WO2019181882A1 - Élément d'affichage à cristaux liquides - Google Patents

Élément d'affichage à cristaux liquides Download PDF

Info

Publication number
WO2019181882A1
WO2019181882A1 PCT/JP2019/011259 JP2019011259W WO2019181882A1 WO 2019181882 A1 WO2019181882 A1 WO 2019181882A1 JP 2019011259 W JP2019011259 W JP 2019011259W WO 2019181882 A1 WO2019181882 A1 WO 2019181882A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
carbon atoms
crystal display
group
display element
Prior art date
Application number
PCT/JP2019/011259
Other languages
English (en)
Japanese (ja)
Inventor
保坂　和義
雅章 片山
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 JP2020507805A priority Critical patent/JP7226428B2/ja
Priority to KR1020207029717A priority patent/KR20200130435A/ko
Priority to CN201980019741.5A priority patent/CN111868615A/zh
Publication of WO2019181882A1 publication Critical patent/WO2019181882A1/fr

Links

Classifications

    • 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
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • 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
    • 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
    • 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
    • G02F1/1334—Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals

Definitions

  • the present invention relates to a transmission / scattering liquid crystal display element.
  • a TN (Twisted Nematic) mode As a liquid crystal display element, a TN (Twisted Nematic) mode has been put into practical use. In this mode, it is necessary to use a polarizing plate in order to switch light using the optical rotation characteristics of the liquid crystal. When a polarizing plate is used, the light use efficiency is lowered.
  • a liquid crystal display element that does not use a polarizing plate there is an element that performs switching between a liquid crystal transmission state (also referred to as a transparent state) and a scattering state.
  • PDLC Polymer Dispersed Liquid Crystal
  • PNLC Polymer Network Liquid Crystal
  • liquid crystal display elements In these 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 provided with electrodes, and the liquid crystal composition is cured by irradiation with ultraviolet rays, whereby the liquid crystal and the polymerizable compound are polymerized. Forms a complex with a cured product of the compound (eg, a polymer network).
  • the scattering state and the transmission state of the liquid crystal are controlled by applying a voltage.
  • liquid crystal display elements using PDLC or PNLC when no voltage is applied, the liquid crystal is in a random direction, so it becomes cloudy (scattering).
  • voltage is applied, the liquid crystal is aligned in the electric field direction and transmits light.
  • a liquid crystal display element that is in a transmissive state also referred to as a normal element.
  • the electrode and the liquid crystal layer are in direct contact (see Patent Documents 1 and 2).
  • liquid crystal display element using PDLC also referred to as a reverse type element
  • PDLC also referred to as a reverse type element
  • the present invention improves the adhesion between the liquid crystal layer and the electrode, and even in a harsh environment exposed to high temperature, high humidity and light irradiation for a long time, the device is peeled off, the generation of bubbles, and the optical
  • An object of the present invention is to provide a liquid crystal display element capable of suppressing deterioration of characteristics.
  • the present invention has a liquid crystal layer that is cured by irradiating ultraviolet rays to a liquid crystal composition containing a liquid crystal and a polymerizable compound disposed between a pair of substrates provided with electrodes, and in a scattering state when no voltage is applied.
  • a liquid crystal display element that becomes transparent when a voltage is applied, wherein the liquid crystal composition contains a compound represented by the following formula [1].
  • X 1 represents the following formula [1-a] or [1-b]:
  • X 2 represents an alkylene group having 2 to 24 carbon atoms, and is an arbitrary group not adjacent to X 1 and O of the alkylene group.
  • —CH 2 — may be substituted with —O—, —CO—, —COO—, —OCO—, —CONH—, —NHCO—, —NH— or —CON (CH 3 ) —, where Xm is Represents an integer of 1 or 2.
  • Xn represents an integer of 1 or 2. However, Xm + Xn is 3.
  • the adhesion between the liquid crystal layer and the electrode is improved, and even in a harsh environment exposed to high temperature and high humidity or light irradiation for a long time, the device is peeled off, bubbles are generated, and the optical characteristics are deteriorated.
  • a liquid crystal display element that is in a scattering state when no voltage is applied and in a transparent state when a voltage is applied can be obtained. Therefore, the element of the present invention can be used for a liquid crystal display for display purposes, a dimming window for controlling blocking and transmission of light, an optical shutter element, and the like.
  • the mechanism by which the liquid crystal display device having the above-described excellent characteristics is obtained by the present invention is not necessarily clear, but is estimated as follows.
  • the liquid crystal composition used in the present invention contains a liquid crystal, a polymerizable compound, and a compound represented by the formula [1] (also referred to as a specific compound).
  • the specific compound has a site that undergoes a polymerization reaction by ultraviolet rays represented by X 1 in formula [1] and a phosphate group. Therefore, when a specific compound is included in the liquid crystal composition, an interaction between a phosphoric acid group and an inorganic electrode such as an ITO electrode works, and the X1 site in the formula [1] reacts with the polymerizable compound. This is considered to increase the adhesion between the polymer network in the liquid crystal layer and the electrode.
  • the liquid crystal display element using the liquid crystal composition of the present invention improves the adhesion between the liquid crystal layer and the electrode, and even in harsh environments exposed to high temperature and high humidity and light irradiation for a long time. It becomes a liquid crystal display element which can suppress peeling of an element, generation
  • it can be suitably used for a normal element that is in a scattering state when no voltage is applied and is in a transparent state when a voltage is applied.
  • the liquid crystal composition in the present invention contains a liquid crystal, a polymerizable compound, and a specific compound represented by the formula [1].
  • a liquid crystal nematic liquid crystal, smectic liquid crystal, or cholesteric liquid crystal can be used.
  • a liquid crystal having positive dielectric anisotropy is preferable for the normal type element, and a liquid crystal having negative dielectric anisotropy is preferably used for the reverse type element.
  • those having a large dielectric anisotropy and a large refractive index anisotropy are preferred.
  • two or more kinds of liquid crystals can be mixed and used according to the respective physical property values of the phase transition temperature, dielectric anisotropy and refractive index anisotropy.
  • liquid crystal display element As an active element such as a TFT (Thin Film Transistor), it is required that the liquid crystal has a high electric resistance and a high voltage holding ratio (also referred to as VHR). For this reason, it is preferable to use a fluorine-based or chlorine-based liquid crystal that has high electrical resistance and does not lower VHR by active energy rays such as ultraviolet rays.
  • active energy rays such as ultraviolet rays.
  • the liquid crystal display element can be made into a guest-host type element by dissolving a dichroic dye in a liquid crystal composition.
  • a dichroic dye in the case of a normal type element, an element that is absorbed (scattered) when no voltage is applied and is transparent when a voltage is applied can be obtained.
  • the direction of the liquid crystal director in this element, changes by 90 degrees depending on the presence or absence of voltage application. Therefore, this element can obtain a higher contrast than the conventional guest-host type element that switches between random alignment and vertical alignment by utilizing the difference in light absorption characteristics of the dichroic dye.
  • a guest-host type element in which a dichroic dye is dissolved is colored when the liquid crystal is aligned in the horizontal direction, and is opaque only in the scattering state. Therefore, as the voltage is applied, it is possible to obtain an element that switches from colored and opaque when no voltage is applied to colored and colorless and transparent.
  • the polymerizable compound in the liquid crystal composition is for forming a polymer network (also referred to as a curable resin) by a polymerization reaction by irradiation with ultraviolet rays at the time of producing a liquid crystal display element. Therefore, a polymer obtained by polymerizing a polymerizable compound in advance may be introduced into the liquid crystal composition. However, even when a polymer is used, it is necessary to have a site that undergoes a polymerization reaction upon irradiation with ultraviolet rays.
  • a liquid crystal composition containing a polymerizable compound is preferably used from the viewpoint of handling of the liquid crystal composition, that is, suppressing the increase in viscosity of the liquid crystal composition and solubility in the liquid crystal.
  • the polymerizable compound is not particularly limited as long as it dissolves in the liquid crystal, but when the polymerizable compound is dissolved in the liquid crystal, it is necessary that a temperature at which a part or the whole of the liquid crystal composition exhibits a liquid crystal phase exists. Even when a part of the liquid crystal composition exhibits a liquid crystal phase, it is sufficient that the liquid crystal display element is confirmed with the naked eye and the entire element has substantially uniform transparency and scattering characteristics.
  • the polymerizable compound is not particularly limited as long as it is a compound that is polymerized by ultraviolet rays. At that time, the polymerization may proceed in any reaction form to form a curable resin.
  • Specific reaction formats include radical polymerization, cationic polymerization, anionic polymerization, or polyaddition reaction. Among these, radical polymerization is preferable as the reaction mode of the polymerizable compound from the viewpoint of the optical characteristics of the liquid crystal display element. In that case, the following radical type polymerizable compounds or oligomers thereof can be used as the polymerizable compound. Further, as described above, a polymer obtained by polymerizing these polymerizable compounds can also be used. Specific examples of the radical type polymerizable compound or oligomer thereof include the radical type polymerizable compounds described on pages 69 to 71 of International Publication No. WO2015 / 146987.
  • the use ratio of the radical type polymerizable compound or oligomer thereof is preferably 70 to 150 parts by mass with respect to 100 parts by mass of the liquid crystal in the liquid crystal composition from the viewpoint of adhesion between the liquid crystal layer and the electrode of the liquid crystal display element. . More preferred is 80 to 110 parts by mass.
  • the radical type polymerizable compound may be used alone or in combination of two or more depending on each characteristic.
  • a radical initiator that generates radicals by ultraviolet rays also referred to as a polymerization initiator
  • a radical initiator that generates radicals by ultraviolet rays
  • a radical initiator that generates radicals by ultraviolet rays
  • Specific examples include radical initiators described on pages 71 to 72 of International Publication No. 2015/146987.
  • the use ratio of the radical initiator is preferably 0.01 to 20 parts by mass with respect to 100 parts by mass of the liquid crystal in the liquid crystal composition from the viewpoint of adhesion between the liquid crystal layer and the electrode of the liquid crystal display element. More preferred is 0.05 to 10 parts by mass.
  • a radical initiator can also be used 1 type or in mixture of 2 or more types according to each characteristic.
  • the specific compound is a compound represented by the formula [1].
  • X 1 , X 2 , Xm and Xn are as defined above, and among them, the following are preferable.
  • X 1 is preferably the formula [1-a] or the formula [1-b].
  • X 2 is preferably an alkylene group having 2 to 12 carbon atoms, and any —CH 2 — not adjacent to X 1 and O may be substituted with —O—, —COO— or —OCO—.
  • Xm is preferably an integer of 1 or 2.
  • Xn is preferably an integer of 1 or 2. However, Xm + Xn is 3.
  • Specific examples of the specific compound include compounds selected from the group consisting of the following formulas [1a-1] to [1a-3], and these are preferably used.
  • Xa represents the formula [1-a] or the formula [1-b].
  • X b represents an alkylene group having 2 to 18 carbon atoms.
  • X c represents —COO— or —OCO—.
  • X d represents an alkylene group having 2 to 12 carbon atoms.
  • p1 represents an integer of 1 or 2.
  • p2 represents an integer of 1 or 2.
  • p1 + p2 is 3.
  • p3 represents an integer of 2 to 8.
  • the liquid crystal composition in the present invention preferably contains a compound represented by the following formula [2] (also referred to as a second specific compound).
  • Y 1 represents the following formulas [2-a] to [2-j]. Of these, the formula [2-a], the formula [2-b], the formula [2-c], the formula [2-d], the formula [2-e], or the formula [2-f] is preferable. Formula [2-a], formula [2-b], formula [2-c] or formula [2-e] is more preferred, and formula [2-a] or formula [2-b] is most preferred.
  • Y A represents a hydrogen atom or a benzene ring.
  • Y 2 is a single bond, —O—, —NH—, —N (CH 3 ) —, —CH 2 O—, —CONH—, —NHCO—, —CON (CH 3 ) —, —N (CH 3 ) CO—, —COO— or —OCO— is shown.
  • a single bond, —O—, —CH 2 O—, —CONH—, —COO— or —OCO— is preferable, and a single bond, —O—, —COO— or —OCO— is more preferable.
  • Y 3 represents a single bond or — (CH 2 ) a — (a is an integer of 1 to 15). Among these, a single bond or — (CH 2 ) a — (a is an integer of 1 to 10) is preferable, and — (CH 2 ) a — (a is an integer of 1 to 10) is particularly preferable.
  • Y 4 represents a single bond, —O—, —OCH 2 —, —COO— or —OCO—. Of these, a single bond, —O— or —COO— is preferable, and —O— is particularly preferable.
  • Y 5 represents a divalent cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, or a divalent organic group having 17 to 51 carbon atoms having a steroid skeleton, and any hydrogen atom on the cyclic group is It may be substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxy group having 1 to 3 carbon atoms, or a fluorine atom.
  • a divalent organic group having 17 to 51 carbon atoms having a benzene ring, a cyclohexane ring, or a steroid skeleton is preferable. More preferred is a C 17-51 divalent organic group having a benzene ring or a steroid skeleton.
  • Y 6 represents a single bond, —O—, —CH 2 —, —OCH 2 —, —CH 2 O—, —COO— or —OCO—.
  • a single bond, —O—, —COO— or —OCO— is preferable, and a single bond, —COO— or —OCO— is more preferable.
  • Y 7 represents a cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, and any hydrogen atom on these cyclic groups is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, carbon It may be substituted with a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxy group having 1 to 3 carbon atoms, or a fluorine atom. Of these, a benzene ring or a cyclohexane ring is preferable.
  • Y 8 represents an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, or a fluorine-containing alkoxy group having 1 to 18 carbon atoms. Indicates a group. Of these, an alkyl group having 1 to 18 carbon atoms or an alkoxy group, or an alkenyl group having 2 to 18 carbon atoms is preferable. More preferred is an alkyl group having 1 to 12 carbon atoms or an alkoxy group.
  • Ym represents an integer of 0 to 4. Of these, an integer of 0 to 2 is preferable. Preferred combinations of Y 1 to Y 8 and Ym in the formula [2] are shown in Tables 1 to 9 below. In Tables 1 to 9, a in — (CH 2 ) — representing Y 3 represents an integer of 1 to 10.
  • More specific examples of the second specific compound include compounds selected from the group consisting of the following formulas [2a-1] to [2a-11], and these are preferably used.
  • Y c represents a single bond, —COO— or —OCO—.
  • Y d represents an alkyl group or alkoxy group having 1 to 12 carbon atoms.
  • q3 represents an integer of 1 to 10.
  • q4 represents an integer of 1 or 2.
  • Y e represents —O— or —COO—.
  • Y f represents a divalent organic group having 17 to 51 carbon atoms and having a steroid skeleton.
  • Y g represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 18 carbon atoms.
  • q5 represents an integer of 1 to 10.
  • the content ratio of the second specific compound is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the liquid crystal in the liquid crystal composition in terms of adhesion between the liquid crystal layer and the electrode of the liquid crystal display element. More preferred is 5 to 20 parts by mass, and most preferred is 1 to 10 parts by mass.
  • the 2nd specific compound can also be used 1 type or in mixture of 2 or more types according to each characteristic.
  • Examples of the method for preparing the liquid crystal composition include a method of mixing a liquid crystal, a polymerizable compound, and a specific compound together, and a method of mixing a polymerizable compound and a specific compound in advance with a liquid crystal. .
  • the second specific compound is prepared by adding a polymerizable compound and a specific compound to a liquid crystal, or by previously preparing a liquid crystal in which the second specific compound is added, and adding the polymerizable compound and the specific compound to the liquid crystal.
  • the method of adding to the mixture is mentioned.
  • it can also heat according to the solubility of a polymeric compound, a specific compound, and a 2nd specific compound.
  • the temperature at that time is preferably less than 100 ° C.
  • a liquid crystal alignment film for vertically aligning liquid crystal molecules is attached to at least one of the substrates.
  • the liquid crystal alignment film is prepared by applying a liquid crystal alignment treatment agent on a substrate and baking it. At that time, an orientation treatment such as rubbing treatment or light irradiation may be performed after firing.
  • the liquid crystal composition used in the liquid crystal display element is as described above, and a spacer for controlling the electrode gap (also referred to as a gap) of the liquid crystal display element can be introduced therein.
  • the method for injecting the liquid crystal composition is not particularly limited, and examples thereof include the following method. That is, when a glass substrate is used as a substrate, prepare a pair of substrates, apply a sealant to four pieces of the substrate on one side, except for a part, and then place the electrode surface on the inside, An empty cell on which the substrates are bonded is manufactured. And the method of injecting a liquid-crystal composition under reduced pressure from the place where the sealing agent is not apply
  • liquid crystal display element of the present invention since the adhesion between the liquid crystal layer and the electrode is high, it is not necessary to apply the sealing agent to the four pieces of the substrate.
  • the gap of the liquid crystal display element can be controlled by the above spacers.
  • Examples of the method include a method of introducing a spacer having a target size into the liquid crystal composition and a method using a substrate having a column spacer of a target size as described above.
  • the gap can be controlled without introducing a spacer.
  • the size of the gap of the liquid crystal display element is preferably 1 to 100 ⁇ m, more preferably 1 to 50 ⁇ m, and particularly preferably 2 to 30 ⁇ m. If the gap is too small, the contrast of the liquid crystal display element is lowered. If the gap is too large, the driving voltage of the element is increased.
  • the liquid crystal display element is obtained by curing the liquid crystal composition and forming a liquid crystal layer.
  • the liquid crystal composition is cured by irradiating the liquid crystal composition injection cell with ultraviolet rays.
  • the light source include a metal halide lamp and a high-pressure mercury lamp.
  • the wavelength of ultraviolet rays is preferably 250 to 400 nm, more preferably 310 to 370 nm. Further, heat treatment may be performed after irradiation with ultraviolet rays.
  • the temperature at that time is preferably 20 to 120 ° C, more preferably 30 to 100 ° C.
  • the liquid crystal display element before this treatment was cut with a wavelength of 350 nm or less using a metal halide lamp with an illuminance of 20 mW / cm 2 and irradiated with ultraviolet rays for an irradiation time of 60 seconds. Thereby, a liquid crystal display element (glass substrate) was obtained.
  • Table 10 summarizes the measurement results of Haze in the initial stage, after storage in a constant temperature and humidity chamber (constant temperature and humidity) and after irradiation with ultraviolet rays (ultraviolet rays).
  • the liquid crystal display element (glass substrate and plastic substrate) is stored in a constant temperature and humidity chamber at a temperature of 80 ° C. and a humidity of 90% RH for 24 hours, and the liquid crystal display element is peeled off and the presence or absence of bubbles is confirmed.
  • As a stability test of the liquid crystal display device in a high temperature and high humidity environment Specifically, the case where no peeling of the element (the liquid crystal layer and the resin film or the state where the resin film and the electrode are peeled off) and the case where no bubbles are generated in the element are excellent in this evaluation. (Good indication in the table).
  • the liquid crystal display element was confirmed by irradiating it with ultraviolet rays of 5 J / cm 2 in terms of a wavelength of 365 nm using a desktop UV curing device (HCT3B28HEX-1, manufactured by Senlite) (light of the liquid crystal display element).
  • a stability test against irradiation Specifically, the case where no peeling of the element occurred and the case where no bubbles were generated in the element were considered to be excellent in this evaluation (good indication in the table).
  • Table 11 summarizes the results of adhesion between the liquid crystal layer and the electrode (adhesion) after initial storage in a constant temperature and humidity chamber (constant temperature and humidity) and after ultraviolet irradiation (ultraviolet light).
  • Examples 1 to 8 and Comparative Examples 1 and 2 As shown in Table 10 and Table 11 below, using the liquid crystal compositions (1) to (5), liquid crystal display elements were prepared by the above method, and optical characteristics (scattering characteristics and transparency) were evaluated. The adhesion between the liquid crystal layer and the electrode was evaluated. At that time, in Examples 1, 3, 5, 7 and Comparative Example 1, a liquid crystal display element was prepared and evaluated using a glass substrate. In Examples 2, 4, 6, 8 and Comparative Example 2, plastic was used. A substrate was used.
  • the liquid crystal display elements of the examples have better optical characteristics than the comparative examples, that is, the Haze of the initial stage after storage in a constant temperature and humidity chamber and after ultraviolet irradiation. Change is small. Furthermore, a liquid crystal display element having high adhesion between the liquid crystal layer and the electrode was obtained, and even after being exposed to these harsh environments, peeling and bubbles were not observed in the liquid crystal display element. In particular, these characteristics were good even when a plastic substrate was used as the substrate of the liquid crystal display element. Specifically, in comparison under the same conditions, the comparison between Examples 1 and 3 and Comparative Example 1, and the comparison between Examples 2 and 4 and Comparative Example 2. Further, when the second specific compound was introduced into the liquid crystal composition, the haze was lowered at a lower voltage. Specifically, in comparison under the same conditions, comparison is made between Example 3 and Example 5, and comparison between Example 4 and Example 6.
  • the liquid crystal display element of the present invention can be suitably used for a normal type element that is in a scattering state when no voltage is applied and becomes transparent when a voltage is applied.
  • the element can be used for a liquid crystal display for display purposes, as well as a light control window and an optical shutter element for controlling the blocking and transmission of light.
  • a substrate can be used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Mathematical Physics (AREA)
  • Dispersion Chemistry (AREA)
  • Liquid Crystal (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention fournit un élément d'affichage à cristaux liquides qui augmente l'adhérence entre une couche de cristaux liquides et une électrode, et qui permet d'inhiber le pelage de l'élément et l'apparition de bulles, et une baisse de caractéristiques optiques, y compris dans un environnement exposé à des températures et une humidité élevées et à une irradiation lumineuse, sur une longue période. Plus précisément, l'invention concerne un élément d'affichage à cristaux liquides qui possède une couche de cristaux liquides obtenue par durcissement sous l'effet d'une irradiation au moyen d'un rayonnement ultraviolet sur une composition de cristaux liquides contenant des cristaux liquides disposés entre une paire de substrats comportant une électrode, et un composé polymérisable, et qui se trouve dans un état de diffusion lorsqu'il n'y a aucune application de tension, et dans un état de transparence lorsqu'une tension est appliquée. Cet élément d'affichage à cristaux liquides est caractéristique en ce que ladite composition de cristaux liquides contient un composé représenté par la formule ［１］. (Chacun des symboles mentionnés dans la formule est défini dans la description.)
PCT/JP2019/011259 2018-03-20 2019-03-18 Élément d'affichage à cristaux liquides WO2019181882A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2020507805A JP7226428B2 (ja) 2018-03-20 2019-03-18 液晶表示素子
KR1020207029717A KR20200130435A (ko) 2018-03-20 2019-03-18 액정 표시 소자
CN201980019741.5A CN111868615A (zh) 2018-03-20 2019-03-18 液晶表示元件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-052661 2018-03-20
JP2018052661 2018-03-20

Publications (1)

Publication Number Publication Date
WO2019181882A1 true WO2019181882A1 (fr) 2019-09-26

Family

ID=67987383

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/011259 WO2019181882A1 (fr) 2018-03-20 2019-03-18 Élément d'affichage à cristaux liquides

Country Status (5)

Country Link
JP (1) JP7226428B2 (fr)
KR (1) KR20200130435A (fr)
CN (1) CN111868615A (fr)
TW (1) TW201947023A (fr)
WO (1) WO2019181882A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022118745A1 (fr) * 2020-12-04 2022-06-09 日産化学株式会社 Élément d'affichage à cristaux liquides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09316032A (ja) * 1993-02-12 1997-12-09 Dainippon Ink & Chem Inc アクリレート化合物とそれを用いた液晶デバイス
CN105418854A (zh) * 2015-12-30 2016-03-23 石家庄诚志永华显示材料有限公司 一种具有高粘接力pdlc的组合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4630954Y1 (fr) 1964-12-26 1971-10-26
JPS552328A (en) 1978-06-20 1980-01-09 Toshiba Corp Field system controller of synchronous motor
JP2885116B2 (ja) 1994-07-05 1999-04-19 日本電気株式会社 液晶光学素子およびその製造方法
JP4132424B2 (ja) 1999-06-22 2008-08-13 旭硝子株式会社 液晶光学素子の製造方法
WO2010092954A1 (fr) 2009-02-13 2010-08-19 日立化成工業株式会社 Film de modulation de lumière
CN106662780B (zh) * 2014-06-25 2019-12-31 日产化学工业株式会社 液晶表示元件
US10647816B2 (en) 2014-09-25 2020-05-12 Nissan Chemical Industries, Ltd. Liquid crystal display device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09316032A (ja) * 1993-02-12 1997-12-09 Dainippon Ink & Chem Inc アクリレート化合物とそれを用いた液晶デバイス
CN105418854A (zh) * 2015-12-30 2016-03-23 石家庄诚志永华显示材料有限公司 一种具有高粘接力pdlc的组合物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022118745A1 (fr) * 2020-12-04 2022-06-09 日産化学株式会社 Élément d'affichage à cristaux liquides

Also Published As

Publication number Publication date
KR20200130435A (ko) 2020-11-18
CN111868615A (zh) 2020-10-30
JPWO2019181882A1 (ja) 2021-03-18
TW201947023A (zh) 2019-12-16
JP7226428B2 (ja) 2023-02-21

Similar Documents

Publication Publication Date Title
US9671650B2 (en) Method for manufacturing liquid crystal display device
TW200422715A (en) Liquid crystal display and method of manufacturing the same
JPH1036847A (ja) 液晶表示素子およびその製造方法
WO2011004519A1 (fr) Écran à cristaux liquides, et procédé de production correspondant
US20210261864A1 (en) Material for liquid-crystal device, and liquid-crystal device
JP5113869B2 (ja) 液晶表示装置及びその製造方法
WO2020184420A1 (fr) Composition de résine, film de résine et élément d'affichage à cristaux liquides
JP2016110148A (ja) 液晶素子、液晶組成物、液晶素子を用いたスクリーン及びディスプレイ
WO2011004518A1 (fr) Écran à cristaux liquides, et procédé de production correspondant
JP6398163B2 (ja) 液晶素子、該液晶素子を用いたスクリーン及びディスプレイ、並びに液晶組成物
CN111198452B (zh) 液晶显示器件
JP2012220673A (ja) 液晶光学装置、及びその製造方法
JP7226428B2 (ja) 液晶表示素子
WO2022118745A1 (fr) Élément d'affichage à cristaux liquides
US20190085243A1 (en) Negative liquid crystal material, liquid crystal cell, and liquid crystal display
JP7310796B2 (ja) 液晶表示素子
TWI697550B (zh) 液晶組成物及液晶光學元件
WO2017110704A1 (fr) Dispositif d'affichage à cristaux liquides et procédé de fabrication de dispositif d'affichage à cristaux liquides
CN111198459A (zh) 液晶显示器件
WO2017145917A1 (fr) Dispositif d'affichage à cristaux liquides et son procédé de fabrication
JP7424363B2 (ja) 樹脂組成物、樹脂膜及び液晶表示素子
JP7226429B2 (ja) 液晶表示素子
JP4756325B2 (ja) 液晶表示素子および液晶表示素子の製造方法
JP2005352415A (ja) 表示素子および表示装置
JP5007770B2 (ja) 液晶表示素子および液晶表示素子の製造方法

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: 19770840

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2020507805

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20207029717

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 19770840

Country of ref document: EP

Kind code of ref document: A1