtain a black Grignard reagent solution.

[0072] Cool the Grignard reagent solution to 20°C, add 28g (0.2mol) of bicyclo[3,3,0]octane 3,7-dione in 100ml of toluene solution dropwise, a lot of solids are precipitated, exothermic, the addition is completed in one hour, and then The reaction was stirred at 60°C for 4 hours.

[0073] The reaction solution was poured into 1L of ice water with 50ml of hydrochloric acid for hydrolysis, the aqueous phase was separated, extracted with 200ml of toluene, the organic phase was combined, washed twice with water, and the solven...

Embodiment 2

[0104] Embodiment 2, compound shown in preparation formula I5

[0105]

[0106] step 1

[0107]

[0108] Put 94.5g (1mol) of 3-chloropropanol into a 1L three-necked bottle, add 300ml of dichloromethane, 121g (1.2mol) of triethylamine, 0.2g of polymerization inhibitor, add dropwise 99.5g (1.1mol) of acryloyl chloride, add The reaction was stirred at room temperature for 13 hours.

[0109] The precipitated salt was removed by filtration, the organic phase was washed twice with water, the solvent was evaporated under reduced pressure, the residue was distilled under reduced pressure, and fractions at 92-96°C / 35mmHg were collected. 96.2 g were obtained. Gc: 99.08%. Yield: 65%

[0110] step 2

[0111]

[0112] Add embodiment 1 step 3 product (1-c) 3.0g (0.017mol) in 250ml there-necked flask, 5.37g (0.0363mol) (2-a), 3.38g (0.0408mol) anhydrous potassium carbonate, 0.1g potassium iodide, 50ml of DMF, and react in an oil bath at a constant temperature of 90°C for 7 hou...

Embodiment 3

[0117] Embodiment 3, compound shown in preparation formula I8

[0118]

[0119] step 1

[0120]

[0121] Put 90g (1mol) of 1,4-butanediol into a 1L three-necked flask, add 600ml of dichloromethane, 121g (1.2mol) of triethylamine, 0.2g of a polymerization inhibitor, and dropwise add 99.5g (1.1mol) of acryloyl chloride, After the addition was complete, the reaction was stirred at room temperature for 13 hours.

[0122] The precipitated salt was removed by filtration, the organic phase was washed twice with water, the solvent was evaporated under reduced pressure, the residue was distilled under reduced pressure, and fractions at 98-101°C / 33mmHg were collected. 46.2g were obtained. Gc: 90.08%. Yield: 32%

[0123] step 2

[0124]

[0125] 0.96g (0.00324mol) triphosgene is dropped in the 100ml there-necked flask, 20ml dichloromethane, add 1.27g (0.00884mol) the product (3-a) of step 1 and 5ml of 0.77g (0.00972mol) pyridine in the dropping funnel Dichloromethane solut...

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Abstract

The invention discloses a bicyclo[3,3,0]octane polymerizable compound. The general structural formula of the bicyclo[3,3,0]octane polymerizable compound is as shown in a formula I which is described in the specification. The compound as shown in the formula I has the advantages of good intersolubility with other monomers, good ultraviolet ray endurance capability, etc. As an RM, the bicyclo[3,3,0]octane polymerizable compound has the advantages of good intersolubility, a high voltage holding rate (VHR), high polymerization activity (few monomer residuals), etc., and is especially applicable as the RM to liquid crystal mixtures of a PSA (polymer-supported alignment) mode and a PS (polymer stabilization) mode. Meanwhile, the compound can be applied to a liquid crystal display including a polymer-stabilized blue phase and has good dissolvability and polymerisability; and a final product has no or tiny retardation effect.

Description

technical field [0001] The invention belongs to the field of liquid crystals and relates to a bicyclo[3,3,0]octane polymerizable compound. Background technique [0002] Polymerizable mesogenic units (RMs) are currently a very hot and important topic in the display industry, and their possible applications include polymer stabilized alignment (PSA) liquid crystal display, polymer stabilized blue phase (PS-BP) liquid crystal display and graphic Phase difference film (Pattern Retarder Film) and so on. [0003] The principle of PSA is being applied in different typical LC displays, such as PSA-VA, PSA-OCB, PS-IPS / FFS and PS-TN. Taking the most widely used PSA-VA display as an example, the pretilt angle of the liquid crystal cell can be obtained by the PSA method, and the pretilt angle has a positive impact on the response time. For PSA-VA displays, standard MVA or PVA pixel and electrode designs can be used, but if the electrodes are designed with a special pattern on one side...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C69/653C07C69/96C09K19/32G02F1/1333G02B27/22
Inventor 员国良赵磊赵利峰韩耀华华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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