WO2021070515A1 - Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément à cristaux liquides - Google Patents

Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément à cristaux liquides Download PDF

Info

Publication number
WO2021070515A1
WO2021070515A1 PCT/JP2020/032937 JP2020032937W WO2021070515A1 WO 2021070515 A1 WO2021070515 A1 WO 2021070515A1 JP 2020032937 W JP2020032937 W JP 2020032937W WO 2021070515 A1 WO2021070515 A1 WO 2021070515A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
liquid crystal
crystal alignment
polymer
alignment agent
Prior art date
Application number
PCT/JP2020/032937
Other languages
English (en)
Japanese (ja)
Inventor
陽一 廣▲瀬▼
岡田　敬
Original Assignee
Jsr株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jsr株式会社 filed Critical Jsr株式会社
Priority to CN202080070166.4A priority Critical patent/CN114502609B/zh
Priority to JP2021550451A priority patent/JP7409388B2/ja
Publication of WO2021070515A1 publication Critical patent/WO2021070515A1/fr

Links

Classifications

    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • 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
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
    • 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
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • 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 liquid crystal element includes a liquid crystal alignment film that orients liquid crystal molecules in a certain direction.
  • the liquid crystal alignment film is generally formed by applying a liquid crystal alignment agent in which a polymer component is dissolved in an organic solvent to a substrate, and preferably heating the substrate.
  • a liquid crystal alignment agent in which a polymer component is dissolved in an organic solvent
  • polyamic acid and soluble polyimide have been used for a long time because they are excellent in mechanical strength, liquid crystal orientation, and affinity with liquid crystals.
  • the present inventors control the orientation of the liquid crystal so that the long axis of the liquid crystal molecule is tilted at an appropriate angle with respect to the vertical direction (for example, the pretilt angle is 89 degrees or less in the vertically oriented liquid crystal element). By doing this, we tried to obtain a higher-definition liquid crystal element than before.
  • the liquid crystal alignment film is formed using the alignment film materials of Patent Document 1 and Patent Document 2
  • the long axis of the liquid crystal molecules cannot be sufficiently inclined with respect to the vertical direction, and the pretilt angle is larger than the desired angle. It turned out to be higher.
  • the present disclosure has been made in view of the above circumstances, and an object of the present disclosure is to provide a liquid crystal alignment agent capable of forming a liquid crystal alignment film having good coating uniformity and excellent pretilt angle characteristics. ..
  • the present inventors have found that when a polymer having a specific structure is used as a polymer component of a liquid crystal alignment agent in order to solve the above problems, the above problems can be solved. Specifically, according to the present disclosure, the following means are provided.
  • a 1 is a monovalent organic group
  • a 2 is a hydroxyl group or a monovalent organic group.
  • N1 and n2 are integers that independently satisfy 0 ⁇ n1 + n2 ⁇ 8.)
  • [2] A liquid crystal alignment film formed by using the liquid crystal alignment agent of the above [1].
  • [3] A liquid crystal element provided with the liquid crystal alignment film of the above [2].
  • [4] A polymer having a structural unit derived from at least one monomer selected from the group consisting of the compound represented by the above formula (1) and the compound represented by the above formula (2).
  • [5] A compound represented by the above formula (1).
  • [6] A compound represented by the above formula (2).
  • maleimide structure-containing compounds include, for example, N-methylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide, 4-carboxyphenylmaleimide, 2-methylphenylmaleimide, 4-hydroxyphenylmaleimide, N-dodecylmaleimide, N- Examples thereof include cholestanyloxycarbonylphenylmaleimide, and compounds in which the maleimide ring of these compounds is opened (ring-opened body).
  • the (meth) acrylic compound may have a (meth) acryloyl group, and the remaining structure is not particularly limited.
  • Specific examples of the (meth) acrylic compound include (meth) acrylic acid, ⁇ -ethylacrylic acid, maleic acid, fumaric acid, itaconic acid, alkyl (meth) acrylate, cycloalkyl (meth) acrylate, and (meth).
  • the polymer (A) may have a partial structure (hereinafter, also referred to as “photosensitizing structure”) capable of exhibiting a photosensitizing function that exhibits a sensitizing effect by light irradiation.
  • photosensitizing structure a partial structure capable of exhibiting a photosensitizing function that exhibits a sensitizing effect by light irradiation.
  • the photosensitizing function refers to a function of rapidly transitioning to a triplet excited state by causing intersystem crossing after becoming a singlet excited state by irradiation with light. When it collides with another molecule in this triplet state, it changes the partner to an excited state and returns to the ground state.
  • the addition polymer (A1) can be obtained by polymerizing the monomer (R1) and other monomers used as needed, preferably in the presence of a polymerization initiator in an organic solvent.
  • a polymerization initiator examples include 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), and 2,2'-azobis (4-methoxy-2). , 4-Dimethylvaleronitrile) and other azo compounds, nickel catalysts and the like.
  • the proportion of the polymerization initiator used is preferably 0.01 to 30 parts by mass with respect to 100 parts by mass of all the monomers used in the reaction.
  • the organic solvent used examples include alcohols, ethers, ketones, amides, esters, hydrocarbons and the like.
  • the reaction temperature is preferably 30 ° C. to 120 ° C.
  • the reaction time is preferably 1 to 36 hours.
  • the amount (a) of the organic solvent used should be such that the total amount (b) of the monomers used in the reaction is 0.1 to 60% by mass with respect to the total amount (a + b) of the reaction solution. Is preferable.
  • the reaction solution obtained by dissolving the polymer is known, for example, a method of pouring the reaction solution into a large amount of a poor solvent and drying the precipitate under reduced pressure, a method of distilling off the reaction solution under reduced pressure with an evaporator, and the like.
  • the addition polymer (A1) contained in the reaction solution may be isolated by the separation method and then used for preparation of the liquid crystal alignment agent.
  • the polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of the addition polymer (A1) is preferably 1,000 to 300,000, more preferably 2,000 to 100, It is 000.
  • the molecular weight distribution (Mw / Mn) represented by the ratio of Mw to the polystyrene-equivalent number average molecular weight (Mn) measured by GPC is preferably 7 or less, more preferably 5 or less.
  • the addition polymer (A1) used for preparing the liquid crystal alignment agent may be only one type or a combination of two or more types.
  • one of R 1 and R 2 in the above formulas (1) and (2) is a monovalent group having a polymerizable group, and the other is a hydrogen atom or a monovalent organic group. ..
  • the polymerizable group is preferably an alkoxysilyl group.
  • the specific silane compound is preferably at least one selected from the group consisting of the compound represented by the following formula (7) and the compound represented by the following formula (8).
  • R 23 is a divalent hydrocarbon group having 1 to 20 carbon atoms
  • R 24 and R 25 are independently monovalent groups having 1 to 10 carbon atoms.
  • R 27 is a hydrogen atom or a monovalent organic group.
  • K is an integer of 1 to 3.
  • a 1 , A 2 , n1 and n2 are the above formulas (1) and (1) and (1). It is synonymous with 2).
  • the content ratio of the structural unit U1 in the polyorganosiloxane (A) is based on the total monomer units of the polyorganosiloxane (A) from the viewpoint of improving the pretilt angle characteristics (initial pretilt angle and postbake margin). It is preferably 1 mol% or more, more preferably 2 mol% or more, and further preferably 5 mol% or more.
  • the content ratio of the structural unit U1 is preferably 90 mol% or less, more preferably 80 mol% or less, and more preferably 60 mol, based on all the monomer units of the polyorganosiloxane (A). It is more preferably% or less.
  • the structural unit U1 of the polyorganosiloxane (A) may be one type or two or more types.
  • the polystyrene-equivalent weight average molecular weight (Mw) measured by GPC is preferably in the range of 100 to 50,000, more preferably in the range of 200 to 10,000.
  • the liquid crystal alignment agent of the present disclosure may contain other components other than the polymer (A), if necessary.
  • the polyamic acid can be obtained by reacting a tetracarboxylic dianhydride with a diamine compound.
  • a tetracarboxylic dianhydride and the diamine compound conventionally known compounds used for the synthesis of polyamic acid can be used.
  • the polyamic acid ester is, for example, a method of reacting the polyamic acid obtained above with an esterifying agent (for example, methanol, ethanol, N, N-dimethylformamide diethylacetal, etc.); a tetracarboxylic acid diester and a diamine compound.
  • the additive (S) include acetophenone structure-containing compounds such as acetophenone, acetophenone benzyl ketal, 2,2-dimethoxy-2-phenylacetophenone, and 3-methylacetophenone; benzophenone, 4-diethylamino-2-hydroxybenzophenone, 2-Hydroxybenzophenone, 4-methylbenzophenone, 3- (4-benzoyl-phenoxy) propyl, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, 4,4'-bis (dimethylamino) benzophenone (Michler ketone) ) And other benzophenone structure-containing compounds; 3,5-dinitrobenzene, 4-methyl-3,5-dinitrobenzene, 3- (3,5-dinitrophenoxy) propyl, 2-methyl-3,5-dinitrobenzene, etc.
  • acetophenone structure-containing compounds such as acetophenone, acetophenone
  • Nitroaryl structure-containing compounds hydrocarbons such as naphthalene, anthracene, biphenyl, terphenyl, 2,3-benzophenone, pyrene, perylene, fluorene, anthraquinone; 9,10-dioxo-9,10-dihydroanthracene, 3- Anthracene derivatives such as (9,10-dioxo-9,10-dihydroanthracene-2-yl) propyl, 2-oxo-9,10-dihydroanthracene; amino group-containing compounds such as triphenylamine and carbazole; thioxanthone, diethyl Sulfur-containing compounds such as thioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one; 2,4,6-trimethylbenzo
  • R 1 is an alkyl group having 1 to 4 carbon atoms or CH 3 CO-
  • R 2 is an alkanediyl group having 1 to 4 carbon atoms or-(CH 2 CH 2 O).
  • N-CH 2 CH 2- where n is an integer of 1 to 4
  • R 3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 4 is an alkanediyl group having 1 to 3 carbon atoms.
  • R 5 and R 6 are independently alkyl groups having 4 to 8 carbon atoms.
  • Specific examples of the specific solvent include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether, 3-methoxy-1-butanol, and ethylene glycol monomethyl ether as compounds represented by the above formula (D-1).
  • Ethylene glycol monoethyl ether ethylene glycol monopropyl ether, ethylene glycol-n-butyl ether (butyl cellosolve), ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, etc.
  • D-2 cyclobutanone, cyclopentanone, cyclohexanone
  • Examples of the compound represented by the above formula (D-3) include diisobutyl ketone and the like.
  • the specific solvent one type may be used alone, or two or more types may be used in combination.
  • the content ratio of the specific solvent is preferably 20% by mass or more, preferably 40% by mass or more, based on the total amount of the solvent contained in the liquid crystal aligning agent. Is more preferable, and 50% by mass or more is further preferable.
  • the solubility in a low boiling point solvent such as a specific solvent is good, and the post-bake temperature is set to, for example, 200 ° C. or lower, preferably 180 ° C. or lower, more preferably. Even when the temperature is set to 160 ° C. or lower, the variation in the pretilt angle due to the difference in the pre-bake temperature can be further reduced, which is preferable.
  • the film thickness of the film thus formed is preferably 0.001 to 1 ⁇ m.
  • ⁇ Step 2 Orientation treatment>
  • a treatment (alignment treatment) for imparting a liquid crystal alignment ability to the coating film formed in the above step 1 is performed.
  • the alignment ability of the liquid crystal molecules is imparted to the coating film to form a liquid crystal alignment film.
  • the coating film formed in the above step 1 can be used as it is as a liquid crystal alignment film, but in order to further enhance the liquid crystal alignment ability, the coating film is oriented. It is good to apply.
  • the alignment treatment it is preferable to use a photo-alignment treatment in which the coating film formed on the substrate is irradiated with light to impart the liquid crystal alignment ability to the coating film.
  • Examples of the light source used include a low-pressure mercury lamp, a high-pressure mercury lamp, a deuterium lamp, a metal halide lamp, an argon resonance lamp, a xenon lamp, an excimer laser, and the like.
  • the irradiation amount of radiation is preferably 400 to 50,000 J / m 2 , and more preferably 1,000 to 20,000 J / m 2 .
  • the surface of the substrate is washed with, for example, water, an organic solvent (for example, methanol, isopropyl alcohol, 1-methoxy-2-propanol acetate, butyl cellosolve, ethyl lactate, etc.) or a mixture thereof. Or a process of heating the substrate may be performed.
  • a liquid crystal cell is manufactured by preparing two substrates on which the liquid crystal alignment film is formed as described above and arranging the liquid crystal between the two substrates arranged opposite to each other.
  • two substrates are arranged to face each other with a gap so that the liquid crystal alignment films face each other, and the peripheral portions of the two substrates are bonded to each other using a sealant to be attached to the substrate surface.
  • sealant examples thereof include a method of injecting and filling a liquid crystal in a cell gap surrounded by a sealing agent to seal the injection hole, a method of using the ODF method, and the like.
  • the sealing agent for example, an epoxy resin containing an aluminum oxide sphere as a curing agent and a spacer can be used.
  • the liquid crystal include a nematic liquid crystal and a smectic liquid crystal, and among them, the nematic liquid crystal is preferable.
  • the PSA mode after the liquid crystal cell is constructed, the liquid crystal cell is irradiated with light while a voltage is applied between the conductive films of the pair of substrates.
  • the weight average molecular weight and the number average molecular weight of the polymer were measured by the following methods.
  • Weight average molecular weight (Mw) and number average molecular weight (Mn) of polymer are polystyrene-equivalent values measured by gel permeation chromatography under the following conditions.
  • reaction solution was purified twice with hydrochloric acid (1N) and twice with water. The organic layer was then concentrated on an evaporator. The obtained solid was crystallized from THF / ethanol / water to obtain 10.0 g of Intermediate 2.
  • Intermediate 2 was dissolved in THF, 14.5 g of Compound CA was further added, and the mixture was reacted at 50 ° C. for 1 hour. After the reaction, the solvent was distilled off to obtain 22.9 g of compound (MA-4).
  • the organic layer is taken out, washed with a 0.2 mass% ammonium nitrate aqueous solution until the washed water becomes neutral, and then the solvent and water are distilled off under reduced pressure to obtain a polyorganosiloxane.
  • the coalescence (P-6) was obtained as a viscous clear liquid.
  • the weight average molecular weight (Mw) of the obtained polymer (P-6) was 11000.
  • liquid crystal alignment agent (AL-1) prepared in (1) above is applied with a spinner on the transparent electrode surface of a glass substrate with a transparent electrode made of an ITO film, and the temperature is 80 ° C.
  • Pre-baking was performed for 1 minute on the hot plate of No. 1 to form a coating film having a film thickness of 0.08 ⁇ m.
  • the surface of the coating film was irradiated with polarized ultraviolet rays of 200 J / m 2 containing a bright line of 313 nm at room temperature from a direction inclined by 40 ° from the normal of the substrate using an Hg-Xe lamp and a Gran Tailor prism.
  • the liquid crystal alignment film surfaces of the substrates are opposed to each other, and the pair of substrates are crimped so that the projection directions of the optical axes of the ultraviolet rays radiated to each substrate are opposite to each other, and the adhesive is applied at 150 ° C. for 1 hour. It was heat-cured.
  • a nematic liquid crystal (MLC-6608, manufactured by Merck Co., Ltd.) was filled in the gap between the substrates from the liquid crystal injection port, and then the liquid crystal injection port was sealed with an epoxy adhesive to obtain a liquid crystal cell. Further, in order to eliminate the flow orientation at the time of liquid crystal injection, the liquid crystal cell was heated at 150 ° C. and then slowly cooled to room temperature.
  • polarizing plates are placed on both outer surfaces of the substrate in the liquid crystal cell, and the polarization directions thereof are orthogonal to each other, and the direction of projection of the optical axis of the ultraviolet rays irradiated at the time of forming the liquid crystal alignment film on the substrate surface is 45 °. It was pasted together so as to make it.
  • the liquid crystal alignment agent (AL-1) prepared in (1) above is coated on a glass substrate using a spinner, prebaked on a hot plate at 80 ° C. for 1 minute, and then prebaked.
  • a coating film having an average film thickness of 0.1 ⁇ m was formed by heating (post-baking) the inside of the chamber in a nitrogen-substituted oven at 200 ° C. for 1 hour.
  • the surface of the obtained coating film was observed with an atomic force microscope (AFM), and the uniformity of the coating film surface was evaluated by measuring the center average roughness (Ra).
  • AFM atomic force microscope
  • the coating uniformity was evaluated as “good ( ⁇ )”, when it was larger than 5 nm and less than 10 nm, it was evaluated as “possible ( ⁇ )”, and when it was 10 nm or more, it was evaluated as “poor ( ⁇ )”. As a result, in this example, the evaluation was "OK ( ⁇ )".
  • Example 1 to 10 in which the liquid crystal alignment agent containing the polymer (A) was used, the pretilt angle was less than 89 degrees, and Comparative Examples 1 to 4 containing no polymer (A) were used. In comparison, the tilt angle of the liquid crystal molecules from the vertical direction could be made sufficiently large. Further, in Examples 1 to 10, the variation in the pretilt angle due to the difference in the post-bake temperature was small. In particular, in Examples 8 and 9 containing a polymer having a photosensitizing structure and Example 10 containing an additive having a photosensitizing structure, the evaluation of the post-bake margin was "excellent", which was particularly excellent. It was. Further, the liquid crystal alignment agents of Examples 1 to 10 had good coating uniformity.
  • the coating uniformity can be improved by using the ring-opening body as the monomer (R1). From these results, it was found that by using the polymer (A), it is possible to form a liquid crystal alignment film having good coating uniformity and excellent pretilt angle characteristics.

Abstract

L'invention concerne un polymère (A) ayant des motifs structuraux dérivés d'au moins un monomère choisi dans le groupe constitué par un composé représenté par la formule (1) et un composé représenté par la formule (2) est inclus dans cet agent d'alignement de cristaux liquides. Dans les formules, de R1 et R2, l'un de R1 et R2 est un groupe univalent ayant un groupe polymérisable et l'autre est un atome d'hydrogène ou un groupe organique univalent, ou R1 et R2 sont combinés l'un à l'autre pour représenter une structure cyclique formée conjointement avec l'atome d'azote auquel R1 et R2 sont liés. Cependant, la structure cyclique a une liaison carbone-carbone polymérisable. Dans les formules, A1 est un groupe organique univalent, et A2 est un groupe hydroxyle ou un groupe organique univalent. Dans les formules, 0 ≤ n1 + n2 ≤ 8 est satisfaite.
PCT/JP2020/032937 2019-10-10 2020-08-31 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément à cristaux liquides WO2021070515A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202080070166.4A CN114502609B (zh) 2019-10-10 2020-08-31 液晶取向剂、液晶取向膜、液晶元件、聚合物及化合物
JP2021550451A JP7409388B2 (ja) 2019-10-10 2020-08-31 液晶配向剤、液晶配向膜及び液晶素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019187165 2019-10-10
JP2019-187165 2019-10-10

Publications (1)

Publication Number Publication Date
WO2021070515A1 true WO2021070515A1 (fr) 2021-04-15

Family

ID=75437148

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/032937 WO2021070515A1 (fr) 2019-10-10 2020-08-31 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément à cristaux liquides

Country Status (4)

Country Link
JP (1) JP7409388B2 (fr)
CN (1) CN114502609B (fr)
TW (1) TW202122563A (fr)
WO (1) WO2021070515A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023171757A1 (fr) * 2022-03-10 2023-09-14 日産化学株式会社 Composition polymère, matériau à différence de phase monocouche et agent d'alignement de cristaux liquides
WO2024058164A1 (fr) * 2022-09-13 2024-03-21 日産化学株式会社 Agent d'alignement de 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
JPS50123665A (fr) * 1974-02-05 1975-09-29
JP2010101999A (ja) * 2008-10-22 2010-05-06 Chisso Corp 液晶配向膜、液晶配向剤および液晶表示素子
JP2012180482A (ja) * 2011-03-02 2012-09-20 Jnc Corp マレイミド系高分子を含有する組成物、およびマレイミド系高分子共重合体の製造方法
WO2016025752A1 (fr) * 2014-08-14 2016-02-18 Prolynx Llc Réactifs de conjugaison thiol et conjugués formés à partir de ceux-ci

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0010651A (pt) * 1999-05-17 2002-03-19 Novo Nordisk As Composto, uso de um composto, composição farmacêutica, e, método para o tratamento e/ou prevenção de distúrbios ou de doenças mediadas por uma ação antagonìstica de glucagon
KR20080025316A (ko) * 2006-09-15 2008-03-20 칫소가부시키가이샤 액정 배향제, 액정 배향막 및 액정 표시 소자
CN102220141A (zh) * 2010-04-16 2011-10-19 统炀企业有限公司 高分子液晶配向添加物及液晶显示装置的制造方法
JP6686298B2 (ja) * 2014-08-25 2020-04-22 Jsr株式会社 液晶配向剤、液晶配向膜及び液晶表示素子
JP6596931B2 (ja) * 2014-08-29 2019-10-30 Ｊｓｒ株式会社 液晶配向剤、液晶配向膜及び液晶表示素子
JP6701668B2 (ja) * 2015-02-03 2020-05-27 Jsr株式会社 液晶配向剤、液晶配向膜、液晶配向膜の製造方法及び液晶素子

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50123665A (fr) * 1974-02-05 1975-09-29
JP2010101999A (ja) * 2008-10-22 2010-05-06 Chisso Corp 液晶配向膜、液晶配向剤および液晶表示素子
JP2012180482A (ja) * 2011-03-02 2012-09-20 Jnc Corp マレイミド系高分子を含有する組成物、およびマレイミド系高分子共重合体の製造方法
WO2016025752A1 (fr) * 2014-08-14 2016-02-18 Prolynx Llc Réactifs de conjugaison thiol et conjugués formés à partir de ceux-ci

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023171757A1 (fr) * 2022-03-10 2023-09-14 日産化学株式会社 Composition polymère, matériau à différence de phase monocouche et agent d'alignement de cristaux liquides
WO2024058164A1 (fr) * 2022-09-13 2024-03-21 日産化学株式会社 Agent d'alignement de cristaux liquides et élément d'affichage à cristaux liquides

Also Published As

Publication number Publication date
CN114502609A (zh) 2022-05-13
CN114502609B (zh) 2023-08-15
JPWO2021070515A1 (fr) 2021-04-15
JP7409388B2 (ja) 2024-01-09
TW202122563A (zh) 2021-06-16

Similar Documents

Publication Publication Date Title
TWI564345B (zh) 液晶配向劑以及化合物
JP6911885B2 (ja) 液晶配向膜の製造方法及び液晶素子の製造方法
CN107338058B (zh) 液晶取向剂、液晶取向膜及其制造方法、液晶元件、聚合物以及化合物
TWI746666B (zh) 液晶配向劑、液晶配向膜及液晶元件
JP7409388B2 (ja) 液晶配向剤、液晶配向膜及び液晶素子
JP2020079812A (ja) 液晶配向膜の製造方法および液晶素子
TWI739929B (zh) 液晶配向劑、液晶配向膜、液晶元件及聚合體
TWI746668B (zh) 液晶配向劑、液晶配向膜及液晶元件
TWI711671B (zh) 液晶配向劑、液晶配向膜、液晶元件、以及液晶配向膜及液晶元件的製造方法
JP7322894B2 (ja) 液晶配向剤及びその製造方法、液晶配向膜並びに液晶素子
TWI815876B (zh) 液晶配向劑、液晶配向膜、液晶元件及液晶元件的製造方法
JP6962456B2 (ja) 液晶配向剤、液晶配向膜、液晶素子、重合体及び化合物
WO2019159470A1 (fr) Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément de cristaux liquides
WO2018016263A1 (fr) Procédé de fabrication d' élémént à cristaux liquides
WO2018221123A1 (fr) Procédé de fabrication d'un élément à cristaux liquides et agent d'alignement de cristaux liquides
JP6981541B2 (ja) 液晶配向剤、液晶配向膜、液晶素子及び液晶素子の製造方法
TWI791838B (zh) 液晶配向劑、液晶配向膜、液晶元件及液晶元件的製造方法
WO2021049255A1 (fr) Agent d'orientation de cristaux liquides, film d'orientation de cristaux liquides, et élément à cristaux liquides
JP2022173076A (ja) 液晶配向剤、液晶配向膜及びその製造方法、液晶素子、液晶表示装置、並びに重合体
WO2021005888A1 (fr) Agent et film d'alignement de cristaux liquides et élément à cristaux liquides
TW202307087A (zh) 液晶配向劑、液晶配向膜、液晶元件、以及聚合體及其製造方法
JP2023117826A (ja) 液晶配向剤、液晶配向膜及び液晶素子
JP2022101462A (ja) 液晶配向剤、液晶配向膜及び液晶素子
WO2019176276A1 (fr) Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément à cristaux liquides
JP2023107736A (ja) 液晶配向剤、液晶配向膜、液晶素子及び液晶素子の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20873397

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021550451

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20873397

Country of ref document: EP

Kind code of ref document: A1