WO2020175517A1 - Film et procédé pour la fabrication de celui-ci - Google Patents

Film et procédé pour la fabrication de celui-ci Download PDF

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Publication number
WO2020175517A1
WO2020175517A1 PCT/JP2020/007616 JP2020007616W WO2020175517A1 WO 2020175517 A1 WO2020175517 A1 WO 2020175517A1 JP 2020007616 W JP2020007616 W JP 2020007616W WO 2020175517 A1 WO2020175517 A1 WO 2020175517A1
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film
formula
group
polymer
independently
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PCT/JP2020/007616
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English (en)
Japanese (ja)
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真文 高橋
功一朗 別府
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日産化学株式会社
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Publication of WO2020175517A1 publication Critical patent/WO2020175517A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a film having a plurality of regions having a plurality of polymers having a specific structure, and a plurality of regions in which the orientations of the plurality of polymers are aligned, and a process for producing the film. Regarding the method.
  • a TN (Twisted Nematic) mode liquid crystal display device has been put into practical use. In this mode, it is necessary to use a polarizing plate in order to switch the light by utilizing the optical rotatory property of the liquid crystal, but the use efficiency of the light becomes low when the polarizing plate is used.
  • As an element there is an element that switches between a transparent state (also called a transparent state) and a scattering state of liquid crystal.
  • PD LC Polymer Dispersed Liquid Crystal
  • PN LC Polymer Network Liquid Crystal
  • liquid crystal display elements a liquid crystal composition containing a polymerizable compound that is polymerized by ultraviolet rays is placed between a pair of substrates equipped with electrodes, and the liquid crystal composition is cured by irradiation with ultraviolet rays. And a cured product of a polymerizable compound (for example, a polymer network) are formed. Then, in this liquid crystal display element, the scattering state and the transmission state of the liquid crystal are controlled by applying a voltage (see Patent Documents 1 and 2).
  • Patent Document 1 Japanese Patent No. 3552328.
  • Patent Document 2 Japanese Patent No. 4630954.
  • the object of the present invention is to provide a plurality of regions, which are found in providing the above liquid crystal display device, having a plurality of polymers having a specific structure, and in which the orientations of the plurality of polymers are aligned.
  • To provide a film made of Another object of the present invention is to provide a method for producing the film.
  • the present inventor has found the present invention having the following gist.
  • the present invention it is possible to provide a film having a plurality of regions having a plurality of polymers having a specific structure and having a plurality of regions in which the orientations of the plurality of polymers are aligned. ..
  • the present invention can provide a method for producing the film.
  • Fig. 1 is a polarizing microscope image (a film shows liquid crystallinity) of a film of a glass substrate having a liquid crystal alignment film obtained in Example 1.
  • FIG. 2 A scanning electron microscope (3M IV!) image of the film of the glass substrate with the liquid crystal alignment film obtained in Example 4.
  • FIG. 3 is a scanning electron microscope (3M IV!) image of the film of the glass substrate with the liquid crystal alignment film obtained in Example 4.
  • the present application provides a novel membrane and a method for manufacturing the membrane.
  • the above-mentioned polymers are not particularly limited, but include acrylic polymers, methacrylic polymers, novolac resins, epoxy resins, polyhydroxystyrenes, polyimide precursors, polyimides, polyamides, polyesters, polyethers. ⁇ 2020/175517 5 ⁇ (: 171-1? 2020/007616
  • it is a polyimide precursor or polyimide (collectively referred to as polyimide-based polymer).
  • the above-mentioned polymer preferably contains a liquid crystalline polymer, and preferably the above-mentioned polymer is a liquid crystalline polymer.
  • the liquid crystalline polymer exhibits liquid crystallinity in the range of 80 to 350 ° , preferably 100 to 300 ° , and more preferably 120 to 250°. Is good.
  • the polyimide precursor has a structure of the following formula [8].
  • 2 represents a divalent organic group.
  • Each eight 1 and 2 is a hydrogen atom or an alkyl group having a carbon number of 1-8.
  • 8 and 3 each represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or an acetyl group.
  • the door indicates a positive integer.
  • the diamine component is a diamine having two primary or secondary amino groups in the molecule
  • the tetracarboxylic acid component is a tetracarboxylic oxide compound or a tetracarboxylic dianhydride.
  • a tetracarboxylic acid dihalide compound, a tetracarboxylic acid dialkyl ester compound or a tetracarboxylic acid dialkyl ester dihalide compound is a tetracarboxylic oxide compound or a tetracarboxylic dianhydride.
  • a polyamic acid having a structural formula of a repeating unit of the formula [or] or a polyimide obtained by imidizing the polyamic acid is preferable.
  • the polymer of the formula [mouth] obtained above is added to the polymer of the formula [8] having 1 and 2 alkyl groups having 1 to 8 carbon atoms, and in the formula [] 3 and eight 4 alkyl group or an acetyl group with carbon number from 1 to 5 can also be introduced.
  • the polymer preferably has at least one kind of partial structure (also referred to as a specific partial structure (8)) selected from the following formulas [81] to [84], and preferably has the formula [84] ] It is good to have a partial structure of.
  • a specific partial structure (8) also referred to as a specific partial structure (8)
  • the polymer preferably has at least one kind of partial structure (also referred to as a specific partial structure (Mitsumi)) selected from the following formulas [Minami 1] to [Minami 7], and is preferable. ⁇ 2020/175 517 7 ⁇ (: 171-1? 2020/007616
  • ⁇ each independently represents an alkyl group having 1 to 3 carbon atoms, preferably 1 to 2 carbon atoms.
  • n 1 to n 4 each independently represent an integer of 0 to 2, preferably 0 or 1. Hydrogen on the aromatic ring, _ ⁇ _1 to 1 3, ten 3, over one Rei_1 ⁇ 1, one thousand 1 to 1, one 1 ⁇ 1_Rei 2, one-! - snake hundred, Or — (600) 2 may be substituted (where ___ is ⁇ “1:-butoxycarbonyl group”).
  • the polymer is composed of at least one partial structure 8 selected from the group 8 consisting of the following formulas [8 1] to [8 4], and the following formulas [1] to [7] It is preferable that the polymer is a polyimide-based polymer having at least one kind of partial structure selected from the group consisting of
  • a diamine having a specific partial structure () and a tetracarboxylic acid having a specific partial structure (M) are used, and a diamine having a specific partial structure (M) and a specific partial structure (8) are used.
  • a tetracarboxylic acid having is used is mentioned.
  • a diamine having a specific partial structure (8) (also referred to as a specific diamine (8).) ⁇ 2020/175 517 8 ⁇ (:171? 2020 /007616
  • a tetracarboxylic acid having a specific partial structure (Minami) (also referred to as a specific tetracarboxylic acid (B)), a diamine of the following formula [18] and a tetracarboxylic acid of the formula [2] are used, respectively. It is preferable.
  • X 1 and X 3 are each independently a single bond, 101, -001, 100001, 100001, 1CNH- , 1 ⁇ 1 1 ⁇ 1 x 0 1 or 1 !-indicates at least one selected from. Among them, a single bond, 101, 1001, 100001 or 100001 is preferable.
  • X 2 represents at least one selected from the above formula [8 1] to formula [8 4]. Above all, the formula [1] or the formula [4] is preferable from the viewpoint of the optical characteristics of the liquid crystal display device. Also, formula [8 1] to formula [8 4]
  • each of 1 and 5 independently represents at least one selected from an aromatic ring, an alicyclic group and a heterocyclic group. Of these, an aromatic ring or an alicyclic group is preferable.
  • 2 and 4 are each independently a single bond, 101, 1001, -0000 -, 1001, ⁇ one or one Indicates at least one selected from Of these, a single bond, 101, 1001, 100001 or —0.000— is preferable.
  • Reference numeral 3 represents at least one selected from the above formulas [Mis 1] to [Mis 7]. Among them, from the viewpoint of the optical characteristics of the liquid crystal display device, the formula [Min 1], the formula [Min 4] or the formula [Min 7] is preferable. Further, the details and preferred values of 3 to 30 and n 1 to 114 in the formulas [Mis 1] to [Mis 7] are as described above.
  • n 5 and n 6 each independently represent an integer of 0 or 1.
  • n 5 and n 6 are integers of 0, the structures of the formulas [Mis 1] to [Mis 7] are assumed to be directly bonded to the bond of the tetracarboxylic acid.
  • the use ratio of each of the specific diamine (8) and the specific tetracarboxylic acid (Mitsumi) is preferably as follows. Specifically, the use ratio of the specific diamine (8) is preferably 30 to 100 mol%, and preferably 50 to 100 mol% with respect to the entire diamine component from the viewpoint of the optical characteristics of the liquid crystal display element. More preferable. From the viewpoint of the optical characteristics of the liquid crystal display element, the use ratio of the specific tetracarboxylic acid (Mitsumi) is preferably 30 to 100 mol %, and preferably 50 to 100 mol% based on the whole tetracarboxylic acid component. % Is more preferable. Further, the specific diamine (8) and the specific tetracarbonic acid (Mitsumi) can be used either individually or in combination of two or more, depending on their respective characteristics.
  • X 4 represents at least one selected from the formulas [1] to [7].
  • the formula [Mis 1], the formula [Mis 4] or the formula [Mis 7] is preferable.
  • 3 to 3° and 1 to in expression [Mis 1] to [Mis 7] The details and preferences of 4 are as described above.
  • each of 6 and 10 independently represents at least one selected from an aromatic ring, an alicyclic group and a heterocyclic group. Of these, an aromatic ring or an alicyclic group is preferable.
  • 7 and 9 are each independently a single bond, 101, 1001, -0000-, 10011, ⁇ one or one Few to choose from ⁇ 2020/175517 10 ⁇ (: 171-1? 2020/007616
  • Reference numeral 8 represents at least one selected from the formula [8 1] to the formula [8 4]. Among them, the formula [84] is preferable from the viewpoint of the optical characteristics of the liquid crystal display device. Also,
  • Each of 7 and n 8 independently represents an integer of 0 or 1.
  • the use ratio of each of the specific diamine (Mitsumi) and the specific tetracarboxylic acid (8) is preferably as follows.
  • the usage ratio of the specific diamine (Mitsumi) is preferably from 30 to 100 mol% and more preferably from 50 to 100 mol% with respect to the entire diamine component from the viewpoint of the optical characteristics of the liquid crystal display element. More preferable.
  • the use ratio of the specific tetracarboxylic acid (8) is preferably 30 to 100 mol %, and preferably 50 to 100 mol% with respect to the whole tetracarboxylic acid component. More preferable.
  • the specific diamine (Mitsumi) and the specific tetracarboxylic acid (eight) may be used either individually or in combination of two or more, depending on their respective characteristics.
  • a diamine other than the specific diamine (8) and the specific diamine (Mitsumi) can be used as long as the effects of the present invention are not impaired.
  • the formula described on pages 34 to 38 of International Publication Gazette ⁇ / ⁇ 2 0 1 6/0 7 6 4 1 2 (2 0 16.5.19 publication) [3 3-1] to diamine compounds of the formula [3 3-5] other diamine compounds described on pages 39 to 42 of the publication, and on pages 42 to 44 of the publication. Examples include diamine compounds represented by the formulas [0 8 1] to [0 8 15].
  • Other Jami ⁇ 2020/175517 11 ⁇ (: 171-1? 2020/007616
  • the specific tetracarboxylic acid () and the specific tetracarboxylic acid (Mi) are the tetracarboxylic dianhydrides of the above formulas [2 8] and [2] and their tetracarboxylic acid derivatives.
  • a tetracarboxylic acid dihalide compound, a tetracarboxylic acid dialkyl ester compound or a tetracarboxylic acid dialkyl ester dihalide compound can be used.
  • tetracarboxylic acid component other tetracarboxylic acid other than the specific tetracarboxylic acid () and the specific tetracarboxylic acid (Mitsumi) can be used.
  • examples of other tetracarboxylic acids include the following tetracarboxylic acid compounds, tetracarboxylic acid dianhydrides, dicarboxylic acid dihalide compounds, dicarboxylic acid dialkyl ester compounds and dialkyl ester dihalide compounds.
  • the method for synthesizing the polyimide polymer is not particularly limited. Usually, it is obtained by reacting a diamine component and a tetracarboxylic acid component. Specifically, the method described on pages 46 to 50 of WO 201 6/0764 1 2 (Published on May 6, 2010) can be mentioned.
  • the reaction between the diamine component and the tetracarboxylic acid component is usually carried out in a solvent containing the diamine component and the tetracarboxylic acid component.
  • the solvent used at that time is not particularly limited as long as it can dissolve the formed polyimide precursor. Specifically, 1 ⁇ !-methyl-2-pyrrolidone, 1 ⁇ 1-ethyl-2-pyrrolidone, arbutyrolactone, 1 ⁇ 1, 1 ⁇ 1_dimethylformamide, 1 ⁇ 1, 1 ⁇ 1_dimethyl Acetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like can be mentioned.
  • methyl ethyl ketone, cyclohexanone, cyclopentanone, 4-hydroxy _4-methyl-2-pentanone or one of the following formulas [mouth 1] to formula [mouth 3] A solvent can be used.
  • Port 2 represents an alkyl group having 1 to 3 carbon atoms.
  • Mouth 3 represents an alkyl group having 1 to 4 carbon atoms.
  • these may be used alone or in combination.
  • a solvent that does not dissolve the polyimide precursor may be used as a mixture with the above-mentioned solvent as long as the formed polyimide precursor does not precipitate.
  • water in the organic solvent inhibits the polymerization reaction and causes hydrolysis of the formed polyimide precursor, it is preferable to use dehydrated and dried organic solvent.
  • the total number of moles of the tetracarboxylic acid component when the total number of moles of the diamine component is 1.0 is preferably 0.8 to 1.2. ..
  • Polyimide is a polyimide obtained by ring closure of a polyimide precursor, and in this polyimide, the ring closure rate (also referred to as imidation rate) of amide acid groups does not necessarily have to be 100%. , It can be adjusted arbitrarily according to the application and purpose. Among them, 30 to 80% is preferable from the viewpoint of the solubility of the polyimide polymer in the solvent. More preferred is 40 to 70%.
  • the molecular weight of the polyimido polymer is the weight average molecular weight measured by GPC (Gel Permeation Chromatograp hy) method, considering the strength of the film obtained therefrom, workability during film formation, and coating property. It is preferably 5,000 to 1,000,000, and more preferably 10,000 to 150,000.
  • the membrane of the present invention has a plurality of regions having a plurality of polymers each having the at least one partial structure A and the at least one partial structure B.
  • orientations of a plurality of polymers in the region are aligned. ⁇ 2020/175 517 13 ⁇ (:171? 2020 /007616
  • the film of the present invention has a region, a region, a region 0 (following, but for the sake of explanation, it is assumed that there are three regions 8 to 0).
  • Each of the regions to ⁇ has a plurality of polymers, and in each of the regions to ⁇ , the orientation directions of the plurality of polymers are aligned.
  • orientation direction 3 of the specific polymer in the region and the orientation direction 8 13 of the specific polymer in the region may be the same or different.
  • alignment direction 80 of the specific polymer in the region ⁇ and the alignment direction 80 of the specific polymer in the region ⁇ may be the same or different.
  • the film of the present invention can exhibit liquid crystallinity by having a plurality of the above regions.
  • the film of the present invention can be applied to a film using the liquid crystallinity that develops, for example, a liquid crystal display for the purpose of display, and a dimming window or a dimming window for controlling light blocking and transmission.
  • the present invention can be applied to, but is not limited to, an optical shutter element, a liquid crystal display and/or a liquid crystal alignment film used for an optical shutter element, a liquid crystal display element including the liquid crystal alignment film, and the like.
  • the membrane of the present invention can be produced, for example, by the following production method.
  • the step () is a step of preparing the first substrate.
  • the first substrate is a substrate for manufacturing a film.
  • the first substrate is ⁇ 2020/175 517 14 (:171? 2020 /007616
  • the first substrate is used together with the film thereafter, the first substrate should be appropriately selected according to the application.
  • the first substrate examples include, but are not limited to, a highly transparent substrate, depending on the subsequent application.
  • a highly transparent substrate for example, in addition to a glass substrate, a plastic substrate such as a polyamide substrate, a polyimide substrate, a polyethersulfone substrate, an acrylic substrate, a polycarbonate substrate, and a Mita (polyethylene terephthalate) substrate.
  • a plastic substrate such as a polyamide substrate, a polyimide substrate, a polyethersulfone substrate, an acrylic substrate, a polycarbonate substrate, and a Mita (polyethylene terephthalate) substrate.
  • Substrates, and even films thereof can be used, but are not limited to these.
  • a plastic substrate or film is preferable.
  • the step ( ⁇ ) is a step of preparing a film forming liquid containing a polymer or a precursor thereof.
  • the polymer or its precursor has the same definition as above and can be prepared as described above.
  • the film forming liquid is a solution for forming a film and contains a polymer or its precursor and a predetermined solvent.
  • a polymer or its precursor one kind or two or more kinds can be used.
  • the content of the solvent in the film forming liquid can be appropriately selected from the viewpoint of obtaining the coating method of the film forming liquid and the desired film thickness.
  • the content of the solvent in the liquid is preferably 50 to 99.9 mass% from the viewpoint of forming a uniform film by coating.
  • 60 to 99 mass% is preferable. More preferably, it is 65 to 99% by mass.
  • the solvent used for the film-forming liquid is not particularly limited as long as it is a solvent that dissolves the polymer.
  • the polymer is a polyimide precursor, polyimide, polyamide, polyester, polyether, polyurethane, poly(ester amide), poly(ester-imide), poly(ester-anhydride) or poly(ester-force). Carbonate), or acrylic polymer, methacrylic polymer ⁇ 2020/175 517 15 ⁇ (:171? 2020 /007616
  • the following solvents are preferably used.
  • Examples of the solvent eight compounds include, for example, 1 ⁇ 1, 1 ⁇ 1—dimethylformamide, 1 ⁇ 1, 1 ⁇ 1—dimethylacetamide, 1 ⁇ 1—methyl-2-pyrrolidone, 1 ⁇ 1—ethyl
  • Examples thereof include 2-pyrrolidone, dimethyl sulfoxide, tyrolactone, 1,3-dimethyl-2-imidazolinone, methyl ethyl ketone, cyclohexanone, cyclopentanone and 4-hydroxy-4-methyl-2-pentanone.
  • 1 ⁇ 1_methyl-2-pyrrolidone, 1 ⁇ 1_ethyl-2-pyrrolidone or ⁇ -ptyrolactone is preferable. These may be used alone or in combination.
  • the liquid crystalline polymer is a polyimide precursor, a polyimide, Polyamide, polyester, polyether, polyurethane, poly(ester amide), poly(ester-imide), poly(ester-anhydride) or poly(ester carbonate), which have high solubility in these solvents
  • the following solvent also referred to as solvent solvent
  • solvent solvent can be used.
  • solvent solvents are described on pages 58 to 60 of International Publication No. ⁇ 2 0 1 4/1 7 1 4 9 3 (2 0 1 4 1 .0.2 3 publication). Solvents such as Among them, 1-hexanol, cyclohexanol, 1,2-ethanedine
  • solvents can improve the coating property and surface smoothness of the film when the film-forming liquid is applied, so that they can be added to polymers such as polyimide precursors, polyimides, polyamides, polyesters and polyethers.
  • polymers such as polyimide precursors, polyimides, polyamides, polyesters and polyethers.
  • polyurethane, poly(ester amide), poly(ester-imide), poly(ester-anhydride) or poly(ester carbonate) it is preferable to use it in combination with the eight solvents.
  • the amount of the solvent is preferably 1 to 99% by mass of the whole solvent contained in the film forming liquid. Among them, 10 to 99 mass% is preferable. More preferably, it is 20 to 95% by mass.
  • a compound having an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a hydroxy group, a hydroxyalkyl group or a lower alkoxyalkyl group is introduced into the film forming liquid. You can also do it. In that case, it is necessary for the compound to have two or more of these groups.
  • crosslinkable compound having an epoxy group or an isocyanate group are described in International Publication WO 201 4/1 7 1 493 (published 201 4.10.23), pages 63 to 64.
  • examples thereof include crosslinkable compounds having a group or an isocyanate group.
  • crosslinkable compound having an oxetane group are represented by the formulas shown on pages 58 to 59 of International Publication WO ⁇ /0201 1/1 3275 1 (201 1.1.0.27 publication). ⁇ Crosslinkable compounds of the formula [4 ! ⁇ ] are mentioned.
  • crosslinkable compound having a cyclocarbonate group examples include compounds represented by the formula [5-1] listed on pages 76 to 82 of International Publication No. 0201 2/01 4898 (published on February 2, 2.2). ⁇ Crosslinkable compounds of the formula [5-42] are mentioned. Specific examples of the crosslinkable compound having a hydroxyl group, a hydroxyalkyl group and a lower alkoxyalkyl group are described on pages 65 to 66 of International Publication WO 201 4/1 7 1 493 (2 01 4.1 0.23 publication).
  • the content of the crosslinkable compound in the film forming liquid is preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of all the polymer components.
  • 0.1 to 50 parts by mass is more preferable with respect to 100 parts by mass of all polymer components, and most preferably 1 to 30 parts by mass. Is a department.
  • the film-forming liquid a compound that improves the uniformity of the film thickness and the surface smoothness when the film-forming liquid is applied can be used unless the effects of the present invention are impaired. Furthermore, when an electrode substrate or the like is provided on the film, a compound or the like that improves the adhesion between the film and the electrode substrate can be used.
  • Examples of the compound that improves the uniformity of the film thickness and the surface smoothness include a fluorine-based surfactant, a silicone-based surfactant, and a nonionic surfactant. Specific examples thereof include the surfactants described on page 67 of International Publication WO 201 4/1 7 1 493 (201 4.1 0.23 publication). Further, the use ratio thereof is preferably 0.01 to 2 parts by mass based on 100 parts by mass of all the polymer components contained in the film forming liquid. More preferred is 0.01 to 1 part by mass.
  • a dielectric or conductive substance for the purpose of changing the electric properties such as the dielectric constant and conductivity of the film may be added to the film forming liquid.
  • the step ( ⁇ ) is the step of applying the film forming liquid to one surface of the first substrate.
  • the application method can be a conventionally known method, for example, screen printing, offset printing, flexographic printing. ! ⁇ , inkjet method, dip method, mouth ⁇ 2020/175 517 18 (:171? 2020 /007616
  • the rucoater method, the slit coater method, the spinner method, the spray method and the like can be mentioned, but the method is not limited to these, and can be appropriately selected depending on the type of substrate and the intended film thickness of the resin film.
  • Step (v) is a step of heating the coated surface obtained in step (II I) to form a film on the first substrate.
  • Heating that is, heat treatment, depends on the type of substrate used, the film forming liquid used, particularly the solvent used for the film forming liquid, and the temperature range where the liquid crystallinity of the film is expressed.
  • Circular talent, ⁇ (Infrared) Can be heat-treated with a mold.
  • the heating conditions depend on the polymer used, the film-forming liquid used, particularly the solvent used for the film-forming liquid, the temperature range where the liquid crystallinity of the film is expressed, and the like. It is preferable that a plurality of regions having a plurality of are formed and that the heating be performed so that the orientations of the plurality of polymers are aligned in the regions.
  • the polymer is heated to a temperature range in which a liquid crystal phase is exhibited, and more specifically, 80 to 350°C, more preferably 100 to 300°C.
  • yo Ri preferably 1 2 0 ⁇ 3 0 0 ° ⁇ , most preferably 1 2 0 ⁇ 2 5 0 ° good to you warmed at ⁇ .
  • the film of the present invention that is, a film having a polymer having a specific partial structure, particularly a region having a plurality of the polymers
  • a film having a plurality of regions in which the orientations of the plurality of macromolecules are aligned can be formed on the first substrate.
  • the thickness of the film depends on, for example, the use of the film, but is, for example, 5 to 500 nm, preferably More preferably, it is from 10 to 250, and the method for producing a membrane of the present invention may include steps other than the steps (C) to (IV).
  • a step of separating the film of the present invention from the first substrate may be provided after the step (C), and a step of making the film of the present invention a self-supporting film may be provided. ⁇ 2020/175 517 19 (:171? 2020/007616 Example
  • Liquid crystal with physical properties of !_ 3 ( Ding: 102 ° 0, 8 ⁇ :a. 4, 8 ⁇ : ⁇ .236)
  • Liquid crystal with physical properties of !_4 (Cho: 90°, eight ⁇ : a. 4, eight: ⁇ .299)
  • Table 1 shows the liquid crystal alignment treatment agents obtained in the synthesis examples.
  • the liquid crystal alignment treatment agent obtained by the method of Synthesis Example was pressure-filtered with a membrane filter having a pore size of 1.
  • the obtained solution was spin-coated on a glass substrate (vertical: 300111111, lateral: 400!, thickness: 0.0) washed with pure water and isopropyl alcohol. At 80 ° ⁇ at 120 seconds, I
  • a glass substrate with a liquid crystal alignment film having a film thickness of 100 mm was obtained by performing heat treatment at 150 ° C. for 30 minutes in an 8 (infrared) type heat circulation type clean oven.
  • the liquid crystallinity of the obtained glass substrate with a liquid crystal alignment film was confirmed using the above-mentioned polarizing microscope with a cooling and heating stage for a microscope. Specifically, a liquid crystal phase-observed optical structure as shown in Fig. 1 was observed under a polarizing microscope. ⁇ 2020/175 517 25 ⁇ (: 171-1? 2020/007616
  • Crystallinity was defined, and those not observed were defined as having no liquid crystallinity.
  • a liquid crystal alignment film was sampled from the glass substrate with the liquid crystal alignment film obtained above, and the endothermic peak (liquid crystal phase/liquid crystal phase transition was measured using the differential scanning calorimeter (0 30). And the endothermic peak (which also indicates an isotropic phase transition of liquid crystal phase. Also referred to as Ding 2.) at that time, the rate of temperature increase/decrease is 10 ° ⁇ /min. However, Ding 1 and Ding 2 were obtained from the second skiyan.
  • the liquid crystal alignment treatment agent obtained by the method of Synthesis Example was pressure-filtered with a membrane filter having a pore size of 1.
  • the obtained solution was washed with pure water and water (isopropyl alcohol).
  • ⁇ Glass substrate with electrodes vertical: 40, horizontal: 3001 111, thickness: ⁇ .
  • a glass substrate with a liquid crystal alignment film of was obtained.
  • the surface shape of the obtained liquid crystal alignment film-attached glass substrate was observed using the above-mentioned scanning electron microscope (3M IV!). Specifically, by observing 3M 1 ⁇ /1, the size of one domain as shown in Fig. 2 is 400 to 700n. ⁇ 2020/175 517 26 ⁇ (:171? 2020 /007616
  • the polydomain structure refers to a structure having a plurality of specific polymers and having a plurality of regions in which the orientations of the plurality of polymers are aligned.
  • Table 3 summarizes the results of the 3M IV! observation.
  • those with a polydomain structure as shown in Figure 2 are marked with ⁇
  • those with no polydomain structure as shown in Figure 3 are marked with X.
  • a liquid crystal cell was obtained by leaving it at 23 ° for 15 hours.
  • the obtained liquid crystal cell was subjected to no voltage application ( ⁇ V) and voltage application (AC drive: 20 V). (Haze) was measured.
  • the measurement is based on I 3 ⁇ 7 1 3 6, and the higher the value of 1 to 1 3 2 6 when no voltage is applied, the better the scattering characteristics, and the lower the value of !! 3 2 6 when a voltage is applied, the more transparent it is. It is said that it has excellent properties.
  • Table 4 summarizes the measurement results for ⁇ .
  • liquid crystal alignment film exhibits liquid crystallinity, and excellent optical characteristics, that is, Haze in the absence of voltage application It was high, and H aze was low under voltage application.
  • the expression of liquid crystallinity is a comparison between Examples 1 to 3 and Comparative Examples 1 to 4, and the optical characteristics are a comparison between Examples 8 to 14 and Comparative Examples 9 to 12. ..
  • the present liquid crystal display device can be used for a liquid crystal display intended for display, and also for a dimming window or an optical shutter device for controlling the blocking and transmission of light.
  • a plastic substrate can be used.
  • this element can be used as a light guide plate of a display device such as an LCD (Liquid Crystal Display) or a OLED (Organic Light-emitting Diode) display, or a back plate of a transparent display using these displays.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne : un film comprenant une macromolécule ayant une structure particulière, en particulier un film comprenant une pluralité de zones qui renferment une pluralité de telles macromolécules, la pluralité de polymères à l'intérieur des zones étant orientés de manière alignée ; et un procédé pour la fabrication de celui-ci. Plus précisément, la présente invention concerne un film comprenant une pluralité de macromolécules qui ont au moins une structure partielle A choisie dans un groupe A constitué des formules [A1] à [A4] et au moins une structure partielle B choisie dans un groupe B constitué des formules [B1] à [B7].　[Formule chimique 1]
PCT/JP2020/007616 2019-02-27 2020-02-26 Film et procédé pour la fabrication de celui-ci WO2020175517A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022153873A1 (fr) * 2021-01-14 2022-07-21 日産化学株式会社 Composition polymère, agent d'alignement de cristaux liquides, film de résine, film d'alignement de cristaux liquides, procédé de production d'élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0728067A (ja) * 1993-04-23 1995-01-31 Toshiba Corp 液晶表示装置及びその製造方法
JP2009013165A (ja) * 2007-06-06 2009-01-22 Chisso Corp 酸二無水物、液晶配向膜および液晶表示素子
JP2011122130A (ja) * 2009-05-11 2011-06-23 Mitsubishi Chemicals Corp 液晶性ポリイミド、及びこれを含有する液晶性樹脂組成物、並びに半導体素子用樹脂膜
WO2018135657A1 (fr) * 2017-01-23 2018-07-26 日産化学工業株式会社 Agent d'alignement de cristaux liquides et procédé permettant de produire un film d'alignement de cristaux liquides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0728067A (ja) * 1993-04-23 1995-01-31 Toshiba Corp 液晶表示装置及びその製造方法
JP2009013165A (ja) * 2007-06-06 2009-01-22 Chisso Corp 酸二無水物、液晶配向膜および液晶表示素子
JP2011122130A (ja) * 2009-05-11 2011-06-23 Mitsubishi Chemicals Corp 液晶性ポリイミド、及びこれを含有する液晶性樹脂組成物、並びに半導体素子用樹脂膜
WO2018135657A1 (fr) * 2017-01-23 2018-07-26 日産化学工業株式会社 Agent d'alignement de cristaux liquides et procédé permettant de produire un film d'alignement de cristaux liquides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022153873A1 (fr) * 2021-01-14 2022-07-21 日産化学株式会社 Composition polymère, agent d'alignement de cristaux liquides, film de résine, film d'alignement de cristaux liquides, procédé de production d'élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides

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