WO2015046964A1 - 광반응성 공중합체 및 이를 포함하는 배향막 - Google Patents
광반응성 공중합체 및 이를 포함하는 배향막 Download PDFInfo
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- WO2015046964A1 WO2015046964A1 PCT/KR2014/009045 KR2014009045W WO2015046964A1 WO 2015046964 A1 WO2015046964 A1 WO 2015046964A1 KR 2014009045 W KR2014009045 W KR 2014009045W WO 2015046964 A1 WO2015046964 A1 WO 2015046964A1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L45/02—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers of coumarone-indene polymers
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J5/18—Manufacture of films or sheets
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J145/00—Adhesives based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Adhesives based on derivatives of such polymers
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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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
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- 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
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- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
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Definitions
- the present invention relates to an optical semicoagulant copolymer and an alignment film comprising the same, and more particularly, an optical plate having excellent liquid crystal alignment property and an alignment speed, and having excellent solubility while having a property of easily changing the alignment direction according to the polarization direction. It relates to a male copolymer and an alignment film including the same.
- the thin film transistor liquid crystal display (TFT-LCD) driven by the thin film transistor independently drives individual pixels, so that the response speed of the liquid crystal is very high and a high quality moving image can be realized.
- the liquid crystal In order to use the liquid crystal as an optical switch in the TFT-LCD, the liquid crystal must be initially oriented in a predetermined direction on a layer on which the innermost thin film transistor of the display cell is formed. A liquid crystal alignment layer is used for this purpose.
- the photosensitive group bonded to a constant photoreactive polymer by linearly polarized UV causes photoreaction, and in this process, the main chain of the polymer is aligned in a certain direction, and thus the liquid crystal is aligned. Is formed.
- photo-alignment examples include M. Schadt et al. (Jpn. J. Appl. Phys, Vol 31., 1992, 2155), Dae S. Kang et al. (US Pat. No. 5,464,669), Yuriy Reznikov (Jpn. J. Appl. Phys. Vol. 34, 1995, L1000).
- the photoalignment polymers used in these patents and articles are mainly poly cinnamate-based poll a "reamer such as cinnamate)) or PVMC (poly (vinyl methoxycinnamate)) .
- the double bond of cinnamate reacts with [2 + 2] cycloaddition to form cyclobutane by irradiated UV, resulting in anisotropy.
- the alignment of the liquid crystal molecules is induced by arranging the liquid crystal molecules in one direction.
- Japanese Patent Laid-Open No. Hei 11-181127 discloses a polymer having a side chain including photosensitive groups such as cinnamic acid groups in main chains such as acrylate and methacrylate, and an alignment film comprising #.
- Korean Patent Laid-Open Publication No. 2002- 0006819 discloses the use of an alignment film made of a polymethacrylic polymer.
- the above-described photoreflex copolymers for alignment films have disadvantages such as poor thermal stability of the polymer main chain, thereby lowering the stability of the alignment films, insufficient photoreaction properties, liquid crystal alignment properties, or orientation speeds.
- the conventional photo-reflective copolymers have a problem that the solubility in organic solvents is not so high, the processability of forming an alignment layer by coating and drying a composition including the same is poor.
- the present invention is to provide a photoreactive copolymer that is easy to control the photoreactivity to a variety of light, and can be used in the alignment film and the like to exhibit improved interaction with the liquid crystal molecules and excellent photoreactivity.
- the present invention is to provide a method for producing the photo-reflective copolymer.
- the present invention is to provide an alignment film containing the light semi-coagulant copolymer.
- the present invention is a cyclic olefin monomer represented by the formula (1); And a copolymer of a cyclic olefin monomer represented by Formula 2 below.
- q is an integer of 0 to 4,
- At least one of Rl, R2, R3, and R4 is represented by the formula la Radicals,
- Ri to R4 except for being a radical of formula la are the same as or different from each other, and each independently hydrogen; halogen; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms; Substituted or unsubstituted aryl having 6 to 40 carbon atoms; Substituted or unsubstituted arylalkyl having 5 to 12 carbon atoms; And a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron;
- R1 to R4 are hydrogen; halogen; Or when it is not a polar functional group, one or more combinations of R1 and R2 or R3 and R4 are connected to each other to form an alkylidene group having 1 to 10 carbon atoms, or R1 or R2 is connected to any one of R3 and R4 to 4 carbon atoms To form a saturated or unsaturated aliphatic ring of 12 to 12, or an aromatic ring of 6 to 24 carbon atoms,
- A is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted Arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted carbon atoms having 2 to 2 carbon atoms and alkynylene,
- B is a simple bond, oxygen, sulfur, -NH- or 1,4-phenylene :
- R9 is a simple bond, substituted or unsubstituted carbon number 1
- C1 is arylene having 6 to 40 carbon atoms which is unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano and nitro; Arylalkylene having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more functional groups selected from the group consisting of halogen, cyano, and nitro; Or heteroarylene having 4 to 40 carbon atoms including group 14, 15 or 16 hetero elements,
- C2 and C3 are each independently the same or different from each other, arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more functional groups selected from the group consisting of halogen, cyano, and nitro; Or heteroarylene with 4 to 40 carbon atoms including group 14, 15 or 16 hetero elements; Or a cycloalkylene having 5 to 10 carbon atoms, or a heterocycloalkylene having 4 to 40 carbon atoms including a group 14, 15 or 16 hetero atom,
- D is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted Arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- R10 is hydrogen; halogen; Cyano; Nitro; -NCS; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy having 6 to 30 carbon atoms; And it is selected from the group consisting of substituted or unsubstituted aryl having 6 to 40 carbon atoms,
- At least one of R1 ', R2', R3 ', and R4' is a radical selected from the group consisting of Formulas 2a and 2b,
- R1 'to R4' are the same as or different from each other, and each independently hydrogen; halogen; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms; Substituted or unsubstituted aryl having 6 to 40 carbon atoms; And a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron,
- R1 'to R4' are hydrogen; halogen; Or when it is not a polar functional group, one or more combinations of R1 'and R2' or R3 'and R4' are connected to each other to form an alkylidene group having 1 to 10 carbon atoms, or R1 'or R2' is R3 'and R4' Connected to any one of to form a saturated or unsaturated aliphatic ring having 4 to 12 carbon atoms, or an aromatic ring having 6 to 24 carbon atoms,
- a ' is a simple bond, oxygen, sulfur, or -NH-
- B ' is a simple bond, substituted or unsubstituted C1-20 alkylene, carbonyl, carboxy, ester, substituted or unsubstituted C6-40 arylene and substituted or unsubstituted C6-40 hetero Selected from the group consisting of arylene,
- X is oxygen or sulfur
- R9 ' is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene having 2 to 20 carbon atoms, substituted or unsubstituted the carbon number of 3 to 12 cycloalkyl is selected from alkylene, substituted or unsubstituted arylene group having 6 to 40 carbon atoms, and the group consisting of aryl alkylene of the substituted or unsubstituted C7-C15 '
- At least one of RIO ', R11', R12 ', R13', and R14 ' is halogen or alkyl having 1 to 20 carbon atoms substituted with halogen, and others are the same or different from each other, and are each independently substituted or unsubstituted carbon number.
- the present invention is a repeating unit of the formula 3a by addition polymerization of the monomer represented by the formula (1) and the monomer represented by the formula (2) in the presence of a catalyst composition comprising a procatalyst and a cocatalyst comprising a Group 10 transition metal It provides a method for producing a photo-reflective copolymer of claim 3 comprising the step of forming a.
- the present invention provides an alignment film comprising the photo-reflective copolymer.
- the present invention provides a liquid crystal retardation film including the alignment film and the liquid crystal layer on the alignment film.
- the present invention provides a display device including the alignment layer.
- a bulky substituent including aryl, heteroaryl, cycloalkyl, or heterocycloalkyl may be bonded at the end of the photoreactor. Under the influence of these bulky substituents, the photoreactive copolymer has superior liquid crystal alignment and orientation rate than conventional photoreactive copolymers.
- the photoreactive copolymer can move the light reaction group relatively freely so that the change in the orientation direction according to the polarization direction is quite free.
- the light semicoherent copolymer and the alignment film including the same are It can be preferably applied to a patterned retarder, a patterned cell alignment layer, etc. applied for the implementation.
- the photo-reflective copolymer may exhibit excellent solubility in organic solvents due to the presence of substituents containing the aryl, heteroaryl, cycloalkyl, or heterocycloalkyl.
- the process of forming a good alignment film using a composition comprising the photo-reflective copolymer can be made easier.
- a male copolymer may be preferably applied to the optical alignment polymer in the alignment film formed easily from a number of coating compositions and which are applicable to various liquid crystal display devices, the alignment film comprising the same can exhibit excellent characteristics.
- FIG 1 schematically shows an example of an alignment film structure according to an embodiment of the present invention.
- each layer or element when each layer or element is referred to as being formed “on” or “on” of each layer or element, it means that each layer or element is formed directly on each layer or element, or It is meant that a layer or element can be additionally formed between each layer, on the object, the substrate.
- alkyl means a linear or branched saturated monovalent hydrocarbon moiety of 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms.
- the alkyl group may encompass not only unsubstituted but also further substituted by a certain substituent described below.
- alkyl groups include methyl, ethyl, propyl, 2-propyl, n-butyl, iso-butyl, tert-butyl, pentyl, nucleus, dodecyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, Dichloromethyl, trichloromethyl, iodomethyl, bromomethyl and the like.
- Alkenyl means a linear or branched monovalent hydrocarbon moiety of 2 to 20, preferably 2 to 10, more preferably 2 to 6 carbon atoms comprising at least one carbon-carbon double bond. . Alkenyl groups may be bonded through a carbon atom comprising a carbon-carbon back bond or through a saturated carbon atom. Alkenyl groups may be broadly referred to as unsubstituted as well as those further substituted by the following substituents. Examples of the alkenyl group include ethenyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, pentenyl, 5-nucenenyl, dodecenyl, and the like.
- Cycloalkyl means a saturated or unsaturated non-aromatic monovalent monocyclic, bicyclic, or tricyclic hydrocarbon moiety of 3 to 12 ring carbons, and also encompasses those further substituted with the following substituents. can do. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclonuxyl, cyclonuxenyl, cycloheptyl, cyclooctyl, decahydronaphthalenyl, adamantyl, norbornyl (ie, bicyclo [2,2, 1] hept-5-enyl).
- Aryl means from 6 to 40, preferably from 6 to 12 ring atoms
- a branch means a monovalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety, and may be referred to collectively further substituted by a certain substituent described below.
- Examples of the aryl group include phenyl, naphthalenyl, fluorenyl and the like.
- Alkoxyaryl means that at least one hydrogen atom of the aryl group as defined above is substituted with an alkoxy group.
- alkoxyaryl group examples include methoxyphenyl, ethoxyphenyl, propoxyphenyl, .butoxyphenyl, phenoxyphenyl, nucleooxyphenyl, hepoxy, oxoxy, nanoxy, methoxybiphenyl, methoxynaphthalenyl
- methoxy fluorenyl black include methoxy anthracenyl and the like.
- Arylalkyl means that at least one hydrogen atom of the alkyl group defined above is substituted with an aryl group, and may be referred to collectively further substituted by a specific substituent described below. For example, benzyl, benzhydryl, trityl, etc. are mentioned.
- Alkynyl means a linear or branched monovalent hydrocarbon moiety of from 2 to 20 carbon atoms, preferably from 2 to 10, more preferably from 2 to 6, containing at least one carbon-carbon triple bond. do. Alkynyl groups can be bonded through a carbon atom comprising a carbon-carbon tritiated bond or through a saturated carbon atom. Alkynyl groups may also be referred to collectively further substituted by certain substituents described below. For example, ethynyl, propynyl, etc. are mentioned.
- Alkylene means a linear or branched saturated divalent hydrocarbon moiety of 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms.
- the alkylene group can also be referred to collectively further substituted by certain substituents described below.
- methylene, ethylene, propylene, butylene, nuylene and the like can be given.
- Alkenylene means a linear or branched divalent hydrocarbon moiety of 2 to 20, preferably 2 to 10, more preferably 2 to 6 carbon atoms comprising at least one carbon-carbon double bond. do. Alkenylene groups may be bonded through a carbon atom comprising a carbon-carbon back bond and / or through a saturated carbon atom. Alkenylene groups are further substituted by certain substituents described below. It may also refer generically.
- Cycloalkylene means a saturated or unsaturated non-aromatic divalent monocyclic, bicyclic or tricyclic hydrocarbon moiety of 3 to 12 ring carbons, including those further substituted by certain substituents described below. May be referred to. For example, cyclopropylene, cyclobutylene, etc. can be mentioned.
- Arylene means a divalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having from 6 to 20, preferably from 6 to 12 ring atoms, further substituted by certain substituents described below It may be referred to inclusively.
- the aromatic moiety contains only carbon atoms. Phenylene etc. are mentioned as an example of an arylene group.
- Arylalkylene means a divalent moiety where at least one hydrogen atom of the alkyl group defined above is substituted with an aryl group, and may also be referred to as being further substituted by a specific substituent described below. For example, benzylene etc. can be mentioned.
- Alkynylene is a 2 to 3 containing one or more carbon-carbon triple bonds
- Alkynylene groups may be bonded through a carbon atom comprising a carbon-carbon tritiated bond or through a saturated carbon atom. Alkynylene groups can also be referred to collectively further substituted by certain substituents described below. For example, ethynylene, propynylene, etc. are mentioned.
- Substituent described above "substituted or unsubstituted” is meant to encompass not only each of these substituents themselves, but also those further substituted by a certain substituent.
- substituents which may be further substituted with each substituent include halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, Arylalkyl, haloarylalkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, chaloxy, or "oxygen, nitrogen, phosphorus, sulfur, silicon or boron, described below.
- the cyclic olefin resin represented by the following formula (1) As a photoreactive copolymer, an alignment layer, a retardation film, and a display device according to an embodiment of the present invention will be described in detail.
- the cyclic olefin resin represented by the following formula (1) As a copolymer of a cyclic olefin monomer represented by the following Chemical Formula 2 is provided.
- q is an integer from 0 to 4,
- At least one of Rl, R2, R3, and R4 is a radical represented by the formula la,
- R 1 to R 4 are the same as or different from each other, and each independently hydrogen; halogen; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms; Substituted- or unsubstituted aryl of 6 to 40 carbon atoms; Substituted or unsubstituted arylalkyl having 5 to 12 carbon atoms; And a polar functional group comprising at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron;
- R1 to R4 are hydrogen; halogen; Or when it is not a polar functional group, one or more combinations of R1 and R2 or R3 and R4 are connected to each other to form an alkylidene group having 1 to 10 carbon atoms, or R1 or R2 is any of R3 and R4 Connected to one to form a saturated or unsaturated aliphatic ring having 4 to 12 carbon atoms and an aromatic ring having 6 to 24 carbon atoms,
- A is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted Arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 2 carbon atoms,
- B is a simple bond, oxygen, sulfur, -NH- or 1,4-phenylene
- R9 is a single bond, substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C2-C20 alkenylene, substituted or unsubstituted C3-C12 cycloalkylene, substituted or unsubstituted Substituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- C1 is arylene having 6 to 40 carbon atoms which is unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano and nitro; Arylalkylene having 7 to 15 carbon atoms which is unsubstituted or substituted with one or more functional groups selected from the group consisting of halogen, cyano, and nitro; Or heteroarylene having 4 to 40 carbon atoms including group 14, 15 or 16 hetero elements,
- C2 and C3 are each independently the same or different from each other, arylene having 6 to 40 carbon atoms unsubstituted or substituted with one or more functional groups selected from the group consisting of halogen, cyano, and nitro; Or heteroarylene having 4 to 40 carbon atoms including group 14, 15 or 16 hetero elements; Or a cycloalkylene having 5 to 10 carbon atoms or a heterocycloalkylene having 4 to 40 carbon atoms including a group 14, 15 or 16 hetero atom,
- D is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted Or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted aryl having 7 to 15 carbon atoms Alkylene and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- R10 is hydrogen; halogen; Cyano; Nitro; -NCS; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy having 6 to 30 carbon atoms; And substituted or unsubstituted aryl having 6 to 40 carbon atoms,
- q ' is an integer from 0 to 4,
- At least one of R1 ', R2', R3 ', and R4' is a radical selected from the group consisting of Formulas 2a and 2b,
- R1 'to R4' are the same as or different from each other, and each independently hydrogen; halogen; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms; Substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms; Substituted or unsubstituted aryl having 6 to 40 carbon atoms; And a polar functional group comprising at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron,
- R1 'to R4' are hydrogen; halogen; Or when it is not a polar functional group, one or more combinations of R1 'and R2' or R3 'and R4' are linked to each other to have 1 to Or an alkylidene group of 10, or R1 'or R2' may be linked to either of R3 'and R4' to form a saturated or unsaturated aliphatic ring having 4 to 12 carbon atoms or an aromatic ring having 6 to 24 carbon atoms.
- R1 'to R4' are hydrogen; halogen; Or when it is not a polar functional group, one or more combinations of R1 'and R2' or R3 'and R4' are linked to each other to have 1 to Or an alkylidene group of 10, or R1 'or R2' may be linked to either of R3 'and R4' to form a saturated or unsaturated aliphatic ring having 4 to 12 carbon atoms or an aromatic ring having 6 to 24 carbon
- a ' is a simple bond, oxygen, sulfur, or -NH-
- B ' is a simple bond, a substituted or unsubstituted C 1 -C 20 alkylene, carbonyl, carboxy, ester, substituted or unsubstituted C 6 arylene to 40 ring: a and a substituted or unsubstituted C6-C40 Selected from the group consisting of heteroarylene,
- X is oxygen or sulfur
- R9 ' is a simple bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted alkynylene having 2 to 20 carbon atoms, substituted or unsubstituted Cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, and substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms,
- At least one of RIO ', Rl l', R12 ', R13' and R14 ' is halogen, or Alkyl having 1 to 20 carbon atoms substituted with halogen, the remainder being the same or different from each other, each independently substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted Substituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 40 carbon atoms, heteroaryl having 6 to 40 carbon atoms including group 14, 15 and 16 heteroatoms, and substituted or unsubstituted It is selected from the group consisting of alkoxyaryl having 6 to 40 carbon atoms.
- R1 'of Formula 2 may be a radical represented by Formula 2a, and at least one of R10' to R14 'of Formula 2a may be halogen.
- the monomer which may be represented by Formula 1 may have a chemical structure in which a photoreactor such as a cinnamic structure or a chalcone structure is introduced into a cyclic olefinic structure (for example, la). . Due to the chemical structure into which the photoreactor is introduced, the cyclic olefin compound represented by Chemical Formula 1 may be used as a photo reaction compound by itself.
- the monomer of Chemical Formula 1 may have a chemical structure in which a cyclic substituent (C2) is further bonded to a photoreactor such as a cinnamate structure or a chalcone structure through a specific functional group A, and also a cyclic type through a specific functional group D
- the substituent (C3) may have a chemical structure further bonded.
- C1 may be unsubstituted or substituted with arylene having 6 to 40 carbon atoms (eg, substituted with one or more functional groups selected from the group consisting of halogen, cyano, and nitro).
- C2 bonded to C1 through a specific functional group A may be unsubstituted or substituted with arylene having 6 to 40 carbon atoms (eg, substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro (eg, Substituted or unsubstituted phenylene or 1,4- or 2,6-naphthylene and the like); Or heteroarylene having 4 to 40 carbon atoms, including group 14, 15, or 16 hetero elements (eg, 2,5-thiophenediyl, 2,5-furanylene ( 2 , 5- fiiranylene, etc.); Or cycloalkylene having 5 to 10 carbon atoms (eg, cyclohexyl, etc.); Or heterocycloalkylene having 4 to 40 carbon atoms (eg, 1, 3-dioxyl) containing a Group 14, Group 15, or Group 16 hetero element.
- arylene having 6 to 40 carbon atoms eg, substituted with at least one
- C3 bonded to C2 through a specific functional group D may be unsubstituted or substituted with arylene having 6 to 40 carbon atoms (eg, substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro (eg, Substituted or unsubstituted phenylene or 1, 4- or 2, 6-naphthalene and the like); Or heteroallylene having 4 to 40 carbon atoms including group 14, 15, or 16 hetero elements (eg, 2,5-thiophendiedyl, 2,5-furanylene (2, 5- foranylene) and the like); Or cycloalkylene having 5 to 10 carbon atoms (eg, cyclohexyl, etc.); Or heterocycloalkylene having 4 to 40 carbon atoms (eg, 1, 3-dioxyl) containing a Group 14, Group 15, or Group 16 hetero element.
- arylene having 6 to 40 carbon atoms eg, substituted with at least one functional group selected from the group consisting
- R10 is hydrogen; halogen; Cyano; Nitro; NCS; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy having 6 to 30 carbon atoms; And it may be selected from the group consisting of substituted or unsubstituted aryl having 6 to 40 carbon atoms.
- cyclic olefin resin and the photoreactive copolymer obtained therefrom can be preferably used for the liquid crystal alignment film and the like to exhibit improved interaction with the liquid crystal molecules and excellent light response.
- the structure of formula la of the cyclic olefin compound in particular, the kind of the additionally substituted cyclic substituents (C2, C3) and the like may be converted into various arylene, heteroarylene, cycloalkylene, or heterocycloalkylene.
- the photoreactivity of the compound itself and the photoreaction copolymer obtained therefrom can be easily controlled. Accordingly, it is possible to obtain various photoreactive compounds, polymers, and the like, which exhibit excellent photoreaction properties against various lights, from such cyclic olepin compounds.
- the monomer that may be represented by Formula 2 may have a chemical structure in which a predetermined photoreactor (Formula 2a and 2b) is introduced into the cyclic olefin structure. Due to the chemical structure into which the photoreaction group is introduced, the cyclic olefin compound of Formula 2 may be used as the photoreaction compound by itself.
- a predetermined photoreactor Forma 2a and 2b
- the photo-reflective groups such as cinnamate structure
- the photoreflective groups can move (flow) or react relatively freely in a free space largely secured. Inhibition of other reaction groups or substituents thereof is minimized.
- the photoreaction groups in the photoreactive copolymer and the alignment layer may exhibit more excellent photoreactivity, orientation speed and photoalignment.
- optical reactions such as cinnamate structures are photo-aligned in a manner that causes dimerization and isomerization at the same time due to the excitation, and such photo-alignment can occur more smoothly and quickly without any inhibition in the large free space.
- the photoreactive copolymer and the alignment film prepared from the cyclic olefin compound can exhibit better light response, orientation and orientation rate.
- the light amplification groups can change the alignment direction relatively freely according to the change in the polarization direction.
- the change in the alignment direction according to the polarization direction may occur more smoothly, and may be preferably applied to a patterned retarder, a patterned cell alignment layer, or the like applied for realizing a stereoscopic image.
- the cyclic leulevine compound and the photobanung copolymer formed therefrom are obtained for various organic solvents. It was confirmed that good solubility can be exhibited. Accordingly, in the process of forming the alignment layer using the photoreactive copolymer, even if the amount of the organic solvent is reduced, the alignment layer may be more easily prepared by forming the photo-reflective copolymer satisfactorily and applying and drying the composition. . In addition, in such a process, coating and drying can be made easier, and the processability for forming the alignment film can be greatly improved.
- the photoreactive copolymer obtained by polymerizing the monomer represented by Formula 1 and the monomer represented by Formula 2 may be preferably used in a liquid crystal alignment layer or the like to exhibit improved interaction with the liquid crystal molecules and excellent light response.
- a liquid crystal alignment layer or the like to exhibit improved interaction with the liquid crystal molecules and excellent light response.
- photoreactivity and solubility in organic solvents can be adjusted to provide excellent photoreactivity to various lights, and at the same time improve processability for forming an alignment film.
- the R1 to R4 Polar functional groups that may be substituted for several Rl 'to R4' and the like, ie, polar functional groups containing at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron may be selected from the group consisting of the functional groups listed below
- polar functional groups including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, or boron.
- p is each independently an integer of 1 to 10
- R 5 is a substituted or unsubstituted C 1-20 linear or branched alkylene; Substituted or unsubstituted linear or branched alkenylene having 2 to 20 carbon atoms; .
- R 6 , R 7 and R 8 are each independently hydrogen; halogen; Substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms; Substituted or unsubstituted carbon number 2 Linear or branched alkenyl of from 20 to 20; Substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms; Substituted or .substituted aryl having 6 to 40 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 20 carbon atoms; And substituted or unsubstituted carbonyloxy having 1 to 20 carbon atoms.
- the photo-reflective copolymer it may be preferable to include a monomer that can be represented by the formula (1) and a monomer represented by the formula (2) in a molar ratio of about 9: 1 to about 1: 9, about It may be more desirable to include in a molar ratio of 6: 4 to about 4: 6.
- the photoreactive copolymer comprising a copolymer of the monomer represented by Formula 1 and the monomer represented by Formula 2 may include, for example, a repeating unit of Formula 3a or a repeating unit of Formula 3b. can do.
- R1, R2, R3, and R4 are as defined in Formula 1 of claim 1,
- R1 ', R2 R3', and R4 ' are as defined in Formula 2 of claim 1.
- Such photoreactive copolymers include repeating units derived from the two monomers described above.
- the above-described photoreactive copolymer includes a repeating unit derived from the monomer of Formula 1, thereby providing a structure of Formula la, in particular, a cyclic substituent (C2) and a specific functional group D further bonded via a specific functional group A.
- a cyclic substituent (C2) By having an additionally bonded cyclic substituent (C3) as a medium, it can exhibit improved interaction with the liquid crystal molecules and can exhibit excellent light response.
- C3 cyclic substituent
- it can exhibit excellent interaction with the liquid crystal molecules and can exhibit excellent light response.
- the cyclic substituents C2 and C3 ring among various arylene, heteroarylene, cycloalkylene : heterocycloalkylene it is possible to exhibit excellent light response to various lights.
- the above-described light semi-coagulant copolymer includes a repeating unit derived from the monomer of the formula (2), due to the bulky structure bonded to the end of the photoreactor, a large free space can be secured between the photo-fungi group
- the light reaction stages can move (flow) or react relatively freely in the free space, which is largely secured, and can exhibit better light response, orientation speed, and optical orientation.
- the optical reaction groups can change the orientation direction relatively freely, The change may occur more smoothly, and may be preferably applied to a patterned retarder, a patterned cell alignment layer, and the like.
- m: m ' may be preferably about 9: 1 to about 1: 9, and more preferably about 6: 4 to about 4: 6.
- the photoreactive copolymer includes a norbornene-based repeating unit of Formula 3a or 3b as a main repeating unit.
- Such norbornene-based repeating units are structurally rigid, and the photobanung copolymer comprising them has a known light spot because the glass transition temperature (Tg) is relatively high, about 300 ° C. or higher, preferably about 300 to 350 ° C. It can exhibit excellent thermal stability compared to male copolymers.
- the photo-banung copolymer may include only one or more repeating units selected from the group consisting of a repeating unit of the formula or 3b, it may be a copolymer further comprising other types of repeating units.
- repeating units are any olefinic repeats with or without a cinnamate-based, chalcone-based or azo-based photoreactor (e.g., a general photoreactor with no bulky aralkyl structure terminated).
- it may be an acrylate-based repeating unit or a cyclic olefin-based repeating unit. Examples of such repeating units are disclosed in patent publication no. 2010-0021751 and the like.
- the photo-banung copolymer is about 50 mol% or more, specifically about 50 to about 100 mol%, in order not to impair various properties such as excellent orientation and orientation rate according to the repeating units of Formula 3a or 3b. it may comprise a recurring unit of the formula 3a or 3b in an amount of about 70 mole 0/0 or more. In addition, the repetition of the formula 3a or 3b constituting the photo-reflective copolymer The unit may have a degree of polymerization of about 50 to about 5,000, preferably a degree of polymerization of about 100 to about 4,000, more preferably of about 1,000 to about 3,000.
- the photoreaction polymer may have a weight average molecular weight of about 10,000 to about 1,000,000 g / mol, or about 20,000 to about 500,000 g / mol, or about 80,000 to about 300,000 g / m. Accordingly, the light semi-coagulant copolymer may be appropriately included in the coating composition for forming the alignment layer, and may exhibit excellent coating property, but the alignment layer formed therefrom may exhibit excellent alignment.
- the photoreactive copolymers described above may exhibit photoreactivity under exposure of polarized light having a wavelength of about 150 to about 450 nm, for example, a wavelength of about 200 to about 400 nm, more specifically a wavelength of about 250 to about 350 nm. Excellent photoreactivity, orientation, and the like can be exhibited under the exposure of the polarized light of the UV region having a ratio.
- a method for producing the photoreactive copolymer described above there is provided a method for producing the photoreactive copolymer described above.
- a method for preparing a photoreactive copolymer is represented by the monomer represented by the following formula (1) and the following formula (2) in the presence of a catalyst composition comprising a procatalyst and a cocatalyst including a Group 10 transition metal. Addition polymerization of the monomer to form a repeating unit of Formula 3a.
- n, m ', and k are integers from 50 to 5000
- q ' and q' are integers from 0 to 4,
- R1, R2, R3, and R4 are as defined in Formula 1 of claim 1, and R1 ', R2', R3 ', and R4' are as defined in Formula 2 of claim 1.
- the polymerization reaction may be performed at a temperature of about 10 ° C to about 200 ° C. If the reaction temperature is less than about 10 ° C. polymerization activity may be lowered, and if the reaction temperature is greater than about 200 ° C catalyst is decomposed it is not preferred.
- the cocatalyst may be weakly coordinated with the metal of the procatalyst.
- a second co-catalyst for providing a compound comprising a group 15 electron donor ligand may comprise one or more selected from the group consisting of.
- the cocatalyst may be a catalyst mixture comprising a first cocatalyst which provides the Lewis base, and optionally a second cocatalyst of a compound comprising a neutral Group 15 electron donor ligand.
- the catalyst mixture is the first relative to 1 mol of the procatalyst
- the promoter may comprise about 1 to about 1000 moles, and the second promoter may comprise about 1 to about 1000 moles. If the content of the first or second cocatalyst is too small, the catalyst activation may not be properly performed, on the contrary, if too large, the catalytic activity may be lowered.
- the first cocatalyst which provides a Lewis base capable of weakly coordinating with the metal of the procatalyst is easily reacted with the Lewis base to form a vacancy in the transition metal, and also to stabilize the transition metal thus formed.
- Compounds that provide weak coordination with metal compounds or compounds that provide them can be used.
- borate such as B (C 6 F 5 ) 3 or borate such as dimethylanilinium tetrakis (pentafluorophenyl) borate, methylaluminoxane (MAO) or A1 (C 2 H 5 ) there is a transition metal halide such as an alkyl aluminum, or AgSbF 6, such as 3.
- an alkyl phosphine, a cycloalkyl phosphine, or a phenyl phosphine may be used as the second cocatalyst to provide a compound including the neutral group 15 electron donor ligand.
- the said 1st promoter and the 2nd promoter can also be used separately, it can also be used as a compound which makes these two promoters into one salt, and activates a catalyst.
- a compound or the like made by ion bonding an alkyl phosphine and a borane or a borate compound may be used.
- the photo-reflective copolymer may be an olefinic repeat unit, a cyclic olefinic repeat unit or In the case of further including an acrylate-based repeating unit, these repeating units are formed by a conventional manufacturing method of each repeating unit, and the chemical formula prepared by the above-described method
- Copolymerization with 1 ⁇ 4 repeating units can yield the photoreflexive copolymer.
- the photoreactive copolymer when the photoreactive copolymer includes a repeating unit of Formula 3b, it may be prepared according to another embodiment.
- R1, R2, R3, and R4 are as defined in Formula 1 of claim 1,
- R 1 ′, R 2 ′, R 3 ′, and R 4 ′ are the same as defined in Formula 2 of claim 1, and the above formulas la, 2a, and 2b are as defined in claim 1.
- the ring-opening may proceed while hydrogen is added to the double bond in the norbornene ring included in the monomer of Formula 1, and the polymerization proceeds with the repeating unit of Formula 3b and the like.
- Male co-polymers can be prepared. Black may be polymerized and the ring opening proceeds sequentially to produce the photo-banung copolymer.
- the introduction of the photobanung group may proceed by a condensation of the ring-opening polymer with a carboxylic acid compound or an acyl chloride compound having a photoreactive group corresponding to formulas la, 2a, and 2b.
- the monomer represented by Formula 1 and the monomer represented by Formula 2 may be carried out to form a repeating unit of Formula 3b.
- n, m ', and k are integers from 50 to 5000
- R1, R2, R3, and R4 are as defined in Chemical Formula 1 of claim 1, and R1 ', R2', R3 ', and R4' are as defined in Chemical Formula 2 of item 1.
- the ring-opening polymerization comprises a procatalyst comprising a transition metal of Group 4 (e.g., Ti, Zr, Hf), Group 6 (e.g., Mo, W), or Group (e.g., Ru, Os), and the metal of the procatalyst.
- a catalyst mixture consisting of a cocatalyst that provides a weakly coordinating Lewis base and optionally a group 15 and 16 activator that can enhance the activity of the procatalyst metal, and the like. Can be.
- a catalyst mixture in the presence of such a catalyst mixture, about 1 to about 100 mol% of linear alkene, such as 1-alkene and 2-alkene, which can adjust the molecular weight size, is added to the monomer, and thus, about 10 ° C to about 200 ° C.
- the polymerization may be carried out at a temperature of C, and about 1 to about 30 weights of a catalyst comprising a transition metal of Group 4 (eg Ti, Zr) or Group 8 to 10 (eg Ru, Ni, Pd)
- the reaction may be carried out by hydrogenation of the double bond in the norbornene ring at about 10 to about 250 ° C. by adding%.
- reaction temperature is too low, there is a problem that the polymerization activity is lowered, and if the reaction temperature is too high, the catalyst is decomposed, which is not preferable.
- hydrogenated reaction reaction temperature is too low, there is a problem that the activity of the hydrogenated reaction reaction is lowered, and if too high a problem that the catalyst is decomposed, it is not preferable.
- the catalyst mixture may be added to one mole of the procatalyst comprising a transition metal of Group 4 (eg Ti, Zr, Hf), Group 6 (eg Mo, W), or Group 8 (eg Ru, Os) From about 1 to about 100,000 moles of cocatalyst, which provides a Lewis base capable of weakly coordinating with the metal of the procatalyst, and optionally a group of neutral Group 15 and 16 elements that can enhance the activity of the procatalyst metal Activator comprises about 1 to about 100 moles per mole of procatalyst.
- a transition metal of Group 4 eg Ti, Zr, Hf
- Group 6 eg Mo, W
- Group 8 eg Ru, Os
- the content of the promoter is less than about 1 mole, there is a problem that the catalyst activation is not made, and when larger than about 100,000 moles, there is a problem that the catalyst activity is lowered, which is not preferable.
- the activator may not be necessary depending on the type of procatalyst. If the content of the activator is less than about 1 mole, there is a problem that the catalyst activation is not made, and if it is greater than about 100 moles there is a problem that the molecular weight is lowered, which is not preferable.
- the content of the catalyst containing a transition metal of Group 4 (eg Ti, Zr) or Groups 8 to 10 (eg Ru, Ni, Pd) used in the hydrogenation reaction is less than about 1% by weight of the hydrogen, hydrogen There is a problem that the addition does not work well If greater than 30% by weight there is a problem that the polymer is discolored is not preferred.
- the procatalyst comprising a transition metal of Group 4 (e.g. Ti, Zr, Hf), Group 6 (e.g. Mo, W), or Group 8 (e.g. Ru, Os) may be added to the cocatalyst for providing Lewis acid.
- Transitions such as TiCI 4 , WC1 6 , MoCl 5, or RuCl 3 or ZrCl 4 , which have functional groups that readily participate in the Lewis acid-base reaction and are separated from the central metal so that they can be easily separated and converted into a catalytically active species. It may refer to a metal compound.
- the co-catalyst that provides a Lewis base that can weakly coordinate with the metal of the procatalyst is borane or borate such as B (C 6 F 5 ) 3 , methylaluminoxane (MAO) or A1 (C 2 H 5 ) 3, it is possible to use an alkyl aluminum, alkyl aluminum halide, aluminum halide, such as A1 (CH 3) 2 C1.
- substituents such as lithium, magnesium, germanium, lead, zinc, tin, and silicon may be used. In this way, the compound easily reacts with the Lewis base to form a vacancy of the transition metal and also weakly coordinates with the transition metal compound to provide a stabilized transition metal or a compound providing the same.
- An activator of the polymerization can be added, it may not be necessary depending on the type of procatalyst.
- An activator including neutral group 15 and 16 elements capable of enhancing the activity of the procatalyst metal is water, methanol, ethane, isopropyl alcohol, benzyl alcohol, pemol, ethyl mercaptan (ethyl) mercaptan), 2-chloroethane, trimethylamine, triethylamine, pyridine, ethylene oxide, benzoyl peroxide, t-butyl peroxide, and the like. .
- Catalysts containing transition metals of Group 4 (e.g. Ti, Zr) or Groups 8 to 10 (e.g. Ru, Ni, Pd) used in the hydrogenation reaction are homogeneous forms that can be immediately mixed with the solvent. Or a metal catalyst complex supported on the particulate support.
- the particulate support is silica, titania, silica / chromia, silica / chromia / titania, silica / alumina, aluminum phosphate gel, silanized silica, silica hydrogel, montmorillonite clay or zeolite. .
- the photo-banung copolymer further contains an olefin type repeating unit, a cyclic olefinic repeating unit, or an acrylate type repeating unit, these repeating units are formed by the conventional manufacturing method of each repeating unit,
- the photo-reflective copolymer may be obtained by copolymerization with a repeating unit represented by Chemical Formula 3b.
- an alignment film comprising the above-mentioned light semicoherent co-polymer.
- Such an alignment film may also include an alignment film in the form of a film as well as a thin film.
- a liquid crystal retardation film comprising such an alignment film and a liquid crystal layer on the alignment film.
- Such an alignment film and a liquid crystal retardation film may be manufactured using components and manufacturing methods known in the art to which the present invention pertains, except that the above-described light semicoagulant copolymer is included as a photoalignment polymer.
- the alignment layer may be formed by mixing the photo-banung co-polymer, the binder and the photoinitiator and dissolving it in an organic solvent to obtain a coating composition, and then coating and drying the coating composition on a substrate and performing UV curing.
- the photoreactive copolymer since the photoreactive copolymer exhibits excellent solubility in organic solvents, the process of forming the alignment layer may be more easily performed, and the amount of organic solvents used may be further reduced.
- a (meth) acrylate-based compound may be used as the binder, and more specifically, a pentaerythrone triacrylate, a dipentaerythroxy nucleated arte, trimethylolpropane triacrylate, or tris ( 2-acryloyloxyethyl) isocyanurate, etc. can be used.
- a conventional photoinitiator known to be usable for the alignment layer may be used without particular limitation, and for example, a photoinitiator known under the trade names Irgacure 907 and 819 may be used.
- organic solvent toluene, anisole, chlorobenzene, dichloroethane, cyclonucleic acid, cyclopentane, propylene glycol methyl ether Acetates and the like can be used. Since the photo-banung copolymer described above shows excellent solubility in various organic solvents, various organic solvents may be used without particular limitation.
- the solid content concentration including the photoreactive copolymer, the binder and the photoinitiator may be about 1 to about 15 weight 0 /.
- the solid content concentration including the photoreactive copolymer, the binder and the photoinitiator may be about 1 to about 15 weight 0 /.
- about 10 to about 15 weight 0 to cast the alignment layer in the form of a film / 0 is preferred, and from about 1 to about 5 weight percent is preferred to form a thin film.
- the alignment layer thus formed may be formed on the substrate, for example, as illustrated in FIG. 1, and may be formed under the liquid crystal to align the same.
- the substrate may be a substrate containing a cyclic polymer, a substrate containing an acrylic polymer or a substrate containing a cellulose polymer, and the like, and the coating-composition may be a bar coating, spin coating, blade coating, or the like. Coating on the substrate in various ways and then UV cured to form an alignment layer.
- Photo-alignment may occur by the UV curing.
- alignment may be performed by irradiating polarized UV in a wavelength range of about 150 to about 450 ran.
- the intensity of the exposure may be about 50 mJ / cii to about 10 J / ciif of energy, preferably about 500 mJ / cii to 5 J / cin 2 of energy.
- the UV may be a polarizing device using a substrate coated with a dielectric anisotropic substance on a transparent substrate surface such as quartz glass, soda lime glass, or soda lime free glass, or a polarizing plate on which fine aluminum or metal wires are deposited, or quartz.
- Polarized UV selected from polarized UV may be applied by passing or reflecting through a Brewster polarizer or the like due to reflection of glass.
- the substrate temperature at the time of irradiating the said UV normal temperature is preferable. However, in some cases, UV irradiation was also possible in a heated state within a temperature range of about 100 ° C or less.
- the film thickness of the final coating film formed by the above series of processes is preferably about 30 to about 1,000 nm.
- An alignment film is formed by the method described above, and a liquid crystal worm is formed thereon. According to a conventional method, a liquid crystal retardation film can be manufactured.
- the alignment layer includes the photoreactive copolymer, the alignment layer may exhibit excellent interaction with the liquid crystal molecules, thereby enabling effective photo alignment.
- the above-described alignment film or liquid crystal retardation film may be applied to an optical film or an optical filter for implementing a stereoscopic image.
- a display device including the alignment layer may be a liquid crystal display device in which the alignment layer is included for alignment of liquid crystals, or a stereoscopic image display device included in an optical film or a filter such as a liquid crystal retardation film for realizing a stereoscopic image.
- the configuration of these display elements is in accordance with the configuration of a conventional device, except that the above-described light semi-coagulant copolymer and an alignment film are included, the detailed description thereof will be omitted.
- the operation and effects of the invention will be described in more detail with reference to specific examples of the invention. However, these embodiments are only presented as an example of the invention, whereby the scope of the invention is not determined.
- Example 1-5 and Comparative Example 1 is a photo-reactive polymer 3 parts by weight 0/0, an acrylate-based binder (PETA) according to 1.0 weight 0/0, a photoinitiator (Irgacure 907, manufacturer: Ciba) 0.5 parts by weight 0 / Dissolved in toluene solvent to zero and the solution was bar-coated by dropping it onto a COP film.
- PETA acrylate-based binder
- Irgacure 907 manufacturer: Ciba
- polarized UV (15mJ / cm 2 ) was irradiated.
- half of the cured alignment film was covered, rotated by 90 degrees, and irradiated with the same polarized UV again.
- the amount of light of polarized UV was adjusted by time.
- A-plate liquid crystal (manufacturer: Merck, 25 wt% of a leuene solution) was dropped on the alignment film and bar-coated, UV was irradiated at 15mJ / cm 2 , and the liquid crystal was cured to obtain a retardation film.
- Each retardation film prepared above was observed by a polarizing microscope between two vertically arranged polarizers to evaluate the orientation.
- the retardation film is placed between two polarizers arranged vertically with respect to a COP film having a thickness of 100 (manufacturer: Zeon, product name: Zeonor).
- the degree of light leakage was measured by observing with a polarizing microscope how much light passes through the polarizer and the retardation film. At this time, based on the degree of light leakage was evaluated based on 10 points.
- phase difference value of the retardation film was measured using Axoscan (made by Axomatrix). At this time, the phase difference value of the film surface direction was measured using the light of 550 nm wavelength band.
- the alignment direction of the liquid crystal is uniform regardless of the wavelength of the incident light, showing excellent alignment, even in the secondary orientation, in the film plane
- the retardation value is about 131 to 132 nm, it can be seen that the anisotropy by the liquid crystal is well implemented.
- the orientation is somewhat excellent in the primary alignment
- the alignment direction of the liquid crystal in the secondary alignment _ it is confirmed that the light leakage phenomenon occurs
- the retardation value is low as about 112 nm, it can be seen that the anisotropy is not well implemented.
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Abstract
Description
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US14/915,512 US10047183B2 (en) | 2013-09-30 | 2014-09-26 | Photoreactive copolymer and alignment layer comprising the same |
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EP3018158A1 (en) | 2016-05-11 |
KR20150037583A (ko) | 2015-04-08 |
CN105593252A (zh) | 2016-05-18 |
TW201522392A (zh) | 2015-06-16 |
CN105593252B (zh) | 2019-05-28 |
TWI513720B (zh) | 2015-12-21 |
JP6401282B2 (ja) | 2018-10-10 |
US20160222147A1 (en) | 2016-08-04 |
KR101719686B1 (ko) | 2017-03-24 |
EP3018158A4 (en) | 2017-02-01 |
US10047183B2 (en) | 2018-08-14 |
JP2016535157A (ja) | 2016-11-10 |
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