TWI804732B - Polymerizable compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents

Abstract

The present invention relates to a polymerizable compound, a liquid crystal composition, a liquid crystal display element and a liquid crystal display. The structure of the polymerizable compound of the present invention is shown in the following formula I, and the liquid crystal composition comprising the polymerizable compound has a faster polymerization rate and a lower residual amount, and is applied to PS- (polymer stabilization) or PSA- (polymer When used in stable alignment) type liquid crystal display elements, it can reduce afterimages and improve product quality.

Description

Polymerizable compound, liquid crystal composition, liquid crystal display element and liquid crystal display

The invention belongs to the field of liquid crystal display technology, and in particular relates to a polymerizable compound, a liquid crystal composition containing the polymerizable compound, and a liquid crystal display element or a liquid crystal display containing the polymerizable compound or the liquid crystal composition.

With the development of display technology, liquid crystal display (Liquid Crystal Display, LCD) and other flat display devices are widely used in mobile phones, TVs, Various consumer electronic products such as personal digital assistants, digital cameras, notebook computers, and desktop computers have become the mainstream of display devices.

Reactive liquid crystal (Reactive Mesogen, RM) is currently a very popular and important research direction in the liquid crystal display industry. Its possible application fields include polymer stabilized alignment (PSA) liquid crystal display, polymer stabilized blue phase (PS-BP) liquid crystal display And patterned bit phase difference film (Pattern Retarder Film) and so on.

However, the application of liquid crystal compounds mixed with RMs in PSA mode displays still has some disadvantages. First of all, not all RMs are suitable for PSA displays so far; at the same time, if UV light (Ultraviolet light) is used without adding photoinitiators to polymerize RMs, fewer RM types can be selected. Generally, the liquid crystal composition composed of liquid crystal compound and RM needs to go through two stages of ultraviolet light irradiation process in the preparation process of liquid crystal display element or liquid crystal display, so that RM polymerization. In the prior art, the RM polymerization process takes a long time, and more RM remains in the liquid crystal composition after polymerization, which affects the efficiency and quality of the preparation of liquid crystal display elements or liquid crystal displays.

In order to overcome the problems of low polymerization rate of reactive liquid crystals (RM) and many residual RMs in the liquid crystal composition, and solve the problems such as the unsatisfactory photoelectric properties of liquid crystal display elements or liquid crystal displays that lead to high defect rates, the inventors have conducted in-depth research and found that The present invention has been accomplished by being able to solve at least one of the aforementioned problems by containing the polymerizable compound of the present invention in a liquid crystal composition.

Specifically, the present invention includes the following content: the first aspect of the present invention provides a polymerizable compound represented by formula I,

3； Sp₁、Sp₂、Sp₃、Sp₄、Z₁、Z₂各自獨立地表示單鍵、具有1至25個C原子的直鏈烷基、具有3至25個C原子的支鏈烷基、具有3至25個C原子的環狀烷基、具有2至25個C原子的烯基或具有2至25個C原子的炔基，且其中一個或多個不相鄰的-CH₂-基團任選地被-O-、-S-、-CO-、-CO-O-、-O-CO-、-O-CO-O-取代，其中一個或多個H原子任選被F原子或Cl原子取代；Sp₅表示具有1至25個C原子的直鏈烷基、具有3至25個C原子的支鏈烷基、具有3至25個C原子的環狀烷基、具有2至25個C原子的烯基或具有2至25個C原子的炔基，且其中一個或多個不相鄰的-CH₂-基團任選地被-O-、-S-、-CO-、-CO-O-、-O-CO-、-O-CO-O-取代，其中一個或多個H原子任選被F原子或Cl原子取代；P₁、P₂、P₃、P₄各自獨立地表示可聚合基團。 Wherein, L ₁ , L ₂ , L ₃ , and L ₄ each independently represent an F atom, a Cl atom, -CN, a straight chain alkyl group having 1 to 25 C atoms, a branched chain alkyl group having 3 to 25 C atoms A group, a cyclic alkyl group having 3 to 25 C atoms, an alkenyl group having 2 to 25 C atoms or an alkynyl group having 2 to 25 C atoms, wherein one or more non-adjacent -CH ₂ - The group is optionally substituted by -O-, -S-, -NH-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, and one or more of the H Atoms are optionally substituted by halogen atoms; r ₁ , r ₃ each independently represent 0, 1, 2, 3 or 4; r ₂ , r ₄ each independently represent 0, 1, 2 or 3; x ₁ , x ₂ , x ₃ , x ₄ independently represent 0, 1 or 2, and x ₁ +x ₂ +x ₃ +x ₄

3; Sp ₁ , Sp ₂ , Sp ₃ , Sp ₄ , Z ₁ , Z ₂ each independently represent a single bond, a straight-chain alkyl group with 1 to 25 C atoms, a branched chain alkane with 3 to 25 C atoms A group, a cyclic alkyl group having 3 to 25 C atoms, an alkenyl group having 2 to 25 C atoms, or an alkynyl group having 2 to 25 C atoms, and wherein one or more non-adjacent -CH ₂ The - group is optionally substituted by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, wherein one or more H atoms are optionally replaced by F atom or Cl atom is substituted; Sp ₅ represents the linear alkyl group with 1 to 25 C atoms, the branched chain alkyl group with 3 to 25 C atoms, the cyclic alkyl group with 3 to 25 C atoms, with Alkenyl with 2 to 25 C atoms or alkynyl with 2 to 25 C atoms, wherein one or more non-adjacent -CH ₂ - groups are optionally replaced by -O-, -S-, - CO-, -CO-O-, -O-CO-, -O-CO-O-substituted, wherein one or more H atoms are optionally replaced by F atoms or Cl atoms; P ₁ , P ₂ , P ₃ , P ₄ each independently represent a polymerizable group.

The second aspect of the present invention provides a liquid crystal composition, which contains one or more polymerizable compounds represented by formula I.

The third aspect of the present invention provides a liquid crystal display element or a liquid crystal display, the liquid crystal display element or liquid crystal display comprising one or more polymerizable compounds represented by formula I or comprising one or more polymerizable compounds represented by formula I liquid crystal composition.

Compared with the conventional technology, the polymerizable compound represented by formula I of the present invention has a fast polymerization rate when it is verified with the same liquid crystal composition, can shorten the operation process time, improve production efficiency, and can save energy and reduce costs. At the same time, the amount of residual polymerization is low, which is conducive to improving the display quality and reducing the defective rate of products.

Fig. 1 shows the ^1h -NMR spectrogram of polymerizable compound shown in formula I-1-1;

The present invention discloses a polymerizable compound represented by the above formula I.

3；Sp₁、Sp₂、Sp₃、Sp₄、Z₁、Z₂各自獨立地表示單鍵、碳原子數為1-10的烷基、碳原子數為2-10的烯基或碳原子數為2-10的炔基，其中一個或多個不相鄰的-CH₂-基團任選地被-O-、-CO-、-CO-O-、-O-CO-取代，一個或多個H原子任選被F原子取代；Sp₅表示碳原子數為1-10的烷基、碳原子數為2-10的烯基或碳原子數為2-10的炔基，其中一個或多個不相鄰的-CH₂-基團任選地被-O-、-CO-、-CO-O-、-O-CO-取代，一個或多個H原子任選被F原子取代； P₁、P₂、P₃、P₄各自獨立地表示

、

、

、

、

、

In the polymerizable compound disclosed in the present invention, preferably, in the compound represented by formula I: L ₁ , L ₂ , L ₃ , and L ₄ each independently represent an alkyl group with 1-5 carbon atoms, fluorine-substituted Alkyl group with 1-5 carbon atoms, alkenyl group with 2-5 carbon atoms, alkoxy group with 1-5 carbon atoms, alkoxy group with 1-5 carbon atoms substituted by fluorine, F atom or Cl atom; r ₁ , r ₃ each independently represent 0, 1 or 2; r ₂ , r ₄ each independently represent 0 or 1; x ₁ , x ₂ , x ₃ , x ₄ each independently represent 0 or 1, and x ₁ +x ₂ +x ₃ +x ₄

3; Sp ₁ , Sp ₂ , Sp ₃ , Sp ₄ , Z ₁ , and Z ₂ each independently represent a single bond, an alkyl group with 1-10 carbon atoms, an alkenyl group with 2-10 carbon atoms, or a carbon atom 2-10 alkynyl groups, wherein one or more non-adjacent -CH ₂ - groups are optionally substituted by -O-, -CO-, -CO-O-, -O-CO-, one or multiple H atoms are optionally substituted by F atoms; Sp ₅ represents an alkyl group with 1-10 carbon atoms, an alkenyl group with 2-10 carbon atoms or an alkynyl group with 2-10 carbon atoms, one of which or more non-adjacent -CH ₂ - groups are optionally substituted by -O-, -CO-, -CO-O-, -O-CO-, and one or more H atoms are optionally substituted by F atoms ; P ₁ , P ₂ , P ₃ , and P ₄ independently represent

,

,

,

,

,

The polymerizable compound disclosed in the present invention, more preferably, is selected from the group consisting of compounds represented by the following formula I-1-1 to formula I-17-3,

I-4-11 I-4-12

I-4-11I-4-12

The present invention also provides a liquid crystal composition comprising one or more of the aforementioned polymerizable compounds of the present invention.

The liquid crystal composition as one aspect of the present invention contains the compound represented by the aforementioned formula I. In addition to the compound represented by the formula I, the liquid crystal composition may contain liquid crystal compounds other than the compound represented by the formula I and other additive materials.

Preferably, the liquid crystal composition of the present invention further comprises one or more compounds represented by the following formula II and one or more compounds represented by the following formula III,

、

各自獨立地表示

或

； 式III中，R₃、R₄各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基，且R₃、R₄中任意一個或多個不相鄰的-CH₂-任選被亞環戊基、亞環丁基或亞環丙基取代；Z₁、Z₂各自獨立地表示單鍵、-CH₂CH₂-、-CH₂O-或-OCH₂-；

、

各自獨立地表示

、

、

、

、

m₁表示1或2，當m₁表示2時，

相同或不同； n₁表示0、1或2，當n₁表示2時，

相同或不同。 In formula II, R ₁ and R ₂ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, Alkoxy group with 1-10 carbon atoms substituted by fluorine, alkenyl group with 2-10 carbon atoms, alkenyl group with 2-10 carbon atoms substituted by fluorine, and alkenyl group with 3-8 carbon atoms Alkenyloxy or fluorine-substituted alkenyloxy with 3-8 carbon atoms;

,

express independently

or

In formula III, R ₃ and R ₄ independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, and an alkoxy group with 1-10 carbon atoms , alkoxy group with 1-10 carbon atoms substituted by fluorine, alkenyl group with 2-10 carbon atoms, alkenyl group with 2-10 carbon atoms substituted with fluorine, 3-8 carbon atoms Alkenyloxy or alkenyloxy with 3-8 carbon atoms substituted by fluorine, and any one or more non-adjacent -CH ₂ - in R ₃ and R ₄ is optionally replaced by cyclopentylene, Substituted by cyclobutylene or cyclopropylene; Z ₁ and Z ₂ each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O- or -OCH ₂ -;

,

express independently

,

,

,

,

m ₁ means 1 or 2, when m ₁ means 2,

same or different; n ₁ means 0, 1 or 2, when n ₁ means 2,

same or different.

By containing the combination of the compound shown in the formula II and the compound shown in the formula III in the liquid crystal composition of the present invention, the obtained liquid crystal composition has a low rotational viscosity, which is beneficial to improve the liquid crystal composition. The reaction speed of the compound, and has a negative dielectric anisotropy, which can adjust the driving voltage of the composition.

In the present invention, the total mass of other compounds other than the compound shown in formula I is recorded as 100%, and the percentage of the ratio between the mass of the compound shown in formula I and the total mass of other compounds is recorded as formula I in the liquid crystal composition Mass fractions of indicated compounds. For example, when the liquid crystal composition only contains compounds shown in formula I, formula II and formula III, the total content of compounds shown in formula II and formula III is recorded as 100%, and the amount of compound shown in formula I The percentage of the ratio to the total mass of the compounds represented by formula II and formula III is recorded as the mass fraction of the compound represented by formula I.

In the liquid crystal composition of the present invention, preferably, the compound represented by the aforementioned formula II is selected from the group consisting of compounds represented by formula II-1 to formula II-17,

Preferably, the compound represented by the aforementioned formula III is selected from the group consisting of compounds represented by formula III-1 to formula III-15,

Wherein, R ₃₁ and R ₄₁ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, a fluorine-substituted Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms An alkenyloxy group with 3-8 carbon atoms substituted by oxo or fluorine, and any one or more non-adjacent -CH ₂ - in the groups represented by R ₃ and R ₄ is optionally replaced by a cyclopentylene group , cyclobutylene or cyclopropylene.

In the liquid crystal composition disclosed in the present invention, preferably, it also contains one or more compounds represented by formula IV,

Wherein, R ₅ and R ₆ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, a fluorine-substituted Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms Alkenyloxy group with 3-8 carbon atoms substituted by oxo or fluorine, and any one or more non-adjacent -CH ₂ - in R ₅ and R ₆ is optionally replaced by cyclopentylene, cyclobutylene group or cyclopropylene; W represents -O-, -S- or -CH ₂ O-.

By containing the compound shown in the aforementioned formula IV in the liquid crystal composition of the present application, by To enable the liquid crystal composition to have relatively large negative dielectric anisotropy, it is beneficial to reduce the driving voltage of the element.

其中，R₅₁、R₆₁表示碳原子數為1-6的烷基；本發明公開的液晶組合物中，較佳地，還包含一種或多種式V所示的化合物，

Further, the compound shown in the aforementioned formula IV is selected from the compounds shown in formula IV-1 to formula IV-10,

Among them, R ₅₁ and R ₆₁ represent an alkyl group with 1-6 carbon atoms; the liquid crystal composition disclosed in the present invention preferably further contains one or more compounds represented by formula V,

、

各自獨立地表示

、

或

。 Wherein, R ₇ and R ₈ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, or an alkyl group with 1-10 carbon atoms substituted by fluorine. Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms Alkenyloxy group with 3-8 carbon atoms substituted by oxy group or fluorine;

,

express independently

,

or

.

其中，R₇₁、R₈₁各自獨立的表示碳原子數為2-6的烷基或碳原子數為2-6的烯基；其中，做為碳原子數為2-6的烯基可以列舉出例如乙烯基、2-丙烯基或者3-戊烯基；R₈₂表示碳原子數為1-5的烷氧基；通過在本發明的液晶組合物中含有式V所示的化合物，能夠獲得高的清晰點、高的彈性常數，尤其是展曲彈性常數K₃₃，有利於提升液晶組合物的參數性能。 Further, the compound represented by the above formula V is preferably selected from the group consisting of compounds represented by formula V-1 to formula V-4,

Among them, R ₇₁ and R ₈₁ each independently represent an alkyl group with 2-6 carbon atoms or an alkenyl group with 2-6 carbon atoms; among them, the alkenyl group with 2-6 carbon atoms can be listed For example vinyl, 2-propenyl or 3-pentenyl; R ₈₂ represents the alkoxyl group that carbon number is 1-5; By containing the compound shown in formula V in the liquid crystal composition of the present invention, can obtain high The clear point and high elastic constant, especially the splay elastic constant K ₃₃ , are beneficial to improve the parameter performance of the liquid crystal composition.

其中，R₉、R₁₀各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基；

表示

、

或

。 In the liquid crystal composition disclosed in the present invention, preferably, it also contains one or more compounds represented by formula VI,

Wherein, R ₉ and R ₁₀ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, or an alkyl group with 1-10 carbon atoms substituted by fluorine. Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms Alkenyloxy group with 3-8 carbon atoms substituted by oxy group or fluorine;

express

,

or

.

其中，R₉₁、R₁₀₁各自獨立地較佳表示碳原子數為2-6的烷基或原子數為2-6的烯基。 Further, the compound represented by the aforementioned formula VI is preferably selected from the group consisting of compounds represented by the formulas VI-1 to VI-3,

Among them, R ₉₁ and R ₁₀₁ each independently preferably represent an alkyl group with 2-6 carbon atoms or an alkenyl group with 2-6 atoms.

The clear point of the liquid crystal composition can be improved by including the compound selected from the group consisting of formulas VI-1 to VI-3 in the liquid crystal composition.

Preferably, the liquid crystal composition of the present invention comprises: 0.01-1% of the compound shown in formula I, 30-60% of the compound shown in formula II, 30-60% of the compound shown in formula III, 1- 10% of the compound shown in formula VI; preferably, the liquid crystal composition of the present invention comprises: 0.01-1% of the compound shown in formula I, 15-60% of the compound shown in formula II, 20-60% The compound shown in the formula III, 1-15% of the compound shown in the formula IV, 1-10% of the compound shown in the formula VI; preferably, the liquid crystal composition of the present invention comprises: 0.03-0.2% of the formula Compound shown in I, 35-45% compound shown in formula II, 45-50% compound shown in formula III, 2-10% compound shown in formula IV, 2-5% compound shown in formula VI.

Preferably, the liquid crystal composition of the present invention comprises according to mass percentage: 0.01-1% of the compound shown in formula I, 15-60% of the compound shown in formula II, 20-60% of the compound shown in formula III, 1- 30% of the compound shown in formula V, 1-10% of the compound shown in formula VI; preferably, the liquid crystal composition of the present invention comprises: 0.03-0.2% of the compound shown in formula I, 25-40% Compound shown in formula II, 35-50% compound shown in formula III, 5-20% compound shown in formula V, 2-5% compound shown in formula VI.

Preferably, the liquid crystal composition of the present invention comprises according to mass percentage: 0.01-1% of the compound shown in formula I, 15-60% of the compound shown in formula II, 2.0-60% of the compound shown in formula III, 1- 15% The compound shown in the formula IV, 1-30% of the compound shown in the formula V, 1-10% of the compound shown in the formula VI; preferably, the liquid crystal composition of the present invention comprises: 0.03-0.2% of the compound shown in the formula The compound shown in I, the compound shown in 20-40% formula II, the compound shown in 30-50% formula III, the compound shown in 2-10% formula IV, the compound shown in 5-20% formula V, 2 -5% of the compound shown in formula VI.

In the liquid crystal composition disclosed in the present invention, dopants with various functions can also be added. In the case of containing dopants, the content of the dopant is preferably 0.01-1% by mass in the liquid crystal composition. , These dopants include, for example, antioxidants, ultraviolet absorbers, and chiral agents.

t表示1-10的整數。 Examples of antioxidants and ultraviolet absorbers include,

t represents an integer of 1-10.

The liquid crystal display element of the present invention comprises the aforementioned polymerizable compound of the present invention or the aforementioned liquid crystal composition of the present invention, and the display element is an active matrix display element or a passive matrix display element.

Preferably, the liquid crystal display element of the present invention is preferably an active matrix liquid crystal display element.

Preferably, the active matrix display element of the present invention is a PSVA-TFT or IPS-TFT liquid crystal display element.

For the aforesaid liquid crystal display element of the present invention, as long as the compound shown in the formula I of the present invention is contained in the liquid crystal composition used in it, then its structure is not limited, and those skilled in the art can determine the desired performance Select the appropriate structure of the liquid crystal display element.

As an embodiment of the liquid crystal display of the present invention, can enumerate, for example following structure: comprise the first substrate, the second substrate, and the liquid crystal composition that is arranged between the first substrate and the second substrate, the first substrate It is arranged parallel to the second substrate, an alignment layer is provided on the side of the first substrate and the second substrate close to the liquid crystal composition, the first substrate is provided with a common electrode, and the second substrate is provided with a pixel electrode, and the first substrate and the second substrate are provided with an alignment layer. Spacers are interspersed between the substrates.

As the preparation method of the liquid crystal display of the present invention, those skilled in the art can select an appropriate method for preparation according to common knowledge in the field. As an example of the preparation method of the liquid crystal display of the present invention, for example, the preparation method comprising the following steps: uniformly coating the alignment material on the surface of the first substrate and the second substrate, the alignment material can be selected from polyimide, for uniform The coated alignment material is heated and cured at 210-250°C to form an alignment layer; spacers are spread on the surface of the second substrate, and frame glue is coated along the edge of the first substrate, and cured at 100°C-150°C ; The first substrate and the second substrate are arranged oppositely, and bonded to form a structure with an interlayer space; the liquid crystal composition is injected into the interlayer space between the first substrate and the second substrate, sealed and solidified, so as to seal the liquid crystal composition in the second substrate between the first substrate and the second substrate, and carry out power supply and ultraviolet light irradiation at the same time. The ultraviolet light irradiation is divided into two stages of the first stage ultraviolet light irradiation (UV1) and the second stage ultraviolet light irradiation (UV2). In the UV1 stage, the wavelength of ultraviolet light is 360nm-370nm, and the irradiance of ultraviolet light is 60-72mw/cm ² . The time for ultraviolet light irradiation may be, for example, 50-65s, preferably 50-60s.

The second-stage light irradiation (UV2) is performed after the first-stage light irradiation is completed, and the light used in UV2 includes, for example, ultraviolet light. In the second stage of ultraviolet irradiation (UV2), the wavelength of ultraviolet light is, for example, 360nm-370nm, and the irradiance of ultraviolet light used in the UV2 stage is, for example, 3-8mw/cm ² . By adopting such irradiance, the unpolymerized compound represented by formula I can be slowly and completely polymerized, and the conversion rate of the polymerizable compound can be improved, so that there is no residue of the polymerizable compound in the liquid crystal composition. And because the polymerization is slow, the process has no effect on the pretilt angle already formed. The ultraviolet light irradiation time in the UV2 stage can be, for example, 100-150 min.

Example

In order to illustrate the present invention more clearly, the present invention will be further described below in conjunction with preferred embodiments and accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. Those skilled in the art should understand that the content specifically described below is illustrative rather than restrictive, and should not limit the protection scope of the present invention.

In the present invention, the preparation method is a conventional method unless otherwise specified, and the raw materials used can be obtained from open commercial channels if not otherwise specified, and the percentages all refer to mass percentages, and the temperature is degrees Celsius (° C.), and the liquid crystal compound also becomes Liquid crystal monomer, the specific meanings and test conditions of other symbols are as follows: Cp means liquid crystal clear point (°C), tested by DSC quantitative method; Δn means optical anisotropy, Δn=n _e -n _o , where n _o is ordinary light , ne _is the refractive index of extraordinary light, the test condition is 25±2°C, 589nm, Abbe refractometer test; Δε represents dielectric anisotropy, Δε=ε∥-ε⊥, where, ε∥ is the dielectric constant parallel to the molecular axis, ε⊥ is the dielectric constant perpendicular to the molecular axis, the test condition is 25±0.5°C, 20 micron vertical cell, INSTEC: ALCT-IR1 test; VHR means voltage retention rate (%) , The test condition is 20±2℃, the voltage is ±5V, the pulse width is 10ms, and the voltage hold time is 16.7ms. The test equipment is TOYO Model6254 liquid crystal performance comprehensive tester; _γ1 means rotational viscosity (mPa.s), the test condition is 25±0.5°C, 20 micron vertical cell, INSTEC: ALCT-IR1 test.

In the embodiment of the present invention, the equipment and instruments used for the preparation of the liquid crystal composition are as follows: the preparation method of the liquid crystal composition is as follows: put each polymerizable compound into a stainless steel beaker after weighing according to a certain proportion, and put each polymerizable compound into a stainless steel beaker. The stainless steel beaker of the compound is heated and melted on a magnetic stirring apparatus, and after the polymerizable compound in the stainless steel beaker is melted, a magnetic rotor is added to the stainless steel beaker, the mixture is stirred evenly, and the liquid crystal composition is obtained after cooling to room temperature.

The preparation method of the liquid crystal display element in the embodiment of the present invention is as follows: First, uniformly coat the alignment material on the surface of the first substrate and the second substrate, the alignment material can be polyimide, and heat and cure the evenly coated alignment material , the heating temperature is 230°C to form an alignment layer; secondly, spacers are spread on the surface of the second substrate, and frame glue is coated along the edge of the first substrate, and cured at 120°C; then, the first substrate and the second The substrates are arranged oppositely and bonded to form a structure with interlayer space; finally, the liquid crystal composition is injected into the interlayer space between the first substrate and the second substrate, sealed and cured, so that the liquid crystal composition is sealed on the first substrate and the second substrate Between, and at the same time, power-on, ultraviolet light irradiation. The ultraviolet light irradiation is divided into two stages, including the first stage ultraviolet light irradiation (UV1) and the second stage ultraviolet light irradiation (UV2). In the UV1 stage, the ultraviolet light is irradiated with a wavelength of 365nm and an irradiance of 64mw/ ^cm2 . After the first stage of light irradiation is completed, the second stage of light irradiation (UV2) is carried out. In UV2, ultraviolet light with a wavelength of 365nm is used. The irradiance is 5mw/cm ² , and the light irradiation time is 100-150mm.

The structures of the liquid crystal monomers used in the embodiments of the present invention are represented by codes, and the code representation methods of liquid crystal ring structures, terminal groups, and linking groups are shown in Table 1 and Table 2 below.

，其代碼為CC-Cp-V1；

，其代碼為PGP-Cpr1-2；

，其代碼為CPY-2-O2；

，其代碼為CCY-3-O2；

，其代碼為COY-3-O2；

，其代碼為CCOY-3-O2；

，其代碼為Sb-CpO-O4；

，其代碼為Sc-CpO-O4；

，其代碼為COYL-Cprl-O2；

，其代碼為COYL-1-OV1。 Example:

, whose code is CC-Cp-V1;

, whose code is PGP-Cpr1-2;

, whose code is CPY-2-O2;

, whose code is CCY-3-O2;

, whose code is COY-3-O2;

, whose code is CCOY-3-O2;

, whose code is Sb-CpO-O4;

, whose code is Sc-CpO-O4;

, whose code is COYL-Cprl-O2;

, whose code is COYL-1-OV1.

Below adopt following specific embodiment to illustrate the present invention:

[Liquid crystal compound]

Compound shown in formula I of the present invention can be synthesized according to following scheme:

Among them, L ₁ , L ₂ , L ₃ , L ₄ , r ₁ , r ₃ , r ₂ , r ₄ , x ₁ , x ₂ , x ₃ , x ₄ , Sp 1 , Sp ₂ , Sp ₃ , _{Sp 4 ,} Sp ₅ , Z ₁ , Z ₂ , P ₁ , P ₂ , P ₃ , and P ₄ are each independently as defined in the polymerizable compound shown in the above formula I; S ₁ and S ₂ each independently represent an aldehyde group, Hydroxyl, carboxyl; B ₁ , B ₂ , B ₃ , and B ₄ each independently represent a protecting group for hydroxyl.

The raw materials and reagents in the general synthesis formula can be purchased through conventional synthesis or commercial channels. Means such as such method principle, operation process, conventional post-treatment, silica gel column, recrystallization and purification are well known to those skilled in the art. The synthesis process can be realized to obtain the target product.

The reactions of all the steps of the above-mentioned methods are carried out in a solvent; the solvent is selected from tetrahydrofuran, N,N-dimethylformamide, ethanol, methanol, methylene chloride, acetone, toluene and deionized water at least A sort of.

Example 1

The structural formula of the compound is shown in the following formula I-1-1,

Its preparation route is as follows:

The specific operation process of preparation:

Intermediate 3

Under the protection of nitrogen, 0.4 mol of intermediate 1, 0.4 mol of intermediate 2, 2.0 L of toluene, 0.7 L of water, 0.45 mol of potassium carbonate, and 0.5 g of catalyst were put into a 5 L three-necked flask, and heated to reflux for 3 hours. quiet The liquid was separated, separated by column chromatography, and recrystallized from toluene/ethanol to obtain compound 3 as a yellow solid. HPLC: 92%, yield Y=80%.

Intermediate 4

Under the protection of nitrogen, put 0.22mol of intermediate 3, 0.15mol of 1,2-dibromoethane, 0.25mol of anhydrous potassium carbonate, 1.2L of DMF into a 2L three-necked flask, and react at 120°C under the protection of _N2 . Hour. After the reaction is complete, cool down, pour into ice water while stirring, stir for 30 minutes, filter, and beat with 0.5L petroleum ether to obtain compound 4, HPLC: 96%, yield Y=86%.

Intermediate 5

Add 0.08mol of intermediate 4, 7g of Pd/C, 0.3L of THF and 0.3L of EtOH into a 1L three-neck flask, replace with N ₂ three times, H ₂ three times, hydrodebenzylation at 40°C, and react for 6 hours. After the reaction was completed, filter with diatomaceous earth, concentrate the filtrate, beat PE:EA=10:1, and stir for 10 minutes to obtain compound 5, HPLC: 98%, yield Y=80%.

Compound I-1-1

Put 0.03mol of intermediate 5, 0.2mol of triethylamine, and 0.2L of DCM into a 500ml three-necked flask, and add 0.2mol of methacryloyl chloride dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 3 hours. After the reaction is complete, add water, extract the aqueous phase with DCM, combine the organic phases, wash once with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate the filtrate, dissolve 5 times of toluene at 45°C, pass through a 50 g silica gel column, and wash the column with 3 times of toluene. Concentrate, heat to dissolve with 3 times of toluene and 3 times of ethanol, refrigerate at -20°C for 4 hours, filter with suction, recrystallize three times according to the same method, and dry to obtain white solid compound I-1-1, HPLC: 99.1%, yield Y=45%. The ^1h -NMR spectrum of compound I-1-1 is shown in Figure 1.

Example 2

The structural formula of the compound is shown in the following formula I-2-1,

Its preparation route is as follows:

The specific operation process of preparation:

Intermediate 3

Refer to the synthesis of intermediate 1 in the route of compound I-1-1.

Intermediate 7

The raw material 1,2-dibromopropane is replaced by 1,2-dibromohexane, and the synthesis method refers to the synthesis of intermediate 4 in Example 1.

Intermediate 8

The synthesis method refers to the synthesis of intermediate 5 in Example 1.

Compound I-2-1

The synthesis method refers to the synthesis of compound I-1-1 in Example 1.

Example 3

The structural formula of the compound is shown in the following formula I-4-1,

Its preparation route is as follows:

The specific operation process of preparation:

Intermediate 11

Under the protection of nitrogen, 0.4 mol of intermediate 1, 0.4 mol of intermediate 10, 2.0 L of toluene, 0.7 L of water, 0.45 mol of potassium carbonate, and 0.4 g of catalyst were put into a 5 L three-necked flask, and heated to reflux for 3 hours. The liquid was separated by standing, separated by column chromatography, and recrystallized from toluene/ethanol to obtain compound 11 as a light yellow solid. HPLC: 94%, yield Y=75%.

Intermediate 12

Under the protection of nitrogen, put 0.15mol of phosphine salt into a 3L three-necked flask, add 1L to cool down to between 0 and -10°C, slowly add 0.3mol of potassium tert-butoxide in batches, and control the temperature to react between 0 and -10°C For 1 h, a THF solution of intermediate 11 (0.2 mol) was added dropwise, and the temperature was naturally raised to room temperature for 4 hours. After the reaction was completed, water was added, the aqueous phase was extracted with ethyl acetate, the combined organic phase was washed with saturated sodium chloride, dried, spin-dried, and recrystallized from ethanol to obtain compound 12, HPLC: 96%, yield Y=65%.

Intermediate 13

Add 0.06 mol of intermediate 12, 5.0 g of Pd/C, 0.3 L of THF and 0.2 L of EtOH into a 1 L three-neck flask, replace with N ₂ three times, H 2 three times, hydrodebenzyle at 40°C, and react for 6 hours. After the reaction was completed, filter with diatomaceous earth, concentrate the filtrate, beat PE:EA=10:1, and stir for 10 minutes to obtain compound 13, HPLC: 97%, yield Y=90%.

Compound I-4-1

Put 0.03mol of intermediate 13, 0.1mol of triethylamine, and 0.2L of DCM into a 500ml three-neck flask, and add 0.15mol of methacryloyl chloride dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 3 hours. After the reaction is complete, add water, extract the aqueous phase with DCM, combine the organic phases, wash once with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate the filtrate, dissolve 5 times of toluene at 45°C, pass through a 50 g silica gel column, and wash the column with 3 times of toluene. Concentrate, heat to dissolve 3 times toluene and 3 times alcohol, freeze at -20°C for 4 hours, filter with suction, recrystallize four times according to the same method, and dry to obtain white solid compound I-4-1, HPLC: 99.0%, yield Rate Y=70%.

Example 4

The structural formula of the compound is shown in the following formula I-6-1,

Its preparation route is as follows:

The specific operation process of preparation:

Intermediate 15

Under the protection of nitrogen, put 0.25mol of phosphine salt into a 3L three-necked flask, add 1L to cool down to between 0 and -10°C, slowly add 0.25mol of potassium tert-butoxide in batches, and control the temperature between 0 and -10°C to react For 1 h, a THF solution of intermediate 11 (0.15 mol) was added dropwise, and the temperature was naturally raised to room temperature for 4 hours. After the reaction is complete, add water, extract the aqueous phase with ethyl acetate, combine the organic phases, wash with saturated sodium chloride, dry, spin dry, separate by column chromatography (petroleum ether, ethyl acetate), and spin dry the solvent to obtain compound 15. HPLC : 95%, yield Y=80%.

Intermediate 16

Under the protection of nitrogen, add 0.15 mol of intermediate 15 and 0.15 mol of intermediate 3 into a 2L three-necked flask, then add 0.2 mol of triphenylphosphine, cool down to 0°C, add 0.2 mol of DIAD dropwise, and rise naturally after dropping Reaction at room temperature for 3h. The reaction is complete. Add water and ethyl acetate to separate the liquid, extract the aqueous phase with ethyl acetate, combine the organic phases to dry, spin dry, separate by column chromatography (petroleum ether, ethyl acetate), spin dry the solvent to obtain compound 16, HPLC: 95%, yield Y=70%.

Intermediate 17

Add 0.07 mol of intermediate 16, 6 g of Pd/C, 0.3 L of THF and 0.2 L of EtOH into a 1 L three-neck flask, replace with N ₂ three times, replace with H ₂ three times, hydrodebenzyle at 40°C, and react for 6 hours. After the reaction was completed, filter with diatomaceous earth, concentrate the filtrate, beat PE:EA=10:1, and stir for 10 minutes to obtain compound 17, HPLC: 98%, yield Y=80%.

Compound I-6-1

Put 0.04mol of intermediate 17, 0.15mol of triethylamine, and 0.2L of DCM into a 500ml three-neck flask, and add 0.2mol of methacryloyl chloride dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 3 hours. After the reaction is complete, add water, extract the aqueous phase with DCM, combine the organic phases, wash once with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate the filtrate, dissolve 5 times of toluene at 45°C, pass through a 50 g silica gel column, and wash the column with 3 times of toluene. Concentrate, heat to dissolve with 3 times of toluene and 3 times of alcohol, refrigerate at -20°C for 4 hours, filter with suction, recrystallize four times according to the same method, and dry to obtain white solid compound I-6-1, HPLC: 99.2%, yield Rate Y=45%.

Example 5

The structural formula of the compound is shown in the following formula I-7-1,

Its borrowing route nickel is as follows:

The specific operation process of preparation:

Intermediate 20

Under nitrogen protection, 0.4 mol of intermediate 1, 0.4 mol of intermediate 19, 2.0 L of toluene, 0.7 L of water, 0.6 mol of potassium carbonate, and 0.35 g of catalyst were put into a 5 L three-necked flask, and heated to reflux for 3 hours. The liquid was separated by standing, separated by column chromatography, and recrystallized from toluene/ethanol to obtain compound 20 as a pale yellow solid. HPLC: 96%, yield Y=85%.

Intermediate 21

Put 0.2mol of intermediate 20, 0.1mol of propylene glycol, 0.05mol of DMAP, 1.0L of THF in a 3L three-necked flask, and add 0.3mol of DCC THF solution dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 6 hours. After the reaction was completed, it was filtered, the filtrate was concentrated, and recrystallized from 3 times ethanol to obtain compound 21, GC: 94%, yield Y=78%.

Intermediate 22

Add 0.06 mol of compound 21, 6 g of Pd/C, 0.3 L of THF and 0.2 L of EtOH into a 1 L three-neck flask, replace with N ₂ three times, H 2 three times, hydrodebenzylation at 40°C, and react for 6 hours. After the reaction was completed, filter with diatomaceous earth, concentrate the filtrate, beat PE:EA=10:1, and stir for 10 minutes to obtain compound 22, HPLC: 98%, yield Y=86%.

Compound I-7-1

Put 0.02mol of intermediate 22, 0.1mol of triethylamine, and 0.2L of DCM into a 500ml three-neck flask, and add 0.1mol of methacryloyl chloride dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 3 hours. After the reaction is complete, add water, extract the aqueous phase with DCM, combine the organic phases, wash once with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate the filtrate, dissolve 5 times of toluene at 45°C, pass through a 50 g silica gel column, and wash the column with 3 times of toluene. Concentrate, heat to dissolve 3 times toluene and 3 times alcohol, freeze at -20°C for 4 hours, filter with suction, recrystallize four times according to the same method, and dry to obtain white solid compound I-7-1, HPLC: 99.0%, yield Rate Y=50%.

Example 6

The structural formula of the compound is shown in the following formula I-8-1,

Its preparation route is as follows:

The specific operation process of preparation:

The synthesis of intermediate 24 refers to intermediate 21 in Example 5, and the raw material propylene glycol is replaced by 1,6-hexanediol

The synthesis of intermediate 25 refers to intermediate 22 in Example 5

Compound I-8-1 is synthesized with reference to compound I-7-1 in Example 5

Example 7

The compound structural formula is shown in the following formula I-10-1:

Its preparation route is as follows:

The specific operation process of preparation:

Intermediate 27

Put 0.3mol of intermediate 3, 0.2mol of adipic acid, 0.06mol of DMAP, 1.0L of THF in a 3L three-necked flask, and add 0.4mol of DCC THF solution dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 6 hours. After the reaction was completed, it was filtered, the filtrate was concentrated, and recrystallized from 3 times ethanol to obtain compound 27, GC: 93%, yield Y=85%.

Intermediate 28

Add 0.05 mol of intermediate 27, 6.0 g of Pd/C, 0.3 L of THF and 0.2 L of EtOH into a 1 L three-neck flask, replace with N ₂ three times, replace with H ₂ three times, hydrodebenzyle at 40°C, and react for 6 hours. After the reaction was completed, filter with diatomaceous earth, concentrate the filtrate, beat PE:EA=10:1, and stir for 10 minutes to obtain compound 28, HPLC: 97%, yield Y=85%.

Compound I-10-1

Put 0.03mol of intermediate 28, 0.2mol of triethylamine, and 0.2L of DCM into a 500ml three-neck flask, and add 0.2mol of methacryloyl chloride dropwise at 0°C under the protection of _N2 . After dropping, react at room temperature for 3 hours. After the reaction is complete, add water, extract the aqueous phase with DCM, combine the organic phases, wash once with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate the filtrate, dissolve 5 times of toluene at 45°C, pass through a 50 g silica gel column, and wash the column with 3 times of toluene. Concentrate, heat to dissolve 3 times toluene and 3 times alcohol, freeze at -20°C for 4 hours, filter with suction, recrystallize four times according to the same method, and dry to obtain white solid compound I-10-1, HPLC: 99.1%, yield Rate Y=47%.

[Liquid Crystal Composition]

test parent 1

Test Matrix 2

Test Matrix 3

Test Matrix 4

Test Matrix 5

RM conversion evaluation

Determination of polymerization rate and residual amount of added polymerizable compounds in different liquid crystal matrices.

In the test matrix 1-5, add a certain amount of polymerizable compounds shown in formula I respectively; as a contrast, add an equal amount of RM-1, RM-2 to the test matrix 1-7 respectively, with the liquid crystal mentioned above Composition Preparation Method Prepare a liquid crystal composition, and perform HPLC analysis of the dissolved content of RM in the liquid crystal composition at this time. After the content is filled into the liquid crystal cell, simulate the PSA panel process 1 to measure its polymerization rate. The specific conditions: UV1: 64mw/cm ² @ 365nm, 100s; then cut open the liquid crystal cell for HPLC analysis, and compare the conversion results under UV1 as shown in the table below.

Specific conditions: UV2: 5mw/cm ² @ 365nm, 120min; then cut open the liquid crystal cell for HPLC analysis, the residual amount after UV2 is shown in the table below,

As can be seen from the above table, compared with the existing polymerizable compounds RM-1 and RM-2, the polymerizable compound represented by the formula I of the present invention, when verified with the same liquid crystal composition, shows that RM-1 , The polymerization rate of RM-2 is lower than the polymerizable compound of the present invention, because LCD manufacturer needs to expand production capacity, therefore faster polymerization rate is the high standard that different LCD manufacturers propose to the polymerization rate of polymer when liquid crystal is allocated, this paper The polymerizable compound formula I contained in the liquid crystal composition of the invention has a relatively fast polymerization rate, which can meet the manufacturer's requirements on the polymerization rate, and has a low residual amount, which is conducive to improving the display quality.

Apparently, the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, rather than limiting the implementation of the present invention. For those who are familiar with it, other different forms of changes or changes can also be made on the basis of the above description, and all implementation modes cannot be exhausted here, and any obvious changes or changes that are derived from the technical solutions of the present invention are still Within the protection scope of the present invention.

Claims (8)

A polymerizable compound, characterized in that it is selected from the group consisting of compounds represented by the following formula I-1-1 to formula I-17-3,

A liquid crystal composition, characterized in that it contains one or more polymerizable compounds described in Claim 1. According to the liquid crystal composition described in Claim 2, it is characterized in that it further comprises one or more compounds represented by the following formula II and one or more compounds represented by the following formula III,

In formula II, R ₁ and R ₂ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, Alkoxy group with 1-10 carbon atoms substituted by fluorine, alkenyl group with 2-10 carbon atoms, alkenyl group with 2-10 carbon atoms substituted by fluorine, and alkenyl group with 3-8 carbon atoms Alkenyloxy or fluorine-substituted alkenyloxy with 3-8 carbon atoms;

,

express independently

or

In formula III, R ₃ and R ₄ independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, and an alkoxy group with 1-10 carbon atoms , alkoxy group with 1-10 carbon atoms substituted by fluorine, alkenyl group with 2-10 carbon atoms, alkenyl group with 2-10 carbon atoms substituted with fluorine, 3-8 carbon atoms Alkenyloxy or alkenyloxy with 3-8 carbon atoms substituted by fluorine, and any one of R ₃ and R ₄ or a plurality of non-adjacent -CH ₂ - are optionally replaced by cyclopentylene, Substituted by cyclobutylene or cyclopropylene; Z ₁ and Z ₂ each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O- or -OCH ₂ -;

,

express independently

,

,

,

,

m ₁ means 1 or 2, when m ₁ means 2,

same or different; n ₁ means 0, 1 or 2, when n ₁ means 2,

same or different. According to the liquid crystal composition described in claim 3, it is characterized in that the compound represented by the formula II is selected from the group consisting of compounds represented by the formula II-1 to the formula II-17,

The compound shown in the formula III is selected from the group consisting of the compounds shown in the formula III-1 to the formula III-15,

Wherein, R ₃₁ and R ₄₁ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, a fluorine-substituted Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms An alkenyloxy group with 3-8 carbon atoms substituted by oxo or fluorine, and any one or a plurality of non-adjacent -CH ₂ -s are optionally replaced by cyclopentylene, cyclobutylene or cyclopropylene base substitution. The liquid crystal composition according to any one of claims 2-4, wherein the liquid crystal composition further comprises one or more compounds represented by formula IV,

Wherein, R ₅ and R ₆ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, a fluorine-substituted Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms An alkenyloxy group with 3-8 carbon atoms substituted by oxo or fluorine, and any one or a plurality of non-adjacent -CH ₂ -s are optionally replaced by cyclopentylene, cyclobutylene or cyclopropylene Substitution; W represents -O-, -S- or -CH ₂ O-. According to the liquid crystal composition described in Claim 5, it is characterized in that the liquid crystal composition further comprises one or more compounds represented by formula V,

Wherein, R ₇ and R ₈ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, or an alkyl group with 1-10 carbon atoms substituted by fluorine. Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms Alkenyloxy group with 3-8 carbon atoms substituted by oxy group or fluorine;

,

express independently

,

or

. According to the liquid crystal composition described in claim 6, it is characterized in that, the liquid crystal composition also includes one or more compounds shown in formula VI,

Wherein, R ₉ and R ₁₀ each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, or an alkyl group with 1-10 carbon atoms substituted by fluorine. Alkoxy groups with 1-10 carbon atoms, alkenyl groups with 2-10 carbon atoms, alkenyl groups with 2-10 carbon atoms substituted by fluorine, alkenyl groups with 3-8 carbon atoms Alkenyloxy group with 3-8 carbon atoms substituted by oxy group or fluorine;

express

,

or

; F ₁ , F ₂ , and F ₃ each independently represent an H atom or an F atom, and F ₂ and F ₃ are not F atoms at the same time. A liquid crystal display element, which comprises the compound described in Claim 1, or the liquid crystal composition described in any one of Claims 2-7, and the display element is an active matrix display element or a passive matrix display element.

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