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WO2014104320A1 - Composition pour former un film durci, matériau à orientation et matériau à différence de phase - Google Patents

Composition pour former un film durci, matériau à orientation et matériau à différence de phase Download PDF

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Publication number
WO2014104320A1
WO2014104320A1 PCT/JP2013/085165 JP2013085165W WO2014104320A1 WO 2014104320 A1 WO2014104320 A1 WO 2014104320A1 JP 2013085165 W JP2013085165 W JP 2013085165W WO 2014104320 A1 WO2014104320 A1 WO 2014104320A1
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Prior art keywords
cured film
group
component
alignment
ester
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PCT/JP2013/085165
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English (en)
Japanese (ja)
Inventor
昇志郎 湯川
石田　智久
真 畑中
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to KR1020157018928A priority Critical patent/KR102182361B1/ko
Priority to JP2014554603A priority patent/JP6372022B2/ja
Priority to CN201380068435.3A priority patent/CN104903405B/zh
Publication of WO2014104320A1 publication Critical patent/WO2014104320A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/132—Phenols containing keto groups, e.g. benzophenones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3083—Birefringent or phase retarding elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking

Definitions

  • the present invention relates to a cured film forming composition, an alignment material, and a retardation material.
  • a right-eye image is visually recognized by an observer's right eye
  • a left-eye image is visually recognized by an observer's left eye, whereby a stereoscopic image can be displayed.
  • a retardation material is usually disposed on a display element such as a liquid crystal panel.
  • a retardation material a plurality of two kinds of retardation regions having different retardation characteristics are regularly arranged, and a patterned retardation material is formed.
  • a retardation material patterned so as to arrange a plurality of retardation regions having different retardation characteristics is referred to as a patterned retardation material.
  • the patterned retardation material can be produced, for example, by optically patterning a retardation material made of a polymerizable liquid crystal as disclosed in Patent Document 2.
  • Optical patterning of a retardation material made of a polymerizable liquid crystal utilizes a photo-alignment technique known for forming an alignment material for a liquid crystal panel. That is, a coating film made of a photo-alignment material is provided on a substrate, and two types of polarized light having different polarization directions are irradiated on the coating film. Then, a photo-alignment film is obtained as an alignment material in which two types of liquid crystal alignment regions having different liquid crystal alignment control directions are formed.
  • a solution-like retardation material containing a polymerizable liquid crystal is applied on the photo-alignment film to realize the alignment of the polymerizable liquid crystal. Thereafter, the aligned polymerizable liquid crystal is cured to form a patterned retardation material.
  • acrylic resins and polyimide resins having photodimerization sites such as cinnamoyl groups and chalcone groups in the side chain are known as usable photo-alignment materials.
  • These resins have been reported to exhibit the ability to control the alignment of liquid crystals (hereinafter also referred to as liquid crystal alignment) by irradiation with polarized UV light (see Patent Documents 3 to 5).
  • an acrylic resin having a photodimerization site such as a cinnamoyl group or a chalcone group in the side chain is, for example, a liquid crystal alignment property or a solvent resistance when applied to the formation of a retardation material. It has been found that sufficient characteristics cannot be obtained.
  • a large amount of polarized UV exposure is required. .
  • the polarized UV exposure amount is much larger than the polarized UV exposure amount (for example, about 50 mJ / cm 2 ) sufficient to align the liquid crystal for a normal liquid crystal panel.
  • an alignment material is formed using an acrylic resin having a photodimerization site such as a cinnamoyl group in the side chain, and the polymerizable liquid crystal is to be aligned, first, light generated by a photodimerization reaction in the acrylic resin or the like. Crosslinking proceeds. Furthermore, it is necessary to irradiate polarized light so as to develop resistance (solvent resistance) to the polymerizable liquid crystal solution.
  • a photo-alignment technique capable of improving the alignment sensitivity of the alignment material and reducing the polarized UV exposure amount, and a cured film forming composition used for forming the alignment material are required. And the technique which can provide a patterned phase difference material with high efficiency is calculated
  • an object of the present invention is to provide a cured film forming composition for providing an alignment material having excellent photoreaction efficiency and solvent resistance, and capable of aligning a polymerizable liquid crystal with high sensitivity. It is.
  • Another object of the present invention is an alignment material obtained from the cured film-forming composition, having an excellent photoreaction efficiency and having solvent resistance, and capable of aligning a polymerizable liquid crystal with high sensitivity, and its The object is to provide a retardation material formed using an alignment material.
  • the first aspect of the present invention is: (A) A compound having a photo-alignment group and at least one substituent selected from a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group, and (B) capable of thermal reaction with the component (A).
  • the present invention relates to a cured film-forming composition comprising a polymer having various substituents and capable of self-crosslinking.
  • the photoalignable group of the component (A) is a functional group having a structure that undergoes photodimerization or photoisomerization.
  • the photoalignable group of the component (A) is preferably a cinnamoyl group.
  • the photoalignable group of the component (A) is preferably a group having an azobenzene structure.
  • the polymer of the component (B) preferably has a weight average molecular weight of 1,000 to 100,000.
  • the second aspect of the present invention relates to an alignment material obtained using the thermosetting film forming composition of the first aspect of the present invention.
  • the third aspect of the present invention relates to a retardation material formed using a cured film obtained from the cured film forming composition of the first aspect of the present invention.
  • a cured film forming composition for providing an alignment material having excellent photoreaction efficiency and solvent resistance and capable of aligning a polymerizable liquid crystal with high sensitivity. be able to.
  • the second aspect of the present invention it is possible to provide an alignment material that has excellent photoreaction efficiency and solvent resistance and can align the polymerizable liquid crystal with high sensitivity.
  • a retardation material capable of optical patterning with high efficiency can be provided.
  • the cured film forming composition of the present invention includes (A) a compound having a photo-alignment group and at least one substituent selected from any of a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group, (B) (A) It contains a component having a substituent capable of thermally reacting with the component and capable of self-crosslinking.
  • the cured film forming composition of the present invention can further contain a crosslinking catalyst as the component (C) in addition to the component (A) and the component (B). And as long as the effect of this invention is not impaired, another additive can be contained.
  • the component (A) includes a photo-alignment group and a compound having at least one group selected from a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group.
  • the component (A) is also referred to as “(low molecular weight) photo-alignment component”.
  • the photo-alignment group generally refers to a functional group that exhibits the property of being aligned by light irradiation, and typically refers to a functional group at a structural site that undergoes photodimerization or photoisomerization.
  • photo-alignment groups examples include a functional group that causes a photofleece rearrangement reaction (example compound: benzoate ester compound), a group that causes a photodecomposition reaction (example compound: cyclobutane ring, etc.), and the like.
  • the structure part which the compound of a component can have as a photo-alignment group is the structure part which forms a dimer by light irradiation,
  • a cinnamoyl group, a chalcone group, a coumarin is mentioned as the specific example. Group, anthracene group and the like. Of these, a cinnamoyl group is preferred because of its high transparency in the visible light region and high photodimerization reactivity.
  • the photoisomerizable structural site that the compound of component (A) can have as a photoalignable group refers to a structural site that changes into a cis form and a trans form by light irradiation, and specific examples thereof include an azobenzene structure. And a site comprising a stilbene structure and the like. Of these, an azobenzene structure is preferred because of its high reactivity.
  • Compounds having a photoalignment group and at least one substituent selected from any of a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group include, for example, the following formulas [A-11] to [A- 15].
  • a 1 and A 2 each independently represent a hydrogen atom or a methyl group.
  • X 11 is a single bond, an ether bond, an ester bond, an amide bond, a urethane bond, an amino bond, or a combination thereof, or a combination thereof, or through one or more bonds.
  • a structure in which 1 to 3 substituents selected from alkylene having 1 to 18 carbon atoms, phenylene, biphenylene, or a combination thereof are bonded to each other, and a plurality of these substituents are linked via the bond. It may be a structure.
  • X 12 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a cyclohexyl group.
  • an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, and a cyclohexyl group may be bonded to two or more groups via a covalent bond, an ether bond, an ester bond, an amide bond, or a urea bond. Good.
  • X 13 represents a hydroxy group, a mercapto group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a phenoxy group, a biphenyloxy group, or a phenyl group.
  • X 14 represents a single bond, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring group, or a divalent aliphatic ring group.
  • the alkylene group having 1 to 20 carbon atoms may be branched or linear.
  • X 15 represents a hydroxy group, a carboxyl group, an amino group or an alkoxysilyl group.
  • X 16 represents a single bond, an oxygen atom or a sulfur atom.
  • the benzene ring when these substituents include a benzene ring, the benzene ring includes an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a trifluoromethyl group, and a cyano group. It may be substituted with one or a plurality of substituents which are the same or different.
  • R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom. To 4 alkoxy groups, a halogen atom, a trifluoromethyl group or a cyano group;
  • the compound having a photo-alignable group and a hydroxy group as the component (A) include, for example, compounds represented by the above formulas [A11] to [A15] and compounds other than the above formulas such as 4- ( 8-hydroxyoctyloxy) cinnamic acid methyl ester, 4- (6-hydroxyhexyloxy) cinnamic acid methyl ester, 3-methoxy-4- (6-hydroxyhexyloxy) cinnamic acid methyl ester, 4- (4 -Hydroxybutyloxy) cinnamic acid methyl ester, 4- (3-hydroxypropyloxy) cinnamic acid methyl ester, 4- (2-hydroxyethyloxy) cinnamic acid methyl ester, methyl 4-hydroxymethyloxycinnamic acid Esters, 4-hydroxycinnamic acid methyl ester, 4- (8-hydroxyoctyloxy) cinnamic acid Chill ester, 4- (6-hydroxyhexy
  • the compound having a photo-alignable group and a carboxyl group as the component (A) include cinnamic acid, ferulic acid, 4-methoxycinnamic acid, 3,4-dimethoxy cinnamic acid, coumarin-3- Carboxylic acid, 4- (N, N-dimethylamino) cinnamic acid and the like can be mentioned.
  • Specific examples of the compound having a photo-alignable group and an amino group as the component (A) include 4-aminocinnamic acid methyl ester, 4-amino cinnamic acid ethyl ester, 3-amino cinnamic acid methyl ester, Examples thereof include 3-aminocinnamic acid ethyl ester.
  • Specific examples of the compound (A) having a photo-alignment group and an alkoxysilyl group include 4- (3-trimethoxysilylpropyloxy) cinnamic acid methyl ester, 4- (3-triethoxysilyl) Propyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylpropyloxy) cinnamic acid ethyl ester, 4- (3-triethoxysilylpropyloxy) cinnamic acid ethyl ester, 4- (3-trimethoxy Silylhexyloxy) cinnamic acid methyl ester, 4- (3-triethoxysilylhexyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylhexyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylhexyloxy) cinnamic acid methyl ester,
  • low molecular weight photo-alignment component as component (A) can include the above-mentioned specific examples, but are not limited thereto.
  • the low molecular photoalignment component as the component (A) is particularly preferably a compound having a photoalignment group and a hydroxy group.
  • the compound having a photo-alignment group and a hydroxy group imparts photo-alignment to a cured film using the cured film-forming composition of the present invention, and adheres to a polymerizable liquid crystal layer when used as an alignment material. This is particularly effective in improving the property.
  • the low molecular photoalignment component as the component (A) is a compound having a photoalignment group and a hydroxy group
  • the component (A) two or more photoalignment groups are present in the molecule and / or A compound having two or more hydroxy groups can be used.
  • a compound having two or more photo-alignable groups and two hydroxyl groups in the molecule can be used.
  • compounds having two or more photoalignable groups and hydroxy groups in the molecule can be exemplified by compounds represented by the following formulae.
  • the molecular weight of the low molecular photoalignment component as the component (A) is controlled to a value within a desired range. That is, in order to form the cured film of the present invention using the cured film forming composition of the present invention, heat curing is required, but when the heating is performed, the low molecular photo-alignment component which is the component (A) Can be suppressed from sublimation.
  • the compound of the component (A) in the cured film forming composition of the present invention at least one substituent selected from a photo-alignment group and any of a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group. And a mixture of a plurality of types of compounds.
  • the component (B) is a polymer (hereinafter also referred to as a specific (co) polymer) having a substituent capable of thermally reacting with the component (A) and capable of self-crosslinking.
  • the component (B) is capable of causing a specific crosslinkable substituent, more specifically, a self-crosslinking reaction, and is thermally reacted with the component (A) at a temperature lower than the sublimation temperature of the component (A). It is a polymer having a crosslinkable substituent.
  • the component (B) undergoes a self-crosslinking reaction, reacts with the component (A) at a temperature lower than the sublimation temperature of the component (A) (thermal reaction), and (A) It can suppress that a component sublimates.
  • the cured film formation composition of this invention can form the orientation material with high photoreaction efficiency of a substituent as mentioned above as a cured film.
  • Preferred specific crosslinkable substituents contained in the polymer of component (B) include alkoxymethylamide groups such as (C 1-10 alkoxy) -CH 2 —NH—C ( ⁇ O) — groups, hydroxymethylamide groups, And trialkoxysilyl groups such as (C 1-5 alkoxy) 3 Si—X— group (wherein X represents a spacer such as C 1-10 alkylene or phenylene).
  • the content of the specific crosslinkable substituent is preferably 0.2 to 1 per repeating unit in the polymer of component (B). From the viewpoint of solvent resistance of the alignment material, 0.4 to More preferably, it is one.
  • the above-mentioned monomer having the specific crosslinkable substituent may be (co) polymerized.
  • a monomer having a specific crosslinkable substituent include N-alkoxymethyl (meth) acrylamide and (C 1-5 alkoxy) 3 Si—X-ester of (meth) acrylic acid (where X is as defined above). Represents the same meaning).
  • polymers obtained using N-alkoxymethyl (meth) acrylamide include N-hydroxymethyl (meth) acrylamide, N-methoxymethyl (meth) acrylamide, N-ethoxymethyl (meth) acrylamide, and N-butoxymethyl.
  • (Meth) acrylamide means both methacrylamide and acrylamide.
  • Examples of such a polymer include poly (N-butoxymethylacrylamide), a copolymer of N-butoxymethylacrylamide and styrene, a copolymer of N-hydroxymethylmethacrylamide and methylmethacrylate, and N-ethoxymethyl.
  • Examples include a copolymer of methacrylamide and benzyl methacrylate.
  • component (B) compounds having trialkoxysilyl groups, such as (meth) acrylic silane such as 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, etc.
  • (meth) acrylic silane such as 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, etc.
  • a (C 1-5 alkoxy) 3 Si—X-ester of acrylic acid (where X represents the same meaning as described above) is used as a monomer having a specific crosslinkable substituent, and optionally further co-polymerized with the monomer.
  • Polymers produced using polymerizable monomers see below can also be used.
  • Examples of such a polymer include poly (3-methacryloxypropyltrimethoxysilane), a copolymer of 3-methacryloxypropyltrimethoxysilane and styrene, poly (3-acryloxypropyltrimethoxysilane), 3 -A copolymer of acryloxypropyltrimethoxysilane and methyl methacrylate.
  • a monomer copolymerizable with a monomer having a specific crosslinkable substituent hereinafter referred to as non-crosslinkable substitution
  • Also referred to as a monomer having a group
  • the monomer having a non-crosslinkable substituent examples include acrylic ester compounds, methacrylic ester compounds, maleimide compounds, acrylamide compounds, methacrylamide compounds, acrylonitrile, styrene compounds and vinyl compounds.
  • acrylic ester compounds methacrylic ester compounds, maleimide compounds, acrylamide compounds, methacrylamide compounds, acrylonitrile, styrene compounds and vinyl compounds.
  • acrylic ester compound described above examples include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, glycidyl acrylate, 2,2,2-trifluoroethyl.
  • methacrylic acid ester compounds described above include methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, glycidyl methacrylate, 2,2,2-trifluoroethyl.
  • Examples of the vinyl compound described above include methyl vinyl ether, benzyl vinyl ether, vinyl naphthalene, vinyl carbazole, and 3-ethenyl-7-oxabicyclo [4.1.0] heptane.
  • styrene compound described above examples include styrene, methylstyrene, chlorostyrene, and bromostyrene.
  • maleimide compound described above examples include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
  • acrylamide compound described above examples include acrylamide, N-methylacrylamide, N-ethylacrylamide, N-benzylacrylamide, N-phenylacrylamide, and N, N-dimethylacrylamide.
  • methacrylamide compounds mentioned above include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, N, N-dimethyl methacrylamide and the like.
  • a monomer having a substituent selected from a hydroxy group, a carboxyl group and an amino group can also be used as a copolymerizable monomer of the component (B) as long as the effects of the present invention are not impaired.
  • the repeating unit derived from such a monomer is not included in the component (B), and even if it is included, the repeating unit in the polymer of the component (B) It is preferably less than 0.1 unit per unit.
  • the method for obtaining the polymer (B): specific (co) polymer used in the cured film forming composition of the present invention is not particularly limited.
  • the monomer having the specific crosslinkable substituent described above, and optionally non-crosslinkable It is obtained by carrying out a polymerization reaction at a temperature of 50 ° C. to 110 ° C. in a solvent in which a monomer having a substituent and a polymerization initiator coexist.
  • the solvent used will not be specifically limited if the monomer which has a specific crosslinkable substituent, the monomer which has a non-crosslinkable substituent used as needed, a polymerization initiator, etc. are melt
  • Specific examples include solvents described in Solvents described below.
  • the specific (co) polymer which is the polymer of the component (B) thus obtained is usually in a solution state dissolved in a solvent and can be used as it is as the solution of the component (B) in the present invention. .
  • the solution of the specific (co) polymer which is the polymer of the component (B) obtained as described above, is re-precipitated by stirring with stirring such as diethyl ether or water, and the generated precipitate is filtered.
  • powder of a specific (co) polymer can be obtained by drying at normal temperature or reduced pressure at room temperature or by heating. By such an operation, the polymerization initiator and unreacted monomer coexisting with the specific (co) polymer can be removed, and as a result, a purified specific (co) polymer powder can be obtained. If sufficient purification cannot be achieved by one operation, the obtained powder may be redissolved in a solvent and the above operation may be repeated.
  • the powder of the specific (co) polymer that is the polymer of the component (B) may be used as it is, or the powder is re-dissolved in, for example, a solvent described later. It may be used as a solution state.
  • the polymer of component (B) can be used alone or in combination of two or more, that is, it can be used in a mixture of a plurality of specific (co) polymers.
  • the polymer (B) has a weight average molecular weight of 1,000 to 500,000, preferably 1,000 to 200,000, more preferably 1,000 to 100,000. More preferably, it is 2,000 to 50,000.
  • the cured film forming composition of the present invention may contain a crosslinking catalyst as the component (C) as desired in addition to the components (A) and (B) described above.
  • crosslinking catalyst of a component an acid or a thermal acid generator is mentioned, for example.
  • This crosslinking catalyst as component (C) is effective in promoting the thermosetting reaction in the formation of a cured film using the cured film forming composition of the present invention.
  • the component (C) is a sulfonic acid group-containing compound, hydrochloric acid or a salt thereof, a compound that generates heat by pre-baking or post-baking to generate an acid, that is, a temperature of 80
  • the compound is not particularly limited as long as it is a compound which generates an acid by thermal decomposition at a temperature of from 250 to 250 ° C.
  • Examples of such compounds include hydrochloric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, pentanesulfonic acid, octanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, trifluoro.
  • L-methanesulfonic acid p-phenolsulfonic acid, 2-naphthalenesulfonic acid, mesitylenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 1H, 1H, 2H, 2H-perfluorooctanesulfonic acid, perfluoro (2-ethoxyethane) sulfonic acid, pentafluoroethanesulfonic acid, nonafluorobutane-1-sulfonic acid, sulfonic acid such as dodecylbenzenesulfonic acid, or a hydrate or salt thereof Is mentioned.
  • Examples of the compound that generates an acid by heat include bis (tosyloxy) ethane, bis (tosyloxy) propane, bis (tosyloxy) butane, p-nitrobenzyl tosylate, o-nitrobenzyl tosylate, 1,2, 3-phenylene tris (methyl sulfonate), p-toluenesulfonic acid pyridinium salt, p-toluenesulfonic acid morphonium salt, p-toluenesulfonic acid ethyl ester, p-toluenesulfonic acid propyl ester, p-toluenesulfonic acid butyl ester, p-toluenesulfonic acid isobutyl ester, p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid phenethyl ester, cyanomethyl p-
  • Content of (C) component in the cured film formation composition of this invention is 100 mass of the total amount of the compound which has the photo-alignment group which is (A) component, a hydroxyl group, etc., and the polymer of (B) component.
  • the amount is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 8 parts by mass, and still more preferably 0.1 to 6 parts by mass with respect to parts.
  • the cured film forming composition of the present invention can be used mainly in a solution state dissolved in a solvent.
  • the solvent used at that time is not particularly limited as long as it can dissolve the component (A) and the component (B) and, if necessary, the component (C) and other additives described later. .
  • the solvent include, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate , Propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butanone, 3-methyl-2-pentanone, 2-pentanone, 2-heptanone, ⁇ -butyrolactone, ethyl 2-hydroxypropionate, Ethyl 2-hydroxy-2-methylpropionate, ethoxy vinegar Ethyl, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate,
  • solvents can be used alone or in combination of two or more.
  • the cured film-forming composition of the present invention is a sensitizer, a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stability, if necessary, as long as the effects of the present invention are not impaired.
  • a sensitizer is effective in promoting a photoreaction after forming a thermosetting film using the cured film forming composition of the present invention.
  • sensitizers examples include benzophenone, anthracene, anthraquinone, thioxanthone, and derivatives thereof, and nitrophenyl compounds.
  • benzophenone derivatives and nitrophenyl compounds are preferred.
  • Specific examples of preferred compounds include N, N-diethylaminobenzophenone, 2-nitrofluorene, 2-nitrofluorenone, 5-nitroacenaphthene, 4-nitrobiphenyl, 4-nitrocinnamic acid, 4-nitrostilbene, 4-nitrobenzophenone. , 5-nitroindole and the like.
  • N, N-diethylaminobenzophenone which is a derivative of benzophenone is preferable.
  • sensitizers are not limited to those described above.
  • the sensitizers can be used alone or in combination of two or more compounds.
  • the proportion of the sensitizer used in the cured film forming composition of the present invention is as follows: the compound (A) having a photo-alignment group and a hydroxy group, and the (B) component specific (co) polymer.
  • the total mass is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass with respect to 100 parts by mass of the total mass. If this ratio is too small, the effect as a sensitizer may not be sufficiently obtained. If it is too large, the transmittance may be lowered and the coating film may be roughened.
  • the cured film forming composition of the present invention comprises a low molecular photo-alignment component that is component (A), a polymer that has a substituent that can be thermally reacted with component (A) that is component (B) and is capable of self-crosslinking. Is dissolved in a solvent. Furthermore, the cured film forming composition of this invention can contain a crosslinking catalyst as (C) component. And as long as the effect of this invention is not impaired, another additive can be contained.
  • the blending ratio (content ratio) of the component (A) and the component (B) is preferably 5:95 to 60:40 by mass ratio.
  • content ratio content ratio
  • the content of the component (B) is excessive, the liquid crystal orientation is liable to be lowered, and when it is too small, the solvent resistance is lowered and the orientation is liable to be lowered.
  • Preferred examples of the cured film forming composition of the present invention are as follows. [1]: The composition ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass ratio, and a cured film forming composition containing a solvent in addition to the components (A) and (B) object. [2]: The mixing ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass ratio, and is based on 100 parts by mass of the total amount of the components (A) and (B). A cured film forming composition containing 0.01 to 10 parts by mass of component (C) and a solvent.
  • the blending ratio, preparation method, and the like when the cured film forming composition of the present invention is used as a solution are described in detail below.
  • the ratio of the solid content in the cured film forming composition of the present invention is not particularly limited as long as each component is uniformly dissolved in the solvent, but it is 1% by mass to 80% by mass, preferably 3%.
  • the mass is from 60% by mass to 60% by mass, and more preferably from 5% by mass to 40% by mass.
  • solid content means what remove
  • the method for preparing the cured film forming composition of the present invention is not particularly limited.
  • a preparation method for example, a method of mixing the component (B) dissolved in the solvent with the component (A) and further the component (C) at a predetermined ratio as required to obtain a uniform solution, or this preparation In an appropriate stage of the method, there may be mentioned a method in which other additives are further added and mixed as necessary.
  • a solution of a specific (co) polymer (component (B)) obtained by a polymerization reaction in a solvent can be used as it is.
  • components (A) and (C) are added to a solution of component (B) obtained by polymerizing N-butoxymethylacrylamide in the same manner as described above to obtain a uniform solution.
  • a solvent may be further added for the purpose of adjusting the concentration.
  • the solvent used in the production process of the component (B) and the solvent used for adjusting the concentration of the cured film forming composition may be the same or different.
  • the prepared cured film-forming composition solution is preferably used after being filtered using a filter having a pore size of about 0.2 ⁇ m.
  • the solution is applied to a substrate (for example, a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, or a quartz substrate.
  • a substrate for example, a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, or a quartz substrate.
  • a cured film can be formed by coating by slit coating, spin coating following the slit, inkjet coating, printing, or the like to form a coating film, followed by heat drying with a hot plate or oven.
  • TAC triacetyl cellulose
  • cycloolefin polymer film polyethylene terephthalate film
  • resin film such as acrylic film
  • bar coating spin coating
  • flow coating roll coating
  • a cured film can be formed by coating by slit coating, spin coating following the slit, inkjet coating, printing, or the like to form a coating film, followed by heat drying with a hot plate or oven.
  • a heating temperature and a heating time appropriately selected from the range of a temperature of 60 ° C. to 200 ° C. and a time of 0.4 minutes to 60 minutes are adopted.
  • the heating temperature and the heating time are preferably 70 to 160 ° C. and 0.5 to 10 minutes.
  • the film thickness of the cured film formed using the cured film-forming composition of the present invention is, for example, 0.05 ⁇ m to 5 ⁇ m, and is appropriately selected in consideration of the level difference of the substrate to be used and optical and electrical properties. Can do.
  • the cured film thus produced can function as an alignment material, that is, a member for aligning a liquid crystal compound such as polymerizable liquid crystal by performing polarized UV irradiation.
  • ultraviolet light to visible light having a wavelength of 150 nm to 450 nm is usually used, and it is performed by irradiating linearly polarized light from a vertical or oblique direction at room temperature or in a heated state.
  • the alignment material formed from the cured film composition of the present invention has solvent resistance and heat resistance
  • a phase difference material composed of a polymerizable liquid crystal solution is applied onto the alignment material, and then the liquid crystal By heating to the phase transition temperature, the phase difference material is brought into a liquid crystal state and is aligned on the alignment material. Then, the retardation material in an oriented state can be cured as it is to form a retardation material as a layer having optical anisotropy.
  • the retardation material for example, a liquid crystal monomer having a polymerizable group and a composition containing the same are used.
  • substrate which forms an orientation material is a film
  • the film which has the phase difference material of this invention is useful as a phase difference film.
  • the phase difference material that forms such a phase difference material is in a liquid crystal state and has an alignment state such as horizontal alignment, cholesteric alignment, vertical alignment, hybrid alignment, etc. on the alignment material. It can be used properly according to the phase difference characteristics.
  • standard is passed through the mask of a line and space pattern to the cured film formed by said method from the cured film composition of this invention. Then, for example, polarized UV exposure was performed in the direction of +45 degrees, and then the polarized UV was exposed in the direction of ⁇ 45 degrees after removing the mask, and two types of liquid crystal alignment regions having different liquid crystal alignment control directions were formed. An alignment material is obtained. Thereafter, after applying a retardation material composed of a polymerizable liquid crystal solution, the retardation material is brought into a liquid crystal state by heating to a phase transition temperature of the liquid crystal.
  • the polymerizable liquid crystal in a liquid crystal state is aligned on an alignment material on which two types of liquid crystal alignment regions are formed, and forms an alignment state corresponding to each liquid crystal alignment region. Then, the retardation material realized by such an orientation state is cured as it is, the above-described orientation state is fixed, and a plurality of two kinds of retardation regions having different retardation characteristics are regularly arranged, A patterned retardation material can be obtained.
  • the alignment materials on both substrates are bonded to each other via a spacer, and then between the substrates.
  • a liquid crystal display element in which liquid crystal is injected to align the liquid crystal may be used. Therefore, the cured film forming composition of this invention can be used suitably for manufacture of various retardation materials (retardation film), a liquid crystal display element, etc.
  • the number average molecular weight and weight average molecular weight of the acrylic copolymer obtained in accordance with the following synthesis examples were measured using a GPC apparatus (Shodex (registered trademark) columns KF803L and KF804L) manufactured by JASCO Corporation, and the elution solvent tetrahydrofuran at a flow rate of 1 mL. It was measured under the condition that the column was eluted at a rate of 40 minutes per minute (column temperature: 40 ° C.).
  • Mn number average molecular weight
  • Mw weight average molecular weight
  • the reaction system was poured into 2 L of ethyl acetate and extracted with 1N-hydrochloric acid aqueous solution and saturated brine.
  • anhydrous magnesium sulfate was added, dehydrated and dried, and anhydrous magnesium sulfate was filtered.
  • the obtained filtrate was evaporated using a rotary evaporator to obtain 109.4 g of the desired product CIN11-1 (red brown viscous body).
  • the obtained CIN11-1 was used in the next reaction without purification.
  • Examples 1 to 7 The cured film forming compositions of Examples 1 to 7 were prepared with the compositions shown in Table 1, and the orientation sensitivity, pattern formability, and transmittance were evaluated for each.
  • This film was exposed at 300 mJ / cm 2 to prepare a retardation material.
  • the retardation material on the produced substrate is sandwiched between a pair of polarizing plates, the state of development of retardation characteristics in the retardation material is observed, and the exposure amount of polarized UV necessary for the alignment material to exhibit liquid crystal alignment (mJ / cm 2 ) was evaluated as the orientation sensitivity (maximum polarized UV exposure amount: 50 mJ / cm 2 ).
  • a polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Co., Ltd. was applied using a spin coater, and then pre-baked on a hot plate at 60 ° C. for 60 seconds to form a film.
  • a coating film having a thickness of 1.0 ⁇ m was formed.
  • the coating film on this substrate was exposed at 300 mJ / cm 2 to prepare a patterned retardation material.
  • the patterned phase difference material on the produced substrate was observed using a polarizing microscope, and evaluation was made with ⁇ indicating that the phase difference pattern was formed without alignment defects, and ⁇ indicating that the alignment defects were observed.
  • Examples 1 to 7 all showed liquid crystal alignment with a small exposure amount of 10 to 20 mJ / cm 2 , that is, had high alignment sensitivity and could be subjected to optical patterning. Furthermore, it showed high transparency.
  • Comparative Examples 1 and 2 which do not use a compound having a specific crosslinkable substituent and Comparative Example 3 which has a specific crosslinkable substituent but is a low molecular weight compound are all liquid crystal alignment at an exposure amount of 50 mJ / cm 2. In other words, the alignment sensitivity was very low, and it was difficult to perform optical patterning.
  • the cured film forming composition according to the present invention is very useful as an alignment material for forming a liquid crystal alignment film of a liquid crystal display element and an optically anisotropic film provided inside or outside the liquid crystal display element, It is suitable as a material for forming a patterned retardation material for 3D display. Further, a material for forming a cured film such as a protective film, a planarizing film and an insulating film in various displays such as a thin film transistor (TFT) type liquid crystal display element and an organic EL element, in particular, an interlayer insulating film and a color filter of the TFT type liquid crystal element It is also suitable as a material for forming a protective film or an insulating film of an organic EL element.
  • TFT thin film transistor

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Abstract

La présente invention concerne une composition pour former un film durci avec lequel on forme un film durci présentant d'excellentes propriétés d'efficacité photoréactive et de résistance aux solvants, et concerne un matériau à orientation destiné à la photo-orientation et un matériau à différence de phase formé au moyen du matériau à orientation. La présente invention concerne une composition pour former un film durci comprenant (A) un composé comprenant des groupes capables de photo-orientation et au moins un type de groupe de substitution choisi parmi les groupes hydroxyle, carboxyle, amino et alcoxysilyle, et (B) un composé auto-réticulable possédant des groupes de substitution capables de réagir thermiquement avec le composant (A). Un film durci est formé au moyen de la composition pour former un film durci, et un matériau à orientation est formé au moyen de la technologie de photo-orientation. Un cristal liquide polymérisable est appliqué sur le matériau à orientation et durci pour obtenir un matériau à différence de phase.
PCT/JP2013/085165 2012-12-27 2013-12-27 Composition pour former un film durci, matériau à orientation et matériau à différence de phase Ceased WO2014104320A1 (fr)

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KR1020157018928A KR102182361B1 (ko) 2012-12-27 2013-12-27 경화막 형성 조성물, 배향재 및 위상차재
JP2014554603A JP6372022B2 (ja) 2012-12-27 2013-12-27 硬化膜形成組成物、配向材および位相差材
CN201380068435.3A CN104903405B (zh) 2012-12-27 2013-12-27 固化膜形成用组合物、取向材及相位差材

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015030000A1 (fr) * 2013-08-27 2015-03-05 日産化学工業株式会社 Composition permettant de former un film durci, matériau d'alignement, et matériau à différence de phase
KR20160121525A (ko) 2014-02-13 2016-10-19 다이니폰 인사츠 가부시키가이샤 광 배향성을 갖는 열 경화성 조성물, 배향층, 배향층 딸린 기판, 위상차판 및 디바이스
KR20160123297A (ko) 2014-02-13 2016-10-25 다이니폰 인사츠 가부시키가이샤 광 배향성을 갖는 열 경화성 조성물, 배향층, 배향층 딸린 기판, 위상차판 및 디바이스
WO2024162344A1 (fr) * 2023-01-31 2024-08-08 日産化学株式会社 Composition polymère et matériau de retard monocouche

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110461965A (zh) * 2017-03-27 2019-11-15 日产化学株式会社 固化膜形成用组合物、取向材及相位差材

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121407A (ja) * 2000-10-17 2002-04-23 Asahi Glass Co Ltd 硬化性組成物
JP2003222868A (ja) * 2002-01-31 2003-08-08 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
JP2007121721A (ja) * 2005-10-28 2007-05-17 Dainippon Ink & Chem Inc 光配向膜用組成物、光配向膜の製造方法、及びこれを用いた光学異方体、光学素子、その製造方法
JP2007256744A (ja) * 2006-03-24 2007-10-04 Kri Inc ポリシラザン組成物および該組成物を用いた光学フィルム、ならびに光学フィルムの製造方法
JP2009258650A (ja) * 2008-03-25 2009-11-05 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
JP2009282341A (ja) * 2008-05-23 2009-12-03 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
WO2011010635A1 (fr) * 2009-07-21 2011-01-27 日産化学工業株式会社 Composition formant un film durci à chaud ayant une propriété de photo-alignement
WO2011126021A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film thermo-durci ayant des propriétés de photo-alignement
WO2011126022A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film durci à la chaleur doté de propriétés de photo-alignement
WO2011126019A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film thermodurci ayant des propriétés de photoalignement
WO2012018121A1 (fr) * 2010-08-05 2012-02-09 日産化学工業株式会社 Composition de résine, agent d'orientation de cristaux liquides et agent de différence de phase
WO2013054784A1 (fr) * 2011-10-11 2013-04-18 日産化学工業株式会社 Composition formant un film durci, matériau d'orientation, et matériau de déphasage
WO2013146469A1 (fr) * 2012-03-28 2013-10-03 日産化学工業株式会社 Composition de formation d'un film durci, matière d'orientation et matière de déphasage
WO2014010688A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composition de formation de film durci, matière d'alignement et matière de déphasage
JP2014012823A (ja) * 2012-06-06 2014-01-23 Jnc Corp 光配向性基を有する高分子組成物、該高分子組成物から作製される液晶配向膜及び該液晶配向膜から作製される位相差板を備えた光デバイス

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS611342A (ja) 1984-06-14 1986-01-07 Noboru Yamada 製燻法
JP3767962B2 (ja) 1997-02-19 2006-04-19 シャープ株式会社 映像表示システム
KR100574190B1 (ko) 1997-09-25 2006-04-27 롤리크 아게 광 가교결합성 폴리이미드, 이를 사용한 배향층의 제조방법 및 당해 배향층을 갖는 광학장치 또는 전기 광학장치
JP2005049865A (ja) 2003-07-17 2005-02-24 Arisawa Mfg Co Ltd 光学位相差素子の製造方法
EP2182407A4 (fr) * 2007-08-21 2011-03-23 Jsr Corp Agent d'alignement de cristaux liquides, procédé de fabrication d'un film d'alignement de cristaux liquides, et dispositif d'affichage à cristaux liquides
JP5316740B2 (ja) 2007-08-30 2013-10-16 Ｊｓｒ株式会社 液晶配向膜の形成方法

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002121407A (ja) * 2000-10-17 2002-04-23 Asahi Glass Co Ltd 硬化性組成物
JP2003222868A (ja) * 2002-01-31 2003-08-08 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
JP2007121721A (ja) * 2005-10-28 2007-05-17 Dainippon Ink & Chem Inc 光配向膜用組成物、光配向膜の製造方法、及びこれを用いた光学異方体、光学素子、その製造方法
JP2007256744A (ja) * 2006-03-24 2007-10-04 Kri Inc ポリシラザン組成物および該組成物を用いた光学フィルム、ならびに光学フィルムの製造方法
JP2009258650A (ja) * 2008-03-25 2009-11-05 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
JP2009282341A (ja) * 2008-05-23 2009-12-03 Jsr Corp 液晶配向剤、液晶配向膜の形成方法および液晶表示素子
WO2011010635A1 (fr) * 2009-07-21 2011-01-27 日産化学工業株式会社 Composition formant un film durci à chaud ayant une propriété de photo-alignement
WO2011126021A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film thermo-durci ayant des propriétés de photo-alignement
WO2011126022A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film durci à la chaleur doté de propriétés de photo-alignement
WO2011126019A1 (fr) * 2010-04-08 2011-10-13 日産化学工業株式会社 Composition formant un film thermodurci ayant des propriétés de photoalignement
WO2012018121A1 (fr) * 2010-08-05 2012-02-09 日産化学工業株式会社 Composition de résine, agent d'orientation de cristaux liquides et agent de différence de phase
WO2013054784A1 (fr) * 2011-10-11 2013-04-18 日産化学工業株式会社 Composition formant un film durci, matériau d'orientation, et matériau de déphasage
WO2013146469A1 (fr) * 2012-03-28 2013-10-03 日産化学工業株式会社 Composition de formation d'un film durci, matière d'orientation et matière de déphasage
JP2014012823A (ja) * 2012-06-06 2014-01-23 Jnc Corp 光配向性基を有する高分子組成物、該高分子組成物から作製される液晶配向膜及び該液晶配向膜から作製される位相差板を備えた光デバイス
WO2014010688A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composition de formation de film durci, matière d'alignement et matière de déphasage

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015030000A1 (fr) * 2013-08-27 2015-03-05 日産化学工業株式会社 Composition permettant de former un film durci, matériau d'alignement, et matériau à différence de phase
KR20160121525A (ko) 2014-02-13 2016-10-19 다이니폰 인사츠 가부시키가이샤 광 배향성을 갖는 열 경화성 조성물, 배향층, 배향층 딸린 기판, 위상차판 및 디바이스
KR20160123297A (ko) 2014-02-13 2016-10-25 다이니폰 인사츠 가부시키가이샤 광 배향성을 갖는 열 경화성 조성물, 배향층, 배향층 딸린 기판, 위상차판 및 디바이스
US10017696B2 (en) 2014-02-13 2018-07-10 Dai Nippon Printing Co., Ltd. Thermosetting composition with photo-alignment property, alignment layer, substrate with alignment layer, retardation plate, and device
US10017697B2 (en) 2014-02-13 2018-07-10 Dai Nippon Printing Co., Ltd. Thermosetting composition with photo-alignment property, alignment layer, substrate with alignment layer, retardation plate, and device
WO2024162344A1 (fr) * 2023-01-31 2024-08-08 日産化学株式会社 Composition polymère et matériau de retard monocouche

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CN104903405B (zh) 2017-11-10
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