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WO2014171376A1 - Composition formant un film durci, matériau d'orientation et matériau de déphasage - Google Patents

Composition formant un film durci, matériau d'orientation et matériau de déphasage Download PDF

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Publication number
WO2014171376A1
WO2014171376A1 PCT/JP2014/060297 JP2014060297W WO2014171376A1 WO 2014171376 A1 WO2014171376 A1 WO 2014171376A1 JP 2014060297 W JP2014060297 W JP 2014060297W WO 2014171376 A1 WO2014171376 A1 WO 2014171376A1
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WIPO (PCT)
Prior art keywords
component
group
cured film
forming composition
alignment
Prior art date
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PCT/JP2014/060297
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English (en)
Japanese (ja)
Inventor
真 畑中
石田　智久
昇志郎 湯川
耕平 後藤
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Nissan Chemical Corp
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Nissan Chemical Corp
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Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to KR1020157031137A priority Critical patent/KR102165703B1/ko
Priority to CN201480031811.6A priority patent/CN105283512B/zh
Priority to JP2015512455A priority patent/JP6458949B2/ja
Publication of WO2014171376A1 publication Critical patent/WO2014171376A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • 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
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
    • 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

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 plurality of two types of retardation regions having different retardation characteristics are regularly arranged, thereby forming a patterned retardation material.
  • 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 (see Patent Documents 3 to 5).
  • acrylic resins having photodimerization sites such as cinnamoyl groups and chalcone groups in such side chains do not provide sufficient characteristics when applied to the formation of retardation materials. ing.
  • 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 100 mJ / cm 2 ) sufficient to align the liquid crystal for a normal liquid crystal panel.
  • the reason why the amount of polarized UV exposure increases is that, in the case of forming a retardation material, different from the liquid crystal for liquid crystal panels, a polymerizable liquid crystal is used in a solution state and applied onto an alignment material.
  • 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, the acrylic resin is subjected to photocrosslinking by a photodimerization reaction. . And it is necessary to continue the irradiation of polarized light with a large exposure amount until resistance to the polymerizable liquid crystal solution is developed.
  • 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 one or more substituents selected from a hydroxy group, a carboxyl group, a trialkoxysilyl group, and an amino group, (B) a hydrophilic polymer having one or more substituents selected from a hydroxy group, a carboxyl group and an amino group;
  • the present invention relates to a cured film-forming composition comprising (C) a compound having two or more trialkoxysilyl groups and (D) a crosslinking catalyst.
  • 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 a cinnamoyl group.
  • the photoalignable group of the component (A) is a group having an azobenzene structure.
  • the compound of component (A) has two or more hydroxy groups.
  • the component (B) is preferably at least one hydrophilic polymer selected from the group consisting of polyether polyol, polyester polyol, polycarbonate polyol and polycaprolactone polyol.
  • the component (B) is preferably cellulose or a derivative thereof.
  • the component (B) is at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms, and at least one of a carboxyl group and a phenolic hydroxy group. It is preferable that it is an acrylic polymer which has.
  • the component (B) includes at least one of a monomer having a polyethylene glycol ester group and a monomer having a hydroxyalkyl ester group having 2 to 5 carbon atoms, a monomer having a carboxyl group, and An acrylic copolymer obtained by a polymerization reaction of a monomer containing at least one of monomers having a phenolic hydroxy group is preferable.
  • the component (B) is preferably cyclodextrin or a derivative thereof.
  • the component (D) is preferably an acid or a thermal acid generator.
  • the ratio of the component (A) to the component (B) is preferably 5:95 to 65:35 by mass ratio.
  • component (C) it is preferable to contain 10 to 100 parts by mass of component (C) based on 100 parts by mass of the total amount of components (A) and (B).
  • WHEREIN It is preferable to contain (D) component of 0.5 mass part thru
  • the second aspect of the present invention relates to an alignment material characterized by being made from the thermosetting film forming composition of the first aspect of the present invention.
  • 3rd aspect of this invention is related with the phase difference material formed using the cured film obtained from the cured film formation composition of the 1st aspect of this 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. can do.
  • 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.
  • the third aspect of the present invention it is possible to provide a retardation material that can be formed with high efficiency and can be subjected to optical patterning.
  • the cured film forming composition of the present embodiment includes (A) a low molecular photo-alignment component, (B) a hydrophilic polymer as a component, and a compound having two or more trialkoxysilyl groups as a component (C), And (D) a crosslinking catalyst as a component.
  • the cured film forming composition of the present embodiment contains other additives as long as the effects of the present invention are not impaired. Can be contained.
  • (A) component contained in the cured film forming composition of this Embodiment is 1 type, or 2 or more types of substitution chosen from a photo-alignment group and a hydroxy group, a carboxyl group, a trialkoxysilyl group, and an amino group And a compound having a group.
  • the photoalignable group reacts with light to form a hydrophobic photoalignment portion, while the substituent selected from a carboxyl group, trialkoxysilyl group and amino group is hydrophilic.
  • the thermal reaction part is configured. That is, the component (A) is a component that imparts photoalignment to the cured film, and the component (A) is also referred to as a photoalignment component or a low molecular photoalignment component in the present specification.
  • the photo-alignment group means a functional group at a structural site that undergoes photodimerization or photoisomerization.
  • the structural site to be photodimerized is a site that forms a dimer by light irradiation, and specific examples thereof include a cinnamoyl group, a chalcone group, a coumarin group, and an anthracene group. Among these, a cinnamoyl group having high transparency in the visible light region and photodimerization reactivity is preferable.
  • the structural site that undergoes photoisomerization refers to a structural site that changes into a cis form and a trans form upon irradiation with light, and specific examples thereof include a site comprising an azobenzene structure, a stilbene structure, or the like.
  • an azobenzene structure is preferred because of its high reactivity.
  • the compound having a photo-alignment group and a hydroxy group is represented by the following formula, for example. Specific examples of such a compound are shown in the following formulas [A1] to [A5].
  • X 1 has 1 to 18 carbon atoms via one or more bonds selected from a single bond, an ether bond, an ester bond, an amide bond, a urethane bond, an amino bond, or a combination thereof. It represents a structure in which 1 to 3 substituents selected from an alkyl group, a phenyl group, a biphenyl group, or a combination thereof are bonded.
  • X 2 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.
  • the alkyl group having 1 to 18 carbon atoms, the phenyl group, the biphenyl group, and the cyclohexyl group may be bonded through a covalent bond, an ether bond, an ester bond, an amide bond, or a urea bond.
  • X 3 represents a hydroxy group, a phenyl group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxy group.
  • X 4 each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, an aromatic ring group, or an aliphatic ring group.
  • the alkylene group having 1 to 20 carbon atoms may be branched or linear.
  • X 5 represents a hydroxy group, a carboxyl group, an amino group or an alkoxysilyl group.
  • X represents a single bond, an oxygen atom or a sulfur atom.
  • the phenyl group and the biphenyl group are the same or selected from 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 more different substituents.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom. Represents an alkoxy group, a halogen atom, a trifluoromethyl group, or a cyano group. Further, in the above formula, A 1 represents a hydrogen atom or a methyl group. A2 represents a hydrogen atom or a methyl group.
  • the (A) component compound having a photoalignable group and a hydroxy group include, for example, 4- (8-hydroxyoctyloxy) cinnamic acid methyl ester, 4- (6-hydroxyhexyloxy) silicic acid.
  • the compound having a photo-alignment group and a carboxyl group include cinnamic acid, ferulic acid, 4-nitrocinnamic acid, 4-methoxy cinnamic 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-alignment group and a carboxyl group and an amino group include methyl-4-aminocinnamic acid, ethyl-4-aminocinnamic acid, methyl-3-aminocinnamic acid, ethyl-3- Examples include aminocinnamic acid.
  • Specific examples of the compound having a photo-alignable group and an amino group as 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 a trialkoxysilyl group include 4- (3-trimethoxysilylpropyloxy) cinnamic acid methyl ester, 4- (3-triethoxy Silylpropyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylpropyloxy) cinnamic acid ethyl ester, 4- (3-triethoxysilylpropyloxy) cinnamic acid ethyl ester, 4- (3-tri Methoxysilylhexyloxy) cinnamic acid methyl ester, 4- (3-triethoxysilylhexyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylhexyloxy) cinnamic acid ethyl ester and 4- (3- And triethoxysilylhexyloxy) cinnamic acid
  • low molecular photo-alignment component (A) component are not limited to these.
  • the photo-alignment component as the component (A) is a compound having a photo-alignment group and a hydroxy group
  • the component (A) two or more photo-alignment groups and / or hydroxy are present in the molecule. It is possible to use compounds having two or more groups.
  • a compound having two or more photo-alignable groups and two hydroxyl groups in the molecule can be used.
  • a compound represented by the following formula can be shown as an example of a compound having two or more photoalignable groups and hydroxy groups in the molecule.
  • the photo-alignment component (A) it is possible to control to increase the molecular weight of the photo-alignment component as the component (A).
  • the photo-alignment component (A) and the polymer (B) component and the cross-linking agent (C) are thermally reacted, the photo-alignment component (A) It can suppress that a component sublimates.
  • the cured film formation composition of this Embodiment can form alignment material with high photoreaction efficiency as a cured film.
  • a compound of (A) component in the cured film formation composition of this Embodiment it has multiple types which have a photo-alignment group and any one substituent chosen from a hydroxyl group, a carboxyl group, and an amino group. A mixture of these compounds may also be used.
  • the component (B) contained in the cured film forming composition of the present embodiment is a hydrophilic polymer.
  • the hydrophilic polymer as the component (B) is a polymer having one or more substituents selected from a hydroxy group, a carboxyl group and an amino group (hereinafter also referred to as a specific polymer). it can.
  • a specific polymer selection of a highly hydrophilic polymer having high hydrophilicity so as to be more hydrophilic than the compound of the component (A) Is preferred.
  • a specific polymer is a polymer which has hydrophilic groups, such as a hydroxyl group, a carboxyl group, and an amino group, Specifically, 1 type or 2 types chosen from a hydroxy group, a carboxyl group, and an amino group A polymer having the above substituents is preferred. That is, “hydrophilicity” in the hydrophilic polymer of the component (B) in the present specification means that it is more hydrophilic than the compound of the component (A).
  • hydrophilic polymer (B) examples include acrylic polymer, polyamic acid, polyimide, polyvinyl alcohol, polyester, polyester polycarboxylic acid, polyether polyol, polyester polyol, polycarbonate polyol, polycaprolactone polyol, and polyalkyleneimine.
  • Polymers having linear or branched structures such as polyallylamine, celluloses (cellulose or derivatives thereof), phenol novolac resins, melamine formaldehyde resins, and cyclic polymers such as cyclodextrins.
  • acrylic polymer a polymer obtained by polymerizing a monomer having an unsaturated double bond such as acrylic acid ester, methacrylic acid ester, and styrene can be applied.
  • the specific polymer as component (B) is preferably at least one of hydroxyalkylcyclodextrins, celluloses, polyethylene glycol ester groups and hydroxyalkyl ester groups having 2 to 5 carbon atoms, a carboxyl group, and An acrylic polymer having at least one of phenolic hydroxy groups, an acrylic polymer having an aminoalkyl group in the side chain, a polyether polyol, a polyester polyol, a polycarbonate polyol, and a polycaprolactone polyol.
  • (B) It is a preferred example of the specific polymer of the component, and has at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms, and at least one of a carboxyl group and a phenolic hydroxy group.
  • the acrylic polymer may be an acrylic polymer having such a structure, and is not particularly limited with respect to the main chain skeleton and side chain type of the polymer constituting the acrylic polymer.
  • a preferred structural unit As a structural unit having at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms, a preferred structural unit is represented by the following formula [B1]. As a structural unit having at least one of a carboxyl group and a phenolic hydroxy group, a preferred structural unit is represented by the following formula [B2].
  • X 11 and X 12 each independently represent a hydrogen atom or a methyl group
  • Y 1 represents an H— (OCH 2 CH 2 ) n — group (where n The value is 2 to 50, preferably 2 to 10.) or a hydroxyalkyl group having 2 to 5 carbon atoms
  • Y 2 represents a carboxyl group or a phenolic hydroxy group.
  • the acrylic polymer as an example of the component (B) preferably has a weight average molecular weight of 3,000 to 200,000, more preferably 4,000 to 150,000, and 5,000 to 100,000. More preferably, it is 000. If the weight average molecular weight is over 200,000, the solubility in the solvent may be reduced and the handling property may be reduced. If the weight average molecular weight is less than 3,000, When cured, it may become insufficiently cured and solvent resistance and heat resistance may decrease.
  • the weight average molecular weight is a value obtained by using gel as a standard sample by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • a monomer having at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms (hereinafter also referred to as b1 monomer) is used.
  • a method of copolymerizing a monomer having at least one of a carboxyl group and a phenolic hydroxy group (hereinafter also referred to as b2 monomer) is simple.
  • Examples of the monomer having a polyethylene glycol ester group described above include monoacrylate or monomethacrylate of H— (OCH 2 CH 2 ) n —OH.
  • the value of n is 2 to 50, preferably 2 to 10.
  • Examples of the monomer having a hydroxyalkyl ester group having 2 to 5 carbon atoms include 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, and 4-hydroxybutyl acrylate. 4-hydroxybutyl methacrylate.
  • Examples of the monomer having a carboxyl group described above include acrylic acid, methacrylic acid, and vinyl benzoic acid.
  • Examples of the above-described monomer having a phenolic hydroxy group include p-hydroxystyrene, m-hydroxystyrene, and o-hydroxystyrene.
  • a monomer other than the b1 monomer and the b2 monomer, specifically a hydroxy group when synthesizing an acrylic polymer as an example of the component (B), a monomer other than the b1 monomer and the b2 monomer, specifically a hydroxy group, unless the effects of the present invention are impaired. And a monomer having neither of the carboxyl groups can be used in combination.
  • Examples of such a monomer include acrylic acid ester compounds such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl methacrylate, butyl acrylate, isobutyl acrylate, and t-butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, Methacrylic acid ester compounds such as isopropyl methacrylate, isobutyl methacrylate, t-butyl methacrylate, maleimide compounds such as maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide, acrylamide compounds, acrylonitrile, maleic anhydride, styrene Examples thereof include compounds and vinyl compounds.
  • acrylic acid ester compounds such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl
  • the amount of the b1 monomer and b2 monomer used to obtain the acrylic polymer which is an example of the component (B) is based on the total amount of all monomers used to obtain the acrylic polymer which is the component (B). It is preferable that the monomer is 2 mol% to 95 mol% and the b2 monomer is 5 mol% to 98 mol%.
  • the b1 monomer is 60 mol% to 95 mol% and the b2 monomer is based on the total amount of all monomers used to obtain the acrylic polymer as the component (B). 5 mol% to 40 mol% is preferable.
  • the b1 monomer is 2 mol% to 80 mol% and the b2 monomer is 20 mol% to 98 mol%.
  • the method to obtain the acrylic polymer which is an example of a component is not specifically limited,
  • the solvent which coexisted the monomer other than b1 monomer and b2 monomer with the monomer other than b1 monomer and the polymerization initiator etc. if desired
  • the acrylic polymer is obtained by a polymerization reaction at a temperature of 50 ° C. to 110 ° C.
  • the solvent used is not particularly limited as long as it dissolves the b1 monomer and the b2 monomer, the monomer other than the b1 monomer and the b2 monomer used as desired, a polymerization initiator, and the like. Specific examples are described in the ⁇ Solvent> section below.
  • the acrylic polymer having an aminoalkyl group in the side chain which is a preferred example of the specific polymer of component (B), includes aminoalkyl ester monomers such as aminoethyl acrylate, aminoethyl methacrylate, aminopropyl acrylate, and aminopropyl methacrylate. What polymerized or what copolymerized the said aminoalkyl ester monomer and 1 type, or 2 or more types of monomers chosen from said acrylic monomer are mentioned.
  • the acrylic polymer as an example of the component (B) obtained by the above method is usually in a solution state dissolved in a solvent.
  • the acrylic polymer solution which is an example of the component (B) obtained by the above method, is poured into diethyl ether or water under stirring to cause reprecipitation, and the generated precipitate is filtered and washed. Under normal pressure or reduced pressure, it can be dried at room temperature or dried to obtain an acrylic polymer powder as an example of the component (B).
  • the polymerization initiator and unreacted monomer coexisting with the acrylic polymer as an example of the component (B) can be removed.
  • the purified acrylic polymer as an example of the component (B) A powder is obtained. If sufficient purification cannot be achieved by a single operation, the obtained powder may be redissolved in a solvent and the above operation may be repeated.
  • Polyether polyol which is a preferred example of the specific polymer of component is polyethylene glycol, polypropylene glycol, propylene glycol, bisphenol A, triethylene glycol, polyhydric alcohol such as sorbitol, propylene oxide, polyethylene glycol, polypropylene glycol, etc. Is added.
  • polyether polyols include ADEKA Adeka Polyether P Series, G Series, EDP Series, BPX Series, FC Series, CM Series, NOF UNIOX (registered trademark) HC-40, HC-60, ST- 30E, ST-40E, G-450, G-750, Uniol (registered trademark) TG-330, TG-1000, TG-3000, TG-4000, HS-1600D, DA-400, DA-700, DB-400 Nonion (registered trademark) LT-221, ST-221, OT-221 and the like.
  • polyester polyol which is a preferable example of the specific polymer of the component (B)
  • polyvalent carboxylic acid such as adipic acid, sebacic acid, isophthalic acid, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, polyethylene glycol, polypropylene glycol, etc. And those obtained by reacting these diols.
  • polyester polyol examples include DIC polylite (registered trademark) OD-X-286, OD-X-102, OD-X-355, OD-X-2330, OD-X-240, OD-X-668, OD-X-2108, OD-X-2376, OD-X-2044, OD-X-688, OD-X-2068, OD-X-2547, OD-X-2420, OD-X-2523, OD- X-2555, OD-X-2560, Kuraray polyols P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F-510, F-1010, F -2010, F-3010, P-1011, P-2011, P-2013, P-2030, N-2010, PNNA-2016 and the like.
  • DIC polylite registered trademark
  • polycaprolactone polyol which is a preferred example of the specific polymer of the component (B) include those obtained by ring-opening polymerization of ⁇ -caprolactone using a polyhydric alcohol such as trimethylolpropane or ethylene glycol as an initiator.
  • polyhydric alcohol such as trimethylolpropane or ethylene glycol as an initiator.
  • Specific examples of the polycaprolactone polyol include DIC's Polylite (registered trademark) OD-X-2155, OD-X-640, OD-X-2568, Daicel Chemical's Plaxel (registered trademark) 205, L205AL, 205U, 208, 210 212, L212AL, 220, 230, 240, 303, 305, 308, 312, 320, and the like.
  • polycarbonate polyol which is a preferable example of the specific polymer of the component (B) include those obtained by reacting a polyhydric alcohol such as trimethylolpropane or ethylene glycol with diethyl carbonate, diphenyl carbonate, ethylene carbonate, or the like.
  • a polyhydric alcohol such as trimethylolpropane or ethylene glycol
  • diethyl carbonate diethyl carbonate
  • diphenyl carbonate ethylene carbonate
  • ethylene carbonate or the like.
  • Specific examples of the polycarbonate polyol include Placel (registered trademark) CD205, CD205PL, CD210, CD220 manufactured by Daicel Chemical Industries, and C-590, C-1050, C-2050, C-2090, C-3090 manufactured by Kuraray, and the like.
  • cellulose examples include hydroxyalkylcelluloses such as hydroxyethylcellulose and hydroxypropylcellulose, hydroxyalkylalkylcelluloses such as hydroxyethylmethylcellulose, hydroxypropylmethylcellulose and hydroxyethylethylcellulose, and cellulose.
  • hydroxyalkyl celluloses such as hydroxyethyl cellulose and hydroxypropyl cellulose are preferable.
  • the cyclodextrin which is a preferred example of the specific polymer of the component (B) includes cyclodextrins such as ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin And methylated cyclodextrins such as methyl- ⁇ -cyclodextrin, hydroxymethyl- ⁇ -cyclodextrin, hydroxymethyl- ⁇ -cyclodextrin, hydroxymethyl- ⁇ -cyclodextrin, hydroxymethyl- ⁇ -cyclodextrin, 2-hydroxyethyl- ⁇ -cyclodextrin, 2- Hydroxyethyl- ⁇ -cyclodextrin, 2-hydroxyethyl- ⁇ -cyclodextrin, 2-hydroxypropyl- ⁇ -cyclodextrin, 2-hydroxypropyl- ⁇ -cyclodextrin, 2-hydroxypropyl- ⁇ -
  • the melamine formaldehyde resin which is a preferable example of the specific polymer of the component (B) is a resin obtained by polycondensation of melamine and formaldehyde, and is represented by the following formula.
  • R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • n is a natural number representing the number of repeating units.
  • the methylol group generated during the polycondensation of melamine and formaldehyde is alkylated from the viewpoint of storage stability.
  • the method for obtaining the melamine formaldehyde resin as the component (B) is not particularly limited. Generally, melamine and formaldehyde are mixed, made weakly alkaline using sodium carbonate, ammonia, etc., and then heated at 60-100 ° C. Is synthesized. Further, the methylol group can be alkoxylated by reacting with alcohol.
  • the melamine formaldehyde resin as component (B) preferably has a weight average molecular weight of 250 to 5,000, more preferably 300 to 4,000, and still more preferably 350 to 3,500. If the weight average molecular weight is over 5,000, the solubility in the solvent may be lowered and the handling property may be lowered. If the weight average molecular weight is less than 250 and the weight is too small, Insufficient curing may reduce solvent resistance and heat resistance.
  • the melamine formaldehyde resin as the component (B) may be used in a liquid form or a solution form in which a purified liquid is redissolved in a solvent described later.
  • the (B) component melamine formaldehyde resin may be a mixture of a plurality of types of (B) component melamine formaldehyde resins.
  • phenol novolak resin which is a preferred example of the specific polymer of the component (B) include phenol-formaldehyde polycondensate.
  • the polymer of the component (B) may be used in a powder form or a solution form in which the purified powder is redissolved in a solvent described later.
  • the polymer of component (B) may be a mixture of a plurality of types of polymer of component (B).
  • Component (C) contained in the cured film forming composition of the present embodiment is a compound having two or more trialkoxysilyl groups.
  • a polymer having a trialkoxysilyl group may also be used.
  • the compound having two or more trialkoxysilyl groups include 1,4-bis (trimethoxysilyl) benzene, 1,4-bis (triethoxysilyl) benzene, and 4,4′-bis (trimethoxysilyl).
  • These compounds having two or more trialkoxysilyl groups can be used alone or in combination of two or more.
  • the content of the compound having two or more trialkoxysilyl groups as the component (C) is the total amount of the compound as the component (A) and the polymer as the component (B).
  • the amount is preferably 10 parts by mass to 100 parts by mass based on 100 parts by mass, and more preferably 15 parts by mass to 80 parts by mass.
  • the content of the compound having two or more trialkoxysilyl groups as component (C) is too small, the solvent resistance and heat resistance of the cured film obtained from the cured film forming composition are reduced, and the photo-alignment Sensitivity decreases.
  • the content is excessive, the photo-alignment property and the storage stability may be lowered.
  • the cured film forming composition of this Embodiment contains a crosslinking catalyst as (D) component in addition to (A) component, (B) component, and (C) component mentioned above.
  • a crosslinking catalyst which is (D) component it can be set as an acid or a thermal acid generator, for example.
  • This component (D) is effective in promoting a thermosetting reaction in the formation of a cured film using the cured film forming composition of the present embodiment.
  • the component (D) 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 capable of generating an acid by thermal decomposition at from 250C to 250C.
  • 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-
  • the content of the component (D) in the cured film forming composition of the embodiment of the present invention is preferably 0 with respect to 100 parts by mass of the total amount of the compound as the component (A) and the polymer as the component (B). 0.5 to 20 parts by mass, more preferably 0.8 to 15 parts by mass, and even more preferably 0.8 to 6 parts by mass.
  • the content of component (D) By setting the content of component (D) to 0.5 parts by mass or more, sufficient thermosetting and solvent resistance can be imparted, and high sensitivity to exposure can also be imparted.
  • the storage stability of a cured film forming composition can be made favorable by setting it as 20 mass parts or less.
  • the cured film forming composition of the present embodiment is mainly used in a solution state dissolved in a solvent.
  • the solvent used in that case should just be able to melt
  • 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.
  • solvents can be used alone or in combination of two or more.
  • a sensitizer is effective in promoting a photoreaction after forming a thermosetting film using the cured film forming composition of the present embodiment.
  • sensitizers as additives include benzophenone, anthracene, anthraquinone, thioxanthone, and derivatives thereof, and nitrophenyl compounds. Of these, 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. In particular, 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 use ratio of the sensitizer in the cured film forming composition of the present embodiment is 0.1 to 20 parts by mass with respect to 100 parts by mass of the total mass of the component (A) and the component (B). It is preferably 0.2 to 10 parts by 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 embodiment is a (A) component low molecular photo-alignment component, and (B) component (A) a polymer that is more hydrophilic than the photo-alignment component; It contains a compound having two or more trialkoxysilyl groups as component (C) and a crosslinking catalyst as component (D). And as long as the effect of this invention is not impaired, another additive can be contained.
  • the mixing ratio of the component (A) and the component (B) is preferably 5:95 to 65:35 by mass 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 embodiment are as follows. [1]: The mixing ratio of the component (A) and the component (B) is 5:95 to 65:35 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 10 parts by mass to 100 parts by mass of component (C) and 0.5 to 20 parts by mass of component (D).
  • the mixing ratio of the component (A) and the component (B) is 5:95 to 65:35 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 10 parts by mass to 100 parts by mass of component (C), 0.5 to 20 parts by mass of component (D), and a solvent.
  • the blending ratio, preparation method, and the like when the cured film forming composition of the present embodiment is used as a solution will be described in detail below.
  • the ratio of the solid content in the cured film forming composition of the present embodiment is not particularly limited as long as each component is uniformly dissolved in the solvent, but is preferably 1% by mass to 80% by mass, preferably Is 3% by mass to 60% by mass, more preferably 5% by mass to 40% by mass.
  • solid content means what remove
  • the method for preparing the cured film forming composition of the present embodiment is not particularly limited.
  • a preparation method for example, a method of mixing (A) component, (C) component and (D) component in a predetermined ratio to a solution of component (B) dissolved in a solvent to obtain a uniform solution, or this
  • other additives may be further added and mixed as necessary.
  • a solution of a specific polymer obtained by a polymerization reaction in a solvent can be used as it is.
  • a monomer having a polyethylene glycol ester group and a monomer having a hydroxyalkyl ester group having 2 to 5 carbon atoms at least one of a monomer having a carboxyl group and a monomer having a phenolic hydroxy group
  • the (A) component, the (C) component, and the (D) component are put into a solution of the component (B) obtained by copolymerizing the 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 of the cured film forming composition according to the present embodiment is 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.
  • the heating and drying conditions may be such that the cross-linking reaction with the cross-linking agent proceeds to such an extent that the components of the alignment material formed from the cured film do not elute into the polymerizable liquid crystal solution applied thereon.
  • a heating temperature and a heating time appropriately selected from the range of 0 ° C. to 200 ° C. and a time of 0.4 minutes to 60 minutes are employed.
  • the heating temperature and heating time are preferably 70 ° C. to 160 ° C., 0.5 minutes to 10 minutes.
  • the film thickness of the cured film formed using the curable composition of the present embodiment 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 the optical and electrical properties. be able to.
  • the cured film thus formed can function as an alignment material, that is, a member for aligning a liquid crystal compound such as liquid crystal by performing polarized UV irradiation.
  • ultraviolet light or visible light having a wavelength of 150 nm to 450 nm is usually used, and irradiation 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 embodiment has solvent resistance and heat resistance, after applying a retardation material composed of a polymerizable liquid crystal solution on the alignment material, 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 Embodiment 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.
  • the patterned phase difference material used for 3D display it is predetermined
  • polarized UV exposure is performed in the +45 degree direction from the reference, and then the polarized
  • the alignment materials on both the substrates are bonded to each other through a spacer, and then the substrates A liquid crystal display element in which the liquid crystal is aligned can also be obtained by injecting liquid crystal therebetween. Therefore, the cured film forming composition of this Embodiment can be used suitably for manufacture of various retardation materials (retardation film), a liquid crystal display element, etc.
  • MAA methacrylic acid MMA: methyl methacrylate
  • HEMA 2-hydroxyethyl methacrylate
  • AIBN ⁇ , ⁇ '-azobisisobutyronitrile
  • HPCEL hydroxypropylcellulose
  • AADEG polyester (adipic acid / diethylene glycol)
  • TTMSI Tris (3-trimethoxysilylpropyl) isocyanurate
  • BTMSE Bis (trimethoxysilyl) ethane
  • PTSA p-toluenesulfonic acid monohydrate
  • PPTS p-toluenesulfonic acid pyridine salt
  • the number average molecular weight and weight average molecular weight of the acrylic copolymer obtained in accordance with the following synthesis example were measured using a GPC apparatus (Shodex (registered trademark) columns KF803L and KF804L) manufactured by JASCO Corporation, and the elution solvent tetrahydrofuran was flowed at 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
  • Examples 1 to 5 Comparative Examples 1 and 2> Each cured film forming composition of an Example and a comparative example was prepared with the composition shown in Table 1, and adhesiveness, orientation sensitivity, pattern formability, and transmittance were evaluated for each.
  • a coating film having a thickness of 1.0 ⁇ m was formed.
  • This coating film was exposed at 1000 mJ / cm 2 to prepare a retardation material having a polymerizable liquid crystal layer on the cured film.
  • a crosscut (1 mm ⁇ 1 mm ⁇ 100 squares) is put on the surface of the phase difference material on the obtained substrate using a cutter knife, and then an adhesive tape is applied, and then the adhesive tape is peeled off and then the position on the substrate is removed. The number of squares where the phase difference material (cured film and polymerizable liquid crystal layer) did not peel off was counted. A case where 90 or more squares remained without peeling off the retardation material was judged to have good adhesion.
  • a coating film of 0.0 ⁇ m was formed. This coating film was exposed at 1000 mJ / cm 2 to prepare a retardation material having a polymerizable liquid crystal layer on the alignment material.
  • the retardation material on the produced substrate was sandwiched between a pair of polarizing plates, the state of retardation characteristics in the retardation material was observed, and the exposure amount of polarized UV necessary for the alignment material to exhibit liquid crystal alignment was measured. .
  • An alignment material having a higher alignment sensitivity can exhibit alignment in the polymerizable liquid crystal layer on the alignment material with a lower exposure amount.
  • 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.
  • This coating film was exposed at 1000 mJ / cm 2 to polymerize the polymerizable liquid crystal, and a patterned retardation material in which two types of regions having different retardation characteristics were regularly arranged was produced.
  • 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.
  • Table 2 shows the results of the above evaluation.
  • thermosetting film-forming compositions prepared in Examples 1 to 5 all exhibit liquid crystal alignment with an exposure amount less than 100 mJ / cm 2 and have high alignment sensitivity. I can understand. Moreover, optical patterning could be performed. Furthermore, it showed high transparency.
  • Comparative Examples 1 and 2 were difficult to align and could not be subjected to 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.

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Abstract

Le problème selon la présente invention consiste à fournir une composition formant un film durci destinée à former un film durci offrant un niveau d'adhésivité élevé et une efficacité de réaction à la lumière et une résistance aux solvants excellentes. L'invention doit également fournir un matériau d'orientation pour orientation optique et un matériau de déphasage formé en utilisant le matériau d'orientation. La solution proposée par l'invention est une composition formant un film durci contenant : (A) un composé ayant un groupe d'orientation optique et un ou plusieurs groupes de substitution choisis entre un groupe hydroxyle, un groupe carboxyle, un groupe trialcoxysilyle et un groupe amino ; (B) un polymère hydrophile ayant un ou plusieurs groupes de substitution choisis entre un groupe hydroxyle, un groupe carboxyle et un groupe amino ; (C) un composé ayant au moins deux groupes trialcoxysilyle ; et (D) un catalyseur de réticulation. L'utilisation de ladite composition formant un film durci permet de former un film durci, et un matériau d'orientation en employant une technologie d'orientation optique. Un cristal liquide polymérisable est appliqué sur le matériau d'orientation, on effectue un durcissement et on obtient un matériau de déphasage.
PCT/JP2014/060297 2013-04-16 2014-04-09 Composition formant un film durci, matériau d'orientation et matériau de déphasage Ceased WO2014171376A1 (fr)

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JP6458949B2 (ja) 2019-01-30
CN105283512B (zh) 2018-12-11
KR102165703B1 (ko) 2020-10-14
CN105283512A (zh) 2016-01-27
TWI623572B (zh) 2018-05-11
KR20150143540A (ko) 2015-12-23

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