TWI447211B - Chiral compound with isosorbide moiety and chiral composition and blue phase liquid christal composition thereof - Google Patents

Description

Optically active compound having isosorbide group, optically active composition thereof and blue phase liquid crystal composition

The present invention generally relates to an optically active compound and composition having isosorbide groups. In particular, 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 comprising 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.

The blue phase or BP liquid crystal is a self-aggregating three-dimensional photonic crystal structure, which usually occurs between the isotropic phase and the cholesteric phase. The blue phase liquid crystal molecular layer and the layer are arranged in a columnar arrangement, and the molecular arrangement behavior is relatively special. As can be seen from the scientific studies published in modern times, for example, Chemistry Letter, 2008, 12, 1242, the liquid crystal molecules extend from the vertical alignment of the central principal axis molecules to the outer rotation, and the more outwardly extending molecules are spirally twisted until The outermost 45 degrees.

Arranging from a vertical center to four circumferences to form a cylinder arrangement with a cylindrical diameter of 1/4 pitch (pitch/4, or P/4), and such cylinders are stacked in different ways. Form a self-interlaced arrangement. The staggered junctions in the cylindrical arrangement produce lattice defects, such lattice defect points will form a cubic stack arrangement, which can be divided into three phases: blue phase (I), blue phase (II), and blue phase (III). Arranged. They are body center cubic, simple cubic, and iso-like alignment.

However, no matter which kind of blue phase liquid crystal is arranged in an isotropic direction, the lattice axiality in any direction is uniform, and therefore it can 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 a short wave, it can be found by observing the blue phase texture map with a polarizing microscope that the appearance of the blue phase is mostly a mosaic texture map of blue or blue-violet color. Named after.

The most well-known feature of blue-phase liquid crystal materials is that the reaction speed under the action of an 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 a dark state. It is pointed out in the literature that a positive blue phase liquid crystal must induce a birefringence by using a transverse electric field generated by an electrode similar to an IPS (in-plane switch) liquid crystal display ( The change in Δn, positive birefringence (Δn>0) in turn produces a bright dark state change. From a giant point of view, the positive blue phase liquid crystal appears bright under an applied electric field.

The liquid crystal display made of the blue phase liquid crystal material has the characteristics of ultra-high fast response, and can reach the level of several hundred microseconds at the fastest. In the early days, the blue phase temperature range exhibited by the blue phase liquid crystal material was too narrow, for example, only 1-2 ° C, which has been a major drawback of the application of the blue phase liquid crystal material. However, in recent years, it has been found that the blue phase temperature can be widened by blending different proportions of reactive monomers in the temperature range of the blue phase by means of photopolymerization (Nature materials, 2002, 1, 64). To a few tens of degrees (>60 ° C), the problem of the blue phase temperature of the blue phase liquid crystal material being too narrow is therefore theoretically solved.

Isosorbide is a dipentacyclic molecule containing dioxins. As shown in Fig. 1, although the molecular derivative of isosorbide as the optical center has four optical centers in the molecular structure, it can be used as an optically active dopant to induce blue phase, but isosorbide. The steric obstacle of the group is too large, and its liquid crystal characteristics are not obvious. Therefore, when it is used as an optically active dopant, the original liquid crystal phase is easily broken, so it is not suitable for high-frequency blending.

On the other hand, isosorbide has a problem that the driving voltage is too high in the blue phase liquid crystal material. In the case of certain known isosorbide derivatives, it is disclosed in U.S. Patent No. 7,440,160 B2 that these isosorbide derivatives do not themselves have any liquid crystal phase. Although it is possible to induce a blue phase liquid crystal by mixing it with a liquid crystal having a nematic phase, it has disadvantages such as an excessive driving voltage. For example, even if the blue phase liquid crystal can be successfully induced, the saturation voltage is not seen when the driving voltage is increased to 170V.

Therefore, the application of the blue phase liquid crystal material still has the disadvantage of requiring a high driving voltage, so how to reduce the driving voltage of the blue phase liquid crystal display becomes another important point that needs to be overcome.

The composition of the blue phase liquid crystal usually has a host liquid crystal (host LC) and a chiral dopant, and is doped with a polymerizable monomer to form a blue phase liquid crystal system containing a polymerizable monomer and a polymerizable monomer. For the molecular composition, the inclusion of an optical center additive is an important factor affecting the photoelectric properties of the blue phase liquid crystal. When the number of optical centers contained in a single optically active central molecular structure increases, a larger amount of optically active substance can be provided to induce a blue phase, but the addition of too many or too few optically active center molecules leads to a chiral nematic phase. ). The present invention thus designs a single structure containing a plurality of optically active centers to serve as optically active dopants.

The present invention then first proposes an optically active compound having a diisosorbide group as an optically active dopant thereby providing a plurality of optically active centers to induce a blue phase. The optically active compound of the present invention has the structural formula (I) shown below:

In the structural formula (I): C ₁ and C ₂ are each independently a soft chain containing 1 to 14 carbons, and Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each a cyclic linking group, G ₁ , G ₂ , G ₃ and G ₄ are the monovalent substituents of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , respectively, and m and x are 0 when they are not different, and n and y are different when they are 0, p, q, r, s is an integer, and B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , and B ₆ 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 chains.

In an embodiment of the invention, B ₁ and B ₂ are each independently selected from the group consisting of -COO-, -OOC-, -(C=O)-, and -CH ₂ .

In an embodiment of the invention, the B ₃ and B ₄ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-.

In an embodiment of the invention, the B ₅ and B ₆ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - 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 invention, the optically active liquid crystal composition comprises at least two sets of substituent combinations of Ar ₁ /G ₁ , Ar ₂ /G ₂ , Ar ₃ /G ₃ , Ar ₄ /G ₄ , wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently one of an aromatic ring, a heterocyclic ring and an alicyclic hydrocarbon, and each have a substituent of G ₁ , G ₂ , G ₃ and G ₄ .

In one embodiment of the invention, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently selected from the group consisting of a phenylene group, a pyridyl group, a cyclohexyl group and a piperazine group.

In an embodiment of the invention, the values of x and y are independently 0 to 4.

In an embodiment of the invention, the values of m and n are independently 0 to 4.

In one embodiment of the invention, the G ₁ , G ₂ , G ₃ and G ₄ substituents are each independently selected from the group consisting of H, F, Cl, Br and I.

In an embodiment of the invention, the values of p, q, r, and s are each independently selected from 1 to 4.

The present invention further proposes an optically active oligomer having a plurality of isosorbide groups as an optically active dopant, thereby providing a plurality of optically active centers to induce a blue phase. The optically active compound of the present invention has the structural formula (II) shown below:

In the structural formula (II): C ₁ and C ₂ are each independently a soft chain containing 1 to 14 carbons, and Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are respectively a cyclic linking group, G ₁ , G ₂ , G ₃ and G ₄ are the monovalent substituents of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , respectively, and m and x are 0 when they are not different, and n and y are different when they are 0, p, q, r, s are integers, and k is an integer of 2-4. B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , and B ₆ are each independently a binary linking group, and A is 1 to 14 carbons. Soft chain linkage.

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 chains.

In an embodiment of the invention, B ₁ and B ₂ are each independently selected from the group consisting of -COO-, -OOC-, -(C=O)-, and -CH ₂ .

In an embodiment of the invention, the B ₃ and B ₄ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-.

In an embodiment of the invention, the B ₅ and B ₆ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - 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 invention, the optically active liquid crystal composition comprises at least two sets of substituent combinations of Ar ₁ /G ₁ , Ar ₂ /G ₂ , Ar ₃ /G ₃ , Ar ₄ /G ₄ , wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently one of an aromatic ring, a heterocyclic ring and an alicyclic hydrocarbon, and each have a substituent of G ₁ , G ₂ , G ₃ and G ₄ .

In one embodiment of the invention, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently selected from the group consisting of a phenylene group, a pyridyl group, a cyclohexyl group and a piperazine group.

In an embodiment of the invention, the values of x and y are independently 0 to 4.

In an embodiment of the invention, the values of m and n are independently 0 to 4.

In one embodiment of the invention, the G ₁ , G ₂ , G ₃ and G ₄ substituents are each independently selected from the group consisting of H, F, Cl, Br and I.

In an embodiment of the invention, the values of p, q, r, and s are each independently selected from 1 to 4.

The present invention further contemplates a blue phase liquid crystal composition comprising a reactive monomer having at least one reactive vinyl bond, a photoinitiator, a blue phase liquid crystal material, and an optically active dopant. The optically active dopant has the structural formula (I) shown below:

In the structural formula (I): C ₁ and C ₂ are each independently a soft chain containing 1 to 14 carbons, and Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each a cyclic linking group, G ₁ , G ₂ , G ₃ and G ₄ are the monovalent substituents of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , respectively, and m and x are 0 when they are not different, and n and y are different when they are 0, p, q, r, s is an integer, and B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , and B ₆ 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 chains.

In an embodiment of the invention, B ₁ and B ₂ are each independently selected from the group consisting of -COO-, -OOC-, -(C=O)-, and -CH ₂ .

In an embodiment of the invention, the B ₃ and B ₄ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-.

In an embodiment of the invention, the B ₅ and B ₆ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, - C=C-, alkynyl, -(C=O)-, -CH ₂ - 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 invention, the optically active liquid crystal composition comprises at least two sets of substituent combinations of Ar ₁ /G ₁ , Ar ₂ /G ₂ , Ar ₃ /G ₃ , Ar ₄ /G ₄ , wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently one of an aromatic ring, a heterocyclic ring and an alicyclic hydrocarbon, and each have a substituent of G ₁ , G ₂ , G ₃ and G ₄ .

In one embodiment of the invention, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are each independently selected from the group consisting of a phenylene group, a pyridyl group, a cyclohexyl group and a piperazine group.

In an embodiment of the invention, the values of x and y are independently 0 to 4.

In an embodiment of the invention, the values of m and n are independently 0 to 4.

In one embodiment of the invention, the G ₁ , G ₂ , G ₃ and G ₄ substituents are each independently selected from the group consisting of H, F, Cl, Br and I.

In an embodiment of the invention, the values of p, q, r, and s are each independently selected from 1 to 4.

Therefore, the present invention can propose a new molecular structure based on the isosorbide group for the blue phase liquid crystal material, thereby providing a large amount of optical rotation 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.

The 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-Acryloyloxy-propoxy)-benzoic acid)-2-methyl benzene) mixed trimethylolpropane Triacrylate (DMPAP) or 2-ethyl-hexyl acrylate (EHA) 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 (0.1% to 3%) mole percent of the blue phase liquid crystal composition.

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 pentyl biphenyl cyanide (5CB), 4'-(4-ethyl group shown in Fig. 4 -4'-(4-ethyl-cyclohexyl)-3,4-difluoro-biphenyl, 4'-(4-propyl-cyclohexyl)-3,4 -4'-(4-propyl-cyclohexyl)-3,4-difluoro-biphenyl, 4'-(4-pentyl-cyclohexyl)-3,4-difluorobiphenyl (4' -(4-pentyl-cyclohexyl)-3,4-difluoro-biphenyl) (JC1041XX), which accounts for (50% to 90%) the percentage of moles in the blue phase liquid crystal composition. The optically active dopant in the blue phase liquid crystal composition of the present invention is an isosorbide derivative having a plurality of isosorbide groups, which can provide a plurality of optical rotation centers to induce a blue phase, which accounts for a blue phase liquid crystal combination. The percentage of moles (1% to 10%). The optically active 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), C ₁ and C ₂ are each independently a soft chain containing 1 to 14 carbons which are substituted or unsubstituted, and Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are respectively cyclic linking groups. (cyclic linking group), G ₁ , G ₂ , G ₃ and G ₄ are monovalent substituents of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , respectively, and x, y, m and n are integers, respectively, but the book is m And x is 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, respectively, and B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , and B ₆ are respectively independently divalent. A substituted or unsubstituted linking group, A is a linking group comprising a soft chain of 1 to 14 carbons which are substituted or unsubstituted.

For the A linking group, it may be a linear or branched group containing carbon or oxygen. For example, an alkylene group having 1 to 14 carbon chains or an alkoxy group having 1 to 14 carbon chains. Further, the linking groups B ₁ and B ₂ bonded to the A linking group may be a divalent linking group containing carbon or oxygen. For example, B ₁ and B ₂ may each be -COO-, -OOC-, -(C=O)-, and -CH ₂ .

In one aspect, the B ₃ , B ₄ linking group and the B ₅ , B ₆ linking group are each bonded to an isosorbide group. B ₃ and B ₄ 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 B ₃ and B ₄ linking groups may each be -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, -C=C-, - C≡C-(extended alkynyl), -(C=O)-, -CH ₂ - and -(S=O)-. On the other hand, the B ₅ and B ₆ linking groups 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 B ₃ and B ₄ linking groups may each be -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ -, -OCF ₂ -, -C=C-, and Alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-.

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 ring or a polycyclic aromatic ring, which may be Phenyl, biphenyl, naphthyl, anthracyl, and heteroaromatic groups such as pyridyl.

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. The "soft chain" or "linking 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 piperazinyl group. Further, the aforementioned groups may be optionally substituted with one or more typical substituents such as halogen or other similar substituent groups.

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 fluorine, chlorine or bromine. Or iodine.

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:

In an embodiment of the invention, the optically active dopant in the optically active liquid crystal composition, that is, the optically active compound, includes Ar ₁ /G ₁ , Ar ₂ /G ₂ , Ar ₃ /G ₃ ,Ar as needed. ₄ / G ₄ substituent combinations, and each having a repeating unit of x, y, m, n. The values of x and y are independent of 0~4, and the values of m and n are independent of 0~4, respectively, but m and x are not 0 at the same time, and n and y are not 0 at the same time. In other words, each isosorbide group will bond to at least one of the foregoing substituents. p, q, r, and s are positive integers, respectively.

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are usually a divalent cyclic substituent. The divalent cyclic substituent may be an aromatic ring, a heterocyclic ring or an alicyclic hydrocarbon. For example, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may each independently be a phenylene group, a pyridyl group, a cyclohexyl group and a piperazine group.

Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each contain a plurality of substituents G ₁ , G ₂ , G ₃ and G ₄ . For example, when Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are a six-membered ring, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each contain four monovalent substituents G ₁ , G ₂ , G ₃ and G _{4 .} . Or when Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are a five-membered ring, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ each contain three monovalent substituents G ₁ , G ₂ , G ₃ and G _{4 .} . The substituents G ₁ , G ₂ , G ₃ and G ₄ may independently be hydrogen, halogen or any combination thereof. The halogen can be fluorine, chlorine, bromine or iodine.

The optically active dopant in the blue phase liquid crystal composition of the present invention may also have an optically active oligomer of the following formula (II):

The structural formula (I) differs from the structural formula (II) in that the structural formula (II) comprises at least 3 isosorbide groups, and thus k can be any integer from 2 to 4. For the rest of the implementation, please refer to the description of the structural formula (I).

In an embodiment of the invention, the molecules of structural formula (I) and structural formula (II) can be synthesized using conventional chemical methods. For example, a precursor can be used to synthesize the molecules of the structural formula (I) and structural formula (II) of the present invention. The conditions of the general standard esterification reaction can be applied to the synthesis of the molecules of the structural formula (I) and structural formula (II) of the present invention.

Please refer to the simplified reaction formula shown below. Providing a diacid precursor (A) and an isosorbide precursor (B) in dichloromethane (DCM), and a deuteration catalyst such as 4-dimethylaminopyridine (DMAP), with a dehydrating agent, For example, with the aid of dicyclohexylcarbodiimide (DCC), the hydroxyl group of the isosorbide precursor (B) is dehydrated and condensed with the carboxyl group of the diacid precursor (A) to form two isosorbide groups. (C)(α-(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 halogen substituent as required. If the diacid precursor (A) and the isosorbide precursor (B) have a halogen substituent, the product (C) has a halogen substituent. If the diacid precursor (A) and the isosorbide precursor (B) have no halogen 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 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 compounds of the present invention can provide a plurality of optically active centers to induce a blue phase of the blue phase liquid crystal composition. Therefore, by using the optically active compound having a plurality of isosorbide groups of the present invention as an optically active dopant, an optically active composition for a blue phase liquid crystal can be obtained.

Table 1 illustrates an optically active composition having a plurality of isosorbide group system ID-1 and ID-2 as provided in an embodiment of the present invention, and a single isosorbide group system (IS-1) as compared with the comparative example. And the composition of (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 benzoate) isosorbide. Isosorbide bis-(4-hexyloxy-benzoate) and bis(4-hexyloxy-benzoic acid isosorbide) )).

Formulation samples 1 to 4 of the comparative examples are formulations in which the monomolecular systems IS-1 and IS-2 are optically active additives, and the optically active doping mass is about 4.89 mol%, and the blue phase range is about 3.3 ° C to 7.3 ° C. between. After replacing the traditional single-molecule system with the multi-molecular system of the present invention, taking two isomeric derivatives of the isosorbide group, ID-1 and ID-2, as an example, under the same formulation conditions, when the bimolecular When the added mole number is halved (4.89 mol% is reduced to 2.45 mol%), the upper limit of the blue phase temperature of sample 5 to sample 8 is not only improved, but also the blue phase temperature is extended, which is advantageous for reducing the back-end process. Difficulty. It can be seen from the results of Table 1 that the blue phase liquid crystal formulation of the present invention contains the addition amount of the optically active center bimolecular (ID-1 and ID-2) only for the single molecule system (IS-1 and IS-2) of the comparative example. 50%, but can have a relatively wide blue phase temperature (8.5 ° C to 9.6 ° C).

Figure 12 is a view showing the optically active dopant ID-2 provided in the experimental example of the present invention and the single isosorbide group dopant of the comparative example, referred to as (IS-1) and (IS-2), voltage pair penetration. The curve of the rate. The three samples are poured into a liquid crystal cell, such as a liquid crystal cell of an IPS liquid crystal display module, and the voltage versus transmittance (V-T) curve is compared after the photopolymerization process. The liquid crystal material containing the conventional IS-1 and IS-2 does not have a saturation voltage at a driving voltage of 170 V, and the driving voltage of the liquid crystal material containing the ID-2 of the present invention is significantly lower than the former two, which fully demonstrates the multi-molecule of the present invention. The optically active dopant of the system not only facilitates the extension of the blue phase temperature, but also reduces the driving voltage of the blue phase liquid crystal. Therefore, observing the results of Fig. 12, it can be seen that at a lower driving voltage, the optically active dopant ID-2 provided by the present invention can achieve the same or even better as the single isosorbide group dopant of the conventional formulation. Penetration rate. Based on the above experimental results, the optically active compound and the optically active oligomer provided by the present invention are useful for the preparation of the blue phase module display when applied to the blue phase liquid crystal composition, and improve the high speed of the conventional formulation. The shortcomings of voltage.

The above are only the preferred embodiments 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.

Figure 1 illustrates that isosorbide is a biquaternary dioxygen-containing molecule.

Figure 2 illustrates a suitable reactive monomer of the present invention.

Figure 3 illustrates the photoinitiator of the present invention.

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.

Figure 11 illustrates the molecular structure of the single isosorbide group dopants (IS-1) and (IS-2) of the comparative examples.

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.

Claims (14)

A blue phase liquid crystal composition comprising: a reactive monomer comprising at least one reactive vinyl bond and having a total blue phase liquid crystal composition of 1% to 20% by mole; a photoinitiator having all blue Phase liquid crystal composition 0.1% to 3% molar percentage: a blue phase liquid crystal material having a total blue phase liquid crystal composition of 50 to 90% molar percentage, wherein the blue phase liquid crystal material is a biphenyl type compound; An optically chiral dopant having a percentage of 1% to 10% moles of all blue phase liquid crystal compositions, and a structural formula (I) as shown below: Wherein C ₁ and C ₂ are each independently a soft chain comprising 1 to 12 carbons which are substituted or unsubstituted; Ar ₁ , Ar ₂ , Ar 3 and Ar ₄ are respectively a cyclic linking group; G ₁ , G ₂ , G ₃ and G ₄ are each a monovalent substituent of Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ , and include at least two groups of substituents of Ar ₁ G ₁ , ₁ , ₂ , ₂ Combination, wherein Ar1, Ar2, Ar3, and Ar4 are each independently one of an aromatic ring, a heterocyclic ring, and an alicyclic hydrocarbon, and have G1, G2, G3, and G4 substituents, respectively; m and x are not 0, n, respectively. y is not 0 at the same time, the values of x and y are independently 0~4, and the values of m and n are independently 0~4: p, q, r, s are respectively positive integers selected from 1~4; B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , and B ₆ are each independently a divalent substituted or unsubstituted linking group; and A is substituted or unsubstituted with 1 to 12 carbons. Replace the soft chain linkage. A blue phase liquid crystal composition according to claim 1, wherein the A linking group is an alkyl group having 1 to 12 carbon chains and an alkoxyl having 1 to 12 carbon chains. The blue phase liquid crystal composition of claim 1, wherein B ₁ and B ₂ are each independently selected from the group consisting of -COO-, -OOC-, -(C=O)- and -CH ₂ . The blue phase liquid crystal composition of claim 1, wherein the B ₃ and B ₄ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ - -OCF ₂ -, -C=C-, alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-. The blue phase liquid crystal composition of claim 1, wherein the B ₅ and B ₆ linking groups are independently selected from the group consisting of -COO-, -OOC-, -N=N-, -C=N-, -CF ₂ - -OCF ₂ -, -C=C-, alkynyl, -(C=O)-, -CH ₂ - and -(S=O)-. The blue phase liquid crystal composition of claim 1, wherein C ₁ and C ₂ are each independently an alkyl group and an alkoxyl group. The blue phase liquid crystal composition of claim 1, wherein Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are each independently selected from the group consisting of a phenylene group, a pyridyl group, a cyclohexyl group, and a piperazine group. . The blue phase liquid crystal composition of claim 1, wherein the G ₁ , G ₂ , G ₃ and G ₄ substituents are each independently selected from the group consisting of H, F, Cl, Br and I. A blue phase liquid crystal composition according to claim 1, wherein the biphenyl type compound comprises a molecular pentane biphenyl cyanide (5CB), 4'-(4-ethyl-cyclohexyl)-3,4-di Fluorine biphenyl (4'-(4-ethyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-propyl-cyclohexyl)-3,4-difluorobiphenyl (4'-( 4-propyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-pentyl-cyclohexyl)-3,4-difluorobiphenyl (4'-(4-pentyl-cyclohexyl)-3 , 4-difluoro-biphenyl). An optically active compound having a diisosorbide group, the structural formula (I) being as follows: As a chiral dopant having a cholesterol phase and a blue phase liquid crystal, the blue phase liquid crystal material is a biphenyl type compound, wherein C ₁ and C ₂ are independently substituted with 1 to 12 carbon atoms. Or unsubstituted soft chain; Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are each a cyclic linking group; G ₁ , G ₂ , G ₃ and G ₄ are Ar ₁ and Ar ₂ , respectively. a monovalent substituent of Ar ₃ and Ar ₄ , which comprises at least two sets of substituent combinations of Ar1/G1, Ar2/G2, Ar3/G3, and Ar4/G4, wherein Ar1, Ar2, Ar3, and Ar4 are each independently an aromatic ring, One of the heterocyclic ring and the alicyclic hydrocarbon has G1, G2, G3 and G4 substituents respectively; m and x are different at 0, n and y are different at 0, and the values of x and y are independently 0~ 4, and the values of m and n are independently 0~4: p, q, r, s are respectively positive integers independently selected from 1 to 4; B ₁ , B ₂ , B ₃ , B ₄ , B ₅ , B _{6 is} independently a divalent substituted or unsubstituted linking group; and A is a soft chain linking group comprising 1 to 12 carbons which are substituted or unsubstituted. An optically active compound according to claim 10, wherein the biphenyl type compound comprises the molecular pentyl biphenyl cyanide (5CB), 4'-(4-ethyl-cyclohexyl)-3,4-difluoro Benzene (4'-(4-ethyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-propyl-cyclohexyl)-3,4-difluorobiphenyl (4'-(4- Propyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-pentyl-cyclohexyl)-3,4-difluorobiphenyl (4'-(4-pentyl-cyclohexyl)-3,4 -difluoro-biphenyl). An optically active oligomer having a plurality of isosorbide groups, and the structural formula (II) is as follows: As a chiral dopant having a cholesterol phase and a blue phase liquid crystal, the blue phase liquid crystal material is a biphenyl type compound, wherein C ₁ and C ₂ are independently substituted with 1 to 12 carbon atoms. Or unsubstituted soft chain; Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are each a cyclic linking group; G ₁ , G ₂ , G ₃ and G ₄ are Ar ₁ and Ar ₂ , respectively. a monovalent substituent of Ar ₃ and Ar ₄ , which comprises at least two sets of substituent combinations of Ar1/G1, Ar2/G2, Ar3/G3, and Ar4/G4, wherein Ar1, Ar2, Ar3, and Ar4 are each independently an aromatic ring, One of the heterocyclic ring and the alicyclic hydrocarbon has G1, G2, G3 and G4 substituents respectively; m and x are different at 0, n and y are different at 0, and the values of x and y are independently 0~ 4, and the values of m and n are independently 0~4: p, q, r, s are respectively positive integers independently selected from 1 to 4; k is a positive integer; B ₁ , B ₂ , B ₃ , B ₄ And B ₅ and B ₆ are each independently a divalent substituted or unsubstituted linking group; and the A linking group is a soft chain containing 1 to 12 carbons which are substituted or unsubstituted. An optically active oligomer according to claim 12, wherein the value of k is selected from the group consisting of 2, 3 and 4. An optically active oligomer according to claim 12, wherein the biphenyl type compound comprises a molecular pentane biphenyl cyanide (5CB), 4'-(4-ethyl-cyclohexyl)-3,4-di Fluorine biphenyl (4'-(4-ethyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-propyl-cyclohexyl)-3,4-difluorobiphenyl (4'-( 4-propyl-cyclohexyl)-3,4-difluoro-biphenyl), 4'-(4-pentyl-cyclohexyl)-3,4-difluorobiphenyl (4'-(4-pentyl-cyclohexyl)-3 , 4-difluoro-biphenyl).