Fluoroboron pyrrole liquid crystal compound containing 8-(diphenylethinyl)-ester group flexible multi-element rings, preparation method and application thereof

A bisphenylacetylene and ester-based flexible technology, which is applied in the field of display materials, can solve the problems of lack of performance fluorescent dichroic dyes, achieve the effects of rich types, novel structures, and reduced response time

Inactive Publication Date: 2019-05-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problem of lack of fluorescent dichroic dyes with good performance in the prior art, the present invention provides a kind of fluorescent dye with green fluorescence, high molar coefficient, good dichroic ratio and order in liquid crystals. Parameters, fluorescent dichroic dyes suitable for liquid crystal display products and capable of improving response time

Method used

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  • Fluoroboron pyrrole liquid crystal compound containing 8-(diphenylethinyl)-ester group flexible multi-element rings, preparation method and application thereof
  • Fluoroboron pyrrole liquid crystal compound containing 8-(diphenylethinyl)-ester group flexible multi-element rings, preparation method and application thereof
  • Fluoroboron pyrrole liquid crystal compound containing 8-(diphenylethinyl)-ester group flexible multi-element rings, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of liquid crystal dye DC1

[0047](1) Synthesis of ethyl p-iodobenzoate (compound 1)

[0048]

[0049] Add 2.48g of p-iodobenzoic acid and 20ml of ethanol to a 50ml double-necked round-bottom flask for reaction, add a catalytic amount of concentrated sulfuric acid at the same time, heat to reflux, track and monitor by TLC until the reaction is complete, pour into water for extraction with dichloromethane, The excess solvent was removed under reduced pressure to obtain 2.76 g of light yellow oil, with a yield of 85%.

[0050] (2) Synthesis of 4-trimethylsilylethynyl-ethyl benzoate (compound 2)

[0051]

[0052] Add 276mg (8.5mmol) ethyl p-iodobenzoate, 2mL (10mmol) trimethylsilylacetylene, 70mg ditriphenylphosphine palladium dichloride, 150mg triphenylphosphine, and 80mg CuI as catalysts into a 50mL double-port round bottom In the flask, use 15mL of dry triethylamine as an acid-binding agent and solvent. Stir under nitrogen protection and heat to reflu...

Embodiment 2

[0069] Synthesis of liquid crystal dye DC2

[0070] In addition to using propyl bicyclohexyl methyl carbinol instead of pentyl bicyclohexyl carbinol in step (4), replace 4-ethynyl benzene pentyl carbinol with 4-ethynyl phenylpropyl bicyclohexyl methyl carbinol ester in step (6). Except for base bicyclohexylmethanol ester, other operating steps were the same as in Example 1 to obtain 427 mg of red solid with a yield of 62%.

[0071] 1 HNMR (400MHz, CDCl 3 )δ8.05(d, J=8.3Hz, 1H), 7.69(d, J=8.1Hz, 1H), 7.61(d, J=8.3Hz, 1H), 7.32(d, J=8.1Hz, 1H) ,5.99(s,1H),4.14(d,J=6.4Hz,1H),2.56(s,3H),1.88(s,1H),1.78(d,J=8.8Hz,2H),1.71(d, J=13.8Hz, 2H), 1.43(s, 3H), 1.29(dt, J=15.3, 7.7Hz, 2H), 1.18–1.11(m, 2H), 1.04(d, J=15.1Hz, 3H), 1.01–0.91(m,1H),0.87(t,J=7.3Hz,2H).

[0072] 13 CNMR (101MHz, CDCl 3 )δ161.29(s),151.10(s),138.20(s),135.88(s),130.74(s),127.71(s),126.80(s),125.54(s),124.83(s),123.60( s), 122.59(s), 118.87(s), 116.67(s), 86.60(s), 85.28(s), 65.65(s), 55.65(s), 48.69(s), 3...

Embodiment 3

[0075] Synthesis of liquid crystal dye DC3

[0076] In addition to replacing pentyl bicyclohexyl carbinol with cholesterol in step (4), and replacing 4-ethynyl phenylpentyl bicyclohexyl carbinol with 4-ethynyl benzene cholesteryl ester in step (6), other operation steps are the same Example 1, 560 mg of red solid was obtained with a yield of 67%.

[0077] 1 HNMR (400MHz, CDCl 3 )δ8.06(d, J=8.5Hz, 1H), 7.70(d, J=8.3Hz, 1H), 7.62(d, J=8.5Hz, 1H), 7.33(d, J=8.3Hz, 1H) ,6.01(s,1H),5.44(d,J=3.4Hz,1H),4.99–4.83(m,1H),2.58(s,3H),2.49(d,J=7.6Hz,1H),2.13– 1.96(m,2H),1.53(dd,J=13.1,6.6Hz,2H),1.45(s,3H),1.36(d,J=7.9Hz,1H),1.27(s,2H),1.09(s ,2H),1.07–0.96(m,2H),0.94(d,J=6.5Hz,2H),0.89(d,J=1.8Hz,2H),0.88(d,J=1.8Hz,2H),0.71 (s,1H).

[0078] 13 CNMR (101MHz, CDCl 3( s), 128.36(s), 127.26(s), 122.92(s), 121.42(s), 91.31(s), 90.08(s), 74.93(s), 56.72(s), 56.17(s), 50.08( s), 42.35(s), 39.77(s), 39.54(s), 38.24(s), 37.05(s), 36.68(s), 36.22(s), 35.82(s), 31.94(d, J=5.1 Hz), 28.25(s),...

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Abstract

The invention relates to fluoroboron pyrrole liquid crystal dye containing 8-(diphenylethinyl)-ester group flexible multi-element rings, a preparation method and application thereof. According to theinvention, boron fluoride complex dipyrrole methine is used as a matrix, a diphenylacetylene rigid structure is introduced into a No. 8 position through a Sonogashira coupling reaction, a series of BODIPY-type dichroic dye of the 8-methyl-(diphenylethinyl)-ester group flexible multi-element rings is designed and synthetized by connecting bicyclohexyl, cholesterol and other flexible multi-element rings with a diphenyl acetenyl group through an esterification reaction. The maximum emission wavelength of the compound in dichloromethane is all concentrated at about 525nm, so that the compound presents green fluorescence, and a good dichroic ratio and ordered parameters are shown in liquid crystal E7; the liquid crystal compound has a liquid crystal intermediate phase in the temperature range of 100-280 DEG C, and can be used for manufacturing liquid crystal display products, particularly, the liquid crystal compound is used as a guest dye for a guest host mode liquid crystal display; whenthe compound is added to E7 liquid crystal and used in a guest host display mode, the response time can be improved, and the effect of quick response can be achieved.

Description

technical field [0001] The invention relates to a class of fluoroboropyrrole liquid crystal compounds containing 8-(bisphenylethynyl)-ester group flexible multi-rings. The preparation method and application thereof belong to the field of display materials. Background technique [0002] In the electronic information industry chain, the liquid crystal display panel is in a high-end position, and it is also a key component in digital products such as computers and mobile communication terminals. The innovation of display technology can drive the development of informatization, so it is particularly important to strengthen the in-depth research on liquid crystal display panels. . [0003] The "guest-host" display is a new display mode emerging in recent years. The "guest-host" (GH) mode is a working mode that shows color changes, and was proposed by G. Heilmeier et al. almost simultaneously with the DS mode. Some dichroic dyes are doped in the nematic liquid crystal host mater...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00C09K19/40
CPCC09B57/00C09K11/06C09K19/34C09K19/3477C09K19/404C09K2019/0433C09K19/60C07F5/022C09K2323/031C07F5/027C09K19/04C09K2211/1022
Inventor 李晓莲潘柔辰
Owner DALIAN UNIV OF TECH
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