WO2022102281A1 - Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides - Google Patents

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

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Publication number
WO2022102281A1
WO2022102281A1 PCT/JP2021/036656 JP2021036656W WO2022102281A1 WO 2022102281 A1 WO2022102281 A1 WO 2022102281A1 JP 2021036656 W JP2021036656 W JP 2021036656W WO 2022102281 A1 WO2022102281 A1 WO 2022102281A1
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WO
WIPO (PCT)
Prior art keywords
group
liquid crystal
crystal alignment
carbon atoms
alignment agent
Prior art date
Application number
PCT/JP2021/036656
Other languages
English (en)
Japanese (ja)
Inventor
新平 新津
佳和 原田
Original Assignee
日産化学株式会社
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 日産化学株式会社 filed Critical 日産化学株式会社
Priority to JP2022561322A priority Critical patent/JP7318826B2/ja
Priority to CN202180076210.7A priority patent/CN116529303B/zh
Publication of WO2022102281A1 publication Critical patent/WO2022102281A1/fr

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Classifications

    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • 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

  • liquid crystal alignment film in the industry is a film made of a polymer typified by a polyamic acid and / or an imidized polyimide formed on an electrode substrate, and the surface of the film is made of cotton or nylon. , It is manufactured by performing a so-called rubbing treatment of rubbing in one direction with a cloth such as polyester. The rubbing process is a simple and highly productive industrially useful method. Further, as an orientation treatment method instead of the rubbing treatment, a photo-alignment method for imparting a liquid crystal alignment ability by irradiating with polarized radiation is known.
  • the polyimide-based polymer used in the present invention has a nitrogen atom-containing heterocycle (excluding the imide ring of the polyimide), a secondary amino group, and a second amino group from the viewpoint of increasing the voltage retention of the obtained liquid crystal alignment film. It may have at least one nitrogen atom-containing structure (hereinafter, also referred to as a specific nitrogen atom-containing structure) selected from the group consisting of tertiary amino groups.
  • the polyimide-based polymer having a specific nitrogen atom-containing structure can be obtained by using a monomer having a nitrogen atom-containing structure, for example, a diamine having a specific nitrogen atom-containing structure as at least a part of a raw material.
  • the ratio of diamine having a specific nitrogen atom-containing structure is preferably 1 mol% or more, more preferably 2 mol% or more, based on the total amount of diamine used for synthesis, from the viewpoint of increasing the voltage holding ratio of the liquid crystal display element. ..
  • the usage ratio is preferably 90 mol% or less, more preferably 80 mol% or less.
  • organic solvent used in the above reaction examples include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, ⁇ -butyrolactone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, and the like. Examples thereof include 1,3-dimethyl-2-imidazolidinone. If the polymer has high solvent solubility, use methyl ethyl ketone, cyclohexanone, cyclopentanone, 4-hydroxy-4-methyl-2-pentanone, or the following formulas [D-1] to [D-3]. The indicated solvent can be used. These may be used by mixing two or more kinds.
  • the polyimide precursor may be a terminal-modified polymer obtained by using an appropriate terminal encapsulant together with the tetracarboxylic acid component and diamine as described above when producing the polyimide precursor.
  • the terminal modifier include acid anhydrides such as acetic anhydride, maleic anhydride, nagic anhydride, phthalic anhydride, itaconic anhydride, cyclohexanedicarboxylic acid anhydride, 3-hydroxyphthalic anhydride, and trimetic acid anhydride.
  • the polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of the polyamic acid, polyamic acid ester and polyimide is preferably 1,000 to 500,000, more preferably 2,000. ⁇ 500,000.
  • 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 15 or less, more preferably 10 or less. Within such a molecular weight range, good liquid crystal orientation of the liquid crystal display element can be ensured.
  • the solvent contained in the liquid crystal alignment agent is a mixed solvent in which a solvent (also referred to as a poor solvent) that improves the coatability when the liquid crystal alignment agent is applied and the surface smoothness of the coating film is used in addition to the above solvent. Is preferred. Specific examples of the solvent to be used in combination are described below, but the present invention is not limited thereto.
  • linking group examples include an alkylene group having 1 to 10 carbon atoms, a group obtained by removing one hydrogen atom from the alkylene group, a divalent or trivalent cyclohexane ring, and the like. Any hydrogen atom of the alkylene group may be substituted with an organic group such as an alkyl group having 1 to 6 carbon atoms, a fluorine atom or a trifluoromethyl group. Specific examples include the compounds described in International Publication No. 2010/074269 and the compounds represented by the following formulas (e-1) to (e-10).
  • the content of the crosslinkable compound in the liquid crystal aligning agent of the present invention is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the polymer component contained in the liquid crystal aligning agent, and the crosslinking reaction proceeds. In addition, from the viewpoint of exhibiting good resistance to AC afterimages, it is more preferably 1 to 15 parts by mass.
  • the irradiation amount of the above radiation is preferably 1 to 10,000 mJ / cm 2 . Of these, 100 to 5,000 mJ / cm 2 is preferable.
  • the substrate having the film-like substance may be irradiated while being heated at 50 to 250 ° C.
  • the liquid crystal alignment film thus produced can stably orient liquid crystal molecules in a certain direction.
  • the liquid crystal alignment film irradiated with polarized radiation can be contact-treated with water or a solvent, or the liquid crystal alignment film irradiated with radiation can be heat-treated.
  • water, 2-propanol, 1-methoxy-2-propanol or ethyl lactate are preferable from the viewpoint of versatility and solvent safety. More preferred are water, 1-methoxy-2-propanol or ethyl lactate.
  • the solvent may be used alone or in combination of two or more.
  • the two substrates are arranged so as to face each other so that the rubbing directions of the coating films are opposite to each other at a predetermined angle, for example, orthogonal or antiparallel.
  • the sealing agent for example, an epoxy resin containing a curing agent and aluminum oxide spheres as 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.
  • Standard sample for calibration line preparation TSK standard polyethylene oxide (molecular weight; about 900,000, 150,000, 100,000 and 30,000) (Made by Toso) and polyethylene glycol (molecular weight; about 12,000, 4,000 and 1,000) (manufactured by Polymer Laboratory).
  • DA-1 (14.3 g, 50.0 mmol) and NMP (145 g) were added to a 100 mL four-necked flask equipped with a stirrer and a nitrogen introduction tube, and the mixture was dissolved by stirring at room temperature under a nitrogen atmosphere. Then, CA-1 (10.5 g, 48.0 mmol) and NMP (36.4 g) were added, and the mixture was stirred at 50 ° C. for 16 hours to obtain a solution of polyamic acid (PAA-1) having a concentration of 12% (viscosity:: 525 mPa ⁇ s) was obtained.
  • PAA-1 polyamic acid having a concentration of 12% (viscosity:: 525 mPa ⁇ s) was obtained.
  • a glass substrate with an ITO electrode on the entire surface was prepared.
  • the substrate is a glass substrate having a size of 30 mm ⁇ 40 mm and a thickness of 1.1 mm, and an ITO electrode having a film thickness of 35 nm is formed on the entire surface of the substrate.
  • a spin coating method was applied to the ITO surface of the prepared substrate with electrodes. It was applied in. After drying on a hot plate at 80 ° C. for 2 minutes, it was fired in an infrared heating furnace at 230 ° C.

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

Abstract

La présente invention concerne un agent d'alignement de cristaux liquides qui permet l'obtention d'un film d'alignement de cristaux liquides qui a une haute résistance de film, tout en présentant une anisotropie élevée.　L'invention concerne également un agent d'alignement de cristaux liquides qui contient le composant (A) et le composant (B) décrits ci-dessous. Composant (A) : un polymère (A) qui a une capacité d'aligner des cristaux liquides Composant (B) : un composé hydroxyalkylamide (B) représenté par la formule (1) (Dans la formule (1), chaque P représente indépendamment un groupe comprenant un groupe *-C(=O)-N(R)2 ; W représente une structure partielle qui présente une cristallinité liquide ; chaque R représente indépendamment un groupe *-(CR'2)2-OH ; chaque R' représente indépendamment un atome d'hydrogène ou un groupe organique monovalent ayant de 1 à 6 atomes de carbone ; et * représente une main de liaison.)
PCT/JP2021/036656 2020-11-13 2021-10-04 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides WO2022102281A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2022561322A JP7318826B2 (ja) 2020-11-13 2021-10-04 液晶配向剤、液晶配向膜、及び液晶表示素子
CN202180076210.7A CN116529303B (zh) 2020-11-13 2021-10-04 液晶取向剂、液晶取向膜以及液晶显示元件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020-189724 2020-11-13
JP2020189724 2020-11-13

Publications (1)

Publication Number Publication Date
WO2022102281A1 true WO2022102281A1 (fr) 2022-05-19

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Country Status (4)

Country Link
JP (1) JP7318826B2 (fr)
CN (1) CN116529303B (fr)
TW (1) TW202225143A (fr)
WO (1) WO2022102281A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016118753A (ja) * 2014-12-22 2016-06-30 Jsr株式会社 液晶配向剤、液晶配向膜及び液晶表示素子
WO2020153659A1 (fr) * 2019-01-21 2020-07-30 주식회사 엘지화학 Composition d'alignement de cristaux liquides et film d'alignement de cristaux liquides, et dispositif d'affichage à cristaux liquides utilisant ceux-ci
WO2020184628A1 (fr) * 2019-03-12 2020-09-17 日産化学株式会社 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides les utilisant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017170681A1 (fr) * 2016-03-30 2017-10-05 日産化学工業株式会社 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides
CN117487569A (zh) * 2019-02-27 2024-02-02 日产化学株式会社 液晶取向剂、液晶取向膜以及液晶显示元件

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016118753A (ja) * 2014-12-22 2016-06-30 Jsr株式会社 液晶配向剤、液晶配向膜及び液晶表示素子
WO2020153659A1 (fr) * 2019-01-21 2020-07-30 주식회사 엘지화학 Composition d'alignement de cristaux liquides et film d'alignement de cristaux liquides, et dispositif d'affichage à cristaux liquides utilisant ceux-ci
WO2020184628A1 (fr) * 2019-03-12 2020-09-17 日産化学株式会社 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides les utilisant

Also Published As

Publication number Publication date
JP7318826B2 (ja) 2023-08-01
CN116529303A (zh) 2023-08-01
CN116529303B (zh) 2024-02-13
JPWO2022102281A1 (fr) 2022-05-19
TW202225143A (zh) 2022-07-01

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