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CN-122011082-A - Liquid crystal compound and application thereof

CN122011082ACN 122011082 ACN122011082 ACN 122011082ACN-122011082-A

Abstract

The present invention relates to liquid crystal compounds and their use. The liquid crystal compound has a structure shown in the formula I, has a relatively long rigid main structure, can obviously improve the dielectric anisotropy of a liquid crystal material, and improves the performance of the liquid crystal material.

Inventors

  • BAN QUANZHI
  • SHI ZHILIANG
  • LIANG XIANLI
  • YANG BO
  • HANG DEYU

Assignees

  • 北京云基科技股份有限公司

Dates

Publication Date
20260512
Application Date
20260301

Claims (10)

  1. 1. A liquid crystal compound having a structure as shown in formula I: ; wherein each X 1 、X 2 is independently selected from CH 2 , O, or S; R 1 、R 2 is each independently selected from any one or more of halo or unsubstituted C1-C12 alkyl, halo or unsubstituted C1-C12 alkoxy, halo or unsubstituted C3-C10 cycloalkyl, halo or unsubstituted C2-C12 alkenyl, halo or unsubstituted C2-C12 alkenyloxy; Ring a, ring B are each independently selected from any one or more of a halogenated or unsubstituted C6-C14 arylene, a halogenated or unsubstituted C5-C8 cycloalkylene, a halogenated or unsubstituted C5-C8 cycloalkenylene, a halogenated or unsubstituted C3-C8 saturated or unsaturated oxygenated heterocyclic group; Z 1 、Z 2 is each independently selected from the group consisting of a single bond, a double bond, -O-, C1-C4 alkylene, C1-C4 alkyleneoxy, -COO-, -OCO-, -O-C1-C4 alkylene-O-, and C2-C4 alkenylene, optionally, one or more hydrogen atoms of the C1-C4 alkylene, C1-C4 alkyleneoxy, and C2-C4 alkenylene are replaced with halogen atoms; m, n are each independently selected from 0, 1 or 2.
  2. 2. The liquid crystal compound according to claim 1, wherein each R 1 、R 2 is independently selected from any one or more of a halogenated or unsubstituted C1-C5 alkyl group, a halogenated or unsubstituted C1-C5 alkoxy group, a halogenated or unsubstituted C3-C8 cycloalkyl group, a halogenated or unsubstituted C2-C8 alkenyl group, a halogenated or unsubstituted C2-C8 alkenyloxy group; Preferably, R 1 、R 2 is each independently selected from any one or more of C1-C5 alkyl, C1-C5 fluoroalkyl, C1-C5 alkoxy, C1-C5 fluoroalkoxy, C3-C6 cycloalkyl, C3-C6 fluoroalkylene, C2-C4 alkenyl, C2-C4 fluoroalkenyl; Preferably, each R 1 、R 2 is independently selected from any one or more of methyl, ethyl, n-propyl, n-butyl, n-pentyl, fluoromethyl, fluoroethyl, fluoro-n-propyl, fluoro-n-butyl, fluoro-n-pentyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, fluoromethoxy, fluoroethoxy, fluoropropoxy, fluorobutoxy, fluoropentoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, fluorovinyl, fluoropropenyl, fluorobutenyl; Preferably, each R 1 、R 2 is independently selected from any one or more of methyl, ethyl, n-propyl, n-butyl, fluoromethyl, methoxy, ethoxy, propoxy, butoxy, vinyl.
  3. 3. The liquid crystal compound according to claim 1 or 2, wherein the rings a, B are each independently selected from any one or more of halogenated or unsubstituted 1, 4-phenylene, halogenated or unsubstituted 1, 4-cyclohexylene, halogenated or unsubstituted 1, 4-cyclohexenylene, halogenated or unsubstituted tetrahydropyranyl, halogenated or unsubstituted 1, 3-dioxanyl; Preferably, ring A, ring B are each independently selected from any one or more combinations of 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyranyl, 1, 3-dioxanyl, 1, 4-phenylene containing 1-4 fluoro substituents; preferably, ring a, ring B are each independently selected from any one of the following groups: 、 、 、 、 、 、 Or (b) 。
  4. 4. A liquid crystal compound according to any one of claims 1 to 3, wherein each Z 1 、Z 2 is independently selected from any one of a single bond, a double bond 、-O-、-CH 2 -、-CH 2 CH 2 -、-CH 2 O-、-OCH 2 -、-OCH 2 CH 2 -、-COO-、-OCO-、-O-CH 2 -O-、-O-CH 2 CH 2 -O-、-CH=CH-, optionally wherein one or more hydrogen atoms in -CH 2 -、-CH 2 CH 2 -、-CH 2 O-、-OCH 2 -、-OCH 2 CH 2 -、-O-CH 2 -O-、-O-CH 2 CH 2 -O-、-CH=CH- are replaced by fluorine atoms; Preferably, each Z 1 、Z 2 is independently selected from any one or a combination of single bond, double bond 、-O-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CH 2 CH 2 -、-COO-、-OCO-、-CHFO-、-OCHF-、-O-CH 2 -O-、-OCHFO-、-CF 2 -、-CHF-、-CH 2 -、-CHFCH 2 -、-CH 2 CHF-、-CHFCHF-、-CF 2 CH 2 -、-CH 2 CF 2 -、-CF 2 CHF-、-CHFCF 2 -、-CF 2 CF 2 -、-CH=CH-、-CF=CH-、-CH=CF-、-CF=CF-; Preferably, Z 1 、Z 2 is each independently selected from single bond 、-O-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CH 2 CH 2 -、-COO-、-OCO- or-CF 2 CF 2 -.
  5. 5. The liquid crystal compound according to any one of claims 1 to 4, wherein the liquid crystal compound has a structure as shown in any one of: , , , wherein R 1 、R 2 、Z 1 、Z 2 , ring A, ring B, X 1 、X 2 , m, n are as defined in formula I.
  6. 6. The liquid crystal compound according to any one of claims 1 to 5, wherein the liquid crystal compound has a structure as shown in any one of formula I-1 to formula I-43: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ; Wherein R 1 、R 2 、X 1 、X 2 is as defined in formula I.
  7. 7. The liquid crystal compound according to any one of claims 1 to 6, wherein the liquid crystal compound comprises a compound represented by any one of the following structures: , , , , , , , , , , , , , , , , , , , 。
  8. 8. A liquid crystal material composition comprising the liquid crystal compound of any one of claims 1-7; Preferably, the mass percentage of the liquid crystal compound in the liquid crystal material composition is 1-60%, preferably 1-40%, and more preferably 5-20%.
  9. 9. A liquid crystal display device comprising the liquid crystal compound according to any one of claims 1 to 7, or comprising the liquid crystal material composition according to claim 8; Preferably, the liquid crystal display device includes TN, ADS, VA, PSVA, FFS, IPS liquid crystal displays.
  10. 10. Use of a liquid crystal compound according to any one of claims 1 to 7 or a liquid crystal material composition according to claim 8 in the field of liquid crystal display; Preferably, the application comprises the use of the liquid crystal compound or the liquid crystal material composition in a liquid crystal display device; Preferably, the liquid crystal compound or the liquid crystal material composition is used as a liquid crystal material in the liquid crystal display device; Preferably, the liquid crystal display device includes TN, ADS, VA, PSVA, FFS, IPS liquid crystal displays.

Description

Liquid crystal compound and application thereof Technical Field The invention relates to the technical field of liquid crystal materials, in particular to a liquid crystal compound and application thereof. Background The liquid crystal material is a special organic compound with liquid fluidity and crystal optical anisotropy, and is a core functional material of Liquid Crystal Display (LCD) and a plurality of photoelectric devices. The application of the liquid crystal material as an environment material in the fields of information display materials, organic optoelectronic materials and the like has great research value and wide application prospect. The liquid crystal material itself plays an important role in improving the performance of the liquid crystal display, and particularly, the reduction of the rotational viscosity of the liquid crystal material and the increase of the dielectric anisotropy delta epsilon of the liquid crystal material will significantly improve the performance of the liquid crystal display. Therefore, to improve the performance of liquid crystal materials to meet new requirements, the study of the synthesis and structure-performance relationship of novel structure liquid crystal compounds has become an important task in the liquid crystal field. Disclosure of Invention In order to solve at least one of the technical problems, the invention develops a novel liquid crystal compound with dielectric anisotropy, which has the excellent characteristics of higher dielectric anisotropy, good liquid crystal intersolubility, proper rotational viscosity and the like, and can be used for improving the performance of a liquid crystal material. In addition, the invention also provides a liquid crystal material composition containing the liquid crystal compound and application of the liquid crystal compound and the liquid crystal material composition. In a first aspect, the present invention provides a liquid crystal compound having a structure as shown in formula I: ; wherein each X 1、X2 is independently selected from CH 2, O, or S; R 1、R2 is each independently selected from any one or more of halo or unsubstituted C1-C12 alkyl, halo or unsubstituted C1-C12 alkoxy, halo or unsubstituted C3-C10 cycloalkyl, halo or unsubstituted C2-C12 alkenyl, halo or unsubstituted C2-C12 alkenyloxy; Ring a, ring B are each independently selected from any one or more of a halogenated or unsubstituted C6-C14 arylene, a halogenated or unsubstituted C5-C8 cycloalkylene, a halogenated or unsubstituted C5-C8 cycloalkenylene, a halogenated or unsubstituted C3-C8 saturated or unsaturated oxygenated heterocyclic group; Z 1、Z2 is each independently selected from the group consisting of a single bond, a double bond, -O-, C1-C4 alkylene, C1-C4 alkyleneoxy, -COO-, -OCO-, -O-C1-C4 alkylene-O-, and C2-C4 alkenylene, optionally, one or more hydrogen atoms of the C1-C4 alkylene, C1-C4 alkyleneoxy, and C2-C4 alkenylene are replaced with halogen atoms; m, n are each independently selected from 0, 1 or 2. In the present invention, the halogenated or unsubstituted alkyl group is preferably linear, wherein "linear" specifically means that all carbon atoms constituting the alkyl group are on the same carbon chain. The halogenated or unsubstituted alkyl group can make the anisotropic arrangement of the above liquid crystal compound more ordered, so that it can have liquid crystal properties. "liquid crystal properties" refers to the ability of a substance to have liquid flowability at a given temperature and the anisotropic ordering of crystalline substances. In the present invention, a halogenated or unsubstituted alkoxy group may be regarded as a structure in which the above-mentioned halogenated or unsubstituted alkyl group is bonded to an oxygen atom (O). The halogenated or unsubstituted alkoxy group is also preferably linear, and the liquid crystal compound having the halogenated or unsubstituted linear alkoxy group can exhibit good liquid crystal properties. In the present invention, the halogenated or unsubstituted alkenyl group may be a linear alkenyl group or a branched alkenyl group, preferably a linear alkenyl group. The above liquid crystal compound having the halogenated or unsubstituted linear alkenyl group is easy to prepare, and it can exhibit good liquid crystal properties. In the present invention, the halogenated or unsubstituted alkenyloxy group may be a linear alkenyloxy group or a branched alkenyloxy group, and the linear alkenyloxy group is preferable. Among them, a halogenated or unsubstituted alkenyloxy group may be regarded as a structure in which a halogenated or unsubstituted alkenyl group is bonded to an oxygen atom. The substituent groups of the invention have proper carbon atom numbers, so that the liquid crystal compound shown in the formula I can be easily prepared, and the dielectric anisotropy value of the liquid crystal compound can be regulated and controlled within a wide range. In the present i