WO2016204178A1 - Film d'alignement, et composition pour films d'alignement - Google Patents

Film d'alignement, et composition pour films d'alignement Download PDF

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Publication number
WO2016204178A1
WO2016204178A1 PCT/JP2016/067803 JP2016067803W WO2016204178A1 WO 2016204178 A1 WO2016204178 A1 WO 2016204178A1 JP 2016067803 W JP2016067803 W JP 2016067803W WO 2016204178 A1 WO2016204178 A1 WO 2016204178A1
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WIPO (PCT)
Prior art keywords
compound
alignment film
partial structure
group
film
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PCT/JP2016/067803
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English (en)
Japanese (ja)
Inventor
住谷　直子
晃子 矢部
藤森　尚美
政昭 西村
充哉 青葉
輝恒 大澤
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三菱化学株式会社
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Application filed by 三菱化学株式会社 filed Critical 三菱化学株式会社
Priority to JP2017525261A priority Critical patent/JP6922736B2/ja
Priority to CN201680031589.9A priority patent/CN107683427B/zh
Priority to KR1020177036033A priority patent/KR102560883B1/ko
Publication of WO2016204178A1 publication Critical patent/WO2016204178A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films

Definitions

  • the present invention relates to an alignment film composition used for forming an anisotropic dye film formed by a wet film formation method, an alignment film obtained using the alignment film composition, and an optical element.
  • a linearly polarizing film or a circularly polarizing film is used to control optical rotation and birefringence in display.
  • light emitting display elements such as organic light emitting diodes (OLED) and input / output elements such as touch panels
  • circularly polarizing films are used to prevent reflection of external light.
  • iodine-type polarizing films prepared by dyeing polyvinyl alcohol (PVA) with iodine, stretching and crosslinking the polarizing films (anisotropic dye films) have been widely used.
  • iodine used as a dichroic material of this film has a high sublimation property, when used in a polarizing film, its heat resistance and light resistance are not sufficient. For this reason, a polarizing film using an organic dye as a dichroic substance has been studied.
  • an organic dye having dichroism is dissolved or adsorbed in polyvinyl alcohol, and the dye is oriented by stretching it into a film in one direction.
  • the method to obtain is mentioned (patent document 1).
  • a polarizing film using polyvinyl alcohol has a problem that the film is likely to shrink due to a change in temperature and humidity.
  • a defect called a frame failure or a frame unevenness occurs in a large-sized display element such as a liquid crystal television or a vehicle-mounted display element that requires durability at high temperatures such as a car navigation monitor.
  • a polarizing film is formed by forming a film containing a dye on a substrate such as glass or a transparent film by using a wet film forming method and orienting the dye using an intermolecular interaction or the like.
  • the method to obtain is mentioned (patent document 2).
  • the orientation of the dye can be controlled by subjecting the base material to an orientation treatment, and studies using a photo-alignment film have been made.
  • the base material used for rubbing treatment which is a general method for producing an alignment film, the base material itself is rubbed or the alignment film for liquid crystal is only diverted (Patent Documents 3 and 4). ).
  • liquid crystal alignment film polyimide is generally used in many cases, but an epoxy resin is also being studied (Patent Document 5).
  • Patent Document 5 it is difficult to apply an alignment film for liquid crystal as an alignment film of an anisotropic dye film obtained by a wet film formation method because the material to be aligned and required characteristics are different.
  • the lyotropic liquid crystal has a mesogen size different from that of the thermotropic nematic liquid crystal because the molecules form a column structure.
  • an alignment film suitable for a thermotropic nematic liquid crystal cannot be used as an alignment film for an anisotropic dye film obtained by a wet film formation method.
  • a water-soluble material to be aligned may be applied on the alignment film, and characteristics and the like that are not required for the alignment film for liquid crystal Necessary.
  • Patent Document 2 a technique for creating a polarizing film by applying a composition for an anisotropic dye film obtained by a wet film formation method onto a polymer surface such as polyethylene terephthalate has been introduced (Patent Document 2). Since the plastic substrate used for these has low heat resistance, it is required to lower the temperature of the manufacturing process of the liquid crystal display. In order to increase the brightness of a liquid crystal display, it has been studied to use a colorant for a color filter as a dye.
  • the dye since the dye has low heat resistance, it is required to set the temperature of the process after producing the color filter to 180 ° C. or lower, which is lower than the conventionally used temperature (Patent Document 6). Therefore, it is required that the alignment film for the anisotropic dye film is also manufactured at a temperature lower than the conventionally used temperature.
  • Japanese Patent Laid-Open No. 3-12606 Japanese National Table No. 8-511109 Japanese Unexamined Patent Publication No. 1-161202 Japanese Unexamined Patent Publication No. 2010-72521 Japanese Unexamined Patent Publication No. 10-330756 Japanese Unexamined Patent Publication No. 2011-253054
  • the present inventors have been able to produce an alignment film having a high alignment regulating ability for an anisotropic dye film composition even at a low temperature by using a specific composition for the alignment film.
  • the present inventors have found that the anisotropic dye film formed on the alignment film has high alignment characteristics.
  • the alignment film of the present invention has an anisotropic dye film formed on the alignment film by performing surface treatment such as rubbing to increase the alignment regulating force on the composition for the anisotropic dye film.
  • the orientation characteristics can be further improved.
  • the present invention has been accomplished based on these findings.
  • the gist of the present invention resides in the following [1] to [8].
  • [1] An epoxy resin cured alignment film comprising at least one of the partial structure (P1) and the partial structure (P2), An epoxy resin cured alignment film, wherein the proportion of at least one of the partial structure (P1) and the partial structure (P2) in the epoxy resin cured alignment film is 0.5% by mass or more.
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P2) is represented by the following formula (1).
  • R 1 represents a divalent group containing a hetero atom and having an unsaturated bond, and the ring bonded to R 1 is a single ring.
  • An epoxy resin cured alignment film that includes a partial structure represented by the following formula (2).
  • ring Y 1 represents a heterocyclic ring which may have a substituent.
  • An alignment film composition comprising at least one of compound group I and compound group II, The alignment film composition, wherein a ratio of at least one of the partial structure (P1) and the partial structure (P3) in the alignment film composition excluding the solvent is 0.5% by mass or more.
  • the compound group I is a compound A having an epoxy group and at least one of the partial structure (P1) and the partial structure (P3)
  • the compound group II is a compound B having a functional group that reacts with an epoxy group, and at least one of a partial structure (P1) and a partial structure (P3), and a compound C having an epoxy group
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P3) is represented by the following formula (6).
  • R 3 represents a divalent group having an unsaturated bond including a hetero atom, and the ring bonded to R 3 is a single ring.
  • An alignment film composition comprising a reaction mixture having at least one of a partial structure (P1) and a partial structure (P4), The alignment film composition, wherein a ratio of at least one of the partial structure (P1) and the partial structure (P4) in the alignment film composition excluding the solvent is 0.5% by mass or more.
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P4) is represented by the following formula (7).
  • R 4 represents a divalent group containing a hetero atom and having an unsaturated bond.
  • An alignment film composition comprising at least one of compound group III and compound group IV.
  • Compound Group III is Compound E having an epoxy group and a partial structure represented by the following formula (8)
  • the compound group IV is a compound F having a functional group that reacts with an epoxy group, a compound F having a partial structure represented by the following formula (8), and an epoxy group.
  • Z 1 represents a divalent group having a cyclic imide structure
  • Z 2 and Z 3 each independently represent a direct bond or any divalent group
  • Z 4 represents a divalent group having an aromatic ring
  • n represents an integer of 1 or more and 500 or less.
  • the alignment characteristics of the anisotropic dye film formed on the alignment film can be enhanced.
  • an alignment film having a high alignment regulating ability to the anisotropic dye film composition can be produced even at a low temperature.
  • the film obtained from the alignment film composition of the present invention is formed on the alignment film by increasing the alignment regulating force to the anisotropic dye film composition by performing a surface treatment such as rubbing. The orientation characteristics of the anisotropic dye film can be further enhanced.
  • the anisotropic dye film referred to in the present invention differs from the electromagnetic properties in any two directions selected from a total of three directions in the three-dimensional coordinate system of the thickness direction of the dye film and any two orthogonal planes. It is a dye film having anisotropy.
  • the electromagnetic property include optical properties such as absorption and refraction, and electrical properties such as resistance and capacitance.
  • Examples of the film having optical anisotropy such as absorption and refraction include a linearly polarizing film, a circularly polarizing film, a retardation film, and a conductive anisotropic film.
  • the alignment film of the present invention is a film that imparts an alignment function to an anisotropic dye film or the like formed by a wet film formation method described later.
  • the alignment film of the present invention is an epoxy resin cured alignment film
  • the alignment film includes at least one of a partial structure (P1) and a partial structure (P2),
  • the ratio of at least one of the partial structure (P1) and the partial structure (P2) in the alignment film is 0.5% by mass or more.
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P2) is represented by the following formula (1).
  • R 1 represents a divalent group containing a hetero atom and having an unsaturated bond, and the ring bonded to R 1 is a single ring.
  • the alignment film of the present invention is an epoxy resin cured alignment film.
  • the epoxy resin cured alignment film includes a cured epoxy monomer and / or epoxy oligomer having an epoxy group in the molecule. Whether it is an epoxy resin cured alignment film can be confirmed by IR, solid state NMR or the like.
  • Epoxy resin cured alignment film (1) The epoxy resin cured alignment film is hereinafter referred to as at least one of the partial structure (P1) and the partial structure (P2) (hereinafter sometimes referred to as “partial structure of molecular orientation” or “partial structure (P)”). Including.
  • the reason why the alignment film of the present invention gives a high alignment function to an anisotropic dye film formed by a wet film formation method is not clear, but the following may be considered.
  • “molecular orientation” means, for example, that molecules, molecular chains, and the like are arranged in a specific direction as described in detail in Molecular Orientation Technology in Organic Electronics (CMC Publishing Co., Ltd., 2007), The property of forming an anisotropic structure.
  • the partial structure (P) can form an anisotropic regular structure, and thereby the orientation regulating force to the composition for anisotropic dye film can be increased. Furthermore, by subjecting the alignment film to a surface treatment such as rubbing, a structure with further increased anisotropy regularity is formed, and the alignment regulating force to the composition for anisotropic dye film is increased.
  • anisotropic dyes unlike liquid crystal molecules, have a relatively large association (column) structure of about 100 to several hundreds of millions of anisotropic dyes. Compared to the thermotropic nematic liquid crystal, it is considered that alignment is difficult to follow the alignment film. Therefore, in order to orient an anisotropic dye film composition containing an anisotropic dye, an alignment film having a high alignment regulating force is required.
  • the alignment film of the present invention is anisotropic for the above reasons. It has a high orientation regulating power to the composition for a functional dye film.
  • the ratio of the partial structure (P1) and the partial structure (P2) in the epoxy resin cured alignment film is 0.5% by mass or more.
  • it is 1 mass% or more, More preferably, it is 5 mass% or more, More preferably, it is 10 mass% or more, Most preferably, it is 20 mass% or more.
  • it is preferably 99% by mass or less, more preferably 90% by mass or less, still more preferably 85% by mass or less, and particularly preferably 80% by mass or less. By being in this range, it tends to be easy to form a film and to improve the orientation regulating power to the anisotropic dye film composition.
  • the said ratio shows the ratio of the sum of the said partial structure (P1) and partial structure (P2) in an epoxy resin cured alignment film, and a partial structure (P1) or partial structure (P2) in an epoxy resin cured alignment film
  • P1 and P2 in an epoxy resin cured alignment film
  • the partial structure (P1) is an aromatic ring containing a hetero atom.
  • the partial structure (P1) is not particularly limited as a single ring or a condensed ring as long as it has aromaticity, and may be a condensed ring of an aromatic ring and an alicyclic ring.
  • the alignment film has the partial structure (P1), the skeleton of the molecular-oriented partial structure has high rigidity, and a charge-polarized structure is formed. It becomes easy to take aggregation and association within a molecule, or a spontaneous arrangement of a partial structure of molecular orientation.
  • the number of condensed rings it has is not particularly limited, but is 2 or more, preferably 5 or less, more preferably 3 or less. By being in this range, it tends to be easy to take a spontaneous arrangement of partial structures with molecular orientation while improving flatness and rigidity.
  • a hetero atom is not specifically limited, In order to improve the polarizability in a molecule
  • the number of heteroatoms contained in the partial structure (P1) is not particularly limited, but is 1 or more, preferably 4 or less, more preferably 3 or less. By being in this range, a charge bias (polarization) structure tends to be easily formed.
  • the partial structure (P1) includes, for example, an aromatic ring such as a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a biphenylene ring, and a fluorene ring, and a heterocyclic ring having a hetero atom such as nitrogen, oxygen, and sulfur in the ring.
  • an aromatic ring such as a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a biphenylene ring, and a fluorene ring
  • a heterocyclic ring having a hetero atom such as nitrogen, oxygen, and sulfur in the ring.
  • a condensed ring an aromatic heterocycle having a heteroatom in the ring, such as pyrimidine, pyrazine, pyridazine, imidazole, triazine, naphthyridine
  • a condensed ring of an aromatic ring and a heterocyclic ring is preferable because having a plurality of rings tends to increase the planarity and rigidity of the molecule and promote the spontaneous arrangement of the molecule.
  • phthalimide, benzoxazole, benzimidazole, triazine, quinoxaline, etc. shown below have stronger intermolecular or intramolecular interactions, causing aggregation or association between molecules or molecules, making it easier to arrange molecules. It is particularly preferable because of its tendency.
  • the partial structure (P1) is particularly preferably a structure represented by the following formula (2). This is because the planarity and rigidity of the molecules increase, and the molecules tend to be easily arranged.
  • Ring Y 1 represents a heterocyclic ring which may have a substituent.
  • Ring Y 1 has the same meaning as ring Y 1 in formula (3) below, and the preferred range is also the same. Further, the ring Y 1 and ring Y 1 condensed with may have a benzene ring substituents are also the same. Further, the positions where the ring Y 1 and the benzene ring condensed with the ring Y 1 are connected to the structure in the other cured epoxy resin alignment film are also synonymous.
  • the partial structure (P2) is a partial structure represented by the following formula (1).
  • the charge orientation (polarization) structure of the molecular orientation partial structure is further increased in the epoxy resin cured alignment film. Easy to form.
  • R 1 represents a divalent group containing a hetero atom and having an unsaturated bond, and the ring bonded to R 1 is a single ring.
  • R 1 represents a divalent group containing a hetero atom and having an unsaturated bond.
  • Unsaturated bond refers to a chemical bond that is divalent or more bonded between adjacent atoms, such as a bond between carbons such as —C ⁇ C—, and a carbon and heteroatom such as —C ( ⁇ O) —. And a bond between heteroatoms such as — (O ⁇ ) S ( ⁇ O) —.
  • R 1 is a divalent group containing a hetero atom and having an unsaturated bond, the R 1 portion has planarity and polarizability, and the intermolecular or intramolecular interaction tends to become stronger. .
  • the divalent group is not particularly limited as long as it has a hetero atom and an unsaturated bond, and may be composed of a hydrocarbon group and a hetero atom.
  • the carbon number is 1 or more, and the upper limit of the carbon number is preferably 5 or less, more preferably 4 or less. Within these ranges, the planarity of the molecule tends to be obtained.
  • the hetero atom is not particularly limited, but preferably includes one selected from the group consisting of O, S and N in order to increase the polarizability in the molecule.
  • the two benzene rings to which R 1 is bonded are monocyclic.
  • the epoxy resin cured alignment film has both the partial structure (P1) and the partial structure (P2) as described later, they may be condensed.
  • the substituent that the two benzene rings to which R 1 is bonded may have, but is not particularly limited, for example, independently, an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms. Amino group, hetero atom, nitro group, hydroxyl group, halogen atom, —C ( ⁇ O) — group and the like.
  • the partial structure represented by the formula (1) is not particularly limited, but aromatic phenyl esters, aromatic phenyl amides, chalcones, diphenyl ketones, diphenyl sulfones and the like shown below are molecular planarity and rigidity. Is increased, a charge-biased (polarized) structure is formed, and the intermolecular or intramolecular interaction tends to become stronger, which is particularly preferable.
  • the epoxy resin cured alignment film only needs to include the partial structure (P1) and the partial structure (P2).
  • having both structures further enhances intermolecular or intramolecular interaction. It is preferable because aggregation or association between molecules or within a molecule occurs and the molecules tend to be arranged easily.
  • the two benzene rings to which R 1 is bonded are: It may be a part of the partial structure (P1). Specific examples of the partial structure having both the partial structure (P1) and the partial structure (P2) are shown below.
  • the epoxy resin cured alignment film of the present invention includes a partial structure represented by the following formula (3).
  • the partial structure represented by Formula (3) the planarity and rigidity of the molecule increase, and the ⁇ - ⁇ interaction becomes stronger.
  • a charge polarization structure is formed in the molecule, and aggregation or association occurs between molecules or within the molecule due to hydrogen bonding or donor-acceptor interaction, which facilitates the arrangement of the molecules.
  • ring Y 1 represents a heterocyclic ring which may have a substituent.
  • the hetero atom of ring Y 1 is not particularly limited, but preferably includes one selected from the group consisting of O, S, and N in order to increase the polarizability in the molecule.
  • the number of heteroatoms contained in ring Y 1 is not particularly limited, but is 1 or more, preferably 4 or less, more preferably 3 or less. By being in this range, a charge bias (polarization) structure tends to be easily formed.
  • the number of atoms forming the ring Y 1 is not particularly limited, and is 3 (3-membered ring) or more, preferably 4 (4-membered ring) or more. Further, it is preferably 8 (8-membered ring) or less, more preferably 6 (6-membered ring) or less. Within this range, the planarity and rigidity of the molecule tend to increase.
  • the benzene ring condensed with the ring Y 1 and the ring Y 1 may have a substituent.
  • substituents examples include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, a hetero atom, a nitro group, a hydroxyl group, a halogen atom, and —C ( ⁇ O ) -Group and the like.
  • the position at which the ring Y 1 and the benzene ring condensed with the ring Y 1 are connected to the structure in the other cured epoxy resin alignment film is not particularly limited, but the molecule including the partial structure represented by the formula (3) When the partial structures (3) are connected so that the aspect ratio (molecular length uniaxial ratio) is increased, the linearity of the molecule is obtained and the orientation function to the anisotropic dye film tends to be improved. Therefore, it is preferable.
  • the connecting position with the molecule is preferably substituted with an element away from the condensation position of the ring Y 1 of formula (3) and the aromatic ring.
  • the above structure has high molecular linearity, so that the crystallinity is high and the orientation regulating power to the anisotropic dye tends to be improved. Moreover, it becomes easy to form an anisotropic regular structure in which the regularity of the partial structure represented by the formula (3) is increased during surface treatment such as rubbing, and the regularity of the obtained alignment film can be increased. .
  • the proportion of the partial structure represented by the formula (3) in the epoxy resin cured alignment film is not particularly limited, but is preferably 0.5% by mass or more, more preferably 1% by mass or more, and further more preferably 5% by mass or more. Preferably, it is more preferably 10% by mass or more, and particularly preferably 20% by mass or more. Moreover, it is preferable that it is 99 mass% or less, It is more preferable that it is 90 mass% or less, 85 mass% or less is still more preferable, 80 mass% or less is especially preferable. By being in these ranges, it tends to form a film, and tends to have a high alignment regulating force for anisotropic dyes and the like. In addition, when 2 or more types of partial structures (3) are contained in the alignment film of this invention, it is preferable that the total amount is the said range.
  • the alignment film of the present invention preferably has a benzene ring in addition to the partial structure represented by the formula (3) because the planarity and rigidity of the molecule tend to increase.
  • the partial structure is represented by the following formula (4).
  • ring Y 1 represents a heterocyclic ring which may have a substituent.
  • Ring Y 1 has the same meaning as ring Y 1 of the formula (3), and the preferred range is also the same.
  • the position at which the ring Y 1 and the benzene ring connected to or condensed with the ring Y 1 are connected to the structure in the other epoxy reaction product is not particularly limited. Among these, the linearity of the molecule is obtained when the partial structures (4) are connected so that the aspect ratio (molecular length uniaxial ratio) of the molecule including the partial structure represented by the formula (4) is increased. And the orientation function to the anisotropic dye film tends to be improved.
  • the connecting position with the molecule is preferably substituted with an element away from the condensation position of the ring Y 1 in formula (4) and the aromatic ring.
  • connection is connected at the ⁇ -position and / or ⁇ -position, ⁇ ′-position and / or ⁇ ′-position, ⁇ ′′ -position and / or ⁇ ′′ -position of the following formula (4) ′.
  • ⁇ -position and / or ⁇ -position ⁇ ′-position and / or ⁇ ′-position
  • ⁇ ′′ -position / or ⁇ ′′ -position of the following formula (4) ′.
  • the rings included in Formula (4) may each independently have a substituent.
  • substituents examples include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, a hetero atom, a nitro group, a hydroxyl group, a halogen atom, and —C ( ⁇ O ) -Group and the like.
  • the proportion of the partial structure represented by the formula (4) present in the epoxy resin cured alignment film is not particularly limited, but is preferably 0.5% by mass or more, preferably 1% by mass or more, and more preferably 5% by mass or more.
  • the content is more preferably 10% by mass or more, and particularly preferably 20% by mass or more.
  • the alignment film of this invention contains 2 or more types of partial structures (4), it is preferable that the total amount is the said range.
  • the alignment film of the present invention includes an epoxy reactant, and the epoxy reactant includes a partial structure represented by the following formula (5).
  • the epoxy reactant includes a partial structure represented by the following formula (5).
  • the planarity and rigidity of the molecule increase, and the ⁇ - ⁇ interaction becomes stronger.
  • a charge polarization structure is formed in the molecule, and aggregation or association occurs between molecules or within the molecule due to hydrogen bonding or donor-acceptor interaction, which facilitates the arrangement of the molecules.
  • ring Y 2 and ring Y 3 each independently represent an optionally substituted heterocyclic ring.
  • R 2 represents a direct bond or an arbitrary divalent group.
  • Ring Y 2 and ring Y 3 are each independently synonymous with ring Y 1 of formula (3), and the preferred range is also the same. Of these, ring Y 2 and ring Y 3 are preferably the same. By ring Y 2 and ring Y 3 are the same, manufacturing is facilitated and also, easily met since size and structure are the same during the association between the molecules is the same, further, the R 2 The electron density on both sides is the same, and the arrangement and association of molecules tend to be easier.
  • the position at which ring Y 2 and ring Y 3 are connected to the structure in the other epoxy reactant is not particularly limited. Further, the position at which R 3 is connected to the benzene ring is not particularly limited.
  • the linearity of the molecule is obtained when the partial structure (5) is connected so that the aspect ratio (molecular length uniaxial ratio) of the molecule including the partial structure represented by the formula (5) is large.
  • the orientation function to the anisotropic dye film tends to be improved.
  • the connecting position with the molecule is preferably substituted with an element away from the condensed position of ring Y 2 and / or ring Y 2 of formula (5) and the aromatic ring.
  • substituents examples include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, a hetero atom, a nitro group, a hydroxyl group, a halogen atom, and —C ( ⁇ O ) -Group and the like.
  • R 2 represents a direct bond or any divalent group. Although it does not specifically limit as arbitrary bivalent group, C1-C8 alkylene group, C1-C8 alkenylene group, Carbon atom, Oxygen atom, Sulfur atom, Divalent amino group, Ester bond Etc. Moreover, said group may have a substituent, for example, a hetero atom, a C1-C5 alkyl group, a C1-C5 alkenyl group, an amino group, etc. are mentioned. Among these, since it becomes easy to form an anisotropic ordered structure in the alignment film, and the alignment regulating force to the composition for anisotropic dye film and the like can be increased, it must have a hetero atom.
  • it has an unsaturated bond.
  • —O—C ( ⁇ O) — —NH—C ( ⁇ O) —, —O—C ( ⁇ O) —, —C ( ⁇ O) —, —C ⁇ C—C ( ⁇ O) —, — (O ⁇ ) S ( ⁇ O) —, —O— and the like.
  • the proportion of the partial structure represented by the formula (5) in the epoxy resin cured alignment film is not particularly limited, but is preferably 0.5% by mass or more, more preferably 1% by mass or more, and further more preferably 5% by mass or more. Preferably, it is more preferably 10% by mass or more, and particularly preferably 20% by mass or more. Moreover, it is preferable that it is 99 mass% or less, It is more preferable that it is 90 mass% or less, 80 mass% or less is still more preferable, 60 mass% or less is especially preferable. By being in these ranges, it tends to have a high orientation regulating force for anisotropic dyes and the like. In addition, when 2 or more types of partial structures (5) are contained in the alignment film of this invention, it is preferable that the total amount is the said range.
  • the effect of the present invention tends to be obtained particularly when it is contained in an epoxy resin (reacted by an epoxy monomer having an epoxy group and / or an epoxy oligomer) in an epoxy resin cured alignment film. Therefore, it is preferable.
  • the amount of the epoxy resin in the epoxy cured alignment film is not particularly limited, but is preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 5% by mass or more, and more preferably 10% by mass or more. More preferably, it is particularly preferably 20% by mass or more. Moreover, an upper limit is not specifically limited, 100 mass% may be sufficient.
  • the epoxy resin cured alignment film of the present invention may contain other components in addition to the partial structure as long as the effects of the present invention are not significantly impaired. Examples include fillers, curing agents, surfactants, curing accelerators, and components derived therefrom. Specifically, the other component of the composition for alignment films mentioned later is mentioned.
  • the method for obtaining the epoxy resin cured alignment film of the present invention is not particularly limited.
  • the partial structures represented by the partial structure (P1), the partial structure (P2), the formula (2), the formula (3), the formula (4), and the formula (5) are aligned to form an epoxy resin cured alignment film.
  • the compound and / or reaction mixture contained in the film composition has.
  • the partial structure may be contained in an epoxy monomer having an epoxy group, an oligomer having an epoxy group, a phenoxy resin, a curing agent, an additive, or the like. Specifically, it will be described in the composition for alignment film described later.
  • the composition for an alignment film of the present invention is used when forming an alignment film that gives an alignment function to an anisotropic dye film or the like formed by a wet film formation method described later.
  • the composition for alignment films has a specific mass of at least one of the partial structure (P1) and the partial structure (P3) (hereinafter, sometimes referred to as “molecularly-oriented partial structure” or “partial structure (P)”). % Or more and a compound having an epoxy group and / or a functional group (R) may be included.
  • the partial structure (P1), the partial structure (P3), the epoxy group, and the functional group (R) only need to be included in the compound contained in the alignment film composition.
  • the combination of the partial structures and the like possessed by the compound is not particularly limited.
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P3) is represented by the following formula (6).
  • R 3 represents a divalent group containing a hetero atom and having an unsaturated bond, and the ring bonded to R 3 is a single ring.
  • R 3 in the formula (6) has the same meaning as R 1 in the formula (1). Further, the ring bonded to R 3 is also synonymous with the formula (1).
  • the composition for alignment film of the present invention is cured as a transparent and uniform film having no precipitate, and has sufficient mechanical properties, solvent resistance, and orientation regulating ability to the composition for anisotropic dye film
  • a compound having a partial structure (P) and an epoxy group hereinafter referred to as “compound A” or “compound E”
  • compound A a compound having a partial structure (P) and a functional group (R)
  • compound B a compound B or “compound F”
  • These compounds may be used alone or in combination.
  • these compounds or reaction mixtures may be used in combination with the above compounds A, B and the like.
  • a compound having a partial structure (P), a compound having an epoxy group hereinafter referred to as “compound C” or “compound G” having an epoxy group and not having a partial structure (P) and a functional group (R)).
  • a compound having a functional group (R) may be used in combination, or a compound having a partial structure (P) may be used in combination with the above compound A and compound B.
  • the compound having the partial structure (P) may be used in combination with the above compound A and compound C.
  • the content of the partial structure (P1) and / or the partial structure (P3) in the alignment film composition in the present invention is 0.5% by mass or more with respect to the entire alignment film composition excluding the solvent. It is preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and particularly preferably 20% by mass or more. Moreover, it is preferable that it is 99 mass% or less, It is more preferable that it is 90 mass% or less, 85 mass% or less is still more preferable, 80 mass% or less is especially preferable. By being in these ranges, the solubility in a solvent or the like is improved, and there is a tendency to impart a high alignment regulating force to the alignment film obtained by curing the alignment film composition. In addition, when 2 or more types of partial structure (P1) and / or partial structure (P3) are contained in the composition for alignment films of this invention, it is preferable that the total amount is the said range.
  • the epoxy group represents a structure generally called an oxirane ring.
  • the position and valence at which the oxirane ring is linked are not particularly limited.
  • the oxirane ring may have a substituent.
  • the epoxy group contained in the alignment film composition of the present invention reacts, and the compound is cured by increasing its molecular weight. By curing, it is possible to form an alignment film that gives alignment regulating force to the anisotropic dye film composition.
  • an epoxy group reacts to open a ring and becomes a flexible fatty chain structure.
  • the alignment film of the present invention can easily orient the composition for anisotropic dye film as compared with the existing alignment film for liquid crystal.
  • generated by an epoxy group reacting may acquire the effect which improves adhesiveness with a board
  • this hydroxyl group has low reactivity, it may react with an epoxy group depending on conditions, and may be used to control the mechanical strength of the film.
  • the hydroxyl group produced by the reaction of the epoxy group may sometimes have the effect of forming a film with good affinity when applying the anisotropic dye film composition in the wet film forming method described later.
  • the epoxy group in the alignment film composition in the present invention is preferably 0.1 mmol / g or more, more preferably 0.3 mmol / g or more, and more preferably 1.0 mmol / g with respect to the entire alignment film composition excluding the solvent. g or more is more preferable. Further, it is preferably 20 mmol / g or less, and more preferably 15 mmol / g or less.
  • the content of the epoxy group in the alignment film composition excluding the solvent is, for example, 44 g / mol for the oxirane group, and in the case of 0.1 mmol / g or more, 0.44% by mass or more. This is a preferred range. By being in these ranges, there is a tendency that effects of surface treatment such as mechanical strength and rubbing, which are particularly suitable for use as an alignment film for an anisotropic dye film, can be obtained.
  • Examples of the partial structure containing an epoxy group include a partial structure represented by the following formula (14).
  • X 1 to X 4 represents a direct bond or an alkylene group having 1 to 6 carbon atoms, and is bonded to another partial structure through these.
  • X 1 to X 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a direct bond, or an alkylene group having 1 to 6 carbon atoms.
  • the alkylene group having 1 to 6 carbon atoms has 6 or less, more preferably 4 or less, and particularly preferably 3 or less.
  • the alkyl group having 1 to 6 carbon atoms and the alkylene group having 1 to 6 carbon atoms may be linear or branched.
  • X 1 to X 4 may be the same or different, and they may form a ring structure in any position and / or combination. The specific example of the partial structure containing an epoxy group is shown below.
  • a structure in which a methylene group is bonded to this epoxy group is generally referred to as a glycidyl group.
  • the partial structure containing an epoxy group bonded to another partial structure via at least one of X 1 to X 4 include those represented by the following structural formula. Examples include those directly bonded, glycidyl group, glycidyl ether group, glycidyl amino group, glycidyl ester group, glycidyl amide group, glycidyl sulfonamide group, cyclohexene oxide group and the like.
  • a glycidyl ether group, a glycidyl amino group, a glycidyl sulfonamide group or a glycidyl ester group is more preferred from the viewpoint of good reactivity and ease of synthesis.
  • the functional group that reacts with an epoxy group represents a structure involved in the curing reaction of the epoxy group.
  • the functional group which the compound generally called an epoxy hardening agent has is illustrated. Specific examples include a phenolic hydroxyl group, a primary amino group, a thiol group, a carboxyl group, a cyanate group, and an isocyanate group.
  • phenolic hydroxyl groups, primary amino groups, thiol groups, and carboxyl groups are preferred from the viewpoint of obtaining raw materials, and phenolic hydroxyl groups and primary amino groups are more preferred from the viewpoint of stability of the compound and ease of synthesis. .
  • the functional group (R) in the composition for alignment film in the present invention has the effect of surface treatment such as mechanical strength and rubbing suitable for using the composition for alignment film as an alignment film for anisotropic dye film.
  • 0.1 mmol / g or more is preferable with respect to the whole composition for alignment films except a solvent, 0.3 mmol / g or more is more preferable, 1.0 mmol / g or more is still more preferable. Further, it is preferably 20 mmol / g or less, and more preferably 15 mmol / g or less.
  • content of the reactive group (R) which reacts with the epoxy group in the alignment film composition excluding the solvent for example, since the amino group is 14 g / mol, in the case of 0.1 mmol / g or more, 0.14% by mass or more is a preferable range.
  • a compound having a partial structure (P1) and / or a partial structure (P3) and an epoxy group is referred to as “compound A”.
  • the partial structure (P) forms an anisotropic regular structure, and the compound A can have an association site or an arrangement site.
  • an alignment film having an association site or an array site can be formed by reacting an epoxy group.
  • an epoxy group reacts and opens a ring, it becomes a flexible fatty chain structure. Therefore, it becomes easy to form an anisotropic ordered structure with increased regularity of the partial structure (P) during reaction of the alignment film or surface treatment such as rubbing, and it is possible to increase the regularity of the obtained alignment film.
  • the number of partial structures (P1) and / or partial structures (P3) contained in one molecule of compound A may be one or more. In a plurality of cases, the partial structure (P1) and / or the partial structure (P3) may be the same or different. Among these, it is preferable to have two or more partial structures (P) in one molecule of compound A because an anisotropic ordered structure of the partial structure (P) can be easily formed. There is no particular upper limit in one molecule of compound A of partial structure (P), but it is preferably 5 or less for reasons of ease of synthesis. When the number of partial structures (P) contained in one molecule of compound A is plural, it is more preferable to have both the partial structure (P1) and the partial structure (P3).
  • the compound A contained in the alignment film composition of the present invention may be one type, but may be a combination of a plurality of different types.
  • a compound having a partial structure (P1) hereinafter referred to as AI
  • a compound having a partial structure (P3) hereinafter referred to as A-II
  • A-II may be contained in any abundance ratio. Good. There is no limitation on their combinations and abundance ratios.
  • Compound A may have one epoxy group in one molecule of compound A or a plurality of epoxy groups. Those having a plurality of epoxy groups are preferred because they tend to form a network structure and tend to increase the strength of the alignment film.
  • the number of epoxy groups in one molecule is preferably 6 or less, more preferably 4 or less, and still more preferably 2 or less. By being in these ranges, the network does not become too dense, and the formation of the anisotropic ordered structure of the partial structure (P) tends not to be hindered. Further, the curing reaction proceeds sufficiently, and the thermal stability of the obtained alignment film tends to be improved. Therefore, the anisotropic regular structure of the partial structure (P) tends to be efficiently formed while increasing the strength of the alignment film and improving the film formability.
  • the epoxy group in the present invention is preferably located at the end of the molecule of the compound A because the anisotropic ordered structure of the partial structure (P) tends to be easily formed.
  • the bonding position of the epoxy group and the partial structure (P) in Compound A is not particularly limited, and may be bonded at an arbitrary position and number.
  • the bonding form between the epoxy group and the molecularly oriented partial structure (P) in the compound A may be directly bonded or may be bonded through an arbitrary group. Examples of the case where an arbitrary group is interposed include an example in which the partial structure (P) is bonded to the combination of the epoxy group and the arbitrary group mentioned in the partial structure including the epoxy group.
  • the weight average molecular weight (Mw) of Compound A is usually 200 or more, preferably 250 or more. Moreover, it is 100,000 or less normally, Preferably it is 50,000 or less. This range is preferable because the composition for an alignment film of the present invention is cured as an alignment film and has sufficient mechanical properties. Moreover, epoxy equivalent is 100 or more and 20000 or less normally, Preferably it is 10,000 or less, More preferably, it is 7000 or less. This range is preferable because the composition for an alignment film of the present invention is cured as an alignment film and has sufficient mechanical properties.
  • the melting point of Compound A is usually 350 ° C. or lower, preferably 300 ° C. or lower. By being in these ranges, the composition for an alignment film of the present invention is cured as a transparent and uniform alignment film without precipitates at a low temperature, and tends to have sufficient mechanical properties and solvent resistance.
  • the compound A is dissolved or dispersed usually 3% by mass or more, preferably 4% by mass or more in a solvent that is usually used. By being in these ranges, it becomes possible to apply the compound A in a state of being dissolved or dispersed in a solvent. In particular, when it is applied in a dissolved state, a transparent and uniform alignment film is easily obtained, which is preferable.
  • a solvent the solvent mentioned later is mentioned as a solvent which the composition for alignment films may contain, for example.
  • Examples of the compound A of the present invention include the following compound groups A1 to A21 and A24 to A33 having a glycidyl ether group.
  • A1 to A11 are preferable from the viewpoint of rigidity, aggregation, and association of the compound A structure
  • A12 to A21 are preferable from the viewpoint of charge bias.
  • A24 to A33 are more preferable because they have both.
  • l 1 to l 33 , m 1 to m 33 , o 18 and o 20 each independently represent an integer of 1 or 2, and they may be the same or different. Also good.
  • l + m for example, the compound A1 is l 1 + m 1
  • l + m + o for example, Compound A18 has l 18 + m 18 + o 18
  • n 6 , n 7 , n 9 and n 11 are each independently an integer of 2 or more and 12 or less.
  • the compound B of the present invention is a compound having a functional group (R) and a partial structure (P1) and / or a partial structure (P3). Since compound B has the same partial structure (P) as that exemplified for compound A, as in the case of compound A, it is easy to form an association site or a sequence site of partial structure (P). On the other hand, since compound B has a functional group (R), it can form an alignment film in combination with compound C described later. That is, the compound B can form a regular structure of molecular orientation in the present invention, and at the same time, can act as a curing agent for the compound C to form an alignment film having sufficient strength.
  • the partial structure (P) is more agglomerated during the surface treatment such as rubbing or the like of the alignment film, increases the associative property, and tends to form a regular structure. It is possible to increase the orientation regulating force of the.
  • the molecular weight of the compound B is large, it is possible to form an alignment film using only the compound B.
  • the alignment film obtained using Compound B has regularity similar to that obtained by curing Compound A, and an anisotropic dye film composition to be described later is used as an existing alignment film for liquid crystals. It becomes possible to orient more easily than the above.
  • the alignment film composition often has an aromatic ring or a heteroatom, and thus has a bias in charge.
  • the epoxy group when the epoxy group is in the alignment film composition, the epoxy group reacts to generate a hydroxyl group. Therefore, in the wet film forming method described later, an anisotropic dye having an aromatic ring described later is used. It is excellent in interaction and can be formed with good affinity even when the composition for anisotropic dye film is applied.
  • the number of partial structures (P) contained in one molecule of compound B in the composition for alignment films of the present invention may be one or more. In the case of a plurality, the partial structures (P) may be the same or different. Among these, it is preferable to have two or more partial structures (P) because an anisotropic ordered structure is easily formed.
  • the upper limit of the number of partial structures (P) is not particularly limited, but is preferably 5 or less for reasons of ease of synthesis.
  • the compound B contained in the composition for alignment films of the present invention may be one type, but may be a combination of a plurality of different types.
  • a compound having a partial structure (P1) hereinafter referred to as Compound BI
  • a compound having a partial structure (P3) hereinafter referred to as Compound B-II
  • the compound B may have one or more functional groups (R) per molecule of the compound B.
  • the number of functional groups (R) in one molecule is preferably 6 or less, more preferably 4 or less, and still more preferably 2 or less.
  • a network structure having a plurality of functional groups (R) tends to form a network structure and tends to increase the strength of the alignment film and improve the film formability.
  • the network is not too dense, and it becomes easier to form an anisotropic regular structure with increased regularity of the partial structure (P) in curing the alignment film or in surface treatment such as rubbing. It is possible to increase the regularity.
  • the epoxy group in the present invention is preferably located at the end of the molecule of the compound B because the anisotropic regular structure of the partial structure (P) tends to be easily formed. .
  • the bonding position of the functional group (R) and the partial structure (P) in the compound B of the present invention is not particularly limited, and the functional group (R) and the partial structure (P) may be directly bonded to each other. It may be bonded via the group.
  • the optional group include alkylene groups having 1 to 10 carbon atoms, alkyleneamino groups having 1 to 10 carbon atoms, alkyleneoxy groups having 1 to 10 carbon atoms, arylarylene groups having 6 to 12 carbon atoms, carbon Examples of the alkenylene group, the ketone group, the sulfonyl group, the ester group, the amide group, the sulfonyl ester group, and the sulfonamide group represented by Formulas 2 to 10 can be freely selected according to the compound structure and purpose.
  • the structure of the alkylene group having 1 to 10 carbon atoms, the alkyleneamino group having 1 to 10 carbon atoms, and the alkyleneoxy group having 1 to 10 carbon atoms is not particularly limited, and may be any of linear, branched, or cyclic structures. Also good. Among these, an alkylene group having 2 to 10 carbon atoms, an alkyleneamino group having 1 to 10 carbon atoms, an alkyleneoxy group having 1 to 10 carbon atoms, and a sulfonamide group are preferable from the viewpoint of ease of synthesis and availability of raw materials. .
  • the alkylene group having 2 to 10 carbon atoms, the alkyleneamino group having 1 to 10 carbon atoms, the alkyleneoxy group having 1 to 10 carbon atoms, the aryl group, and the alkenylene group may have a substituent.
  • the substituent that may have include an alkyl group having 1 to 10 carbon atoms, a halogen group, and an aryl group.
  • a direct bond, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aryl group is easy to synthesize, availability of raw materials, epoxy group It is preferable for reasons such as reactivity with.
  • Compound B has a weight average molecular weight (Mw) of usually 200 or more, preferably 250 or more, and usually 100,000 or less, preferably 50,000 or less. By being in this range, the composition for an alignment film of the present invention is cured as a film and tends to have sufficient mechanical properties.
  • Mw weight average molecular weight
  • the melting point (or softening point) of Compound B is usually 350 ° C. or lower, preferably 300 ° C. or lower. By being in this range, the composition for alignment film of the present invention is cured at a low temperature as a transparent and uniform alignment film without precipitates, and tends to have sufficient mechanical properties and solvent resistance.
  • Compound B is preferably dissolved or dispersed in a commonly used solvent in an amount of usually 3% by mass or more, preferably 4% by mass or more. By being in these ranges, it becomes possible to apply the compound B in a state dissolved or dispersed in a solvent. In particular, when it is applied in a dissolved state, a transparent and uniform alignment film is easily obtained, which is preferable.
  • the solvent which is usually used is the same as the solvent mentioned in Compound A.
  • Examples of the compound B of the present invention include the following compound groups B1 to B20 and B23 to B32.
  • R 1 to R 32 in the compounds B1 to B20 and B23 to B32 represent the functional group (R) possessed by the compound B.
  • B1 to B11 are preferable from the viewpoints of rigidity, aggregation, and association of the compound B structure
  • B12 to B20 are preferable from the viewpoint of charge bias.
  • B23 to B32 are more preferable because they have both.
  • e 1 to e 32 and f 1 to f 32 each independently represent an integer of 1 or 2, and may be the same or different.
  • e + f for example, compound B1 is e 1 + f 1
  • the compounds B17, the compound B18 and Compound B20, e + f + h e.g., Compound A17 is e 17 + f 17 + h 17
  • g 6 , g 7 , g 9 and g 11 are each independently an integer of 2 or more and 12 or less.
  • a commercially available product may be used as the compound B of the present invention.
  • polyamideimide resin having a carboxyl group as a functional group (R) (DIC Corporation, UNIDIC V-8000 series), or phenolimide having an aromatic hydroxy group as R (Gunei Chemical Industry Co., Ltd., phenolimide GPI series) Etc.
  • R functional group
  • phenolimide having an aromatic hydroxy group as R (Gunei Chemical Industry Co., Ltd., phenolimide GPI series) Etc.
  • Compound C is a compound having an epoxy group and does not have a partial structure (P1), a partial structure (P3), and a functional group (R).
  • the compound C is not particularly limited, but preferably has at least two epoxy groups in one molecule of the compound C.
  • glycidyl ethers such as bisphenol A, bisphenol F, naphthalene diol, phenol novolac resins, cresol novolac resins, and phenol aralkyl resins; diglycidyl ethers such as biphenol and alkyl-substituted biphenols; triglycidyl ethers such as triphenolmethane; Examples thereof include tetraglycidyldiaminodiphenylmethane; triglycidylaminophenol; various epoxy compounds such as dicyclopentadiene type epoxy resin.
  • the alignment film compositions of cases (1) to (3) containing at least one of the compounds A to C are represented as follows.
  • the alignment film composition of the present invention is an alignment film composition comprising at least one of the compound group I and the compound group II, wherein the partial structure (P1) and the partial structure in the alignment film composition excluding the solvent
  • the ratio of at least one of the structures (P3) is 0.5% by mass or more.
  • the compound group I is a compound A having an epoxy group and at least one of the partial structure (P1) and the partial structure (P3)
  • Compound Group II is a functional group that reacts with an epoxy group
  • a compound B having at least one of a partial structure (P1) and a partial structure (P3)
  • a compound C having an epoxy group
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P3) is represented by the following formula (6).
  • R 3 represents a divalent group containing a hetero atom and having an unsaturated bond, and the ring bonded to R 3 is a single ring.
  • R 3 has the same meaning as R 1 in the formula (1). Further, the ring bonded to R 3 is also synonymous with the formula (1).
  • the alignment film obtained is cured as a transparent and uniform film without precipitates, and sufficient mechanical properties, solvent resistance and anisotropy are obtained. It can have an orientation regulating force on the composition for a dye film.
  • Compound A, compound B, and compound C are as described above.
  • the charge ratio (B / C) between the compound B and the compound C is large in that the epoxy group contained in the compound C hardly remains unreacted and can be sufficiently cured in a short time. Is preferred.
  • the functional group (R) of the compound B is small in that it is difficult to remain unreacted in the alignment film obtained by curing the alignment film composition of the present invention.
  • the equivalent ratio of the functional group (R) of the compound B to the epoxy group contained in the compound C of the present invention is preferably 0.8 or more, and 0.9 or more. More preferably, it is used.
  • the total amount of the respective equivalents is preferably within the above range.
  • the charging ratio (A / B) between compound A and compound B is small in that the epoxy group contained in compound A hardly remains unreacted and can be sufficiently cured in a short time. Is preferred.
  • the functional group (R) of the compound B is not unreacted and remains in the alignment film obtained by curing the alignment film composition of the present invention.
  • the equivalent ratio of the functional group (R) of the compound B to the epoxy group contained in the compound A of the present invention is preferably 0.8 or more, and 0.9 or more. More preferably, it is used. Moreover, it is preferable to use it so that it may become 1.5 or less, and it is still more preferable to use it so that it may become 1.2 or less.
  • the total amount of each equivalent is in the above range.
  • the reaction mixture D means other components (curing agent, solvent, other additives, etc.) to be described later in each of the case (1), case (2) and case (3) in the alignment film composition. It shows the reaction mixture obtained by the composition for alignment film obtained by mixing the above-mentioned by the method for producing the composition for alignment film described later (treatment by (a) phenoxy resinification, (b) oligomerization, etc.). That is, the reaction mixture D is obtained by reacting the alignment film composition of the present invention. Like the reaction mixture D, when the partial structure (P) is partially reacted in advance with another structure, group, etc., the melting point tends to be lowered or eliminated. Thereby, it may be possible to obtain the effects of suppressing crystal precipitation during the formation of the alignment film, lowering the curing temperature, and improving the film formability.
  • the reaction mixture D in case (4) represents a mixture obtained by combining the above compounds using the methods (a) and (b) below.
  • a method using phenoxylation in which a bifunctional epoxy compound is heated together with an addition type curing agent to induce a soluble linear resin (generally called a polymer type epoxy resin or a phenoxy resin).
  • the equivalent ratio of the functional group (R) to the epoxy group (epoxy group / functional group (R)) in the entire alignment film composition is such that the epoxy group hardly remains unreacted. A larger amount is preferable in that it can be cured sufficiently in a short time.
  • the functional group (R) of the compound B is less unreacted in the alignment film obtained by curing the alignment film composition of the present invention. Specifically, it is preferably used so as to be 0.8 or more, and more preferably used so as to be 0.9 or more. Moreover, it is preferable to use it so that it may become 1.5 or less, and it is still more preferable to use it so that it may become 1.2 or less.
  • FIG. 1 An alignment film composition comprising a reaction mixture having at least one of a partial structure (P1) and a partial structure (P4), In the alignment film composition excluding the solvent, the ratio of at least one of the partial structure (P1) and the partial structure (P4) is 0.5% by mass or more.
  • the partial structure (P1) is an aromatic ring containing a hetero atom
  • the partial structure (P4) is represented by the following formula (7).
  • R 4 represents a divalent group containing a hetero atom and having an unsaturated bond.
  • R 4 has the same meaning as R 1 in Formula (1).
  • the two benzene rings to which R 4 is bonded may be a single ring or may be condensed. Moreover, you may have a substituent each independently.
  • the substituent that the two benzene rings to which R 4 is bonded may have, but is not particularly limited to, for example, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, A hetero atom, a nitro group, a hydroxyl group, a halogen atom, a —C ( ⁇ O) — group and the like can be mentioned.
  • the content of the partial structure (P1) and / or the partial structure (P4) in the alignment film composition in the present invention is 0.5% by mass or more with respect to the entire alignment film composition excluding the solvent. It is preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and particularly preferably 20% by mass or more. Moreover, it is preferable that it is 99 mass% or less, It is more preferable that it is 90 mass% or less, 85 mass% or less is still more preferable, 80 mass% or less is especially preferable. By being in these ranges, the solubility in a solvent or the like is improved, and there is a tendency to impart a high alignment regulating force to the alignment film obtained by curing the alignment film composition. In addition, when 2 or more types of partial structure (P1) and / or partial structure (P4) are contained in the composition for alignment films of this invention, it is preferable that the total amount is the said range.
  • Compound E is a compound having an epoxy group and a partial structure represented by Formula (8).
  • ring Y 4 represents a heterocyclic ring which may have a substituent.
  • the partial structure represented by the formula (8) forms an anisotropic ordered structure, and the compound E can have an association site or a sequence site. Furthermore, an alignment film having an association site or an array site can be formed by reacting an epoxy group. Moreover, when an epoxy group reacts and opens a ring, it becomes a flexible fatty chain structure. Therefore, it becomes easier to form an anisotropic ordered structure in which the regularity of the partial structure represented by the formula (8) is increased during reaction of the alignment film or surface treatment such as rubbing. It can be increased.
  • the ring Y 4 in the formula (8) has the same meaning as the ring Y 1 in the formula (3), and the preferred range and the preferred reason are the same.
  • the position at which the ring Y 4 and the benzene ring condensed with the ring Y 4 are connected to the structure in the other epoxy reactant is not particularly limited, and the aspect ratio of the molecule containing the partial structure represented by the formula (8) It is preferable that the partial structures are connected so that the (molecular length uniaxial ratio) is large because molecular linearity is obtained and the orientation function to the anisotropic dye film tends to be improved. As one aspect, there may be mentioned those represented by formula (3).
  • the benzene ring condensed with the ring Y 4 and the ring Y 4 may have a substituent.
  • substituents include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, a hetero atom, a nitro group, a hydroxyl group, a halogen atom, and —C ( ⁇ O ) -Group and the like.
  • the number of partial structures represented by formula (8) contained in one molecule of compound E may be one or more. In the case of a plurality, the partial structures represented by the formula (8) may be the same or different. Among these, having two or more partial structures represented by the formula (8) in one molecule of the compound E facilitates the formation of an anisotropic ordered structure of the partial structure represented by the formula (8). Therefore, it is preferable. Moreover, there is no particular upper limit in one molecule of the compound E having the partial structure represented by the formula (8), but it is preferably 5 or less for reasons of ease of synthesis.
  • Compound E may have one or more epoxy groups in one molecule of compound E. Those having a plurality of epoxy groups are preferred because they tend to form a network structure and tend to increase the strength of the alignment film.
  • the number of epoxy groups in one molecule is preferably 6 or less, more preferably 4 or less, and still more preferably 2 or less. By being in these ranges, the network does not become too dense, and tends to prevent the formation of the anisotropic ordered structure of the partial structure represented by the formula (8). Further, the curing reaction proceeds sufficiently, and the thermal stability of the obtained alignment film tends to be improved. Therefore, there is a tendency that the anisotropic regular structure of the partial structure represented by the formula (8) can be efficiently formed while increasing the strength of the alignment film and improving the film formability.
  • the epoxy group in the present invention is preferably located at the end of the molecule of the compound E because it tends to facilitate formation of an anisotropic ordered structure having a partial structure represented by the formula (8).
  • the bonding position or the like of the epoxy group in compound E and the partial structure represented by the formula (8) is not particularly limited, and may be bonded at an arbitrary position and number.
  • the bonding form between the epoxy group in compound E and the partial structure represented by formula (8) may be directly bonded or may be bonded via any group. Examples of the case where an arbitrary group is interposed include an example in which the partial structure represented by the formula (8) is bonded to the combination of the epoxy group and the arbitrary group mentioned in the partial structure including the epoxy group. .
  • the weight average molecular weight (Mw) of compound E is usually 200 or more, preferably 250 or more. Moreover, it is 100,000 or less normally, Preferably it is 50,000 or less. This range is preferable because the composition for an alignment film of the present invention is cured as an alignment film and has sufficient mechanical properties. Moreover, epoxy equivalent is 100 or more and 20000 or less normally, Preferably it is 10,000 or less, More preferably, it is 7000 or less. This range is preferable because the composition for an alignment film of the present invention is cured as an alignment film and has sufficient mechanical properties.
  • the melting point of Compound E is usually 350 ° C. or lower, preferably 300 ° C. or lower. By being in these ranges, the composition for an alignment film of the present invention is cured as a transparent and uniform alignment film without precipitates at a low temperature, and tends to have sufficient mechanical properties and solvent resistance.
  • Compound E is preferably dissolved or dispersed in a commonly used solvent in an amount of usually 3% by mass or more, preferably 4% by mass or more. By being in these ranges, it becomes possible to apply the compound E in a state dissolved or dispersed in a solvent. In particular, when it is applied in a dissolved state, a transparent and uniform alignment film is easily obtained, which is preferable.
  • a solvent the solvent mentioned later is mentioned as a solvent which the composition for alignment films may contain, for example.
  • Compound F is a compound having a functional group (R) that reacts with an epoxy group and a partial structure represented by Formula (8). Since compound F has the same partial structure represented by formula (8) as exemplified in reaction mixture D, as in the case of compound E, the association site and sequence of the partial structure represented by formula (8) It is easy to form a part. On the other hand, since compound F has a functional group (R), it can form an alignment film in combination with compound G described later. That is, the compound F can form a regular structure of molecular orientation in the present invention, and at the same time, can act as a curing agent for the compound F to form an alignment film having sufficient strength.
  • the alignment film obtained by using the compound F has regularity like that obtained by curing the compound E, and the composition for anisotropic dye film described later is used as an existing alignment film for liquid crystal. It becomes possible to orient more easily than the above.
  • the alignment film composition often has an aromatic ring or a hetero atom, and thus has a bias in charge.
  • the epoxy group when the epoxy group is in the alignment film composition, the epoxy group reacts to generate a hydroxyl group. Therefore, in the wet film forming method described later, an anisotropic dye having an aromatic ring described later is used. It is excellent in interaction and can be formed with good affinity even when the composition for anisotropic dye film is applied.
  • the number of partial structures represented by the formula (8) contained in one molecule of compound F in the composition for alignment films of the present invention may be one or plural. In the case of a plurality, the partial structures represented by the formula (8) may be the same or different. Among these, it is preferable to have two or more partial structures represented by Formula (8) because an anisotropic ordered structure can be easily formed.
  • the upper limit of the number of partial structures (P) is not particularly limited, but is preferably 5 or less for reasons of ease of synthesis.
  • the compound F contained in the composition for alignment films of the present invention may be one kind, it may be a combination of a plurality of different kinds.
  • the compound F may have one or more functional groups (R) per molecule of the compound F.
  • the number of functional groups (R) in one molecule is preferably 6 or less, more preferably 4 or less, and still more preferably 2 or less.
  • a network structure having a plurality of functional groups (R) tends to form a network structure and tends to increase the strength of the alignment film and improve the film formability.
  • the network is not too dense, and it becomes easier to form an anisotropic regular structure in which the regularity of the partial structure represented by the formula (8) is increased in the surface treatment such as the rubbing or the curing of the alignment film, It becomes possible to increase the regularity of the obtained alignment film.
  • the epoxy group in the present invention is preferably located at the end of the molecule of the compound F because it tends to facilitate formation of an anisotropic ordered structure having a partial structure represented by the formula (8).
  • the bonding position of the functional group (R) and the partial structure represented by the formula (8) in the compound F of the present invention is not particularly limited, and the partial structure represented by the functional group (R) and the formula (8). May be directly bonded, or may be bonded via any group. As an arbitrary group, the group quoted by the compound E is mentioned, A preferable group is also the same.
  • the melting point (or softening point) of Compound F is usually 350 ° C. or lower, preferably 300 ° C. or lower. By being in this range, the composition for alignment film of the present invention is cured at a low temperature as a transparent and uniform alignment film without precipitates, and tends to have sufficient mechanical properties and solvent resistance.
  • Compound F is preferably dissolved or dispersed in a solvent that is usually used in an amount of usually 3% by mass or more, preferably 4% by mass or more. By being in these ranges, it becomes possible to apply the compound F in a state of being dissolved or dispersed in a solvent. In particular, when it is applied in a dissolved state, a transparent and uniform alignment film is easily obtained, which is preferable.
  • the solvent which is usually used is the same as the solvent mentioned in Compound A.
  • the formula (8) is independently linked to the benzene ring as represented by the following formula (9).
  • the partial structure represented by Formula (9) it tends to be easy to form an anisotropic ordered structure with increased regularity in the alignment film.
  • the ring Y 4 represents a heterocyclic ring which may have a substituent.
  • Ring Y 4 has the same meaning as ring Y 1 in formula (8), and the preferred range, substituents that may be present, the connecting position, and the like are also the same.
  • the rings included in Formula (9) may each independently have a substituent. Examples of the substituent that may be included include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an amino group, a hetero atom, a nitro group, a hydroxyl group, a halogen atom, and —C ( ⁇ O ) -Group and the like.
  • the formula (8) is independently linked as represented by the following formula (10).
  • the partial structure represented by the formula (10) it tends to be easy to form an anisotropic ordered structure with increased regularity in the alignment film.
  • ring Y 5 and ring Y 6 each independently represent an optionally substituted heterocyclic ring.
  • R 6 represents an arbitrary divalent group.
  • Ring Y 5 , Ring Y 6 and R 1 have the same meanings as Ring Y 2 , Ring Y 3 and R 2 in Formula (5), respectively, and preferred ranges, substituents that may be present, coupling positions, and the like are also synonymous. It is.
  • the compound G is a compound having an epoxy group and does not have the partial structure represented by the formula (8) and the functional group (R).
  • the compound G is not particularly limited, but preferably has at least two epoxy groups in one molecule of the compound F. Specific examples thereof include those exemplified as Compound C.
  • Compound G may be used alone or in combination of two or more in any ratio. Among these, from the viewpoint of the reactivity, uniformity and transparency of the entire alignment film composition, it is preferable to have a group or structure compatible with the partial structure represented by the formula (8), Specifically, it preferably has an aromatic ring.
  • the alignment film compositions of Case (5) to Case (7) containing at least one of the compounds E to G are represented as follows.
  • the alignment film composition of the present invention includes at least one of compound group III and compound group IV.
  • the composition for the alignment film contains at least one of the compound group III or the compound group IV
  • the resulting alignment film is cured as a transparent and uniform film without precipitates, and has sufficient mechanical properties, solvent resistance, and anisotropic properties. It has the ability to regulate the orientation of the composition for functional dye film.
  • compound group III is compound E having an epoxy group and a partial structure represented by the following formula (8)
  • compound group IV is represented by a functional group that reacts with the epoxy group and the following formula (8).
  • ring Y 4 represents a heterocyclic ring which may have a substituent.
  • the charge ratio (F / G) between the compound F and the compound G is large in that the epoxy group contained in the compound G hardly remains unreacted and can be sufficiently cured in a short time. Is preferred.
  • the functional group (R) of the compound F is small in that it is difficult to remain unreacted in the alignment film obtained by curing the alignment film composition of the present invention.
  • the equivalent ratio of the functional group (R) of the compound F to the epoxy group contained in the compound G of the present invention is preferably 0.8 or more, and 0.9 or more. More preferably, it is used.
  • the total amount of the respective equivalents is preferably within the above range.
  • the charge ratio (E / F) between compound E and compound F is small in that the epoxy group contained in compound E hardly remains unreacted and can be sufficiently cured in a short time. Is preferred.
  • the functional group (R) of the compound F is unreacted and hardly remains in the alignment film obtained by curing the alignment film composition of the present invention.
  • the equivalent ratio of the functional group (R) of the compound F to the epoxy group contained in the compound E of the present invention is preferably 0.8 or more, and 0.9 or more. More preferably, it is used. Moreover, it is preferable to use it so that it may become 1.5 or less, and it is still more preferable to use it so that it may become 1.2 or less.
  • the total amount of each equivalent is preferably in the above range. .
  • the weight average molecular weight of at least one compound or reaction mixture is preferably 200 or more, more preferably 250 or more. . Moreover, it is 200,000 or less normally, Preferably it is 100,000 or less, More preferably, it is 50,000 or less. By being in these ranges, it may have the effect of suppressing film repelling and film defects when the alignment film composition is applied, and improving film formability.
  • the alignment film composition of the present invention may contain a curing agent.
  • the curing agent that may be contained in the alignment film composition of the present invention may be any substance that contributes to the reaction of the epoxy group possessed by Compound A, Compound C, Compound E, Compound G, etc. Also included are those generally known as curing accelerators such as curing agents. Examples of the curing agent according to the present invention include the following three. 1) A substance that contributes to the reaction between epoxy groups of Compound A, Compound C, Compound E, or Compound G contained in the alignment film composition of the present invention.
  • curing agent there is no restriction
  • curing agent should just be performed according to balance, such as physical properties, such as hardening conditions, the shape of hardened
  • the curing agent include an addition polymerization type curing agent that contributes to a reaction between epoxy groups and a catalyst type curing agent that promotes an addition reaction between epoxy group-containing compounds.
  • phenolic curing agents such as aliphatic amines, polyether amines, alicyclic amines, aromatic amines, acid anhydride curing agents, amide curings.
  • Agents active ester curing agents, organic acid dihydrazides, mercaptan curing agents, isocyanate curing agents, blocked isocyanate curing agents, and the like.
  • the catalyst-type curing agent include imidazole and derivatives thereof, tertiary amines, organic phosphines, phosphonium salts, tetraphenylboron salts, and boron halide amine complexes.
  • an orientation film excellent in adhesiveness and bending strength tends to be easily obtained.
  • curing agent tends to obtain the composition for alignment films excellent in workability.
  • Primary and secondary amine curing agents are easy to obtain alignment films having excellent heat resistance, and acid anhydride curing agents are excellent in liquid curing processes.
  • an amorphous curing agent when used, it tends to be easy to obtain an alignment film excellent in workability and an alignment film excellent in bending strength. is there.
  • a crystalline curing agent when a crystalline curing agent is used, an orientation film excellent in heat resistance and mechanical properties tends to be obtained.
  • a catalyst-type curing agent By using a catalyst-type curing agent, it tends to be easy to obtain an alignment film having excellent heat resistance and chemical resistance. Since the curing temperature and the curing speed of the catalytic curing agent differ depending on the type, an appropriate curing condition may be selected depending on the process.
  • the catalyst type curing agents imidazole type is preferable.
  • 2-ethyl-4-methylimidazole tends to increase the curing rate and can be cured at low temperature and low cost.
  • 1-cyanoethyl-2-undecylimidazole tends to have a wide range of applicable types of epoxy group-containing compounds and alignment film shapes.
  • the curing agent used in the present invention is preferably an addition polymerization type curing agent because it easily obtains mechanical properties, solvent resistance, and orientation regulating power to the composition for anisotropic dye film.
  • a phenol type, an amine type, or an acid anhydride type is preferable, and an amine type or an acid anhydride type is particularly preferable.
  • the structure having high compatibility with the partial structure (P) is one in which the curing agent has an aromatic ring from the viewpoint of uniformity of the alignment film, transparency, reactivity, and the like.
  • the melting point is preferably not more than the curing temperature.
  • a substance (curing accelerator) that exhibits a function of promoting the addition reaction may be added.
  • a substance (curing accelerator) that exhibits a function of promoting the addition reaction include one or more selected from amines, phenols, imidazoles, and phosphonium salts.
  • a phosphonium salt system is preferable from the viewpoints of reactivity that can be cured at a low temperature and stability of the compound.
  • a curing accelerator When a curing accelerator is used, it is preferably used in an amount of 0.1 parts by weight or more, more preferably 0.2 parts by weight or more with respect to 100 parts by weight of the alignment film composition excluding the solvent. Is more preferable. Moreover, it is preferable to use it so that it may become 20 weight part or less, and it is still more preferable to use it so that it may become 10 weight part or less. By being in these ranges, there is a tendency that reactivity that can be cured even at a low temperature and stability of the compound can be obtained.
  • phenolic curing agents include bisphenol A, bisphenol F, 4,4'-dihydroxydiphenylmethane, 4,4'-dihydroxydiphenyl ether, 1,4-bis (4-hydroxyphenoxy) benzene, 1,3-bis (4-hydroxyphenoxy) benzene, 4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl ketone, 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl 10- (2,5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, phenol novolak, bisphenol A novolak, o-cresol novolak, m-cresol novolak, p-ke Zole novolak, xylenol novolak, poly-p-hydroxystyrene, hydroquinone, re
  • amine curing agent examples include aliphatic amines such as ethylenediamine, 1,3-diaminopropane, 1,4-diaminopropane, hexamethylenediamine, 2,5-dimethylhexamethylenediamine, trimethylhexamethylenediamine, Examples include diethylenetriamine, iminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-hydroxyethylethylenediamine, tetra (hydroxyethyl) ethylenediamine, and the like.
  • polyether amines examples include triethylene glycol diamine, tetraethylene glycol diamine, diethylene glycol bis (propylamine), polyoxypropylene diamine, polyoxypropylene triamines, and the like.
  • Cycloaliphatic amines include isophorone diamine, metacene diamine, N-aminoethylpiperazine, bis (4-amino-3-methyldicyclohexyl) methane, bis (aminomethyl) cyclohexane, 3,9-bis (3-amino). (Propyl) -2,4,8,10-tetraoxaspiro (5,5) undecane, norbornenediamine and the like.
  • Aromatic amines include tetrachloro-p-xylenediamine, m-xylenediamine, p-xylenediamine, m-phenylenediamine, o-phenylenediamine, p-phenylenediamine, 2,4-diaminoanisole, 2,4 -Toluenediamine, 2,4-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 4,4'-diamino-1,2-diphenylethane, 2,4-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, m-aminophenol, m-aminobenzylamine, benzyldimethylamine, 2-dimethylaminomethyl) phenol, triethanolamine, methylbenzylamine, ⁇ - (m-aminophenyl) ethylamine,
  • the acid anhydride-based curing agent include dodecenyl succinic anhydride, polyadipic acid anhydride, polyazeline acid anhydride, polysebacic acid anhydride, poly (ethyloctadecane diacid) anhydride, poly (phenylhexadecane diacid) Anhydride, Methyltetrahydrophthalic anhydride, Methylhexahydrophthalic anhydride, Hexahydrophthalic anhydride, Methylhymic anhydride, Tetrahydrophthalic anhydride, Trialkyltetrahydrophthalic anhydride, Methylcyclohexene dicarboxylic anhydride, Methylcyclohexene tetracarboxylic Acid anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic anhydride, ethylene glycol
  • amide type curing agent examples include dicyandiamide and polyamide resin.
  • tertiary amines include 1,8-diazabicyclo (5,4,0) undecene-7, triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol, and the like. .
  • imidazole and its derivatives examples include 1-cyanoethyl-2-phenylimidazole, 2-phenylimidazole, 2-ethyl-4 (5) -methylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyano-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole trimellitate, 1-cyanoethyl-2-phenylimidazo Lithium trimellitate, 2,4-diamino-6- [2'-methylimidazolyl- (1 ')]-ethyl-s-triazine, 2,4-diamino-6- [2'-ethyl-4'-methyl Imidazolyl- (1 ′)]-ethyl-s-triazine, 2,4-d
  • organic phosphines include tributylphosphine, methyldiphenylphosphine, triphenylphosphine, diphenylphosphine, and phenylphosphine.
  • phosphonium salt examples include tetraphenylphosphonium / tetraphenylborate, tetraphenylphosphonium / ethyltriphenylborate, tetrabutylphosphonium / tetrabutylborate, methyltributylphosphonium dimethylphosphate, and tetrabutylphosphonium benzotriazolate.
  • tetraphenylboron salt include 2-ethyl-4-methylimidazole / tetraphenylborate, N-methylmorpholine / tetraphenylborate and the like.
  • the content ratio (epoxy group / functional group (R)) of the functional group (R) contained in the curing agent with respect to all epoxy groups in the composition for the alignment film is short because the epoxy group is not easily left unreacted. The smaller one is preferable in that it can be sufficiently reacted in time. On the other hand, it is preferable that the functional group (R) is unreacted and hardly remains in the alignment film obtained by curing the alignment film composition of the present invention.
  • an addition polymerization type curing agent it is preferably used so that the equivalent ratio of the functional group (R) of the curing agent to the epoxy group in the alignment film composition is 0.8 or more. More preferably, it is used as described above.
  • the curing agent in an amount of 0.1 parts by weight or more, based on 100 parts by weight of the composition for an alignment film excluding the solvent, and 0.2 parts by weight or more. More preferably, it is used. Moreover, it is preferable to use it so that it may become 20 weight part or less, and it is still more preferable to use it so that it may become 15 weight part or less.
  • the alignment film composition of the present invention may contain a solvent.
  • a solvent When a solvent is used, various materials of the alignment film composition are used in a state of being dissolved or dispersed in the solvent.
  • the solvent preferably has a boiling point (under a pressure of 1013.15 [hPa], the same applies to the boiling points hereinafter) of 80 ° C. or higher, more preferably 100 ° C. or higher.
  • Examples of the solvent include the following. Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol-mono t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, methoxymethylpentanol, propylene Glycol monoalkyl ethers such as glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, tripropylene glycol monomethyl ether; Glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl
  • the solvent preferably has a boiling point of 100 ° C. or higher, and preferably 120 ° C. or higher. Moreover, it is preferable that it is 200 degrees C or less, and it is more preferable that it is 170 degrees C or less.
  • a lower limit coating unevenness and the like tend to be suppressed.
  • drying becomes easy, and it tends to be applied to a substrate having particularly low heat resistance.
  • glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, N , N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone and the like are preferred.
  • the composition for an alignment film of the present invention preferably contains a surfactant in order to improve wettability, applicability and the like when applying the anisotropic dye film.
  • a surfactant for example, an anionic, cationic, nonionic or amphoteric surfactant can be used.
  • a nonionic surfactant in view of the applicability of the alignment film as an anisotropic dye film, and it is preferable to use a fluorine-based or silicon-based surfactant among the alignment film compositions. It is also effective in terms of applicability.
  • fluorine-based surfactant examples include perfluoroalkyl sulfonic acid, perfluoroalkyl carboxylic acid, and fluorine telomer alcohol.
  • silicon surfactants include polyether-modified silicon having various linear and branched chains.
  • surfactants examples include, for example, TSF4460 (manufactured by GE Toshiba Silicone), BYK-300, BYK-325, BYK-330 (manufactured by BYK Chemie), KP340 (manufactured by Shin-Etsu Silicone), SH7PA, in the case of silicon.
  • a fluorine-based surfactant having a polymerizable group is preferable in terms of dispersibility, reduction of defects due to aggregation, and continuity of the effect of the surface active action.
  • Examples of the polymerizable group possessed by the fluorosurfactant include those exemplified in the following formulas U-1 to U-5.
  • a surfactant examples include the Megafac series manufactured by DIC Corporation.
  • the content thereof is preferably 0.001% by mass or more, more preferably 0.005% by mass or more, with respect to the alignment film composition excluding the solvent, 0.01% More preferably, it is more preferably at least 0.03% by mass.
  • 10 mass% or less is preferable, 1 mass% or less is more preferable, 0.5 mass% or less is further more preferable, and 0.3 mass% or less is especially preferable.
  • content of surfactant is the said range.
  • an adhesion improver such as a silane coupling agent
  • examples of the silane coupling agent include epoxy, (meth) acrylic, amino and the like. These may be used alone or in combination of two or more.
  • Preferred silane coupling agents include, for example, (meth) acryloxysilanes such as 3-methacryloxypropylmethyldimethoxysilane and 3-methacryloxypropyltrimethoxysilane; 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane Epoxy silanes such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane; and ureidosilanes such as 3-ureidopropyltriethoxysilane Isocyanate isocyanates such as 3-isocyanatopropyltriethoxysilane; Among these, epoxysilane silane coupling agents are particularly preferable.
  • the content thereof is preferably 0.05% by mass or more, more preferably 0.1% by mass or more with respect to the alignment film composition excluding the solvent. Moreover, 10 mass% or less is preferable and 7 mass% or less is more preferable.
  • the composition for alignment film of the present invention may contain a compound having a partial structure (P) and not having an epoxy group and a functional group (R).
  • a compound having an epoxy group or a functional group (R) can be used in combination or added to cases (1) to (7).
  • a compound having a partial structure (P) and not having an epoxy group and a functional group (R) is limited to the structure, molecular weight, physical properties, etc., as long as the composition can be controlled within the preferred range of the alignment film composition. Rather, it can be used arbitrarily.
  • commercially available products can also be used.
  • commercially available polymers such as polyimide, polyamide, polyester, and polycarbonate having a partial structure (P) can be used.
  • the alignment film composition of the present invention may contain a filler for the purpose of improving the strength.
  • a filler for the purpose of improving the strength.
  • the fillers it is preferable to use an inorganic filler.
  • the inorganic filler include alumina (Al 2 O 3 ), aluminum nitride (AlN), boron nitride (BN), silicon nitride (Si 3 N 4 ), silica (SiO 2 ), and the like.
  • Al 2 O 3 , AlN, BN or SiO 2 is preferable, and Al 2 O 3 , BN or SiO 2 is particularly preferable.
  • These inorganic fillers may be used alone or in a combination of two or more in any combination and ratio.
  • a granular or flat inorganic filler it is preferable to use one having an average particle diameter of about 0.05 to 1000 ⁇ m.
  • an aggregated inorganic filler having an average crystal diameter of 0.01 to 5 ⁇ m and an average aggregate diameter of 1 to 1000 ⁇ m.
  • the content of the filler in the alignment film composition of the present invention is preferably 5 parts by weight or more and more preferably 10 parts by weight or more with respect to 100 parts by weight of the alignment film composition excluding the solvent. Moreover, 1900 weight part or less is preferable and 1800 weight part or less is more preferable.
  • the filler content is not less than the above lower limit, thermal conductivity due to the filler tends to be obtained, and when it is not more than the above upper limit, the curability and physical properties of the alignment film tend to be obtained.
  • the above-described composition for an alignment film of the present invention can produce an alignment film having a high alignment regulating force on the composition for an anisotropic dye film even at a low temperature, and the anisotropic dye film formed on the alignment film It has high orientation characteristics.
  • the alignment film obtained from the alignment film composition of the present invention can easily form an anisotropic ordered structure in which the regularity of the partial structure (P) is increased by performing a surface treatment such as rubbing. It becomes possible to increase the regularity of the alignment film.
  • the alignment film composition of the present invention is particularly useful for an alignment film for an anisotropic dye film, which will be described later, and is suitably used for forming an optical element, particularly a polarizing element, in combination with the anisotropic dye. Can do.
  • An optical element including an alignment film formed from the alignment film composition of the present invention, an anisotropic dye film formed from a dye, and the like is provided.
  • an alignment film formed from the alignment film composition of the present invention an anisotropic dye film formed from a dye, and the like is provided.
  • the composition for an alignment film of the present invention can be obtained by mixing the above compound, reaction mixture, solvent and the like. Moreover, the solid content concentration of the composition for alignment films of the present invention is usually 1% by mass or more, and preferably 3% by mass or more. Moreover, it is 50 mass% or less normally, Preferably it is 30 mass% or less.
  • the composition for an alignment film of the present invention is prepared by using a solvent so as to be in the above range. In the curing of the alignment film composition of the present invention, a method in which the alignment film composition mixed in a predetermined composition is applied to a material to be coated (substrate) by the method and conditions described below and then thermally cured.
  • the manufacturing method of the compound contained in the composition for alignment films of this invention is not specifically limited, It can manufacture using a well-known method.
  • the structure construction method of the compound containing the partial structure (P) is not particularly limited, and construction using a known method and induction into the compound are possible.
  • a partial structure (P) is constructed by using a component having another functional group that can introduce a functional group (R) as a starting material. Later, the functional group (R) may be derivatized.
  • the manufacture example of the compound A and the compound B is shown, the compound E and the compound F can also be obtained by the same method, respectively.
  • Compound A As one specific production example of Compound A, a method for inducing Compound A (Exemplary Compound A3) containing a phthalimide structure as the partial structure (P) will be described.
  • Compound E can also be produced by the same method.
  • the imide skeleton is derived by condensation of an acid anhydride or dicarboxylic acid with an amine, alkylation of a hydrogenated imide, or reaction with an amino group.
  • Method for producing reaction mixture D> There is also a method in which the mixed alignment film composition is caused to undergo a curing reaction at a low reaction rate in advance, and then applied to a material to be coated (substrate), and then heated again to be completely cured.
  • this method is not particularly limited, simple methods include two methods: method (1) phenoxy resin formation and method (2) oligomerization.
  • phenoxy resinization refers to heating a bifunctional epoxy compound together with an addition-type curing agent to induce a soluble linear resin (referred to as a polymer-type epoxy resin or phenoxy resin).
  • the alignment film composition is converted into a phenoxy resin before coating.
  • it is suitable for a combination of a bifunctional epoxy compound and a bifunctional curing agent. If it is the said composition for alignment films, the reaction conversion rate of phenoxy resinification will not be specifically limited.
  • the reaction conversion rate between the epoxy group and the curing agent can be appropriately controlled by reaction conditions such as a catalyst, temperature, and time.
  • a phenoxy resin derived from an epoxy compound having a phthalimide group as a partial structure (P) and a phenol curing agent as shown in the following formula is applied to a coating agent, thereby An alignment film can be obtained.
  • Method (2) is a method using an oligomer solution obtained by heat-curing the alignment film composition adjusted to a predetermined mixing ratio at a low reaction rate before coating. In particular, it can be particularly preferably carried out when a solvent is used for the composition for alignment film.
  • Examples of the method (2) include a method in which the compound A29 exemplified as the compound A and an acid anhydride curing agent are heated for several hours in the presence of a curing aid.
  • the reaction rate of oligomerization can be estimated from the residual epoxy group in the reaction product by 1 H-NMR.
  • the alignment film of the present invention can be formed by applying the alignment film composition of the present invention to a material to be coated.
  • the coating method is not particularly limited as long as it can form a layer having a uniform thickness, for example, die coating, spin coating, screen printing, flexographic printing, spraying, a casting method using an applicator, a method using a coater, Examples thereof include a spraying method, a dipping method, a calendar method, and a casting method.
  • the substrate of the material to be coated for example, glass such as float glass or soda glass, a transparent substrate made of plastic such as polyethylene terephthalate, polycarbonate, polyolefin, or the like can be used.
  • a functional silane-containing compound or a functional titanium-containing compound can be applied in advance to the surface of the substrate. Further, ultraviolet treatment, plasma treatment, or the like can be performed.
  • a step of volatilizing the solvent may be added.
  • a method for volatilizing the solvent is not particularly limited. Usually, it is dried using a hot plate, an infrared oven, a convection oven, hot air heating, microwave heating, a hot roll, a vacuum dryer, a heating vacuum dryer or the like.
  • the degree of reduced pressure is preferably 0.01 to 500 mmHg, and the drying time is selected in the range of 1 second to 10 minutes.
  • the heating temperature when heating to volatilize the solvent can be a suitable temperature depending on the type of the solvent, but is usually 20 ° C. or higher, preferably 40 ° C. or higher, more preferably 60 ° C. or higher. Further, it is preferably 200 ° C. or lower, more preferably 180 ° C. or lower, and further preferably 150 ° C. or lower. When heating temperature is more than the said minimum, it is preferable at the point from which a solvent is fully volatilized.
  • the heating temperature is equal to or lower than the above upper limit, it is preferable because it is possible to suppress deterioration in performance of each material when an alignment film is formed on a material having low heat resistance, for example, a polyester resin or a polyolefin resin.
  • the drying time is usually selected in the range of 15 seconds to 10 minutes, preferably in the range of 30 seconds to 5 minutes, depending on the type of the solvent component, the performance of the dryer used, and the like.
  • a method of drying under reduced pressure and a method of heating may be used in combination, or any of them may be used.
  • the dried coating film is usually cured by further heating.
  • the heating temperature at the time of curing is usually 60 ° C. or higher, preferably 80 ° C. or higher.
  • the temperature is usually 250 ° C. or lower, preferably 230 ° C. or lower, more preferably 200 ° C. or lower, particularly preferably 180 ° C. or lower, and most preferably 150 ° C. or lower.
  • the heating time is not particularly limited, but is 10 minutes to 5 hours, preferably 30 minutes to 4 hours.
  • the heating temperature and time depend on the partial structure (P), the type of curing agent, the type of solvent, etc., but the mechanical properties of the resulting alignment film, the orientation regulating force on the anisotropic dye composition, the surface of rubbing, etc.
  • the heat-resistant temperature of the substrate the heat-resistant temperature of other materials for liquid crystal displays, and the reduction of energy used
  • the above ranges are preferred.
  • the partial structure (P) cures while forming an anisotropic ordered structure, so the resulting alignment film has a domain with an anisotropic ordered structure and is formed on its surface.
  • the orientation of the anisotropic dye film can be increased.
  • the alignment film has an anisotropic regular structure and has an appropriate film strength, so that regularity is further increased by surface treatment such as rubbing, and is formed on the surface.
  • the orientation of the anisotropic dye film can be increased.
  • the reaction of the epoxy group proceeds at an appropriate rate, and the alignment film tends to form a regular structure and tends to have a strength that is easy to surface treatment such as rubbing. is there.
  • productivity tends to be excellent.
  • the heating method for curing is not particularly limited, but by gradually raising the temperature from a low temperature, the anisotropic ordered structure of the partial structure (P) tends to be more easily formed.
  • the thickness of the alignment film is usually 1 nm or more, preferably 5 nm or more, more preferably 10 nm or more so that the film can be uniformly formed and sufficient alignment characteristics are exhibited. Usually, it is 10 ⁇ m or less, preferably 1 ⁇ m or less, more preferably 500 nm or less.
  • the coated surface obtained above is rubbed in a certain direction with a roll wound with a cloth made of fibers such as nylon, rayon, cotton, etc., irradiated with linearly polarized light, etc. It can be performed by orienting the molecules by applying a surface treatment or applying an external force such as a magnetic field. By performing these treatments, it is possible to produce an alignment film having a higher alignment regulating force on the anisotropic dye film composition.
  • the anisotropic dye film used in combination with the alignment film composition of the present invention is formed by a wet film formation method.
  • the anisotropic dye film is obtained by using an anisotropic dye film composition containing a dye and a solvent. Moreover, binder resin, a monomer, a hardening
  • the anisotropic dye film composition may be in the form of a solution or gel.
  • the composition for anisotropic dye film may be in a state in which a dye or the like is dissolved or dispersed in a solvent.
  • the composition for an anisotropic dye film is in a liquid crystal phase state if the concentration is changed, or is formed after the solvent in the composition is evaporated to be in a liquid crystal phase state as a composition.
  • the state of the liquid crystal phase refers to the state described on pages 1 to 16 of “Basics and Applications of Liquid Crystals” (Shinichi Matsumoto, Ryo Tsunoda, 1991). Say. In particular, the nematic phase described on page 3 is preferred.
  • the dye a dichroic dye is usually used.
  • the dye is preferably a dye having a liquid crystal phase.
  • the dye having a liquid crystal phase means a dye exhibiting lyotropic liquid crystallinity in a solvent.
  • the lyotropic liquid crystalline compound used in the present invention is preferably soluble in water or an organic solvent, and particularly preferably water-soluble, for use in the wet film forming method described later.
  • Further preferred are compounds having an inorganic value smaller than the organic value as defined in “Organic Conceptual Diagram-Fundamentals and Applications” (Yoshio Koda, Sankyo Publishing, 1984).
  • the molecular weight is preferably 200 or more, and particularly preferably 300 or more.
  • the molecular weight is preferably 1500 or less, and particularly preferably 1200 or less.
  • water-soluble means that the compound is usually dissolved in water at 0.1% by mass or more, preferably 1% by mass or more at room temperature. Only one type of lyotropic liquid crystalline compound may be used, or two or more types may be used in combination.
  • the dye examples include azo dyes, stilbene dyes, cyanine dyes, phthalocyanine dyes, and condensed polycyclic dyes (perylene, oxazine, indanthrone, and the like). Since these dyes are water-soluble, it preferably has a sulfo group.
  • an azo dye that can take a high molecular arrangement in the anisotropic dye film by the combination of the alignment film composition of the present invention is preferable.
  • An azo dye means a dye having at least one azo group.
  • the number of azo groups in one molecule is preferably 2 or more, preferably 6 or less, and more preferably 4 or less, from the viewpoints of color tone and production.
  • the dye used in the present invention is not particularly limited, and a known dye can be used.
  • Examples of the dye include, for example, Japanese Unexamined Patent Publication No. 2006-0799030, Japanese Unexamined Patent Publication No. 2010-168570, Japanese Unexamined Patent Publication No. 2007-302807, Japanese Unexamined Patent Publication No. 2008-081700, Japanese Unexamined Patent Publication No.
  • azo dyes disazo, trisazo and tetrakisazo dyes having the structure of the following formula (12) in the form of free acid have low wavelength dispersibility and a color tone having a wide absorption in the visible region. This is preferable.
  • E 1 represents any organic group
  • R 30 and R 31 each independently represent a hydrogen atom, an alkyl group that may have a substituent, a phenyl group that may have a substituent, or an acyl group that may have a substituent.
  • p and q are each independently an integer of 0 to 6, and p + q is 6 or less.
  • p and q are each independently preferably an integer of 0 to 2. Further, p + q is preferably 1 or more, and more preferably 2 or more. Further, p + q is preferably 4 or less. By being in the above range, the solubility of the dye in water or an organic solvent and the association characteristics tend to be obtained.
  • each of the disazo, trisazo and tetrakisazo dyes having the partial structure of the formula (13) in the form of a free acid has low wavelength dispersion and absorbs a wide range in the visible region.
  • E 2 represents any organic group
  • R 32 and R 33 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or a phenyl group which may have a substituent.
  • the dye in the present embodiment may be used in the form of a free acid, or a part of the acid group may have a salt form. Further, a salt-type dye and a free acid-type dye may be mixed. Moreover, when it is obtained in a salt form at the time of production, it may be used as it is or may be converted into a desired salt form.
  • a salt-type exchange method a known method can be arbitrarily used, and examples thereof include the following methods.
  • a strong acid such as hydrochloric acid is added to an aqueous solution of a dye obtained in a salt form, the dye is acidified in the form of a free acid, and then the dye is added with an alkaline solution having a desired counter ion (for example, an aqueous lithium hydroxide solution).
  • a method of neutralizing acidic groups and salt exchange is performed.
  • a neutral salt eg, lithium chloride
  • An aqueous solution of a dye obtained in a salt form is treated with a strongly acidic cation exchange resin, and the dye is acidified in the form of a free acid, and then an alkali solution having a desired counter ion (for example, an aqueous lithium hydroxide solution). ) To neutralize the acidic group of the dye and perform salt exchange. 4) A method of performing salt exchange by allowing an aqueous solution of a dye obtained in a salt form to act on a strongly acidic cation exchange resin previously treated with an alkaline solution having a desired counter ion (for example, an aqueous lithium hydroxide solution).
  • the acidic group of the dye in the present embodiment is a free acid type or a salt type depends on the pKa of the dye and the pH of the aqueous dye solution.
  • the salt type include salts of alkali metals such as Na, Li and K, ammonium salts which may be substituted with alkyl groups or hydroxyalkyl groups, and organic amine salts.
  • the organic amine include a lower alkyl amine having 1 to 6 carbon atoms, a hydroxy-substituted lower alkyl amine having 1 to 6 carbon atoms, a carboxy-substituted lower alkyl amine having 1 to 6 carbon atoms, and the like.
  • the type is not limited to one type, and a plurality of types may be mixed.
  • dye can be used independently, these 2 or more types may be used together, and pigment
  • Examples of blending dyes when blending other dyes include C.I. I. Direct Yellow 12, C.I. I. Direct Yellow 34, C.I. I. Direct Yellow 86, C.I. I. Direct Yellow 142, C.I. I. Direct Yellow 132, C.I. I. Acid Yellow 25, C.I. I. Direct Orange 39, C.I. I. Direct Orange 72, C.I. I. Direct Orange 79, C.I. I. Acid Orange 28, C.I. I. Direct Red 39, C.I. I. Direct Red 79, C.I. I. Direct Red 81, C.I. I. Direct Red 83, C.I. I. Direct Red 89, C.I. I. Acid Red 37, C.I. I. Direct Violet 9, C.I.
  • the concentration of the dye in the composition for the anisotropic dye film is preferably 0.01% by weight or more, more preferably 0.1% by weight or more, and particularly preferably 5% by weight or more, although it depends on the film forming conditions. More preferably, it is 7 mass% or more. Further, it is preferably 50% by weight or less, more preferably 30% by weight or less.
  • the dye concentration is in the above range, the viscosity does not become too high, and a uniform thin film can be applied.
  • solvent water, a water-miscible organic solvent, a mixture thereof and the like are suitable.
  • organic solvent include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and glycerin, glycols such as ethylene glycol and diethylene glycol, and cellosolves such as methyl cellosolve and ethyl cellosolve. These may be used alone or in combination of two or more.
  • the anisotropic dye film composition may further contain additives such as a surfactant, a leveling agent, a coupling agent, and a pH adjusting agent. Depending on the additive, wettability, applicability and the like may be improved.
  • a surfactant any of anionic, cationic and nonionic properties can be used.
  • the addition concentration is not particularly limited, but it is usually preferably 0.05% by weight or more and 0.5% by weight or less as the concentration in the composition for anisotropic dye film. By being in these ranges, it is sufficient to obtain the added effect and does not tend to inhibit the orientation of the dye molecules.
  • a known pH adjuster such as acid / alkali is added to the anisotropic dye. It may be added either before or after mixing the components of the film composition or during mixing.
  • “Additive for Coating”, Edited by J. et al. Known additives described in Bieleman, Willy-VCH (2000) can also be used.
  • anthraquinone compound may be blended in the anisotropic dye film composition of the present invention in accordance with the methods described in Japanese Patent Application Publication No. 2007-199333 and Japanese Patent Application Publication No. 2008-101154. Furthermore, the methods described in Japanese Unexamined Patent Publication No. 2006-3864 and Japanese Unexamined Patent Publication No. 2006-323377 may be used. Further, the composition for anisotropic dye film of the present invention is based on the acidic group of the azo compound in the composition for anisotropic dye film as described in Japanese Patent Application Laid-Open No. 2007-178993. A cation of 0.9 equivalent or more, 0.99 equivalent or less, and a strongly acidic anion of 0.02 equivalent or more and 0.1 equivalent or less, etc. It is possible to control the defects of the anisotropic dye film by setting the time until the relaxation elastic modulus G after applying the strain to 0.01 seconds after the strain application is reduced to 1/10, 0.1 seconds or less.
  • the wet film-forming method referred to in the present invention is a method in which an anisotropic dye film composition is applied to an alignment film by any method, and a dye is aligned and laminated on a substrate through a process of drying a solvent. is there.
  • the anisotropic dye film composition when the anisotropic dye film composition is formed on the substrate, the dye itself self-associates in the anisotropic dye film composition or in the process of drying the solvent. By doing so, orientation in a minute area occurs.
  • an anisotropic dye film having desired performance can be obtained by orienting in a constant direction in a macro region.
  • PVA polyvinyl alcohol
  • the external field includes the influence of a treatment layer such as an alignment film previously applied on the substrate, shear force, magnetic field, etc., and these may be used alone or in combination. Good.
  • the process of forming the composition for an anisotropic dye film on the substrate, the process of aligning by applying an external field, and the process of drying the solvent may be performed sequentially or simultaneously.
  • Examples of the method for applying the anisotropic dye film composition on the substrate in the wet film forming method include a coating method, a dip coating method, an LB film forming method, a known printing method, and the like. There is also a method of transferring the anisotropic dye film thus obtained to another substrate.
  • the present invention preferably uses a coating method.
  • An anisotropic dye film can be formed by applying the composition for anisotropic dye film to a material to be coated.
  • the orientation direction of the anisotropic dye film is usually coincident with the application direction, but may be different from the application direction.
  • the orientation direction of the anisotropic dye film is, for example, a transmission axis or absorption axis of polarized light in the case of an anisotropic dye film, and a fast axis or in the case of a retardation film. It is the slow axis.
  • the anisotropic dye film in the present embodiment functions as a polarizing film or retardation film that obtains linearly polarized light, circularly polarized light, elliptically polarized light, etc. by utilizing the anisotropy of light absorption, as well as a film forming process and a substrate or organic film.
  • a composition containing a compound pigment or transparent material
  • it can be functionalized as various anisotropic films such as refractive anisotropy and conduction anisotropy.
  • the method for applying the anisotropic dye film composition to obtain the anisotropic dye film is not particularly limited.
  • Yuji Harasaki's “Coating Engineering” (Asakura Shoten Co., Ltd., published on March 20, 1971), pages 253-277, supervised by Kunihiro Ichimura, “Creation and Application of Molecular Cooperative Materials” MC Publishing, published on March 3, 1998)
  • the coating method include a bar coating method, a roll coating method, a blade coating method, a curtain coating method, a fountain method, and a dip method.
  • the slot die coating method is preferable because an anisotropic dye film with high uniformity can be obtained.
  • the method for supplying the composition for anisotropic dye film and the supply interval when applying the composition for anisotropic dye film continuously are not particularly limited. Since the coating liquid supply operation is simplified and fluctuations in the coating film thickness at the start and stop of the coating liquid tend to be suppressed. It is desirable to apply while supplying the composition for anisotropic dye film.
  • the speed at which the composition for anisotropic dye film is applied is usually 1 mm / second or more, preferably 5 mm / second or more, and usually 1000 mm / second or less, preferably 200 mm / second or less.
  • coating speed is at least the above lower limit, the anisotropy of the anisotropic dye film tends to be easily obtained.
  • coating temperature of the composition for anisotropic dye films it is 0 degreeC or more and 80 degrees C or less normally, Preferably it is 40 degrees C or less.
  • it is 10% RH or more, More preferably, it is 30% RH or more, Preferably it is 80 RH% or less.
  • the film thickness of the anisotropic dye film is preferably 10 nm or more, more preferably 50 nm or more as a dry film thickness. On the other hand, it is preferably 30 ⁇ m or less, more preferably 1 ⁇ m or less. When the film thickness of the anisotropic dye film is in an appropriate range, there is a tendency that uniform orientation of molecules and a uniform film thickness can be obtained in the film.
  • the anisotropic dye film may be insolubilized.
  • Insolubilization means a treatment step that increases the stability of the film by controlling the elution of the compound from the anisotropic dye film by reducing the solubility of the compound in the anisotropic dye film.
  • an ion with a lower valence is replaced with an ion with a higher valence (for example, a monovalent ion is replaced with a polyvalent ion), or an organic molecule or polymer having a plurality of ionic groups.
  • a replacement process is listed.
  • the obtained anisotropic dye film is treated by a method described in Japanese Patent Application Laid-Open No. 2007-241267, etc. to obtain an anisotropic dye film insoluble in water. It is preferable in terms of ease and durability.
  • the transmittance in the visible light wavelength region of the anisotropic dye film of the present invention is preferably 25% or more. 35% or more is more preferable, and 40% or more is particularly preferable.
  • permeability should just be an upper limit according to a use. For example, when increasing the degree of polarization, it is preferably 50% or less.
  • the transmittance is in a specific range, it is useful as the following optical element, and particularly useful as an optical element for a liquid crystal display used for color display.
  • the optical element is a polarizing element that obtains linearly polarized light, circularly polarized light, elliptically polarized light, etc. by utilizing the anisotropy of light absorption, a phase difference element, or an element having functions such as refractive anisotropy and conduction anisotropy. These functions can be appropriately adjusted depending on the film formation process and the selection of the composition containing the substrate and organic compound (pigment or transparent material). In the present invention, it is preferably used as a polarizing element.
  • the polarizing element of the present invention is not particularly limited as long as it has at least an alignment film formed from the alignment film composition of the present invention and an anisotropic dye film containing a dye, and any other film (layer) may be used. You may have. For example, it can be produced by forming an anisotropic dye film on the surface of the alignment film formed by the above method as described above.
  • an overcoat layer in addition to the alignment film and the anisotropic dye film, an overcoat layer, an adhesive layer, an antireflection layer, a layer having a function as a retardation film, and a brightness enhancement film
  • Layers with various functions such as a layer having a function as a reflective film, a layer having a function as a reflective film, a layer having a function as a transflective film, a layer having a function as a diffusion film, etc. are laminated by coating or bonding. It may be formed and used as a laminate.
  • These layers having an optical function can be formed, for example, by the following method.
  • the layer having a function as a retardation film can be formed by bonding a retardation film obtained by the following method to another layer constituting the polarizing element.
  • the retardation film is subjected to stretching treatment described in, for example, JP-A-2-59703, JP-A-4-230704, or the like, or described in JP-A-7-230007. It can be formed by processing.
  • the layer having a function as a brightness enhancement film can be formed by bonding the brightness enhancement film obtained by the following method to another layer constituting the polarizing element.
  • the brightness enhancement film is formed by forming micropores by a method as described in, for example, Japanese Patent Application Laid-Open No. 2002-169025 and Japanese Patent Application Laid-Open No. 2003-29030, or the central wavelength of selective reflection is different. It can be formed by overlapping two or more cholesteric liquid crystal layers.
  • a layer having a function as a reflective film or a transflective film can be formed, for example, by bonding a metal thin film obtained by vapor deposition or sputtering to another layer constituting the polarizing element. it can.
  • the layer having a function as a diffusion film can be formed, for example, by coating the other layer constituting the polarizing element with a resin solution containing fine particles.
  • the layer having a function as a retardation film or an optical compensation film is formed by applying and aligning a liquid crystalline compound such as a discotic liquid crystalline compound or a nematic liquid crystalline compound on another layer constituting the polarizing element. be able to.
  • the anisotropic dye film in the present embodiment is used as an anisotropic dye film for various display elements such as LCDs and OLEDs, it is directly anisotropic on the surface of the electrode substrate or the like constituting these display elements.
  • a dye film can be formed, or a substrate on which an anisotropic dye film is formed can be used as a constituent member of these display elements.
  • the optical element of the present invention can be suitably used for applications such as a flexible display because a polarizing element can be obtained by forming it on a substrate by coating or the like.
  • Z 1 represents a divalent group having a cyclic imide structure
  • Z 2 and Z 3 each independently represent a direct bond or any divalent group
  • Z 4 represents a divalent group having an aromatic ring
  • n represents an integer of 1 or more and 500 or less.
  • (Z 1 ) Z 1 is a divalent group having a cyclic imide structure.
  • the cyclic imide structure may be a single ring or may have a plurality of rings.
  • the number of rings that the cyclic imide structure has is not particularly limited, but is preferably 3 or less. Further, the position at which Z 1 is connected to Z 2 and Z 3 is not particularly limited.
  • Specific examples of the cyclic imide structure include phthalimide, succinimide, glutarimide, 3-methylglutarimide, maleimide, dimethylmaleimide, trimellitimide, and pyromelliticimide. Among these, it is preferable to have a phthalimide structure.
  • Z 1 may have other groups besides the cyclic imide structure.
  • aromatic hydrocarbon groups such as benzene ring and naphthalene ring
  • aromatic heterocyclic groups such as pyridine and pyrimidine
  • alkylene groups having 1 to 8 carbon atoms alkenylene groups having 1 to 8 carbon atoms
  • heteroatoms amides Group
  • ester group and the like said group may have a substituent, for example, a hetero atom, an amino group, etc. are mentioned.
  • a group other than the cyclic imide structure a group having a benzene ring, an unsaturated bond and / or a hetero atom is preferable.
  • Examples of the group having an unsaturated bond and / or a hetero atom include —O—C ( ⁇ O) —, —NH—C ( ⁇ O) —, —C ( ⁇ O) —, —C ⁇ C— And C ( ⁇ O) —, — (O ⁇ ) S ( ⁇ O) —, —O— and the like.
  • Examples of Z 1 include a structure represented by the following formula (16).
  • (Z 2 and Z 3 ) Z 2 and Z 3 each independently represent a direct bond or an arbitrary divalent group.
  • Aromatic hydrocarbon groups such as a benzene ring and a naphthalene ring
  • Aromatic heterocyclic groups such as a pyridine and a pyrimidine
  • C1-C8 alkylene group The alkenylene group of 8 or less or more; the group which combined these, etc. are mentioned.
  • said group may have a substituent, for example, a hetero atom, an amino group, etc. are mentioned.
  • an aromatic hydrocarbon group and / or an alkylene group having 1 to 8 carbon atoms is preferable.
  • (Z 4 ) Represents a divalent group having an aromatic ring.
  • the divalent group having an aromatic ring is not particularly limited, and examples thereof include an aromatic hydrocarbon group such as a benzene ring and a naphthalene ring, an aromatic heterocyclic group such as pyridine and pyrimidine, and combinations of the above groups.
  • the ring may be condensed with an aliphatic ring. Furthermore, you may use combining the said ring, a C1-C8 alkylene group, a C1-C8 alkenylene group, etc.
  • the above groups and rings may have a substituent, and examples thereof include an alkyl group having 1 to 8 carbon atoms, a hetero atom, and an amino group.
  • the precipitate was filtered off and washed with methanol.
  • the obtained solid was dissolved in 300 ml of DMF, added little by little in 600 ml of methanol, and the precipitate was filtered off. After washing with methanol and drying, 15 g of a pale yellow powder of dicarboxylic acid which is a precursor of Compound 3 was obtained. After dissolving 3.0 g (5.5 mmol) of the dicarboxylic acid obtained above in 50 ml of NMP, 1.52 g (11 mmol) of potassium carbonate was added. After stirring at an internal temperature of 50 ° C.
  • the silica gel column was purified with a chloroform-toluene mixed solvent, and 1.0 g of 2- [3- [4- (5-oxiranylmethoxycarbonyl-1,3-dihydro-1,3-dioxo-2H] was obtained.
  • 2- [3- [4- (5-oxiranylmethoxycarbonyl-1,3-dihydro-1,3-dioxo-2H] was obtained.
  • -Isoindole-2-yl) phenoxy] phenyl] -2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid oxiranyl methyl ester (compound 3) was obtained.
  • Example 1 The compound and curing agent shown in Example 1 of Table 1 are weighed into a sample bottle, dissolved in the solvent described in Example 1 of Table 1 so as to have a solid content concentration of 7 wt%, and then filtered to obtain an orientation. A film composition 1 was obtained. This alignment film composition 1 was applied onto a glass substrate by a spin coating method, heated at 80 ° C. for 1 minute, and then cured with the curing time described in Table 1, thereby obtaining alignment film 1. The alignment film 1 was rubbed in one direction using a rayon cloth.
  • the anisotropic dye film composition is applied using a die coater having a slot width of 50 ⁇ m, and then naturally dried, whereby the anisotropic dye film is dried. 1 was obtained.
  • compositions for alignment films 11 and 12, alignment films 11 and 12, and anisotropic dye films 11 and 12 were obtained.
  • the alignment film was evaluated by evaluating the optical performance of the obtained anisotropic dye film.
  • the optical performance was evaluated as follows based on the single transmittance and the degree of polarization of the anisotropic dye film. Evaluation was carried out as follows from the single transmittance and the degree of polarization.
  • C Single transmittance of 36% or more Polarization degree is less than 95.5%
  • the single transmittance and the degree of polarization were determined using a spectrophotometer equipped with a Gram-Thomson polarizer (product name “RETS-100” manufactured by Otsuka Electronics Co., Ltd.).
  • the linearly polarized measuring light was incident on the anisotropic dye film and the transmittance was measured.
  • the degree of polarization at 620 nm which is the maximum absorption wavelength of the anisotropic dye film, was calculated by the following equation.
  • Polarization degree (P) (%) ⁇ (Ty ⁇ Tz) / (Ty + Tz) ⁇ 1/2 ⁇ 100
  • Tz transmittance for polarized light in the direction of the absorption axis of the anisotropic dye film
  • Ty transmittance for polarized light in the direction of the polarization axis of the anisotropic dye film
  • the alignment film of the present invention has a high alignment regulating force on the composition for anisotropic dye films.
  • the alignment films of Comparative Example 1 and Comparative Example 2 that do not have the partial structure (P) have low optical characteristics of the anisotropic dye film, and have an alignment regulating force on the composition for the anisotropic dye film. It was shown not enough.
  • (*) indicates the ratio (mass%) of the partial structure (P1) and / or partial structure (P2) in the cured alignment film and in the alignment film composition excluding the solvent of each compound or reaction mixture. Represents. Moreover, (***) represents the ratio (mass%) of the partial structure (P1) and / or the partial structure (P2) in the cured alignment film and the alignment film composition excluding the solvent.
  • Compound A in Examples 1, 2, and 6 also belongs to Compound E
  • Compound B in Examples 4 to 9 also belongs to Compound F
  • Compound C in Examples 4, 5, and 7 are compounds G Also belongs to.
  • TG3DAS Tetraglycidyl 3,3'-diaminodiphenyl sulfone (manufactured by Konishi Chemical Co., Ltd.)
  • V8005 Polyamideimide (manufactured by DIC Corporation) jER828: Bisphenol A type epoxy (Mitsubishi Chemical Corporation) YX4000: Biphenyl type epoxy (manufactured by Mitsubishi Chemical Corporation) BAPP: 2,2-bis [4- (4-aminophenoxy) phenyl] propane (manufactured by Tokyo Chemical Industry Co., Ltd.) TPP: Triphenylphosphine (manufactured by Tokyo Chemical Industry Co., Ltd.) DBU: 1,8-diazabicyclo [5.4.0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) Hishicolin 4MP: Methyltributylphosphonium dimethyl phosphate (manufactured by Nippon Chemical Industry Co., Ltd.) YH300: Tetrahydromethylphthalic anhydride (Mitsubishi Chemical Corporation) Catechol: Tokyo Kasei Co., Ltd. NMP: 1-methyl-2-pyrrolidon
  • the present invention can be used in any industrial field, but can be suitably used in, for example, a field where an alignment film having a high alignment regulating force for an anisotropic dye film composition is required. Specifically, it can be particularly suitably used in the optical field, for example, a field where an optical element such as a display is required.

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  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Epoxy Resins (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)

Abstract

La présente invention aborde le problème consistant à fournir : un film d'alignement ayant une force d'ancrage élevée ; et une composition à partir de laquelle un film d'alignement ayant une force d'ancrage élevée sur une composition pour un film de colorant anisotrope ou similaire peut être produit même à une basse température. La présente invention concerne un film d'alignement durci en résine époxy contenant une structure partielle (P1) et/ou une structure partielle (P2), la proportion de la structure partielle (P1) et/ou de la structure partielle (P2) dans le film d'alignement durci en résine époxy étant de 0,5 % en masse ou plus. Dans le film d'alignement, la structure partielle (P1) est un cycle aromatique contenant un hétéroatome, et la structure partielle (P2) est représentée par la formule (1) (dans laquelle R1 représente un groupe bivalent contenant un hétéroatome et ayant une liaison insaturée ; et le cycle lié à R1 représente un cycle monocyclique).
PCT/JP2016/067803 2015-06-16 2016-06-15 Film d'alignement, et composition pour films d'alignement WO2016204178A1 (fr)

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JP2017525261A JP6922736B2 (ja) 2015-06-16 2016-06-15 配向膜及び配向膜用組成物
CN201680031589.9A CN107683427B (zh) 2015-06-16 2016-06-15 取向膜以及取向膜用组合物
KR1020177036033A KR102560883B1 (ko) 2015-06-16 2016-06-15 배향막 및 배향막용 조성물

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Publication number Priority date Publication date Assignee Title
JP2018131619A (ja) * 2017-02-14 2018-08-23 味の素株式会社 樹脂組成物
JP7151092B2 (ja) 2017-02-14 2022-10-12 味の素株式会社 樹脂組成物

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CN107683427A (zh) 2018-02-09
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JP6922736B2 (ja) 2021-08-18
KR102560883B1 (ko) 2023-07-31

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