TW201226540A - Chiral compound with isosorbide moiety and chiral composition and blue phase liquid christal composition thereof - Google Patents

Abstract

A blue phase liquid crystal composition includes a reactive monomer, a photo initiator, a blue phase liquid crystal material and a chiral dopant. The chiral dopant has the following general structure of formula (I): wherein, C1 and C2 are independently a soft linking group with 1-14 carbons; Ar1, Ar2, Ar3, Ar4 are independently a cyclic linking group; G1, G2, G3 and G4 are independently and respectively a monovalent moiety of Ar1, Ar2, Ar3 and Ar4; m and x are not 0 at the same time and n and y are not 0 at the same time; p, q, r and s are positive integers; B1, B2, B3, B4, B5 and B6 are independently a divalent linking group; and A is a soft linking group with 1-14 carbons.

Description

201226540 VI. Description of the Invention: [Technical Leadership of the Invention] The present invention relates generally to an optically active compound and composition having an isosorbide group. Specifically, the present invention relates to an optically active compound having a plurality of isosorbide groups and an optically active oligomer thereof, and a blue phase liquid crystal composition containing the optically active compound. The present invention uses an optically active compound having a plurality of isosorbide groups to induce blue phase properties of the blue phase liquid crystal composition containing the optically active compound, thereby obtaining a wider blue phase liquid crystal temperature range and lower Drive voltage, but with advantages in production, manufacturing and product characteristics. [Prior Art] The blue phase or BP liquid crystal is a self-aggregating three-dimensional photonic crystal structure. This liquid crystal phase usually occurs between the isotropic phase (isG nostalgia) and the cholesterol phase (eholeste-). The blue phase liquid crystal molecular layer and the layer stack are arranged in a columnar shape. The molecular arrangement behavior is relatively special. As can be seen from the scientific research published by nearly two pounds, for example, ChemistryLetter, 2008, 12 1242 'reading liquid crystal molecules extend from the vertical alignment of the central spindle molecules and extend them outwardly and the molecules that extend outward will be spirally twisted until The outermost 45 degrees. & m' is rotated around four to form a cylindrical (Cyllnder) arrangement with a cylindrical diameter of 1/4 pitch (pitch/4, or 201226540.P/4), and such an 8] board will also Stacked in different ways to form a self-interlaced arrangement. Lattice defects occur in the staggered junctions in ®(4). Such lattice defect points form a cubic_stack arrangement, which can be divided into blue phase, blue phase (II), and blue phase (III). Lattice arrangement. They are center cubic, simple cubic, and iso-like. However, no matter which kind of blue phase liquid crystal is used, since it is arranged in an isotropic direction, the lattice orientation in any direction is uniform, and therefore it can also be regarded as a liquid crystal phase which is similar to the uniform phase. Since the wavelength of light generated by the diffraction of the molecular lattice through Bragg is usually biased to short-wave, the blue-phase texture map observed by a polarizing microscope can be found that the mosaic texture map whose appearance is mostly blue or blue-violet color is therefore Named after. The blue phase liquid crystal material is most praised (four) because the reaction speed under the action of the electric field is particularly fast in the blue phase condition. The blue phase liquid crystal display is a liquid crystal display with an off state in the dark state. It is pointed out in the literature that the positive blue phase liquid helium must be induced by a transverse electric field generated by an electrode similar to an IPS (in, plane swhch) liquid crystal display. The change of refractive index (Δ n, p〇siUve) (Δη′, and then the change of bright and dark state. In the giant view, the positive blue phase liquid crystal is bright under the applied electric field. The blue phase liquid crystal material is made of The liquid crystal display has an ultra-high fast response, which is characterized by 'the fastest even reaching the level of hundreds of microseconds. In the early days, the blue phase liquid crystal exhibited a blue phase temperature range that was too narrow, for example only Bu 2. 匸, 疋 疋 blue The major disadvantages of liquid crystal materials in application. However, in recent years, the 201226540 study found that it is possible to illuminate in the temperature range of the blue phase by blending different proportions of reactive monomers (Nature materials, 2002, 1 , 64) 'Draw the blue phase temperature to a few tens of degrees (>6〇〇c), and therefore theoretically temporarily solve the problem that the blue phase temperature of the blue phase liquid crystal material is too narrow. Isosorbide Isosorbide is a dipentacyclic molecule containing dioxins. As shown in Figure 1, although the molecular derivative of isosorbide as the optical center has four optical centers in the knive structure, it can be used as optical rotation. The doping is induced to produce a blue phase, but the steric barrier of the isosorbide group is too large, and its liquid crystal properties are not obvious. Therefore, when it is used as an optically active dopant, it is easy to cause the original liquid crystal phase to be destroyed, so it is not suitable. In other respects, the use of isosorbide vinegar in blue phase liquid crystal materials also has problems such as excessive driving voltage. Some known isosorbide s derivatives are exemplified in US Patent No. 744〇l60B2. These isosorbide derivatives do not have any liquid crystal phase per se. Although it can induce a blue phase liquid crystal after being mixed with a liquid crystal having a nematic phase, it has disadvantages such as excessive driving voltage. For example, even if this is successfully induced Blue phase liquid crystal, but the driving voltage is increased to 17〇v, but the saturation voltage is still not seen. Therefore, the application of the blue phase liquid crystal material still has the disadvantage of requiring high driving power. How to reduce the driving voltage of the blue phase liquid crystal display becomes another important point that needs to be overcome. SUMMARY OF THE INVENTION The composition of the blue phase liquid crystal usually has the main liquid crystal (h〇stLC) and the cyclo 201226540 lightral dopant. And with the doping of the polymerized monomer, forming a blue phase liquid crystal system containing the polymerized monomer and the polymerizable monomer. For the molecular composition, the optical center containing additive is an important factor affecting the photoelectric characteristics of the blue phase liquid crystal. The more the number of optical centers contained in the molecular structure of the mono-optic center, the more the optically active substance can induce the blue phase, but the addition of too many or too few optically active center molecules leads to the cholesterol phase (chlral _atie). Phase ). The present invention thus designs a structure containing a plurality of optically active centers as an optically active dopant. The present invention is based on the Prophet: an optically active compound having a diisosorbide vinegar group as an optically active dopant, thereby providing a plurality of optically active centers to induce the li phase. The optically active compound of the present invention has the structural formula (I) shown below:

In the structural formula (I): C, and C2 are each independently a soft chain containing 1 to 14 carbons.

Ar! Ar2 Ar3 and Ar4 are cyclic linkages (cycliclinking gr〇up), G! G2 G3 and & are monovalent substituents of Αι>ι, ΑΓ2, Αγ3 and 八1*4, respectively. 〇, η, y are not 〇 at the same time, P, q, r, s are integers, 201226540

Bi, B2, B3, B4, B5, and B6 are each independently a divalent linking group, and A is a soft chain linking group containing 1 to 14 carbons. In one embodiment of the invention, the A linking group is an alkyl group having 1 to 14 carbon chains and an alkoxyl containing 1 to 14 carbon bonds. In an embodiment of the invention, Β!, B2 are independently selected from the group consisting of -COO-, -OOC-, -(〇〇)-, and -CH2. In an embodiment of the invention, the B3 and B4 linkages are each independently selected from the group consisting of -coo-, -OOC-, -N=N-, -C=N-, -CFr, -OCFr, -OC-, and alkynyl groups. (alkyne), -(〇〇)-, -CHr and -(s=o)-. In an embodiment of the invention, the B5 and B6 linkages are each independently selected from the group consisting of -coo-, -OOC-, -N=N-, -ON-, -CFr, -OCFr, -C=C-, and alkynyl groups. (alkyne), -(〇〇)-, _CH2- and -(s=o)-. In one embodiment of the invention, the isosorbide groups are each independently selected from the following isomers:

In an embodiment of the present invention, the optically active liquid crystal composition comprises at least two sets of substituted filaments of An/G!, 201226540 m/G3, and avg4 shots, and the anions, αΓ2, Ar3 and Ar4 in the pot are independently aromatic rings and impurities. One of the rings/one of them, and having the substitution of 心3 and 〇4, respectively, in the present invention-embodiment, Ari, ΑΓ2, ΑΓ3 and the fraction self-stretching phenyl, stretching-based, In the present invention-embodiment, the values of x and y are independently 〇~4, respectively. In the second invention - the values of 'm, n' are independently 〇~4.

In an embodiment of the present invention, Gi is selected from the group consisting of ^(7)士和卜 substituents, and the values of the examples bp, q, r, and s are independently selected. U proposed - the view of the silk material, which has a different style of clothing == and, the quality, thereby providing a large number of optical rotation center = blue phase. The optically active compound of the present invention has the structure shown below

(II) In the structural formula (II):

Cl and C2 are each a soft chain containing 丨~14 carbons, ΑΓ1, ΑΓ2, ΑΓ3, ΑΓ4 are respectively Uyclic linking group, and Gi G2, G3 and G4 are Ar, Ar2, Ar3 and A respectively. . The monovalent substituent, 201226540 m, x is not 0 at the same time, η, y are not Ο at the same time, p, q, r, s are integers, respectively, k is an integer of 2-4 B!, B2, B3, B4, B5 And B6 are each independently a divalent linking group, and A is a soft chain linking group containing 1 to 14 carbons. In one embodiment of the invention, the A linking group is an alkyl group having 1 to 14 carbon chains and an alkoxyl having 1 to 14 carbon bonds. In an embodiment of the invention, B2 is independently selected from the group consisting of -COO-, -OOC-, -(〇〇)-, and -CH2. In an embodiment of the invention, the B3 and B4 linkages are independently selected from the group consisting of -coo-, -OOC-, -N=N-, -C=N-, -CF]-, -OCF2··, -C=. C-, alkyne, - (C = 0) -, -CH, - and - (S = 0) - 一 In an embodiment of the invention, the B5, B6 linkages are independently selected from - COO-, -OOC-, -N=N-, -C=N-, -CFr, -OCFr, -OC-, alkynyl (alkyne), -(C=0)-, -CH2- and -( s=o)-. In one embodiment of the invention, the isosorbide groups are each independently selected from the following isomers: 201226540

In the present invention - the embodiment, the knob liquid crystal composition comprises Aw a: 2! r:, Ar4 / G4, which makes at least two sets of substituent combinations, and 1 Μ, Ling private and Ar4 are independent: 'and have G, G2, G3, and 2, respectively; base (4) = in the first embodiment of the invention, "" self-extension base, stretch bite base, stretch ring hexyl group and extension group 之 base In the present invention-embodiment, the values of x and y are independently 〇~4. . In the present invention-embodiment, the values of m and n are independently 〇~4. In the present invention-embodiment, Gl, G2, G^G are selected from the embodiment of the present invention, and the values of p, q, r, and s are independently selected from the group of the present invention, and the blue phase is further proposed. A liquid crystal composition comprising a reactive monomer having at least one reactive ethylene bond, a photoinitiator, a blue phase liquid material = and a fluorene dopant. Optically active dopants have the following structural formula (I) '· 201226540

In the structural formula (i):

Cl and C2 are each independently a soft chain containing 1 to 14 carbons, and G G 4 is a cyclic linking group (CyCliclinking gr〇up):

Gl, G2, _""ri, Ar2, Pm, X are not 不同 at the same time, ί, y, y are not 〇, P, q, r, s are integers, respectively, I 2 B3 B4 B5, B6 respectively Independently a divalent linkage group) » A is a soft chain linkage containing 1 to 14 carbons. In one embodiment of the invention, the A linking group is an exfoliating group U1M comprising 1 to 14 carbon chains, and an alk〇xyi comprising W4 carbon chains. In the present invention - the implementation of the shot, Bl, b2 is turned upside down from _c〇〇, _〇〇c_, -(C=0)- and -CH2. In an embodiment of the invention, the B3 and B4 linkages are each independently selected from the group consisting of _c〇〇_, -OOC-, -N=N-, -C=N-, -CFr, _0CFr, _c=c_, and alkyne Alkyne, -(C=0)-, _CHr and -(S=0)- 0 In an embodiment of the invention, the BS and B6 linkages are each independently selected from _coo_, -OOC-, ·Ν= Ν...C=N_, _CFr, VIICFr, _c=c_, ethynyl e), 201226540 -(〇〇)-, -ch2-, (s, _. Isosorbide groups are independently selected from the following An isomer in one embodiment of the invention:

In the present invention, the optically active liquid crystal composition comprises at least two groups of substituent combinations of A(10), Λ 'know%' ΑΓ 4%, wherein 2 U1*4 are independently an aromatic ring, a heterocyclic ring and an alicyclic hydrocarbon. One, and have 02, 03 and respectively. a substituent of 4.

In the case of self-extension benzene, Arl, A"2, Ar"3 and A"4 independently select one of the soil, the stretched wire, the stretched hexyl group and the stretched (four) base. In the present invention, the values of x and y are independently independent. In the present invention - the examples, the values of m and η are each independently 〇4. In an embodiment of the present invention, the values of p, q, and ~ are independently selected from the group consisting of φ, 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 ▲ Therefore, the present invention can propose a new molecular structure based on the isosorbite group based on the blue phase liquid crystal material, thereby providing a large amount of the spin ring 13 201226540 light center to induce the blue phase. In this way, a smaller proportion of optically active dopants can be used to represent a wider range of blue phase liquid crystal temperatures and lower drive voltages. This is a practical solution in the field of blue-phase liquid crystal displays. [Embodiment] The present invention is directed to providing a novel isosorbide derivative. When used as an optically active dopant, the blue phase properties of the blue phase liquid crystal material can be induced, and the blue phase temperature of the blue phase liquid crystal formulation is extended and the driving voltage thereof is lowered. The present invention provides a blue phase liquid crystal composition in a first aspect. The blue phase liquid crystal composition of the present invention comprises a reactive monomer, a photoinitiator, a blue phase liquid crystal material, and an optically active dopant. The reactive monomer has at least one reactive ethylene bond, and the polymerization can be carried out under the action of a photoinitiator. A suitable reactive monomer may be a molecule as shown in Figure 2, for example RM257 (1,4-(4-(3 - Aery loyloxy-propoxy)-benzoic acid)-2-methyl benzene) mixed triterpene thiol Propylene triacetate (DMPAP) or 2-ethyl φ-hexyl acrylate (ΕΗΑ), which accounts for (1% to 20%) mole percentage of the blue phase liquid crystal composition. A suitable photoinitiator may be a molecule as shown in Figure 3 (polyethylene glycol octylphenyl ether, DMPAP), which accounts for a percentage of moles in the blue phase liquid crystal composition (0.1% to 3%). The blue phase liquid crystal material in the blue phase liquid crystal composition of the present invention may be a biphenyl type compound such as the molecular amyloxybenzonitrile (5CB), 4'-(4-ethyl group shown in Fig. 4; -cyclohexyl)-3,4-difluorobiphenyl S - 14 201226540 (4-(4-ethyl-cyclohexyI)-3,4-difluoro_biphenyl), 4'-(4-propyl-cyclohexyl)-3, 4-, 4-(4-propyl-cyclohexyl)-3,4-diflU〇r〇-biphenyl, 4,-(4-pentyl-cyclohexyl)_3 4-difluorobiphenyl 4-(4-pentyl-cyclohexyI)-3,4-difluoro-biphenyl)(JC1041XX)

, accounting for the percentage of moles in the blue phase liquid crystal composition (50% to 9%). The optically active doped f in the blue phase liquid crystal composition of the present invention is an isosorbide g-derived derivative having a plurality of isosorbide S groups capable of providing a large amount of optical rotation centers to induce a blue phase, which accounts for blue The percentage of moles in the liquid crystal composition (1% to 1 G%). The pharmaceutically acceptable dopant in the blue phase liquid crystal composition of the present invention is an optically active compound and may have the following structural formula (I):

In the structural formula (I), Cl c2 is independently contained in the range of ~~... Δr Λ Α 、, 'sheng substituted or unsubstituted ,, h, G2, g3 and G4 are Αη, 八土 yc IC Linking group ),

5 Γ3# , y is not 不同 at the same time, 曰 horse m, x is not 0 at the same time, and n, p, q, r, s are positive integers, respectively, bi, b2, b3, b4, b5, B6 (linking group), horse monovalent substituted or unsubstituted 15 201226540 A is a linking group comprising 1 to 14 carbon-substituted or unsubstituted soft chains. - For the A linking group, it may be a linear or branched group containing carbon or oxygen. For example, a stretching base comprising 1 to 14 carbon chains or an alkoxy group containing 1 to 14 carbon chains. Further, the linking groups B! and B2 bonded to the A linking group may be a divalent linking group containing carbon or oxygen. For example, 'B1, B' can be -COO-, -OOC-, -(〇〇)-, and -CH2, respectively. In one aspect, the B3, B4 linkage and the B5, B6 linkage are each bonded to an isosorbide group. B3 and B4 may each be a divalent linking group containing carbon, oxygen, nitrogen, sulfur, or halogen, and may have a double bond or a hydrazone bond as the case may be. For example, the B3 and B4 linkages may each be -COO-, -OOC-, -N=N-, -C=N-, -CF2-, -OCF2-, -OC-, -CeC-(alkenyl) ), -(〇〇)-, -ch2- and -(s=o)-. On the other hand, the b5 and b6 linking groups may each be a divalent linking group containing carbon, oxygen, nitrogen, sulfur, or dentate, and may have a double bond or a hydrazone bond as the case may be. For example, the B3 and B4 linkages may each be -C00-, -00C-, -N=N-, -C=N-, -CF2-, -0CF2-, -C=C-, an alkynyl group, - (C=0)-, -ch2- and ·ρ=ο)·. In the present invention, the term "aromatic ring" group includes an aromatic (heteroaryl) group of a carbocyclic ring and a heterocyclic ring, and is, for example, a five-membered ring or a six-membered aromatic ring or a polycyclic aromatic ring. It is a phenyl group, a biphenyl group, a naphthyl group, an anthracyl group, and a heteroaromatic group such as a pyridyl group. In the present invention, the term "soft chain" or "linking group" is a divalent linear, branched, substituted or unsubstituted non-aromatic hydrocarbon group which may be saturated or contain one. Or a group of multiple unsaturated units. "soft chain" or "connected

The S 16 201226540 "group" group is preferably a linear or branched alkyl group, for example, a methyl group, an ethyl group, a propyl group or a fluorenyl group. In the present invention, the term "alicyclic hydrocarbon" is a substituted or unsubstituted cyclic non-aromatic hydrocarbon group which may be saturated with a carbocyclic or heterocyclic ring or contain one or more unsaturated units. Group. The alicyclic hydrocarbon group is preferably a linear or branched divalent group, for example, a cyclohexyl group or a hydrazine group. Further, the aforementioned groups may be optionally substituted with one or more typical substituents such as ii or other similar substituents. In the present invention, the term "substituted" means that a hydrogen atom is substituted by one or more substituents (which may or may not be the same), for example, the substituent includes, but is not limited to, hydrogen or a halogen, such as It, gas, and desert. Or worm. In the present invention, the term "asymmetric" group or "optical" refers to an isomer molecule having one or more asymmetric centers, the molecular arrangement of which is either left-handed or right-handed, structurally mirrored to each other and Cannot overlap, molecules with asymmetric centers will show optical rotation. In an embodiment of the invention, the isosorbide group may comprise a stereoisomer. As shown in Fig. 1, since isosorbide has four optical centers in its molecular structure (* position is a chiral center), that is, as indicated by the carbon indicated by the asterisk, Derivatives of the optically active center have a variety of possible optical isomers. Possible optical isomers of isosorbide are as follows: 17 201226540

In an embodiment of the present invention, an optically active compound in an optically active liquid crystal composition, that is, an optically active compound, includes Ari/G1, Ar/(/Ar3/G3, Ar4/G4 substituent combinations, and each of them as required 2: The value of the two copies is independent of each other. + m, — : 2, X is not the same as 〇 ' and ' is not 0 at the same time. The exchange, the parent isosorbide group will be at least _ '. And s are the positive records. Take the silk bond. p, q, gossip, Ar2 ring substituents can be ^nr u two ring cyclic substituents. Twenty to Feng Fangxiang, and with Ar4 can be divided into, for example,伸娘丝. 4 Stretching the base, stretching the base, stretching g 舆 as if: containing multiple substituents, g2'G3 αΓ3^λ^, ^14;;::Γ3Λα^-^^αΓι>α^ Contains 3 monovalent substituents ":, . 2: base and 2 18

S · 201226540 G2, G3 and G4 can be independently hydrogen, a combination of elements or - Γ, s 1 壬. Halogen can be fluorine, chlorine, bromine or iodine. The optically active dopant of the blue phase liquid crystal composition of the present invention may also have an optically active oligomer of the following formula (II):

Ci- (G3)p -Ar and m B6-〇'

P-b3 (|1)q hAr

A (^) , Ar2- -B4 ~〇

(i4)s - C2 (II), the difference between the structural formula (1) and the structural formula (8) is that the structural formula (8) = contains at least 3 heterotetrazide groups, and thus k can be 2 slaves of any integer. /, the implementation of the remainder, please refer to the description of the structural formula (I). In the examples of the present invention, the molecules in the two structural formulae (1) and the structural formula (8) can be synthesized using a general chemical method. For example, the precursor can be used to synthesize the molecules of the structural formula (1) and the structural formula (Π) of the present invention. The conditions of the present invention are as follows: (4) The molecules of the formula (1) and the structure of the formula (II) can be synthesized. Please refer to the simplified reaction formula shown below. Providing a diacid precursor (A) with an isosorbide precursor (B) in dioxane (DCM), and a deuteration catalyst such as 4 dimethylamino (tetra) (DMAp), dehydrated : with the aid of dicyclohexylcarbodiimide (DCC), the isosorbide (8) (4)' and the diacid precursor (A) are dehydrated and combined to form two isosorbide groups. (C) (α 201226540 -(4-(4-hexyloxy-benzoic acid isosorbide-ester)- phenyl-yloxy)-ω -(4-(4-hexyloxy-benzoic acid isosorbide -ester)-phenyl-yloxy )hexane) °

The diacid precursor (A) and the isosorbide precursor (B) may each have a dentate substituent as required. If the diacid precursor (A) and the isosorbide S precursor (b) have a halogen substituent, the product (c) has an i-substituent. If the diacid precursor (A) and the isosorbide precursor (B) have no dentate substituent, the product (C) has no halogen substituent. Figures 5-10 illustrate the molecular structures of several optically active dopants of the present invention. For example, Figure 5 illustrates the optically active dopants ID-1 and ID-2, which may optionally have a halogen substituent. One of the directions of the invention is to provide an optically active compound having a plurality of isosorbide groups. In the case of optically active dopants, the optically active compound of the present invention can provide a large amount of optically active centers to induce a blue phase liquid crystal and a k phase of a. Therefore, by using the optically active compound having a plurality of isosorbide groups of the present invention as the optically active #f', an optically active composition of the remaining liquid crystal can be obtained. Table 1 is an optically active composition having a plurality of isosorbide 201226540 - ester group systems ID-1 and ID-2, which is provided by an embodiment of the present invention, and has a single isosorbide group system as compared with the comparative example ( The composition of IS-1) and (IS-2), as a result of the blue phase temperature and blue phase range exhibited in the blue phase liquid crystal compositions of different formulation ratios. The single isosorbide group dopants of the comparative examples are referred to as (IS-1) and (IS-2), and the molecular structure is as shown in Fig. 11 (bis(4-hexyloxyalkyl vinegar) isosorbide Isosorbide bis-(4-hexyloxy-benzoate) and bis(4-hexyloxy-benzoic acid isosorbide) )) ° Sample Reactive Monomer Photoinitiator Blue Phase Liquid Crystal Material Molar Rate % RM257 EHA TMPTA DMPAP JC1041XX 5CB 1 2.8 3.79 0.34 43.84 44.14 2 2.52 3.89 0.32 45.66 42.74 3 2.8 3.87 0.53 44.94 43.24 4 2.6 4.01 0.73 44.74 43.03 5 2.63 3.91 0.49 45.73 44.4 6 2.71 3.94 0.34 45.63 44.84 7 2.63 3.93 0.52 45.76 44.68 8 2.67 3.96 0.54 45.57 44.66 Table 1 21 201226540 Sample Mohr % Optical Rotation

IS-1 IS-2 ID-1 TId^T 4.89 Blue phase temperature °C ~4~2 2 4.89 28X25J0

Table 1 continued

The formulation samples i to 4 of the comparative examples were formulated with the single molecule system (6) and IS-2 as optically active additives, and the optically active doping mass was about 4 89 mol%, while the blue phase range was about 3.3. (: _7.3^; Between. After replacing the traditional single-molecule system with the ceremonial subsystem of the present invention, taking two isosorbide-brewing groups of bimolecular _ derivative ID] and ID-2 as an example, Under the same formulation conditions, when the molar addition of moieties is reduced by half (4.89 mol% to 2.45 mol%), the upper limit of the blue phase temperature of samples 5 to 8 is not only improved, but also extended blue. The phase temperature is wide, which is beneficial to reduce the difficulty of the back-end process. It can be seen from the results of the observation that the blue phase liquid crystal formulation of the present invention, including the optically active center bimolecular and ID-2), is only a comparative single molecule system ( Hi and is_2) 50 〇 / °, but can have a relatively wide blue phase temperature (8.5 ° C to 9.6. 〇.

S 22 201226540 • 帛12_ shows the hinge provided by the experimental example of the present invention (4) 10_2 and the comparative example, the isosorbide group dopant, called (is-υ and (IS-2), electric wear-through Curve of permeability. Three kinds of samples are poured into a liquid crystal cell, such as a liquid crystal display module of a milk liquid crystal display module, and the voltage versus transmittance (called a curve. The liquid crystal material containing the conventional IS) and the IS_2 is compared after the photopolymerization process. The driving voltage of the liquid crystal material containing the id_2 of the present invention is clearly lower than that of the former two, which fully demonstrates the optically active dopant of the multi-molecular system of the present invention. The extension of the eye temperature can reduce the driving voltage of the blue phase liquid crystal. Therefore, by observing the result of Fig. 12, it can be seen that the optically active dopant lD_2 provided by the present invention can reach the conventional level at a lower driving voltage. The formulation of the mono-isosorbide vinegar group has the same or even better penetration. The above experimental results can be used in the present invention to provide optically active compounds and optically active oligomers for use in blue phase liquid crystal compositions. In the middle, it is beneficial to the blue phase module display Preparation process of the device, and improve the traditional disadvantages of a high driving voltage of the formulation.

The above is only the preferred embodiment of the present invention, and all changes and modifications made to the scope of the present invention should be within the scope of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 illustrates that isosorbide is a dipentacyclic molecule containing dioxane. Figure 2 illustrates a suitable reactive monomer of the present invention. Figure 3 illustrates the photoinitiator of the present invention. 23 201226540 Fig. 4 illustrates a blue phase liquid crystal material in the blue phase liquid crystal composition of the present invention, which may be a biphenyl type compound. Figures 5-10 illustrate the molecular structures of several optically active dopants of the present invention. Fig. 11 illustrates the molecular structure of the single isosorbide-based ruthenium (IS-1) and (IS-2) of the comparative example. Fig. 12 is a graph showing a comparison of voltage versus transmittance of the optically active dopants provided in the experimental examples of the present invention and the single isosorbide group dopants of the comparative examples. [Main component symbol description] None

.S 24

Claims (1)

201226540 VII. Patent Application Range: 1. A blue phase liquid crystal composition comprising: a reactive monomer comprising at least one reactive ethylenic bond and having a total blue phase liquid crystal composition of from 1% to 20% by mole; a photoinitiator with a total blue phase liquid crystal composition % to 3% molar percentage: a blue phase liquid crystal material having a total blue phase liquid crystal composition of 50 to 90% molar percentage; and an optical rotation #f (ehimldopam) having a full enchantment liquid crystal composition of 1 〇 / 〇 ~ 1 〇 % Mo The percentage of the ear, as well as the structural formula (I) shown below: Q, 〇 2 points _ stand for a soft chain containing 1 to 14 carbons substituted or unsubstituted; ΑΓ 1, M, such as, Ar4 are cyclic linkages (cyca this kinggroup); G, G2 G3 and 〇 4 are the monovalent substituents of Ari, Ar2, Ar3 and μ respectively; m and x are not 〇 at the same time, and n and y are different 〇: 卩, 9, 1*, 8 are positive integers respectively; ^ B2 B3 B4, B5 and b6 are each independently a divalent substituted or unsubstituted linking group; and A is a soft bond linking group comprising 1 to 14 carbons which are substituted or unsubstituted. 25 201226540 2. The blue phase liquid crystal composition of claim 1, wherein A is selected from the group consisting of an alkyl group of 1 to 14 carbon chains and an extension of 1 to 14 carbon chains. Alkoxyl. 3. The blue phase liquid crystal composition of claim 1, wherein &, b2 are independently selected from the group consisting of -COO-, -OOC-, -(c=o)-, and -CH2. 4. The blue phase liquid crystal composition of claim 1, wherein the & B4 linkage base is independently selected from the group consisting of -coo-, -ooc-, -N=N-, -C=N-, -CF2. -,_0CF2_, _〇C-, alkynyl, -(C=0)·, -CHr and -(S=0)-. 5. The blue phase liquid crystal composition of claim 1, wherein the b5 and b6 linkages are independently selected from the group consisting of -coo-, -〇〇c_, _N=N_, _C=N_, _CI?2, 〇CF2. c=c, fast base (alkyne), -(C=〇)_, _CHr and -(S=0)-. 6. If you apply for a patent scope! A blue phase liquid crystal composition wherein &, [2, respectively, is an alkyl group and an alkoxyl group. 7. The blue phase liquid crystal composition of claim 1, comprising at least two sets of substituent combinations of Arl/Gl, 2 2 Ar3/G3 Ar4/G4, such as A, A. A1·3 and A1·4 are each independently one of an aromatic ring, a heterocyclic ring and an alicyclic hydrocarbon, and have G!, G2, G3 and G4 substituents, respectively. 5 26 201226540 8. The blue phase liquid crystal composition of claim 7, wherein Ar!, Ar2, Ar3, and Ar4 are each independently selected from the group consisting of phenylene and phenylene. One of a pyridyl group, a cyclohexyl group and a piperazine group. 9. The blue phase liquid crystal composition of claim 7, wherein the values of X and y are independently from 0 to 4. 10. The blue phase liquid crystal composition of claim 7, wherein the values of m and η are independently 0 to 4. 11. The blue phase liquid crystal composition of claim 7, wherein the G!, G2, G3 and G4 substituents are independently selected from the group consisting of ruthenium, F, Q, Br and I. 12. The blue phase liquid crystal composition of claim 7, wherein the values of p, q, r, and s are each independently selected from 1 to 4. 13. An optically active compound having a diisosorbide group, the structural formula (1) being as follows: (1) Inducing an optically active dopant having a cholesterol phase and a blue phase liquid crystal (chiral 27 201226540 dopant), wherein Ci and C2 are independently soft containing 1 to i4, or substituted or unsubstituted Chains; Ar丨, Ar2, Ar3, and Ar4 are respectively C cyclic linking group); Gi, G2, G3, and G4 are 单价η, At* a Λ A"2, Ar3 and 八! 111; 乂, 乂 is not 〇 ' and 11, 丫 is not 〇 p, q, r, s, 丨 J is a positive integer; 1 2 3 4 5 B" not independently replaced by divalent or secret a linking group; and A is a soft chain linking group comprising 1 to 14 carbons which are substituted or unsubstituted. , an isosorbide group, structural formula (II) An optically active dopant of liquid crystals 14. An optically active oligomer, as follows: (chiral is induced as having a cholesterol phase and a blue phase dopant), wherein C!, (:2 are independently soft bonds containing 14 carbons substituted or unsubstituted; ΑΓ1, Μ, ru, ΑΓ4 are rings respectively a linkage group (called a linking group); G!, G2, G3 and G4 are the monovalent substituents of Ar A η respectively; ^ when the difference is not ... and ^ 乂 is not the same as the heart S - 28 201226540 -p, q, r, s is further 丨 J is a positive integer; k is a positive integer; Bi, B2, B3, B4, B5, B6 are each independently a divalent substituted or unsubstituted linking group; and the A linking group is included 1 to 14 soft chains which are substituted or unsubstituted. 15. An optically active oligomer according to claim 14 wherein the value of k is selected from 2, 3 and 4. /\, 29