TW200825158A - Additive for liquid crystal having high helical twisting power, synthesis method thereof and a liquid crystal composition containing the additive - Google Patents

Abstract

The invention relates to an additive for liquid crystal having high helical twisting power (HTP). The structure of the additive is an organic polycyclic ester with chiral activity, which can be prepared by reacting isosorbide with various organic acids via esterification. Furthermore, the additional chiral center on organic acid moiety can modulate the HTP value of liquid crystal. The additives are highly soluble in nematic liquid crystal (host), and liquid crystal compositions containing the additives can obtain higher HTP and good light stability.

Description

200825158 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD The present invention relates to a liquid crystal additive having a high helical twisting force, particularly relating to an optically active polycyclic organic ester compound having an additional pair of palms. The center, when added to the liquid crystal, can regulate the helical twisting force (HTP) of the liquid crystal. ^ [Prior Art] Cholesteric liquid crystal can reflect light waves of a specific wavelength, especially with the same pair of palm-shaped circular apolar rays with wavelengths close to their pitch length P, and let the other direction The characteristics of the palm-shaped circular aurora passing. According to the Bragg reflection rule, the reflection center wavelength λ of the cholesteric liquid crystal, the average refractive index nave of the film, and the pitch P of the cholesteric liquid crystal arrangement have the following relationship:

_ λ 2 nave X P ΔXCreflection bandwidth) is related to the optical anisotropy of the film, or birefringence, and the pitch p. The relationship is as follows:

Δλ = Δη X P That is, the reflection wavelength is related to the pitch ρ of the liquid crystal molecules and the optical anisotropy Δη. The cholesteric liquid crystal mentioned in the present invention is a mixture of optically active optically active molecules and non-optically active nematic liquid crystal formulations, and has a pitch of 0949-A21841TWF (N2); P54950038TW; kelly 6 200825158 The ratio of active molecules to non-optically active nematic liquid crystal formulations is controlled. The relationship between the pitch of the molecule (Pitch, P) and the addition of 7-degrees of optically active molecules and Helical Twisting Power (HTP) is as follows:

HTPxC = 1/P where P is the pitch of the cholesteric liquid crystal molecule, C is the weight percent concentration of the optically active molecule added to the liquid crystal, and HTP is the helical twisting force, which indicates the ability of the optically active molecule to rotate the liquid crystal molecules. At a specific pitch _ requirement, the higher the HTP value, the lower the concentration of optically active molecules that need to be added. German liquid crystal expert H.-G· Kuball proposed the height of the helical torsion force in 1995 (J. Mai. CAem 1995, 5, 2167), and the type of optically active functional group, the intramolecular pair of palm centers (chiral The number of centers and the specfic rotation are related. In addition to the optically active optical rotation and the greater the number of palm centers, the greater the helical torsion force is, the addition of cyclic functional groups in the molecule and asymmetry to change its conformation. It also causes the optically active liquid crystal molecules to produce a larger helical twisting force. On the other hand, due to the special helical structure of the optically active high helical twisting liquid crystal molecules, when this optically active liquid crystal molecule is added to the liquid crystal formulation, due to the special helical structure of the optically active liquid crystal molecules, especially when the optical activity is high, the helical twist When the weight percentage of the liquid crystal molecules is gradually increased (for example, when it is more than 10% by weight), if the solubility of the liquid crystal precursor (multilayer nematic liquid crystal) for the optically active liquid crystal molecules is not good, when the cholesteric liquid crystal composition is formulated, The weight percent concentration is limited by the configuration of the optically active high snail 949-A21841TWF (N2); P54950038TW; kelly 7 200825158 spirometry liquid crystal molecules. Therefore, how to develop a liquid crystal additive having a higher helical twisting force and maintaining a good solubility when added to a liquid crystal has been an important subject of liquid crystal research. SUMMARY OF THE INVENTION In view of the above, an object of the present invention is to develop a liquid crystal additive having a high helical twisting force, which uses a liquid crystal additive having a high helical twisting force to add H to a liquid crystal, and the liquid crystal is composed by controlling the addition ratio. The object reflects a specific wavelength. In order to achieve the above object, the present invention provides a liquid crystal additive having a high helical twisting force, which has a structure of an optically active polycyclic organic ester compound represented by the formula (I), and a formula (I)

In the compound of the formula (I), B and B' are each independently one or more cycloalkyl groups, heterocyclic groups, aromatic ring groups or aromatic heterocyclic groups, and one or more of them are of any ring structure. Hydrogen may be substituted by a halogen atom; A and A' are each independently one or more hydrogen, halogen, alkyl, sulfanyl, alkoxy, which are attached to any position on B or B', wherein An alkyl group, a sulfanyl group or an alkoxy group having 1 to 10 carbon atoms, which is linear or branched, and wherein one or more hydrogen atoms may be substituted by a halogen atom; X and X' are each a separate linking group which is a single bond, CH2, CF2, C2H4, CO, 0949-A21841TWF (N2); P54950038TW; keliy 8 200825158 CNd), CH=CH or CC reference, wherein & contains 1-4 One carbon atom, which is linear or branched; Y* is an optically active center of the palm, which is a carbon atom with or or S configuration, Y* = CZZ', where Z and Z 'separate from each other selected from the group consisting of hydrogen, halogen, alkyl, sulfanyl or alkoxy, and wherein the alkyl, sulfanyl or alkoxy group contains from 1 to 10 Atom, a linear or based branched persons. Further, the present invention further provides a method for producing a liquid crystal additive having a high helical twisting force, which comprises subjecting isosorbide to two organic acid compounds represented by Formula 10 (II) and Formula (III). Esterification reaction to form a liquid crystal additive of the above formula (I), formula (Π) 〇 (III) 〇

H〇-C~B -A • In the formulae (II) and (III), the definitions of A, A, B, B, and Y* are as described above. To achieve the above object, the present invention further provides a liquid crystal composition comprising: (a) 3 to 30% by weight of a liquid crystal additive having a high helical twisting force as described above; and (b) 3 to 97% by weight of a liquid crystal, It is different from component (a). In order to make the above objects, features, and advantages of the present invention more comprehensible, the following detailed description will be made with reference to the accompanying drawings: 0949-A21841TWF(N2); P54950038TW; kelly 9 200825158 [Embodiment] a high helical twisting liquid crystal additive having the structure of an optically active polycyclic organic ester compound represented by formula (I), formula (1)

In the compound of the formula (I), B and B' are each independently one or more of a cycloalkyl group, a heterocyclic group, an aromatic ring group or an aromatic heterocyclic group, and one or more of the ring structures are arbitrary. The hydrogen may be substituted by a halogen atom; A and A' are each independently one or more hydrogen, halogen, alkyl, sulfanyl, alkoxy, which is attached to any position on B or B'. Wherein the alkyl group, the sulfanyl group or the alkoxy group has 1 to 10 carbon atoms and is linear or branched, and one or more of the hydrogen atoms may be substituted by a halogen atom; X and X are Separate linking groups, which are single bonds, CH2, CF2, C2H4, CO, CN(Ri), CH=CH or CC, wherein & contains 1-4 carbon atoms, * is linear Or a branched person; Y* is an optically active pair of palm centers, which is a carbon atom having an AND or S configuration structure, Y* = CZZ', wherein the Z and Z' systems are each independently selected from the following Functional groups: hydrogen, halogen, alkyl, sulfanyl or alkoxy, and wherein the alkyl, sulfanyl or alkoxy group contains from 1 to 10 carbon atoms and is linear or branched. The above B and B5 may each independently be selected from the following functional groups: 0949-A21841TWF (N2); P54950038TW; kelly 10 200825158

In the compound of the above formula (1), hydrazine and x are preferably c 〇; γ* is a carbon atom having a sorrow structure or a group S, and the ruthenium and osmium attached thereto are preferably hydrogen, a burnt group or a burnt oxygen. The ruthenium and osmium are preferably each independently _(tetra)a plurality of aromatic ring groups; ruthenium and osmium are preferably each independently one or more nitrogen or alkoxy groups. In a preferred embodiment, the present invention has a liquid helix additive having a high helical twisting force which is an optically active n and oxime compound as listed below:

II

〇c6h13

MeO

The liquid crystal with high helical twisting force of the invention is added to the design of the molecular structure, and the optical activity 949-A21841TWF(N2) containing two pairs of palm centers is used on the mouth and mouth of the mouth; P54950038TW; kelly 200825158 The bis-pentaphenoxy moiety is centered, plus a pair of asymmetric mesogenic groups, one of which has an additional pair of palm centers on the liquid crystal group, with this additional pair of palms The center may have a positive or negative influence on the HTP value of the liquid crystal composition, such that the HTP value increases or decreases. The above method for producing a liquid crystal additive having a high helical twisting force comprises the two-step esterification of isosorbide with two organic acid compounds represented by the formula (Π) and the formula (ΠΙ) Forming a liquid crystal additive of the above formula (I), • Formula (II) 〇HO - 0 - Y* - B, A, Formula (III) 〇

HO-C-B - A In the formulae (II) and (III), the definitions of A, A, B, B' and Y* are as described above and their preferred modes are as described above. The reaction formula of the above two-step esterification reaction is as follows:

For example, the method can firstly react isosorbide with 4-n-hexyloxybenzoic acid to obtain an intermediate product 0949-A21841 TWF(N2); P54950O38TW; kelly 12 200825158

Ml : 2-0-[4-(hexyloxy)benzoate]-1,4:3,6-dianhydro-D-sorbitol (2-0-[4-(hexyloxy) benzoate]- l, 4:3,6, dianhydro _D-glucitol), and then the intermediate product M1 and 〇S>2-(6·曱oxy-2-naphthyl)propionic acid (GS^je-Methoxyd-naplithyl) proponic Acid) and (i?)-methoxyphenylacetic acid ((i?)-Methoxyphenylacetic acid), respectively, to produce optically active polycyclic organic ester compounds such as II and 12, all of which are reactive The reaction formula is as follows:

In the above steps of synthesizing the intermediate product M1, the liquid crystal additives II, 12, the reaction temperature and the reaction time are 30 minutes in an ice bath, and further reacted at room temperature (about 25 ° C) for 12 hours or more. The yield of Ml, II, and 12 was about 33 to 43%. The method for producing a liquid crystal additive of the present invention is characterized in that two organic acids having a liquid crystal molecular structure and an optically active isosorbide are esterified in two steps by a simple synthesis step to obtain a formula The compound of (I) has the advantages that the synthesis process is easy to control, the reactivity is high, and the product 0949-A21841TWF(N2); P54950038TW; kelly 13 200825158 is easy to purify, and the isosorbide used is inexpensive, and is used for manufacturing high. The spiral twisting liquid crystal additive is very economically competitive, and when used in combination with other liquid crystals, a new liquid crystal composition can be developed. The liquid crystal composition of the present invention comprises: (a) 3 to 30% by weight of a liquid crystal additive having a high helical twisting force as in the above formula (I), that is, comprising at least one optical such as ruthenium or 12 An active polycyclic organic ester compound; and (b) 3 to 97% by weight of a liquid crystal host different from the component (a) 10, wherein the liquid crystal additive is preferably added in an amount of 5 to 20% by weight, The liquid crystal precursor may be a Nematic liquid crystal, a smectic liquid crystal, or a discotic liquid crystal. The liquid crystal composition of the present invention not only has a high helical twisting force, but also can control the pentatholic energy of the liquid crystal composition by adjusting the ratio of addition of the liquid crystal additive to a cholesteric liquid crystal formulation having different reflection wavelengths. In addition, since the structure of the liquid crystal additive of the present invention contains an additional center of the palm, the ® can regulate the HTP value of the liquid crystal composition to progress in the positive or negative direction, and therefore the liquid crystal composition of the present invention has an HTP range of about 9 Between ~58 μ · πΤ1. In addition, the liquid crystal composition of the present invention has low temperature dependency and high photostability, and has a lower viscosity than a liquid crystal additive generally used, and is about 33 to 36 cps, and can be used as a liquid crystal component required for a liquid crystal display. One of them is suitable for making liquid crystal display devices, especially for twisted nematic (TN) displays, super twisted nematic (STN) displays, color super twisted nematic (CSTN) displays, and thin film transistors. (TFT) display. The present invention is a liquid crystal composition having a high helical twisting liquid crystal additive, and can also be used for producing a reflective polarizing plate, a cholesteric reflective polarizing plate, a reflecting plate, and an optical device. Compensation film, retardation film, color filter or liquid crystal dye. The synthesis steps of the formula (1) having the high helical twist liquid crystal additives II and 12, and the method of the helical twist τ and related test results are described in detail below.卞力_Test Pitch and spiral torsion test method:

The present invention uses Olympus MXSO optical polarization i! a few pitches. The measurement method is to mix the new optically active compound of our synthesis into the organic matrix host ZLI-1132 of Merck Company at a concentration of 1 wt%, and raise the temperature to make the supplied phthalocyanate by capillary action. After setting the unit scale length of the microscope, remove the Lu 1 function cut) - > Scale the inside of the LCD box, measure the pitch and use the standard scale

(0.01mm) placed on the microscope stage through the eyepiece to focus, Ling, ruler liquid crystal defect line between the distance, you can get the pitch. It is possible to change the value obtained three times and then average the average pitch. Through the upper block I> green view, the pitch value is substituted into the HTP-^Pxc)·1, and the converted 矸~ 夕 green is obtained. [Example 1] Synthesis of intermediate M1 : 2-0-[4-(hexyloxy) | p 1,4:3,6-dianhydro-D-sorbitol (2-0-[4-(hexyl) 〇xy) u ^ 酉 ]] l,4:3,6-dianhydro -D- glucitol) 〇ate]

0949-A21841 TWF(N2) ; P54950O38TW; kelly 15 200825158 Take 10 g (68 mmol) of isosorbide and 15:2 g (67 mmol) of 4-n-hexyloxybenzoic acid Dissolve in 150 ml of CHbCU, then add 4-dimethylaminopyridine ('(dimethyl amino)-pyridine, DMAP) and stir for one minute in an ice bath, then dissolve in N, N, - dicyclohexyl group of CH2C12 The carbodiimide (N, Nf-Dicyclohexylcarbodimide, DCC) was dropped into the reaction flask, and the mixture was stirred in an ice bath for 0.5 hour, then the ice water bath was removed, and the mixture was further stirred at room temperature for 12 hours or more. After completion of the reaction, extraction was carried out by using cH2C12/CH3COOH, and the CI(Cl2) layer was collected and washed with 1N HCl (aq). The organic layer was dried, filtered, and the solvent was evaporated to give a crude product. The crude product was purified by ethyl acetate to recrystallize several times to obtain a white solid product M1, yield 43% 〇 [Example 2] Liquid crystal additive of helical twisting force: 2-0-[4-(hexyloxy)benzoate]-1,4:3,6-dihydro-5-0-[〇S>2-( 6-decyloxy-2-naphthyl) ugly]oxy D-sorbitol (2-0-[4-(hexyloxy) benzoate]-l?4:396-dianhydro-5-0-[(5f )-2-(6-Methoxy-2-napht hyl) propanoyl]〇xy D-glucitol)

2 g (5·7 mmol) of the intermediate M1 synthesized in Example 1 and 1.57 g (6·8 mmol) of hydrazine S> 2-(6-decyloxy-2-naphthyl)propionic acid ((^) ^-(G-MethoxyJ-naphthyl) proponic acid) is dissolved in 50 ml 0949-A21841TWF (N2); P54950038TW; kelly 16 200825158 CH2Cl2, first stirred with 4-(dimethylamino)-pyridine (DMAP) for one minute in an ice bath Then, 1.39 g of N, N'-Dicyclohexylcarbodimide (DCC) CH2C12 solution was dropped into the reaction flask, and the mixture was stirred for 0.5 hour in an ice bath, then the ice water bath was removed, and stirring was continued for 12 hours or more at room temperature. The filtrate was taken out and extracted with CH3COOH /H20. The CH2C12 layer was collected and washed with saturated brine. The organic layer was dried, filtered and evaporated to give a crude product, which was purified by column chromatography. Product II, the yield was 40%. The synthesized product II was measured by nuclear magnetic resonance spectrometry NMR, and its spectrum is shown in Fig. 1. The Olympus MX50 optical polarizing microscope was used to measure by the above-mentioned pitch measurement method. The pitch value (p) obtained is ι〇·99 μηι, which will be as described above. The pitch value obtained in the step is substituted into the formula htP = (Pxc)·1, and the helical torsion force ΗΤΡ=9·09 μητ1 can be obtained. [Example 3] Synthesis of liquid crystal additive having high helical twisting force 12: 2-0 -[4-(hexyloxy)benzoate]-1,4:3,6-dianhydro-5-0-[(i?)-decyloxyphenylethyl]oxy D- Sorbitol (2-〇-[4-(hexyloxy) benzoate]-! 54:356-dianhydro- 5-0- [(i?)-Methoxyphenyl acetyljoxy D-glucitol)

0949-A21841TWF(N2); P54950038TW; kelly 17 200825158 501 mg (1.43 mmol) of the intermediate product M1 synthesized in Example 1 and 260 mg (1.71 mmol) of (and)-decyloxyphenylacetic acid ((i? -Methoxyplienyl acetic acid) is dissolved in 20 ml of CH2C12, first added with 30 mg of 4-(dimethylamino)-pyridine (DMAP) and stirred for one minute in an ice bath, followed by 340 mg of N,N'-Dicyclohexylcarbodimide (DCC) The CH2C12 solution was dropped into the reaction flask, and the mixture was stirred under an ice bath for 0.5 hour, then the ice water bath was removed, and stirring was continued at room temperature for 12 hours or more. The filtrate was taken out by filtration and extracted with CH3COOH /H20. The CH2C12 layer was collected and washed with saturated brine. The organic layer was dried and filtered to remove the solvent to obtain crude product which was purified by column chromatography. The yield was 33%. The synthesized product 12 was measured by nuclear magnetic resonance spectrometry NMR, and its spectrum is shown in Fig. 2. Using an Olympus MX50 optical polarizing microscope and measuring by the pitch measurement method described above, the obtained pitch length (P) was 1.71 / xm, and the pitch value obtained in the above step was substituted into the formula HTP = (Pxc)_1. , the helical torsion force HTP = 58.4/mf1 can be obtained. _ [Comparative Examples 1 to 5] Comparative Example 1 is a common liquid crystal additive produced by Aldrich, and its molecular structure is as follows:

CM Comparative Example 2 is a common liquid crystal additive produced by Merck, and its molecular structure is as follows:

〇〇6Ηΐ3 0949-Α21841 TWF(N2) ;P54950038TW;kelly 18 200825158 Comparative Examples 3 to 5 are liquid crystal additives synthesized by ITRI Chemicals Co., Ltd., whose molecular structures are as follows:

Comparative Example 3 Comparative Example 4

Comparative Example 5 MeO

The liquid crystal additives of the above Comparative Examples 1 to 5 were measured by the above-described pitch measurement method, and the results of the comparison of the obtained helical torsion force HTP value with the HTP value of the examples are shown in Table 1 below, and in Table 1 Other characteristics of the compounds of the examples and comparative examples, such as the molecular weight Μ, the melting point Tm, the crystallization temperature Tc, and the viscosity values thereof at 20 ° C in the liquid crystal precursor 5100-100 (available from Merck) are also listed. 0949-A21841TWF(N2); P54950038TW; keliy 200825158 Table 1 Comparison of compound characteristics of the examples and comparative examples Temple terms: M (g/mol) Tm (°C) Tc (°C) HTPC/zm'1) Viscosity comparison Example 1 249 4 4 7 to 9 43 Comparative Example 2 454 48 48 -11 57 Comparative Example 3 414 100 51 40 Comparative Example 4 554 72 91 51 41 Comparative Example 5 484 32 94 53 33 Example 2 562 46 97 9 36 Implementation Example 3 498 35 93 58 33

As can be seen from Table 1, in Examples 2 and 3 of the present invention, compared with Comparative Examples 1 and 2, the HTP value was centered because the molecular structure contained two bis-pentacyclic moieties centered on the palm center. Significantly increased a lot. Further, in the first embodiment of the present invention, in comparison with Comparative Examples 3 to 5, since the molecular structure contains an additional liquid crystal group centered on the palm, the influence of the center of the palm and the other palm center on the HTP is mutually Offset, therefore, the effect on HTP as a whole has a negative effect, so that the HTP value of the liquid crystal composition of Example 2 is significantly reduced. On the other hand, the additional center of the palm contained in the molecular structure of Example 3 has a positive effect on the influence of other palm center on HTP, so that the HTP value of the liquid crystal composition of Example 3 is increased. Further, the viscosity values of Examples 2 and 3 were significantly lower than those of Comparative Examples 1 to 4, and were comparable to those of Comparative Example 5. Because the liquid crystal formula is sticky 0949-A21841TWF(N2); P54950038TW; kelty 20 200825158 is high, the response time is lengthened, so the display shows slow reaction speed. Generally, the lower the viscosity of the liquid crystal formulation, the lower the viscosity. Therefore, the liquid crystal additive of the present invention can meet the requirement of low viscosity in addition to the requirement of high HTP value. [Example 4] Example 4 is a liquid crystal composition in which liquid crystal additives 11 of different ratios were added, wherein a liquid crystal host was 5100-100 (available from Merck), and the relevant physical properties were: at 25 °C. Viscosity η25=27 cps, birefringence Xinyi η=0·195, driving voltage Vth=1.8, dielectric anisotropy Δε=7·ΐ2, clearing point temperature Tc=70.4° C., melting point Tm=-21.6°C. First, the liquid crystal additive II was added to the liquid crystal precursor at 2% by weight (the liquid crystal precursor was 327.0 mg, and the additive II was 6.2 mg) to form a cholesteric liquid crystal formulation, which was a reflection type ultraviolet-visible (UV-Vis) spectrometer. The measurement can obtain the reflection wave width (Δλ)=63·7ηπι, the reflection wavelength (λ)=584 nm, and then change the addition ratio of the liquid crystal additive 3 to 3 weight% (the liquid 10 crystal matrix is 3〇3.:5mg5 added When the substance II is 9.4 mg), the reflection wave width (^) = 69.311111 can be measured, and the reflection wavelength (again) is slightly blue shifted to 564 nm. From the above results, it can be known that liquid crystal additives of different addition ratios are known. Since the reflection wavelength of the liquid crystal composition is affected, the performance of the liquid crystal composition can be controlled by the ratio of addition of the liquid crystal additive. Although in the embodiment, a liquid crystal additive of 2 to 3 weight percent is taken as an example, those skilled in the art can understand that the HTP value of the additive is 0949-A21841TWF(N2); P54950038TW; kelly 200825158 for a specific liquid crystal. For fixing, it can be known from the formula HTPxC=l/Ρ that when the addition ratio C of the liquid crystal additive is changed, the pitch P of the liquid crystal composition changes accordingly, and the above formula λ = nave XP and Αλ = An XP It can be seen that when the pitch P is changed, the reflection wavelength λ and the reflection wavelength Αλ of the liquid crystal composition also change. In general, the liquid crystal additive may be added in an amount of from 3 to 30% by weight, preferably from 5 to 20% by weight, depending on the desired reflection wavelength of the liquid crystal composition and the enthalpy of the liquid crystal additive. Although the present invention has been disclosed in its preferred embodiments, it is not intended to limit the invention, and the invention may be modified and modified without departing from the spirit and scope of the invention. The scope of protection is subject to the definition of the scope of the patent application.

[0091] A. Fig. 2 is a spectrum chart of the liquid crystal additive 12 synthesized in accordance with Example 3 of the present invention as measured by NMR. [Main component symbol description] 4th 〇 0949-A21841TWF{N2); P54950038TW; ketly 23

Claims (1)

200825158 X. Patent application scope: 1. A liquid crystal additive having high helical twisting force, which is an optically active polycyclic organic ester compound represented by formula (I), formula (I) Wherein B and BM are each independently one or more cycloalkyl, heterocyclyl, aromatic cyclic or aromatic heterocyclic groups, and hydrogen in one or more ring atoms may be substituted by a halogen atom; And A' are each independently one or more hydrogen, halogen, alkyl, sulfanyl, alkoxy, which is attached to any position on B or B', wherein alkyl, sulfanyl or alkoxy The group contains 1-10 carbon atoms, which are linear or branched, and one or more of the ruthenium atoms may be substituted by a dentate atom; X and X' are independent linking groups, Is a single bond, CH2, CF2, C2H4, CO, CNd), CH=CH or CC parameter, where I contains 1-4 carbon atoms, which are linear or branched; Y* is optical The center of activity is the carbon atom with and or S configuration, Y* = CZZ', wherein Z and Z' are each independently selected from the following functional groups: hydrazine, halogen, alkyl, sulfane Or alkoxy, and wherein the alkyl, sulfanyl or alkoxy group has from 1 to 10 carbon atoms, which is straight or branched. 2. The liquid crystal additive having high helical twisting force as described in claim 1, wherein B and B' are each independently selected from the group consisting of: 0949-A21841TWF (N2); P54950038TW; kelly 24 200825158 A liquid crystal additive having a high helical twisting force as described in Item 1 and wherein η is equal to 3, as in the patent specification Φ, wherein X and X are (7). Liquid: Add as ώ and hydrazine to ammonia, alkyl or alkoxy. .D apply for the liquid crystal additive in the scope of the patent, in the case of A, /, and the snail twisting ring. /, in the independent of one or more aromatics 6. If the scope of patent application is i = additive 'where ... are independent of each other: = hydrogen transfer power 7. As stated in the special township section A liquid crystal additive having a high helix, wherein the molecular structure of the formula (1) is as follows: 'force Me〇 OCgH 13 , 8. The high-spiral liquid crystal additive according to the above-mentioned patent, wherein the molecular structure of the formula (I) is as follows: · 0949-A21841TWF (N2); P54950038TW; kelly 25 200825158 Me〇 9. A method of producing a liquid crystal additive having a high helical twisting force, comprising: esterifying isosorbide with two organic acid compounds represented by formula (II) and formula (III) to form The liquid crystal additive having the high helical twisting force of the formula (I) described in the first paragraph of the patent application, formula (II) • 9 HO-ί - a, formula (III) 〇 HO~CB - A wherein B and B ' is one or more cycloalkyl, heterocyclic, aromatic or heterocyclic groups independently of one another, and one or more of the hydrogens on the ring atom may be replaced by a halogen atom; Φ A and A Each of which is independently one or more hydrogen, halogen, thiol, sulfanyl, alkoxy, which is attached to any position on B or ugly, wherein the alkyl, thiol or alkoxy group contains M〇 One carbon atom, which is linear or branched, and one or more of the hydrogen atoms may be replaced by a γ atom; Y* is an optically active pair of palm centers, and the system has a $ or S group The carbon atom of the structure, Y* = CZZ, wherein ζ and ζ are independently selected from the following functional groups: hydrogen, hydroxyl, Group, a sulfur group S group or appearance, and wherein alkyl, thioalkyl or alkoxy group containing carbon atoms, based linear or branched persons. 0949-Α21841 TWF(N2); P54950038TW; kelly 26 200825158 10. The method of liquid crystal additive according to the ninth application of the patent application scope, love ^ 崄 /, directional spiral twist base. 〃 与 2 2 2 2 2 2 2 2 2 2 2 2 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如 如Selected from # And where η is equal to Turning force = 1 = a method of producing a high liquid daily excipient as described in item 9, wherein 3 and 3 or more aromatic ring groups are used. Feng Kou from an independent 13 · As described in the scope of claim 9 of the patent application, the liquid crystal additive of the semi-finished 冋 Α 或 or a plurality of hydrogen, 妓 去 Α Α Α Α Α 为The independent production of a light force 14 wide application = the scope of the goods mentioned in item 9 has the 峨 ^ 己心乳 base formic acid (4_n_hexyk) xybe &化 & butterfly. The material of the 15 Guangshen, Fan Wei 9th The method for producing a daily additive containing a liquid such as a liquid organic compound is 0949-A21841 TWF(N2); P54950038TW; kel|y 27 200825158 (6)-2-(6-decyloxy_2_naphthyl a method for producing a liquid crystal additive having a high helical twisting force as described in claim 9 of the patent application, wherein the formula (N) is a method of producing a liquid crystal additive having a high helical twisting force. The organic acid compound of (II) is (i)-Methoxyphenyl acetic acid. 17. A liquid crystal composition comprising: (a) 3 to 30% by weight as an application a liquid crystal additive having a high helical twisting force as recited in claim 1; and 41 (b) 3 to 97 weight percent liquid crystal, (a) The liquid crystal composition according to claim 17, wherein the liquid crystal additive having a high helical twisting force accounts for 5 to 20% by weight of the liquid crystal composition. The liquid crystal composition of the liquid crystal composition according to Item 17 of the present invention, wherein the liquid crystal composition is in the range of 9 to 58 μ. Nematic liquid crystal, smectic liquid crystal, discotic liquid crystal. 21. The liquid crystal composition according to claim π, which is used as a reflective polarizing plate and a reflecting plate. The liquid crystal composition of the optical compensation film, the retardation film, the color filter, the liquid crystal dye, or the liquid crystal display. The liquid crystal composition according to claim 21, wherein the reflective polarizing plate is a cholesterol type reflective type. Polarizer 0949-A21841TWF(N2); P54950038TW; kelly 28