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WO2014065560A1 - Composé de cristaux liquides sous la forme d'un dendron et son procédé de préparation - Google Patents

Composé de cristaux liquides sous la forme d'un dendron et son procédé de préparation Download PDF

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Publication number
WO2014065560A1
WO2014065560A1 PCT/KR2013/009411 KR2013009411W WO2014065560A1 WO 2014065560 A1 WO2014065560 A1 WO 2014065560A1 KR 2013009411 W KR2013009411 W KR 2013009411W WO 2014065560 A1 WO2014065560 A1 WO 2014065560A1
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WIPO (PCT)
Prior art keywords
liquid crystal
crystal compound
dendron
group
formula
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Ceased
Application number
PCT/KR2013/009411
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English (en)
Korean (ko)
Inventor
정광운
이명훈
이승용
국윤배
김인수
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.)
Industry Academic Cooperation Foundation of Chonbuk National University
Original Assignee
Industry Academic Cooperation Foundation of Chonbuk National University
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Publication of WO2014065560A1 publication Critical patent/WO2014065560A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • 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
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3475—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing at least three 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
    • C09K19/38—Polymers
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • C09K19/3842—Polyvinyl derivatives
    • C09K19/3852—Poly(meth)acrylate derivatives
    • 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
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/122—Ph-Ph

Definitions

  • the present invention relates to a liquid crystal compound in the form of a dendron and a method of manufacturing the same. More specifically, the present invention relates to a dendron-type liquid crystal compound having a plurality of physical bonds formed between molecules to increase the processability of the compound, and a method of manufacturing the same.
  • liquid crystal display devices As the performance of liquid crystal display devices is improved, the range of use has been extended to large TVs as well as PC monitors and portable information terminals. Accordingly, there is an increasing demand for low-cost, high-quality large-scale liquid crystal display devices. For this purpose, a wide viewing angle, high brightness, high speed response and high contrast of the liquid crystal display device must be implemented at low cost. In addition, as the area of liquid crystal display devices increases rapidly, a liquid crystal compound having excellent processability and excellent flexible performance is required.
  • the present invention provides a novel supramolecular compound having a physical binding force.
  • the present invention provides a liquid crystal compound having excellent workability in the form of dendron.
  • the present invention is to provide a liquid crystal compound having a high speed response to a wide viewing angle, high brightness, and an electric field.
  • One aspect of the present invention relates to a liquid crystal compound of a dendron structure represented by the following formula (1).
  • formula (1) [Formula 1]
  • Ar is an arylene group having 6 to 20 carbon atoms
  • L is COOR, COCOOR, COC1
  • R 1 and R 2 are hydrocarbon compounds having 1 to 30 carbon atoms, M is mesogen, and m is
  • the present invention is based on a liquid crystal display device containing the liquid crystal compound.
  • the liquid crystal compound of the dendron structure according to the present invention is the production of pulraek flexible element over a large area due to the excellent workability can be coated and printed.
  • the liquid crystal compound of the present invention can maximize the physical bonding force between the liquid crystal, and can form a high-dimensional structure by controlling this.
  • the liquid crystal compound of the dendron of the present invention is an excellent solubility in common solvents compared to conventional liquid crystal, the liquid crystal temperature range is formed more widely.
  • the dendron-like liquid crystal compound of the present invention can improve the arrangement of liquid crystal molecules when used as an additive in the liquid crystal layer, and the added dendron-type liquid crystal moves to the lower surface of the liquid crystal layer so that the alignment property is improved. I can improve it.
  • FIG. 1 is a graph of 1H NMR of 4- (4'-octyloxy) -hydroxybiphenyl synthesized.
  • Figure 2 is a graph of 1H NMR of the synthesized TrKethylene glycol) bis (p— toluenesulfonate).
  • FIG. 4 is a graph of 1H NMR of synthesized 3,4,5-tris [2— (2 ( ⁇ 2— [4— (4'-octyloxy) hydroxybiphenyl] ethoxy ⁇ ethoxy) ethoxy] benzoic acid methyl ester.
  • 5 is a graph of 1H NMR of synthesized 3,4,5-tris [2— (2- ⁇ 2— [4— (4'-octyloxy) hydroxybip.henyl] ethoxy) ethoxy) et ox-y] benzyl alcohol to be.
  • 6 is a graph of 1H VIR of 3,4,5-tris [2 ′ (2 ′ ⁇ 2- [4- (4′—octyloxy) hydroxybiphenyl] ethoxy ⁇ ethoxy) ethox-y] benzyl bromide synthesized.
  • 7 is a graph of IH NMR of synthesized 3,4,5 tris [2- (2- ⁇ 2- [4- (4'—octyloxy) hydroxybiphenyl] ethoxy ⁇ ethoxy) ethox-y] benzyl azide.
  • FIG. 11 is a graph of the synthesized IH NMR of 4- [2 ′ (2- ⁇ 2- [4- (4'-octyloxy) hydroxybiphenyl] ethoxy ⁇ et oxy) ethoxy] benzyl alcoh.
  • the present invention is a liquid crystal compound having a dendron structure represented by the following formula (1).
  • Ar is an arylene group having 6 to 20 carbon atoms
  • L is COOR, C0C00R, C0C1,
  • R1 and R2 are hydrocarbon compounds having 1 to 30 carbon atoms
  • M mesogen
  • M is 1 to 3.
  • Ar in Chemical Formula 1 may include at least one benzene ring compound and a fused benzene ring compound heterocyclic compound as an arylene group having 6 to 20 carbon atoms.
  • Ar may be substituted with N, S, or 0 in which one or more carbons have a lone pair of electrons.
  • An example of Ar may be represented by the following Chemical Formula 2.
  • Formula 1 may be specifically represented by the following formula (3). ⁇ 30> [Formula 3]
  • L may be substituted with a highly reactive element such as Br, C1, or F to the hydrocarbon compound.
  • L is COOR, C0C00R, C0C1, (CH2) nOH, (CH2) nBr, or (CH2) nN3, where R is hydrogen or an alkyl group of 1 to 3 carbon atoms, n may be 1-5 .
  • R 1 and R 2 are hydrocarbon compounds having 1 to 30 carbon atoms.
  • R 2 may be hydrophilic or hydrophobic.
  • R1 and R2 may be hydrophobic if the other is hydrophilic.
  • R1 and R2 may each be a linear alkyl group, a branched alkyl group, or an alkenyl group having 2 to 30 carbon atoms, and are also a linear alkyl group, a branched alkyl group, or an alkenyl group having 2 to 30 carbon atoms.
  • One or more carbons may be substituted with 0, S, N or F.
  • R1 and R2 are an alkylene group having 1 to 30 carbon atoms, an alkoxy group, a fluoroalkylene group, an ether group, a fluoroether group or ⁇ 0R3, wherein R3 is an alkylene group having 1 to 30, or fluoroalkylene It may be a flag.
  • the mesogen is represented by the following formula (4). [Formula 4]
  • A is-0-,-C00-, ⁇ 0C0 or-NHC0-
  • B is S, 0, N2 or (CH2) n, where n is 1-20.
  • the mesogen has liquid crystallinity by itself, and is excellent in self-assembly due to ⁇ - ⁇ interaction of benzene ring.
  • liquid crystal compound having the dendron structure may be represented by the following Chemical Formula 5.
  • An increase average molecular weight of the liquid crystal compound of the dendron structure may be 500 to 2,000.
  • the liquid crystal compound of the dendron structure can induce physical bonding between liquid crystals.
  • the liquid crystal compound includes a plurality of unshared electron pairs. For example, elements such as N, 0, F, and S are substituted in hydrocarbon chains or aromatic ring compounds to increase hydrogen bonds, ⁇ ⁇ ⁇ interactions, and hydrophilic ⁇ hydrophobic molecular forces. Enemies can be maximized in combination.
  • the compound of the dendron structure may form a supramolecular structure by inducing physical bonding between liquid crystals.
  • the liquid crystal compound may include all hydrophilic or hydrophobic hydrocarbon compounds or may be appropriately selected to provide a wide range of solvent selectivity and excellent processability.
  • the interaction between liquid crystal molecules may be increased, thereby forming a wider liquid crystal temperature range.
  • the present invention relates to a liquid crystal display device comprising the liquid crystal compound of the dendron structure.
  • the liquid crystal display device of the present invention is preferably applied to the vertical alignment mode.
  • the liquid crystal display of the present invention may include a lower substrate including a pixel electrode and a common electrode spaced apart from each other; an upper substrate disposed to face the lower substrate; and disposed between the upper substrate and the lower substrate; When an electric field is applied in an isotropic state in the absence of the electric field, the liquid crystal layer is changed to an anisotropic state; and a polarizing plate disposed to cross the upper substrate and the lower substrate.
  • the upper substrate, the lower substrate, the polarizer, the liquid crystal, and the like used in the present invention may use known methods, materials, and techniques, but there is no limitation thereto.
  • the lower substrate may include a thin film transistor formed in each pixel on the insulating substrate and a pixel electrode connected to the thin film transistor.
  • the upper substrate may have a chrome matrix in which a matrix of pixels substantially defining a pixel area on the insulating substrate.
  • the upper substrate includes a color filter formed below the black matrix to correspond to the pixel and a common electrode formed on the color filter.
  • the liquid crystal may be optically isotropic (preferably macro isotropic) when no electric field is applied, such as a material having a Pockels effect or a Kerr effect, and may be an optical anisotropy expressed by electric field addition. It may be a material having optical anisotropy in an electric field-free uncoated yarn, and the optical anisotropy is lost by applying an electric field, and thus is optically isotropic (preferably isotropic in view of macroscopic).
  • optically isotropic preferably macro isotropic
  • liquid crystal usable in the present invention 5CB (p-n pentyl-p'-cyanobiphenyl), JO1041 (chiso), etc. may be used, and as a chirai dopant,
  • ZLI-4572 (Merck), IS (60BA) 2, CB-15 and the like can be used.
  • the liquid crystal may use negative dielectric anisotropy.
  • the liquid crystal compound of the dendron structure may be used as an additive in the liquid crystal layer to improve the arrangement of liquid crystal molecules.
  • the dendron liquid crystal compound may be used in an amount of 0.1 to 30% by weight compared to the liquid crystal.
  • the liquid crystal compound of the dendron structure is formed on the upper, lower or upper surface of the liquid crystal layer.
  • the lower portion may be positioned at the same time to improve the alignment of the liquid crystal.
  • Formula 6 is an example of a dendron structure liquid crystal compound usable in the present invention.
  • M is mesogen and R 1 is CF 3 (CF 2) n CH 2 CH 20 H, CH 3 (CH 2) n Br,
  • LI is selected from benzene, carboxylic acid, acyl chloride, alcohol, alkyl bromide, or a Iky J azide
  • R2 is CKCH2) n (Br (CH2) nBr, HO (CH2) nOH, ClCH2 (CH20CH2) nCH2Cl, Cl (CF2) nCl, I (CF2) nI, Br (CF2) nBr, H0CH2 (CH20CH2) nCH20H, or EH0CH2 (CF2) nCH20H.
  • the method for preparing the liquid crystal compound is an alkyl chain of R 1 and a mesogen of M.
  • the compound which may be used as L1 may be selected from benzene, car boxy lie acid, acyl chloride, alcohol, alkyl bromide, or alkyl azide.
  • n 1 to 20.
  • 0H in Formula 7, 9, 10, and 15 may be substituted with tosylate.
  • N of Formula 18 is 3 to 10
  • n of Formula 19 is 3 to 12
  • n of Formula 20 is 2 to 12
  • n of Formula 21 is 1 to 7
  • n of Formula 22 is 3 to 8
  • N in formulas 23 and 24 are 2 to 8
  • n in formula 25 is 4 to 6, and n in formula 26 is 1 to 11.
  • 0H in Formulas 20 and 26 may be substituted with one or both of tosylate.
  • Compounds that can be used as M may be selected from Table 3 below.
  • 1 to 8 nitrogen may be positioned.
  • an alkyl group having 1 to 8 carbon atoms, not hydrogen, may be located in the meta, para position.
  • n may refer to the above description.
  • the present invention relates to a liquid crystal compound in the form of a dendron, and a method for manufacturing the same, which can be used in the liquid crystal production and manufacturing industry. '

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

Abstract

La présente invention concerne un composé de cristaux liquides, ayant une aptitude au traitement de composé améliorée par formation d'une liaison physique multiple entre des molécules, sous la forme d'un dendron et un procédé de préparation de celui-ci. Le composé de cristaux liquides ayant la structure d'un dendron, selon la présente invention, permet le revêtement et l'impression dus à l'excellente aptitude au traitement de celui-ci et permet ainsi la production d'éléments flexibles de grande surface. Le composé de cristaux liquides selon la présente invention peut former une structure dimensionnelle élevée en rendant maximale la force de la liaison physique entre les cristaux liquides et en la réglant. Le composé de cristaux liquides sous la forme d'un dendron selon la présente invention a une excellente solubilité dans un solvant général par comparaison avec des cristaux liquides classiques et a une plage de température de cristaux liquides plus large. Le composé de cristaux liquides sous la forme d'un dendron selon la présente invention peut améliorer la disposition de molécules de cristaux liquides lorsqu'il est utilisé comme additif pour une couche de cristaux liquides et peut également améliorer les propriétés d'orientation lorsque les cristaux liquides ajoutés sous la forme d'un dendron se déplacent vers la surface de fond de la couche de cristaux liquides.
PCT/KR2013/009411 2012-10-22 2013-10-22 Composé de cristaux liquides sous la forme d'un dendron et son procédé de préparation Ceased WO2014065560A1 (fr)

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KR1020120117031A KR101449139B1 (ko) 2012-10-22 2012-10-22 덴드론 형태의 액정화합물 및 그 제조방법
KR10-2012-0117031 2012-10-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019081389A1 (fr) * 2017-10-25 2019-05-02 Merck Patent Gmbh Milieu à cristaux liquides et dispositif à cristaux liquides

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102281268B1 (ko) * 2020-01-16 2021-07-23 전북대학교산학협력단 덴드론 구조의 나노컬럼, 이를 이용한 2축 필름 제조방법 및 이를 포함하는 2축 필름
KR102768406B1 (ko) 2022-12-02 2025-02-13 동명대학교산학협력단 자율제어 및 인공지능을 활용한 선박 고정용 위치 추적 시스템
KR102852959B1 (ko) 2023-04-05 2025-08-29 동명대학교산학협력단 선박의 동적 위치 자동 제어시스템

Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2002302674A (ja) * 2001-04-05 2002-10-18 Fuji Photo Film Co Ltd 液晶組成物、それを用いた液晶素子およびアゾ化合物
KR20050034462A (ko) * 2003-10-09 2005-04-14 제일모직주식회사 덴드론 구조의 측쇄를 가지는 디아민 화합물 및 이를이용하여 제조된 액정 배향재
JP2008088275A (ja) * 2006-09-29 2008-04-17 Dainippon Printing Co Ltd デンドリマー、デンドリマーの製造方法、及びレジスト組成物
JP2008201682A (ja) * 2007-02-16 2008-09-04 Kyushu Univ デンドロンとメソゲンとを有する化合物、液晶組成物及び光素子

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002302674A (ja) * 2001-04-05 2002-10-18 Fuji Photo Film Co Ltd 液晶組成物、それを用いた液晶素子およびアゾ化合物
KR20050034462A (ko) * 2003-10-09 2005-04-14 제일모직주식회사 덴드론 구조의 측쇄를 가지는 디아민 화합물 및 이를이용하여 제조된 액정 배향재
JP2008088275A (ja) * 2006-09-29 2008-04-17 Dainippon Printing Co Ltd デンドリマー、デンドリマーの製造方法、及びレジスト組成物
JP2008201682A (ja) * 2007-02-16 2008-09-04 Kyushu Univ デンドロンとメソゲンとを有する化合物、液晶組成物及び光素子

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019081389A1 (fr) * 2017-10-25 2019-05-02 Merck Patent Gmbh Milieu à cristaux liquides et dispositif à cristaux liquides

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KR101449139B1 (ko) 2014-10-16

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