Liquid crystal compound, liquid crystal composition containing the same, and liquid crystal display device

Abstract

The present invention discloses a liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal display device. The liquid crystal compound is a compound represented by the following formula I, wherein X1 represents Se or Te; and X2 represents a fluorine atom, a perfluoroalkyl group having 1 to 5 carbon atoms, a perfluoroalkoxy group having 1 to 5 carbon atoms, a perfluoroalkenyl group having 2 to 5 carbon atoms, or a perfluoroalkenyloxy group having 2 to 5 carbon atoms. The liquid crystal composition containing the liquid crystal compound has a high ε ⊥ / Δε, high K ave , and excellent flicker levels, thus meeting the increasingly high transmittance, energy consumption, contrast, and refresh rate requirements of LCD devices. #imgabs0#Ⅰ.

Description

Technical Field

[0001] The present invention relates to the field of liquid crystal display, and more particularly to a liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal display device. Background Art

[0002] With the widespread application of TFT LCD (thin film transistor liquid crystal display technology), the requirements for its performance are also constantly increasing, especially for IPS and FFS liquid crystal display modes containing positive liquid crystals. Compared with VA liquid crystal display modes, although IPS and FFS liquid crystal display modes containing positive liquid crystals can significantly improve the viewing angle characteristics, their transmittance, energy consumption, contrast and refresh rate performance are still insufficient. High-quality display image quality requires it to have higher transmittance, lower energy consumption, higher contrast and higher refresh rate, which means that the liquid crystal material needs to have higher contrast and transmittance, higher elastic constant, higher ε ⊥ / Δε, and the improvement of these properties requires the improvement of liquid crystal materials.

[0003] With the upgrade of consumer electronics, 4K and 8K ultra-high-definition video content has become increasingly popular. Consumers have gradually increased their requirements for the light transmittance of LCD screens, requiring high transmittance (transmittance) to achieve a purer bright field to reproduce color. On the other hand, transmittance is directly related to backlight power consumption. High transmittance design solutions can reduce energy consumption of terminal LCD display products by more than 30%, which is in line with the global trend of green display development. Transmittance T and Δε / ε of positive LCD IPS mode and FFS mode ⊥ Inversely proportional, if you want to increase the transmittance of positive liquid crystal, you need to have a larger ε ⊥ / Δε ratio of liquid crystal materials.

[0004] In the competition between liquid crystal materials and OLED materials, although OLED materials have seized the high-end market with their theoretical infinite contrast, with the popularization of Mini LED technology in the field of liquid crystal display, terminal manufacturers have launched 4608-zone Mini LED backlight solutions, which can achieve a dynamic contrast ratio of millions, further narrowing the gap with OLED. However, liquid crystal materials with higher contrast are still needed to improve competitiveness. Compared with liquid crystal materials, the main factor affecting their contrast is dark state light scattering (light leakage). The less dark state light scattering (light leakage), the greater the contrast. To improve the light scattering of liquid crystal materials, it is necessary to increase the average elastic constant K ave To improve light scattering. ave Under such circumstances, the contrast of liquid crystal materials will be significantly improved.

[0005] The continued expansion of high-refresh-rate gaming and high-frame-rate video content (such as 120Hz / 240Hz sources) is driving demand for monitor refresh rates beyond 240Hz and toward 1000Hz, increasing the demand for monitor refresh rates. Furthermore, VR / AR devices in the virtual reality convergence space require low-latency displays and utilize dynamic refresh rate (VRR) technology to eliminate screen tearing, placing even higher demands on monitor refresh rates. The refresh rate of an LCD monitor is not only dependent on the hardware's drive voltage stability control and dimming technology, but also closely related to the flicker level (also known as flicker) of the liquid crystal material. The better the flicker level of the liquid crystal material, the higher the corresponding LCD monitor refresh rate.

[0006] In order to improve the ε of liquid crystal materials ⊥ / Δε performance, in recent years, liquid crystal monomers represented by fluorinated fused ring structures have become a hot topic of development. For example, the Chinese patent application with publication number CN106045953A discloses the following structure:

[0007]

[0008] Wherein, W represents O or S, Y represents F, Cl, CF3, OCF3 or OCF2H, and at least one of X1 and X2 represents F.

[0009] Such structures usually have a high vertical dielectric constant ε ⊥ , low viscosity, large refractive index, and its excellent monomer parameters make this type of monomer widely used in positive and negative high-penetration formulas used in FFS mode. However, the ε of the liquid crystal compound of the above structure is ⊥ / Δε、K ave The improvement in the performance and Flicker levels is limited. Summary of the Invention

[0010] Based on at least the above problems, the present invention aims to provide a liquid crystal compound, a liquid crystal composition comprising the same, and a liquid crystal display device. The liquid crystal compound has a high ratio of a vertical dielectric constant to a dielectric anisotropy ε ⊥ / Δε, high average elastic constant K ave , excellent Flicker level, the liquid crystal composition containing the liquid crystal compound has a high ε ⊥ / Δε, high K ave , and excellent Flicker level, so as to meet the increasingly higher transmittance, energy consumption, contrast and higher refresh rate requirements of LCD devices.

[0011] In order to achieve the above object, the present invention adopts the following technical solutions:

[0012] In one aspect, the present invention provides a liquid crystal compound, wherein the liquid crystal compound is a compound represented by the following formula I:

[0013] Ⅰ

[0014] in,

[0015] R1 represents H, an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkynyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, -CO-, -CO-O-, -O-CO-, 、 、 、 or In addition, one or more H atoms in these groups may be replaced by halogen;

[0016] Express the same or different meanings on each occurrence 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0017] Z1, in each occurrence, represents, identically or differently, a single bond, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, -CO-O-, or -O-CO-, and furthermore, one or more H atoms in these groups may be replaced by halogen;

[0018] X1 represents Se or Te;

[0019] X2 represents a fluorine atom, a perfluoroalkyl group having 1 to 5 carbon atoms, a perfluoroalkoxy group having 1 to 5 carbon atoms, a perfluoroalkenyl group having 2 to 5 carbon atoms, or a perfluoroalkenyloxy group having 2 to 5 carbon atoms;

[0020] m1 represents 0, 1, or 2;

[0021] When m1 represents 2, Same or different, Z1 same or different.

[0022] Furthermore, the compound represented by formula I is selected from at least one of the following compounds:

[0023] Ⅰa、 Ib

[0024] in,

[0025] R 11 represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, 、 、 、 or In addition, one or more H atoms in these groups may be replaced by halogen;

[0026] Z 11 represents a single bond, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-.

[0027] Furthermore, the compound represented by formula I is selected from at least one of the following compounds:

[0028] Ⅰa-1, Ⅰb-1,

[0029] Ⅰb-2, Ib-3,

[0030] Ⅰb-4, Ⅰb-5,

[0031] Ⅰb-6, Ib-7

[0032] in,

[0033] R 12 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, 、 、 、 or Alternatively, one or more H atoms in these groups may be replaced by halogen.

[0034] In a second aspect, the present invention provides a liquid crystal composition comprising one or more liquid crystal compounds as described in the first aspect above.

[0035] Furthermore, the liquid crystal composition comprises 0.1-30% of the compound represented by formula I in terms of mass percentage.

[0036] Furthermore, the liquid crystal composition further comprises at least one compound represented by Formula II:

[0037] Ⅱ

[0038] in,

[0039] and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0040] R2 and R3 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0041] Z2 represents -CH2-CH2-, -CF2-CF2-, -CF=CF-, -O-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond.

[0042] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula III:

[0043] III

[0044] in,

[0045] and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0046] R4 and R5 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms or an alkynyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0047] Z3 represents -CH2-CH2-, -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond;

[0048] m2 means 2, 3 or 4;

[0049] When m2 represents 2, 3 or 4, Same or different, Z3 same or different.

[0050] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula IV-1 and / or IV-2:

[0051] IV-1, IV-2

[0052] in,

[0053] 、 and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0054] express or ;

[0055] R6 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0056] X3 represents F, CF3, OCF3 or CN;

[0057] (F) each independently represents H or F;

[0058] m3 and m5 each independently represent 1 or 2;

[0059] m4 means 1, 2 or 3;

[0060] When m3 represents 2, Same or different;

[0061] When m4 represents 2 or 3, Same or different;

[0062] When m5 represents 2, Same or different.

[0063] Furthermore, the liquid crystal composition comprises, by weight percentage, 0.1-30% of the compound represented by formula I, 30-70% of the compound represented by formula II, 10-40% of the compound represented by formula III, and 5-35% of the compound represented by formula IV-1 and / or IV-2.

[0064] Furthermore, the liquid crystal composition contains at least one compound represented by formula V:

[0065] Ⅴ

[0066] in,

[0067] express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0068] R a 、R b Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0069] Z4 represents -CH2-CH2-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O-, -C≡C- or a single bond;

[0070] n1 represents 0, 1, or 2;

[0071] n2 represents 0 or 1;

[0072] When n1 represents 2, Same or different, Z4 same or different.

[0073] Furthermore, the liquid crystal composition further comprises at least one compound represented by formula VI:

[0074] VI

[0075] in,

[0076] R c 、Rd Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 、 、 or Replacement;

[0077] X4 represents -O-, -S-, -Se- or -CH2O-;

[0078] Z5 represents -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O- or a single bond;

[0079] express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0080] n3 represents 0, 1, or 2;

[0081] When n3 represents 2, Same or different, Z5 same or different.

[0082] In a third aspect, the present invention provides a liquid crystal display device, comprising the liquid crystal composition described in the second aspect above.

[0083] The beneficial effects of the present invention are as follows:

[0084] The liquid crystal compound provided by the present invention has a main ring molecular structure containing difluorodibenzoselenophene and difluorodibenzotellurophene structures, and a terminal group at one end of the main ring contains a specific polar group X2. The liquid crystal compound has a high ratio of vertical dielectric constant to dielectric anisotropy ε ⊥ / Δε, high average elastic constant K ave , excellent Flicker level; the liquid crystal composition of the present invention comprising the liquid crystal compound has a high ratio of vertical dielectric constant to dielectric anisotropy ε ⊥ / Δε, high average elastic constant K ave , excellent Flicker level, can be used to develop liquid crystal display devices with high transmittance, low energy consumption, high contrast and high refresh rate. BRIEF DESCRIPTION OF THE DRAWINGS

[0085] The specific embodiments of the present invention will be further described in detail below with reference to the accompanying drawings.

[0086] Figure 1 The mass spectrum of the compound represented by formula Ib-2-2 obtained in Synthesis Example 2 is shown. DETAILED DESCRIPTION

[0087] In order to more clearly illustrate the present invention, the present invention is further described below in conjunction with preferred embodiments and accompanying drawings. Similar components in the accompanying drawings are represented by the same reference numerals. It should be understood by those skilled in the art that the following detailed description is illustrative rather than restrictive and should not be used to limit the scope of protection of the present invention.

[0088] In order to obtain a liquid crystal display device with high transmittance, low energy consumption, high contrast and high refresh rate, a specific embodiment of the present invention provides a liquid crystal compound, a liquid crystal composition containing the same and a liquid crystal display device.

[0089] According to a specific embodiment of the present invention, a liquid crystal compound is provided. A liquid crystal composition comprising the liquid crystal compound has a high ε ⊥ / Δε, high K ave , and excellent flicker performance. Specifically, the liquid crystal compound is a compound represented by the following formula I:

[0090] Ⅰ

[0091] in,

[0092] R1 represents H, an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, or an alkynyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, -CO-, -CO-O-, -O-CO-, 、 、 、 or In addition, one or more H atoms in these groups may be replaced by halogen;

[0093] Express the same or different meanings on each occurrence 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0094] Z1, in each occurrence, represents, identically or differently, a single bond, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, -CO-O-, or -O-CO-, and furthermore, one or more H atoms in these groups may be replaced by halogen;

[0095] X1 represents Se or Te;

[0096] X2 represents a fluorine atom, a perfluoroalkyl group having 1 to 5 carbon atoms, a perfluoroalkoxy group having 1 to 5 carbon atoms, a perfluoroalkenyl group having 2 to 5 carbon atoms, or a perfluoroalkenyloxy group having 2 to 5 carbon atoms;

[0097] m1 represents 0, 1, or 2;

[0098] When m1 represents 2, Same or different, Z1 same or different.

[0099] In some examples, the halogen in this embodiment includes, but is not limited to, F, Cl, Br, and the like.

[0100] In some preferred examples, the compound represented by formula I is selected from at least one of the compounds shown below:

[0101] Ⅰa、 Ib

[0102] in,

[0103] R 11 represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, 、 、 、 or In addition, one or more H atoms in these groups may be replaced by halogen;

[0104] Z 11 represents a single bond, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-.

[0105] The liquid crystal composition containing the above liquid crystal compound has a relatively higher ε ⊥ / Δε、K ave , and better Flicker performance.

[0106] In some specific examples, the compound represented by Formula I is selected from at least one of the compounds shown below:

[0107] Ⅰa-1, Ⅰb-1,

[0108] Ⅰb-2, Ib-3,

[0109] Ⅰb-4, Ⅰb-5,

[0110] Ⅰb-6, Ib-7

[0111] in,

[0112] R 12 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, 、 、 、 or Alternatively, one or more H atoms in these groups may be replaced by halogen.

[0113] In some more specific examples, the compound represented by Formula I is selected from at least one of the compounds shown below:

[0114] Ⅰa-1-1、 Ⅰa-1-2,

[0115] Ⅰa-1-3, Ⅰa-1-4,

[0116] Ⅰa-1-5, Ⅰa-1-6,

[0117] Ⅰa-1-7, Ⅰa-1-8,

[0118] Ⅰa-1-9, Ⅰa-1-10,

[0119] Ⅰa-1-11, Ⅰa-1-12,

[0120] Ⅰa-1-13、 Ⅰa-1-14、

[0121] Ⅰa-1-15、 Ⅰa-1-16、

[0122] Ⅰa-1-17、 Ⅰa-1-18、

[0123] Ⅰa-1-19、 Ⅰa-1-20、

[0124] Ⅰb-1-1、 Ⅰb-1-2、

[0125] Ⅰb-1-3、 Ⅰb-1-4、

[0126] Ⅰb-1-5、 Ⅰb-1-6、

[0127] Ⅰb-1-7、 Ⅰb-1-8、

[0128] Ⅰb-1-9、 Ⅰb-1-10、

[0129] Ⅰb-1-11、 Ⅰb-1-12、

[0130] Ⅰb-2-1、 Ⅰb-2-2、

[0131] Ⅰb-2-3、 Ⅰb-2-4、

[0132] Ⅰb-2-5、 Ⅰb-2-6、

[0133] Ⅰb-2-7、 Ⅰb-2-8、

[0134] Ⅰb-2-9、

[0135] Ⅰb-2-10、 Ⅰb-2-11、

[0136] Ⅰb-2-12、 Ⅰb-2-13、

[0137] Ⅰb-2-14、 Ⅰb-2-15、

[0138] Ⅰb-2-16、 Ⅰb-2-17、

[0139] Ⅰb-2-18、

[0140] Ⅰb-3-1、 Ⅰb-3-2、

[0141] Ⅰb-3-3、 Ⅰb-3-4、

[0142] Ⅰb-4-1、 Ⅰb-4-2、

[0143] Ⅰb-4-3、 Ⅰb-4-4、

[0144] Ⅰb-4-5、 Ⅰb-4-6、

[0145] Ⅰb-4-7、 Ⅰb-4-8、

[0146] Ⅰb-5-1、 Ⅰb-5-2、

[0147] Ⅰb-5-3、 Ⅰb-5-4、

[0148] Ⅰb-6-1、 Ⅰb-6-2、

[0149] Ⅰb-6-3、 Ⅰb-6-4、

[0150] Ⅰb-7-1、 Ⅰb-7-2、

[0151] Ⅰb-7-3, Ⅰb-7-4.

[0152] According to another specific embodiment of the present invention, a liquid crystal composition is provided, wherein the liquid crystal composition comprises one or more liquid crystal compounds as provided in the first specific embodiment above.

[0153] In some examples, the liquid crystal composition comprises 0.1-30% of the compound represented by Formula I, calculated by weight percentage. The liquid crystal composition obtained under this condition has a relatively higher ε ⊥ / Δε、K ave , and better Flicker performance.

[0154] In some specific examples, the content of the compound represented by Formula I in the liquid crystal composition includes but is not limited to 0.1-30%, 5-20%, 5-15%, 5-10%, 10-15%, 5%, 6%, 7%, 8%, 13.5%, etc., calculated by weight percentage.

[0155] In some examples, the liquid crystal composition further comprises at least one compound represented by Formula II:

[0156] Ⅱ

[0157] in,

[0158] and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0159] R2 and R3 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0160] Z2 represents -CH2-CH2-, -CF2-CF2-, -CF=CF-, -O-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond.

[0161] In some specific examples, the compound represented by Formula II is selected from at least one of the following compounds:

[0162] Ⅱ-1、 Ⅱ-2、

[0163] Ⅱ-3、 Ⅱ-4,

[0164] Ⅱ-5, Ⅱ-6,

[0165] Ⅱ-7.

[0166] In some specific examples, the content of the compound represented by Formula II in the liquid crystal composition includes but is not limited to 30-70%, 30-65%, 30-60%, 35-60%, 35-55%, 35-50%, 40-60%, 40-55%, etc., calculated by weight percentage.

[0167] In some examples, the liquid crystal composition further comprises at least one compound represented by Formula III:

[0168] III

[0169] in,

[0170] and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0171] R4 and R5 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms or an alkynyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0172] Z3 represents -CH2-CH2-, -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond;

[0173] m2 means 2, 3 or 4;

[0174] When m2 represents 2, 3 or 4, Same or different, Z3 same or different.

[0175] In some specific examples, the compound represented by Formula III is selected from at least one of the following compounds:

[0176] Ⅲ-1、 Ⅲ-2、

[0177] Ⅲ-3、 III-4,

[0178] Ⅲ-5、 Ⅲ-6、

[0179] Ⅲ-7,

[0180] Ⅲ-8

[0181] Ⅲ-9,

[0182] Ⅲ-10,

[0183] Ⅲ-11、

[0184] Ⅲ-12,

[0185] Ⅲ-13,

[0186] Ⅲ-14,

[0187] Ⅲ-15,

[0188] Ⅲ-16.

[0189] In some specific examples, the content of the compound represented by Formula III in the liquid crystal composition includes but is not limited to 10-40%, 10-35%, 12-40%, 12-35%, 12-30%, 12-25%, 25-35%, etc., calculated by weight percentage.

[0190] In some examples, the liquid crystal composition further comprises at least one compound represented by Formula IV-1 and / or IV-2:

[0191] IV-1, IV-2

[0192] in,

[0193] 、 and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0194] express or ;

[0195] R6 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0196] X3 represents F, CF3, OCF3 or CN;

[0197] (F) each independently represents H or F;

[0198] m3 and m5 each independently represent 1 or 2;

[0199] m4 means 1, 2 or 3;

[0200] When m3 represents 2, Same or different;

[0201] When m4 represents 2 or 3, Same or different;

[0202] When m5 represents 2, Same or different.

[0203] In some preferred examples, the compound represented by Formula IV-1 and / or Formula IV-2 is selected from at least one of the compounds shown below:

[0204] IV-1-1 IV-1-2

[0205] IV-1-3 IV-1-4

[0206] IV-1-5

[0207] IV-1-6

[0208] IV-1-7

[0209] IV-1-8

[0210] IV-1-9

[0211] IV-2-1

[0212] IV-2-2,

[0213] IV-2-3

[0214] IV-2-4

[0215] IV-2-5 IV-2-6

[0216] IV-2-7

[0217] IV-2-8

[0218] IV-2-9.

[0219] In some specific examples, the content of the compound represented by Formula IV-1 and / or IV-2 in the liquid crystal composition includes but is not limited to 5-35%, 10-35%, 10-30%, 10-25%, 10-20%, 15-35%, 15-30%, 15-25%, 15-20%, etc., calculated by mass percentage.

[0220] In some preferred examples, the liquid crystal composition contains, by weight percentage, 0.1-30% of the compound represented by formula I, 30-70% of the compound represented by formula II, 10-40% of the compound represented by formula III, and 5-35% of the compound represented by formula IV-1 and / or IV-2.

[0221] In some examples, the liquid crystal composition comprises at least one compound represented by Formula V:

[0222] Ⅴ

[0223] in,

[0224] express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F;

[0225] R a 、R b Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement;

[0226] Z4 represents -CH2-CH2-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O-, -C≡C- or a single bond;

[0227] n1 represents 0, 1, or 2;

[0228] n2 represents 0 or 1;

[0229] When n1 represents 2, Same or different, Z4 same or different.

[0230] In some preferred examples, the compound represented by formula V is selected from at least one of the following compounds:

[0231] Ⅴ-1、 Ⅴ-2,

[0232] Ⅴ-3, Ⅴ-4,

[0233] Ⅴ-5, Ⅴ-6,

[0234] Ⅴ-7, Ⅴ-8,

[0235] Ⅴ-9, Ⅴ-10,

[0236] Ⅴ-11, Ⅴ-12,

[0237] Ⅴ-13, Ⅴ-14,

[0238] Ⅴ-15, Ⅴ-16,

[0239] Ⅴ-17, Ⅴ-18,

[0240] Ⅴ-19, Ⅴ-20,

[0241] Ⅴ-21, Ⅴ-22.

[0242] In some specific examples, the content of the compound represented by Formula V in the liquid crystal composition includes but is not limited to 0, 0-20%, 0-15%, 0-10%, 1-20%, 1-15%, 1-10%, 5-20%, 5-15%, 5-10%, etc., calculated by weight percentage.

[0243] In some examples, the liquid crystal composition further comprises at least one compound represented by Formula VI:

[0244] VI

[0245] in,

[0246] R c 、R d Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 、 、 or Replacement;

[0247] X4 represents -O-, -S-, -Se- or -CH2O-;

[0248] Z5 represents -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O- or a single bond;

[0249] express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F;

[0250] n3 represents 0, 1, or 2;

[0251] When n3 represents 2, Same or different, Z5 same or different.

[0252] In some preferred examples, the compound represented by formula VI is selected from at least one of the following compounds:

[0253] VI-1, VI-2,

[0254] VI-3, VI-4,

[0255] VI-5, VI-6,

[0256] VI-7, VI-8,

[0257] VI-9, VI-10,

[0258] VI-11, VI-12,

[0259] VI-13, Ⅵ-14.

[0260] In some specific examples, the content of the compound represented by Formula VI in the liquid crystal composition includes, but is not limited to, 0, 0-5%, 1-5%, etc., calculated by weight percentage.

[0261] In some examples, the alkyl group is a linear or branched alkyl group, and / or the alkenyl group is a linear or branched alkenyl group, and / or the alkynyl group is a linear or branched alkynyl group.

[0262] Various functional additives may be added to the liquid crystal compound provided in this embodiment, and the weight percentage of exemplary additives is preferably between 0.01-1%. These additives mainly include chiral agents, antioxidants, light stabilizers, polymerizable monomers, self-aligning agents, etc.

[0263] Exemplary antioxidant and light stabilizer additives are selected from the following compounds:

[0264]

[0265]

[0266] According to another embodiment of the present invention, a liquid crystal display device is provided. The liquid crystal display device includes the liquid crystal composition as described above.

[0267] In some examples, the liquid crystal display device is an IPS, FFS, or VA mode display.

[0268] In the present application, the elements contained in the compound include all their corresponding isotopes, for example, compounds in which H, C, N, O, Cl, F, Se and Te have been replaced by corresponding isotopes, and this is also particularly preferred in some embodiments.

[0269] The technical solution of the present invention is described below with reference to some specific embodiments:

[0270] In this manual, unless otherwise specified, percentages refer to mass percentages, temperatures are in degrees Celsius (°C), and the specific meanings of other symbols and test conditions are as follows:

[0271] Cp represents the clearing point of liquid crystal (°C), measured by DSC quantitative method;

[0272] Δn represents optical anisotropy, no is the refractive index of ordinary light, and ne is the refractive index of extraordinary light. The test conditions are 25±2℃, 589nm, and Abbe refractometer.

[0273] Δε represents dielectric anisotropy, Δε=ε ∥ -ε ⊥ , where ε ∥ is the dielectric constant parallel to the molecular axis (parallel dielectric constant), ε ⊥ is the dielectric constant perpendicular to the molecular axis (perpendicular dielectric constant), tested at 25±0.5°C, 20 μm vertical cell, INSTEC: ALCT-IR1 test;

[0274] K 11 is the splay elastic constant, K 22 is the torsional elastic constant, K 33 is the bending elastic constant, the test conditions are: 25°C, INSTEC:ALCT-IR1, 20 μm vertical cell;

[0275] Average elastic constant K ave =(K 11 +K 22 +K 33 )÷3;

[0276] γ1 represents the rotational viscosity (mPa·s), the test conditions are 25±0.5℃, 20 μm vertical cell, INSTEC: ALCT-IR1 test;

[0277] Flicker flexure test method: The flicker data of the test sample is measured at a voltage of V100 (the voltage required to apply to the test box containing liquid crystal when its transmittance is 100%). The test conditions are 25±0.5℃, FFS test box, and DMS-501 test equipment. The unit is expressed in dB. The flicker test data is a negative value. The smaller the value (the larger the absolute value), the better the flicker level. At high refresh rates, the flicker is smaller.

[0278] The preparation method of the liquid crystal composition is as follows: the liquid crystal monomers are weighed according to a certain ratio and placed in a stainless steel beaker. The stainless steel beaker containing the liquid crystal monomers is placed on a magnetic stirring apparatus to heat and melt. After the liquid crystal monomers in the stainless steel beaker are mostly melted, a magnetic rotor is added to the stainless steel beaker, and the mixture is stirred evenly. After cooling to room temperature, the liquid crystal composition is obtained.

[0279] The synthesis of the compounds of formula I according to the present invention is described by way of example in the Examples. The starting materials can be obtained by commonly available literature procedures or are commercially available. The following explains a particularly suitable synthetic route for the compounds of formula I according to the present invention:

[0280] When X1 is selenium, it can be synthesized according to the following scheme 1:

[0281] Option 1:

[0282]

[0283] When X1 is a tellurium element, it can be synthesized according to the following scheme 2:

[0284] Option 2:

[0285]

[0286] Among them, R1, , Z1, X2 and m1 etc. have the meanings indicated for the compound shown in Formula I.

[0287] Scheme 1 and Scheme 2 should be considered as illustrative only. A person skilled in the art will be able to implement corresponding variations of the syntheses presented and also follow other suitable synthetic routes to obtain compounds of formula I.

[0288] Examples of compounds represented by formula I

[0289] The present invention is described below using the following specific examples.

[0290] Synthesis example 1

[0291] Preparation of Liquid Crystalline Compound Ⅰa-1-2

[0292] Compound 1:

[0293]

[0294] 20 g of 2,3-difluoro-4-ethoxyphenylboronic acid, 28 g of 2-fluoro-4-bromo-1-trifluoromethoxybenzene, and 15 g of potassium carbonate were added to a three-necked flask containing a solvent (toluene:water = 150 mL:50 mL). After nitrogen displacement, 0.05 g of palladium 132 was added. The temperature was raised to reflux for reaction for 1 h. The layers were separated, and the toluene phase was passed through a column and concentrated to obtain 31 g of a yellow solid, GC:97.5%, with a yield of 91%.

[0295] Compound 2:

[0296]

[0297] 31 g of compound 1 was dissolved in 200 mL of tetrahydrofuran and added to a three-necked flask. After nitrogen was replaced, the temperature was lowered to -78 ° C. 92 mL of a 1 mol / L lithium diisopropylamide solution was added dropwise at a controlled temperature. The reaction was kept warm for 1 h. 138 mL of a 1 mol / L tetrahydrofuran solution of dibenzyl diselenide was added dropwise at a controlled temperature of -78 ° C. The temperature was naturally raised to react for 2 h. After the reaction was quenched by adding water, the pH was adjusted to 4-5. The mixture was extracted with ethyl acetate, dried, and concentrated to obtain 33 g of an orange solid with a GC value of 96.8% and a yield of 70%.

[0298] Compound 3:

[0299]

[0300] 33 g of compound 2 was dissolved in tetrahydrofuran, and 3 g of palladium hydroxide was added. After replacing hydrogen, the mixture was reacted at room temperature for 12 h and then subjected to hydrogenation and debenzylation. After completion of the reaction, the palladium hydroxide was filtered off through diatomaceous earth and concentrated to obtain 25.2 g of a light yellow solid, GC: 95.0%, and a yield of 94%.

[0301] Compound Ⅰa-1-2:

[0302]

[0303] 25.2 g of compound 3 was dissolved in 200 mL of dimethyl sulfoxide and added to a three-necked flask. 10.2 g of potassium tert-butoxide was added and the temperature was raised to 120 °C for reaction for 8 h. After the reaction was completed, the reaction solution was poured into 600 mL of ice water for slurrying. A light yellow solid was obtained by filtration and purified by recrystallization from toluene and ethanol to obtain 15.4 g of a white solid, GC: 99.7%, and a yield of 62%.

[0304] The starting material 2,3-difluoro-4-ethoxyphenylboronic acid was replaced with commercially available 2,3-difluoro-4-butylbiphenylboronic acid, and the following compound was prepared according to the above synthetic route:

[0305] Ⅰb-3-1.

[0306] The starting material 2,3-difluoro-4-ethoxyphenylboronic acid was replaced with commercially available 2,3-difluoro-4-ethylcyclohexylphenylboronic acid, and the following compound was prepared according to the above synthetic route:

[0307] Ⅰb-1-1.

[0308] Synthesis example 2

[0309] Preparation of Liquid Crystal Compound Ⅰb-2-2

[0310] Compound 4:

[0311]

[0312] 23 g of 2,3-difluoro-4-chlorobromobenzene was dissolved in 200 mL of tetrahydrofuran and added to a three-necked flask. After nitrogen was replaced, the temperature was lowered to -78°C. 42 mL of 2.5 mol / L butyl lithium was added dropwise at a controlled temperature. After the addition, the temperature was controlled at -78°C for 1 h. 96 mL of a 1 mol / L solution of 4-propylcyclohexanone in tetrahydrofuran was added dropwise while maintaining the temperature. After the addition, the temperature was naturally raised for 2 h. After quenching with water, the pH was adjusted to 4-5. The product was extracted with ethyl acetate, dried, and concentrated to obtain 22 g of a yellow oily product with a GC value of 95.2% and a yield of 86%.

[0313] Compound 5:

[0314]

[0315] 22 g of compound 4, 18 g of 3-fluoro-4-trifluoromethoxyphenylboronic acid, and 12 g of potassium carbonate were added to a three-necked flask containing a solvent (a mixture of 150 mL of toluene and 50 mL of water). Under a nitrogen atmosphere, 0.08 g of SPhos Pd G2 was added, and the temperature was raised to reflux for 8 h. The mixture was separated and filtered through a column to obtain 24 g of a yellow solid, GC: 96.8%, for a yield of 70%.

[0316] Compound 6:

[0317]

[0318] 24g of compound 5 was dissolved in 200mL of tetrahydrofuran and added to a three-necked flask. After nitrogen displacement, the temperature was lowered to -78°C. 87mL of 1mol / L lithium diisopropylamide was added dropwise at this temperature. The reaction was incubated for 1h. 87mL of a 1mol / L solution of dibenzyl diselenide in tetrahydrofuran was added dropwise at -78°C. The reaction was allowed to warm naturally for 2h. The reaction was quenched with water, the pH was adjusted to 4-5, and the mixture was extracted with ethyl acetate, dried, and concentrated to yield 21.2g of an orange solid (GC: 95.3%), with a yield of 62%.

[0319] Compound 7:

[0320]

[0321] 21.2 g of compound 6 was dissolved in 400 mL of dichloromethane and stirred at 0°C until completely dissolved. 10.9 g of boron tribromide was dissolved in 50 mL of dichloromethane and added dropwise to the above solution. The reaction was kept warm for 1 h. 200 mL of water was added to quench the reaction. The product was extracted twice with 200 mL of dichloromethane and dried. After concentration, it was purified by column chromatography to obtain 16.4 g of a solid, GC: 98.2%, and a yield of 92%.

[0322] Compound Ib-2-2:

[0323]

[0324] 16.4 g of compound 6 was dissolved in 200 mL of dimethyl sulfoxide and added to a three-necked flask. 5.4 g of potassium tert-butoxide was added and the temperature was raised to 120 ° C for reaction for 8 h. After the reaction was completed, the reaction solution was poured into 600 mL of ice water for slurrying. A light yellow solid was obtained by filtration and purified by recrystallization from toluene and ethanol to obtain 9.3 g of a white solid, GC: 99.8%, and a yield of 59%.

[0325] The mass spectrum of the compound represented by formula Ⅰb-2-2 is as follows Figure 1 shown.

[0326] The starting material 3-fluoro-4-trifluoromethoxyphenylboronic acid was replaced with commercially available 3-fluoro-4-trifluoromethylphenylboronic acid, and the following compound was prepared according to the above synthetic route:

[0327] Ib-2-6.

[0328] The starting material 3-fluoro-4-trifluoromethoxyphenylboronic acid was replaced with commercially available 3,4-difluorophenylboronic acid, and the following compound was prepared according to the above synthetic route:

[0329] Ib-2-7.

[0330] Synthesis example 3

[0331] Preparation of Liquid Crystal Compound Ⅰb-4-1

[0332] Compound 8:

[0333]

[0334] 21 g of 2,3-difluoro-4-bromophenol, 16 g of ethylcyclohexylmethanol, and 30 g of triphenylphosphine were added to a three-necked flask with 200 mL of tetrahydrofuran as solvent. The mixture was cooled to 0°C under a nitrogen atmosphere, and 24 g of diisopropyl azodicarboxylate was added dropwise under temperature-controlled conditions. The mixture was then reacted at room temperature for 8 h. The reaction was quenched with water, extracted with EA, dried, concentrated, and subjected to column chromatography to obtain 26 g of a colorless oily product with a GC ratio of 96.0% and a yield of 78%.

[0335] Compound 9:

[0336]

[0337] 26 g of compound 8, 18 g of 3-fluoro-4-trifluoromethoxyphenylboronic acid, and 11 g of potassium carbonate were added to a three-necked flask containing 150 mL of toluene and 50 mL of water. After nitrogen displacement, 0.05 g of palladium 132 was added, and the temperature was raised to reflux for 1 h. The layers were separated, and the toluene phase was passed through a column and concentrated to obtain 32 g of a yellow solid, GC: 95.6%, with a yield of 95%.

[0338] Compound 10:

[0339]

[0340] 32 g of compound 9 was dissolved in 200 mL of tetrahydrofuran and added to a three-necked flask. After nitrogen was replaced, the temperature was lowered to -78°C, and 117 mL of 1 mol / L lithium diisopropylamide was added dropwise at a temperature-controlled manner. The reaction was kept warm for 1 h. 111 mL of a 1 mol / L tetrahydrofuran solution of dibenzyl diselenide was added dropwise at a temperature-controlled manner at -78°C. The temperature was naturally raised to react for 2 h. After the reaction was quenched by adding water, the pH was adjusted to 4-5. The mixture was extracted with ethyl acetate, dried, and concentrated to obtain 34.7 g of an orange solid with a GC value of 97.5% and a yield of 78%.

[0341] Compound 11:

[0342]

[0343] 34.7 g of compound 10 was dissolved in 300 mL of tetrahydrofuran, and 3.4 g of palladium hydroxide was added. After replacing hydrogen, the mixture was reacted at room temperature for 12 h and then hydrodebenzylated. After completion of the reaction, the palladium hydroxide was filtered off through diatomaceous earth and concentrated to obtain 28.2 g of a light yellow solid, GC: 98.4%, and a yield of 95%.

[0344] Compound Ib-4-1:

[0345]

[0346] 28.2 g of compound 11 was dissolved in 200 mL of dimethyl sulfoxide and added to a three-necked flask. 6.5 g of potassium tert-butoxide was added and the temperature was raised to 120 °C for reaction for 8 h. After the reaction was completed, the reaction solution was poured into 600 mL of ice water for slurrying. A light yellow solid was obtained by filtration and purified by recrystallization from toluene and ethanol to obtain 19.7 g of a white solid, GC: 99.5%, and a yield of 73%.

[0347] Synthesis example 4

[0348] Preparation of Liquid Crystalline Compound Ⅰb-5-1

[0349] Compound 12:

[0350]

[0351] 15 g of ethylcyclohexanone, 16 g of p-toluenesulfonylhydrazide and 150 mL of methanol were added to a single-necked bottle. After stirring for one hour, the reaction solution was filtered to obtain 32 g of a white solid, GC: 99.0%, and a yield of 92%.

[0352] Compound 13:

[0353]

[0354] 32g of compound 12 was dissolved in 160mL of tetramethylethylenediamine in a three-necked flask. The mixture was cooled to -50°C under nitrogen and 87mL of 2.5mol / L butyllithium was added dropwise. The mixture was allowed to react at room temperature for 1.5h. The temperature was then lowered to below 0°C and 17mL of N,N-dimethylformamide was added dropwise. The reaction was continued at room temperature for 1.5h. The reaction was quenched with water, extracted twice with EA, dried, and concentrated to yield 13g of a yellow oily liquid (GC: 96.9%, yield: 85%).

[0355] Compound 14:

[0356]

[0357] 13 g of compound 14 was dissolved in 200 mL of THF, and 6 g of potassium borohydride and 40 mL of water were added. The mixture was reacted at room temperature for 1 h. After acid adjustment, the mixture was extracted with EA and filtered through a column to obtain 12.5 g of a light yellow solid. GC analysis showed that the solid had a 97.2% yield and a yield of 96%.

[0358] Compound 15:

[0359]

[0360] 19 g of 2,3-difluoro-4-bromophenol, 12.5 g of compound 14, and 27 g of triphenylphosphine were added to a three-necked flask containing 200 mL of tetrahydrofuran. The mixture was cooled to 0°C under a nitrogen atmosphere. 22 g of diisopropyl azodicarboxylate was added dropwise under temperature-controlled conditions, and the mixture was allowed to react at room temperature for 8 h. The reaction was quenched with water, extracted with EA, dried, concentrated, and purified by column chromatography to afford 24 g of the product as a colorless oil (GC: 95.8%), with a yield of 82%.

[0361] Compound 16:

[0362]

[0363] 24 g of compound 15, 16.2 g of 3-fluoro-4-trifluoromethoxyphenylboronic acid, and 9.5 g of potassium carbonate were added to a three-necked flask containing a solvent (toluene:water = 120 mL:40 mL). After nitrogen displacement, 0.05 g of palladium 132 was added. The temperature was raised to reflux for reaction for 1 h. The layers were separated, and the toluene phase was passed through a column and concentrated to obtain 30 g of a yellow solid. GC:96.2%, yield 96%.

[0364] Compound 17;

[0365]

[0366] 30 g of compound 16 was dissolved in 200 mL of tetrahydrofuran and added to a three-necked flask. After nitrogen was replaced, the temperature was lowered to -78°C, and 110 mL of 1 mol / L lithium diisopropylamide was added dropwise at a temperature-controlled manner. The reaction was kept warm for 1 h. 104 mL of a 1 mol / L tetrahydrofuran solution of dibenzyl diselenide was added dropwise at a temperature-controlled manner at -78°C. The temperature was naturally raised to react for 2 h. After the reaction was quenched by adding water, the pH was adjusted to 4-5. The mixture was extracted with ethyl acetate, dried, and concentrated to obtain 29.7 g of an orange solid with a GC value of 94.7% and a yield of 71%.

[0367] Compound 18:

[0368]

[0369] 29.7 g of compound 17 was dissolved in 400 mL of dichloromethane and stirred at 0°C until completely dissolved. 13.6 g of boron tribromide was dissolved in 50 mL of dichloromethane and added dropwise to the above solution. The reaction was kept warm for 1 h. 200 mL of water was added to quench the reaction. The product was extracted twice with 200 mL of dichloromethane and dried. After concentration, it was purified by column chromatography to obtain 19.7 g of a solid, GC: 95.2%, and a yield of 78%.

[0370] Compound Ⅰb-5-1:

[0371]

[0372] 19.7 g of compound 18 was dissolved in 200 mL of dimethyl sulfoxide and added to a three-necked flask. 5.2 g of potassium tert-butoxide was added and the temperature was raised to 120 °C for reaction for 8 h. After the reaction was completed, the reaction solution was poured into 600 mL of ice water for slurrying. A light yellow solid was obtained by filtration and purified by recrystallization from toluene and ethanol to obtain 10.6 g of a white solid, GC: 99.8%, yield 56%.

[0373] Synthesis example 5

[0374] Preparation of Liquid Crystalline Compound Ⅰb-2-11

[0375] Compound 19:

[0376]

[0377] 20.7 g of compound 5 was dissolved in 300 mL of tetrahydrofuran and added to a three-necked flask. After nitrogen was replaced, the temperature was lowered to -78°C, and 24 mL of 2.5 mol / L butyl lithium was added dropwise at a controlled temperature. The reaction was kept warm for 1 h. 7.6 g of tellurium powder was added at -60°C. After 15 minutes of addition, the mixture was kept warm and stirred for half an hour. When the temperature naturally rose to 0°C, the mixture was poured into 300 mL of water for hydrolysis. The liquids were separated, and the aqueous phase was extracted twice with 200 mL of ethyl acetate. The organic layers were combined and washed with water until neutral. The solvent was evaporated under reduced pressure, and column chromatography was performed to obtain 17.3 g of compound 19 in a yield of 64%.

[0378] Using compound 19 as the starting material, replacing compound 7 in Synthesis Example 2, and synthesizing according to the steps of compound Ib-2-1, the compound represented by formula Ib-2-11 can be obtained:

[0379] .

[0380] According to the above method, compound 1 in Synthesis Example 1 is synthesized according to the synthesis method of compound 19 to obtain a tellurol intermediate, and then synthesized according to the steps of compound 1a-1-2 to obtain the compound represented by formula 1a-1-12:

[0381] .

[0382] The liquid crystal monomer structure of the application examples of the present invention is represented by codes, and the code representation method of the liquid crystal ring structure, end group, and connecting group is shown in Tables 1 and 2 below.

[0383] Table 1 Corresponding codes of ring structures

[0384]

[0385] Table 2 Corresponding codes of end groups and linking groups

[0386]

[0387] For example:

[0388] , whose code is PPY-3-O2;

[0389] , whose code is CPY-2-O2;

[0390] , whose code is CCY-3-O2;

[0391] , whose code is COY-3-O2;

[0392] , whose code is CCOY-3-O2;

[0393] , whose code is CLY-3-O2;

[0394] , its code is Sb-CpO-O4;

[0395] , whose code is Sc-CpO-O4;

[0396] , its code is Se-CpO-O4.

[0397] Application Examples 1-1 and 1-2

[0398] Liquid crystal compositions of Application Examples 1-1 and 1-2 were prepared according to the compounds listed in Table 3 and their corresponding mass percentages, and filled into corresponding test boxes for performance testing. The test results are shown in Table 4 below.

[0399] Table 3 Formulations of the liquid crystal compositions in Application Examples 1-1 and 1-2 and Comparative Example 1

[0400]

[0401] Table 4 Performance parameter test results of the liquid crystal compositions in Application Examples 1-1 and 1-2 and Comparative Example 1

[0402]

[0403] Comparative Application Example 1

[0404] The liquid crystal composition of Comparative Application Example 1 was prepared according to the compounds listed in Table 3 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 4.

[0405] Comparing the performance of the two formulations of application examples 1-1 and 1-2 with that of application comparative example 1, it can be seen that the K ave Increase by 3%, ε ⊥ / Δε increased by 6%, and the absolute value of Flicker increased by 3.1dB; K ave Increased by 4%, ε ⊥ / Δε increases by 8%, and the absolute value of Flicker increases by 3.0dB.

[0406] The other components in Application Examples 1-1 and 1-2 are the same as those in Application Comparative Example 1, and the only difference is that the structures of the compounds Se-2O-OT and Te-2O-OT in the embodiments of the present invention and the compound Sc-2O-OT in the prior art comparative example are different. It can be seen that the difluorodibenzoselenophene and difluorodibenzotellurophene monomers in Application Examples 1-1 and 1-2 have significantly improved performance compared with the difluorodibenzothiophene monomer in Application Comparative Example 1.

[0407] Application Examples 2-1 and 2-2

[0408] Liquid crystal compositions of application examples 2-1 and 2-2 were prepared according to the compounds listed in Table 5 and their corresponding mass percentages, and filled into corresponding test boxes for performance testing. The test results are shown in Table 6 below.

[0409] Table 5 Formulations of the liquid crystal compositions in Application Examples 2-1 and 2-2 and Comparative Example 2

[0410]

[0411] Table 6 Performance parameter test results of the liquid crystal compositions in Application Examples 2-1 and 2-2 and Comparative Example 2

[0412]

[0413] Application Comparative Example 2

[0414] The liquid crystal composition of Comparative Application Example 2 was prepared according to the compounds listed in Table 5 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 6 above.

[0415] Comparing the performance of the two formulations of application examples 2-1 and 2-2 with that of application comparative example 2, it can be seen that the K ave Increased by 4%, ε ⊥ / Δε increased by 5%, and the absolute value of Flicker increased by 3.6dB; K ave Increase by 5%, ε ⊥ / Δε increased by 8%, and the absolute value of Flicker increased by 3.4dB.

[0416] The other components of Application Examples 2-1 and 2-2 are the same as those of Application Comparative Example 2, and the only difference is that the structures of the embodiment compounds LSe-3-OT and LTe-3-OT of the present invention and the prior art comparative example compound LSc-3-OT are different. It can be seen that the difluorodibenzoselenophene and difluorodibenzotellurophene monomers contained in Application Examples 2-1 and 2-1 have significantly improved performance compared with the difluorodibenzothiophene monomer contained in Application Comparative Example 2.

[0417] Application Examples 3-1 and 3-2

[0418] Liquid crystal compositions of application examples 3-1 and 3-2 were prepared according to the compounds listed in Table 7 and their corresponding mass percentages, and filled into corresponding test boxes for performance testing. The test results are shown in Table 8 below.

[0419] In Table 7, the mass percentage of the compounds described in sequence numbers 1-12 is relative to the total mass of the compounds described in sequence numbers 1-12; the mass percentage of the compound described in sequence number 13 is also relative to the total mass of the compounds described in sequence numbers 1-12.

[0420] Table 7 Formulations of the liquid crystal compositions in Application Examples 3-1 and 3-2 and Comparative Example 3

[0421]

[0422] Table 8 Performance parameter test results of the liquid crystal compositions in Application Examples 3-1 and 3-2 and Comparative Example 3

[0423]

[0424] Comparing the performance of the two formulations of application examples 3-1 and 3-2 with that of application comparative example 3, it can be seen that the K ave Increase by 3%, ε ⊥ / Δε increased by 6%, and the absolute value of Flicker increased by 3.2dB; K ave Increased by 4%, ε ⊥ / Δε is increased by 12%, and the absolute value of Flicker is increased by 3.0dB.

[0425] Application Examples 3-1 and 3-2 have the same other components as those in Application Comparative Example 3, with the only difference being that the structures of the compounds CSe-2-OT and CTe-2-OT in the embodiments of the present invention and the compound CSc-2-OT in the prior art comparative example are different. It can be seen that the difluorodibenzoselenophene and difluorodibenzotellurophene monomers contained in Application Examples 3-1 and 3-2 have significantly improved performance compared with the difluorodibenzothiophene monomer contained in Application Comparative Example 3.

[0426] Application Example 4

[0427] The liquid crystal composition of Application Example 4 was prepared according to the compounds listed in Table 9 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 10 below.

[0428] In Table 9, the mass percentage of each compound described by sequence numbers 1-13 is relative to the total mass of the compounds described by sequence numbers 1-13; the mass percentage of the compound described by sequence number 14 is also relative to the total mass of the compounds described by sequence numbers 1-13.

[0429] Table 9 Formula composition of liquid crystal composition of Application Example 4

[0430]

[0431] Table 10 Performance parameter test results of the liquid crystal composition of Application Example 4

[0432]

[0433] Application Example 5

[0434] The liquid crystal composition of Application Example 5 was prepared according to the compounds listed in Table 11 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 12 below.

[0435] In Table 11, the mass percentage of each compound described by sequence number 1-15 is relative to the total mass of the compounds described by sequence number 1-15; the mass percentage of the compound described by sequence number 16 is also relative to the total mass of the compounds described by sequence number 1-15.

[0436] Table 11 Formulation of the liquid crystal composition of Application Example 5

[0437]

[0438] Table 12 Performance parameter test results of the liquid crystal composition of Application Example 5

[0439]

[0440] Application Example 6

[0441] The liquid crystal composition of Application Example 6 was prepared according to the compounds listed in Table 13 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 14 below.

[0442] In Table 13, the mass percentage of the compounds described in sequence numbers 1-18 is relative to the total mass of the compounds described in sequence numbers 1-18; the mass percentage of the compound described in sequence number 19 is also relative to the total mass of the compounds described in sequence numbers 1-18.

[0443] Table 13 Formulation of the liquid crystal composition of Application Example 6

[0444]

[0445] Table 14 Performance parameter test results of the liquid crystal composition of Application Example 6

[0446]

[0447] Application Example 7

[0448] The liquid crystal composition of Application Example 7 was prepared according to the compounds listed in Table 15 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 16 below.

[0449] In Table 15, the mass percentage of each compound described by sequence numbers 1-19 is relative to the total mass of the compounds described by sequence numbers 1-19; the mass percentage of the compound described by sequence number 20 is also relative to the total mass of the compounds described by sequence numbers 1-19.

[0450] Table 15 Formulation of the liquid crystal composition of Application Example 7

[0451]

[0452] Table 16 Performance parameter test results of the liquid crystal composition of Application Example 7

[0453]

[0454] Application Example 8

[0455] The liquid crystal composition of Application Example 8 was prepared according to the compounds listed in Table 17 and the corresponding mass percentages, and filled into the corresponding test box for performance testing. The test results are shown in Table 18 below.

[0456] In Table 17, the mass percentage of each compound described by sequence number 1-20 is relative to the total mass of the compounds described by sequence number 1-20; the mass percentage of the compound described by sequence number 21 is also relative to the total mass of the compounds described by sequence number 1-20.

[0457] Table 17 Formulation of the liquid crystal composition of Application Example 8

[0458]

[0459] Table 18 Performance parameter test results of the liquid crystal composition of Application Example 8

[0460]

[0461] In summary, the liquid crystal compound provided in the present invention has a main ring molecular structure containing difluorodibenzoselenophene and difluorodibenzotellurophene structures, and a terminal group at one end of the main ring contains a specific polar group X1. The liquid crystal compound has a high ratio of vertical dielectric constant to dielectric anisotropy ε ⊥ / Δε, high average elastic constant K ave , excellent Flicker performance; the liquid crystal composition of the present invention comprising the liquid crystal compound has a high ratio of vertical dielectric constant to dielectric anisotropy ε ⊥ / Δε, high average elastic constant K ave , excellent Flicker performance, can be used to develop liquid crystal display devices with high transmittance, low energy consumption, high contrast and high refresh rate.

[0462] Obviously, the above embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not limitations on the implementation methods of the present invention. For ordinary technicians in the relevant field, other different forms of changes or modifications can be made based on the above description. It is impossible to list all the implementation methods here. All obvious changes or modifications derived from the technical solution of the present invention are still within the scope of protection of the present invention.

Claims

1. A liquid crystal compound, characterized in that: The liquid crystal compound is a compound represented by the following formula I: Ⅰ in, R1 represents H, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, and furthermore, one or more H atoms in these groups may be replaced by halogen; Express the same or different meanings on each occurrence 、 or ,in One or more H atoms can be replaced by F; Z1, when present, represents, identically or differently, a single bond or an alkyl group having 1 to 5 carbon atoms, wherein any one or more unattached -CH2- in these groups may be replaced by -O-, and furthermore, one or more H atoms in these groups may be replaced by halogen; X1 represents Se or Te; X2 represents a fluorine atom, a perfluoroalkyl group having 1 to 5 carbon atoms, a perfluoroalkoxy group having 1 to 5 carbon atoms, a perfluoroalkenyl group having 2 to 5 carbon atoms, or a perfluoroalkenyloxy group having 2 to 5 carbon atoms; m1 represents 0, 1, or 2; When m1 represents 2, Same or different, Z1 same or different.

2. The liquid crystal compound according to claim 1, wherein The compound represented by formula I is selected from at least one of the following compounds: Ⅰa、 Ⅰb in, R 11 represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, and furthermore, one or more H atoms in these groups may be replaced by halogen; Z 11 represents a single bond or an alkyl group having 1 to 5 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-.

3. The liquid crystal compound according to claim 2, characterized in that The compound represented by formula I is selected from at least one of the following compounds: Ⅰa-1、 Ⅰb-1、 Ⅰb-2、 Ⅰb-3、 Ⅰb-4、 Ⅰb-5、 Ⅰb-6、 Ⅰb-7 in, R 12 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups in these groups may be replaced by -O-, and furthermore, one or more H atoms in these groups may be replaced by halogen.

4. A liquid crystal composition, characterized in that The liquid crystal composition comprises one or more liquid crystal compounds according to any one of claims 1 to 3.

5. The liquid crystal composition according to claim 4, characterized in that Calculated by mass percentage, the liquid crystal composition contains 0.1-30% of the compound represented by formula I.

6. The liquid crystal composition according to claim 4, wherein The liquid crystal composition further comprises at least one compound represented by formula II: Ⅱ in, and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F; R2 and R3 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement; Z2 represents -CH2-CH2-, -CF2-CF2-, -CF=CF-, -O-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond.

7. The liquid crystal composition according to claim 6, wherein The liquid crystal composition further comprises at least one compound represented by formula III: Ⅲ in, and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F; R4 and R5 independently represent an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms or an alkynyl group having 1 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement; Z3 represents -CH2-CH2-, -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -C≡C- or a single bond; m2 means 2, 3 or 4; When m2 represents 2, 3 or 4, Same or different, Z3 same or different.

8. The liquid crystal composition according to claim 7, wherein The liquid crystal composition further comprises at least one compound represented by formula IV-1 and / or IV-2: Ⅳ-1、 Ⅳ-2 in, 、 and Each independently expresses 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F; express or ; R6 represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement; X3 represents F, CF3, OCF3 or CN; (F) each independently represents H or F; m3 and m5 each independently represent 1 or 2; m4 means 1, 2 or 3; When m3 represents 2, Same or different; When m4 represents 2 or 3, Same or different; When m5 represents 2, Same or different.

9. The liquid crystal composition according to claim 8, characterized in that Calculated by mass percentage, the liquid crystal composition contains 0.1-30% of the compound represented by formula I, 30-70% of the compound represented by formula II, 10-40% of the compound represented by formula III, and 5-35% of the compound represented by formula IV-1 and / or IV-2.

10. The liquid crystal composition according to claim 8, characterized in that The liquid crystal composition comprises at least one compound represented by formula V: Ⅴ in, express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, At most one H atom can be replaced by F; R a 、R b Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 or Replacement; Z4 represents -CH2-CH2-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O-, -C≡C- or a single bond; n1 represents 0, 1, or 2; n2 represents 0 or 1; When n1 represents 2, Same or different, Z4 same or different.

11. The liquid crystal composition according to claim 8 or 10, characterized in that The liquid crystal composition further comprises at least one compound represented by formula VI: Ⅵ in, R c 、R d Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, wherein any one or more unconnected -CH2- groups may be replaced by -O-, 、 、 、 or Replacement; X4 represents -O-, -S-, -Se- or -CH2O-; Z5 represents -O-, -CO-, -CO-O-, -O-CO-, -CH2O-, -OCH2-, -CH=CH-, -CF2O- or a single bond; express 、 or ,in One or more unconnected -CH2- can be replaced by -O-, One or more H atoms can be replaced by F; n3 represents 0, 1, or 2; When n3 represents 2, Same or different, Z5 same or different.

12. A liquid crystal display device, characterized in that: Comprising the liquid crystal composition according to any one of claims 4 to 11.

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