CN103525433A - Liquid crystal composition containing difluoromethylene aether group compounds - Google Patents

Liquid crystal composition containing difluoromethylene aether group compounds Download PDF

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CN103525433A
CN103525433A CN201310442001.7A CN201310442001A CN103525433A CN 103525433 A CN103525433 A CN 103525433A CN 201310442001 A CN201310442001 A CN 201310442001A CN 103525433 A CN103525433 A CN 103525433A
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CN103525433B (en
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华瑞茂
夏治国
孟劲松
温刚
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Chengzhi Yonghua Technology Co.,Ltd.
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

本发明公开了一种含二氟亚甲基醚基化合物的液晶组合物,包括由通式I和通式II所示的介电正性化合物组成的组分A、由一种或多种通式III所示的化合物组成的组分B、由一种或多种通式IV所示的化合物组成的组分C;本发明提供的液晶组合物性能优异,具有较宽向列相温度范围,适当的正介电各向异性,合适的光学各向异性,很高的电荷保持率,响应速度快,旋转粘度低,消耗功率低等特点。本发明的组合物可应用在液晶显示中,特别适用于快速响应的有源矩阵TN-TFT、IPS-TFT显示器。各通式中各参数具有说明书中给出的含义, The invention discloses a liquid crystal composition containing a difluoromethylene ether group compound, which comprises a component A consisting of dielectrically positive compounds represented by general formula I and general formula II, and composed of one or more general formulas Component B composed of compounds represented by formula III, component C composed of one or more compounds represented by general formula IV; the liquid crystal composition provided by the present invention has excellent performance and has a wide nematic phase temperature range, Appropriate positive dielectric anisotropy, appropriate optical anisotropy, high charge retention, fast response, low rotational viscosity, and low power consumption. The composition of the invention can be applied in liquid crystal displays, and is especially suitable for fast-response active matrix TN-TFT and IPS-TFT displays. Each parameter in each general formula has the implication given in the description,

Description

含二氟亚甲基醚基化合物的液晶组合物Liquid crystal composition containing difluoromethylene ether compound

技术领域technical field

本发明属于液晶化合物领域,具体涉及一种应用在液晶显示中的含有介电正性液晶化合物的液晶组合物。The invention belongs to the field of liquid crystal compounds, and in particular relates to a liquid crystal composition containing dielectrically positive liquid crystal compounds used in liquid crystal displays.

背景技术Background technique

液晶显示元件根据显示方式分为下列模式:扭曲向列相(TN)模式、超扭曲向列相(STN)模式、共面模式(IPS)、垂直配向(VA)模式。无论何种显示模式均需要液晶组合物有以下特性:化学、物理性质稳定;粘度低;具有合适的Δε;合适的拆射率Δn;与其他液晶化合物的相溶性好。Liquid crystal display elements are divided into the following modes according to the display mode: twisted nematic (TN) mode, super twisted nematic (STN) mode, in-plane mode (IPS), and vertical alignment (VA) mode. Regardless of the display mode, the liquid crystal composition needs to have the following characteristics: stable chemical and physical properties; low viscosity; suitable Δε; suitable refraction rate Δn; good compatibility with other liquid crystal compounds.

作为液晶材料,需要具有良好的化学和热稳定性以及对电场和电磁辐射的稳定性。而作为薄膜晶体管技术(TFT-LCD)用液晶材料,不仅需要具有如上稳定性外,还应具有较宽的向列相温度范围、合适的双折射率各向异性、非常高的电阻率、良好的抗紫外线性能、高电荷保持率以及低蒸汽压等性能。As a liquid crystal material, it is required to have good chemical and thermal stability as well as stability to electric fields and electromagnetic radiation. As a liquid crystal material for thin film transistor technology (TFT-LCD), it not only needs to have the above stability, but also has a wide temperature range of nematic phase, suitable birefringence anisotropy, very high resistivity, good Excellent UV resistance, high charge retention and low vapor pressure.

对于薄膜晶体管技术(TFT-LCD)应用领域,近年来市场虽然已经非常巨大,技术也逐渐成熟,与此同时,由于液晶材料技术的不断进步,人们对显示技术的要求也在不断的提高,尤其是在实现快速响应,降低驱动电压以降低功耗等方面。For the application field of thin film transistor technology (TFT-LCD), although the market has been huge in recent years, the technology has gradually matured. It is in terms of achieving fast response, reducing driving voltage to reduce power consumption, etc.

液晶材料作为液晶显示器重要的光电子材料之一,对改善液晶显示器的性能发挥重要的作用。任何的显示用液晶组合物都要求有较宽的液晶态温度,较高的稳定性,比较适合的粘度,对电场有较快的响应速度。但是目前为止还没有任何单一的液晶材料单独用在液晶显示器中,而不用开发其它性能特性的组合物就能够满足性能要求。因此,不断开发新的性能优异的液晶材料对液晶显示发展具有重要的意义。As one of the important optoelectronic materials of liquid crystal display, liquid crystal material plays an important role in improving the performance of liquid crystal display. Any liquid crystal composition for display requires a wider liquid crystal state temperature, higher stability, more suitable viscosity, and faster response speed to electric field. But so far there is no single liquid crystal material used alone in liquid crystal displays that can meet the performance requirements without developing a composition with other performance characteristics. Therefore, continuous development of new liquid crystal materials with excellent performance is of great significance to the development of liquid crystal displays.

发明内容Contents of the invention

本发明需要解决的技术问题提供一种含有介电正性液晶化合物的液晶组合物,该液晶组合物具有大的正介电各向异性,低折射率各向异性,并且具有较高的清亮点,低旋转粘度,并且可以在高温区域维持高电荷保持率,在低温区域维持快的响应时间。The technical problem to be solved by the present invention is to provide a liquid crystal composition containing a dielectrically positive liquid crystal compound, which has large positive dielectric anisotropy, low refractive index anisotropy, and a relatively high clearing point , low rotational viscosity, and can maintain a high charge retention rate in the high temperature region, and maintain a fast response time in the low temperature region.

为解决上述技术问题,本发明所采取的技术方案是:In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is:

含二氟亚甲基醚基化合物的液晶组合物,包括由通式I和通式II所示的介电正性化合物组成的组分A、由一种或多种通式III所示的化合物组成的组分B、由一种或多种通式IV所示的化合物组成的组分C;A liquid crystal composition containing a difluoromethylene ether compound, comprising a component A consisting of dielectrically positive compounds represented by general formula I and general formula II, and one or more compounds represented by general formula III Component B composed of, component C composed of one or more compounds represented by general formula IV;

其中,in,

R1、R5分别为H或者C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任一基团;或者为C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任意H被F取代后的任一基团;R 1 and R 5 are respectively H or C 1 to C 10 straight chain alkyl, C 1 to C 10 straight chain alkoxy, C 2 to C 10 straight chain alkenyl, C 3 to C 8 straight chain alkenyloxy Any of the groups; or C 1 ~ C 10 straight chain alkyl, C 1 ~ C 10 straight chain alkoxy, C 2 ~ C 10 straight chain alkenyl, C 3 ~ C 8 straight chain alkenyloxy Any group after any H in is replaced by F;

R2、R3、R4、R6分别为下列①~④所述基团的其中任一种:R 2 , R 3 , R 4 , and R 6 are any of the groups described in the following ①~④ respectively:

①:H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5①: H, Cl, F, CN, OCN, OCF 3 , CF 3 , CHF 2 , CH 2 F, OCHF 2 , SCN, NCS, SF 5 ,

②:C1~C15直链烷基、C1~C15直链烷氧基、C2~C15直链烯基、C2~C15直链烯氧基,②: C 1 ~ C 15 straight chain alkyl, C 1 ~ C 15 straight chain alkoxy, C 2 ~ C 15 straight chain alkenyl, C 2 ~ C 15 straight chain alkenyloxy,

③:②中所述基团中的一个或多个-CH2-被-CH=CH-、-C≡C-、-COO-、-OOC-、亚环丁基、亚环戊基、-O-或-S-替代后且氧原子不直接相连的基团,③: One or more of -CH 2 - in the groups mentioned in ② is replaced by -CH=CH-, -C≡C-, -COO-, -OOC-, cyclobutylene, cyclopentylene, - O- or -S-substituted groups with oxygen atoms not directly connected,

④:②或者③中所述基团的任意H被F、Cl取代后的基团;④: A group in which any H of the group mentioned in ② or ③ is replaced by F or Cl;

(F)为H或F;(F) is H or F;

Z1、Z2、Z3分别为单键、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-、-CF=CF-中的一种;Z 1 , Z 2 , Z 3 are single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -CH=CH-, -C ≡C-, -COO-, -OOC-, -CF 2 O-, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 - , -C One of 2 F 4 -, -CF=CF-;

A1、A2、A3、A4、A5、A6、A7、A8、A9分别为

Figure BDA0000387402310000031
Figure BDA0000387402310000033
中的一种;A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 are respectively
Figure BDA0000387402310000031
Figure BDA0000387402310000033
one of

a、b、d、e、f、g、h分别为0或1或2或3;c为1或2,并且a+b+c≤5。a, b, d, e, f, g, h are 0 or 1 or 2 or 3 respectively; c is 1 or 2, and a+b+c≤5.

本发明的进一步改进在于:液晶组合物中组分A占液晶组合物的重量百分含量为1%~80%,组分B占液晶组合物的重量百分含量为1%~60%,组分C占液晶组合物的重量百分含量为1%~50%;The further improvement of the present invention is that: in the liquid crystal composition, component A accounts for 1% to 80% by weight of the liquid crystal composition, and component B accounts for 1% to 60% by weight of the liquid crystal composition. Component C accounts for 1% to 50% by weight of the liquid crystal composition;

本发明的进一步改进在于:所述通式I所示的化合物占液晶组合物的重量百分含量为1%~50%。The further improvement of the present invention is that: the compound represented by the general formula I accounts for 1%-50% by weight of the liquid crystal composition.

本发明的进一步改进在于:所述通式II所示的化合物占液晶组合物的重量百分含量为1%~50%。The further improvement of the present invention is that: the compound represented by the general formula II accounts for 1%-50% by weight of the liquid crystal composition.

本发明的进一步改进在于:液晶组合物中组分A占液晶组合物的重量百分含量为18%~33%,组分B占液晶组合物的重量百分含量为28%~60%,组分C占液晶组合物的重量百分含量为18%~43%,上述组分A、组分B、组分C的重量百分含量为100%;The further improvement of the present invention is that: in the liquid crystal composition, component A accounts for 18% to 33% by weight of the liquid crystal composition, and component B accounts for 28% to 60% by weight of the liquid crystal composition. Component C accounts for 18% to 43% by weight of the liquid crystal composition, and the weight percentage of the above components A, B and C is 100%;

本发明的进一步改进在于:还包含稳定剂,所述稳定剂占组分A、组分B、组分C重量之和的0.01%~0.5%;The further improvement of the present invention lies in: further comprising a stabilizer, and the stabilizer accounts for 0.01% to 0.5% of the weight sum of component A, component B and component C;

本发明的进一步改进在于:所述稳定剂为酚类抗氧化剂和/或苯并三唑类紫外吸收剂。The further improvement of the present invention is that: the stabilizer is a phenolic antioxidant and/or a benzotriazole ultraviolet absorber.

由于采用了上述技术方案,本发明所取得的技术进步在于:Owing to adopting above-mentioned technical scheme, the technological progress that the present invention obtains is:

通过本发明得到的向列相型液晶组合物性能优异,具有短的总响应时间、较低的电压、高的电阻率及电压保持率。通过对各个组分含量的调整,本发明所述的向列相型液晶组合物可以具有不同阈值电压和双折射特性,便于在不同液晶盒厚和不同驱动电压下使用,可以满足客户不同需求。同时此液晶组合物表现出优异的高温稳定性和紫外稳定性。The nematic liquid crystal composition obtained by the invention has excellent properties, and has short total response time, low voltage, high resistivity and voltage retention. By adjusting the content of each component, the nematic liquid crystal composition of the present invention can have different threshold voltages and birefringence characteristics, which is convenient for use under different liquid crystal cell thicknesses and different driving voltages, and can meet different needs of customers. At the same time, the liquid crystal composition exhibits excellent high temperature stability and ultraviolet stability.

本发明的液晶组合物,可以用于制造有源矩阵显示器,优选通过薄膜晶体管(TFT)的矩阵寻址,特别适用于制造快速响应的有源矩阵TN-TFT,IPS-TFT或FFS-TFT液晶显示元件和液晶显示器。The liquid crystal composition of the present invention can be used to manufacture active matrix displays, preferably through the matrix addressing of thin film transistors (TFT), and is particularly suitable for the manufacture of fast-response active matrix TN-TFT, IPS-TFT or FFS-TFT liquid crystals Display elements and liquid crystal displays.

具体实施方式Detailed ways

下面结合具体实施例对本发明作进一步阐述:The present invention will be further elaborated below in conjunction with specific embodiment:

实施例中的符号的具体意义及测试条件如下:The concrete meaning and test condition of the symbol in the embodiment are as follows:

Cp:单位℃,表示液晶的清亮点。Cp: unit ℃, indicating the clearing point of liquid crystal.

S-N:单位℃,表示液晶的晶态到向列相的熔点。S-N: unit °C, indicating the melting point from the crystalline state of the liquid crystal to the nematic phase.

Δn:光学各向异性,Δn=no-ne,其中,no为寻常光的折射率,ne为非寻常光的折射率,测试条件为,589nm,25±0.5℃。Δn: Optical anisotropy, Δn=no-ne, wherein, no is the refractive index of ordinary light, ne is the refractive index of extraordinary light, and the test conditions are 589nm, 25±0.5°C.

Δε:介电各向异性,Δε=ε,其中,ε为平行于分子轴的介电常数,ε为垂直于分子轴的介电常数,测试条件为25±0.5℃;1KHz;HP4284A;5.2微米TN左旋盒。Δε: Dielectric anisotropy, Δε=ε , where ε is the dielectric constant parallel to the molecular axis, ε is the dielectric constant perpendicular to the molecular axis, and the test condition is 25±0.5°C; 1KHz; HP4284A; 5.2 micron TN L-box.

γ1:旋转粘度,单位mPa·s,测试条件为25±0.5℃。γ 1 : rotational viscosity, in mPa·s, the test condition is 25±0.5°C.

含二氟亚甲基醚基化合物的液晶组合物,包括由通式I和通式II所示的介电正性化合物组成的组分A、由一种或多种通式III所示的化合物组成的组分B、由一种或多种通式IV所示的化合物组成的组分C;A liquid crystal composition containing a difluoromethylene ether compound, comprising a component A consisting of dielectrically positive compounds represented by general formula I and general formula II, and one or more compounds represented by general formula III Component B composed of, component C composed of one or more compounds represented by general formula IV;

其中,in,

R1、R5分别为H或者C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任一基团;或者为C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任意H被F取代后的任一基团;R 1 and R 5 are respectively H or C 1 to C 10 straight chain alkyl, C 1 to C 10 straight chain alkoxy, C 2 to C 10 straight chain alkenyl, C 3 to C 8 straight chain alkenyloxy Any of the groups; or C 1 ~ C 10 straight chain alkyl, C 1 ~ C 10 straight chain alkoxy, C 2 ~ C 10 straight chain alkenyl, C 3 ~ C 8 straight chain alkenyloxy Any group after any H in is replaced by F;

R2、R3、R4、R6分别为下列①~④所述基团的其中任一种:R 2 , R 3 , R 4 , and R 6 are any of the groups described in the following ①~④ respectively:

①:H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5①: H, Cl, F, CN, OCN, OCF 3 , CF 3 , CHF 2 , CH 2 F, OCHF 2 , SCN, NCS, SF 5 ,

②:C1~C15直链烷基、C1~C15直链烷氧基、C2~C15直链烯基、C2~C15直链烯氧基,②: C 1 ~ C 15 straight chain alkyl, C 1 ~ C 15 straight chain alkoxy, C 2 ~ C 15 straight chain alkenyl, C 2 ~ C 15 straight chain alkenyloxy,

③:②中所述基团中的一个或多个-CH2-被-CH=CH-、-C≡C-、-COO-、-OOC-、亚环丁基、亚环戊基、-O-或-S-替代后且氧原子不直接相连的基团,③: One or more of -CH 2 - in the groups mentioned in ② is replaced by -CH=CH-, -C≡C-, -COO-, -OOC-, cyclobutylene, cyclopentylene, - O- or -S-substituted groups with oxygen atoms not directly connected,

④:②或者③中所述基团的任意H被F、Cl取代后的基团;④: A group in which any H of the group mentioned in ② or ③ is replaced by F or Cl;

(F)分别为H或F;(F) H or F respectively;

Z1、Z2、Z3分别为单键、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-、-CF=CF-中的一种;Z 1 , Z 2 , Z 3 are single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -CH=CH-, -C ≡C-, -COO-, -OOC-, -CF 2 O-, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 - , -C One of 2 F 4 -, -CF=CF-;

A1、A2、A3、A4、A5、A6、A7、A8、A9分别为

Figure BDA0000387402310000061
Figure BDA0000387402310000062
中的一种;A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 are respectively
Figure BDA0000387402310000061
Figure BDA0000387402310000062
one of

a、b、d、e、f、g、h分别为0或1或2或3;c为1或2,并且a+b+c≤5。a, b, d, e, f, g, h are 0 or 1 or 2 or 3 respectively; c is 1 or 2, and a+b+c≤5.

本发明的含二氟亚甲基醚基化合物的液晶组合物中组分A占液晶组合物的重量百分含量为1%~80%,优选18%~33%;组分B占液晶组合物的重量百分含量为1%~60%,优选28%~60%;组分C占液晶组合物的重量百分含量为1%~50%,优选18%~43%;上述组分A、组分B、组分C的重量百分含量为100%。In the liquid crystal composition containing a difluoromethylene ether compound of the present invention, component A accounts for 1% to 80% by weight of the liquid crystal composition, preferably 18% to 33%; component B accounts for 1% to 80% by weight of the liquid crystal composition; The weight percentage of the liquid crystal composition is 1% to 60%, preferably 28% to 60%; the weight percentage of component C in the liquid crystal composition is 1% to 50%, preferably 18% to 43%; the above components A, The weight percentage of component B and component C is 100%.

本发明的含二氟亚甲基醚基化合物的液晶组合物中通式I所示的化合物占液晶组合物的重量百分含量为1%~50%;通式II所示的化合物占液晶组合物的重量百分含量为1%~50%。In the liquid crystal composition containing difluoromethylene ether compounds of the present invention, the compound represented by general formula I accounts for 1% to 50% by weight of the liquid crystal composition; the compound represented by general formula II accounts for 1% to 50% of the liquid crystal composition; The weight percentage of the compound is 1%~50%.

另外,本发明的含二氟亚甲基醚基化合物的液晶组合物还包含稳定剂,稳定剂占组分A、组分B、组分C重量之和的0.01%~0.5%;稳定剂为酚类抗氧化剂和/或苯并三唑类紫外吸收剂。In addition, the liquid crystal composition containing difluoromethylene ether compounds of the present invention also includes a stabilizer, and the stabilizer accounts for 0.01% to 0.5% of the weight sum of component A, component B and component C; the stabilizer is Phenolic antioxidants and/or benzotriazole UV absorbers.

本发明的含二氟亚甲基醚基化合物中通式I所示化合物可以优选下列式I-1~式I-10所示化合物中的一种或几种,通式II所示化合物可以优选下列式II-1~式II12所示化合物中的一种或几种,通式III所示化合物可以优选下列式III-1~式III-9所示化合物中的一种或几种,通式IV所示化合物可以优选下列式IV-1~式IV-12所示化合物中的一种或几种,Among the difluoromethylene ether group-containing compounds of the present invention, the compound shown in the general formula I can be preferably one or more of the compounds shown in the following formula I-1 to formula I-10, and the compound shown in the general formula II can be preferably One or more of the compounds shown in the following formula II-1 to formula II12, the compound shown in general formula III can be preferably one or more of the compounds shown in the following formula III-1 to formula III-9, the general formula The compound shown in IV can be preferably one or more of the compounds shown in the following formula IV-1 ~ formula IV-12,

Figure BDA0000387402310000064
Figure BDA0000387402310000064

Figure BDA0000387402310000071
Figure BDA0000387402310000071

Figure BDA0000387402310000081
Figure BDA0000387402310000081

Figure BDA0000387402310000091
Figure BDA0000387402310000091

Figure BDA0000387402310000101
Figure BDA0000387402310000101

其中,in,

R1、(F)的含义与前述相同;The meanings of R 1 and (F) are the same as above;

R3、R4、R5分别为H或者C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任一基团;R 3 , R 4 , and R 5 are H or C 1 -C 10 straight chain alkyl, C 1 -C 10 straight chain alkoxy, C 2 -C 10 straight chain alkenyl, C 3 -C 8 straight chain Any group in the alkenyloxy group;

R2、R6分别为H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5中的一种。R 2 and R 6 are respectively one of H, Cl, F, CN, OCN, OCF 3 , CF 3 , CHF 2 , CH 2 F, OCHF 2 , SCN, NCS, and SF 5 .

本发明的含二氟亚甲基醚基化合物中通式I所示化合物可以进一步优选为下列式I-1-1~式I-10-5所示化合物中的一种或几种,通式II所示化合物具体为下列式II-1-1~式II-12-1所示化合物中的一种或几种,Among the difluoromethylene ether group-containing compounds of the present invention, the compound shown in the general formula I can be further preferably one or more of the compounds shown in the following formula I-1-1 to formula I-10-5, the general formula The compound shown in II is specifically one or more of the compounds shown in the following formula II-1-1 ~ formula II-12-1,

Figure BDA0000387402310000102
Figure BDA0000387402310000102

Figure BDA0000387402310000121
Figure BDA0000387402310000121

Figure BDA0000387402310000131
Figure BDA0000387402310000131

Figure BDA0000387402310000141
Figure BDA0000387402310000141

Figure BDA0000387402310000151
Figure BDA0000387402310000151

Figure BDA0000387402310000161
Figure BDA0000387402310000161

Figure BDA0000387402310000171
Figure BDA0000387402310000171

在以下的实施例1~6中所采用的各组分,均可以通过公知的方法进行合成,或者通过商业途径获得。这些合成技术是常规的,所得到的各液晶化合物经测试符合电子类化合物标准。Each component used in the following Examples 1-6 can be synthesized by known methods, or can be obtained through commercial channels. These synthesis techniques are conventional, and the obtained liquid crystal compounds are tested to meet the standards of electronic compounds.

按照以下实施例1~6规定的各液晶组合物的重量百分含量,制备液晶组合物。所述液晶组合物的制备是按照本领域的常规方法进行的,如采取加热,超声波,悬浮等方式按照规定比例混合制得。The liquid crystal composition was prepared according to the weight percent content of each liquid crystal composition specified in the following Examples 1-6. The preparation of the liquid crystal composition is carried out according to conventional methods in the field, such as heating, ultrasonication, suspension, etc., and mixed according to the specified ratio.

实施例1Example 1

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

Figure BDA0000387402310000181
Figure BDA0000387402310000181

将上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:100℃;S-N:≤-40℃;Δn:0.105;Δε:8.6;γ1:91.6mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 100°C; SN: ≤-40°C; Δn: 0.105; Δε: 8.6; γ 1 : 91.6mPa·s.

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

实施例2Example 2

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

Figure BDA0000387402310000191
Figure BDA0000387402310000191

将上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:99℃;S-N:≤-40℃;Δn:0.095;Δε:7.8;γ1:94.6mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 99°C; SN: ≤-40°C; Δn: 0.095; Δε: 7.8; γ 1 : 94.6mPa·s.

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

实施例3Example 3

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

Figure BDA0000387402310000201
Figure BDA0000387402310000201

行上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:100℃;S-N:≤-40℃;Δn:0.100;Δε:10.0;γ1:105.5mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 100°C; SN: ≤-40°C; Δn: 0.100; Δε : 10.0;

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

实施例4Example 4

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

Figure BDA0000387402310000211
Figure BDA0000387402310000211

将上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:105℃;S-N:≤-40℃;Δn:0.099;Δε:9.2;γ1:97.8mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 105°C; SN: ≤-40°C; Δn: 0.099; Δε: 9.2; γ 1 : 97.8mPa·s.

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

实施例5Example 5

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

将上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:100℃;S-N:≤-30℃;Δn:0.112;Δε:9.5;γ1:97.7mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 100°C; SN: ≤-30°C; Δn: 0.112; Δε: 9.5; γ 1 : 97.7mPa·s.

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

实施例6Example 6

按如下所列的各化合物及重量百分含量配制成本发明的液晶组合物,Prepare the liquid crystal composition of the present invention according to each compound listed below and the weight percentage content,

Figure BDA0000387402310000231
Figure BDA0000387402310000231

将上述液晶组合物填充于液晶显示器两基板间进行性能测试,测试结果为:Cp:100℃;S-N:≤-40℃;Δn:0.085;Δε:8.0;γ1:93mPa·s。The above liquid crystal composition was filled between the two substrates of the liquid crystal display for performance testing. The test results were: Cp: 100°C; SN: ≤-40°C; Δn: 0.085; Δε: 8.0; γ 1 : 93mPa·s.

该液晶组合物具有适中的双折射率,适当高的正介电,很低的旋转黏度,很快的响应时间,因此非常适合快速响应的TN-TFT、IPS-TFT和FFS-TFT显示器。The liquid crystal composition has moderate birefringence, suitably high positive dielectric, very low rotational viscosity and fast response time, so it is very suitable for fast response TN-TFT, IPS-TFT and FFS-TFT displays.

以上6个实施例,光学各向异性适中,均具有大的介电各向异性,较高的清亮点,很好的低温稳定性,低旋转粘度,在低温区域维持快的响应时间。可拓宽TN-TFT、IPS-TFT或者FFS-TFT液晶模式的使用温度,并且具有较快的响应时间和较宽的视角范围,非常适用于低电压驱动的TN-TFT、IPS-TFT和FFS-TFT显示。The above six embodiments have moderate optical anisotropy, large dielectric anisotropy, high clearing point, good low temperature stability, low rotational viscosity, and fast response time in low temperature regions. It can broaden the operating temperature of TN-TFT, IPS-TFT or FFS-TFT liquid crystal mode, and has a faster response time and a wider viewing angle range, which is very suitable for TN-TFT, IPS-TFT and FFS-TFT driven by low voltage TFT display.

本发明虽然仅仅列举了上述6个实施例的具体化合物及其配比用量(重量百分含量),并进行了性能测试,但是本发明的液晶组合物可以在上述实施例的基础上,利用本发明所涉及的通式I、II、III、IV所代表的液晶化合物、以及通式I、II、III、IV的优选液晶化合物进行进一步拓展和修改,通过对其配比用量进行适当调整,均能达到本发明的目的。Although the present invention only enumerates the specific compounds and their proportioning amounts (percentage by weight) of the above-mentioned 6 embodiments, and has carried out performance tests, the liquid crystal composition of the present invention can be used on the basis of the above-mentioned embodiments. The liquid crystal compounds represented by the general formulas I, II, III, and IV involved in the invention, as well as the preferred liquid crystal compounds of the general formulas I, II, III, and IV, are further expanded and modified. Can achieve the purpose of the present invention.

Claims (9)

1.含二氟亚甲基醚基化合物的液晶组合物,其特征在于:1. The liquid crystal composition containing difluoromethylene ether group compound, it is characterized in that: 包括由通式I和通式II所示的介电正性化合物组成的组分A、由一种或多种通式III所示的化合物组成的组分B、由一种或多种通式IV所示的化合物组成的组分C;Comprising component A consisting of dielectrically positive compounds represented by general formula I and general formula II, component B composed of one or more compounds represented by general formula III, composed of one or more general formulas Component C composed of compounds shown in IV;
Figure FDA0000387402300000011
Figure FDA0000387402300000011
其中,in, R1、R5分别为H或者C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任一基团;或者为C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任意H被F取代后的任一基团;R 1 and R 5 are respectively H or C 1 to C 10 straight chain alkyl, C 1 to C 10 straight chain alkoxy, C 2 to C 10 straight chain alkenyl, C 3 to C 8 straight chain alkenyloxy Any of the groups; or C 1 ~ C 10 straight chain alkyl, C 1 ~ C 10 straight chain alkoxy, C 2 ~ C 10 straight chain alkenyl, C 3 ~ C 8 straight chain alkenyloxy Any group after any H in is replaced by F; R2、R3、R4、R6分别为下列①~④所述基团的其中任一种:R 2 , R 3 , R 4 , and R 6 are any of the groups described in the following ①~④ respectively: ①:H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5①: H, Cl, F, CN, OCN, OCF 3 , CF 3 , CHF 2 , CH 2 F, OCHF 2 , SCN, NCS, SF 5 , ②:C1~C15直链烷基、C1~C15直链烷氧基、C2~C15直链烯基、C2~C15直链烯氧基,②: C 1 ~ C 15 straight chain alkyl, C 1 ~ C 15 straight chain alkoxy, C 2 ~ C 15 straight chain alkenyl, C 2 ~ C 15 straight chain alkenyloxy, ③:②中所述基团中的一个或多个-CH2-被-CH=CH-、-C≡C-、-COO-、-OOC-、亚环丁基、亚环戊基、-O-或-S-替代后且氧原子不直接相连的基团,③: One or more of -CH 2 - in the groups mentioned in ② is replaced by -CH=CH-, -C≡C-, -COO-, -OOC-, cyclobutylene, cyclopentylene, - O- or -S-substituted groups with oxygen atoms not directly connected, ④:②或者③中所述基团的任意H被F、Cl取代后的基团;④: A group in which any H of the group mentioned in ② or ③ is replaced by F or Cl; (F)为H或F;(F) is H or F; Z1、Z2、Z3分别为单键、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-、-CF=CF-中的一种;Z 1 , Z 2 , Z 3 are single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -CH=CH-, -C ≡C-, -COO-, -OOC-, -CF 2 O-, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 - , -C One of 2 F 4 -, -CF=CF-; A1、A2、A3、A4、A5、A6、A7、A8、A9分别为
Figure FDA0000387402300000021
Figure FDA0000387402300000022
Figure FDA0000387402300000023
中的一种;
A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 are respectively
Figure FDA0000387402300000021
Figure FDA0000387402300000022
Figure FDA0000387402300000023
one of
a、b、d、e、f、g、h分别为0或1或2或3;c为1或2,并且a+b+c≤5。a, b, d, e, f, g, h are 0 or 1 or 2 or 3 respectively; c is 1 or 2, and a+b+c≤5.
2.根据权利要求1所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:液晶组合物中组分A占液晶组合物的重量百分含量为1%~80%,组分B占液晶组合物的重量百分含量为1%~60%,组分C占液晶组合物的重量百分含量为1%~50%。2. The liquid crystal composition containing difluoromethylene ether group compound according to claim 1, characterized in that: in the liquid crystal composition, component A accounts for 1% to 80% by weight of the liquid crystal composition, Component B accounts for 1%-60% by weight of the liquid crystal composition, and component C accounts for 1%-50% by weight of the liquid crystal composition. 3.根据权利要求2所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:所述通式I所示的化合物占液晶组合物的重量百分含量为1%~50%。3. The liquid crystal composition containing a difluoromethylene ether compound according to claim 2, wherein the compound represented by the general formula I accounts for 1% to 50% by weight of the liquid crystal composition. %. 4.根据权利要求2所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:所述通式II所示的化合物占液晶组合物的重量百分含量为1%~50%。4. The liquid crystal composition containing a difluoromethylene ether compound according to claim 2, wherein the compound represented by the general formula II accounts for 1% to 50% by weight of the liquid crystal composition. %. 5.根据权利要求2所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:液晶组合物中组分A占液晶组合物的重量百分含量为18%~33%,组分B占液晶组合物的重量百分含量为28%~60%,组分C占液晶组合物的重量百分含量为18%~43%,上述组分A、组分B、组分C的重量百分含量为100%。5. The liquid crystal composition containing difluoromethylene ether compounds according to claim 2, characterized in that: component A in the liquid crystal composition accounts for 18% to 33% by weight of the liquid crystal composition, Component B accounts for 28% to 60% by weight of the liquid crystal composition, and component C accounts for 18% to 43% by weight of the liquid crystal composition. The above components A, B and C The weight percentage is 100%. 6.根据权利要求1~5任一项所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:还包含稳定剂,所述稳定剂占组分A、组分B、组分C重量之和的0.01%~0.5%。6. The liquid crystal composition containing a difluoromethylene ether compound according to any one of claims 1 to 5, characterized in that: it also comprises a stabilizer, and the stabilizer accounts for component A, component B, 0.01% to 0.5% of the weight sum of components C. 7.根据权利要求6所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:所述稳定剂为酚类抗氧化剂和/或苯并三唑类紫外吸收剂。7. The liquid crystal composition containing difluoromethylene ether compounds according to claim 6, characterized in that: the stabilizer is a phenolic antioxidant and/or a benzotriazole ultraviolet absorber. 8.根据权利要求1所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:8. the liquid crystal composition containing difluoromethylene ether group compound according to claim 1, is characterized in that: 所述通式I所示化合物具体为下列式I-1~式I-10所示化合物中的一种或几种,The compound represented by the general formula I is specifically one or more of the compounds represented by the following formula I-1 to formula I-10,
Figure FDA0000387402300000031
Figure FDA0000387402300000031
所述通式II所示化合物具体为下列式II-1~式II12所示化合物中的一种或几种,The compound represented by the general formula II is specifically one or more of the compounds represented by the following formula II-1 to formula II12,
Figure FDA0000387402300000042
Figure FDA0000387402300000042
所述通式III所示化合物具体为下列式III-1~式III-9所示化合物中的一种或几种,The compound represented by the general formula III is specifically one or more of the compounds represented by the following formula III-1 to formula III-9,
Figure FDA0000387402300000052
Figure FDA0000387402300000052
所述通式IV所示化合物具体为下列式IV-1~式IV-12所示化合物中的一种或几种,The compound represented by the general formula IV is specifically one or more of the compounds represented by the following formula IV-1 to formula IV-12,
Figure FDA0000387402300000061
Figure FDA0000387402300000061
Figure FDA0000387402300000071
Figure FDA0000387402300000071
其中,in, R3、R4、R5分别为H或者C1~C10直链烷基、C1~C10直链烷氧基、C2~C10直链烯基、C3~C8直链烯氧基中的任一基团;R 3 , R 4 , and R 5 are H or C 1 -C 10 straight chain alkyl, C 1 -C 10 straight chain alkoxy, C 2 -C 10 straight chain alkenyl, C 3 -C 8 straight chain Any group in the alkenyloxy group; R2、R6分别为H、Cl、F、CN、OCN、OCF3、CF3、CHF2、CH2F、OCHF2、SCN、NCS、SF5中的一种。R 2 and R 6 are respectively one of H, Cl, F, CN, OCN, OCF 3 , CF 3 , CHF 2 , CH 2 F, OCHF 2 , SCN, NCS, and SF 5 .
9.根据权利要求8所述的含二氟亚甲基醚基化合物的液晶组合物,其特征在于:9. the liquid crystal composition containing difluoromethylene ether group compound according to claim 8, is characterized in that: 所述通式I所示化合物具体为下列式I-1-1~式I-10-5所示化合物中的一种或几种,The compound represented by the general formula I is specifically one or more of the compounds represented by the following formula I-1-1 to formula I-10-5,
Figure FDA0000387402300000081
Figure FDA0000387402300000081
Figure FDA0000387402300000091
Figure FDA0000387402300000091
Figure FDA0000387402300000101
Figure FDA0000387402300000101
Figure FDA0000387402300000111
Figure FDA0000387402300000111
Figure FDA0000387402300000121
Figure FDA0000387402300000121
所述通式II所示化合物具体为下列式II-1-1~式II-12-1所示化合物中的一种或几种,The compound represented by the general formula II is specifically one or more of the compounds represented by the following formula II-1-1 to formula II-12-1,
Figure FDA0000387402300000122
Figure FDA0000387402300000122
Figure FDA0000387402300000131
Figure FDA0000387402300000131
Figure FDA0000387402300000141
Figure FDA0000387402300000141
CN201310442001.7A 2013-09-25 2013-09-25 Containing the liquid-crystal composition of difluoro methylene based compound Active CN103525433B (en)

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