WO2010053298A2 - 유방성 크로모닉 액정 조성물, 유방성 크로모닉 액정 코팅막의 제조방법 및 그로 인해 제조된 유방성 크로모닉 액정 코팅막 - Google Patents
유방성 크로모닉 액정 조성물, 유방성 크로모닉 액정 코팅막의 제조방법 및 그로 인해 제조된 유방성 크로모닉 액정 코팅막 Download PDFInfo
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- WO2010053298A2 WO2010053298A2 PCT/KR2009/006474 KR2009006474W WO2010053298A2 WO 2010053298 A2 WO2010053298 A2 WO 2010053298A2 KR 2009006474 W KR2009006474 W KR 2009006474W WO 2010053298 A2 WO2010053298 A2 WO 2010053298A2
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- liquid crystal
- basic
- coating film
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- chromic
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- XHKSJRJFBBOFAM-UHFFFAOYSA-N CC(C1=NCCN1)=C Chemical compound CC(C1=NCCN1)=C XHKSJRJFBBOFAM-UHFFFAOYSA-N 0.000 description 1
- MICFFQQEPUDELQ-UHFFFAOYSA-N CC1c(cccc2)c2C=CC1NC(c(cc1)c(C)cc1C(Nc1c(C)c(cccc2)c2cc1)=O)=O Chemical compound CC1c(cccc2)c2C=CC1NC(c(cc1)c(C)cc1C(Nc1c(C)c(cccc2)c2cc1)=O)=O MICFFQQEPUDELQ-UHFFFAOYSA-N 0.000 description 1
- 0 CC=C(C(*=*c(cc(**C(c1ccc(*C(C)=C(C)*2)c2c1)O)cc1)c1[N+]([I-]=C)=O)=CC*[N+]([I-]=C)=O)O Chemical compound CC=C(C(*=*c(cc(**C(c1ccc(*C(C)=C(C)*2)c2c1)O)cc1)c1[N+]([I-]=C)=O)=CC*[N+]([I-]=C)=O)O 0.000 description 1
- RMVFWEPIQRELCM-UHFFFAOYSA-N CCC(C)C1=C(OCC[NH+2]C)O1 Chemical compound CCC(C)C1=C(OCC[NH+2]C)O1 RMVFWEPIQRELCM-UHFFFAOYSA-N 0.000 description 1
- DPITVBFDGNZEKN-UHFFFAOYSA-O Cc(cc(cc1)C(Nc2c(C)c(cccc3)c3c3c2CCC=C3)=O)c1C([NH2+]c1c(C)c(cccc2)c2c2ccccc12)=O Chemical compound Cc(cc(cc1)C(Nc2c(C)c(cccc3)c3c3c2CCC=C3)=O)c1C([NH2+]c1c(C)c(cccc2)c2c2ccccc12)=O DPITVBFDGNZEKN-UHFFFAOYSA-O 0.000 description 1
- LZKUACINTXXPKB-UHFFFAOYSA-N OS(c(cc1)cc(c2ccccc22)c1cc2Br)(=O)=O Chemical compound OS(c(cc1)cc(c2ccccc22)c1cc2Br)(=O)=O LZKUACINTXXPKB-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3475—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing at least three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3477—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
- C09K19/348—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom containing at least two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3016—Polarising elements involving passive liquid crystal elements
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
- G02F1/133633—Birefringent elements, e.g. for optical compensation using mesogenic materials
Definitions
- the present invention relates to a mammary chromic liquid crystal composition, a method for manufacturing a mammary chromic liquid crystal coating film, and a mammary chromic liquid crystal coating film produced thereby, and more particularly, to a liquid crystal display device (LCD)
- LCD liquid crystal display device
- chromic liquid crystals A composition for producing a mammary chromic liquid crystal composition having a high hardness and improved coagulation stability between liquid crystals using the composition, and a mammary chromic liquid crystal coating film having high hardness and improved coagulation stability between liquid crystals using the composition. It relates to a method and a mammary chromic liquid crystal coating film produced thereby.
- a polarizing film and a retardation film are used in combination with an optical film to induce various polarization characteristics.
- an azo dye for example, direct blue or direct red
- a dichroic dye instead of iodine
- azo dye can secure durability, but is substantially inferior to the iodine dye.
- dichroism there exists a limit in expressing favorable optical characteristics.
- Japanese Patent No. 3174367 and the like combine a lambda / 4 phase difference film and a lambda / 2 phase difference film formed by stretching a modified cellulose film, a modified polycarbonate film, etc.
- An example of laminating an optical compensation film or a retardation film on a polarizing plate has been proposed, but the optical axis of the retardation film made of the stretched film as described above is changed according to the stretching direction.
- each film should be cut out and laminated in accordance with the direction of each optical axis, and the films should be laminated so that the absorption axis and the retardation axis are at preferred angles. More specifically, the absorption axis of the polarizing plate is generally parallel to the stretching direction thereof, and the retardation axis of the retardation film is also parallel to the stretching direction thereof. Therefore, in order to laminate the polarizing plate and the retardation film at, for example, an angle of 45 ° between the absorption axis and the slow axis, one of the films must be cut out in the direction of 45 ° with respect to the stretching direction of the film. When the film is cut and glued in this way, for example, the angle between the optical axes is changed for all the cut films, and the quality of all the products is changed, which causes a problem of costly and time-consuming manufacturing of the product. .
- US Pat. Nos. 2,400,877 and US 2,544,659 apply a solution of a dichroic material to a base film and evaporate the solvent from the applied surface to transform the dichroic material into a nematic phase, while at the same time a molecule of the material.
- a method of solidifying by orienting in a direction is shown.
- the dichroic nematic material is a water or alcohol soluble organic dye, which is converted into a nematic phase on the surface of the base film.
- Liquid crystal means that molecules have an orientative order in the long-range, while positional order is reduced (one-dimensional position on the static) Refer to a state of matter that exhibits absent (nematic phase) characteristics.
- liquid crystal Due to this intermediate order of liquid crystal, liquid crystal is defined as a material positioned between a crystalline solid having an even positional and directional order and an isotropic fluid having no order. Solid crystals or isotropic fluids can be transformed into the liquid crystal phase by changing the temperature or by changing the concentration by adding a suitable solvent. Commonly, a liquid crystal formed by temperature change, such as the former, is called a thermotropic liquid crystal, and a liquid crystal formed by concentration, such as the latter, is called a lyotropic liquid crystal.
- the orientation method of a thermotropic liquid crystal is based on the fixation of a liquid crystal compound by the process to the specific direction of a base film.
- This treatment is disclosed in US Pat. No. 5,596,434.
- a base film is applied
- a base film is processed by the method of mechanically rubbing.
- the rubbing direction determines the alignment direction of the thermotropic liquid crystal.
- the alignment phenomenon between the anisotropic base film and the liquid crystal array is referred to as "anchoring", and the alignment method by surface anchoring is commonly used in display devices using thermotropic liquid crystals.
- anchoring The alignment phenomenon between the anisotropic base film and the liquid crystal array is referred to as "anchoring"
- the alignment method by surface anchoring is commonly used in display devices using thermotropic liquid crystals.
- the surface is treated with a polymer or surfactant to obtain the desired orientation properties.
- the alignment of the breast liquid crystal has a side that is more difficult than the alignment of the thermotropic liquid crystal. This is because most breast-like liquid crystals are made of amphiphilic materials having both hydrophilicity and hydrophobicity.
- Amphoteric molecules have a polar (hydrophilic) head and a nonpolar (hydrophobic) aliphatic chain tail. When these amphoteric molecules are in contact with the base film, they are generally arranged in a direction perpendicular to the plane of the base film due to the amphoteric properties of the liquid crystal. This orthogonal orientation means that the optical axis is orthogonal to the base film.
- the concentration and structure of a specific molecule have a great influence in determining the arrangement order of liquid crystals.
- Common lyotropic liquid crystals have a long columnar shape mainly made of rod-shaped or stacked or plate-shaped molecules.
- LCLC lyotropic chromonic liquid crystal
- LCLCs unlike conventional mammary liquid crystals, which are flexible, have an ionic functional group at one end of a rod-like aliphatic chain molecule, and are made of an amphoteric material, have a hydrophilic or hydrophilic structure around a hard, plank-shaped aromatic molecule. It has a structure with an ionic functional group.
- the LCLC is widely used in dyes, pharmaceuticals, nucleic acids, antibiotics, anticancer agents and the like.
- the molecular structure and macrostructure of the LCLC are as shown in FIGS. 1 and 2. That is, as shown in Figure 1, in the aqueous solution, the head portion of the hydrophilic group (1) is directed to the outside, the tail portion of the hydrophobic group (2) is aggregated (aggregated), have a micellar structure (micellar), or As shown in Fig. 2, molecules having the hydrophilic group 3 attached to the planar aromatic hydrophobic core 4 are laminated. This is called self-assembly, and this self-assembly has a stable orientation characteristic, attracting attention as a material used in various optical elements.
- the stacked structure between the molecules is formed by the ⁇ - ⁇ interaction between the aromatic cores 4.
- J. Lydon, Chromonics: Handbook of Liquid Crystals (Wiley-VCH, Weinheim, 1998) v. 2B, p. 981 and Current Opin. Col. Inter. Sci. 3, 458 (1998)] is also water soluble due to hydrophilic ionic functionality around the molecule.
- US Pat. No. 5,948,487 or International Patent PCT / US2000 / 031181 discloses structures oriented using nematic chromic liquid crystal materials containing one or more triazine groups
- US Pat. No. 6,570,632 A method is disclosed in which a chromonic material comprising chromoline (C 23 H 14 O 11 Na 2 ) is applied onto a glass substrate, rubbed and oriented, and dried to remove the solvent to obtain an optical film.
- the alignment structure of the optical film manufactured by this method is as shown in FIG. 3.
- the oriented optical film has a structure in which the molecular plane of the LCLC 13 is aligned on the YZ plane, and the long axis of the LCLC 13 molecules is aligned in the Y-axis direction on the base film 11.
- the molecular planes of some molecules are not perfectly aligned on the YZ plane, or that the long axis of the LCLC 13 molecules is aligned out of the Y axis direction.
- the alignment structure of the optical film produced by the method is as shown in FIG.
- a poly cation 12 is coated on a base film 11 made of glass or mica, and an aqueous solution of violet 20 (13), which is a kind of anionic LCLC, has a mechanical shearing force in the X-axis direction.
- violet 20 13
- the unnecessary structures are washed, removed, and dried to maintain the lamination structure of the chromonic liquid crystals electrostatically stacked on the dried film.
- the polycation 12 and the anionic LCLC 13 are repeatedly repeated several times in the base film 11 to obtain a stacked structure.
- the present invention is to solve the above problems, an object of the present invention, by using a monomer instead of an aqueous solution used in the chromic liquid crystal composition, orienting it, and then curing with a monomer without drying step, A method for producing a breast chromic liquid crystal composition and a breast chromic liquid crystal coating film which increases the bond strength between molecular aggregates and between the aggregates and the base film to obtain an optical film having a high surface hardness and no cracking after drying. And to provide a mammary chromic coating film thus produced.
- the mammary chromonic liquid crystal composition according to the present invention comprises each chromic liquid crystal compound and a monomer having acid-base characteristics opposite to each other. That is, a basic chromonic liquid crystal compound having a basic functional group and an acidic monomer having an acidic functional group; Or an acidic chromonic liquid crystal compound having an acidic functional group and a basic monomer having a basic functional group.
- the mammary chromonic liquid crystal composition according to the present invention is a cation (or anion) of a basic functional group (or an acidic functional group) surrounding an aromatic hydrophobic core of a chromonic liquid crystal compound, and as a counter-ion thereto.
- anion (or cation) of an acidic monomer (or basic monomer) interacts to produce a mammary chromic liquid crystal having a new functional group, and when the composition is cured, the liquid crystal is reacted by a polymerization reaction by the new functional group. It is possible to strengthen the bonds between the respective molecular aggregates forming the laminated structure in the dye and the bond between the molecular aggregates and the base film, thereby achieving excellent mechanical, optical, and electrical properties of the formed film.
- the chromonic liquid crystal compound has a form in which a hydrophilic functional group is surrounded around a rigid, plank-shaped aromatic molecule (hydrophobic core).
- basic chromic liquid crystal compound or the “acidic chromic liquid crystal compound” used in the present invention, those having basic or acidic hydrophilic functional groups bonded to the hydrophobic core, respectively, are used.
- a basic hydrophilic functional group hereinafter referred to as a "basic functional group” or an acidic hydrophilic functional group (hereinafter referred to as an “acidic functional group”), when reacted with an acidic monomer and a basic monomer described below, respectively,
- the functional groups bear cations
- the acid functional groups bear anions, respectively, which are ionically bound to the anions of the acidic monomers or to the cations of the basic monomers, and the bound monomers polymerize with additional monomers present in the composition, resulting in a mastogenicity.
- a solid bond between the molecular aggregates stacked as a liquid crystal is achieved.
- Such chromonic liquid crystal compounds are described in J. Lydon, Chromonics: Handbook of Liquid Crystals (Wiley-VCH, Weinheim, 1998) v. 2B, p. 981 and Current Opin. Col. Inter. Sci. 3, 458 (1998)], T. Sergan et al .: Liquid Crystals v. 5, pp. 567-572 (2000), wherein the basic (or acidic) functional group forms the aromatic ring (hydrophobic core) Will have.
- the "basic functional group” refers to a functional group directly contacting an aromatic ring, and is not particularly limited as long as it is a basic functional group, but mainly an amine group, an imine group, an amide group, an azide group, a nitrate group or an ammonium group And a functional group in which nitrogen ions (N + ) are expressed upon reaction with an acidic monomer.
- the basic functional group is generally present in the form of an amine group, an imine group, or the like as described above, or the nitrogen ions (N + ) and other anions are bonded to exist in the form of salts, which are described later. When reacted with, the nitrogen ions (N + ) are exposed to bond with the anions of the acidic functional groups of the acidic monomers.
- the basic chromonic liquid crystal compound is as shown in the following formulas (I-1) to (I-11). However, the basic chromonic liquid crystal compound is not limited to the following chemical formula.
- R is an alkyl group or a hydrogen atom
- A is Cl
- Me is either an alkyl group including a methyl group
- HCOO a halogen atom
- the term “acidic functional group” herein refers to a functional group directly contacting an aromatic ring, and is not particularly limited as long as it is an acidic functional group, but the carboxylate (COO ⁇ ) ion mainly reacts with a basic monomer described below. Salts, ester groups, carboxyl groups of COO -to be expressed; Phosphate, phosphine group, phosphate group, phosphonic acid group in which phosphate ions (PO 3 ⁇ ) are expressed during the reaction; And sulfonic acid and sulfonic acid groups in which sulfonic acid ions (SO 3 ⁇ ) are expressed during the reaction.
- the acidic functional group is generally present in the form of an ester group, a phosphine group, a sulfonic acid group, or the like as described above, or the carboxylate (COO ⁇ ) ion and the like, H + , NH 4 + , Li + , Na + , K +
- Other cations, such as, Cs + are present in the form of salts, and when reacted with a basic monomer described later, the anion is exposed to bond with a cation of an acidic functional group of the monomer.
- acidic chromonic liquid crystal compounds are as shown in the following formulas (II-1) to (II-23).
- the acid chromic liquid crystal compound is not limited to the following chemical formula.
- R is an alkyl group or a hydrogen atom
- n 1 to 3
- X is hydrogen or a halogen atom
- Me is an alkyl group including a methyl group
- Formulas II-12 to II C at -23 is a cation such as H + , NH 4 + , Li + , Na + K + , and the like.
- the basic or acidic chromonic liquid crystal compound is preferably contained in 3 to 40% by weight, preferably 5 to 30% by weight based on the total composition.
- the content range of the basic or acidic chromonic liquid crystal compound is a preferred range for the liquid crystal composition to exist with the characteristics of the liquid crystal between the solid crystal and the isotropic fluid.
- an acidic or basic monomer is used instead of an aqueous solution, respectively, in the case of acidic monomo, the basic functional group of the basic chromonic liquid crystal compound, and in the case of the basic monomer, the acid functional group and strong ions of the acidic chromonic liquid crystal compound.
- the liquid crystal when the composition is mixed in a combination containing the acidic chromonic liquid crystal compound and the basic monomer, the liquid crystal is further contained through water because of the influence of the sulfone group of the acidic chromonic liquid crystal compound. More preferably, a process of dispersing the compound and the monomer and then removing the water is carried out.
- the "acidic monomer” used in the present invention is not particularly limited as long as the monomer has an acidic functional group corresponding to the basic functional group of the basic chromonic liquid crystal compound, and the carboxylate when reacted with the basic chromonic liquid crystal compound ( COO-acrylate-based monomer include salts, ester group, a carboxyl group, such as -) ions are expressed COO; Monomers including a phosphate, phosphine group, phosphate group, phosphonic acid group, etc.
- n 0 to 3.
- A is hydrogen, an alkali metal cation or primary to quaternary ammonium cation.
- A is hydrogen, an alkali metal cation or primary to quaternary ammonium cation.
- A is hydrogen, an alkali metal cation or primary to quaternary ammonium cation.
- the "basic monomer” used in the present invention is not particularly limited as long as it is a monomer having a basic functional group corresponding to the acidic functional group of the acidic chromonic liquid crystal compound. It refers to a functional group which expresses a nitrogen ion (N + ) such as a cation, mainly an amine group, an imine group, an amide group, an azide group, a nitrate group or an ammonium group during the reaction.
- N + nitrogen ion
- Representative basic monomers include dialkylaminoalkylacrylates and methacrylates and quaternary or acid salts thereof (eg DMAEA, MAQ), dialkylaminoalkylacrylamides and methacrylamides and quaternary or acid salts thereof, N, N Diallylamine and its ammonium salt, diaryldimethylammonium chloride (DADMAC), Mannich products, and the like, but are not limited to these.
- Alkyl groups are generally C1-4 alkyl.
- the mammary chromic liquid crystal composition according to the present invention may further include a polymerization initiator such as a photoinitiator and a thermal initiator for facilitating polymerization after the alignment with the chromonic liquid crystal compound and the monomer.
- a polymerization initiator such as a photoinitiator and a thermal initiator for facilitating polymerization after the alignment with the chromonic liquid crystal compound and the monomer.
- the photoinitiator used in the present invention is used in the case of photopolymerizing the composition by ultraviolet light, specifically, diethoxyacetphenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 1 Acetphenones, such as -hydroxycyclohexyl phenyl ketone and 2-methyl-2-morphine (4-thiomethylphenyl) propane-1-one, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzo Benzoin ethers such as phosphorus isobutyl ether, benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfonic acid, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl] benzophenones such as
- amine compounds such as N, N- dimethyl paratoluidin, and 4, 4'- diethylamino benzophenone, can also be used individually or in mixture.
- thermal initiator when thermally polymerizing the mammary chromonic liquid crystal composition according to the present invention, a thermal initiator is used.
- organic peroxide free radical initiators such as diacyl peroxides, peroxy ketals, ketone peroxides, hydroperoxides, dialkyl peroxides, peroxy esters, and peroxydicarbonates can be used.
- lauroyl peroxide, benzoyl peroxide, cyclohexanone peroxide, 1,1-bis (t-butylperoxy) 3,3,5-trimethylcyclohexane, t-butylhydroperoxide and the like May be mentioned.
- a combination of persulfate / bisulfite can be used.
- the content of the polymerization initiator is preferably in the range of 0.01 wt% to 10 wt%, more preferably 0.5 wt% to 5 wt%, in 100 wt% of the composition. If the content of the polymerization initiator is less than 0.1% by weight, it is difficult to obtain a polymerization effect. If the content of the polymerization initiator is more than 10% by weight, too much polymerization initiator is added as compared to the polymerization initiation effect, resulting in low economic efficiency.
- the mammary chromic liquid crystal composition used in the present invention may further include an additive in some cases, and may be added a solvent such as an organic solvent and water to facilitate viscosity control.
- the additives include a nonionic vinyl monomer added to enable copolymerization with the monomer to control the physical properties of the prepared thin film, a leveling agent to increase the smoothness of the composition, and a surface tension of the composition.
- Wetting agents, ultraviolet stabilizers, heat stabilizers, conductive surfactants, crosslinking monomers, anti-aging agents, denaturing agents or other materials for improving the wettability of the base film may be included.
- the conductive surfactant quaternary ammonium is preferable.
- the nonionic vinyl monomer is a copolymerizable nonionic ethylenically unsaturated monomer well known in the art.
- Preferred nonionic vinyl monomers are compounds represented by the following formula (V) or (VI).
- X is H or methyl;
- Z is -C (O) OR 1 , -C (O) NH 2 , -C (O) NHR 1 , -C (O) N (R 1 ) 2 , -C 6 H 4 R 1 , -C 6 H 4 OR 1 , -C 6 H 4 Cl, -CN, -NHC (O) CH 3 , -NHC (O) H, N- (2-pyrrolidonyl), N-caprolactamyl, -C (O ) NHC (CH 3 ) 3 , -C (O) NHCH 2 CH 2 , -N-ethyleneurea, -SiR 3 , -C (O) O (CH 2 ) xSiR 3 , -C (O) NH (CH 2 ) xSiR 3 or-(CH 2 ) xSiR 3 ;
- x is an integer from 1 to about 6;
- Each R is independently
- Suitable water insoluble nonionic vinyl monomers include C 1 -C 30 alkyl (meth) acrylates; C 1 -C 30 alkyl (meth) acrylamide; Styrene; Substituted styrenes such as vinyl toluene (ie 2-methylstyrene), butyl styrene, isopropyl styrene, p-chlorostyrene and the like; Vinyl esters such as vinyl acetate, vinyl butyrate, vinyl caprolate, vinyl pivalate, vinyl neodecanoate, and the like; Unsaturated nitriles such as methacrylonitrile, acrylonitrile and the like; And unsaturated silanes such as trimethylvinylsilane, dimethylethylvinylsilane, allyldimethylphenylsilane, allyltrimethylsilane, 3-acrylamidopropyltrimethylsilane, 3-trimethylsily
- nonionic vinyl monomers include C 1 -C 18 alkyl esters of acrylic acid and methacrylic acid, methacrylic amidoethyl-N-ethylene urea and combinations thereof.
- crosslinking monomer examples include a diamine monomer, an acrylic polyfunctional monomer, an epoxy crosslinking agent, a metal chelate crosslinking agent, a silane crosslinking agent, an aldehyde, an N-methylol compound, a dioxane derivative, and a compound acting by activating a carboxyl group.
- a phenol type compound, an amine compound, an organic sulfur type compound, a phosphine type compound is mentioned, for example.
- glycols, silicones, and alcohols are mentioned, for example.
- the said surfactant is used in order to make the surface of an optical film smooth, for example, Surfactant, such as a silicone type, an acryl type, and a fluorine type, is mentioned as a specific example.
- liquid crystal composition may include various additives used in manufacturing a conventional photoresist, a monomer for crosslinking, and the like.
- solvent water may be used.
- Organic solvents such as alcohols, acetates, ethers, glycols, ketones, and carbonates, dimethyl formaldehyde (DMF), dimethyl sulfoxide (DMSO), Any one of aprotic polar organic solvents such as N-methylpyrrolidone (NMP) and N, N-dimethylacetamide (DMAc) may be used alone or in combination of two or more thereof, preferably dimethyl formaldehyde. (DMF) or methanol is used alone or in combination.
- NMP N-methylpyrrolidone
- DMAc N-dimethylacetamide
- the addition amount of such an additive and a solvent, in the case of a chromic liquid crystal composition having basic It is preferable to add 0.01-40 weight% with respect to 100 weight% of compositions, More preferably, 0.1-35 weight% is added.
- the chromic liquid crystal composition having acidity it is preferable to add 0.1 to 80% by weight, more preferably 40 to 80% by weight.
- the manufacturing method of the mammary chromic liquid crystal coating film according to the present invention includes the mammary chromic liquid crystal composition described above, that is, each chromic liquid crystal compound and a monomer having acid-base characteristics opposite to each other, wherein the photoinitiator and A coating step of coating on the base film a breast chromic liquid crystal composition further comprising a polymerization initiator consisting of at least one of ten initiators; An alignment step of aligning a coating film made of the breast chromic liquid crystal composition; It comprises a curing step of curing the coating film by thermal polymerization or photopolymerization.
- the manufacture of a thin liquid crystal film having anisotropic properties is an important field to be treated as an important application area of chromic liquid crystals.
- the chromic liquid crystal composition used in the present invention is applied to a base film, and then cured to form a solid film, thereby having properties useful as a polarizing plate, an optical compensation film, a retarder, an alignment film, a color filter, and the like.
- the present invention there is a strong cohesive stability at the molecular unit as "curing by polymerization", such as photopolymerization or thermal polymerization, to a monomer included in the composition, preferably without a drying step for removing water contained in the aqueous solution. Since the optical element having excellent mechanical, optical and electrical properties can be obtained.
- curing by polymerization such as photopolymerization or thermal polymerization
- the coating step is composed of chromic liquid crystal compounds and ionic monomers having acid-base characteristics opposite to each other as a main raw material, and as a polymerization initiator, a composition further comprising a photoinitiator and / or a thermal initiator is mixed. It is a step of applying on the base film.
- a cation (or anion) of a basic (or acidic) functional group surrounding an aromatic hydrophobic core of a chromonic liquid crystal compound and an anion (or cation) of an acidic (or basic) monomer as a counter-ion thereto Acting to produce a mammary chromic liquid crystal having a new functional group, and when curing the composition, the bonds between the respective molecular aggregates and the molecules forming a laminated structure in the liquid crystal dye by polymerization by the new functional group.
- the bond between the aggregate and the base film can be strengthened, and thus the excellent mechanical, optical and electrical properties of the formed film can be achieved.
- composition when hardening the said composition using photopolymerization using an ultraviolet-ray, etc., when hardening
- the coating method in the coating step is spin coating (dip coating), dip coating (Dip coating), flow coating (Flow coating), spray coating (Roll coating), gravure coating (Gravure Coating)
- any one of micro-gravure coatings may be used.
- an anisotropic film such as glass or mica or triacetyl cellulose (TAC) may be used, and as a hydrophobic transparent resin film, poly (polyethylene terephthalate (PET), polyethylene naphthalate or the like)
- PET polyethylene terephthalate
- PMMA polymethylmethacrylate
- styrene polymers such as polystyrene and an acrylonitrile- styrene copolymer
- a polycarbonate polymer can be used without limitation.
- the alignment step in the present invention is a step of aligning or aligning a coating film made of the mammary chromic liquid crystal composition in a predetermined direction.
- the orientation method can use a variety of well-known methods, such as using a strong magnetic field, using an alignment film, or using a shear force (shear).
- a method of rubbing the surface of the base film or photoaligning a polymer having a photoactive group such as azobenzene may be used to prepare an alignment film.
- a liquid crystal cell using a chromonic liquid crystal on a plate N phase or twisted chiral nematic (N *) may be utilized as a phase difference film having negative birefringence.
- N * twisted chiral nematic
- the nonionic polymer coating film having an azobenzene functional group After treating the nonionic polymer coating film having an azobenzene functional group by linearly polarized light to form an alignment film, it may be followed by a method of coating the chromic liquid crystal composition thereon.
- the shear force alignment method is performed by coating a composition on a base film in a state of having a mammary liquid crystal phase and then applying a shear force on the composition coating film so that the axis of the chromonic liquid crystal molecules is oriented perpendicular to the direction in which the shear force is applied. do.
- the composition containing the photoinitiator may be applied and oriented, and then, may be cured at room temperature or cold under ultraviolet irradiation, and in the case of thermal polymerization, the composition containing the thermal initiator is applied and oriented. And at a high temperature exceeding 100 ° C. for 10 minutes to 10 hours to cure the composition.
- the photopolymerization or thermal polymerization may be generally used without any limitation as long as it is a method capable of curing the monomer by curing it.
- the mammary chromonic liquid crystal composition includes a combination of an acidic chromonic liquid crystal compound, a basic monomer, and a polymerization initiator, in addition to the combination, a composition containing water is used. It is more preferable.
- the acid chromonic liquid crystal compound is dispersed in the basic monomer having water solubility through water in the coating step, and after the coating step, further comprising a drying step of removing the water. It is preferable.
- Any of the acrylic acid having an acrylic group (denoted by reference numeral “20” hereinafter) is mixed and reacted to form a unit molecular aggregate formed after polymerization is performed using a composition comprising molecules bonded in the form of the formula (VII-3).
- the chromic liquid crystal molecule 10 and the acrylic acid in the form of a disc are reacted by an acid-base reaction, as shown in Formula VII-3.
- (20) is dissolved in an excess of acrylic acid (20) in the form of a salt (salt) in the form of a mammary liquid crystal phase, while being laminated by self-organization of chromic liquid crystal molecules
- the acrylic acid 20 bonded to the hydrophobic core 10 in the form shown in FIG. 6 and the external acrylic acid 20 not bonded to the hydrophobic core 10 are polymerized together. Strong bonding structures 20 'are formed between the molecular aggregate layers.
- FIG. 7 is a view showing a polarizing film formed by the composition. That is, the chromic liquid crystal molecules 10 and the polymerized acrylic acid bonding structure 20 'are self-assembled and aligned on the base film 100.
- the liquid crystal film thus prepared may be used as an optical film and the like, and a brief description will be made of an embodiment of a method of manufacturing a micro patterned polarizer, which has recently been studied.
- Micro-patterns of anisotropic aromatics have been studied using the self-assembly of chromic liquid crystals, and the micro-pattern polarizers manufactured therefrom are used in holographic films and microelectronic fields using optical materials whose image changes depending on the viewing angle. , And stereoscopic imaging.
- FIG. 8 is a view sequentially showing an embodiment of a method of manufacturing the micro pattern polarizer.
- the composition 200 including the photocuring initiator according to the present invention on the base film 100 is oriented in a predetermined direction by the aforementioned shear force alignment method.
- the non-exposed portions other than the exposed and cured portions may be selectively converted to isotropic state to be removed, thereby performing an additional process (developing step) of manufacturing a micro pattern polarizer. That is, the selective isotropic state switching of the non-exposed part can be achieved by the following method. Since the non-exposed part is not cured, it is selectively removed by using a solubility-developing solution, or converted to an isotropic state again by changing the concentration due to evaporation of heat or acidic monomers, and then irradiating the entire remaining film with ultraviolet light, the exposed part is aligned. The non-exposed part is in an isotropic state in the obtained liquid crystal phase.
- a mammary chromonic liquid crystal composition comprising each chromic liquid crystal compound and a monomer having acid-base characteristics opposite to each other, curing by thermal polymerization or photo polymerization, rather than drying them.
- an optical element having excellent electrical and optical properties such as mechanical strength, insulation properties, and refractive index can be obtained.
- 3 to 5 are views showing a molecular structure and a lamination structure of a liquid crystal film formed according to a conventional method for manufacturing an optical device using LCLC.
- FIG. 6 is a view showing the structure of a unit molecular aggregate formed after polymerization is performed using a chromonic liquid crystal composition according to an embodiment of the present invention.
- FIG. 7 is a view showing a polarizing film formed by the composition of FIG.
- FIG. 8 is a view sequentially showing an embodiment of a method of manufacturing a micro-pattern polarizing element
- Red 2304 manufactured by Optiva
- Chemical Formula I-10 a basic chromonic liquid crystal compound on a glass substrate
- 0.01 ml of 2-carboxy ethyl acrylate of Chemical Formula III-3, and a photoinitiator as an acidic monomer ( Irgacure 907, manufactured by Ciba) 0.0025 g of the coating was mixed by spin coating, and then the coating film was rubbed in the longitudinal direction using a rubber plate, and applied by irradiating with light of 20 mJ / cm 2 using a metal halogen lamp. The liquid crystal coating film was cured to obtain a liquid crystal coating film having a thickness of 2 ⁇ m.
- a liquid crystal coating film was formed in the same manner as in Experimental Example 1 except that the composition was formed on the aqueous solution by mixing water instead of the acidic monomer. And the liquid crystal coating film formed by the said experiment example and the comparative example was scraped off by the ballpoint pen.
- a liquid crystal coating layer was formed in the same manner as in Experimental Example except that only water was used instead of the basic monomer to form a composition in an aqueous solution.
- 11 and 12 are photographs of the surfaces of the liquid crystal coating layer formed by Experimental Example 1 and Comparative Example 1, respectively.
- the liquid crystal coating layer formed by Experimental Example 1 hardly found surface cracks after orientation, but the liquid crystal coating layer formed by Comparative Example 1 had surface cracks (black cracked portions) in part. You can see what happens.
- the surface of the liquid crystal coating layer according to Experimental Example 1 and Experimental Example 2 the hardness of the pencil lead is black at 3H and HB or more, respectively, the liquid crystal according to Comparative Example 1 and Comparative Example 2 It can be confirmed that the surface of the coating layer changes black at 3B and 2B or more, respectively. Thereby, it can confirm that the liquid-crystal coating layer formed with the mammary chromonic liquid crystal composition by this invention is remarkably excellent in the surface hardness.
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Abstract
Description
상기 화학식 Ⅰ-1 내지 Ⅰ-11에서 R은 알킬기 또는 수소원자이며, A는 Cl, (Me는 메틸기를 포함한 알킬기) 또는 HCOO 중 어느 하나이며, X는 수소 또는 할로겐 원자(Cl, Br 등)이다.
Claims (13)
- 염기성 작용기를 가진 염기성 크로모닉 액정 화합물과 산성 작용기를 가진 산성 모노머; 또는 산성 작용기를 가진 산성 크로모닉 액정 화합물과 염기성 작용기를 가진 염기성 모노머를 포함하여 이루어진 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 염기성 크로모닉 액정 화합물은, 방향족 분자로 이루어진 소수성 코어의 주위에 염기성 작용기가 둘러싼 형태로 이루어지며, 상기 산성 크로모닉 액정 화합물은, 방향족 분자로 이루어진 소수성 코어의 주위에 산성 작용기가 둘러싼 형태로 이루어진 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 유방성 크로모닉 액정 조성물 100중량%에 있어서, 상기 염기성 크로모닉 액정 화합물 또는 상기 산성 크로모닉 액정 화합물은 3 내지 40중량%인 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 염기성 크로모닉 액정 화합물 및 상기 염기성 모노머의 염기성 작용기는, 각각 상기 산성 모노머 및 상기 산성 크로모닉 액정 화합물과 반응시, 질소 이온(N+)을 발현하는 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 산성 모노머 및 상기 산성 크로모닉 액정 화합물의 산성 작용기는, 각각 상기 염기성 크로모닉 액정 화합물 및 상기 염기성 모노머와 반응시, 카르복실레이트(COO-)이온, 인산 이온(PO3 -), 술폰산 이온(SO3 -) 중 적어도 하나를 발현하는 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 유방성 크로모닉 액정 조성물은, 광개시제, 열개시제 중 적어도 하나로 이루어진 중합개시제를 더 포함하는 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제6항에 있어서,상기 중합개시제는, 상기 유방성 크로모닉 액정 조성물 100중량%에 있어서, 0.01 내지 10중량%인 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항에 있어서,상기 유방성 크로모닉 액정 조성물 100중량%에 대하여, 비이온성 비닐모노머, 물, 유기용매, 가교용 모노머, 레벨링제, 습윤제, 자외선 안정제, 도전성 계면활성제 중 적어도 하나를 0.01 내지 80 중량% 포함하는 것을 특징으로 하는 유방성 크로모닉 액정 조성물.
- 제1항 내지 제8항 중 어느 한 항에 의한 유방성 크로모닉 액정 조성물을, 기재필름 위에 코팅하는 도포단계;상기 유방성 크로모닉 액정 조성물로 이루어진 코팅막을 배향하는 배향단계;상기 코팅막을 열 중합 또는 광 중합에 의하여 경화시키는 경화단계를 포함하는 유방성 크로모닉 액정 코팅막의 제조방법.
- 제9항에 있어서,상기 유방성 크로모닉 액정 조성물은,산성 크로모닉 액정 화합물과, 염기성 모노머, 중합개시제 및 물을 포함하여 이루어지며,상기 도포단계 이후에, 상기 물을 제거하는 건조단계를 더 포함하는 것을 특징으로 하는 유방성 크로모닉 액정 코팅막의 제조방법.
- 제9항에 있어서,상기 경화단계는,상기 코팅막 위에 포토마스크를 위치시키고, 자외선 조사에 의해 상기 코팅막을 선택적으로 경화시킨 후, 상기 포토마스크를 제거하여 이루어지며,상기 경화단계 이후에, 상기 경화단계에서 경화되지 아니한 부분을 제거하거나 열 또는 증발의 방법으로 경화되지 않은 부분을 광학 이방성 상태로 처리한 후 자외선 조사를 통해 경화하는 제2경화단계를 더 포함하는 것을 특징으로 하는 유방성 크로모닉 액정 코팅막의 제조방법.
- 제9항에 있어서,상기 유방성 크로모닉 액정 코팅막을 배향하는 배향방법은, 강한 자기장을 이용하는 배향방법, 배향막을 이용하는 배향방법, 전단력(shear)을 이용하는 배향방법 중 어느 하나의 방법에 의하여 수행하는 것을 특징으로 하는 유방성 크로모닉 액정 코팅막의 제조방법.
- 제9항 내지 제12항 중 어느 한 항의 제조방법에 의하여 형성된 유방성 크로모닉 액정 코팅막.
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US13/127,940 US8580143B2 (en) | 2008-11-05 | 2009-11-05 | Lyotropic chromonic liquid crystal composition, method for manufacture of lyotropic chromonic liquid crystal coating film, and lyotropic chromonic liquid crystal coating film manufactured thereby |
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KR1020080109207A KR100988434B1 (ko) | 2008-11-05 | 2008-11-05 | 유방성 크로모닉 액정 조성물 |
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Also Published As
Publication number | Publication date |
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US8580143B2 (en) | 2013-11-12 |
US20110272629A1 (en) | 2011-11-10 |
WO2010053298A3 (ko) | 2010-08-19 |
JP5518886B2 (ja) | 2014-06-11 |
JP2012507619A (ja) | 2012-03-29 |
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