WO2010032591A1 - 重合性光学活性イミド化合物及び該化合物を含有する重合性組成物 - Google Patents
重合性光学活性イミド化合物及び該化合物を含有する重合性組成物 Download PDFInfo
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- WO2010032591A1 WO2010032591A1 PCT/JP2009/064801 JP2009064801W WO2010032591A1 WO 2010032591 A1 WO2010032591 A1 WO 2010032591A1 JP 2009064801 W JP2009064801 W JP 2009064801W WO 2010032591 A1 WO2010032591 A1 WO 2010032591A1
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- KWLNAVINMFSERI-NZCKGYRVSA-N C=CC(OCCCCCCOc1ccc(cc(cc2)C(O[C@H]([C@H](C(N3Cc4ccccc4)=O)OC(c(cc4)cc(cc5)c4cc5OCCCCCCOC(C=C)=O)=O)C3=O)=O)c2c1)=O Chemical compound C=CC(OCCCCCCOc1ccc(cc(cc2)C(O[C@H]([C@H](C(N3Cc4ccccc4)=O)OC(c(cc4)cc(cc5)c4cc5OCCCCCCOC(C=C)=O)=O)C3=O)=O)c2c1)=O KWLNAVINMFSERI-NZCKGYRVSA-N 0.000 description 1
- WCGFMNLZRSFWPX-XWQRBYOQSA-N CN(C([C@@H](C1OC(c(cc2)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)=O)OC(c(cc2)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)=O)=O)C1=O Chemical compound CN(C([C@@H](C1OC(c(cc2)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)=O)OC(c(cc2)ccc2OC(c(cc2)ccc2OCCCCCCOC(C=C)=O)=O)=O)=O)C1=O WCGFMNLZRSFWPX-XWQRBYOQSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
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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
- C09K19/06—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
- C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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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
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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
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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 novel polymerizable optically active imide compound, a polymerizable composition using the same, and a polymer obtained by photocuring the polymerizable composition. Specifically, a cyclic imide structure is used as an optically active site.
- the present invention relates to a polymerizable optically active imide compound having a (meth) acryloyloxy group as a polymerizable moiety, a polymerizable composition using the same, and a polymer.
- the polymer of the present invention is useful as an optical anisotropic body such as an optical compensator such as an optical polarizer, a retardation plate, and an N-type C plate, a visual compensation film, a brightness enhancement film, or a reflective film.
- liquid crystal display devices such as liquid crystal televisions and video camera monitors are required to have low power consumption and low voltage drive.
- optical properties such as retardation plates, polarizing plates, light polarizing prisms, and reflecting plates using the anisotropy of physical properties such as orientation, refractive index, dielectric constant, and magnetic susceptibility of liquid crystalline substances.
- a method of increasing the utilization factor of a light source and a method of improving the viewing angle characteristics of a liquid crystal display element by applying a rectangular parallelepiped are being studied.
- optical anisotropic bodies are obtained by a method of polymerizing by irradiating with an energy ray such as ultraviolet rays in a state in which a liquid crystal compound having a polymerizable site or a polymerizable composition containing a liquid crystal compound having a polymerizable site is aligned. It is done. That is, the obtained optical anisotropic body is a polymer that is immobilized while maintaining molecular orientation, and is a polymer that exhibits optical anisotropy due to the effect of the optically active site controlled in a higher order structure. It is.
- a helical structure is induced in the liquid crystal molecules, and the optical properties of the optical anisotropic body can be manipulated.
- the helical pitch length which is the periodic length of this helical structure, depends on the helical induction force (helical twisting power) inherent to the compound and the amount added.
- the optically active compound having a small helical induction force has a longer induced helical pitch length. Therefore, when it is desired to shorten the helical pitch length, it is necessary to add a large amount of the optically active compound.
- Patent Documents 1 to 7 the optically active compounds reported so far (for example, Patent Documents 1 to 7) have not been satisfactory.
- Patent Document 8 describes substituted tartarimide derivatives, but does not describe a compound having a polymerizable group.
- Patent Document 9 describes that a tartarimide derivative having a polymerizable group is introduced into an organosiloxane, but does not describe a compound that can be used for the above purpose.
- an object of the present invention is to achieve a necessary helical pitch length without significantly degrading the physical properties and optical properties of the liquid crystal composition by adding to the liquid crystal composition, having a high helical induction force. It is to provide an optically active compound capable of
- the present invention achieves the above object by providing a polymerizable optically active imide compound represented by the following general formula (I).
- the rings A 1 , A 2 , A 3 and A 4 each independently represent a benzene ring or a naphthalene ring, and a carbon atom in the benzene ring and naphthalene ring is substituted with a nitrogen atom.
- M 1 and M 2 each independently represents a hydrogen atom or a methyl group, and R 1 represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a carbon atom.
- X 1 is a direct bond, -L 1 -, - L 1 O -, - L 1 O-CO -, - L 1 CO-O- or -L 1 O-CO-O- and represents,
- X 2 and X 5 are each independently a direct bond, an ester bond, an ether bond, a branched And it may be an alkylene group which has good carbon atoms 1 be ⁇ 8 have an unsaturated bond, or represents a linking group comprising a combination thereof
- X 3 is a direct bond, -CO -, - L 2 -, - OL 2 -, - O-COL 2 -, - CO-OL 2 - , or -O-CO-OL 2 - represents,
- X 4 is a direct bond, -CO -, - L 1 - , - L 1 O -, - L 1 O -CO -, - L 1 CO-O- or -L 1 O-CO-O
- the present invention also provides a polymerizable composition containing the polymerizable optically active imide compound and, if necessary, a liquid crystal compound.
- the present invention also provides a polymer produced by photopolymerizing the above polymerizable composition and an optical film using the polymer.
- the polymerizable optically active imide compound of the present invention is a novel compound, and the reflection wavelength of a liquid crystal composition, particularly a cholesteric liquid crystal composition, can be shifted to a short wavelength side with a small amount. Moreover, the polymerizable optically active imide compound of the present invention can adjust the wavelength range of the selectively reflected light by changing the mesogenic skeleton. Furthermore, the optically active compound can be suitably used in an optical polarizer and an optical film as a chiral dopant.
- the polymerizable optically active imide compound of the present invention the polymerizable composition of the present invention containing the polymerizable optically active imide compound, and the polymer of the present invention prepared by photopolymerizing the polymerizable composition
- the polymerizable optically active imide compound of the present invention the polymerizable composition of the present invention containing the polymerizable optically active imide compound, and the polymer of the present invention prepared by photopolymerizing the polymerizable composition
- the alkyl group having 1 to 10 carbon atoms represented by R 1 includes methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, isoheptyl, t-heptyl, n-octyl, isooctyl, t-octyl, 2-ethylhexyl and the like.
- Examples of the aryl group having 6 to 20 carbon atoms include phenyl, naphthyl, Examples include 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, etc.
- arylalkyl group having 7 to 20 carbon atoms examples include benzyl, phenethyl, 2-phenylpropane -2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl
- the hydrogen atom of the substituent may be substituted with a halogen atom such as fluorine, chlorine, bromine or iodine, and the methylene group of the substituent is —O—, —COO— or —OCO—. It may be interrupted.
- the alkylene group having 1 to 8 carbon atoms represented by X 2 , X 5 , L 1 and L 2 is methylene, ethylene, propylene, trimethylene, tetramethylene, 1,3- Butanediyl, 2-methyl-1,3-propanediyl, 2-methyl-1,3-butanediyl, 2,4-pentanediyl, 1,4-pentanediyl, 3-methyl-1,4-butanediyl, 2-methyl-1 , 4-pentanediyl, pentamethylene, hexamethylene, heptamethylene, octamethylene and the like, which may be interrupted 1 to 3 times with an oxygen atom.
- a polymerizable optically active imide compound in which X 3 and X 4 are both —CO— is advantageous in terms of production and is preferable because of its high chemical and thermal stability.
- a polymerizable optically active imide compound in which rings A 2 and A 3 are both naphthalene rings in formula (I), or a polymerizable optically active imide compound in which rings A 1 , A 2 , A 3 and A 4 are all benzene rings Is more preferable because of excellent compatibility with the mother liquid crystal.
- a polymerizable optically active imide compound in which M 1 and M 2 are both hydrogen atoms is preferable because of high polymerization reactivity and solvent solubility.
- Ring A 1 and Ring A 4 and Ring A 2 and Ring A 3 are the same ring, and M 1 and M 2 , X 1 and X 6 , X 2 and X 5 and X 3 and X 6 are the same respectively.
- X 1 and X 6 are an alkylene group having 1 to 8 carbon atoms which may have a branch because it can be easily produced.
- the compound of the present invention is a compound having optical activity.
- Optical activity refers to a compound having optical activity and causing rotation when linearly polarized light passes through. That is, among the compounds of the present invention represented by the above general formula (I), a compound that exhibits dextrorotatory or levorotatory properties when the optical rotation is measured is the optically active compound of the present invention.
- polymerizable optically active imide compound of the present invention represented by the above general formula (I) include the following compounds.
- the present invention is not limited by the following compounds.
- the production method of the polymerizable optically active imide compound of the present invention is not particularly limited, and can be produced by applying a known reaction.
- a condensing agent is used. And can be obtained by performing a dehydration condensation reaction.
- ring A 11 represents a benzene ring or a naphthalene ring having a substituent corresponding to the above general formula (I), and R 1 is the same as the above general formula (I).
- the optical purity of the polymerizable optically active imide compound of the present invention obtained by the above production method depends on the optical purity of tartaric acid for obtaining a raw material tartarimide derivative. Since tartaric acid is easily available in both enantiomers, the polymerizable optically active imide compound of the present invention can be obtained with high optical purity.
- the polymerizable optically active imide compound of the present invention is blended in a liquid crystal material, particularly a liquid crystal material exhibiting a cholesteric phase, and has excellent optical anisotropy in heat resistance, solvent resistance, transparency, optical properties and liquid crystal alignment fixing ability.
- a liquid crystal alignment film particularly a liquid crystal material exhibiting a cholesteric phase
- it can be used for a liquid crystal alignment film, a liquid crystal alignment control agent, a coating material, a protective plate preparation material, and the like.
- the polymerizable composition of the present invention contains the polymerizable optically active imide compound of the present invention, and the one containing a liquid crystal compound is preferably used as a material for producing an optical anisotropic body.
- the liquid crystal compounds referred to here include conventionally known liquid crystal compounds, liquid crystal analogs, and mixtures thereof.
- the blending ratio of the polymerizable optically active imide compound of the present invention and the liquid crystal compound is not particularly limited, and is within a range where the curing of the polymerizable optically active imide compound of the present invention is not impaired.
- the polymerizable optically active imide compound of the present invention is preferably 1 to 50 parts by mass, particularly 1 to 30 parts by mass. . If the ratio of the polymerizable optically active imide compound of the present invention is less than 1 part by mass, the effect of the present invention may not be obtained. If it is greater than 50 parts by mass, phase separation may occur when curing the polymerizable composition. It may occur, or clouding may appear due to precipitation of the polymerizable optically active imide compound and non-uniform alignment of liquid crystal molecules.
- liquid crystal compound generally used liquid crystal compounds can be used, and specific examples of the liquid crystal compounds are not particularly limited.
- [Chemical 9] and [Chemical 10] The liquid crystal compound shown is mentioned.
- W 1 in [Chemical 9] or [Chemical 10] represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a branch, or 1 to 8 carbon atoms which may have a branch.
- a liquid crystal compound having a polymerizable functional group is preferably used as the liquid crystal compound.
- the polymerizable functional group includes (meth) acryloyloxy group, fluoroacrylic group, chloroacrylic group, trifluoromethylacrylic group, oxirane ring (epoxy), oxetane ring, styrene compound (styryl group), vinyl group, vinyl ether group. , Vinyl ketone group, maleimide group, phenylmaleimide group and the like are preferable.
- liquid crystal compound having a polymerizable functional group those generally used can be used, and specific examples thereof are not particularly limited, but are described in paragraph [0172] of JP-A-2005-15473. To [0314] and the compounds shown in the following [Chemical Formula 11] to [Chemical Formula 22].
- the polymerizable composition of the present invention can be dissolved in a solvent and made into a solution together with other monomers (compounds having an ethylenically unsaturated bond) and a radical polymerization initiator used as necessary.
- Examples of the other monomer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, secondary butyl (meth) acrylate, and tertiary butyl (meth) acrylate.
- the content of other monomers is the polymerizable optically active imide compound of the present invention and the above liquid crystal compound. Is preferably 50 parts by mass or less, particularly preferably 30 parts by mass or less, based on 100 parts by mass of the total.
- benzoin ethers such as benzoin butyl ether; benzyl ketals such as benzyldimethyl ketal; 1-hydroxy-1-benzoylcyclohexane, 2- ⁇ -hydroxyacetophenones such as hydroxy-2-benzoylpropane and 2-hydroxy-2- (4′-isopropyl) benzoylpropane; chloroacetophenones such as 4-butylbenzoyltrichloromethane and 4-phenoxybenzoyldichloromethane; 1-benzyl -1-dimethylamino-1- (4′-morpholinobenzoyl) propane, 2-morpholyl-2- (4′-methylmercapto) benzoylpropane, 9-n-butyl-3,6-bis (2′-morpholinoiso) Butyroyl ⁇ -aminoacetophenones such as carbazole and 2-methyl-1- [4-
- ⁇ -acyl oxime esters such as benzoyl peroxide, 2,2′-azobisisobutyronitrile, ethyl anthraquinone, 1, 7-bis (9′-acridinyl) heptane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, benzophenone, phenylbiphenyl ketone, 4-benzoyl-4′-methyldiphenyl sulfide, 2- (p- Butoxystyryl) -5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-dimethylbenzphenazine, benzophenone /
- R 71 , R 72 and R 73 each independently represent R, OR, COR, SR, CONRR ′ or CN
- R and R ′ each independently represent an alkyl group, an aryl group, an aryl Represents an alkyl group or a heterocyclic group, which may be substituted with a halogen atom and / or a heterocyclic group, and among these, the alkylene part of the alkyl group and arylalkyl group is an unsaturated bond, ether bond, thioether bond , May be interrupted by an ester bond, R and R ′ may be combined to form a ring
- R 74 represents a halogen atom or an alkyl group
- R 75 is a hydrogen atom
- a halogen atom, an alkyl group or a substituent represented by the following general formula (b) is represented, g is an integer of 0 to 4, and when g is 2 or more, a plurality of R 74 may be different groups.
- ring M represents a cycloalkane ring, an aromatic ring or a heterocyclic ring
- R 76 represents a halogen atom or an alkyl group
- Y 71 represents an oxygen atom, a sulfur atom or a selenium atom
- Z 71 represents the number of carbon atoms.
- h is an integer of 0 to 4, and when h is 2 or more, the plurality of X 73 may be different groups.
- R 51 and R 52 each independently represent R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN;
- R 11 , R 12 and R 13 are each independently Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, an alkyl group
- the methylene group of the alkylene part of the substituent represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is an unsaturated bond, ether bond, thioether bond, ester It may be interrupted 1 to 5 times by a bond, a thioester bond, an amide bond or a urethane bond, and the alkyl part of the substituent may have a branched side chain, may be a cyclic alkyl, The alkyl terminal may be an unsaturated bond, and R 12 and R 13 and R 22 and R 23 may be combined to form a ring, and R 53 and R 54 are each independently in, R 11, OR 11, R 11, COR 11, CONR 12 R 13, NR 12 COR 11, OCOR 11, COOR 11, SCOR 11, OCSR 11, COSR 11, CSOR 11, CN, a halogen atom or a hydroxyl group, a and b are each independently And 0 to 4.
- X 51 represents a direct bond or CO
- X 52 represents an oxygen atom, a sulfur atom, a selenium atom
- R 31 , R 32 , R 33 and R 34 each independently represent R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN
- R 53 represents an adjacent benzene ring via —X 2 —. May be bonded to one of the carbon atoms to form a ring structure, or R 53 and R 54 may be combined to form a ring, and R 31 , R 33 and R 34 are each Independently, together with one of the adjacent benzene rings It may form a. )
- a combination of the above radical polymerization initiator and a sensitizer can be preferably used.
- sensitizers include thioxanthone, phenothiazine, chlorothioxanthone, xanthone, anthracene, diphenylanthracene, and lupine.
- the addition amount thereof is 10 parts by mass with respect to 100 parts by mass of the total amount of the polymerizable optically active imide compound of the present invention and the liquid crystal compound, respectively.
- the amount is preferably not more than part by mass, more preferably not more than 5 parts by mass, and more preferably in the range of 0.1 to 3 parts by mass.
- solvent examples include benzene, toluene, xylene, mesitylene, n-butylbenzene, diethylbenzene, tetralin, methoxybenzene, 1,2-dimethoxybenzene, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclopentanone.
- the solvent may be a single compound or a mixture. Among these solvents, those having a boiling point of 60 to 250 ° C. are preferable, and those having a boiling point of 60 to 180 ° C. are particularly preferable. If the temperature is lower than 60 ° C., the solvent is volatilized in the coating process and the film thickness is likely to be uneven. If the temperature is higher than 250 ° C., the solvent remains even when the pressure is reduced in the desolvation step. In some cases, the orientation may be reduced.
- optically active compounds can be added to the polymerizable composition of the present invention for the purpose of adjusting the selective reflection wavelength, the compatibility with the liquid crystal, and the like.
- the addition amount thereof is within the range of 0.1 to 100 parts by mass with respect to 100 parts by mass of the total amount of the polymerizable optically active imide compound of the present invention and the liquid crystal compound.
- the range of 1 to 50 parts by mass is more preferable.
- Examples of such an optically active compound include compounds represented by the following [Chemical Formula 26].
- the polymerizable composition of the present invention may further contain a surfactant having an excluded volume effect distributed on the air interface side.
- a surfactant those which give effects such as easy application of the polymerizable composition to a support substrate and the like, and control of the orientation of the liquid crystal phase are preferable.
- Such surfactants include quaternary ammonium salts, alkylamine oxides, polyamine derivatives, polyoxyethylene-polyoxypropylene condensates, polyethylene glycol and esters thereof, sodium lauryl sulfate, ammonium lauryl sulfate, lauryl sulfate amines, alkyl-substituted aromatics.
- the preferred amount of surfactant used depends on the type of surfactant, the component ratio of the composition, etc., but with respect to 100 parts by mass of the total amount of the polymerizable optically active imide compound of the present invention and the liquid crystal compound, The range is preferably from 0.01 to 5 parts by mass, and more preferably from 0.05 to 1 part by mass.
- the polymerizable composition of the present invention may further contain additives as necessary.
- additives for preparing the characteristics of the polymerizable composition include storage stabilizers, antioxidants, ultraviolet absorbers, infrared absorbers, fine particles such as inorganic and organic substances, and functional compounds such as polymers. Is mentioned.
- the above storage stabilizer can impart the effect of improving the storage stability of the polymerizable composition.
- examples of the stabilizer that can be used include hydroquinone, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, 2-naphthylamines, and 2-hydroxynaphthalenes.
- antioxidant known compounds can be used without particular limitation, and hydroquinone, 2,6-di-t-butyl-p-cresol, 2,6-di-t-butylphenol, triphenyl phosphite , Trialkyl phosphites and the like can be used.
- the ultraviolet absorber a known compound can be used without any particular limitation.
- the one with a can be used.
- the fine particles can be used for adjusting optical (refractive index) anisotropy ( ⁇ n) and increasing the strength of the polymer.
- the material of the fine particles include inorganic substances, organic substances, metals, and the like.
- the fine particles preferably have a particle size of 0.001 to 0.1 ⁇ m, and more preferably have a particle size of 0.001 to 0.05 ⁇ m. Further, it is preferable that the particle size distribution is sharp.
- the finely divided product is preferably used in a range of 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the polymerizable optically active imide compound of the present invention and the liquid crystal compound.
- Examples of the inorganic substance include ceramics, fluorine phlogopite, fluorine tetrasilicon mica, teniolite, fluorine vermiculite, fluorine hectorite, hectorite, saponite, stevensite, montmorillonite, beidellite, kaolinite, frypontite, ZnO, TiO 2 and CeO 2.
- fine particles such as calcium carbonate needle crystals have optical anisotropy, and the optical anisotropy of the polymer can be adjusted by such fine particles.
- the organic substance include carbon nanotubes, fullerenes, dendrimers, polyvinyl alcohol, polymethacrylates, and polyimides.
- the above polymer can control the electrical characteristics and orientation of the polymer.
- a polymer compound soluble in the solvent can be preferably used.
- examples of such a polymer compound include polyamide, polyurethane, polyurea, polyepoxide, polyester, and polyester polyol.
- the polymer of the present invention for example, after dissolving the polymerizable composition in a solvent to form a solution, it is applied to a support substrate and desolvated in a state where liquid crystal molecules in the polymerizable composition are aligned, Subsequently, it can obtain by superposing
- an optically active monomer for obtaining the above polymer As an optically active monomer for obtaining the above polymer, it has a large helical induction force, exerts its effect even when added in a small amount, has excellent solubility in other liquid crystal compounds and organic solvents, and has excellent coating properties. It is desirable that polymerization is possible by irradiation with electromagnetic waves, no visible light absorption and no coloration.
- the polymer must be excellent in transparency, mechanical strength, heat resistance and chemical resistance.
- the polymer of the present invention when used as an optical compensation material such as an optical film, it is required to have a selective reflection wavelength, to have a uniform orientation, to exhibit a specific retardation change by an inclination angle, etc. Listed as a characteristic.
- the polymer using the polymerizable optically active imide compound of the present invention has uniform reflection and uniform reflection over the entire surface of the film, as will be described in more detail in the examples described later.
- the polymerizable optically active imide compound of the present invention has a large helical induction force, and can shift the selected wavelength of the liquid crystal composition, particularly the cholesteric liquid crystal composition, to a short wavelength side with a small amount.
- the polymerizable optically active imide compound of the present invention can adjust the wavelength range of the selectively reflected light by changing its mesogenic skeleton.
- the polymerizable optically active imide compound of the present invention is easily available in both enantiomers, a polymer that does not transmit light of a specific wavelength is obtained by preparing a polymer composed of both enantiomers. Can be used as a cut filter.
- the support substrate is not particularly limited, but preferred examples include glass plates, polyethylene terephthalate plates, polycarbonate plates, polyimide plates, polyamide plates, polymethyl methacrylate plates, polystyrene plates, polyvinyl chloride plates, polytetrafluoroethylene.
- a board, a cellulose board, a silicon board, a reflecting plate, a cycloolefin polymer, and a calcite board are mentioned.
- a substrate obtained by applying a polyimide-based alignment film or a polyvinyl alcohol-based alignment film as described later on such a support substrate can be particularly preferably used.
- a known method can be used, such as a curtain coating method, an extrusion coating method, a roll coating method, a spin coating method, Examples include dip coating, bar coating, spray coating, slide coating, print coating, and cast film formation.
- the film thickness of the polymer of the present invention is appropriately selected depending on the application and the like, but is preferably in the range of 0.001 to 30 ⁇ m, more preferably 0.001 to 10 ⁇ m, and particularly preferably 0.005 to 8 ⁇ m. Selected from.
- Examples of a method for aligning the liquid crystal molecules in the polymerizable composition of the present invention include a method in which an alignment treatment is performed on a support substrate in advance.
- As a preferred method for performing the alignment treatment there is a method in which a liquid crystal alignment layer composed of various polyimide alignment films or polyvinyl alcohol alignment films is provided on a support substrate and a treatment such as rubbing is performed.
- the method of applying a magnetic field, an electric field, etc. to the polymeric composition on a support substrate is also mentioned.
- a known method using light, electromagnetic waves or heat can be applied.
- the polymerization reaction by light or electromagnetic wave include radical polymerization, anionic polymerization, cationic polymerization, coordination polymerization, and living polymerization. This is because according to these polymerization reactions, it is easy to carry out the polymerization under the condition that the polymerizable composition exhibits a liquid crystal phase. It is also preferable to crosslink while applying a magnetic field or an electric field.
- the liquid crystal (co) polymer formed on the support substrate may be used as it is, but may be used after peeling from the support substrate or transferring to another support substrate, if necessary.
- Preferred types of the light are ultraviolet rays, visible rays, infrared rays and the like. You may use electromagnetic waves, such as an electron beam and an X-ray. Usually, ultraviolet rays or visible rays are preferable. A preferable wavelength range is 150 to 500 nm. A more preferable range is 250 to 450 nm, and a most preferable range is 300 to 400 nm.
- a light source a low-pressure mercury lamp (sterilization lamp, fluorescent chemical lamp, black light), a high-pressure discharge lamp (high-pressure mercury lamp, metal halide lamp), or a short arc discharge lamp (ultra-high pressure mercury lamp, xenon lamp, mercury xenon lamp), etc.
- an ultrahigh pressure mercury lamp Light from the light source may be irradiated to the polymerizable composition as it is, or a specific wavelength (or a specific wavelength region) selected by a filter may be irradiated to the polymerizable composition.
- Preferred irradiation energy density is 2 ⁇ 5000mJ / cm 2, more preferred range is 10 ⁇ 3000mJ / cm 2, particularly preferred range is 100 ⁇ 2000mJ / cm 2.
- Preferred illuminance is 0.1 ⁇ 5000mW / cm 2, more preferably illuminance is 1 ⁇ 2000mW / cm 2.
- preferable irradiation temperature is 100 degrees C or less. Polymerization due to heat can occur at a temperature of 100 ° C. or higher, and thus good alignment may not be obtained.
- the polymer of the present invention includes, for example, a retardation plate (1/2 wavelength plate, 1/4 wavelength plate, negative C plate, etc.), polarizing element, dichroic polarizing plate, antireflection film, selective reflection film, viewing angle. It can be used for optical films such as compensation films and brightness enhancement films.
- alignment control materials such as liquid crystal alignment films, optical lenses such as liquid crystal lenses and microlenses, polymer dispersed liquid crystal (PDLC) displays, electronic paper, color filters, wavelength cut filters, holographic elements, nonlinear optical elements, optical memory It can also be used for information recording materials such as elements and anti-counterfeiting agents, and for other uses such as adhesives, cosmetics, and ornaments.
- Examples 1-1 to 1-5 below are compound Nos. Which are polymerizable optically active imide compounds of the present invention. 1-No. Examples 5 to 5 are shown. Examples 2-1 to 2-5 are examples of producing the polymerizable composition and polymer of the present invention. Evaluation examples 1 to 3 are selective reflection measurement, orientation confirmation, and The evaluation example of the polymer of this invention by the measurement of retardation is shown.
- a colorless oil was obtained in the same manner as in Example 1-2 except that (+)-N-propyl-L-tartarimide was replaced with 0.73 g (5.00 mmol) of (+)-N-methyl-L-tartarimide. 3.32 g (yield 83.6%) of the product was obtained.
- the various colorless oils thus obtained were subjected to various analyses. 3 was identified.
- a colorless oil was obtained in the same manner as in Example 1-2 except that (+)-N-propyl-L-tartarimide was replaced with 0.73 g (5.00 mmol) of (-)-N-methyl-D-tartarimide. 3.63 g (yield 91.4%) of the product was obtained.
- the various colorless oils thus obtained were subjected to various analyses. 4 was identified.
- a polymerizable composition was prepared as shown in the following (i) and (ii).
- 0.5 g of each prepared polymerizable composition was added to 1.0 g of 2-butanone (containing 375 ppm of KH-40 (manufactured by AGC Seimi Chemical Co., Ltd.) as a surfactant) and thoroughly heated with hot water.
- the polymerizable optically active imide compound of the present invention can change the selective reflection wavelength by changing the blending amount. From this, it is clear that the polymerizable optically active imide compound of the present invention is useful in various filters and C plate applications.
- ⁇ Method for evaluating orientation uniformity> The homogeneity of the obtained polymer was evaluated using a polarizing microscope (manufactured by Nikon Corporation; OPTIPHOT2-POL). That is, the alignment state of the polymer was visually observed by rotating the stage on which the polymer sample was placed under crossed Nicols, and the uniformity of the alignment was evaluated. Note that the evaluation criteria were ⁇ if the selective reflection was uniform and no alignment defect was confirmed, and x if crystallization or alignment unevenness was confirmed.
- the polymer produced using the polymerizable optically active compound other than the present invention has white turbidity due to the precipitation of the polymerizable optically active compound and the non-uniform alignment of the liquid crystal molecules, and the selective reflection is observed. I was not able to admit.
- the polymer produced using the polymerizable optically active imide compound of the present invention was uniform in orientation over the entire surface of the film, and selective reflection could be confirmed. From this, it is clear that the polymerizable optically active imide compound of the present invention is useful.
- Example 3 In Example 2 above, among the polymers obtained from the blending of (ii), Compound No. No. 3 and a polymer obtained by blending the compound No. The polymer obtained by blending 4 was pasted together, and the pasted polymer was subjected to ultraviolet-visible absorption spectrum measurement using an ultraviolet-visible near-infrared spectrophotometer (manufactured by JASCO Corporation; V-570). Went. As a result, a spectrum having a minimum value of 15.6% transmittance at a wavelength of 746 nm was measured. From this, it was confirmed that the polymer of the present invention can be used for a use as a cut filter that does not transmit a specific wavelength by using a polymer of both enantiomers in an overlapping manner.
- an ultraviolet-visible near-infrared spectrophotometer manufactured by JASCO Corporation; V-570.
- ⁇ Retardation evaluation method> Using a polarizing microscope (manufactured by Nikon Corporation: OPTIPHOT2-POL), retardation measurement was performed by the Senarmon method with monochromatic light having a wavelength of 546 nm. In this case, the retardation at each inclination angle was measured by setting the substrate on a pedestal that can change the inclination angle and measuring the angle.
Abstract
Description
上記一般式(I)中、R1で表される炭素原子数1~10のアルキル基としては、メチル、エチル、プロピル、イソプロピル、ブチル、s-ブチル、t-ブチル、イソブチル、アミル、イソアミル、t-アミル、ヘキシル、シクロヘキシル、ヘプチル、イソヘプチル、t-ヘプチル、n-オクチル、イソオクチル、t-オクチル、2-エチルヘキシル等が挙げられ、炭素原子数6~20のアリール基としては、フェニル、ナフチル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-ビニルフェニル、3-イソプロピルフェニル等が挙げられ、炭素原子数7~20のアリールアルキル基としては、ベンジル、フェネチル、2-フェニルプロパン-2-イル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等が挙げられ、上記置換基の水素原子はフッ素、塩素、臭素、ヨウ素等のハロゲン原子で置換されていてもよく、上記置換基のメチレン基は、-O-、-COO-又は-OCO-で中断されていてもよい。
本発明の重合性組成物は、本発明の重合性光学活性イミド化合物を含有するもので、さらに液晶化合物を含有するものは、光学異方体作製用材料として好ましく用いられる。尚、ここでいう液晶化合物には、従来既知の液晶化合物及び液晶類似化合物並びにそれらの混合物が含まれる。
上記有機物としては、カーボンナノチューブ、フラーレン、デンドリマー、ポリビニルアルコール、ポリメタクリレート、ポリイミド等が挙げられる。
本発明の重合体は、例えば、上記重合性組成物を溶剤に溶解して溶液とした後、支持基板に塗布して、重合性組成物中の液晶分子を配向させた状態で脱溶媒し、次いでエネルギー線を照射して重合することにより得ることができる。
下記の手順((1)重合性組成物溶液の調製、(2)基板への塗布・硬化)に従って重合体を作製した。
先ず、以下の(i)及び(ii)の通り、重合性組成物をそれぞれ調製した。
(i)下記液晶化合物No.1に対して、上記化合物No.1を下記〔表3〕に記載の割合でそれぞれ配合した。
(ii)下記液晶化合物No.1に対して、上記化合物No.1~No.5及び下記比較化合物No.1をそれぞれ10%配合した。
次に、調製した各重合性組成物0.5gを、2-ブタノン1.0g(界面活性剤としてKH-40(AGCセイミケミカル(株)製)を375ppm含有)に添加して温湯で完全に溶解した後、ラジカル重合開始剤としてN-1919((株)ADEKA製)0.015gを加えて完全に溶解した。次いで、0.45μmフィルターでろ過処理を実施することによって重合性組成物溶液をそれぞれ調製した。
上記(1)で調製した各重合性組成物溶液を、ポリイミドを塗布しラビングを施したガラス基板上にスピンコーター(2000rpm、10秒)で塗布した。塗工後、ホットプレートを用いて100℃で3分間乾燥した後に、室温下で1分間冷却し、次いで高圧水銀灯を使用し、300mJ/cm2に相当する光を照射し、塗工膜を硬化させ、実施例2-1~2-5及び比較例1の重合体をそれぞれ得た。
上記実施例2で得られた重合体のうち、(i)の配合のものについて、以下の方法により、選択反射を評価した。これらの評価結果を下記〔表3〕に示す。
5°正反射付属装置を取り付けた分光光度計((株)日立ハイテクノロジーズ製;U-3010形)を使用して、25℃、波長800~400nmの範囲で反射率測定を実施し、選択反射中心波長(λ)を測定し、選択反射を評価した。
上記実施例2及び比較例1で得られた重合体のうち、(ii)の配合のものについて、上述の方法により選択反射を評価するとともに、以下の方法により、配向の均質性を評価した。これらの評価結果を下記〔表4〕に示す。
得られた重合体の均質性を偏光顕微鏡((株)ニコン製;OPTIPHOT2-POL)を用いて評価した。即ち、クロスニコル下で重合体試料を設置したステージを回転させることによって、重合体の配向状態を目視で観察し、配向の均質性を評価した。尚、評価の基準は、選択反射が一様で、配向欠陥が確認されなければ○、結晶化や配向ムラが確認された場合は×とした。
上記実施例2において、(ii)の配合から得られた重合体のうち、化合物No.3を配合して得られた重合体と、化合物No.4を配合して得られた重合体とを張り合わせ、この貼り合わせた重合体について、紫外可視近赤外分光光度計(日本分光(株)製;V-570)を用いて紫外可視吸収スペクトル測定を行った。その結果、746nmの波長に透過率15.6%の極小値を持つスペクトルが測定された。このことより、本発明の重合体のなかでも、両鏡像体の重合体を重ねて使用することにより特定の波長を透過させないカットフィルターとしての用途に用いることができることが確認された。
上記実施例2において、(i)の配合から得られた重合体のうち、化合物No.1を15質量%配合して得られた重合体、さらに別途化合物No.1を17質量%配合して得られた重合体について、以下の方法により、リターデーションを評価した。これらの評価結果を下記〔表5〕に示す。
偏光顕微鏡((株)ニコン製:OPTIPHOT2-POL)を用いて、波長546nmの単色光でセナルモン法により、リターデーション測定を行った。この際、傾斜角度を変えられる台座に基板を設置し、角度を変えて測定することで、各傾斜角度におけるリターデーションを測定した。
Claims (16)
- 下記一般式(I)で表される重合性光学活性イミド化合物。
- 上記一般式(I)中、X3及びX4が、共に-CO-である請求項1記載の重合性光学活性イミド化合物。
- 上記一般式(I)中、環A2及びA3が、共にナフタレン環である請求項1又は2記載の重合性光学活性イミド化合物。
- 上記一般式(I)中、環A1、A2、A3及びA4が、全てベンゼン環である請求項1又は2記載の重合性光学活性イミド化合物。
- 上記一般式(I)中、M1及びM2が、共に水素原子である請求項1~4の何れかに記載の重合性光学活性イミド化合物。
- 上記一般式(I)中、環A1と環A4及び環A2と環A3が、それぞれ同一の環であり、M1とM2、X1とX6、X2とX5及びX3とX6が、それぞれ同一の基であり、nとmが同一の数である請求項1~5の何れかに記載の重合性光学活性イミド化合物。
- 請求項1~6の何れかに記載の重合性光学活性イミド化合物を含有する重合性組成物。
- さらに液晶化合物を含有する請求項7記載の重合性組成物。
- 上記重合性光学活性イミド化合物の含有量と上記液晶化合物の含有量との合計を100質量部としたとき、該重合性光学活性イミド化合物の含有量が1~50質量部である請求項8記載の重合性組成物。
- 上記液晶化合物が、重合性官能基を有する化合物である請求項8又は9記載の重合性組成物。
- コレステリック相を示す請求項7~10の何れかに記載の重合性組成物。
- 請求項7~11の何れかに記載の重合性組成物を光重合させることにより作製された重合体。
- 光学異方性を有する請求項12記載の重合体。
- 請求項12又は13記載の重合体を使用してなる光学フィルム。
- 請求項14記載の光学フィルムを用いた液晶ディスプレイ用光位相差補償材料。
- 請求項14記載の光学フィルムを用いたカットフィルター。
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Also Published As
Publication number | Publication date |
---|---|
TWI455926B (zh) | 2014-10-11 |
EP2325168B1 (en) | 2014-03-19 |
US8512597B2 (en) | 2013-08-20 |
CN102089280A (zh) | 2011-06-08 |
JP5284735B2 (ja) | 2013-09-11 |
US20110108765A1 (en) | 2011-05-12 |
CN102089280B (zh) | 2014-04-09 |
JP2010070482A (ja) | 2010-04-02 |
KR20110056475A (ko) | 2011-05-30 |
TW201012799A (en) | 2010-04-01 |
EP2325168A4 (en) | 2013-05-29 |
KR101638789B1 (ko) | 2016-07-12 |
EP2325168A1 (en) | 2011-05-25 |
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