TWI726179B - A compound and its liquid crystal composition and application - Google Patents

Abstract

The present invention discloses a compound comprising at least one cyclic structure and a bond of the group represented by the general formula I. The present invention also discloses a liquid crystal composition including the compound of the present invention, and an optoelectronic display device including the liquid crystal composition. The compound provided by the invention is stable in both chemical and physical properties, has good low-temperature storage properties, and at the same time has an appropriate size of dielectric anisotropy and refractive index anisotropy. When it is applied to liquid crystal products, the transmittance of the product can be significantly improved, and on this basis, the response speed is also significantly improved. In addition, the compound provided by the present invention has good compatibility with other liquid crystal compounds and has wide applicability.

Description

A compound and its liquid crystal composition and application

The invention belongs to the field of liquid crystal materials, and specifically relates to a compound and a liquid crystal composition and application thereof.

Liquid crystal display elements using the liquid crystal composition are widely used in displays of watches, calculators, word processors, and the like. These liquid crystal display elements utilize refractive index anisotropy, dielectric anisotropy, and the like of liquid crystal compounds. The known operating modes in liquid crystal display elements are mainly divided into PC (phase change, phase change), TN (twist nematic, twisted nematic), STN (super twisted nematic, super twisted nematic), ECB (electrically controlled birefringence, Electronically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment, vertical alignment) and other types. In recent years, research has also been actively conducted on the mode of applying an electric field to the optically isotropic liquid crystal phase to make it exhibit electro-induced birefringence.

The classification based on the driving mode of the element is mainly divided into a passive matrix (PM) and an active matrix (AM). Passive matrices are classified into static and multiplexed, and active matrices are classified into thin film transistors (TFT), metal-insulator-metal (metal insulator metal, MIM), and so on.

These liquid crystal display elements contain a liquid crystal composition having appropriate physical properties. The general physical properties necessary for the liquid crystal compound as a component of the liquid crystal composition are as follows.

(1) Chemical stability and physical stability; (2) High transparency point (phase transition temperature of liquid crystal phase-isotropic phase); (3) Liquid crystal phase (nematic phase, cholesterol phase, smectic phase, blue The lower limit temperature of the equal optically isotropic liquid crystal is low; (4) It has excellent compatibility with other liquid crystal compounds; (5) Has an appropriate size of dielectric anisotropy; (6) Has an appropriate size of refractive index anisotropy opposite sex.

The use of a liquid crystal composition containing a chemically and physically stable liquid crystal compound as described in (1) in a liquid crystal display element can improve the voltage holding ratio. In addition, if it is a liquid crystal composition containing a liquid crystal compound having a high clear point or a low minimum temperature of a liquid crystal phase as described in (2) and (3), the temperature range of the nematic phase or the optically isotropic liquid crystal phase can be expanded , Can be used as a display element in a wide temperature range. In order to exhibit characteristics that are difficult for a single compound to exhibit, the liquid crystal compound is generally used as a liquid crystal composition prepared by mixing with many other liquid crystal compounds. Therefore, the liquid crystal compound used in the liquid crystal display element preferably has good compatibility with other liquid crystal compounds and the like as described in (4). In recent years, liquid crystal display elements with higher display performance, such as contrast, display capacity, and response time characteristics, have been particularly demanded. Furthermore, a liquid crystal composition with a low driving voltage is required for the liquid crystal material used. In addition, in order to drive an optical element driven by an optically isotropic liquid crystal phase at a low voltage, it is preferable to use a liquid crystal compound having large dielectric anisotropy and refractive index anisotropy.

When displaying images on liquid crystal products, by applying different voltages, the rotation angle of the liquid crystal molecules can be controlled, and the light penetration can be changed to obtain different gray levels. For example, in a normally white liquid crystal panel, when no voltage is applied to the liquid crystal, the rod-shaped liquid crystal molecules will approximate In the lying position, the light passes through the upper and lower polarizers the most, and the liquid crystal panel presents a bright state; when a certain voltage is applied to the liquid crystal to make the liquid crystal stand vertically, the light can hardly pass through, and the liquid crystal panel appears dark. When it is necessary to display each intermediate gray scale, only the corresponding voltage needs to be applied to the liquid crystal.

In the above process of applying voltage to the liquid crystal, if the applied voltage is fixed, the characteristics of the liquid crystal molecules will be destroyed. Even if the voltage is canceled, the liquid crystal can no longer rotate with the change of the electric field, so that it cannot show a difference. Grayscale. Therefore, the display voltage of the liquid crystal panel will have positive and negative polarity, thereby changing the voltage applied to the liquid crystal. For example, when the display voltage of the liquid crystal panel is higher than the common electrode voltage, the display voltage is positive; conversely, when the display voltage of the liquid crystal panel is lower than the common electrode voltage, the display voltage is negative. Regardless of whether the display voltage is positive or negative, when the absolute value of the voltage difference between the display voltage and the common electrode voltage is the same, the gray scale presented is also the same.

It can be seen from the display process of the above-mentioned liquid crystal panel that the display gray scale is related to the light transmittance. Therefore, by measuring the transmittance curve of the liquid crystal panel, it is possible to set the voltage of the liquid crystal panel, thereby controlling the display of each gray scale, and obtaining an image pattern that conforms to the human senses.

Traditional liquid crystal displays often have problems such as low transmittance, high threshold voltage (~2.92V), and slow response time due to differences in driving methods and characteristics of liquid crystal molecules, which will cause driving difficulties and image smear. Therefore, there is an urgent need to provide a liquid crystal material with high transmittance and rapid response.

Objective of the invention: In view of the defects of the prior art, the objective of the present invention is to provide a compound with high transmittance and rapid response, a liquid crystal composition thereof, and a liquid crystal display element containing the liquid crystal composition.

其中，R表示碳原子數為1-12的烷基或鹵代烷基，其中所述烷基或鹵代烷基中的一個或多個-CH₂-可以以氧原子不直接相連的方式各自獨立地被-O-、-CH=CH-、-C≡C-、-CO-O-或-O-CO-替代；n表示1-12的整數。 Technical solution of the present invention: one aspect of the present invention provides a compound comprising at least one cyclic structure and a group represented by the general formula I,

Wherein, R represents an alkyl group or a halogenated alkyl group having 1-12 carbon atoms, wherein one or more of the alkyl group or the halogenated alkyl group -CH ₂ -may be each independently-in such a way that the oxygen atom is not directly connected. O-, -CH=CH-, -C≡C-, -CO-O- or -O-CO- are substituted; n represents an integer of 1-12.

Preferably, the at least one cyclic structure is connected to the group represented by the general formula I in the form of a "CO" single bond, wherein R represents a linear alkyl group having 1-12 carbon atoms or a halogenated group. A straight-chain alkyl group, wherein one or more non-adjacent -CH ₂ -in the straight-chain alkyl group or halogenated straight-chain alkyl group may be -O-, -CH= in such a way that the oxygen atom is not directly connected. CH-, -C≡C-, -CO-O- or -O-CO- substitution.

More preferably, the number of atoms in the ring skeleton of the cyclic structure is 3-12.

其中，A₁，A₂，A₃和A₄各自獨立地表示環骨架中原子個數為3-12的環狀結構，且所述環狀結構上的一個或多個H可被鹵素或烷基取代； R’表示H、鹵素、氰基、碳原子數為1-15的鹵代或未被鹵代的烷基，所述碳原子數為1-15的鹵代或未被鹵代的烷基中的一個或多個不相鄰的-CH₂-可以各自獨立地被-O-、-CH=CH-、-C≡C-、-CO-O-或-O-CO-替代；Z₁、Z₂和Z₃各自獨立地表示單鍵、-CH₂CH₂-、-CH₂O-、-OCH₂-、-CF=CF-、-CF₂O-、-OCF₂-、-COO-、-OCO-、-CH=CH-、-C≡C-、-CF₂CH₂-、-CH₂CF₂-、-(CH₂)₄-、-CF₂CF₂-、-OCH₂CH₂CH₂-、-CH₂OCH₂CH₂-、-CH₂CH₂OCH₂-、-CH₂CH₂CH₂O-、-OCH₂CH₂O-、-CH₂OCH₂O-或-OCH₂OCH₂-；a，b和c各自獨立地表示0、1、2、3或4。 Further preferably, the compound of the present invention has the structure of general formula II,

Wherein, A ₁ , A ₂ , A ₃ and A ₄ each independently represent a cyclic structure with 3-12 atoms in the ring skeleton, and one or more H on the cyclic structure may be halogenated or alkane Substitution; R'represents H, halogen, cyano, halogenated or unhalogenated alkyl with 1-15 carbon atoms, and halogenated or unhalogenated with 1-15 carbon atoms One or more non-adjacent -CH ₂ -in the alkyl group may be independently replaced by -O-, -CH=CH-, -C≡C-, -CO-O- or -O-CO-; Z ₁ , Z ₂ and Z ₃ each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CF ₂ O-, -OCF ₂ -, -COO-, -OCO-, -CH=CH-, -C≡C-, -CF ₂ CH ₂ -, -CH ₂ CF ₂ -, -(CH ₂ ) ₄ -, -CF ₂ CF ₂ -,- OCH ₂ CH ₂ CH ₂ -, -CH ₂ OCH ₂ CH ₂ -, -CH ₂ CH ₂ OCH ₂ -, -CH ₂ CH ₂ CH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ OCH ₂ O -Or -OCH ₂ OCH ₂ -; a, b and c each independently represent 0, 1, 2, 3 or 4.

More preferably, n represents an integer of 4-10.

Further preferably, said A ₁ , A ₂ , A ₃ and A ₄ are each independently selected from the group consisting of benzene ring, cyclohexane, naphthalene ring, indene ring, tetralin, decalin, oxane, and ring The group consisting of propane, cyclobutane, cyclopentane, cycloheptane, and bicyclo[2,2,2]octane; wherein, the above-mentioned cyclic structure can also meet at least one of the following conditions a and b: a, the One or more H in the cyclic structure may be substituted by halogen or alkyl; b. One or more -CH ₂ -in the cyclic structure may be -O-, -CO-, -CH=CH-, -C≡C-, -CO-O- or -O-CO- instead.

Further preferably, said A ₁ , A ₂ , A ₃ and A ₄ are each independently selected from the group consisting of benzene ring, cyclohexane, naphthalene ring, tetralin, and oxane, and the above cyclic structure At least one of the conditions a and b can also be met.

；以及

其中，R₁表示H、鹵素、氰基、碳原子數為1-15的鹵代或未被鹵代的烷基，所述碳原子數為1-15的鹵代或未被鹵代的烷基中的一個或多個不相鄰的-CH₂-可以各自獨立地被-O-、-CH=CH-、-C≡C-、-CO-O-或-O-CO-替代；環B₁、B₂、B₃和B₄各自獨立地表示

或

，且

中的一個或多個CH₂可被O替代，

中的一個或多個H可被F或CH₃取代；Z_a1、Z_a2和Z_a3各自獨立地表示單鍵、-CH₂CH₂-、-CH₂O-、-OCH₂-、-CF₂CF₂-、-CF₂O-、-OCF₂-、-COO-、-OCO-或-CH=CH-；通式Ⅱa和Ⅱb中，n表示2-10的整數；通式Ⅱc中，n表示4-10的整數。 Further preferably, the compound of the present invention is selected from the group consisting of the following compounds:

;as well as

Wherein, R ₁ represents H, halogen, cyano, halogenated or non-halogenated alkyl having 1-15 carbon atoms, and the halogenated or non-halogenated alkyl having 1-15 carbon atoms One or more non-adjacent -CH ₂ -in the group can be independently replaced by -O-, -CH=CH-, -C≡C-, -CO-O- or -O-CO-; ring B ₁ , B ₂ , B ₃ and B ₄ are each independently represented

or

And

One or more of CH ₂ can be replaced by O,

One or more of H may be replaced by F or CH ₃ ; _Za1 , _Za2 and _Za3 each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -CF ₂ CF ₂ -, -CF ₂ O-, -OCF ₂ -, -COO-, -OCO- or -CH=CH-; in general formula IIa and IIb, n represents an integer of 2-10; in general formula IIc, n represents an integer of 4-10.

，其中，L₁、L₂、L₃和L₄各自獨立的表示H、F或CH₃。 Further preferably, the ring B ₁ represents

, Where L ₁ , L ₂ , L ₃ and L ₄ each independently represent H, F or CH ₃ .

；以及

其中，環C₁、C₂和C₃各自獨立地表示

或

，且

中的一個或多個CH₂可被O替代，

中的一個或多個H可被F或CH₃取代；Z_b1、Z_b2和Z_b3各自獨立地表示單鍵、-CH₂CH₂-、-CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-；L₁和L₂各自獨立的表示H或F。 Further preferably, the compound of the present invention is selected from the group consisting of the following compounds:

;as well as

Among them, the rings C ₁ , C ₂ and C ₃ each independently represent

or

And

One or more of CH ₂ can be replaced by O,

One or more of H may be replaced by F or CH ₃ ; Z _b1 , Z _b2 and Z _b3 each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -; L ₁ and L ₂ each independently represent H or F.

；以及

所述通式Ⅱbb的化合物選自由如下化合物組成的組：

；以及

所述通式Ⅱcc的化合物選自由如下化合物組成的組：

；以及

Further preferably, the compound of the general formula IIaa is selected from the group consisting of the following compounds:

;as well as

The compound of the general formula IIbb is selected from the group consisting of the following compounds:

;as well as

The compound of the general formula IIcc is selected from the group consisting of the following compounds:

;as well as

More preferably, n is 4, 6, 8, or 10.

More preferably, the R ₁ and R each independently represent a halogenated or non-halogenated alkyl group or alkoxy group having 1 to 12 carbon atoms.

It should be noted that only simple chain length changes to the above compounds also belong to the protection scope of the compounds of the present invention.

Another aspect of the present invention also provides a liquid crystal composition comprising at least one of the above-mentioned compounds.

In another aspect of the present invention, there is also provided an optoelectronic display device comprising the above-mentioned liquid crystal composition.

Beneficial effects:

The compound provided by the invention is stable in both chemical and physical properties, has good low-temperature storage properties, and at the same time has an appropriate size of dielectric anisotropy and refractive index anisotropy. When it is applied to liquid crystal products, the transmittance of the product can be significantly improved, and on this basis, the response speed is also significantly improved. In addition, the compound provided by the present invention has good compatibility with other liquid crystal compounds and has wide applicability.

The present invention will be described below in conjunction with specific embodiments. It should be noted that the following embodiments are examples of the present invention, which are only used to illustrate the present invention, but not to limit the present invention. Without departing from the spirit or scope of the present invention, other combinations and various improvements within the concept of the present invention can be made.

For ease of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1: Table 1 The group structure code of the liquid crystal compound

Take the compound of the following structural formula as an example:

If the structural formula is expressed by the code listed in Table 1, it can be expressed as: nCCGF, where n in the code represents the number of C atoms of the left-end alkyl group, for example, n is "3", which means that the alkyl group is -C ₃ H ₇ ; C in the code represents cyclohexane, G represents 2-fluoro-1,4-phenylene, and F represents fluorine.

The abbreviated codes of the test projects in the following embodiments are as follows:

Cp(℃) Clearing point (nematic-isotropic phase transition temperature)

△n Refractive index anisotropy (589nm, 25℃)

△ε Dielectric anisotropy (1KHz, 25℃)

T(%) Transmittance (DMS-505, box thickness 5.2μm)

t(ms) Response time (DMS-505, 25±0.5℃)

Among them, the refractive index anisotropy is measured using an Abbe refractometer under a sodium lamp (589nm) light source at 25°C; △ε=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 conditions are: 25°C, 1KHz, the test box is TN90 type, and the box thickness is 7μm.

Test conditions for transmittance: use DMS 505 to test the transmittance of the dimming device, the box thickness of the dimming device is 5.2 μm.

Response time, the test conditions are: 25±0.5℃, the test box is 5.2μm IPS test box, and the test instrument is DMS-505.

In the following examples, the compound monomers and related reagents used are all commercially available.

Example 1

其具體製備過程如下：500ml三口瓶中，加入2.18g丙基環己基苯酚，100ml無水二甲基甲醯胺(DMF)，2.76g無水碳酸鉀，0.15g碘化鉀，1.4g 4-氯丁基甲醚，90℃攪拌6h，反應完畢後，後處理，經柱層析提純，得到2.5g白色固體，化合物No.2(R₁=-C₃H₇，R=-CH₃)，GC>99%，收率：91%。 Compound 1-(4-methoxy-butoxy)-4-(4-propyl-cyclohexyl)phenyl (No. 2(R ₁ =-C ₃ H ₇ , R=-CH ₃ ), note ：The number is shown in Table 2 below, the same below) The synthetic route is as follows:

The specific preparation process is as follows: In a 500ml three-necked flask, add 2.18g propylcyclohexylphenol, 100ml anhydrous dimethylformamide (DMF), 2.76g anhydrous potassium carbonate, 0.15g potassium iodide, 1.4g 4-chlorobutyl methyl ether, Stir at 90°C for 6 hours. After the reaction is complete, post-treatment and purification by column chromatography to obtain 2.5 g of white solid, compound No. 2 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ), GC>99%, Yield: 91%.

MS: 55 (11%) 87 (100%) 107 (8.9%) 120 (10%) 133 (7.8%).

Example 2

Compound 2,3-difluoro-4-(4-methoxy-butoxy)-4'-(4-propyl-cyclohexyl)-1,1'-biphenyl (No.66(R ₁ =-C ₃ H ₇ , R=-CH ₃ )) The synthetic route is as follows:

The specific preparation process is as follows:

1. Synthesis of compound M4

In a 500ml three-necked flask, add 5.1g 4-iodo-2,3-difluorophenol, 150ml anhydrous dimethylformamide (DMF), 5.5g anhydrous potassium carbonate, 0.3g potassium iodide, 2.8g 4-chlorobutyl methyl ether, Stir at 90°C for 6 hours, after the reaction is completed, post-treatment and purification by column chromatography to obtain 6.6 g of white solid, compound M4, GC>97%, yield: 97%.

2. Synthesis of compound No.66 (R ₁ =-C ₃ H ₇ , R=-CH ₃₎

Add 3.4g compound M4, 2.5g propylcyclohexylphenylboronic acid, 80ml toluene, 40ml ethanol, 40ml water, 4.2g anhydrous sodium carbonate, under nitrogen protection, add 0.1g tetrakis (triphenylphosphine) palladium in a 500ml three-necked flask , Heating and stirring at reflux for 6h, after the reaction is completed, post-treatment, column chromatography purification, to obtain 3.1g of white solid, compound No.66 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ), GC>99%, Yield: 75%.

MS: 55 (11%) 87 (100%) 219 (4.4%) 232 (5.6%) 245 (3.3%) 416 (1.7%).

Example 3

Compound 2',3'-difluoro-4-(4-methoxy-butoxy)-4"-propyl-1,1',4',1"-terphenyl (No.76(R ₁ =-C ₃ H ₇ , R=-CH ₃ )) The synthetic route is as follows:

The specific preparation process is as follows:

1. Synthesis of compound M7

In a 500ml three-necked flask, add 4.4g 4-iodophenol, 150ml anhydrous dimethylformamide (DMF), 5.5g anhydrous potassium carbonate, 0.3g potassium iodide, 2.8g 4-chlorobutyl methyl ether, stir at 90℃ for 6h, the reaction is complete Afterwards, post-treatment and purification by column chromatography to obtain 5.7 g of white solid, compound M7, GC>97%, yield: 93%.

2. Synthesis of compound No.76 (R ₁ =-C ₃ H ₇ , R=-CH ₃ )

In a 500ml three-necked flask, add 3.1g compound M7, 2.8g propyl difluorobiphenylboronic acid, 80ml toluene, 40ml ethanol, 40ml water, 4.2g anhydrous sodium carbonate, under nitrogen protection, add 0.1g tetrakis(triphenylphosphine) Palladium was heated and stirred at reflux for 6 hours. After the reaction was completed, post-treatment and purification by column chromatography yielded 3.4 g of white solid, compound No.76 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ), GC>99% , Yield: 83%.

MS: 55 (7.8%) 87 (100%) 302 (7.8%) 331 (23.4%) 359 (4.7%) 446 (3.1%).

Example 4

Compound 4'-[(hexyloxy)butoxy]-(1,1-biphenyl)-4-yl-4-methyl-[1,1-bis(cyclohexyl)]-4-carboxylic acid The synthetic route of (No.116(R ₁ =-CH ₃ , R=-C ₆ H ₁₃ )) is as follows:

The specific preparation process is as follows:

1. Synthesis of compound M11

Add 3.7g hydroquinone, 150ml anhydrous dimethylformamide (DMF), 5.5g anhydrous potassium carbonate, 0.3g potassium iodide, 3.8g 4-chlorobutylhexyl ether into a 500ml three-necked flask, stir at 90℃ for 6h, After the reaction is completed, post-treatment and purification by column chromatography to obtain 1.3 g of white solid, compound M11, GC>97%, yield: 19%.

2. Synthesis of compound No. 116 (R ₁ =-CH ₃ , R=-C ₆ H ₁₃ )

In a 250ml three-necked flask, add 1.3g compound M11, 0.85g methylbicyclohexylcarboxylic acid, 5mg 4-dimethylaminopyridine, 100ml dichloromethane, reduce the temperature to 0℃, drop 1.5g N,N'-dicyclohexyl carbon A solution composed of imidine (DCC) and 10ml of dichloromethane, after the dripping, stirred at room temperature for 12h, post-treatment, purified by column chromatography to obtain 1.7g of white solid, compound No.116 (R ₁ =-CH ₃ , R=-C ₆ H ₁₃ ), GC>99%, yield: 82%.

MS: 55 (11%) 87 (100%) 186 (31.6%) 307 (16.3%).

Example 5

With reference to the synthetic methods of the compounds in Examples 1 to 4, simply replacing the compounds M1 to M12 in the above reaction, the compounds No. 1 to No. 119 shown in Table 2 below can be prepared respectively.

For example: replace propyl cyclohexyl phenol M1 with ethyl phenol, and at the same time replace 4-chlorobutyl methyl ether M2 with 2-chloroethylhexyl ether, you can prepare compound No.6 (R ₁ =-C ₂ H ₅ , R=-C ₆ H ₁₃ ); Substituting propylcyclohexylphenol M1 with propyl phenol, compound No. 7 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ) can be prepared; Replace propylcyclohexylphenol M1 with ethoxybiphenol, and at the same time replace 4-chlorobutyl methyl ether M2 with 6-chlorohexyl methyl ether, to prepare compound No.8(R ₁ =-OC ₂ H ₅ , R=-CH ₃ ); Replace propylcyclohexylphenol M1 with butylcyclohexyldifluorophenol to prepare compound No. 12 (R ₁ =-C ₄ H ₉ , R=-CH ₃ ); Propylcyclohexylphenol M1 is replaced with hexyloxydifluorobiphenol, and compound No.17 (R ₁ =-OC ₆ H ₁₃ , R=-CH ₃ ) can be prepared; replace propylcyclohexylphenol M1 with Propylcyclohexylmethyleneoxydifluorophenol can be prepared to obtain compound No.27 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ); replace propylcyclohexylphenol M1 with ethyl bicyclic ring Hexyl phenol, and at the same time, replace 4-chlorobutyl methyl ether M2 with 2-chloroethyl ethyl ether to prepare compound No.36 (R ₁ =-C ₂ H ₅ , R=-C ₂ H ₅ ); Cyclohexylphenol M1 is replaced with pentylcyclohexylbiphenol, and 4-chlorobutyl methyl ether M2 is replaced with 3-chloropropyl ethyl ether at the same time, then compound No.43 (R ₁ =-C ₅ H ₁₁ , R= -C ₂ H ₅ ); Replace propylcyclohexylphenol M1 with methylbicyclohexylmethyleneoxydifluorophenol to prepare compound No.81 (R ₁ =-CH ₃ , R=-CH ₃ ) .

Application Comparative Example 1

According to the compounds and weight percentages listed in Table 3, the mixture M is prepared, which is filled between the two substrates of the liquid crystal display for performance testing. The test data is shown in Table 3 below:

Application Example 1

Compound No. 2 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ) was used to replace 3CPO2 in the mixture M, and the content of each component remained unchanged to obtain the mixture M1, which was filled between the two substrates of the liquid crystal display for performance The test data is shown in Table 4 below:

Application Example 2

Compound No. 12 (R ₁ =-C ₄ H ₉ , R=-CH ₃ ) was used to replace 3CWO4 in the mixture M, and the content of each component remained unchanged to obtain the mixture M2, which was filled between the two substrates of the liquid crystal display for performance The test data is shown in Table 5 below:

Application Example 3

Compound No. 66 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ) was used to replace 3CPWO2 in the mixture M, and the content of each component remained unchanged to obtain the mixture M3, which was filled between the two substrates of the liquid crystal display for performance The test data is shown in Table 6 below:

Application Example 4

Using the mixture M as the host liquid crystal (host), compound No. 7 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ), No. 8 (R ₁ =-OC ₂ H ₅ , R=-CH ₃ ), No.17 (R ₁ =-OC ₆ H ₁₃ , R=-CH ₃ ), No.76 (R ₁ =-C ₃ H ₇ , R=-CH ₃ ) and the host are 10% by weight: Mix at a ratio of 90% to obtain mixtures M4, M5, M6 and M7, which are respectively filled between the two substrates of the liquid crystal display for performance testing. The test data is shown in Table 7 below:

Comparing the foregoing application comparative example 1 with application examples 1 to 4, it can be seen that when the compound provided by the present invention is applied to a liquid crystal composition, the transmittance of the product can be significantly improved, and the response speed is also significantly improved on this basis. In addition, the compound provided by the present invention has good compatibility with other liquid crystal compounds and has wide applicability.

The above are only the preferred embodiments of the present invention and do not limit the present invention in any form. Although the present invention has been disclosed as the preferred embodiments, it is not intended to limit the present invention. Anyone familiar with the profession Technical personnel, without departing from the scope of the technical solution of the present invention Inside, when the technical content disclosed above can be used to make some changes or modifications into equivalent embodiments with equivalent changes, any simple modifications made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention, Equivalent changes and modifications still fall within the scope of the technical solution of the present invention.

Claims (6)

A compound characterized in that it contains at least one cyclic structure and a group represented by the general formula I,

Wherein, R represents an alkyl group or haloalkyl group having 1-12 carbon atoms, wherein one or more -CH ₂ -in the alkyl group or haloalkyl group may be independently replaced by -O in such a way that the oxygen atom is not directly connected. -, -CH=CH-, -C≡C-, -CO-O- or -O-CO- substitution; n represents an integer of 4-10; and the compound is selected from the group consisting of the following compounds:

;as well as

Wherein, R ₁ represents H, halogen, cyano, a halogenated or non-halogenated alkyl group with 1-15 carbon atoms, and the halogenated or non-halogenated alkyl group with 1-15 carbon atoms One or more non-adjacent -CH ₂ -in each can be independently replaced by -O-, -CH=CH-, -C≡C-, -CO-O- or -O-CO-; ring B ₁ , B ₂ , B ₃ and B ₄ are each independently represented

or

And

One or more of CH ₂ can be replaced by O,

One or more of H may be _{substituted by F or CH 3} ; Z _a1 , Z _a2 and Z _a3 each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -CF ₂ CF ₂ -, -CF ₂ O-, -OCF ₂ -, -COO-, -OCO- or -CH=CH-; wherein, the ring B ₁ represents

, Where L ₁ and L ₂ are F, and L ₃ and L ₄ are H. The compound described in item 1 of the scope of patent application, wherein it is selected from the group consisting of the following compounds:

;as well as

Among them, the rings C ₁ , C ₂ and C ₃ each independently represent

or

And

One or more of CH ₂ can be replaced by O,

One or more of H may be replaced by F or CH ₃ ; Z _b1 , Z _b2 and Z _b3 each independently represent a single bond, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -. The compound described in item 2 of the scope of patent application, wherein the compound of general formula IIaa is selected from the group consisting of the following compounds:

;as well as

The compound of the general formula IIbb is selected from the group consisting of the following compounds:

;as well as

The compound described in item 3 of the scope of patent application, wherein n is 4, 6, 8, or 10. A liquid crystal composition containing the compound described in any one of items 1 to 4 in the scope of the patent application. An optoelectronic display device comprising the liquid crystal composition described in item 5 of the scope of the patent application.