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
  • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
  • C09K19/60—Pleochroic dyes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
  • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
  • C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
  • C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
  • C07C225/34—Amino anthraquinones
  • C07C225/36—Amino anthraquinones the carbon skeleton being further substituted by singly-bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C229/68—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
  • C07C229/72—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the carbon skeleton being further substituted by doubly-bound oxygen atoms
  • C07C229/74—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the carbon skeleton being further substituted by doubly-bound oxygen atoms the condensed ring system being formed by at least three rings, e.g. amino anthraquinone carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
  • C09B1/51—N-substituted amino-hydroxy anthraquinone
  • C09B1/514—N-aryl 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
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
  • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
• • 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
• • 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

Definitions

• the present inventors have succeeded in obtaining a novel anthraquinone compound with a specific structure.
• the present inventors have also found that a light modulating device with excellent light resistance can be obtained by using a liquid crystal composition containing such a dichroic dye, which is a novel anthraquinone compound with a specific structure. . That is, aspects or embodiments included in the present invention are as follows. [1].
• the content of the anthraquinone compound represented by formula (1) in the liquid crystal composition is not particularly limited, but is preferably 0.5 to 15 parts by mass, more preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the liquid crystal material. Parts by mass are more preferable.
• a dichroic dye (described later) other than the compound represented by the formula (1)
• the anthraquinone compound represented by the formula (1) and the dichroic dye other than the compound represented by the formula (1) is preferably within the above range (0.5 to 15 parts by mass) with respect to 100 parts by mass of the liquid crystal material.
• the mixing ratio of the total liquid crystal material and the photocurable compound is preferably in the above range (90:10 to 50:50 in mass ratio), and the more preferred range and the more preferred range are also the same as above.
• cured product By irradiating the composition of the present invention containing a photocurable compound and a photopolymerization initiator with light, a cured product of the liquid crystal composition in which the photocurable compound component is cured (polymerized) can be obtained.
• cured product means a state in which the functional groups of the photocurable compound are polymerized or copolymerized by irradiation with light, and the anthraquinone compound represented by the formula (1), liquid crystal material, or the like is not necessarily It does not mean a cured product that contributed to the curing reaction.
• the light source for light irradiation is not particularly limited as long as it can irradiate light having a wavelength that is absorbed by the photopolymerization initiator.
• Preferred light sources include high-pressure mercury lamps, metal halide lamps, xenon lamps and halogen lamps capable of irradiating ultraviolet rays.
• the light modulating element can be used by sandwiching it between a pair of flat or curved glass, hard plastic, or the like via an adhesive layer such as polyvinyl butyral, vinyl acetate, double-sided tape, or adhesive.
• the light modulating element can be used by attaching it to a sheet of flat or curved glass, hard plastic, or the like with a double-faced tape, an adhesive, or the like.
• it may be sandwiched between soft plastics or stuck on one side or both sides.
• the resulting crude product was dissolved in toluene, and column purification was performed using toluene as a developing solvent.
• the solvent was distilled off from the purified solution under reduced pressure, and dried in a hot air dryer at 50°C for 24 hours to obtain No. 1 of the above specific example. 0.11 parts of the compound represented by 12 were obtained as a dark brown solid.
• the maximum absorption wavelength of this compound in toluene was 651 nm.
• the resulting crude product was dissolved in toluene, and column purification was performed using toluene as a developing solvent.
• the solvent was distilled off from the purified solution under reduced pressure, and dried in a hot air dryer at 50°C for 24 hours to obtain No. 1 of the above specific example.
• 0.1 part of the compound represented by 18 was obtained as a dark brown solid.
• the maximum absorption wavelength of this compound in toluene was 651 nm.
• Example 11 (Synthesis of the Anthraquinone Compound of the Present Invention Represented by Specific Example No. 24) 0.9 parts of the compound represented by the following formula (21) to 20 parts of NMP, 0.025 parts of copper powder, 0.025 parts of copper iodide, 2.0 parts of 2-iodobenzotrifluoride, 0.02 parts of potassium carbonate and 0.15 parts of sodium acetate were added, and the mixture was stirred at 150 to 160°C for 12 hours, then the reaction solution was cooled to 25°C, 200 parts of methanol was added, and the mixture was further stirred for 1 hour. The reaction product was collected by filtration, washed with methanol, and dried with a hot air dryer at 50° C. for 24 hours.
• Example 14 (Synthesis of the Anthraquinone Compound of the Present Invention Represented by Specific Example No. 35) 0.9 parts of the compound represented by the following formula (24) in 20 parts of NMP, 0.025 parts of copper powder, 0.025 parts of copper iodide, 2.5 parts of 3-fluoro-4-iodobenzonitrile, potassium carbonate 0 0.02 part and 0.15 part of sodium acetate were added and stirred at 150 to 160° C. for 12 hours, then the reaction mixture was cooled to 25° C. and 200 parts of methanol was added and stirred for an additional hour. The reaction product was collected by filtration, washed with methanol, and dried with a hot air dryer at 50° C. for 24 hours.
• a light control liquid crystal element having high contrast and high light resistance can be obtained by using a liquid crystal composition containing the compound.
• Such a light modulating element can be suitably used for outdoor building material applications and in-vehicle applications that require high durability.

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

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• 2022
  • 2022-10-14 TW TW111139107A patent/TW202330459A/zh unknown
  • 2022-10-14 WO PCT/JP2022/038309 patent/WO2023063408A1/ja not_active Ceased
  • 2022-10-14 JP JP2023554640A patent/JPWO2023063408A1/ja active Pending
  • 2022-10-14 US US18/698,038 patent/US12312294B2/en active Active
  • 2022-10-14 EP EP22881103.0A patent/EP4417597A4/en active Pending
  • 2022-10-14 CN CN202280068623.5A patent/CN118103349A/zh active Pending

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