TW200804568A - High birefringent liquid crystal compound and composition thereof - Google Patents

Abstract

This invention provides a compound for a liquid crystal display and composition thereof. This invention can obtain high birefringence (Δn ≥ 0.3), broad liquid crystal phase, high stability and high compatibility by using a compound containing the structure of dibenzofuran and its derivatives. Using the present liquid crystal composition with high birefringence can increase reflective efficiency, contrast and reflectable wavelength range of a reflective liquid crystal display.

Description

200804568 IX. Description of the Invention: [Technical Field] The present invention relates to a compound for a liquid crystal display; and further, the present invention relates to a liquid crystal compound formulation having a high refractive index. / ' [Previous technology] In today's fast-changing technology, people are getting higher and higher for display products, not only wanting to have higher resolution, but also making products more and more thin and convenient for people to use; so LCD plane The display has gradually become the mainstream of the market. However, for the long-term needs of liquid crystal flat-panel displays, the improvement in the process can be improved. The liquid crystal will affect the second component of the device, which is the most important raw material, and plays a fortunate position on the liquid crystal display. . Traditional transmissive LCDs are too cumbersome and power hungry to meet their needs for portable e-commerce. Reflective LCD uses ambient light as a light source, eliminating the power consumption, weight, thickness and cost of the backlight module. In addition, it also overcomes the problem of insufficient brightness of penetrating LCDs when used outdoors. Various liquid crystal displays that can be carried in medium and small sizes, such as e-bo〇k, e-magazine, PDA, etc., appear on the market in the future. LCD products will be the focus of development. However, the traditional transmissive LCD and the reflective LCD have significantly less reflectivity than the general book newspapers, so it is necessary to improve this sex month b as soon as possible to enter the market. The most critical way to increase reflectivity is to develop on its liquid crystal materials. The reflective liquid crystal display panel uses Bragg reflection to reflect light with a spectral width of Δλ=Δηχρ (where p is 200804568 pitch, Δη is birefringence, ie, the larger the inverse, the inverse of it is known to be Δ ^Δη is proportional to the ideal. In the case of ideal, the larger the 瑨觅 is, the higher the brightness is. In the spectrum, the current brightness and reflected light are only observed. No - LCD "ο. 2, so the reflection of brightness is difficult, and by 桓浐叮 η - 1 after all, the theoretical value, to develop the entire coverage; = when -6, its reflection spectrum width and high birefringence Rate::250%', so if it can be developed due to the use of high birefringence, it will improve the overall performance. The liquid crystal material of the shooting efficiency, contrast sound, and the radiance can make the trans-type LCD, the night, the night The wavelength range of the reflection of the β^β is improved. Therefore, the product of general reflection (4) is oriented toward high contrast and high reflectivity. The “ff quality depends mainly on the properties of the liquid crystal material”. Liquid helium of refractive index value (ΔGW) 'It should also have the ideal properties of general liquid crystal materials, such as · Wide liquid crystal phase temperature range (operating temperature is -1Q~5 (rc, storage temperature is 40~8 (rc), with optical and chemical stability (Lifetime > 20, 〇〇〇 hours used), good compatibility between liquid crystal molecules and optically doped (6丨1^1 de〇pant) (solubility 2 20%), driving voltage <25V , contrast > 10/1, and white light reflectivity > 35%, etc., if a high birefringence liquid crystal material (Δng〇4) having a broad liquid crystal phase, high stability and high compatibility can be developed, The liquid crystal display industry or related products mainly based on liquid crystal materials can be helpful. [Invention] In view of the liquid crystal display industry's need for 焉 birefringence liquid crystal material, the purpose of the present invention, the liquid crystal of the information The early gentleman 搂 has a high birefringence at 0 and leaves (Δι^〇·4). There are liquid crystal panels: reflections; night crystals (4) large birefringence, black i曰,). Should have better, liquid si fiber, ~ low viscosity, Low melting point, photothermal stability, good solubility = production = 俨 = wide, and excellent reading point for liquid crystal (NematicHost) will be able to improve the liquid crystal display

Have the following

^ In the ς, A1, A2, and each are independently selected from hydrogen, halogen, cyano or squirrel, and Rl is hydrogen, halogen, cvc12 alkyl, Cl-Cl2oxy, CV^2 haloalkyl , CVCi2 haloalkoxy, alkenyl (=), alkynyl (g), alkenyl, pyridyl or an aromatic group substituted by at least-the remainder or by a lenon, C"C6 alkyl or CrC6 haloalkyl The aromatic group is composed of hydrogen, halogen, CrC6 alkyl or crC6 haloalkyl. In a preferred embodiment, Ri is a Ci_c6 alkyl group, for example, a compound represented by the following chemical formula: 200804568 c3h7

The present invention further provides a compound having the structure represented by the following chemical formula (π):

Wherein, Ai, A2, and A3 are each independently selected from the group consisting of hydrogen, halogen, cyano or sulphur, and R1 is nitrogen, halogen, Cl-Cl 2 alkyl, Cl-Cl 2 alkoxy, Ci-C 12 200804568 Haloalkyl, crc12-alkoxy, alkenyl (=), alkynyl (b), alkenyl, alkynyl or substituted by at least one unsubstituted or halogen, CrQ alkyl or crc6 haloalkyl An aromatic group consisting of an aromatic group; and R2 is hydrogen, halogen, crc6 alkyl or crc6i. In a preferred embodiment, Ri is a CrC6 alkyl group, such as the compound shown by the following chemical formula:

The high birefringence compound of the present invention is used for incorporation into a liquid crystal solution to increase the birefringence of the liquid crystal solution. Therefore, the present invention provides a liquid crystal composition comprising at least: 0.5% to 35% by weight of the following chemical formula Compound of the structure shown in (III)

(III); and 65% to 99.5% by weight of the liquid crystal formulation; wherein, Ai, A2, and A3 are each independently selected from the group consisting of hydrazine, halogen, cyano or thiocyanyl; and the core is hydrogen, halogen, CrCu alkyl , (^-(: alkoxy, Ci-C) 2 alkyl, Ci**Ci2 halogen alkoxy, fine (), decyl (), alkenyl, alkynyl or by at least one An aromatic group substituted with an aromatic group substituted with a halogen, a crc6 alkyl group or a crc6i alkyl group; when the 1 system is an aromatic group having two or more aromatic rings, the aromatic ring system utilizes 9 200804568 The base (or alkynyl group) is attached in a partial embodiment, wherein the core is a phenyl substituted by a CrQ alkyl group such as the compound of the following formula: c4h9- and c4h9

In a preferred embodiment of the liquid crystal composition of the present invention, the compound (III) accounts for 5% to 20% by weight of the liquid crystal composition. The liquid crystal formulation in the liquid crystal composition of the present invention comprises the above compound (I) and/or compound (II), for example, the compound (I) and the compound (II) represented by the following chemical formula:

F

// XX 丨, \\ n F

C3h7- C3H7

-F 10 200804568

C4h9

As apparent from the above, the present invention provides a liquid crystal composition comprising 0.5% to 35% by weight of a compound of the following formula (III); and 65% to 99.5% by weight of the compound (I) and/or Compound (II).

The invention further provides a method for measuring birefringence, the method comprising: placing a liquid crystal sample in a liquid crystal cell; taking a first polarizer and a second polarizer respectively on opposite sides of the liquid crystal cell, wherein A polarizer and the second polarizer are orthogonal; a laser beam is passed through the first polarizer, the liquid crystal cell and the second polarizer, and a light detector is used to detect the transmittance and the wave shape of the beam; Adjusting the first polarizer and/or the second polarizer to minimize the transmittance measured by the photodetector; applying a voltage to the liquid crystal sample in the liquid crystal cell by using a signal generator, the voltage is gradually increased from 0V to 10V; And providing a control interface coupled to the photodetector for recording the transmittance and waveform acquired by the photodetector, the control interface including a software for calculating the birefringence from the graph formed by the transmittance. The pattern formed by measuring the transmittance obtained by measuring the birefringence can be 200804568

For measuring the rotational viscosity of the sample, therefore, the present invention also includes an amount: the method of rotating the viscosity, which is obtained by the step of measuring the birefringence in the step 11 by obtaining the pattern of the penetration formed by the soft body of the control interface. The step _step defines the difference between the voltage value of the first signal trough from the 0V to 10V in the aforementioned transmittance pattern voltage is the input voltage vappi; the control signal generates the liquid crystal applied to the liquid crystal cell Sample a vappl voltage; release the voltage to 0V after the appropriate time is stabilized, and take the light detection by the control interface; cry: the waveform of the acquisition; and the software calculation using the control interface "/K11,;;::: The value of κη is obtained as a rotational viscosity (rl) value. As is known from the above, the present invention also provides a device for measuring birefringence and/or Han degrees, which comprises: - a laser source for providing a desired beam; The source beam path is used to hold a sample of 2 liquids, a first polarizing plate and a second polarizing plate, which are respectively in front of and behind the liquid crystal cell on the beam path of the laser source, and the first in the basin. Polarized plate; the:: the plate is orthogonal; the light detector is used to detect the light beam, the transmittance and wave pattern of the liquid crystal cell and the second polarizing plate; a liquid crystal voltage in the liquid crystal cell; and a control interface, the detector is connected to receive the transparency of the photodetector detection; and the second uranium control interface includes a software for recording the photodetector wearing The resulting pattern is also recalculated to calculate the birefringence and rotational viscosity. The liquid crystal compound of the present invention, wherein the composition of the liquid crystal formulation is a liquid crystal formulation made of a swarf type cholesteric liquid crystal display or a polymer dispersed liquid crystal display. The liquid crystal composition of the present invention has a birefringence of 2 〇·3, and when it is incorporated into a liquid crystal formulation, the birefringence and reflected wave of the liquid crystal formulation can be improved to improve the performance of the liquid crystal display. With the method and apparatus for measuring the birefringence and/or rotational viscosity of the present invention, the σ & AbbeRefractometer can be used to break the conventional sample such as η>0·2 or more. A suitable and fast solution is provided for the art of denier = Δ. The birefringence of the sample is measured. [Embodiment] The present invention utilizes chemical structure changes, characteristics and physical light (four) properties, and money is passed on, in order to meet the chemical characteristics, the ideal liquid crystal material should have, . Liquid crystal phase range; (2) low melting point; (3) low heat of dissolution; and (4) physical properties and physical properties, ideal liquid crystal material 4疋, (birefringence, Δη) and low state production / :, should /, Ask birefringence; and low viscosity (vlsc〇sity, η) of Teke. Therefore, the following description is used to understand the change in the physical properties of the difference in the structure of the compound, and further to present the concept of structural design of the compound. In general, the reflection efficiency of the reflective flat panel display, the wavelength range of the I-reacting, can be achieved by the efficiency of a high birefringence liquid helium regulator or by high birefringence: The liquid crystal phase temperature range is mostly in the - buckle. ^ A nematic liquid crystal phase. Further, by increasing the ί ^ I, /, yoke structure, the birefringence will increase. For example, from 1972 ίί ϋ W* ^ 2 . , ^ material 3 ratio " phlegm is more than one compound, so that An increases oj; and compound 3 is more than compound 1 - ° with benzene ring, ΔΠ ^ plus W. It can be seen that the effect of the reference key and the refractive index is similar. Therefore, if the design of the second stupid 13 200804568 骈 furan with two three bonds plus two benzene ring structure, there should be a high resonance effect similar to 5 to 6 benzene rings. Δη=0.2 Διϊ=03 Δο=0.3

CsHii

CN K 24 N 35 I Compound 1 K 80 (N71) I Compound 2 K 130 N 239 I Compound 3

From the liquid crystal phase transition temperature of the three, the introduction of the bond and the benzene ring on the main axis of the molecule can increase the phase transfer temperature, and the effect of the benzene ring on the liquid crystal phase transition temperature is much more significant. The following compounds 4, 5, and 6. Among them, the compound 6 is based on tolane, and the alkyl group and the alkoxy group at the terminal end exhibit a desirable temperature range. The temperature range of compound 5 is extremely narrow, and the compound 4 has no liquid crystal phase.

In 1990, V. Perce published the synthesis of compounds 7, 8. However, the formation of a nematic phase is disadvantageous due to the long carbon bond of the terminal end. 14 200804568

0C7Hi5 compound

Compound 8 h - the following compounds 9, 10; the introduction of a lateral group was found to cause a very low melting point = decrease, but the temperature of the average point (Ti) decreased only slightly. In other words, the range of the liquid crystal phase can be increased to 11 〇. € or so. C6h13· C6Hi3

C2h5 K 134 N 191 I Compound 9 K 57 N 160 I Compound 1〇 Since 1 has not yet had a single liquid crystal compound, it can meet the requirements of the user's dryness. However, using Schr〇dep (6) such as (10), 1, and two! ί 液 eutectic mixture, the melting point of the eutectic mixture will be smaller than the fusible black of each group, as can be seen from the following formula If the melting black of the constituent materials and the lower the heat of fusion, the melting point of the mixture will be lower. Therefore, the liquid crystal synthesized by the present invention is expected to have both low melting point and low heat of fusion.

Grade. △ The heat of fusion of pure substances

Tmi: Melting point of pure substance _ ^ Xi: Molar fraction of pure substance, and then check whether each compound has low viscosity and low melting point characteristics. 1972 G·W. Gary synthesizes cyanobiphenyl (4) (10) (4)) Liquid crystal compound of the series 1 · 15 200804568 Κ 24 N 35 I Compound 1 : 4 The liquid crystal compound of the cyanobiphenyl series has a terminal alkyl group of 5 to 7 B ^ 'having a nematic liquid crystal phase, and liquid crystal The temperature of the phase is between 14 ° C and 42 t :, while the temperature range of the liquid crystal phase is approximately; when the terminal alkyl carbon number is increased to 8 or more, a smectic liquid crystal phase occurs. 】 In 1976, $' Gary and Mosley synthesized a bisphenylacetylene compound 2 containing an acetylene group:

K 80 (N71) I compound 2 4, the series compound exhibits only a nematic liquid phase when the terminal carbon number is 11 or less. When the number of slaves exceeds η, a layered a-type liquid crystal phase appears. Compound

K 130 N 239 I Compound 3

The addition of the ancient 1 comparison 'acetylene linker' lengthens the conjugate length of the molecule, raises the melting point and phase transition temperature, and tends to form a nematic liquid crystal phase. It can be understood from the liquid crystal phase temperatures of the comparative compounds 2, 3. The uv absorption spectrum is similar to Δη, but the viscosity of compound 2 is about two times lower than that of compound 3; in addition, the acetylene linker has the same phenyl ring linker as the acetylene linker and the benzene ring linker. The birefringence, however, has a lower melting point and viscosity than the compound of the phenyl ring linkage. Therefore, in the design of the liquid crystal molecule, an acetylene linkage is introduced to replace the benzene ring to lower the point to obtain a low-temperature, low-viscosity liquid crystal material. And retain its original A △ η value. However, the liquid crystal phase temperature range of this series of liquid crystal compounds is still too small to be practically difficult. 16 200804568 Accordingly, the present invention utilizes some novel bisphenyl diacetylene series of eight species (such as the aforementioned compound of formula (III)), and some bis-peptidyl esters (such as the aforementioned chemical formula (I) and (Π) Compound) and other liquid crystals are used: the compound is combined to form a liquid crystal composition, which has the effects of improving the reflectance of the reflective liquid crystal display, the contrast ratio and the wavelength range of the reflection, and is measured by the self-organized optical laser instrument. After directly measuring the birefringence =, the rotational viscosity value and the rotational viscosity value / elastic modulus of the composition, the ideal clock i is obtained. The sample of the invention is a method for measuring the birefringence of the liquid crystal sample ΔnX). The method of the invention is to exemplify the method of measuring the birefringence of the liquid crystal sample. The steps are as follows: First, the liquid crystal sample to be tested is placed in a liquid crystal cell, and then Taking a first polarizer and a second polarizer respectively disposed on opposite sides of the liquid crystal cell, the deflection angles of the first polarizer and the second polarizer are orthogonal; and then passing a laser beam through the first polarizer After the liquid crystal cell and the second polarizer, the light detector is used to detect the transmittance and the wave shape of the light beam; then the first polarizer and/or the second polarizer are rotated to adjust the light detector to be worn. The transparency is minimal; the voltage is applied to the liquid crystal sample in the liquid crystal cell by using a first-number generator, and the voltage is supplied from 〇V to ιον; in the process, a control interface (such as a computer) and light is utilized. The detector is connected to record the tooth penetration and the waveform acquired by the photodetector, and the control interface comprises a software for calculating the birefringence by the pattern formed by the penetration. The specific embodiment of the software is as in the present technology. Labview Syste known in the field m (refer to the first figure), installed in the computer, and the computer can use the connection interface such as RS-232 to connect with other components (such as light detection state), which can be measured by the Labview System monitoring optical debt detector The resulting pattern of the waveform, the value of the penetration, and the transmittance are used to further calculate the birefringence of the liquid crystal sample (refer to the second figure). 17 200804568 The method for measuring the birefringence of a liquid crystal sample according to the present invention, which further comprises a magnification benefit and a light detection benefit and a control interface connection, and the light penetration measurement signal is amplified by the amplifier and then provided with control ^ surface. The method of the second method may further include a temperature controller connected to the liquid crystal cell and the interface to control the liquid crystal in the liquid crystal cell to maintain a constant temperature, and further, the signal generator of the method of the invention can be connected to the control interface. The connection causes the signal generator to provide the voltage of the liquid crystal in the liquid crystal cell to be regulated by the control interface. ~

The method for measuring the birefringence of a liquid crystal sample of the present invention can further measure the rotational viscosity of the liquid crystal sample, which is based on the measurement of the birefringence; in the middle of the step, the pattern of the penetration formation is obtained by the soft body of the control interface. After that, the voltage in the penetration graph is gradually increased from ον to 10ν, and the difference between the voltage of the first ^^ peak and the first signal valley is the input voltage of the control signal generator to apply Vappl voltage to the liquid crystal. The liquid in the box is ag1. After the 'release of Jing to 0ν' during the use of the work surface, refer to the third figure), and finally use the control, the face of the body juice ri / Kii, and know the K11 value to obtain the rotational viscosity ^ 1 mountain) value, and measurement The difference in birefringence is the soft system for calculating 7l/Kli, such as the software written by matlab system. As can be seen from the above, the present invention actually provides a schematic diagram of a device for measuring the liquid crystal 雔 2 rate and/or rotational viscosity as shown in the fourth figure:: spoon: ·: laser source 'to provide the desired beam; a liquid crystal cell; the beam path of the two sources of the parking space is used to hold the liquid crystal sample n, the light plate and the second polarizing plate to be measured, respectively, which are respectively located in the laser source; a polarizing plate and a second biasing--first detector for detecting the penetration and waveform of the light beam after penetrating the first polarizing plate liquid crystal cell and the polarizing plate of the second-and-a-half polarizer; a signal generator Providing a liquid crystal voltage in the liquid crystal cell; and a control interface coupled to the photodetector for receiving the transparency and the pattern detected by the photodetector, the control interface including at least one software for recording the photodetection The pattern formed by the penetration of the detector and the calculation of birefringence and/or rotational viscosity. The apparatus for measuring the birefringence and/or the rotational viscosity of the liquid crystal sample of the present invention may further include an amplifier coupled to the photodetector and the control interface, so that the transmittance signal of the photodetector can be amplified by the amplifier and then provided. Control device; the device of the present invention may further comprise a temperature controller connected to the liquid crystal cell and the control interface for controlling the liquid crystal in the liquid crystal cell to maintain a constant temperature. Further, the signal generator in the device of the present invention can be controlled The interface is connected so that the voltage generated by the signal generator in the liquid crystal cell is regulated by the control interface. The following aspects are intended to further understand the advantages of the present invention and are not intended to limit the scope of the invention. The addition of the compound of the present invention and the use of the liquid crystal composition of the present invention and the properties of the liquid crystal composition used in the liquid crystal composition of the present invention are as follows: n- represents an alkyl group, and H represents a n-hexane. E represents an ester, B represents benzene, CN represents a nitrogen group, F represents fluorine, τ represents an alkynyl group, and _ represents a methyl group. [pL] represents

, [DF] stands for

19,0200804568

〇hG^〇-cn n-HEBB-CN

n-BTBEB-F 〇~f

10 p

n-BTB(Me)TB-m n-BTBEB-CN

n-BBB-CN n-BTBT[FL]

n-BT[DF] n-BT(Me)BT[DF] The invention is based on the above-mentioned ten kinds of liquid crystal monomers and their related derivation structures, and is not limited to the ten liquid crystal monomers. 20 200804568 In the technical field, the formula is as shown in Table A, Table B, Table C and Table D below, which are mixed with the monomer code and the subsequent ratio: Table A [YC-0861-148]

Monomer ratio (%) C2-HEBB-CN 13 C4-HEBB-CN 17 C2-BTBEB-F 7 C4-BTBEB-F 8 C3-BTBEB-(F,F) 8 C4-BTBEB-(F,F) 11 C4-BTBEB-CN 8 C3-BTB(Me)TB-C6 6 C4-BT[DF] 8 C5-BT[DF] 8 C4-BT(Me)BT[DF] 6 Δ n = 0.338 η :72 mpas B monomer ratio (%) C2-HEBB-CN 13 C4-HEBB-CN 17 C2-BTBEB-F 7 C4-BTBEB-F 8 C3-BTBEB-(F,F) 9 C4-BTBEB-(F,F) 10 C4-BTBEB-CN 8 C3-BTB(Me)TB-C6 6 C4-BT[DF] 8 C5-BT[DF] 8 C4-BT(Me)BT[DF] 6 Δ n = 0.322 η :76 mpas 21 200804568 Table C Monomer ratio (%) C2-HEBB-CN 13 C4-HEBB-CN 16 C2-BTBEB-F 8 C4-BTBEB-F 8 C3-BTBEB-(F,F) 8 C4-BTBEB-(F , F) 11 C4-BTBEB-CN 8 C3-BTB(Me)TB-C6 6 C4-BT[DF] 8 C5-BT[DF] 8 C4-BT(Me)BT[DF] 6 Δ n = 0.325 η :70 mpas Table D Monomer ratio (%) C2-HEBB-CN 13 C4-HEBB-CN 17 C2-BTBEB-F 7 C4-BTBEB-F 9 C3-BTBEB-(F,F) 8 C4-BTBEB-( F,F) 10 C4-BTBEB-CN 8 C3-BTB(Me)TB-C6 6 C4-BT[DF] 8 C5-BT[DF] 8 C4-BT(Me)BT[DF] 6 Δ n = 0.331 η :67 mpas

Comparative Example 1: In Comparative Example 1, the liquid crystal formulations were mixed in the ratios of Table E below to determine their Δη and viscosity (η), wherein the difference between the liquid crystal formulations of Table E and the formulations of Tables A to D was that C4- was not incorporated. BT[DF], C5-BT[DF] and 22 200804568 C4-BT(Me)BT[DF] three liquid crystal monomers. Table E Monomer ratio (%) 2-HEBB-CN 20 4-HEBB-CN 18 C2-BTBEB-F 10 C4-BTBEB-F 13 C3-BTBEB-(F,F) 9 C4-BTBEB-(F,F 10 C4-BTBEB-CN 10 C3-BTB(Me)TB-C6 10 Δη = 0.278 η : 113 mpas Δ η value and rotational viscosity value measured by liquid crystal formulations of Tables A to D and comparison table Comparing the numerical values obtained by Ε, it was found that the liquid crystal formulation of the present invention has a birefringence Δη > 3 and its viscosity is small, and the two are superior to those of Comparative Example 1. Example 2· Reflected Wave Width of Liquid Crystal Composition Containing Composition of the Present Invention (YC-0861-148) The composition of the present invention (YC-0861-148, the formulation of Example 1) was mainly composed. The ratio of Table F is blended with known liquid crystal formulations (ie YC-0861-148 94.7%, the remaining 5.3%, the sum is 100%), and the measurement of the reflection wavelength is performed by the above-mentioned measurement method, and the result is as shown in the fifth figure. Shown. 23 200804568 Table f

Host YC-0861-148 (Δη=0.33) Chiral Dopant CB15 YN0885-099 YN0885-133 YN0771-093 Total Weight Ratio 13% 1.5% 1.1% 1.4% 5.3% χ ϊΑΐΙ ϊΑΐΙ (rim) 560 From the fifth picture, this book The compound of the invention is added to the liquid crystal formulation to improve the birefringence and reflection wavelength of the liquid crystal formulation, which is beneficial to the improvement of the performance of the liquid crystal display. Example 3. Measuring the birefringence and rotational viscosity of a commercially available product using the apparatus for measuring the birefringence and/or rotational viscosity of a liquid crystal sample according to the present invention. The measured birefringence and/or rotational viscosity of a liquid crystal sample. As shown in the fourth figure, the results obtained by measuring the birefringence and rotational viscosity of the Merck ZLI-1840 product using this device are shown in Table G below:

Table G

Cell gap 5700 (from UV ) Cell gap 9300 (from UV ) Merck Product Information Birefringence Δη (633 nm, 22〇C) 0.1417 0.1438 0.1426 ( 589 nm, 20〇C ) 238 [mPa.s] 20°C Rotation Viscosity γ1 [mPa.s]22〇C 187 208 As can be seen from Table G, the value of the birefringence Δη measured by the device operating under different cell gaps is approximately 24 with the value of the Merck catalogue. 200804568 1% On the value of the rotational viscosity r 1 , the error is also less than 10%. The device of the present invention is indeed applicable for measuring the birefringence and rotational viscosity of liquid crystal samples. Example 4. Measuring the Birefringence and Rotational Viscosity of a High Birefringence Liquid Crystal Sample Using the Apparatus for Measuring Birefringence and/or Rotational Viscosity of a Liquid Crystal Sample of the Present Invention The birefringence and/or the measurement of the liquid crystal sample of the present invention The device for rotating the viscosity is shown in the fourth figure. The results obtained by measuring the birefringence and rotational viscosity of the Merck E7 (high birefringence) product using this device are shown in Table H below. Table Η Institute of Research Institute made high birefringence liquid crystal Merck E7 Birefringence Δη 0.2237 (633 nm ) 0.2253 ( 589 nm) Rotational Visibility 71 [mPa] 200 190 From the above, the device for measuring the birefringence and/or rotational viscosity of the liquid crystal sample of the present invention can accurately measure the double A liquid crystal sample having a refractive index Δη value of > 0.2 can solve the bottleneck of the conventional measurement method or device. All of the features disclosed in this specification may be combined with other method combinations 25 200804568, each of the features disclosed in this specification may be selectively replaced with the same, equal or similar purpose features, therefore, All of the features disclosed in this specification are only one example of equal or similar features, except for the particularly salient features. While the invention has been described above in terms of the preferred embodiments thereof, it is not intended to limit the invention, and various modifications and changes can be made without departing from the spirit and scope of the invention.

26 200804568 [Simple description of the diagram] The first figure is a software display interface image of the birefringence of the liquid crystal sample of the present invention. The second figure is a measurement pattern of the birefringence Δη of the present invention. The third figure is a measurement chart of the rotational viscosity of the present invention. The fourth figure is a schematic diagram of the self-assembled measuring liquid crystal sample instrument of the present invention. The fifth figure is the Δ λ reflection spectrum of the liquid crystal formulation to which the compound of the present invention is added.

27

Claims (1)

200804568 X. Patent application scope: 1 · A compound' has a gentleman's structure as shown in the following chemical formula (I) A!, Ay As are independently selected from hydrogen, halogen, cyano or thiocyanyl; K is hydrogen, halogen, CrC12 alkyl, CrC12 alkoxy, CkCi2 haloalkyl, CVC12i alkoxy, alkenyl ( =) an alkynyl group ($), an alkenyl group, an alkynyl group or an aromatic group consisting of at least one aromatic group which is unsubstituted or substituted with a halogen, a Crq alkyl group or a Ci-C6 alkyl group; and the R2 system is Hydrogen, a hydroxyl group, a CrC6 alkyl group or a CVQ haloalkyl group. The compound of claim 1, wherein the aforementioned Ri is a cvc6 alkyl group. 3. The compound of claim 2, which is a compound of the formula: 28 200804568 c3H7 4. A compound having the structure shown by the following chemical formula (II): Among them, A!, Ay As are independently selected from hydrogen, halogen, cyano or thiocyanyl; Ri is hydrogen, halogen, CrC12 alkyl, crC12: l: oxy, CrCi2 halogen, Ci-Cu a halogenated alkoxy group, an alkenyl group (=), an alkynyl group, an alkynyl group, an alkynyl group or an aromatic group consisting of at least one aromatic group which is unsubstituted or substituted by a halogen, a Ci-C6 alkyl group or a CrC6 halogen group. a group; and R2 is hydrogen, halogen, CrC6 alkyl or CrC6 haloalkyl. 5. The compound of claim 4, wherein + the aforementioned & 29 200804568 is a crc6 alkyl group. 6. The compound of claim 5, which is a compound represented by the following chemical formula: 〇,)~(f -CN 7·) a liquid crystal composition comprising at least: 0.5% to 35% by weight of a compound represented by the following chemical formula (m) 65%~99.5% by weight of liquid crystal formulation, wherein A1, A2, and Α3 are each independently selected from hydrogen, halogen, cyano or thiocyanyl; and gastric soil/lanthanide is hydrogen, halogen, crc12 alkyl, 〇^-(: 12 alkoxy, Ci_Ci2 haloalkyl, CVCi2 haloalkoxy, alkenyl (=), alkynyl (s) = alkenyl, alkynyl or by at least one unsubstituted or halogenated, An aromatic group composed of an alkyl group substituted with an alkyl group of a CrC6 haloalkyl group; when the group 1 is an aromatic group having two or more aromatic rings, the aromatic ring is an alkenyl group (one = one) or The alkynyl group is a 1 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The liquid crystal composition according to the above, wherein the compound (III) of the aforementioned 30 200804568 is the following compound: c4h9 10. The liquid crystal composition according to claim 7, wherein the compound (III) is the following compound 11. The liquid crystal composition according to claim 7, wherein the compound (III) accounts for 5% to 20% by weight of the liquid crystal composition. 12. The liquid crystal composition according to claim 7, wherein the liquid crystal formulation comprises the compound (I) of claim 1 and/or the compound (II) according to item 4. 13. The liquid crystal composition according to claim 12, wherein the compound (I) according to the first aspect of the patent application is: F 31 200804568 or 14. The liquid crystal composition according to claim 12, which is a compound represented by the following chemical formula: C2H5 The liquid crystal composition according to claim 8, wherein the composition of the liquid crystal formulation is a liquid crystal formulation used for a reflective cholesteric liquid crystal display or a high molecular dispersed liquid crystal display. A liquid crystal composition comprising at least: 0.5% to 35% by weight of a compound represented by the following chemical formula (ΙΠ) (III) wherein A\, A2, and A3 are independently selected from hydrogen, dentate, sulfhydryl or thiocyanyl, and R is hydrogen, halogen, CrCu alkyl, Ci_Ci2 alkoxy, c, 32 200804568 a aryl group consisting of a aryl group substituted with at least one unsubstituted or substituted by halogen, crc6 alkyl or CrQ haloalkyl. The aromatic group, when the heart is an aromatic group having two or more aromatic rings, the aromatic ring is linked by an alkenyl group (a ==" a) or an alkynyl group (a = one); 65% to 99.5% by weight of the compound (I) of claim 1 and/or the compound of claim 4 (Π). 17. The liquid crystal composition according to claim 16, wherein the above-mentioned ruler is a phenyl group substituted with an alkyl group. The liquid crystal composition according to claim 16, wherein the compound (III) described above is the following compound: 19. The liquid crystal composition according to claim 16, wherein the compound (III) is the following compound C4h9 The liquid crystal composition of claim 16, wherein the compound (III) accounts for 5% to 20% by weight of the liquid crystal composition. 21. The liquid crystal composition according to claim 7, wherein the aforementioned compound (I) is: 33 200804568 23. The liquid crystal composition according to item 16 of the full-time application, which can be applied to a liquid crystal formulation used in a reflective cholesteric liquid crystal display or a polymer dispersed liquid crystal display. 24 - a method for measuring the birefringence of a liquid crystal sample, the steps comprising: 34 200804568 placing a liquid crystal sample in a liquid crystal cell; taking a first polarizer and a second polarizer respectively placed in the liquid crystal cell On the side, the first polarizer and the second polarizer are orthogonal; after passing a laser beam through the first polarizer, the liquid crystal cell and the second polarizer, the light beam is used to detect the penetration of the light beam. Degree and mode; adjusting the first polarizer and/or the second polarizer to minimize the penetration measured by the photodetector; Applying a voltage to the liquid crystal sample in the liquid crystal cell by using a signal generator, the voltage is gradually increased from 〇v to 1 〇v; and providing a control interface to the photodetector for recording the photodetector acquisition The penetration and mode, the control interface includes a software for calculating the birefringence from the pattern formed by the penetration. The method of claim 24, further comprising: amplifying the connection with the photodetector and the control interface, wherein the transmittance of the photodetector is amplified by the amplifier and then providing a control interface . The method of claim 24, further comprising a temperature controller coupled to the liquid crystal cell and the control interface for controlling the liquid crystal in the liquid crystal cell to maintain a constant temperature. = The method of claim 24, wherein the signal is coupled to the control interface such that the voltage generated by the signal crystal is regulated by the control interface. The method comprises the steps of: measuring a rotational viscosity of the liquid crystal sample by placing a crystal sample in a liquid crystal cell; and placing the first polarizer and the second polarizer on opposite sides of the liquid crystal | The polarizer and the second polarizer are orthogonal; 35 200804568 passing a laser beam through the first polarizer, the liquid crystal cell and the first Just after the first polarizer and/or the second polarizer are used to detect the polarizer, the transmittance measured by adjusting the first device is minimized; the Xiang-signal generator applies a voltage to the liquid crystal in the liquid crystal cell. In the daily sample, the voltage is gradually increased from ov to 1〇v; and n, # supply-control interface is connected with the photodetector to record the penetration and waveform acquired by the first detector, the foregoing control interface The inclusion body is used to form a pattern formed by the penetration degree; defining the aforementioned voltage tearing to increase the penetration degree formed by the gift. The difference between the signal peak and the value of the first signal valley is the Vpack, the control signal The liquid crystal sample applied to the liquid crystal cell by the generator is described as a vapp丨 voltage; after a suitable time is stabilized, the voltage is released to 〇v, and the waveform obtained by the photodetector is taken; and the surface control interface is used. The software is calculated as 71/K11, and the value of the rotational viscosity (r 1 ) is obtained by knowing the K11 value. The method of claim 28, further comprising an amplifier and the photodetector and Control interface connection, photodetector The transparency signal is amplified by the amplifier and then provided with a control interface. 30. The method of claim 28, further comprising a temperature controller connected to the liquid crystal cell and the control interface for controlling the liquid crystal The liquid crystal in the box is kept at a constant temperature. The method of claim 28, wherein the signal 36 200804568 generator is coupled to the control interface such that the voltage generated by the signal generator in the liquid crystal cell is regulated by the control interface. " 32.- Measuring the birefringence and/or rotation of the liquid crystal sample, which comprises: 'degree I laser source for providing the desired beam; for a liquid crystal cell, which is located in the foregoing a beam path of the laser source and a liquid crystal sample to be measured; < a second first polarizing plate and a second polarizing plate, which are respectively before and after the liquid crystal cell on the beam path of the source, wherein the first The above-mentioned lightning deflection is carried out in the in::^·# light 4 and the second polarizing plate is orthogonal; a light detector is used to detect the light beam penetrating the box and the second polarizing plate. Transparency and wave shape; The signal generator is provided with a control interface of the liquid crystal panel of the electro-optical polarizer provided in the foregoing liquid crystal cell, which is connected with the photodetector and detects the penetration degree by the p detector. a graphic, the control interface includes a pattern formed by the light-receiving for recording the transmittance of the photodetector, and a second-softness ratio. The leaf-specific birefringence 33 is as described in claim 32. The optical amplifier and the control interface are coupled to the optical detector and the control interface, and the optically enhanced penetration signal is amplified by the amplifier to provide a control interface. The instrument 34 is as described in claim 32, The system can be connected to the liquid crystal cell and the control interface, and the liquid crystal in the liquid crystal cell is further kept at a constant temperature. For control 35. The device described in claim 32, wherein the first 37 200804568 generator is coupled to the control interface such that the voltage generated by the signal generator in the liquid crystal cell is regulated by the control interface. 38