WO2015182926A1 - Nouveau composé mésogène biréactif - Google Patents

Nouveau composé mésogène biréactif Download PDF

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Publication number
WO2015182926A1
WO2015182926A1 PCT/KR2015/005132 KR2015005132W WO2015182926A1 WO 2015182926 A1 WO2015182926 A1 WO 2015182926A1 KR 2015005132 W KR2015005132 W KR 2015005132W WO 2015182926 A1 WO2015182926 A1 WO 2015182926A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
formula
mesogenic compound
direactive
present
Prior art date
Application number
PCT/KR2015/005132
Other languages
English (en)
Korean (ko)
Inventor
최진욱
송정인
강소희
Original Assignee
주식회사 동진쎄미켐
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
Priority claimed from KR1020150067032A external-priority patent/KR20150139430A/ko
Application filed by 주식회사 동진쎄미켐 filed Critical 주식회사 동진쎄미켐
Publication of WO2015182926A1 publication Critical patent/WO2015182926A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • 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
    • 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
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to a direactive mesogen compound having an alkyl group in a linkage group located between both reactive groups.
  • Liquid crystal displays have the widest market share among various types of flat panel display technologies developed to date by injecting liquid crystals between two transparent electrode substrates and arranging liquid crystals by electric fields.
  • the driving methods used in the liquid crystal display are largely divided into three types, such as twisted nematic (TN), vertical alignment (VA), and in-plane switching (IPS).
  • TN twisted nematic
  • VA vertical alignment
  • IPS in-plane switching
  • the method of arranging the liquid crystal molecules and the movement of the liquid crystal molecules according to the voltage vary according to the driving method such as TN, VA, and IPS.
  • the difference in driving method has a great influence on the viewing angle and response speed, and various techniques have been developed to meet these characteristics, such as low viscosity, mechanical thermal stability, and efforts to increase the curing rate of mesogen compounds.
  • US Patent Publication No. 2005-0133760 discloses a mesogen group between two polymerizable groups
  • US Patent Publication No. 2014-0085709 describes a mesogen compound which does not include a -COO- group in the polymerizable group
  • Korean Patent Laid-Open Publication No. 2006-0063763 discloses reactive mesogen compositions in which polymerizable groups are disposed on the left and right sides, but despite the improvement of physical properties of known reactive mesogen compounds, they still have low viscosity, thermal stability and fast response speed. The need for it is pointed out.
  • the present invention provides a novel direactive mesogenic compound of the formula (1).
  • X 1 to X 9 are each independently selected from H or F or methacrylate or acrylate, provided that at least one of X 5 to X 9 must be methacrylate or acrylate, m1 and m2 are each Independently 0 to 5 and not 0 at the same time, A is selected from a single bond, -O-, -COO-, -OCO-, and n is an integer of 2 to 5;
  • the present invention provides novel direactive mesogenic compounds of formula (I).
  • X 1 to X 9 are, each independently, H or F, or meta is selected from an acrylate or acrylate, with the proviso that, X 5 to X 9 of the must, one or more meta be an acrylate or acrylate, m1, m2 are each Independently 0 to 5 and not 0 at the same time, A is selected from a single bond, -O-, -COO-, -OCO-, and n is an integer of 2 to 5;
  • X 5 to X 9 are methacrylate or acrylate, it is a photoreactor in which the reactive mesogen compound is substantially activated by light, and the reactive mesogen compound is polymerized by activation of the photoreactor. Can be.
  • the pretilt angle of the VA type liquid crystal composition used together may be maintained by curing the photoreactive mesogen compound. Therefore, when the voltage is applied or released, the response speed of the VA type liquid crystal composition is increased. It is an invention that the response speed is faster than that of a VA type liquid crystal composition in the case of not using a gen compound.
  • One feature of the present invention is that-(CH 2 ) n-, which is a space group disposed between both direactive groups, has 2 to 5 alkyl groups.
  • the ethane group of the space group has the advantage of being able to exhibit low viscosity.
  • the ethane group of the space group may have a linear chain shape.
  • the linear chain carbon atoms may be composed of a single bond by an alkyl group to each other.
  • Another feature of the present invention is that it has a structure in which F is substituted for a benzene ring having both reactive groups bonded thereto.
  • the polymerizable mesogen compound used in the PSA or PS-VA type liquid crystal display must not only have high photoreaction efficiency but also have high solubility with the host liquid crystal because the liquid crystal cell is prepared by mixing with the host liquid crystal.
  • the present invention improves the solubility in liquid crystal by introducing fluorine into the benzene ring.
  • the present invention connected the spacer group by an ethane bond, and F was substituted in the benzene ring of both reactive groups, thereby showing excellent black visibility and high liquid crystal response speed.
  • the present invention may exhibit a remarkable liquid crystal response speed when the direactive mesogen compound of Chemical Formula 1 is mixed in the alignment layer composition.
  • the liquid crystal response speed was remarkably improved than that of the liquid crystal composition or the alignment layer composition. It confirmed with 5 msec.
  • Another feature of the present invention is the linkage group for both the space group and the space group reactive group or It is characterized by connecting to.
  • the -A- functional group is characterized in that a single bond or selected from -O-, -COO-, -OCO- to connect.
  • m1 and m2 are 0-5, except the case of 0 at the same time.
  • Preferred direactive mesogenic compounds according to the present invention are added in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the liquid crystal composition having negative dielectric anisotropy, or 0.1 to 30 parts by weight based on 100 parts by weight of the total vertical alignment agent, After the photoreaction, the viscosity of the host liquid crystal is effective to improve the response speed without significantly changing.
  • reaction mixture was poured into a vessel mixed with water (100 ml) and toluene (100 ml) and stirred for 10 minutes. After separating the water layer and the organic solvent layer, all the organic solvent was evaporated. The resulting mixture was separated by column chromatography (solvent: toluene) to give a white solid (10 g, 88%).
  • 1,2-bis ((2 ', 3'-difluoro-4'-methoxy- [1,1'-biphenyl] -4-yl) oxyl) ethane (6 g) at -78 degrees; 100 ml) and 1.5-fold excess BBr3 (60 ml) is added. Raised to room temperature and stirred for 24 hours. After completion of the reaction, the layers were separated using water (150 ml) and ether (750 ml), and extracted with 2N NaOH. The extracted alkaline solution was acidified with dilute HCl until the pH became 1. The precipitate was filtered off and recrystallized with acetic acid to give a white solid product. (68%)
  • the pretilt angle of the VA type liquid crystal composition used together may be maintained by curing the photoreactive direactive mesogen compound, whereby the response speed of the VA type liquid crystal composition is increased when a voltage is applied or released. It is an invention that the response speed is faster than that of a VA type liquid crystal composition in the case of not using a photoreactive direactive mesogen compound.
  • Liquid crystal composition having a negative dielectric constant compound of the formula 2, 6 di-reactive mesogenic compound of the present invention (30-50% non-polar compound without halogen substitution, negative dielectric constant polar compound fluorine-substituted in the side chain of some benzene ring 70-50 %) The liquid crystal composition mixed at a ratio of 0.5 parts by weight to 100 parts by weight was injected into the pattern cell in which the upper and lower sides became the ITO electrode, and the measurement sample was injected therebetween, and the response speed which was an electro-optical characteristic was evaluated.
  • the cell spacing of the liquid crystal layer was about 3 ⁇ m
  • the exposure voltage for photocuring the direactive mesogen compound was 3.5V
  • the intensity of ultraviolet light was about 5J in the field exposure.
  • T on is the response time when VA type liquid crystal is horizontally oriented when voltage is applied and the light receiving amount changes from 10% to 90%
  • T off is the light receiving amount changing from 90% to 10% when the voltage is released. The response time is measured.
  • the present invention relates to a reactive mesogen compound having an ethane group in a space group located between both reactive groups, which can realize low viscosity, is mechanically and thermally stable, and can control the diameter of the liquid crystal. It exhibits black visibility and high liquid crystal response speed, and as the free radicals are stably maintained due to the planar structure of the reactive mesogen composed of ethane and phenyl groups, the curing time of the reactive mesogen is increased to shorten the manufacturing time of the liquid crystal display panel.
  • the present invention provides a liquid crystal display panel, wherein the reactive mesogen polymerized by light is polymerized and formed.
  • the viscosity of the mixed liquid crystal in the PS-PVA mode is effective to improve the response speed and is effective in improving the black visibility in the SC-PVA mode.
  • the present invention is a photopolymerizable monomer developed in the present invention irrespective of the number of phenyl groups, the number of alkyl groups, the number and position of F is a liquid crystal cell of VA (vertical aligned) mode, such as PS-PVA, SC-PVA mode Applicable in

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

Abstract

L'objectif de la présente invention concerne un nouveau composé mésogène biréactif présentant un temps de réponse rapide et un grand angle de vue, le nouveau composé mésogène biréactif étant représenté par la formule chimique 1. La présente invention, qui concerne un composé mésogène réactif présentant un groupe alkyle dans un groupe d'espacement positionné entre des groupes réactifs à l'une ou l'autre extrémité correspondante, permet la réalisation d'une faible viscosité, est mécaniquement et thermiquement stable, permet l'ajustement de l'angle de préinclinaison de cristaux liquides, présente une excellente visibilité dans l'obscurité et une grande vitesse de réponse des cristaux liquides, maintient de façon stable des radicaux libres en raison de la structuration plane de mésogènes réactifs constitués d'éthane et d'un groupe phényle, ce qui permet de réduire le temps de fabrication d'un panneau d'affichage à cristaux liquides et d'augmenter la qualité correspondante par l'augmentation de la vitesse de durcissement des mésogènes réactifs et permet d'obtenir un panneau d'affichage à cristaux liquides caractérisé en ce qu'il est formé par la polymérisation de mésogènes réactifs, qui sont polymérisés par la lumière. En particulier, la présente invention est efficace pour améliorer une vitesse de réponse tout en ne modifiant pas de manière significative la viscosité d'un mélange de cristaux liquides dans un mode PS-PVA, lorsqu'il présente un groupe éthane en tant que groupe de liaison, et est également efficace pour améliorer la visibilité dans l'obscurité dans un mode SC-PVA. En outre, le monomère photopolymérisable selon la présente invention est applicable dans une cellule à cristaux liquides dans un mode d'alignement vertical (VA), tel que les modes PS-PVA et SC-PAV, quels que soient le nombre de groupes phényle, le nombre de groupes alkyle et le nombre et la position de Fs.
PCT/KR2015/005132 2014-05-30 2015-05-22 Nouveau composé mésogène biréactif WO2015182926A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2014-0065701 2014-05-30
KR20140065701 2014-05-30
KR10-2015-0067032 2015-05-14
KR1020150067032A KR20150139430A (ko) 2014-05-30 2015-05-14 신규 이반응성 메소게닉 화합물

Publications (1)

Publication Number Publication Date
WO2015182926A1 true WO2015182926A1 (fr) 2015-12-03

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017134841A1 (fr) * 2016-02-02 2017-08-10 Dic株式会社 Élément d'affichage à cristaux liquides et son procédé de production
WO2017217311A1 (fr) * 2016-06-17 2017-12-21 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
US11248170B2 (en) 2017-04-21 2022-02-15 Jiangsu Hecheng Display Technology Co., Ltd. Polymerizable compound and application thereof
JP2022119164A (ja) * 2021-02-03 2022-08-16 株式会社Ｊａｃｔａコラボレーション 化合物、化合物を含有する液晶組成物、及び、液晶組成物を使用した液晶表示素子
CN114920631A (zh) * 2021-02-03 2022-08-19 杰科达谘询有限公司 化合物、含有化合物的液晶组合物、和使用液晶组合物的液晶显示元件

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100129406A (ko) * 2009-06-01 2010-12-09 삼성전자주식회사 액정표시패널의 제조 방법 및 액정표시패널
KR20130017938A (ko) * 2011-08-12 2013-02-20 주식회사 동진쎄미켐 중합성 액정 조성물
US20130277609A1 (en) * 2012-04-24 2013-10-24 Jnc Petrochemical Corporation Compound having four polymerizable groups, liquid crystal composition and liquid crystal display device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100129406A (ko) * 2009-06-01 2010-12-09 삼성전자주식회사 액정표시패널의 제조 방법 및 액정표시패널
KR20130017938A (ko) * 2011-08-12 2013-02-20 주식회사 동진쎄미켐 중합성 액정 조성물
US20130277609A1 (en) * 2012-04-24 2013-10-24 Jnc Petrochemical Corporation Compound having four polymerizable groups, liquid crystal composition and liquid crystal display device

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017134841A1 (fr) * 2016-02-02 2017-08-10 Dic株式会社 Élément d'affichage à cristaux liquides et son procédé de production
US20190025656A1 (en) * 2016-02-02 2019-01-24 Dic Corporation Liquid crystal display element and method for producing same
WO2017217311A1 (fr) * 2016-06-17 2017-12-21 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
JPWO2017217311A1 (ja) * 2016-06-17 2018-06-28 Dic株式会社 液晶組成物及び液晶表示素子
US11248170B2 (en) 2017-04-21 2022-02-15 Jiangsu Hecheng Display Technology Co., Ltd. Polymerizable compound and application thereof
JP2022119164A (ja) * 2021-02-03 2022-08-16 株式会社Ｊａｃｔａコラボレーション 化合物、化合物を含有する液晶組成物、及び、液晶組成物を使用した液晶表示素子
CN114920631A (zh) * 2021-02-03 2022-08-19 杰科达谘询有限公司 化合物、含有化合物的液晶组合物、和使用液晶组合物的液晶显示元件
JP7297269B2 (ja) 2021-02-03 2023-06-26 株式会社Ｊａｃｔａコラボレーション 化合物、化合物を含有する液晶組成物、及び、液晶組成物を使用した液晶表示素子

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