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Negative dielectric anisotropy liquid crystal compound, composition and display element

A technology of liquid crystal compounds and liquid crystal compositions, applied in liquid crystal materials, organic chemistry, nonlinear optics, etc., can solve problems such as easy crystallization, poor compatibility, and application constraints, and achieve good liquid crystal phase stability and low rotation Effect of Viscosity, Wide Liquid Crystal Phase Range

Pending Publication Date: 2022-04-01
XIAN MODERN CHEM RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been found in practical applications that due to the strong molecular rigidity of fluorine-substituted dibenzofuran and dibenzothiophene materials, their compatibility with most liquid crystals is very poor, and crystallization is very easy to occur in liquid crystal compositions. Applications are severely constrained

Method used

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  • Negative dielectric anisotropy liquid crystal compound, composition and display element
  • Negative dielectric anisotropy liquid crystal compound, composition and display element
  • Negative dielectric anisotropy liquid crystal compound, composition and display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1: Synthesis of 3-ethoxy-4,6-difluoro-7-((tetrahydro-2H-pyran-2-yl)methoxy)dibenzofuran (2OB(O)O1A)

[0079]

[0080] Step 1: Preparation of 2-(benzyloxy)-1-bromo-3-fluorobenzene (BrOBnG)

[0081]

[0082] Add 195.5 grams (1.023mol) of 2-fluoro-6-bromophenol, 282.5 grams (2.047mol) of potassium carbonate, 142.5 grams (1.13mol) of benzyl chloride and 1.0L DMF into a 2L three-necked flask, heat up to 75°C and stir the reaction 5 Hours, gas phase monitoring after no raw material remains, stop the reaction. Water was added to the reaction system, and extracted three times with n-heptane, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and spin-dried to obtain 280 g of liquid. Yield 97%, purity 98%.

[0083] Step 2: Preparation of 2'-(Benzyloxy)-4-ethoxy-2,3,3'-trifluoro-1,1'-biphenyl (2OYOBnG)

[0084]

[0085] In a 2L three-necked flask, 215.5 grams (1.07mol) of 2,3-difluoro-4-ethoxyphenylboronic acid, 272.5 grams (0.9...

Embodiment 2

[0107] Example 2: Synthesis of 3-butoxy-4,6-difluoro-7-((tetrahydro-2H-pyran-2-yl)methoxy)dibenzofuran (4OB(O)O1A)

[0108]

[0109] The method is similar to that of Example 1, except that in step 2, 2,3-difluoro-4-butoxyphenylboronic acid is used instead of 2,3-difluoro-4-ethoxyphenylboronic acid.

[0110] Structure Identification:

[0111] 1 H NMR (500MHz, CDCl 3 ):0.98~1.00(t,J=7.0Hz,3H),1.42~1.66(m,6H),1.72~1.75(m,1H),1.78~1.85(m,2H),1.89~1.93(m,1H ), 3.49~3.54(m,1H), 3.74~3.78(m,1H), 3.99~4.14(m,5H), 6.92~6.99(m,2H), 7.40~7.42(m,2H).

[0112] 13 C NMR (125MHz, CDCl 3 ): 13.8, 19.1, 23.0, 25.9, 28.2, 31.4, 68.5, 70.5, 74.3, 76.0, 111.3, 112.0, 114.4, 114.4, 120.2, 120.2, 138.2, 140.2, 144.7, 144.8, 146.3, 146.5.

[0113] MS m / z(RI,%):390.4(M + ,46), 236.2(100), 99.2(58), 292.2(17).

[0114] Thermal performance test: Cr 93.78I.

Embodiment 3

[0115] Example 3: Synthesis of 3-ethoxy-4,6-difluoro-7-((tetrahydro-2H-pyran-2-yl)methoxy)dibenzothiophene (2OB(S)O1A)

[0116]

[0117] Step 1: Preparation of 4'-ethoxy-2',3,3'-trifluoro-[1,1'-biphenyl]-2-yl triflate (2OYOSO2CF3G)

[0118]

[0119] Add 113 grams (421.6 mmol) of 2OYOHG, 72.4 grams (716.8 mmol) of triethylamine and 600 mL of dichloromethane into a three-necked flask, and after the system cools down to 5-10°C, start to add 166.5 grams (590.4 mmol) of trifluoromethanesulfonate dropwise After the addition of acid anhydride was completed, the reaction was continued to be stirred for 1 hour, and then the reaction was stopped, and water was slowly added dropwise to the system to quench it. After dichloromethane was extracted three times, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and spin-dried, and recrystallized from n-heptane to obtain 126 g of a white solid with a yield of 74.7% and a purity of 92%.

[0120] Step 2: ...

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Abstract

The invention discloses a liquid crystal compound with negative dielectric anisotropy, a composition and a display element, and the structural general formula is shown in the formula I. The liquid crystal compound disclosed by the invention has remarkably improved intermiscibility and a relatively large negative dielectric anisotropy value. The composition containing the liquid crystal compound has good low-temperature liquid crystal phase stability and low rotary viscosity, and is suitable for IPS, FFS, VA, PSVA and other liquid crystal display devices.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and in particular relates to a liquid crystal compound with negative dielectric anisotropy, a composition and a display element. Background technique [0002] Liquid crystal displays have the advantages of flat panels, low power consumption, light weight, and no radiation, and are developing rapidly in the field of information display. Liquid crystal displays utilize the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials to realize display functions. Liquid crystal materials with negative dielectric anisotropy Δε (Δε=ε∥-ε⊥), referred to as negative liquid crystals, can be applied to vertical alignment (VA) mode, in-plane switching mode (IPS), fringe electric field switching mode (FFS). Compared with liquid crystal materials with positive dielectric anisotropy Δε, negative liquid crystals have relatively small Δε values ​​and high viscosity. ...

Claims

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Application Information

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IPC IPC(8): C07D407/12C07D409/12C09K19/34C09K19/44G02F1/1333
Inventor 李建莫玲超万丹阳杜渭松高嫒嫒邓登李娟利胡明刚车昭毅张璐陆涛
Owner XIAN MODERN CHEM RES INST
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