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WO2015053505A1 - Composé mésogénique polymérisable à base de phényl-thiophène fluoré présentant une solubilité améliorée dans un cristal liquide hôte, son procédé de préparation, et composition de cristaux liquides polymérisable contenant celui-ci - Google Patents

Composé mésogénique polymérisable à base de phényl-thiophène fluoré présentant une solubilité améliorée dans un cristal liquide hôte, son procédé de préparation, et composition de cristaux liquides polymérisable contenant celui-ci Download PDF

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Publication number
WO2015053505A1
WO2015053505A1 PCT/KR2014/009182 KR2014009182W WO2015053505A1 WO 2015053505 A1 WO2015053505 A1 WO 2015053505A1 KR 2014009182 W KR2014009182 W KR 2014009182W WO 2015053505 A1 WO2015053505 A1 WO 2015053505A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
formula
thiophene
phenyl
polymerizable
Prior art date
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Ceased
Application number
PCT/KR2014/009182
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English (en)
Korean (ko)
Inventor
가재원
김진수
이미혜
김윤호
장광석
김희주
최진욱
이성규
조성찬
노경래
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongjin Semichem Co Ltd
Original Assignee
Dongjin Semichem Co Ltd
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Filing date
Publication date
Application filed by Dongjin Semichem Co Ltd filed Critical Dongjin Semichem Co Ltd
Priority to CN201480055587.4A priority Critical patent/CN105637064B/zh
Publication of WO2015053505A1 publication Critical patent/WO2015053505A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate

Definitions

  • the present invention relates to a fluorine-introduced phenyl-thiophene-based polymerizable mesogen compound having improved solubility in a host liquid crystal, a method for preparing the same, and a polymerizable liquid crystal composition comprising the same.
  • CRT Cathode Ray Tube
  • Typical flat panel displays to overcome the limitations of CRT monitors include liquid crystal displays (LCDs), plasma display panels (PDPs) and organic light emitting diodes (OLEDs).
  • LCDs liquid crystal displays
  • PDPs plasma display panels
  • OLEDs organic light emitting diodes
  • LCD liquid crystal display
  • LCD Liquid crystal display
  • PMP Portable Multimedia Player
  • MP3 Motion Picture Experts Group
  • MPEG Audio Layer-3
  • liquid crystal displays include liquid crystal cells and polarizing plates.
  • the polarizing plate consists of a protective film and a polarizing film, which can be prepared by laminating a polarizing film made of a polyvinyl alcohol film with iodine, stretching, and laminating both sides with a protective film.
  • the polarizing plates may be mounted on both sides of the liquid crystal cell, or may be manufactured by arranging an optical compensation sheet having one or more optically anisotropic layers.
  • a reflective liquid crystal display LCD
  • a reflective plate, a liquid crystal cell, one or more optical compensation sheets, and a polarizing plate may be disposed in the order of manufacturing.
  • the liquid crystal cell is composed of liquid crystal molecules, two substrates for encapsulating it, and an electrode layer for applying a voltage to the liquid crystal molecules.
  • the liquid crystal cell can display ON / OFF due to the difference in the alignment state of the liquid crystal molecules, and can be applied to both the transmissive type and the reflective type, so that TN (Twisted nematic), IPS (in-plane switching), and OCB (Optically Compensatory Bend)
  • TN Transmission nematic
  • IPS in-plane switching
  • OCB Optically Compensatory Bend
  • Various types of liquid crystal displays have been developed, such as Vertically Aligned (VA), Electrically Controlled Birefringence (ECB), and Super Twisted Nematic (STN).
  • VA Vertically Aligned
  • EBCB Electrically Controlled Birefringence
  • STN Super Twisted Nematic
  • each of these types has a unique liquid crystal array and has inherent optical anisotropy. Therefore, in order to compensate for the change in the optical axis of linearly polarized light due to the optical anisotropy of these liquid crystal types, various optical anisotropy
  • the liquid crystal compound which has a polymeric group can be applied to optical elements, such as a polarizing plate and a retardation plate.
  • optical elements such as a polarizing plate and a retardation plate.
  • Such an optical element can be obtained by polymerizing a polymerizable liquid crystal having optical anisotropy in a liquid crystal state and immobilizing the polymer liquid crystal.
  • the polymerizable liquid crystal thus prepared can be polymerized while maintaining an alignment state by performing proper alignment control in a liquid crystal state. Can be. Therefore, a polymer having various optical anisotropy can be obtained by fixing the alignment state of the liquid crystal skeleton to a state such as homogeneous alignment, hybrid alignment, oblique alignment, homeotropic alignment, twist alignment, or the like.
  • the liquid crystal compound having a polymerizable group is a polymer stabilized alignment (PSA: Polymer Stabilized Aligned) or a polymer stabilized vertical alignment (PS-VA) among VA type liquid crystal displays widely used in high-end monitors and large TVs. Can be used for liquid crystal displays.
  • PSA Polymer Stabilized Aligned
  • PS-VA polymer stabilized vertical alignment
  • a liquid crystal display liquid crystal cell of the conventional VA type includes a host liquid crystal having negative dielectric anisotropy between two transparent electrodes, and in the off state where no voltage is applied, these liquid crystal molecules are oriented perpendicular to the electrode surface. In the on state where a voltage is applied to the electrode, the liquid crystal molecules are aligned parallel to the electrode surface.
  • the opening and closing of the light from the backlight passing through the polarizer can be controlled according to the vertical and horizontal alignment of the liquid crystal according to the presence or absence of voltage, but the response speed is very high if the direction of parallel alignment when the voltage is applied to the electrode is not determined in advance. There are disadvantages.
  • PSA or PS-VA which is one of VA types, is a method for controlling the inclination of vertically aligned liquid crystals in a liquid crystal cell, and mixes a mesogenic compound that can be polymerized by ultraviolet rays with a host liquid crystal in the liquid crystal cell.
  • the photoreactive mesogen compound to be used must move together in the direction in which the host liquid crystal lies when voltage is applied to the electrode through interaction with the vertically aligned liquid crystal.
  • the induction is inclined and then cured through light irradiation, a constant inclination is maintained even when no voltage is applied.
  • the host liquid crystal is rapidly oriented in the inclination direction, thereby realizing a high-speed response.
  • 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. Furthermore, an appropriate core is required to provide stability to the pretilt angle of the mesogen compound inclined in the lying direction of the host liquid crystal.
  • a liquid crystal display device comprising an alignment film having an alignment base film oriented to have a pretilt and a double layer of an alignment control film having a polymerized mesogen represented by the following formula (Patent Document 1):
  • P 1 and P 2 are independently selected from acrylate, methacrylate and the like.
  • a 1 and A 2 are independently selected from 1,4-phenylene and naphthalene-2,6-diyl).
  • Patent Document 2 a novel mesogen compound represented by the following formula has been disclosed.
  • Patent Document 3 a polymer stabilized liquid crystal composition characterized by containing a compound represented by the following formula
  • 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. Furthermore, an appropriate core is required to provide stability to the pretilt angle of the mesogen compound inclined in the lying direction of the host liquid crystal.
  • the present inventors have been researching with interest for mesogenic compounds having high photoreaction efficiency, and the phenyl-thiophene-based polymerizable mesogen compound having a fluorine group is excellent in solubility in host liquid crystals, and thus photocrosslinking is possible.
  • the present invention has been completed by revealing that it can be usefully used as a polymerizable liquid crystal composition for liquid crystal display of polymer stabilized alignment type since it has an effect of improving the stability of the post-tilt angle.
  • An object of the present invention is to provide a phenyl-thiophene-based polymerizable mesogenic compound with improved solubility in the host liquid crystal.
  • Another object of the present invention is to provide a method for preparing the phenyl-thiophene-based polymerizable mesogen compound.
  • Another object of the present invention is to provide a polymerizable liquid crystal composition comprising the phenyl-thiophene-based polymerizable mesogen compound.
  • the present invention provides a phenyl-thiophene-based polymerizable mesogenic compound represented by Formula 1 below:
  • a phenyl-thiophene-based polymerizable mesogenic compound represented by Chemical Formula 1 which comprises dissolving a compound represented by Chemical Formula 8 and a compound represented by Chemical Formula 9 in an organic solvent and then reacting to prepare a compound represented by Chemical Formula 1.
  • the present invention provides a polymerizable liquid crystal composition
  • a polymerizable liquid crystal composition comprising a phenyl-thiophene-based polymerizable mesogen compound represented by Chemical Formula 1.
  • a polymer stabilized alignment liquid crystal display comprising a liquid crystal layer containing the polymerizable liquid crystal composition of the present invention.
  • the phenyl-thiophene-based polymerizable mesogen compound of the present invention is asymmetrically introduced into the phenyl-thiophene core as a solubility enhancer to increase the solubility for the vertically aligned host liquid crystal and to introduce methacrylate as a photoreactive group. Since there is an effect of improving the stability of the pretilt angle after light crosslinking, it can be usefully used as a polymerizable liquid crystal composition, in particular, a polymerizable liquid crystal composition for liquid crystal display of the polymer stabilized alignment type.
  • FIG. 1 is a photograph taken after dissolving the phenyl-thiophene-based polymerizable mesogen compound of Examples 1 to 6 according to the present invention in MLC-6608 (Merck, Inc.), which is a vertically aligned host liquid crystal.
  • the present invention provides a phenyl-thiophene-based polymerizable mesogenic compound represented by Formula 1 below:
  • X is O, NH or S
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen or fluorine (F), wherein at least one of them is fluorine.
  • the phenyl-thiophene-based polymerizable mesogenic compound represented by Formula 1 is any one selected from the group consisting of compounds represented by Formulas 2 to 7:
  • X is O, NH or S.
  • the phenyl-thiophene-based polymerizable mesogen compound represented by the formula (1) is a compound in which the substituent X of the compound represented by the formulas (2) to (7) is O.
  • a phenyl-thiophene-based polymerizable mesogenic compound represented by Chemical Formula 1 which comprises dissolving a compound represented by Chemical Formula 8 and a compound represented by Chemical Formula 9 in an organic solvent and then reacting to prepare a compound represented by Chemical Formula 1.
  • X is O, NH or S
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen or fluorine (F), wherein at least one of them is fluorine.
  • a compound represented by Chemical Formula 1 by dissolving a compound represented by Chemical Formula 8 and a compound represented by Chemical Formula 9 in an organic solvent and reacting It can manufacture.
  • the organic solvent may be carried out under a conventional organic solvent. Any solvent capable of dissolving each reactant well may be selected and used without limitation, and may be used alone or in combination.
  • the organic solvent for example, dichloromethane (DCM), dimethylformamide (DMF), dimethylacetylamide (DMAc), dimethyl sulfoxide (DMSO), tetrahydrofuran (THF) and the like. It is possible to use, preferably dichloromethane (DCM) can be used.
  • the base catalyst may be any conventional base as long as it is a base capable of improving reaction activity or reaction rate, and preferably, ammonia, pyridine, trimethylamine (TMA), and triethylamine (TEA).
  • DMA Dimethylamine
  • DEA diethylamine
  • DIPEA N, N-diisopropylethylamine
  • N-methylporporin N-methylpiperidine
  • DMAP di Methylaminopyridine
  • TMEDA tetramethylethylenediamine
  • DMAP N, N-dimethylaminopyridine
  • the present invention provides a polymerizable liquid crystal composition
  • X is O, NH or S
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen or fluorine (F), wherein at least one of them is fluorine.
  • the present invention also provides a polymer stabilized alignment liquid crystal display having a liquid crystal layer comprising the polymerizable liquid crystal composition.
  • the polymer stabilized alignment liquid crystal display according to the present invention is preferably a liquid crystal display of vertical alignment type (VA-MODE).
  • the phenyl-thiophene-based polymerizable mesogen compound into which the fluorine group is introduced according to the present invention has a remarkably excellent solubility in the host liquid crystal, and thus the polymerizable liquid crystal composition for liquid crystal display of the polymer stabilized alignment type controlling the inclination of the host liquid crystal It can be usefully used.
  • Step 2 5- (4'-methoxyphenyl) -2- (pinacolboronyl) thiophene synthesis
  • reaction temperature was lowered to ⁇ 78 ° C., and bis (pinacolato) diborone (4.8 g, 18.9 mmol) was dissolved in tetrahydrofuran (30 mL), added to the reaction solution, and then heated at room temperature for 12 hours. Was stirred.
  • the polymerizable mesogenic compounds of Examples 1 to 6 are photographed whether they are dissolved with the host liquid crystal, and are shown in FIG. 1 and visually observed to melt very well-( ⁇ ), when slightly heated to melt-(O) and If it does not melt-it is represented in Table 1 as indicated by (X).
  • the phenyl-thiophene-based polymerizable mesogen compound incorporating the fluorine group of the present invention has excellent solubility with respect to the host liquid crystal, so that the polymerizable liquid crystal composition for liquid crystal display of polymer stabilized alignment type which controls the inclination of the host liquid crystal. It can be usefully used.
  • the phenyl-thiophene-based polymerizable mesogen compound incorporating the fluorine group of the present invention can be usefully used as a polymerizable liquid crystal composition for a liquid crystal display of a polymer stabilized alignment type that controls the inclination of a host liquid crystal.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Liquid Crystal Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne : un composé mésogénique polymérisable à base de phényl-thiophène fluoré présentant une solubilité améliorée dans un cristal liquide hôte ; son procédé de préparation ; et une composition de cristaux liquides polymérisable contenant celui-ci. Le composé mésogénique polymérisable à base de phényl-thiophène selon la présente invention augmente la solubilité dans un cristal liquide hôte aligné verticalement en introduisant de manière asymétrique un groupe fluoré comme groupe améliorant la solubilité dans un cœur phényl-thiophène et introduit un méthacrylate comme groupe photosensible, améliorant ainsi la stabilité d'un angle de pré-inclinaison après photoréticulation, et peut donc être utile comme composition de cristaux liquides polymérisable, en particulier une composition de cristaux liquides polymérisable destinée à une unité d'affichage à cristaux liquides à alignement stabilisé par un polymère.
PCT/KR2014/009182 2013-10-10 2014-09-30 Composé mésogénique polymérisable à base de phényl-thiophène fluoré présentant une solubilité améliorée dans un cristal liquide hôte, son procédé de préparation, et composition de cristaux liquides polymérisable contenant celui-ci Ceased WO2015053505A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480055587.4A CN105637064B (zh) 2013-10-10 2014-09-30 在主液晶中的溶解度得到提高的氟化的苯基噻吩系聚合性介晶化合物、其制造方法及包含其的聚合性液晶组合物

Applications Claiming Priority (2)

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KR1020130120618A KR101512173B1 (ko) 2013-10-10 2013-10-10 호스트 액정에 대한 용해도가 향상된 불소 도입 페닐-싸이오펜계 중합성 메조겐 화합물, 이의 제조방법 및 이를 포함하는 중합성 액정 조성물
KR10-2013-0120618 2013-10-10

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WO2015053505A1 true WO2015053505A1 (fr) 2015-04-16

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WO (1) WO2015053505A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112266794B (zh) * 2020-09-30 2022-09-09 北京八亿时空液晶科技股份有限公司 一种含噻吩的液晶化合物及其制备方法和应用
CN113249130B (zh) * 2021-05-17 2023-06-02 Tcl华星光电技术有限公司 液晶介质组合物、显示面板及其制备方法
CN113480515B (zh) * 2021-06-17 2022-09-09 Tcl华星光电技术有限公司 反应单体及其制备方法、显示面板的制作方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030062509A1 (en) * 2001-07-25 2003-04-03 Merck Patent Gmbh Mono-, oligo- and poly-3-(1,1-difluoroalkyl)thiophenes and their use as charge transport materials
US20070246704A1 (en) * 2004-06-09 2007-10-25 Martin Heeney Polymerisable ThienO[3,2-B]Thiophenes
KR20110117427A (ko) * 2010-04-21 2011-10-27 한국화학연구원 중합성 액정 화합물 및 폴리머
KR20130092816A (ko) * 2012-02-13 2013-08-21 (주)켐넥스 반응성 메소젠 화합물, 이를 포함하는 액정 조성물, 표시 패널의 제조 방법 및 표시 패널

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030062509A1 (en) * 2001-07-25 2003-04-03 Merck Patent Gmbh Mono-, oligo- and poly-3-(1,1-difluoroalkyl)thiophenes and their use as charge transport materials
US20070246704A1 (en) * 2004-06-09 2007-10-25 Martin Heeney Polymerisable ThienO[3,2-B]Thiophenes
KR20110117427A (ko) * 2010-04-21 2011-10-27 한국화학연구원 중합성 액정 화합물 및 폴리머
KR20130092816A (ko) * 2012-02-13 2013-08-21 (주)켐넥스 반응성 메소젠 화합물, 이를 포함하는 액정 조성물, 표시 패널의 제조 방법 및 표시 패널

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CN105637064A (zh) 2016-06-01
KR101512173B1 (ko) 2015-04-16
CN105637064B (zh) 2018-07-13

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