WO2024099123A1 - Liquid crystal composition and display panel - Google Patents

Liquid crystal composition and display panel Download PDF

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Publication number
WO2024099123A1
WO2024099123A1 PCT/CN2023/127457 CN2023127457W WO2024099123A1 WO 2024099123 A1 WO2024099123 A1 WO 2024099123A1 CN 2023127457 W CN2023127457 W CN 2023127457W WO 2024099123 A1 WO2024099123 A1 WO 2024099123A1
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substituted
carbon atoms
liquid crystal
crystal composition
unsubstituted
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PCT/CN2023/127457
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French (fr)
Chinese (zh)
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刘晓
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惠州华星光电显示有限公司
Tcl华星光电技术有限公司
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Publication of WO2024099123A1 publication Critical patent/WO2024099123A1/en

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  • the present invention relates to the field of display technology, and in particular to a liquid crystal composition and a display panel.
  • Liquid crystal materials are widely used in displays.
  • the contrast and response speed of liquid crystal materials are key factors in improving the display performance of displays.
  • the optical, electrical and mechanical properties of liquid crystal molecules depend on the structure and substituent groups of the liquid crystal molecules.
  • the embodiments of the present invention provide a liquid crystal composition and a display panel to solve the technical problem that the response speed of existing liquid crystal materials needs to be improved.
  • An embodiment of the present invention provides a liquid crystal composition, including a first compound, wherein the structural formula of the first compound is as shown in Formula I:
  • a 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
  • K 1 and K 2 are independently selected from H or F, and are not H at the same time;
  • n and n are independently selected from integers between 0 and 2, and are not both 0;
  • Each independently selected from substituted or unsubstituted heteroatoms having 3 to 5 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, a substituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings;
  • R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH
  • m and n are independently selected from 0 or 1, and are not 0 at the same time.
  • Z 1 and Z 2 are independently selected from CH 2 , NH, O or S.
  • R 1 and R 2 are independently selected from substituted or unsubstituted alkyl having 1 to 7 carbon atoms, substituted or unsubstituted alkenyl having 1 to 7 carbon atoms, or substituted or unsubstituted alkynyl having 1 to 7 carbon atoms, wherein one or both CH 2 of R 1 and R 2 are independently substituted by -O-, -CO, -C(O)O-, -OC(O)-, -CF 2 O-, -OCF 2 -, -CH 2 O or -OCH 2 -, and the heteroatom is not directly bonded.
  • the first compound is selected from at least one of the following formulas I-1 to I-4:
  • Alkyl is independently selected from an alkyl group in which at least one carbon atom is substituted by -O-, -CO-, -OC(O)-, -OCF2- or -OCH2- and the heteroatom is not directly bonded, an alkenyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF2O- or -CH2O and the heteroatom is not directly bonded, or an alkyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF2O- or -CH2O and the heteroatom is not directly bonded.
  • Alkynyl groups substituted with -CF2O- or -CH2O and not directly bonded to heteroatoms, wherein the alkyl group has 1 to 15 carbon atoms, the alkenyl group has 2 to 15 carbon atoms, and the alkynyl group has 2 to 15 carbon atoms.
  • the first compound is selected from at least one of the following formulas I-1-1 to I-1-9, I-3-1 to I-3-27:
  • the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
  • R 3 and R 4 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, and substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
  • the liquid crystal composition comprises 1% to 90% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 5% to 70% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 10% to 50% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition further comprises a third compound, and the third compound is shown in Formula III1 to III5:
  • R 5 and R 6 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, and substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
  • the liquid crystal composition comprises 1% to 90% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 5% to 70% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 10% to 50% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 1% to 50% of the first compound represented by Formula I relative to the weight of the liquid crystal composition.
  • the liquid crystal composition comprises 1% to 25% of the first compound represented by Formula I relative to the weight of the liquid crystal composition.
  • An embodiment of the present invention further provides a display panel, comprising an array substrate and a color filter substrate arranged opposite to each other, and a liquid crystal layer sandwiched between the array substrate and the color filter substrate, wherein the material of the liquid crystal layer is The material includes a liquid crystal composition, wherein the liquid crystal composition includes a first compound, and the structural formula of the first compound is shown in Formula I:
  • a 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
  • K 1 and K 2 are independently selected from H or F, and are not H at the same time;
  • n and n are independently selected from integers between 0 and 2, and are not both 0;
  • R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH
  • the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
  • R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
  • the liquid crystal composition further comprises a third compound, and the third compound is shown in Formula III1 to III5:
  • R 5 and R 6 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
  • the liquid crystal composition provided by the embodiment of the present invention includes fluorinated benzofuran liquid crystal compounds, which have high negative dielectric anisotropy, good liquid crystal mutual solubility, relatively low rotational viscosity, etc., and can be applied to display devices to reduce response time and improve contrast.
  • FIG. 1 is a schematic diagram of the structure of a display panel provided by an embodiment of the present invention.
  • An embodiment of the present invention provides a liquid crystal composition, which includes a first compound, a second compound and a third compound.
  • the structural formula of the first compound is shown in Formula I below:
  • a 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms. Further, A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 5 carbon atoms, or an alkyleneoxy group having 1 to 5 carbon atoms. Further, A 1 and A 2 are independently selected from a single bond or O. Preferably, A 1 and A 2 are O.
  • K 1 and K 2 are independently selected from H or F, and are not H at the same time.
  • n and n are independently selected from integers ranging from 0 to 2, and are not 0 at the same time. Further, m and n are independently selected from 0 or 1, and are not 0 at the same time.
  • R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms.
  • one or more H in the above alkyl, alkenyl, or alkynyl group may be independently substituted by F, Cl, Br, or I.
  • R 1 and R 2 are alkyl, alkenyl or alkynyl
  • the terminal groups of R 1 and R 2 may be independently substituted by CN or CF 3 .
  • R1 and R2 are independently selected from substituted or unsubstituted alkyl having 1 to 7 carbon atoms, substituted or unsubstituted alkenyl having 1 to 7 carbon atoms, or substituted or unsubstituted alkynyl having 1 to 7 carbon atoms.
  • one or both CH2 in R1 and R2 are independently substituted by -O-, -CO, -C(O)O-, -OC(O)-, -CF2O- , -OCF2- , -CH2O or -OCH2- , and the heteroatom is not directly bonded.
  • Each Each The number of carbon atoms independently selected from substituted or unsubstituted is a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings; specifically, each and each One or more H on R can be independently replaced by F, Cl, Br, or I.
  • each independently selected from any one of the following structural formulas:
  • R1 and R2 are preferably alkyl groups having 1 to 7 carbon atoms, and particularly preferably alkyl groups having 2 to 5 carbon atoms. Further, when A2 is a single bond or an O atom, R2 is preferably an alkyl group, an alkenyl group or an alkynyl group, and particularly preferably an alkyl group having 1 to 7 carbon atoms.
  • the total number of carbon atoms in R1 and R2 is preferably 4, 5, 6, 7, 8, 9, or 10, and particularly preferably 5, 6, 7, 8, or 9.
  • R1 and R2 are preferably alkyl groups having 1 to 7 carbon atoms, particularly preferably 2 to 5 carbon atoms. Further, when A2 is a single bond or O, R2 is preferably an alkyl group, an alkenyl group or an alkynyl group, particularly preferably an alkyl group having 1 to 7 carbon atoms.
  • the total number of carbon atoms in R1 and R2 is preferably 4, 5, 6, 7, 8, 9, or 10, particularly preferably 5, 6, 7, 8, or 9.
  • R1 and R2 when R1 and R2 independently represent an alkyl group, the alkyl group may be straight-chain or branched.
  • R1 and R2 are preferably straight-chain and independently have 1 to 7 carbon atoms, i.e., preferably methyl, ethyl, propyl, butyl, pentyl, hexyl or heptyl.
  • R1 and R2 when R1 and R2 independently represent an alkenyl group having 2 to 15 carbon atoms or an alkynyl group having 2 to 15 carbon atoms, the alkenyl group and the alkynyl group may be straight-chain or branched.
  • R1 and R2 are preferably alkenyl groups having 2 to 7 carbon atoms or alkynyl groups having 2 to 7 carbon atoms.
  • R1 and R2 are independently selected from vinyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, ethynyl,
  • the alkene groups are prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3
  • the invention further comprises the following: 1.
  • a pent-4-enyl group 2. a pent-3-enyl group, 3. a pent-4-enyl group, 4. a pent-5-enyl group, 5. a pent-6-enyl group, 6. a pent-7-enyl group, 7. a pent-8-enyl group, 8. a pent-9-enyl group, 9. a pent-10-enyl group, 9
  • the first compound is preferably at least one of Formula I-1 to Formula I-4:
  • Alkyl is selected from an alkyl group having 1-15 carbon atoms, an alkenyl group having 2-15 carbon atoms, or an alkynyl group having 2-15 carbon atoms.
  • one or two CH2 groups in the Alkyl group can be independently substituted by -O-, -CO-, -OC(O)-, -OCF2-, -CH2O or -OCH2- and the heteroatom is not directly bonded.
  • the alkyl group is preferably a straight chain having 1 to 7 carbon atoms.
  • the first compound is preferably a compound in which A1 and A2 are single bonds or O, and is preferably at least one of the structures shown in Formulas I-1-1 to I-1-9, I-3-1 to I-3-27:
  • the first compound I mentioned in any of the above embodiments itself and its groups and substituents have asymmetric centers or chiral centers and can exist in the form of isomers, such as pure enantiomers, diastereomers, E or Z isomers, or as a mixture of multiple isomers in any desired proportion, for example, as a racemate, E/Z isomer mixture.
  • the first compound I of the embodiment of the present invention is a fluorinated benzofuran liquid crystal compound, which has high negative dielectric anisotropy, good liquid crystal mutual solubility, relatively low rotational viscosity, etc. When used in display devices, it can reduce the response time and improve the contrast.
  • the selected groups have the same range, i.e.
  • the group is independently selected from a substituted or unsubstituted heteroatom having 3 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings.
  • the synthesis route of the first compound is the same as or similar to the synthesis route of the above embodiment.
  • R 3 and R 4 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
  • at least one H in R 3 and R 4 may be independently substituted by F, Cl, Br, or I.
  • the third compound is shown in the following formula III1 to III5:
  • R 5 and R 6 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
  • at least one H in R 5 and R 6 may be independently substituted by F, Cl, Br, or I.
  • the liquid crystal composition includes the following components in weight percentage: 1% to 50% of the first compound shown in formula I; 1% to 90% of the second compound shown in formulas II1 to II9; and 1% to 90% of the compounds shown in formulas III1 to III5.
  • the liquid crystal composition may also contain other functional materials, such as chiral agents, initiators, inhibitors, organic solvents and other additives, when applied to a display device.
  • the liquid crystal composition of the embodiment of the present invention comprises the following components in weight percentage: 1% to 40% of the first compound represented by formula I; 5% to 70% of the second compound represented by formula II1 to II9;
  • the liquid crystal composition comprises the following components in weight percentage: 1% to 25% of the first compound represented by formula I; 10% to 50% of the second compound represented by formula II1 to II9;
  • the preparation of the liquid crystal composition can be prepared by a thermal dissolution method, comprising the following steps:
  • the inventors conducted mixed crystal experiments on the prepared liquid crystal composition, as shown in Tables 1 to 6.
  • the performance parameters of the liquid crystal composition of the embodiment of the present invention were obtained, wherein the specific meanings of the performance parameters in the table are as follows: the temperature unit is °C; Tni represents the clearing point of the liquid crystal composition (unit: °C); ⁇ n represents the optical anisotropy at 25°C, ne is the refractive index of extraordinary light; ⁇ 1 represents the rotational viscosity at 25°C (unit: mPa ⁇ s); ⁇ represents the dielectric anisotropy at 25°C, ⁇ is the dielectric constant perpendicular to the long axis of the liquid crystal molecule; K11 is the splay elastic coefficient, and K33 is the bending elastic coefficient.
  • the contrast of liquid crystal is related to the dielectric anisotropy of the liquid crystal.
  • the contrast can be improved.
  • the dielectric anisotropy ⁇ of the liquid crystal composition of the embodiment of the present invention is between -3.8 and -3.5, and has a relatively high dielectric negativity, so the contrast of the liquid crystal composition can be improved.
  • the response time of the liquid crystal is positively correlated with the rotational viscosity ⁇ 1, and negatively correlated with the dielectric anisotropy ⁇ and the splay elastic coefficient K11 ;
  • the first compound has a higher dielectric negativity, which can improve the dielectric negativity of the liquid crystal and reduce the response time;
  • the second compound has dielectric neutrality and low viscosity, which can reduce the viscosity of the liquid crystal and reduce the response time;
  • the third compound has dielectric negativity, and ⁇ n, Tni and viscosity can be adjusted according to needs to adjust the liquid crystal properties as a whole.
  • the rotational viscosity ⁇ 1 of the liquid crystal composition provided in the embodiment of the present invention is between 77 and 98 mPa ⁇ s, with low rotational viscosity, which can reduce the response time; K11 is between 14.1 and 14.7, with a higher splay elastic coefficient, which can reduce the response time; the dielectric anisotropy ⁇ is between -3.8 and -3.5,
  • the liquid crystal composition has a high dielectric negativity and can reduce the response time; and the clearing point Tni of the liquid crystal composition is above 85°C, has a high clearing point, and can have an ideal liquid crystal phase in a wide temperature range.
  • the embodiment of the present invention further provides a display panel 100, comprising an array substrate 10 and a color filter substrate 30 arranged opposite to each other, and a liquid crystal layer 20 sandwiched between the array substrate 10 and the color filter substrate 30, wherein the material of the liquid crystal layer 20 comprises the liquid crystal composition of the above embodiment.
  • the above liquid crystal composition is applied to the display panel, which can reduce the response time of the display panel and improve the contrast of the display panel.
  • the array substrate 10 of the display panel 100 includes a thin film transistor array, which is used to drive the liquid crystal layer to emit light.
  • the display panel 100 also includes a backlight module disposed on the side of the array substrate 10 away from the liquid crystal layer 20, which is used to provide a backlight source for the liquid crystal layer 20.
  • the liquid crystal composition can be applied to displays such as watches, mobile phones, televisions and computers, and is applicable to displays of types such as VA, ECB, PALC, FFS or IPS.

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Abstract

Disclosed in the embodiments of the present invention are a liquid crystal composition and a display panel. The liquid crystal composition comprises a first compound, wherein the structural formula of the first compound is as represented by formula (I).

Description

液晶组合物、显示面板Liquid crystal composition, display panel 技术领域Technical Field
本发明涉及显示技术领域，具体涉及一种液晶组合物、显示面板。The present invention relates to the field of display technology, and in particular to a liquid crystal composition and a display panel.
背景技术Background technique
液晶材料广泛应用于显示器中，液晶材料的对比度和响应速度是提升显示器的显示性能的关键因素，液晶分子的光学、电学和力学的性质取决于液晶分子的结构及取代基团。Liquid crystal materials are widely used in displays. The contrast and response speed of liquid crystal materials are key factors in improving the display performance of displays. The optical, electrical and mechanical properties of liquid crystal molecules depend on the structure and substituent groups of the liquid crystal molecules.
随着显示器件的不断发展，亟需开发出一种响应更快的液晶材料。With the continuous development of display devices, there is an urgent need to develop a liquid crystal material with faster response.
技术问题technical problem
本发明实施例提供一种液晶组合物、显示面板，以解决现有的液晶材料的响应速度有待于提高的技术问题。The embodiments of the present invention provide a liquid crystal composition and a display panel to solve the technical problem that the response speed of existing liquid crystal materials needs to be improved.
技术解决方案Technical Solutions
为解决上述问题，本申请提供的技术方案如下：To solve the above problems, the technical solutions provided by this application are as follows:
本发明实施例提供一种液晶组合物，包括第一化合物，所述第一化合物的结构式如式Ⅰ所示： An embodiment of the present invention provides a liquid crystal composition, including a first compound, wherein the structural formula of the first compound is as shown in Formula I:
其中，A1、A2独立地选自单键、O、S、具有1～7个碳原子的亚烷基，或具有1～7个碳原子的亚烷氧基；wherein A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
K1、K2独立地选自H或F，且不同时为H；K 1 and K 2 are independently selected from H or F, and are not H at the same time;
m、n独立地选自0～2中的整数，且不同时为0；m and n are independently selected from integers between 0 and 2, and are not both 0;
每个每个独立地选自取代或未取代的碳原子数为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取 代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基；Each Each independently selected from substituted or unsubstituted heteroatoms having 3 to 5 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, a substituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings;
R1、R2独立地选自H、F、Cl、Br、I、CN、SCN、NCS、SF5、取代或未取代的碳原子数为1～15个碳原子的烷基、取代或未取代的碳原子数为2～15的烯基，或取代或未取代的碳原子数为2～15的炔基，其中，R1、R2为烷基、烯基或炔基时，R1、R2中的至少一个CH2独立地被-O-、-S-、-SO2-、-CO-、-C(O)O-、-OC(O)O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CF2CHF-、-CF2CH2-、-CHF-CHF-、-CHF-CH2-、-CH2O、-CF＝CH-、-CF＝CF-、-CH＝CH-或-C≡C-取代并使杂原子不直接键接，和/或R1、R2的末端基团独立地被CN或CF3取代。R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH 2 O, -CF=CH-, -CF=CF-, -CH=CH- or -C≡C- and the hetero atom is not directly bonded, and/or the terminal groups of R 1 and R 2 are independently substituted by CN or CF 3 .
在本发明的一些实施例中，m、n独立地选自0或1，且不同时为0。In some embodiments of the present invention, m and n are independently selected from 0 or 1, and are not 0 at the same time.
在本发明的一些实施例中，每个每个独立地选自以下结构式中的任意一种：
In some embodiments of the present invention, each Each Independently selected from any one of the following structural formulas:
其中，Z1、Z2独立地选自CH2、NH、O或S。Wherein, Z 1 and Z 2 are independently selected from CH 2 , NH, O or S.
在本发明的一些实施例中，每个每个独立地选自以下结构式中的任意一种：
In some embodiments of the present invention, each Each Independently selected from any one of the following structural formulas:
在本发明的一些实施例中，R1、R2独立地选自取代或未取代的碳原子数为1～7的烷基、取代或未取代的碳原子数为1～7的烯基，或取代或未取代的碳原子数为1～7的炔基，其中，R1、R2中的一个或两个CH2独立地被-O-、-CO、-C(O)O-、-OC(O)-、-CF2O-、-OCF2-、-CH2O或-OCH2-取代并使杂原子不直接键接。In some embodiments of the present invention, R 1 and R 2 are independently selected from substituted or unsubstituted alkyl having 1 to 7 carbon atoms, substituted or unsubstituted alkenyl having 1 to 7 carbon atoms, or substituted or unsubstituted alkynyl having 1 to 7 carbon atoms, wherein one or both CH 2 of R 1 and R 2 are independently substituted by -O-, -CO, -C(O)O-, -OC(O)-, -CF 2 O-, -OCF 2 -, -CH 2 O or -OCH 2 -, and the heteroatom is not directly bonded.
在本发明的一些实施例中，所述第一化合物选自如下式Ⅰ-1至式Ⅰ-4所示的至少一种：
In some embodiments of the present invention, the first compound is selected from at least one of the following formulas I-1 to I-4:
其中，Alkyl独立地选自至少一个碳原子被-O-、-CO-、-OC(O)-、-OCF2-或-OCH2-取代并使杂原子不直接键接的烷基，至少一个碳原子被-O-、-CO-、-C(O)O-、-CF2O-或-CH2O取代并使杂原子不直接键接的烯基，或至少一个碳原子被-O-、-CO-、-C(O)O-、 -CF2O-或-CH2O取代并使杂原子不直接键接的炔基，其中，烷基的碳原子数为1～15，烯基的碳原子数为2～15，炔基的碳原子数为2～15。 wherein Alkyl is independently selected from an alkyl group in which at least one carbon atom is substituted by -O-, -CO-, -OC(O)-, -OCF2- or -OCH2- and the heteroatom is not directly bonded, an alkenyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF2O- or -CH2O and the heteroatom is not directly bonded, or an alkyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF2O- or -CH2O and the heteroatom is not directly bonded. Alkynyl groups substituted with -CF2O- or -CH2O and not directly bonded to heteroatoms, wherein the alkyl group has 1 to 15 carbon atoms, the alkenyl group has 2 to 15 carbon atoms, and the alkynyl group has 2 to 15 carbon atoms.
在本发明的一些实施例中，所述第一化合物选自如下式Ⅰ-1-1至Ⅰ-1-9、Ⅰ-3-1至Ⅰ-3-27所示的至少一种：

In some embodiments of the present invention, the first compound is selected from at least one of the following formulas Ⅰ-1-1 to Ⅰ-1-9, Ⅰ-3-1 to Ⅰ-3-27:

在本发明的一些实施例中，所述液晶组合物还包括第二化合物，所述第二化合物如式Ⅱ1至Ⅱ9所示：
In some embodiments of the present invention, the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
R3、R4独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基、取代或未被取代的碳原子数为2～10的炔氧基。 R 3 and R 4 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, and substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～90％的式Ⅱ1至Ⅱ9所示的第二化合物。In some embodiments of the present invention, the liquid crystal composition comprises 1% to 90% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括5％～70％的式Ⅱ1至Ⅱ9所示的第二化合物。In some embodiments of the present invention, the liquid crystal composition comprises 5% to 70% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括10％～50％的式Ⅱ1至Ⅱ9所示的第二化合物。In some embodiments of the present invention, the liquid crystal composition comprises 10% to 50% of the second compound represented by formula II1 to II9, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，所述液晶组合物还包括第三化合物，所述第三化合物如式Ⅲ1至Ⅲ5所示：
In some embodiments of the present invention, the liquid crystal composition further comprises a third compound, and the third compound is shown in Formula III1 to III5:
其中，R5、R6独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基、取代或未被取代的碳原子数为2～10的炔氧基。 wherein R 5 and R 6 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, and substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～90％的式Ⅲ1至Ⅲ5所示的化合物。In some embodiments of the present invention, the liquid crystal composition comprises 1% to 90% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括5％～70％的式Ⅲ1至Ⅲ5所示的化合物。In some embodiments of the present invention, the liquid crystal composition comprises 5% to 70% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括10％～50％的式Ⅲ1至Ⅲ5所示的化合物。In some embodiments of the present invention, the liquid crystal composition comprises 10% to 50% of the compounds represented by formulae III1 to III5, relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～50％的式I所示的第一化合物。In some embodiments of the present invention, the liquid crystal composition comprises 1% to 50% of the first compound represented by Formula I relative to the weight of the liquid crystal composition.
在本发明的一些实施例中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～25％的式I所示的第一化合物。In some embodiments of the present invention, the liquid crystal composition comprises 1% to 25% of the first compound represented by Formula I relative to the weight of the liquid crystal composition.
本发明的实施例还提供一种显示面板，包括相对设置的阵列基板和彩膜基板，以及夹设于所述阵列基板和所述彩膜基板之间的液晶层，所述液晶层的材 料包括液晶组合物，所述液晶组合物包括第一化合物，所述第一化合物的结构式如式Ⅰ所示： An embodiment of the present invention further provides a display panel, comprising an array substrate and a color filter substrate arranged opposite to each other, and a liquid crystal layer sandwiched between the array substrate and the color filter substrate, wherein the material of the liquid crystal layer is The material includes a liquid crystal composition, wherein the liquid crystal composition includes a first compound, and the structural formula of the first compound is shown in Formula I:
其中，A1、A2独立地选自单键、O、S、具有1～7个碳原子的亚烷基，或具有1～7个碳原子的亚烷氧基；wherein A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
K1、K2独立地选自H或F，且不同时为H；K 1 and K 2 are independently selected from H or F, and are not H at the same time;
m、n独立地选自0～2中的整数，且不同时为0；m and n are independently selected from integers between 0 and 2, and are not both 0;
每个每个独立地选自取代或未取代的碳原子数为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基；Each Each independently selected from a substituted or unsubstituted heteroatom having 3 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings;
R1、R2独立地选自H、F、Cl、Br、I、CN、SCN、NCS、SF5、取代或未取代的碳原子数为1～15个碳原子的烷基、取代或未取代的碳原子数为2～15的烯基，或取代或未取代的碳原子数为2～15的炔基，其中，R1、R2为烷基、烯基或炔基时，R1、R2中的至少一个CH2独立地被-O-、-S-、-SO2-、-CO-、-C(O)O-、-OC(O)O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CF2CHF-、-CF2CH2-、-CHF-CHF-、-CHF-CH2-、-CH2O、-CF＝CH-、-CF＝CF-、-CH＝CH-或-C≡C-取代并使杂原子不直接键接，和/或R1、R2的末端基团独立地被CN或CF3取代。R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH 2 O, -CF=CH-, -CF=CF-, -CH=CH- or -C≡C- and the hetero atom is not directly bonded, and/or the terminal groups of R 1 and R 2 are independently substituted by CN or CF 3 .
在本发明的一些实施例中，所述液晶组合物还包括第二化合物，所述第二化合物如式Ⅱ1至Ⅱ9所示：
In some embodiments of the present invention, the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
R3、R4独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
在本发明的一些实施例中，所述液晶组合物还包括第三化合物，所述第三化合物如式Ⅲ1至Ⅲ5所示：
In some embodiments of the present invention, the liquid crystal composition further comprises a third compound, and the third compound is shown in Formula III1 to III5:
其中，R5、R6独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 Wherein, R 5 and R 6 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
有益效果Beneficial Effects
本发明实施例提供的液晶组合物包括含氟苯并呋喃类液晶化合物，该类化合物具有较高的负介电各向异性、良好的液晶互溶性、相对低的旋转粘度等，应用于显示器件中，可减少响应时间、提高对比度。The liquid crystal composition provided by the embodiment of the present invention includes fluorinated benzofuran liquid crystal compounds, which have high negative dielectric anisotropy, good liquid crystal mutual solubility, relatively low rotational viscosity, etc., and can be applied to display devices to reduce response time and improve contrast.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
图1为本发明实施例提供的显示面板的结构示意图。FIG. 1 is a schematic diagram of the structure of a display panel provided by an embodiment of the present invention.
本发明的实施方式Embodiments of the present invention
本发明实施例提供一种液晶组合物，所述液晶组合物包括第一化合物、第二化合物以及第三化合物，所述第一化合物的结构式如下式I所示：
An embodiment of the present invention provides a liquid crystal composition, which includes a first compound, a second compound and a third compound. The structural formula of the first compound is shown in Formula I below:
其中，A1、A2独立地选自单键、O、S、具有1～7个碳原子的亚烷基，或具有1～7个碳原子的亚烷氧基。进一步地，A1、A2独立地选自单键、O、S、具有1～5个碳原子的亚烷基，或具有1～5个碳原子的亚烷氧基。更进一步地，A1、A2独立地选自单键或O。优选地，A1、A2为O。Wherein, A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms. Further, A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 5 carbon atoms, or an alkyleneoxy group having 1 to 5 carbon atoms. Further, A 1 and A 2 are independently selected from a single bond or O. Preferably, A 1 and A 2 are O.
K1、K2独立地选自H或F，且不同时为H。K 1 and K 2 are independently selected from H or F, and are not H at the same time.
m、n独立地选自0～2中的整数，且不同时为0。进一步地，m、n独立地选自0或1，且不同时为0。m and n are independently selected from integers ranging from 0 to 2, and are not 0 at the same time. Further, m and n are independently selected from 0 or 1, and are not 0 at the same time.
R1、R2独立地选自H、F、Cl、Br、I、CN、SCN、NCS、SF5、取代或未取代的碳原子数为1～15个碳原子的烷基、取代或未取代的碳原子数为2～15的烯基，或取代或未取代的碳原子数为2～15的炔基。具体地，上述烷基、烯基、或炔基中的一个或多个H可独立地被F、Cl、Br、I取代。R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms. Specifically, one or more H in the above alkyl, alkenyl, or alkynyl group may be independently substituted by F, Cl, Br, or I.
其中，R1、R2为烷基、烯基或炔基时，R1、R2中的一个或多个CH2可独立地被-O-、-S-、-SO2-、-CO-、-C(O)O-、-OC(O)O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CF2CHF-、-CF2CH2-、-CHF-CHF-、-CHF-CH2-、-CH2O、-CF＝CH-、-CF＝CF-、-CH＝CH-或-C≡C-取代并使杂原子不直接键接。R1、R2为烷基、烯基或炔基时，R1、R2的末端基团可独立地被CN或CF3取代。Wherein, when R 1 and R 2 are alkyl, alkenyl or alkynyl, one or more CH 2 in R 1 and R 2 may be independently substituted by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH 2 O, -CF＝CH-, -CF＝CF-, -CH＝CH- or -C≡C- and the heteroatom is not directly bonded. When R 1 and R 2 are alkyl, alkenyl or alkynyl, the terminal groups of R 1 and R 2 may be independently substituted by CN or CF 3 .
优选地，R1、R2独立地选自取代或未取代的碳原子数为1～7的烷基、取代或未取代的碳原子数为1～7的烯基，或取代或未取代的碳原子数为1～7的炔基。其中，R1、R2中的一个或两个CH2独立地被-O-、-CO、-C(O)O-、-OC(O)-、-CF2O-、-OCF2-、-CH2O或-OCH2-取代并使杂原子不直接键接。Preferably, R1 and R2 are independently selected from substituted or unsubstituted alkyl having 1 to 7 carbon atoms, substituted or unsubstituted alkenyl having 1 to 7 carbon atoms, or substituted or unsubstituted alkynyl having 1 to 7 carbon atoms. Wherein, one or both CH2 in R1 and R2 are independently substituted by -O-, -CO, -C(O)O-, -OC(O)-, -CF2O- , -OCF2- , -CH2O or -OCH2- , and the heteroatom is not directly bonded.
每个每个独立地选自取代或未取代的碳原子数 为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基；具体地，每个和每个上的一个或多个H可独立地被F、Cl、Br、或I取代。Each Each The number of carbon atoms independently selected from substituted or unsubstituted is a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings; specifically, each and each One or more H on R can be independently replaced by F, Cl, Br, or I.
进一步地，每个每个独立地选自以下结构式中的任意一种：

，其中，Z1、Z2独立地选自CH2、NH、O或S。Furthermore, each Each Independently selected from any one of the following structural formulas:

, wherein Z 1 and Z 2 are independently selected from CH 2 , NH, O or S.
优选地，每个每个独立地选自以下结构式中的任意一种：
Preferably, each Each Independently selected from any one of the following structural formulas:
A1为O原子时，R1和R2优选具有1～7个碳原子的烷基，特别优选具有2～5个碳原子的烷基。进一步地，A2为单键或O原子时，R2优选表示烷基，烯基或炔基，特别优选具有1～7个碳原子的烷基。在R1和R2中碳原子总和优选为4、5、6、7、8、9，或10，特别优选为5、6、7、8，或9。When A1 is an O atom, R1 and R2 are preferably alkyl groups having 1 to 7 carbon atoms, and particularly preferably alkyl groups having 2 to 5 carbon atoms. Further, when A2 is a single bond or an O atom, R2 is preferably an alkyl group, an alkenyl group or an alkynyl group, and particularly preferably an alkyl group having 1 to 7 carbon atoms. The total number of carbon atoms in R1 and R2 is preferably 4, 5, 6, 7, 8, 9, or 10, and particularly preferably 5, 6, 7, 8, or 9.
A1为单键时，R1和R2优选具有1～7个碳原子的烷基，特别优选2～5个碳原子。进一步地，A2为单键或O时，R2优选表示烷基，烯基或炔基，特别优选具有1-7个碳原子的烷基。在R1和R2中碳原子总和优选为4、5、6、7、8、9，或10，特别优选为5、6、7、8，或9。When A1 is a single bond, R1 and R2 are preferably alkyl groups having 1 to 7 carbon atoms, particularly preferably 2 to 5 carbon atoms. Further, when A2 is a single bond or O, R2 is preferably an alkyl group, an alkenyl group or an alkynyl group, particularly preferably an alkyl group having 1 to 7 carbon atoms. The total number of carbon atoms in R1 and R2 is preferably 4, 5, 6, 7, 8, 9, or 10, particularly preferably 5, 6, 7, 8, or 9.
在式(Ⅰ)中，R1和R2独立地表示烷基时，烷基可以是直链的，也可以是支链的。R1和R2优选为直链，且独立地具有1～7个碳原子，即优选为甲基、乙基、丙基、丁基、戊基、己基或庚基。In formula (I), when R1 and R2 independently represent an alkyl group, the alkyl group may be straight-chain or branched. R1 and R2 are preferably straight-chain and independently have 1 to 7 carbon atoms, i.e., preferably methyl, ethyl, propyl, butyl, pentyl, hexyl or heptyl.
在式(Ⅰ)中，R1和R2独立地表示具有2～15个碳原子的烯基或具有2～15个碳原子的炔基时，该烯基和炔基可以是直链的，也可以是支链的。R1和R2优选为具有2～7个碳原子的烯基或具有2～7个碳原子的炔基。In formula (I), when R1 and R2 independently represent an alkenyl group having 2 to 15 carbon atoms or an alkynyl group having 2 to 15 carbon atoms, the alkenyl group and the alkynyl group may be straight-chain or branched. R1 and R2 are preferably alkenyl groups having 2 to 7 carbon atoms or alkynyl groups having 2 to 7 carbon atoms.
具体地，R1和R2独立地选自乙烯基、丙-1-烯基、丙-2-烯基、丁-1-烯基、丁-2-烯基、丁-3-烯基、戊-1-烯基、戊-2-烯基、戊-3-烯基、戊-4-烯基、己-1-烯基、己-2-烯基、己-3-烯基、己-4-烯基、己-5-烯基、庚-1-烯基、庚-2-烯基、庚-3-烯基、庚-4-烯基、庚-5-烯基、庚-6-烯基、乙炔基、丙-1-炔基、丙-2-炔基、丁-1-炔基、丁-2-炔基、丁-3-炔基、戊-1-炔基、戊-2-炔基、戊-3-炔基、戊-4-炔基、己-1-炔基、己-2-炔基、己-3-炔基、己-4-炔基、己-5-炔基、庚-1-炔基、庚-2-炔基、庚-3-炔基、庚-4-炔基、庚-5-炔基或庚-6-炔基，且烯基可以是E和Z型异构体。烯基和炔基中，优选丙-2-烯基、丁-2-烯基、丁-3-烯基、戊-2-烯 基、戊-3-烯基、戊-4-烯基、丙-2-炔基、丁-2-炔基、丁-3-炔基、戊-2-炔基、戊-3-炔基或戊-4-炔基。Specifically, R1 and R2 are independently selected from vinyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, ethynyl, The alkene groups are prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, hept-1-ynyl, hept-2-ynyl, hept-3-ynyl, hept-4-ynyl, hept-5-ynyl or hept-6-ynyl, and the alkenyl group may be an E and Z isomer. Among the alkenyl and alkynyl groups, prop-2-enyl, but-2-enyl, but-3-enyl, pent-2-enyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, hept-1-ynyl, hept-2-ynyl, hept-3-ynyl, hept-4-ynyl, hept-5-ynyl or hept-6-ynyl are preferred. The invention further comprises the following: 1. a pent-4-enyl group, 2. a pent-3-enyl group, 3. a pent-4-enyl group, 4. a pent-5-enyl group, 5. a pent-6-enyl group, 6. a pent-7-enyl group, 7. a pent-8-enyl group, 8. a pent-9-enyl group, 9. a pent-10-enyl group, 9
在本发明的实施例中，所述第一化合物优选为式Ⅰ-1至式Ⅰ-4所示的至少一种： In an embodiment of the present invention, the first compound is preferably at least one of Formula I-1 to Formula I-4:
其中，Alkyl选自具有1-15个碳原子的烷基、具有2-15个碳原子的烯基，或具有2-15个碳原子的炔基。可选地，Alkyl基团中的一个或两个CH2基团可独立地被-O-、-CO-、-OC(O)-、-OCF2-、-CH2O或-OCH2-取代并使杂原子不直接键接。Alkyl为烷基时，烷基优选为具有1～7个碳原子的直链。Wherein, Alkyl is selected from an alkyl group having 1-15 carbon atoms, an alkenyl group having 2-15 carbon atoms, or an alkynyl group having 2-15 carbon atoms. Optionally, one or two CH2 groups in the Alkyl group can be independently substituted by -O-, -CO-, -OC(O)-, -OCF2-, -CH2O or -OCH2- and the heteroatom is not directly bonded. When Alkyl is an alkyl group, the alkyl group is preferably a straight chain having 1 to 7 carbon atoms.
所述第一化合物优选为A1和A2为单键或O的化合物，优选为如式Ⅰ-1-1至Ⅰ-1-9、Ⅰ-3-1至Ⅰ-3-27所示的结构中的至少一种：


The first compound is preferably a compound in which A1 and A2 are single bonds or O, and is preferably at least one of the structures shown in Formulas Ⅰ-1-1 to Ⅰ-1-9, Ⅰ-3-1 to Ⅰ-3-27:


上述任一实施例提及的第一化合物Ⅰ本身及其基团、取代基具有不对称中心或手性中心，能以异构体的形式存在，如纯对映体、非对映体、E或Z异构体或作为以任何所需比例的多个异构体的混合物存在，例如作为外消旋体、E/Z异构体混合物。The first compound I mentioned in any of the above embodiments itself and its groups and substituents have asymmetric centers or chiral centers and can exist in the form of isomers, such as pure enantiomers, diastereomers, E or Z isomers, or as a mixture of multiple isomers in any desired proportion, for example, as a racemate, E/Z isomer mixture.
本发明实施例的第一化合物Ⅰ为含氟苯并呋喃类液晶化合物，该类化合物具有较高的负介电各向异性、良好的液晶互溶性、相对低的旋转粘度等，应用显示器件中，可减少响应时间、提高对比度。The first compound I of the embodiment of the present invention is a fluorinated benzofuran liquid crystal compound, which has high negative dielectric anisotropy, good liquid crystal mutual solubility, relatively low rotational viscosity, etc. When used in display devices, it can reduce the response time and improve the contrast.
当m为0，n为1时，所述第一化合物的合成路径如下：
When m is 0 and n is 1, the synthesis path of the first compound is as follows:
以为原料，经过上述一系列反 应得到 by As raw materials, after a series of reactions Deserve
当m为0，n为2时，可将原料替换为之后参照上述合成路线得到其中，与前述所选基团范围相同，即独立地选自取代或未取代的碳原子数为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基。When m is 0 and n is 2, the raw material Replace with Then refer to the above synthetic route to obtain in, With the aforementioned The selected groups have the same range, i.e. The group is independently selected from a substituted or unsubstituted heteroatom having 3 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings.
进一步地，选自以下结构式中的任意一种：

，其中，Z1、Z2独立地选自CH2、NH、O或S。further, Select any one of the following structural formulas:

, wherein Z 1 and Z 2 are independently selected from CH 2 , NH, O or S.
优选地，选自以下结构式中的任意一种：

的具体的基团选择可与相同或不同。的合成路线如下：
Preferably, Select any one of the following structural formulas:

The specific group selection can be Same or different. The synthetic route is as follows:
当m、n为其他情况时，第一化合物的合成路线与上述实施例的合成路线相同或类似。When m and n are other conditions, the synthesis route of the first compound is the same as or similar to the synthesis route of the above embodiment.
所述第二化合物的结构式如下式Ⅱ1至Ⅱ9所示：
The structural formula of the second compound is shown in the following formula II1 to II9:
其中，R3、R4独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基、取代或未被取代的碳原子数为2～10的炔氧基。具体地，R3、R4中的至少一个H可独立地被F、Cl、Br，或I取代。Wherein, R 3 and R 4 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms. Specifically, at least one H in R 3 and R 4 may be independently substituted by F, Cl, Br, or I.
所述第三化合物如下式Ⅲ1至Ⅲ5所示：
The third compound is shown in the following formula III1 to III5:
其中，R5、R6独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基、取代或未被取代的碳原子数为2～10的炔氧基。具体地，R5、R6中的至少一个H可独立地被F、Cl、Br，或I取代。Wherein, R 5 and R 6 are independently selected from substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkenyloxy having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyloxy having 2 to 10 carbon atoms. Specifically, at least one H in R 5 and R 6 may be independently substituted by F, Cl, Br, or I.
进一步地，相对于所述液晶组合物的重量，所述液晶组合物的包括以下重量百分比的组分：1％～50％的式I所示的第一化合物；1％～90％的式Ⅱ1至Ⅱ9所示的第二化合物；1％～90％的式Ⅲ1至Ⅲ5所示的化合物。Furthermore, relative to the weight of the liquid crystal composition, the liquid crystal composition includes the following components in weight percentage: 1% to 50% of the first compound shown in formula I; 1% to 90% of the second compound shown in formulas II1 to II9; and 1% to 90% of the compounds shown in formulas III1 to III5.
所述液晶组合物除了含有上述第一化合物、第二化合物以及第三化合物以外，上述液晶组合物在应用到显示器件上时，还可包含其他功能性的材料，如手性剂、引发剂、阻聚剂、有机溶剂以及其他助剂等In addition to the first compound, the second compound and the third compound, the liquid crystal composition may also contain other functional materials, such as chiral agents, initiators, inhibitors, organic solvents and other additives, when applied to a display device.
优选地，本发明实施例的液晶组合物中包含以下重量百分比的组分：1％～40％的式I所示的第一化合物；5％～70％的式Ⅱ1至Ⅱ9所示的第二化合物；Preferably, the liquid crystal composition of the embodiment of the present invention comprises the following components in weight percentage: 1% to 40% of the first compound represented by formula I; 5% to 70% of the second compound represented by formula II1 to II9;
5％～70％的式Ⅲ1至Ⅲ5所示的化合物。 5% to 70% of the compounds represented by formula III1 to III5.
特别优选地，所述液晶组合物中包含以下重量百分比的组分：1％～25％的式I所示的第一化合物；10％～50％的式Ⅱ1至Ⅱ9所示的第二化合物；Particularly preferably, the liquid crystal composition comprises the following components in weight percentage: 1% to 25% of the first compound represented by formula I; 10% to 50% of the second compound represented by formula II1 to II9;
10％～50％的式Ⅲ1至Ⅲ5所示的化合物。10% to 50% of the compounds represented by formula III1 to III5.
所述液晶组合物的制备可采用热溶解方法来制得，包括以下步骤：The preparation of the liquid crystal composition can be prepared by a thermal dissolution method, comprising the following steps:
S10、用天平按质量百分比称量液晶化合物(第一化合物、第二化合物、第三化合物)，其中称量加入顺序无特定要求，通常以液晶化合物的熔点由低到高的顺序一次称量混合；S20、在60～100℃下加热并搅拌，使各组分充分溶解混合；S30、冷却至室温，封装得到目标样品。S10. Weigh the liquid crystal compounds (the first compound, the second compound, and the third compound) by mass percentage using a balance. There is no specific requirement for the order of weighing and adding. Usually, the liquid crystal compounds are weighed and mixed in order of their melting points from low to high. S20. Heat and stir at 60 to 100° C. to fully dissolve and mix the components. S30. Cool to room temperature and package to obtain the target sample.
除非另有说明，温度单位为℃；Tni代表液晶组合物的清亮点(单位：℃)；Δn代表25℃时的光学各向异性，ne为非寻常光的折射率；γ1代表25℃时的旋转粘度(单位：mPa·s)；Δε代表25℃时的介电各向异性，ε⊥为垂直于液晶分子长轴的介电常数。Unless otherwise specified, the temperature unit is °C; Tni represents the clearing point of the liquid crystal composition (unit: °C); Δn represents the optical anisotropy at 25 °C, ne is the refractive index of extraordinary light; γ1 represents the rotational viscosity at 25 °C (unit: mPa·s); Δε represents the dielectric anisotropy at 25 °C, ε⊥ is the dielectric constant perpendicular to the long axis of the liquid crystal molecules.
发明人对制得的液晶组合物进行了混晶实验，具体如下表1～表6所示。按照本领域常规的检测方法，得到本发明实施例的液晶组合物的各项性能参数，其中，表中各性能参数的具体含义如下：温度单位为℃；Tni代表液晶组合物的清亮点(单位：℃)；Δn代表25℃时的光学各向异性，ne为非寻常光的折射率；γ1代表25℃时的旋转粘度(单位：mPa·s)；Δε代表25℃时的介电各向异性，ε⊥为垂直于液晶分子长轴的介电常数；K11为展曲弹性系数，K33为弯曲弹性系数。The inventors conducted mixed crystal experiments on the prepared liquid crystal composition, as shown in Tables 1 to 6. According to the conventional detection method in the art, the performance parameters of the liquid crystal composition of the embodiment of the present invention were obtained, wherein the specific meanings of the performance parameters in the table are as follows: the temperature unit is ℃; Tni represents the clearing point of the liquid crystal composition (unit: ℃); Δn represents the optical anisotropy at 25℃, ne is the refractive index of extraordinary light; γ1 represents the rotational viscosity at 25℃ (unit: mPa·s); Δε represents the dielectric anisotropy at 25℃, ε⊥ is the dielectric constant perpendicular to the long axis of the liquid crystal molecule; K11 is the splay elastic coefficient, and K33 is the bending elastic coefficient.
表1实施例1的液晶组合物的组分分配及其性能参数
Table 1 Component distribution and performance parameters of the liquid crystal composition of Example 1
表2实施例2的液晶组合物的组分分配及其性能参数
Table 2 Component distribution and performance parameters of the liquid crystal composition of Example 2
表3实施例3的液晶组合物的组分分配及其性能参数
Table 3 Component distribution and performance parameters of the liquid crystal composition of Example 3
表4实施例4的液晶组合物的组分分配及其性能参数
Table 4 Component distribution and performance parameters of the liquid crystal composition of Example 4
表5实施例5的液晶组合物的组分分配及其性能参数
Table 5 Component distribution and performance parameters of the liquid crystal composition of Example 5
表6实施例6的液晶组合物的组分分配及其性能参数
Table 6 Component distribution and performance parameters of the liquid crystal composition of Example 6
液晶的对比度与液晶的介电各向异性有关，液晶具有介电负性时，可提高对比度，由上述测得数据可知，本发明实施例的液晶组合物的介电各向异性Δε处于-3.8～-3.5之间，具有较高的介电负性，因此可提高液晶组合物的对比度。The contrast of liquid crystal is related to the dielectric anisotropy of the liquid crystal. When the liquid crystal has dielectric negativity, the contrast can be improved. From the above measured data, it can be seen that the dielectric anisotropy Δε of the liquid crystal composition of the embodiment of the present invention is between -3.8 and -3.5, and has a relatively high dielectric negativity, so the contrast of the liquid crystal composition can be improved.
液晶的响应时间与旋转粘度γ1呈正相关，与介电各向异性Δε、以及展曲弹性系数K11呈负相关；本发明实施例提供的液晶组合物中，第一化合物具有较高的介电负性，可以提高液晶的介电负性，降低响应时间；第二化合物具有介电中性、低粘度，可以降低液晶的粘度，降低响应时间；第三化合物具有介电负性，可根据需求调节Δn、Tni以及粘度，整体上调节液晶性质。从上述测得数据可知，本发明实施例提供的液晶组合物的旋转粘度γ1处于77～98mPa·s，具有低旋转粘度，可减少响应时间；K11处于14.1～14.7，具有较高的展曲弹性系数，可减少响应时间；介电各向异性Δε处于-3.8～-3.5之间， 具有较高的介电负性，可降低响应时间；且所述液晶组合物的清亮点Tni处于85℃以上，具有较高的清亮点，可在宽温度范围内具有理想的液晶相。The response time of the liquid crystal is positively correlated with the rotational viscosity γ1, and negatively correlated with the dielectric anisotropy Δε and the splay elastic coefficient K11 ; in the liquid crystal composition provided in the embodiment of the present invention, the first compound has a higher dielectric negativity, which can improve the dielectric negativity of the liquid crystal and reduce the response time; the second compound has dielectric neutrality and low viscosity, which can reduce the viscosity of the liquid crystal and reduce the response time; the third compound has dielectric negativity, and Δn, Tni and viscosity can be adjusted according to needs to adjust the liquid crystal properties as a whole. From the above measured data, it can be seen that the rotational viscosity γ1 of the liquid crystal composition provided in the embodiment of the present invention is between 77 and 98 mPa·s, with low rotational viscosity, which can reduce the response time; K11 is between 14.1 and 14.7, with a higher splay elastic coefficient, which can reduce the response time; the dielectric anisotropy Δε is between -3.8 and -3.5, The liquid crystal composition has a high dielectric negativity and can reduce the response time; and the clearing point Tni of the liquid crystal composition is above 85°C, has a high clearing point, and can have an ideal liquid crystal phase in a wide temperature range.
基于上述实施例，如图1所示，本发明实施例还提供一种显示面板100，包括相对设置的阵列基板10和彩膜基板30，以及夹设于阵列基板10和彩膜基板30之间的液晶层20，所述液晶层20的材料包括上述实施例的液晶组合物。上述液晶组合物应用到显示面板中，能够降低显示面板的响应时间，提高显示面板的对比度。Based on the above embodiment, as shown in FIG1 , the embodiment of the present invention further provides a display panel 100, comprising an array substrate 10 and a color filter substrate 30 arranged opposite to each other, and a liquid crystal layer 20 sandwiched between the array substrate 10 and the color filter substrate 30, wherein the material of the liquid crystal layer 20 comprises the liquid crystal composition of the above embodiment. The above liquid crystal composition is applied to the display panel, which can reduce the response time of the display panel and improve the contrast of the display panel.
所述显示面板100的阵列基板10包括薄膜晶体管阵列，所述薄膜晶体管阵列用以驱动液晶层发光。所述显示面板100还包括设置于阵列基板10背离液晶层20一侧的背光模组，所述背光模组用于为液晶层20提供背光源。The array substrate 10 of the display panel 100 includes a thin film transistor array, which is used to drive the liquid crystal layer to emit light. The display panel 100 also includes a backlight module disposed on the side of the array substrate 10 away from the liquid crystal layer 20, which is used to provide a backlight source for the liquid crystal layer 20.
所述液晶组合物可应用于手表、手机、电视和电脑等显示器中，对于VA、ECB、PALC、FFS或IPS等类型的显示器均适用。The liquid crystal composition can be applied to displays such as watches, mobile phones, televisions and computers, and is applicable to displays of types such as VA, ECB, PALC, FFS or IPS.
在上述实施例中，对各个实施例的描述都各有侧重，某个实施例中没有详述的部分，可以参见其他实施例的相关描述。In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.
可以理解的是，对本领域普通技术人员来说，可以根据本申请的技术方案及其发明构思加以等同替换或改变，而所有这些改变或替换都应属于本申请所附的权利要求的保护范围。 It is understandable that those skilled in the art can make equivalent substitutions or changes based on the technical solution and inventive concept of the present application, and all these changes or substitutions should fall within the protection scope of the claims attached to the present application.

Claims (20)

  1. 一种液晶组合物，其中，包括第一化合物，所述第一化合物的结构式如式Ⅰ所示： A liquid crystal composition, comprising a first compound, wherein the structural formula of the first compound is as shown in Formula I:
    其中，A1、A2独立地选自单键、O、S、具有1～7个碳原子的亚烷基，或具有1～7个碳原子的亚烷氧基；wherein A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
    K1、K2独立地选自H或F，且不同时为H；K 1 and K 2 are independently selected from H or F, and are not H at the same time;
    m、n独立地选自0～2中的整数，且不同时为0；m and n are independently selected from integers between 0 and 2, and are not both 0;
    每个每个独立地选自取代或未取代的碳原子数为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基；Each Each independently selected from a substituted or unsubstituted heteroatom having 3 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings;
    R1、R2独立地选自H、F、Cl、Br、I、CN、SCN、NCS、SF5、取代或未取代的碳原子数为1～15个碳原子的烷基、取代或未取代的碳原子数为2～15的烯基，或取代或未取代的碳原子数为2～15的炔基，其中，R1、R2为烷基、烯基或炔基时，R1、R2中的至少一个CH2独立地被-O-、-S-、-SO2-、-CO-、-C(O)O-、-OC(O)O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CF2CHF-、-CF2CH2-、-CHF-CHF-、-CHF-CH2-、-CH2O、-CF＝CH-、-CF＝CF-、-CH＝CH-或-C≡C-取代并使杂原子不直接键接，和/或R1、R2的末端基团独立地被CN或CF3取代。R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH 2 O, -CF=CH-, -CF=CF-, -CH=CH- or -C≡C- and the hetero atom is not directly bonded, and/or the terminal groups of R 1 and R 2 are independently substituted by CN or CF 3 .
  2. 根据权利要求1所述的液晶组合物，其中，m、n独立地选自0或1， 且不同时为0。The liquid crystal composition according to claim 1, wherein m and n are independently selected from 0 or 1, And they are not 0 at the same time.
  3. 根据权利要求1所述的液晶组合物，其中，每个每个独立地选自以下结构式中的任意一种：
    The liquid crystal composition according to claim 1, wherein each Each Independently selected from any one of the following structural formulas:
    其中，Z1、Z2独立地选自CH2、NH、O或S。Wherein, Z 1 and Z 2 are independently selected from CH 2 , NH, O or S.
  4. 根据权利要求3所述的液晶组合物，其中，每个每个独立地选自以下结构式中的任意一种：
    The liquid crystal composition according to claim 3, wherein each Each Independently selected from any one of the following structural formulas:
  5. 根据权利要求1所述的液晶组合物，其中，R1、R2独立地选自取代或未取代的碳原子数为1～7的烷基、取代或未取代的碳原子数为1～7的烯基，或 取代或未取代的碳原子数为1～7的炔基，其中，R1、R2中的一个或两个CH2独立地被-O-、-CO、-C(O)O-、-OC(O)-、-CF2O-、-OCF2-、-CH2O或-OCH2-取代并使杂原子不直接键接。The liquid crystal composition according to claim 1, wherein R 1 and R 2 are independently selected from substituted or unsubstituted alkyl groups having 1 to 7 carbon atoms, substituted or unsubstituted alkenyl groups having 1 to 7 carbon atoms, or A substituted or unsubstituted alkynyl group having 1 to 7 carbon atoms, wherein one or both CH2 of R1 and R2 are independently substituted by -O-, -CO, -C(O)O-, -OC(O)-, -CF2O- , -OCF2- , -CH2O or -OCH2- and the heteroatom is not directly bonded.
  6. 根据权利要求1所述的液晶组合物，其中，所述第一化合物选自如下式Ⅰ-1至式Ⅰ-4所示的至少一种：The liquid crystal composition according to claim 1, wherein the first compound is selected from at least one of the following formulas I-1 to I-4:
    其中，Alkyl独立地选自至少一个碳原子被-O-、-CO-、-OC(O)-、-OCF2-或-OCH2-取代并使杂原子不直接键接的烷基，至少一个碳原子被-O-、-CO-、-C(O)O-、-CF2O-或-CH2O取代并使杂原子不直接键接的烯基，或至少一个碳原子被-O-、-CO-、-C(O)O-、-CF2O-或-CH2O取代并使杂原子不直接键接的炔基，其中，烷基的碳原子数为1～15，烯基的碳原子数为2～15，炔基的碳原子数为2～15。 Wherein, Alkyl is independently selected from an alkyl group in which at least one carbon atom is substituted by -O-, -CO-, -OC(O)-, -OCF 2 - or -OCH 2 - and a heteroatom is not directly bonded thereto, an alkenyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF 2 O- or -CH 2 O and a heteroatom is not directly bonded thereto, or an alkynyl group in which at least one carbon atom is substituted by -O-, -CO-, -C(O)O-, -CF 2 O- or -CH 2 O and a heteroatom is not directly bonded thereto, wherein the alkyl group has 1 to 15 carbon atoms, the alkenyl group has 2 to 15 carbon atoms, and the alkynyl group has 2 to 15 carbon atoms.
  7. 根据权利要求1所述的液晶组合物，其中，所述第一化合物选自如下式Ⅰ-1-1至Ⅰ-1-9、Ⅰ-3-1至Ⅰ-3-27所示的至少一种：


    The liquid crystal composition according to claim 1, wherein the first compound is selected from at least one of the following formulas Ⅰ-1-1 to Ⅰ-1-9 and Ⅰ-3-1 to Ⅰ-3-27:


  8. 根据权利要求1所述的液晶组合物，其中，所述液晶组合物还包括第二化合物，所述第二化合物如式Ⅱ1至Ⅱ9所示：The liquid crystal composition according to claim 1, wherein the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
    R3、R4独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
  9. 根据权利要求8所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～90％的式Ⅱ1至Ⅱ9所示的第二化合物。The liquid crystal composition according to claim 8, wherein the liquid crystal composition comprises 1% to 90% of the second compound represented by formula II1 to II9 relative to the weight of the liquid crystal composition.
  10. 根据权利要求9所述的液晶组合物，其中，相对于所述液晶组合物的 重量，所述液晶组合物的包括5％～70％的式Ⅱ1至Ⅱ9所示的第二化合物。The liquid crystal composition according to claim 9, wherein relative to the liquid crystal composition By weight, the liquid crystal composition comprises 5% to 70% of the second compound represented by formula II1 to II9.
  11. 根据权利要求10所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括10％～50％的式Ⅱ1至Ⅱ9所示的第二化合物。The liquid crystal composition according to claim 10, wherein the liquid crystal composition comprises 10% to 50% of the second compound represented by formula II1 to II9 relative to the weight of the liquid crystal composition.
  12. 根据权利要求1所述的液晶组合物，其中，所述液晶组合物还包括第三化合物，所述第三化合物如式Ⅲ1至Ⅲ5所示：The liquid crystal composition according to claim 1, wherein the liquid crystal composition further comprises a third compound, and the third compound is represented by formula III1 to III5:
    其中，R5、R6独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 Wherein, R 5 and R 6 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
  13. 根据权利要求12所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～90％的式Ⅲ1至Ⅲ5所示的化合物。The liquid crystal composition according to claim 12, wherein the liquid crystal composition comprises 1% to 90% of the compounds represented by formulas III1 to III5 relative to the weight of the liquid crystal composition.
  14. 根据权利要求13所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括5％～70％的式Ⅲ1至Ⅲ5所示的化合物。The liquid crystal composition according to claim 13, wherein the liquid crystal composition comprises 5% to 70% of the compounds represented by formulas III1 to III5 relative to the weight of the liquid crystal composition.
  15. 根据权利要求14所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括10％～50％的式Ⅲ1至Ⅲ5所示的化合物。 The liquid crystal composition according to claim 14, wherein the liquid crystal composition comprises 10% to 50% of the compounds represented by formulas III1 to III5 relative to the weight of the liquid crystal composition.
  16. 根据权利要求1所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～50％的式I所示的第一化合物。The liquid crystal composition according to claim 1, wherein the liquid crystal composition comprises 1% to 50% of the first compound represented by formula I relative to the weight of the liquid crystal composition.
  17. 根据权利要求16所述的液晶组合物，其中，相对于所述液晶组合物的重量，所述液晶组合物的包括1％～25％的式I所示的第一化合物。The liquid crystal composition according to claim 16, wherein the liquid crystal composition comprises 1% to 25% of the first compound represented by formula I relative to the weight of the liquid crystal composition.
  18. 一种显示面板，其中，包括相对设置的阵列基板和彩膜基板，以及夹设于所述阵列基板和所述彩膜基板之间的液晶层，所述液晶层的材料包括液晶组合物，所述液晶组合物包括第一化合物，所述第一化合物的结构式如式Ⅰ所示： A display panel, comprising an array substrate and a color film substrate arranged opposite to each other, and a liquid crystal layer sandwiched between the array substrate and the color film substrate, wherein the material of the liquid crystal layer comprises a liquid crystal composition, and the liquid crystal composition comprises a first compound, and the structural formula of the first compound is shown in Formula I:
    其中，A1、A2独立地选自单键、O、S、具有1～7个碳原子的亚烷基，或具有1～7个碳原子的亚烷氧基；wherein A 1 and A 2 are independently selected from a single bond, O, S, an alkylene group having 1 to 7 carbon atoms, or an alkyleneoxy group having 1 to 7 carbon atoms;
    K1、K2独立地选自H或F，且不同时为H；K 1 and K 2 are independently selected from H or F, and are not H at the same time;
    m、n独立地选自0～2中的整数，且不同时为0；m and n are independently selected from integers between 0 and 2, and are not both 0;
    每个每个独立地选自取代或未取代的碳原子数为3～5的杂环原子、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为3～10的环烯基、取代或未取代的环数为1或2的杂芳香基，或取代或未取代的环数为1或2的芳香基；Each Each independently selected from a substituted or unsubstituted heteroatom having 3 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkenyl having 3 to 10 carbon atoms, a substituted or unsubstituted heteroaromatic group having 1 or 2 rings, or a substituted or unsubstituted aromatic group having 1 or 2 rings;
    R1、R2独立地选自H、F、Cl、Br、I、CN、SCN、NCS、SF5、取代或未取代的碳原子数为1～15个碳原子的烷基、取代或未取代的碳原子数为2～15的烯基，或取代或未取代的碳原子数为2～15的炔基，其中，R1、R2为烷基、烯基或炔基时，R1、R2中的至少一个CH2独立地被-O-、-S-、-SO2-、-CO-、-C(O)O-、-OC(O)O-、-OCF2-、-CH2CH2-、-CF2CF2-、-CF2CHF-、-CF2CH2-、-CHF-CHF-、-CHF-CH2-、-CH2O、-CF＝CH-、-CF＝CF-、-CH＝CH-或-C≡C- 取代并使杂原子不直接键接，和/或R1、R2的末端基团独立地被CN或CF3取代。R 1 and R 2 are independently selected from H, F, Cl, Br, I, CN, SCN, NCS, SF 5 , substituted or unsubstituted alkyl having 1 to 15 carbon atoms, substituted or unsubstituted alkenyl having 2 to 15 carbon atoms, or substituted or unsubstituted alkynyl having 2 to 15 carbon atoms, wherein when R 1 and R 2 are alkyl, alkenyl or alkynyl, at least one CH 2 in R 1 and R 2 is independently replaced by -O-, -S-, -SO 2 -, -CO-, -C(O)O-, -OC(O)O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 CF 2 -, -CF 2 CHF-, -CF 2 CH 2 -, -CHF-CHF-, -CHF-CH 2 -, -CH 2 O, -CF＝CH-, -CF＝CF-, -CH＝CH-, or -C≡C- The heteroatom is not directly bonded to the substitution, and/or the terminal groups of R 1 and R 2 are independently substituted by CN or CF 3 .
  19. 根据权利要求18所述的液晶组合物，其中，所述液晶组合物还包括第二化合物，所述第二化合物如式Ⅱ1至Ⅱ9所示：The liquid crystal composition according to claim 18, wherein the liquid crystal composition further comprises a second compound, and the second compound is as shown in Formula II1 to II9:
    R3、R4独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
  20. 根据权利要求18所述的液晶组合物，其中，所述液晶组合物还包括第三化合物，所述第三化合物如式Ⅲ1至Ⅲ5所示： The liquid crystal composition according to claim 18, wherein the liquid crystal composition further comprises a third compound, and the third compound is represented by formula III1 to III5:
    其中，R5、R6独立地选自取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未被取代的碳原子数为2～10的烯基、取代或未被取代的碳原子数为2～10的烯氧基、取代或未被取代的碳原子数为2～10的炔基，或取代或未被取代的碳原子数为2～10的炔氧基。 Wherein, R 5 and R 6 are independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenyloxy group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted alkynyloxy group having 2 to 10 carbon atoms.
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Publication number Priority date Publication date Assignee Title
CN109370613A (en) * 2018-12-24 2019-02-22 西安瑞立电子材料有限公司 Liquid-crystal composition and its application
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CN114105921A (en) * 2021-12-22 2022-03-01 北京云基科技有限公司 Cyclopentyl benzofuran liquid crystal compound and application thereof
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Family Cites Families (6)

* Cited by examiner, † Cited by third party
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Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109370613A (en) * 2018-12-24 2019-02-22 西安瑞立电子材料有限公司 Liquid-crystal composition and its application
CN113845922A (en) * 2020-06-28 2021-12-28 江苏和成显示科技有限公司 Liquid crystal composition containing dibenzo derivative and liquid crystal display device
CN114105921A (en) * 2021-12-22 2022-03-01 北京云基科技有限公司 Cyclopentyl benzofuran liquid crystal compound and application thereof
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