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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
  • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
  • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
  • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
  • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
  • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
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  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
  • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
  • C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
  • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
  • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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  • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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  • 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
  • C09K19/345—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 two nitrogen atoms
  • C09K19/3458—Uncondensed pyrimidines
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• • 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
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  • 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
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  • 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
  • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
  • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
  • C09K2019/181—Ph-C≡C-Ph
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  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
  • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
  • C09K2019/3004—Cy-Cy
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  • C09K19/3001—Cyclohexane rings
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  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
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  • C09K2019/3016—Cy-Ph-Ph
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  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
  • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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  • C09K19/3001—Cyclohexane rings
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• • 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 
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  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
  • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
• • G—PHYSICS
  • G02—OPTICS
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  • 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
  • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
• • 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
  • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
  • G02F1/13775—Polymer-stabilized liquid crystal layers

Definitions

• the present invention relates to a polymerizable compound, a polymerizable composition containing the polymerizable compound and a liquid crystal composition, a liquid crystal composite prepared from the polymerizable composition, and a liquid crystal display element.
• the liquid crystal display element utilizes the optical anisotropy and dielectric anisotropy of the liquid crystal molecules in the liquid crystal composition.
• the classification based on the operation mode of the liquid crystal molecule includes the PC (phase change) mode, TN (twisted nematic) mode, STN (super twisted nematic) mode, BTN (bistable twisted nematic) mode, ECB (electrically controlled birefringence) mode, OCB (Optically-compensated-bend) mode, IPS (in-plane switching) mode, FFS (fringe field switching) mode, VA (vertical alignment) mode, and the like.
• the initial alignment is achieved by a polyimide alignment film.
• a liquid crystal composition containing a polar compound and a polymer or a polymerizable polar compound is used.
• a small amount of a polar compound and a small amount of a polymerizable compound or a composition to which a small amount of a polymerizable polar compound is added are injected into the device.
• liquid crystal molecules may be aligned by the action of the polar compound.
• the composition is irradiated with ultraviolet rays.
• the polymerizable compound or the polymerizable polar compound is polymerized.
• the liquid crystal molecules are aligned and stabilized.
• the orientation after implantation is stabilized.
• the orientation of liquid crystal molecules can be controlled by the polar compound and the polymer or the polymerizable polar compound, the response time of the device is shortened, and image burn-in is improved.
• the step of forming the alignment film is unnecessary. Since there is no alignment film, the electrical resistance of the device does not decrease due to the interaction between the alignment film and the composition.
• Such an effect by the combination of the polar compound and the polymer can be expected for a device having a mode such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
• a method of combining a polymer with a liquid crystal composition can be applied to liquid crystal display elements of various operation modes, and modes such as PS-TN, PS-IPS, PS-FFS, PSA-VA, and PSA-OCB are known. ing.
• the polymerizable compound used in the element of such a mode is required to have excellent properties such as the ability to align liquid crystal molecules, appropriate polymerization reactivity, high conversion, and high solubility in a liquid crystal composition.
• Various polymerizable compounds have been developed so far, and it is desired to develop a compound that further improves the above characteristics.
• the first object of the present invention is to provide a polymerizable compound having the ability to align excellent liquid crystal molecules, suitable polymerization reactivity, high conversion, and high solubility in a liquid crystal composition.
• the second issue is the high upper limit temperature of the nematic phase, the lower lower limit temperature of the nematic phase, small viscosity, appropriate optical anisotropy, large dielectric anisotropy, suitable elastic constant, large specific resistance, suitable pretilt, etc.
• An object of the present invention is to provide a liquid crystal composite having an appropriate balance regarding at least two physical properties.
• a third problem is to provide a liquid crystal display element having a wide temperature range in which the element can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — is —O— or —S—. And at least one — (CH 2 ) 2 — may be replaced with —CH ⁇ CH—, and in these groups, at least one hydrogen may be replaced with a halogen.
• the first advantage of the present invention is to provide a polymerizable compound having the ability to align excellent liquid crystal molecules, suitable polymerization reactivity, high conversion, and high solubility in a liquid crystal composition.
• the second advantage is that the liquid crystal composite has a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant, and a large specific resistance. Satisfying at least one of physical properties such as an appropriate pretilt.
• the advantage is that the liquid crystal composite has an appropriate balance with respect to at least two physical properties.
• a third advantage is that the liquid crystal display device has a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
• Liquid crystalline compounds include non-polymerizable compounds having a liquid crystal phase such as a nematic phase and a smectic phase, and liquid crystal compositions having no liquid crystal phase, such as maximum temperature, minimum temperature, viscosity, and dielectric anisotropy. It is a general term for non-polymerizable compounds that are mixed for the purpose of adjusting. This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod-like.
• the liquid crystal composition is a mixture of liquid crystal compounds.
• the polymerizable compound is a compound added to the composition for the purpose of forming a polymer.
• the polymerizable composition is a mixture of a polymerizable compound, a liquid crystal composition, an additive, and the like.
• the liquid crystal composite is a composite formed by polymerization of this polymerizable composition.
• a liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module.
• the upper limit temperature of the nematic phase is a phase transition temperature of the nematic phase-isotropic phase in the liquid crystal composition, polymerizable composition, or liquid crystal composite, and may be abbreviated as the upper limit temperature.
• the lower limit temperature of the nematic phase may be abbreviated as the lower limit temperature.
• Polymerization reactivity refers to the degree of ease with which the reactants polymerize. Conversion is the weight ratio of reactant consumed by a chemical reaction to reactant.
• the liquid crystal composition is prepared by mixing a liquid crystal compound.
• the ratio (content) of the liquid crystal compound is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition.
• Additives such as optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors are added to this composition as necessary. Is done.
• the ratio (addition amount) of the additive is represented by a weight percentage (% by weight) based on the weight of the liquid crystal composition, similarly to the ratio of the liquid crystal compound. Weight parts per million (ppm) may be used.
• the ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.
• the compound represented by formula (1) may be abbreviated as compound (1).
• At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as “compound (1)”.
• “Compound (1)” means one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. The same applies to compounds represented by other formulas.
• the line crossing the circle means that the P 1 -S 1 group can arbitrarily select the bonding position on the ring such as a six-membered ring or a condensed ring. This rule also applies to symbols such as P 2 -S 2 groups.
• symbols such as B 1 , C 1 , and D 1 surrounded by hexagons correspond to rings such as ring B 1 , ring C 1 , and ring D 1 .
• the symbol R 11 is used in a plurality of formulas such as formula (2) and formula (3). In these compounds, the two end groups represented by any two R 11 may be the same or different.
• equation (8) when i is 2, two D 1 exist in one equation. In this compound, the two rings represented by two D 1 may be the same or different. This rule also applies to D 1 when j is greater than 2. This rule also applies to other symbols such as the P 1 -S 1 group.
• the expression “at least one“ A ”may be replaced by“ B ”” means that when the number of “A” is one, the position of “A” is arbitrary, and the number of “A” is two. Even when there are more than two, it means that their positions can be freely selected without limitation.
• the expression “at least one A may be replaced by B, C or D” means that at least one A is replaced by B, at least one A is replaced by C, and at least 1 When one A is replaced with D, it means that a plurality of A are further replaced with at least two of B, C, and D.
• alkyl in which at least one —CH 2 — (or —CH 2 CH 2 —) may be replaced by —O— includes alkyl, alkenyl, alkoxy, alkoxyalkyl, alkoxy Alkenyl and alkenyloxyalkyl are included. Note that it is not preferable that two consecutive —CH 2 — are replaced by —O— to form —O—O—. In alkyl and the like, it is not preferable that —CH 2 — in the methyl moiety (—CH 2 —H) is replaced by —O— to become —O—H.
• 2-Fluoro-1,4-phenylene means the following two divalent groups.
• fluorine may be leftward (L) or rightward (R). This rule also applies to asymmetric bivalent groups derived from rings, such as tetrahydropyran-2,5-diyl.
• Halogen means fluorine, chlorine, bromine and iodine.
• a preferred halogen is fluorine or chlorine, and a more preferred halogen is fluorine.
• the present invention includes the contents described in the following section.
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by a halogen.
• Item 2. The polymerizable compound according to item 1, represented by formula (1).
• P 1 and P 2 are independently polymerizable groups; S 1 and S 2 are each independently a single bond or alkylene having 1 to 10 carbon atoms, in which at least one —CH 2 — is —O—, —CO—, —COO— or —OCO.
• At least one —CH 2 —CH 2 — may be replaced with —CH ⁇ CH— or —C ⁇ C—, and in these divalent groups, at least one hydrogen is May be substituted with halogen or alkyl of 1 to 3 carbons;
• R 4 and R 5 are independently hydrogen, halogen, —S 1 —P 1 , —S 2 —P 2 , or alkyl having 1 to 20 carbons, in which at least one —CH 2 — May be replaced with —O— or —S—, and at least one — (CH 2 ) 2 — may be replaced with —CH ⁇ CH—, in which at least one hydrogen is a halogen.
• a1 and a2 are independently 0, 1, 2, 3, or 4;
• the combined number of —S 1 —P 1 and —S 2 —P 2 is 1 to 8, and at least one of all —S 1 —P 1 and all —S 2 —P 2 is A monovalent group represented by formula (A),
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• Ring A 1 and Ring A 2 are independently derived from an alicyclic hydrocarbon having 3 to 18 carbon atoms, an aromatic hydrocarbon having 6 to 18 carbon atoms, or a heteroaromatic hydrocarbon having 3 to 18 carbon atoms.
• at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons, or 1 carbon.
• At least one hydrogen may be replaced with halogen
• Z 1 is a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, or —OCO—.
• At least one —CH 2 —CH 2 — may be —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, —C (CH 3 ) ⁇ C (CH 3 ) —, or —CH ⁇ CH— may be replaced, and in these divalent groups, at least one hydrogen may be replaced with a halogen; b1 is 0, 1, 2, or 3.
• Item 3. The polymerizable compound according to item 1, represented by any one of formulas (1-1-1) to (1-1-3).
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• R 4 is hydrogen, halogen, —S 1 —P 1 , or alkyl having 1 to 20 carbons, and in this alkyl, at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by a halogen;
• S 1 and S 2 are each independently a single bond or alkylene having 1 to 10 carbon atoms, in which at least one —CH 2 — is —O—, —CO—, —COO—, — or —OCO— may be substituted, and at least one —CH 2 —CH 2 — may be substituted with —CH ⁇ CH— or —C ⁇ C—, and in these divalent groups, at least one Hydrogen may be replaced by halogen or alkyl of 1 to 3 carbons;
• P 1 is a polymerizable group;
• Ring A 1 , Ring A 2 , and Ring A 3 are independently an alicyclic hydrocarbon having 3 to 18 carbon atoms, an aromatic hydrocarbon having 6 to 18 carbon atoms, or a heteroaromatic group having 3 to 18 carbon atoms.
• a divalent group derived from a hydrocarbon wherein at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons Or, in these monovalent hydrocarbon groups, at least one hydrogen may be replaced by a halogen;
• Z 1 and Z 2 are each independently a single bond or alkylene having 1 to 10 carbon atoms, in which at least one —CH 2 — is —O—, —CO—, —COO—, or — OCO— may be substituted, and at least one —CH 2 —CH 2 — represents —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, —C ( CH 3 ) ⁇ C (CH 3 ) —, or —CH ⁇ CH—, and in these divalent groups, at least one hydrogen may be replaced with a halogen.
• Item 4. The polymerizable compound according to item 1, represented by any one of formulas (1-1-4) to (1-1-6):
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• R 4 is hydrogen, halogen, —S 1 —P 1 , or alkyl having 1 to 20 carbons, and in this alkyl, at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by a halogen;
• S 1 is a single bond or alkylene having 1 to 10 carbon atoms, in which at least one —CH 2 — is replaced by —O—, —CO—, —COO—, — or —OCO—.
• at least one —CH 2 —CH 2 — may be replaced by —CH ⁇ CH— or —C ⁇ C—, and in these divalent groups, at least one hydrogen is halogen or carbon.
• Ring A 1 , Ring A 2 and Ring A 3 are independently an alicyclic hydrocarbon having 3 to 18 carbon atoms, an aromatic hydrocarbon having 6 to 18 carbon atoms, or a heteroaromatic carbon atom having 3 to 18 carbon atoms.
• Item 6. The polymerizable compound according to item 1, represented by formula (1-1-5).
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• R 4 is hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—, and at least one — ( CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• Ring A 1 and Ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, and at least one hydrogen on these rings is replaced by a halogen May be.
• Item 6. The polymerizable compound according to item 1, represented by formula (1-1-7).
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — may be replaced by —O— or —S—.
• At least one — (CH 2 ) 2 — may be replaced by —CH ⁇ CH—, in which at least one hydrogen may be replaced by halogen;
• Ring A 1 and Ring A 2 are independently 1,4-cyclohexylene, 1,4-phenylene, and at least one hydrogen on these rings may be replaced by halogen;
• Z 1 is a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH 2 — may be replaced by —O—, —CO—, —COO—, or —OCO—.
• At least one —CH 2 —CH 2 — may be —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, —C (CH 3 ) ⁇ C (CH 3 ) —, or —CH ⁇ CH—, and in these divalent groups, at least one hydrogen may be replaced with a halogen.
• Item 7 A polymerizable composition containing at least one polymerizable compound according to any one of items 1 to 6.
• Item 8 The polymerizable composition according to item 7, further comprising at least one compound selected from the group of compounds represented by formulas (2) to (4).
• R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or alkenyl, at least one —CH 2 — may be replaced by —O—.
• Ring B 1 , Ring B 2 , Ring B 3 , and Ring B 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro- 1,4-phenylene or pyrimidine-2,5-diyl;
• Z 11 , Z 12 and Z 13 are each independently a single bond, —CH 2 CH 2 —, —CH ⁇ CH—, —C ⁇ C—, or —COO—.
• Item 9. The polymerizable composition according to Item 7 or 8, further comprising at least one compound selected from the group of compounds represented by formulas (5) to (7).
• R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, in which at least one —CH 2 — may be replaced by —O—, and at least one hydrogen is May be replaced by fluorine;
• X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 , or —OCF 2 CHFCF 3 ;
• Ring C 1 , Ring C 2 and Ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyr
• Item 10 The polymerizable composition according to any one of Items 7 to 9, further comprising at least one compound selected from the group of compounds represented by Formula (8).
• R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, in which at least one —CH 2 — may be replaced by —O—, and at least one hydrogen is May be replaced by fluorine;
• X 12 is —C ⁇ N or —C ⁇ C—C ⁇ N;
• Ring D 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced with fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl Or pyrimidine-2,5-diyl;
• Z 17 represents a single bond, -CH 2 CH 2 -, - C ⁇ C -, - COO -, - CF 2 O -, - OCF 2 -,
• Item 11 A liquid crystal composite produced by polymerization of the polymerizable composition according to any one of items 7 to 10.
• Item 12. An optically anisotropic material produced by polymerization of the polymerizable composition according to any one of Items 7 to 10.
• Item 13 A liquid crystal display device comprising the polymerizable composition according to any one of items 7 to 10 or the liquid crystal composite according to item 11.
• Item 14 The polymerizable compound according to any one of items 1 to 6, at least one selected from the group consisting of the polymerizable composition according to any one of items 7 to 10, and the liquid crystal composite according to item 11. Use in two liquid crystal display elements.
• the present invention includes the following items.
• the present invention includes the following items.
• the polymerizable compound of the present invention will be described, and then the synthesis method, the polymerizable composition, the liquid crystal composite, and the liquid crystal display element will be described in this order.
• the polymerizable compound of the present invention has at least one monovalent group (A).
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — is —O— or —S—. And at least one — (CH 2 ) 2 — may be replaced with —CH ⁇ CH—, and in these groups, at least one hydrogen may be replaced with a halogen.
• the compound (1) since the compound (1) has a rod-like molecular structure similar to a liquid crystal compound, the solubility in the liquid crystal composition is high. Therefore, the compound (1) is suitable as a polymerizable compound necessary for a device having a PSA mode. Secondly, the compound (1) has appropriate polymerizability. Therefore, compound (1) can be stored stably. In the polymerization, the rate of the photoreaction can be easily controlled. Polymerization can be performed by appropriately irradiating ultraviolet rays. Does not require excessive UV light.
• the polymerizable group P preferred examples of the polymerizable group P, the linking group S, the ring A, and the bonding group Z are as follows. This example also applies to compounds subordinate to compound (1).
• Compound (1) can have its physical properties arbitrarily adjusted by appropriately combining these types of groups. Since there is no great difference in the physical properties of the compound, the compound (1) may contain an isotope such as 2 H (deuterium) and 13 C in an amount larger than the natural abundance.
• P 1 and P 2 are independently a polymerizable group.
• polymerizable groups are acryloyloxy, methacryloyloxy, acrylamide, methacrylamide, vinyloxy, vinylcarbonyl, oxiranyl, oxetanyl, 3,4-epoxycyclohexyl, or maleimide.
• at least one hydrogen may be replaced with fluorine, methyl, or trifluoromethyl.
• Preferred examples of the polymerizable group are acryloyloxy (P-1), vinyloxy (P-2), oxiranyl (P-3) or maleimide (A), wherein M 1 and M 2 are independently hydrogen , Fluorine, methyl, or trifluoromethyl, and R 1 and R 2 are the same as defined for the monovalent group represented by formula (A).
• S 1 and S 2 are each independently a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH 2 — is —O—, —CO—, —COO— or —OCO— may be substituted, and at least one —CH 2 —CH 2 — may be substituted with —CH ⁇ CH— or —C ⁇ C—, and in these divalent groups , At least one hydrogen may be replaced by halogen or alkyl having 1 to 3 carbon atoms.
• Particularly preferred examples include a single bond, —CH 2 —, —CH ⁇ CH—, —CH ⁇ CH—O—, —O—CH ⁇ CH—, —CH 2 CH 2 O—, or —OCH 2 CH 2 —. It is.
• the most preferred example is a single bond.
• the configuration of the double bond of —CH ⁇ CH— may be cis or trans. The trans type is preferable to the cis type.
• R 4 and R 5 are independently hydrogen, halogen, —S 1 —P 1 , —S 2 —P 2 , or alkyl having 1 to 20 carbons, and in this alkyl, at least One —CH 2 — may be replaced with —O— or —S—, and at least one — (CH 2 ) 2 — may be replaced with —CH ⁇ CH—, and in these groups, at least One hydrogen may be replaced with a halogen.
• a1 and a2 are independently 0, 1, 2, 3, or 4.
• —S 1 —P 1 or —S 2 —P 2 is a monovalent group involved in polymerization.
• the total number of —S 1 —P 1 and —S 2 —P 2 is 1 to 8.
• Preferred examples are 1 to 6, and more preferred examples are 1 to 3.
• the most preferred example is 1 or 2.
• At least one of all —S 1 —P 1 and all —S 2 —P 2 is a monovalent group represented by formula (A).
• R 1 and R 2 are independently hydrogen, halogen, or alkyl having 1 to 20 carbons, in which at least one —CH 2 — is —O— or —S—. And at least one — (CH 2 ) 2 — may be replaced with —CH ⁇ CH—, and in these groups, at least one hydrogen may be replaced with a halogen.
• Preferred R 1 or R 2 is methyl, ethyl, or hydrogen. More preferred R 1 or R 2 is hydrogen.
• ring A 1 and ring A 2 are independently an alicyclic hydrocarbon having 3 to 18 carbon atoms, an aromatic hydrocarbon having 6 to 18 carbon atoms, or a heteroaromatic having 3 to 18 carbon atoms. It is a divalent group derived by removing two hydrogens from a group hydrocarbon. In these divalent groups, at least one hydrogen is replaced with halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 1 to 12 carbons, or alkenyloxy having 1 to 12 carbons. In these monovalent hydrocarbon groups, at least one hydrogen may be replaced with a halogen. Further, ring A 1 has a1 hydrogens replaced with —S 1 —P 1 , and ring A 2 has a2 hydrogens replaced with —S 2 —P 2 .
• Examples of the alicyclic hydrocarbon are cyclopropane, cyclobutane, cyclohexane, cycloheptane, cyclooctane and the like represented by C n H 2n .
• Other examples are decahydronaphthalene and the like.
• Examples of aromatic hydrocarbons are benzene, naphthalene, anthracene, phenanthrene, fluorene, indane, indene, tetrahydronaphthalene and the like.
• Examples of heteroaromatic hydrocarbons are pyridine, pyrimidine, furan, pyran, thiophene, benzofuran and the like.
• hydrocarbons may be substituted with monovalent groups such as fluorine, chlorine and alkyl.
• Preferred examples of ring A 1 or ring A 2 are benzene, fluorobenzene, naphthalene, fluorene, or phenanthrene. Further preferred examples are benzene or naphthalene.
• Z 1 include a single bond, alkylene having 1 to 4 carbon atoms, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH.
• Further preferred examples are a single bond, ethylene, —COO—, —OCO—, —CH ⁇ CH—, —CH ⁇ CH—COO—, —OCO—CH ⁇ CH—, or —CH ⁇ CH—.
• the most preferred example is a single bond.
• b1 is 0, 1, 2, or 3.
• the compound has one ring represented by the ring A 1.
• the preferred ring A 1 is a divalent group derived by removing two hydrogens from a condensed ring such as naphthalene, anthracene, phenanthrene, benzene.
• the compound has a ring A 1 and a ring A 2 .
• preferred ring A 1 or ring A 2 is a divalent group derived from benzene substituted with a substituent such as benzene, fluorine or methyl.
• the compound has three rings of ring A 1 , ring A 2 and ring A 2 .
• Preferred ring A 1 or ring A 2 is a divalent group derived from benzene substituted with a substituent such as benzene or fluorine.
• MSG 1 (or MSG 2 ) is a monovalent organic group having at least one ring.
• the monovalent organic groups represented by a plurality of MSG 1 (or MSG 2 ) may be the same or different.
• Compounds (1A) to (1I) correspond to compound (1).
• esters a method for synthesizing a compound having —COO— was shown.
• a compound having —OCO— can also be synthesized by this synthesis method. The same applies to other asymmetrical linking groups.
• Arylboric acid (21) and a compound (22) synthesized by a known method are reacted in an aqueous carbonate solution in the presence of a catalyst such as tetrakis (triphenylphosphine) palladium.
• Compound (1A) is synthesized.
• This compound (1A) is prepared by reacting compound (23) synthesized by a known method with n-butyllithium and then with zinc chloride, and in the presence of a catalyst such as dichlorobis (triphenylphosphine) palladium. ) Is also reacted.
• a phosphorus ylide is prepared by reacting a base such as sodium hydride with ethyl diethylphosphonoacetate, and this phosphorus ylide is reacted with an aldehyde (32) to obtain an ester (33). .
• Ester (33) is hydrolyzed in the presence of a base such as sodium hydroxide to give carboxylic acid (34). This compound and compound (25) are dehydrated and condensed to synthesize compound (1F).
• Linking Group S P 1 or P 2 is a polymerizable group.
• Preferred examples of the polymerizable group are acryloyloxy (P-1), vinyloxy (P-2), oxiranyl (P-3) or maleimide (A).
• M 1 and M 2 are independently hydrogen, fluorine, methyl, or trifluoromethyl.
• MSG 1 is a monovalent organic group having at least one ring.
• Compounds (1S) to (1Y) correspond to compound (1).
• Compound (1) has an appropriate polymerization reactivity, a high conversion rate, and a high solubility in a liquid crystal composition as compared with a similar compound. Compound (1) has an appropriate balance regarding at least two of these physical properties. Therefore, the compound (1) can be added to the liquid crystal composition for the PSA mode.
• the polymerizable composition contains at least one of the compounds (1) as a first component.
• the component of this composition may be only the first component.
• the composition may contain other components such as a second component and a third component.
• the type of the second component depends on the intended use of the polymer.
• This polymerizable composition may further contain another polymerizable compound different from the compound (1) as the second component.
• Preferred examples of the other polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone.
• Further preferred examples are compounds having at least one acryloyloxy and compounds having at least one methacryloyloxy. Further preferred examples include compounds having both acryloyloxy and methacryloyloxy.
• R 25 , R 26 and R 27 are independently hydrogen or methyl; u, x and y are independently 0 or 1; v And w are independently integers from 1 to 10; L 21 , L 22 , L 23 , L 24 , L 25 , and L 26 are independently hydrogen or fluorine.
• an optical anisotropic body is formed by polymerization while controlling the alignment of liquid crystal molecules.
• This optical anisotropic body can be used for a retardation film, a polarizing element, a circularly polarizing element, an elliptically polarizing element, an antireflection film, a selective reflection film, a color compensation film, a viewing angle compensation film, and the like.
• An additive such as a polymerization initiator may be added to the polymerizable composition for the purpose of adjusting the physical properties of the optical anisotropic body.
• the polymerizable composition may contain a liquid crystal composition as the second component.
• the polymerizable composition contains the compound (1) as It is preferable to further include a compound selected from the components B, C and D shown in FIG.
• Component B is compounds (2) to (4).
• Component C is compounds (5) to (7).
• Component D is compound (8).
• a polymerizable composition with appropriately selected components has a high maximum temperature, a low minimum temperature, a small viscosity, a suitable optical anisotropy (ie, a large optical anisotropy or a small optical anisotropy), positively or negatively large It has a dielectric anisotropy and an appropriate elastic constant (ie, a large elastic constant or a small elastic constant).
• the polymerizable composition is prepared by adding the compound (1) to the liquid crystal composition. Additives may be added to the composition as necessary. In such a composition, the addition amount of the compound (1), that is, the component A is in the range of 0.01 wt% to 20 wt% based on the weight of the liquid crystal composition. A more preferable addition amount is in the range of 0.0133 wt% to 10 wt%. The most preferred addition amount is in the range of 0.05% to 5% by weight. At least one of other polymerizable compounds different from the compound (1) may be further added. In this case, the total amount of addition of the compound (1) and other polymerizable compounds is preferably within the above range.
• the physical properties of the polymer to be produced can be adjusted by appropriately selecting other polymerizable compounds. Examples of other polymerizable compounds are acrylates and methacrylates as described above. Examples thereof include compounds (M-1) to (M-12).
• Component B is a compound in which two terminal groups are alkyl or the like.
• Preferable examples of component B include compounds (2-1) to (2-11), compounds (3-1) to (3-19), or compounds (4-1) to (4-7). it can.
• R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, in which at least one —CH 2 — is —O - May be replaced with at least one hydrogen may be replaced with fluorine.
• Component B is a compound close to neutrality because the absolute value of dielectric anisotropy is small.
• the compound (2) is mainly effective in adjusting the viscosity or the optical anisotropy.
• Compounds (3) and (4) are effective in expanding the temperature range of the nematic phase by increasing the maximum temperature, or adjusting the optical anisotropy.
• the content of component B is preferably 30% by weight or more, more preferably 40%, based on the weight of the liquid crystal composition. % By weight or more.
• Component C is a compound having a halogen or fluorine-containing group at the right end.
• Preferable examples of component C include compounds (5-1) to (5-16), compounds (6-1) to (6-113), or compounds (7-1) to (7-57). it can.
• R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, at least one —CH 2 — may be replaced by —O—.
• At least one hydrogen may be replaced by fluorine;
• X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 , or -OCF is a 2 CHFCF 3.
• component C Since component C has a positive dielectric anisotropy and is very stable against heat, light, etc., a composition for a mode such as PS-IPS, PS-FFS, or PSA-OCB is prepared. Used in cases.
• the content of component C is suitably in the range of 1% to 99% by weight based on the weight of the liquid crystal composition, preferably in the range of 10% to 97% by weight, more preferably in the range of 40% to 95%. % Range.
• the content of component C is preferably 30% by weight or less based on the weight of the liquid crystal composition.
• Component D is a compound (8) in which the right terminal group is —C ⁇ N or —C ⁇ C—C ⁇ N.
• Preferable examples of component D include compounds (8-1) to (8-64).
• R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, at least one —CH 2 — may be replaced by —O—.
• At least one hydrogen may be replaced by fluorine;
• X 12 is —C ⁇ N or —C ⁇ C—C ⁇ N.
• component D Since component D has a positive dielectric anisotropy and a large value, it is mainly used when a composition for a mode such as PS-TN is prepared. By adding this component D, the dielectric anisotropy of the composition can be increased.
• Component D has the effect of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjusting the voltage-transmittance curve of the device.
• the content of component D is suitably in the range of 1 to 99% by weight, preferably 10% by weight based on the weight of the liquid crystal composition. % To 97% by weight, more preferably 40% to 95% by weight.
• the content of component D is preferably 30% by weight or less based on the weight of the liquid crystal composition.
• the polymerizable composition is prepared by a method of dissolving necessary components at a temperature higher than room temperature.
• additives may be added to the composition.
• additives include optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, antifoaming agents, polymerization initiators, polymerization inhibitors, and the like. Such additives are well known to those skilled in the art and are described in the literature.
• the optically active compound has an effect of preventing reverse twisting by inducing a helical structure in liquid crystal molecules to give a necessary twist angle.
• the helical pitch can be adjusted by adding an optically active compound.
• Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the helical pitch.
• Preferred examples of the optically active compound include the following compounds (Op-1) to (Op-18).
• ring J is 1,4-cyclohexylene or 1,4-phenylene
• R 28 is alkyl having 1 to 10 carbons.
• An antioxidant is effective for maintaining a large voltage holding ratio.
• Preferred examples of the antioxidant include the following compounds (AO-1) and (AO-2); IRGANOX 415, IRGANOX 565, IRGANOX 1010, IRGANOX 1035, IRGANOX 3114, and IRGANOX 1098 (trade name: BASF) be able to.
• the ultraviolet absorber is effective for preventing a decrease in the maximum temperature.
• Preferred examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like.
• AO-3 and (AO-4) the following compounds (AO-3) and (AO-4); TINUVIN 329, TINUVIN P, TINUVIN 326, TINUVIN 234, TINUVIN 213, TINUVIN 400, TINUVIN 328, and TINUVIN 99-2 (trade name: BASF Corporation) And 1,4-diazabicyclo [2.2.2] octane (DABCO).
• a light stabilizer such as an amine having steric hindrance is preferable for maintaining a large voltage holding ratio.
• Preferred examples of the light stabilizer include the following compounds (AO-5) and (AO-6); TINUVIN 144, TINUVIN 765, and TINUVIN 770DF (trade name: BASF).
• a thermal stabilizer is also effective for maintaining a large voltage holding ratio, and a preferred example is IRGAFOS 168 (trade name: BASF).
• Antifoaming agents are effective for preventing foaming.
• Preferred examples of the antifoaming agent include dimethyl silicone oil and methylphenyl silicone oil.
• R 29 is alkyl having 1 to 20 carbons, alkoxy having 1 to 20 carbons, —COOR 32 , or —CH 2 CH 2 COOR 32 , where R 32 is 1 carbon atom To 20 alkyls.
• R 30 is alkyl having 1 to 20 carbons.
• R 31 is hydrogen, methyl or O ⁇ (oxygen radical)
• ring K and ring L is 1,4-cyclohexylene or 1,4-phenylene
• x is 0, 1 or 2.
• Liquid crystal composite Compound (1) has suitable polymerization reactivity, high conversion rate, and high solubility in the liquid crystal composition.
• a liquid crystal composite is formed by polymerizing a polymerizable composition containing the compound (1) and the liquid crystal composition.
• Compound (1) forms a polymer in the liquid crystal composition by polymerization. This polymer has the effect of stabilizing the initial alignment of the liquid crystal molecules.
• a pretilt can be generated. Polymerization occurs by heat, light, and the like.
• a preferred reaction is photopolymerization. Polymerization may be carried out with an electric or magnetic field applied.
• the polymerization reactivity and conversion rate of the compound (1) can be adjusted.
• Compound (1) is suitable for radical polymerization.
• Compound (1) can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction temperature, the amount of the remaining compound (1) can be reduced.
• photoradical polymerization initiators are TPO, 1173 and 4265 from DASFURE series of BASF, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850, from Irgacure series. And 2959.
• photo radical polymerization initiators include 4-methoxyphenyl-2,4-bis (trichloromethyl) triazine, 2- (4-butoxystyryl) -5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzphenazine, benzophenone / Michler's ketone mixture, hexaarylbiimidazole / mercaptobenzimidazole mixture, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, benzyl Dimethyl ketal, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2,4-diethylxanthone / methyl p-dimethylaminobenzoate, benzophenone / methyltriethanolamine mixture It is.
• Polymerization can be carried out by irradiating ultraviolet rays after adding a radical photopolymerization initiator to the polymerizable composition.
• the unreacted polymerization initiator or the decomposition product of the polymerization initiator may cause display defects such as image burn-in on the device.
• photopolymerization may be performed without adding a polymerization initiator.
• a preferable wavelength of the irradiation light is in the range of 150 nm to 500 nm.
• a more preferable wavelength is in the range of 250 nm to 450 nm, and a most preferable wavelength is in the range of 300 nm to 400 nm.
• a polymerization inhibitor When storing the polymerizable compound, a polymerization inhibitor may be added to prevent polymerization.
• the polymerizable compound is usually added to the composition without removing the polymerization inhibitor.
• the polymerization inhibitor include hydroquinone derivatives such as hydroquinone and methylhydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine and the like.
• the effect of the polymer in a liquid crystal display element is interpreted as follows.
• the polymerizable composition is a mixture of a liquid crystal compound, a polymerizable compound and the like.
• this composition is injected into a liquid crystal cell, various initial orientations are exhibited depending on the characteristics of the cell and the composition used.
• the composition is irradiated with ultraviolet rays to polymerize the polymerizable compound.
• an electric field may be applied to the cell. This results in the formation of a polymer network in the polymerizable composition. Due to this network effect, the liquid crystal molecules are stabilized in a state before the ultraviolet irradiation.
• the initial alignment is a random alignment
• an ordered alignment such as a homogeneous alignment or a homeotropic alignment
• ultraviolet rays As described above, by polymerizing the polymerizable composition by ultraviolet irradiation, liquid crystal display elements stabilized in various alignment states can be obtained.
• Polymerization of the polymerizable composition is preferably performed in a display element.
• An example is as follows.
• a display element having two glass substrates provided with a transparent electrode on at least one of them is prepared.
• a polymerizable composition containing the compound (1), a liquid crystal composition, an additive and the like as components is prepared. This composition is injected into the display element.
• the display element is irradiated with ultraviolet rays to polymerize the compound (1).
• a liquid crystal composite is formed by this polymerization.
• a liquid crystal display element having a liquid crystal composite can be easily produced.
• the rubbing treatment of the alignment film may be omitted, and the alignment film may be omitted.
• a PSA mode liquid crystal display element When the addition amount of the polymerizable compound is in the range of 0.1% to 2% by weight based on the weight of the liquid crystal composition, a PSA mode liquid crystal display element is produced.
• a PSA mode element can be driven by a driving system such as AM (active matrix) or PM (passive matrix). Such an element can be applied to any of a reflection type, a transmission type, and a transflective type.
• a polymer-dispersed mode element By increasing the addition amount of the polymerizable compound, a polymer-dispersed mode element can also be produced.
• the present invention will be described in more detail with reference to examples. The invention is not limited by these examples.
• the present invention includes a mixture of the composition of Example 1 and the composition of Example 2.
• the invention also includes a mixture of at least two of the example compositions.
• the synthesized compound was identified by a method such as NMR analysis. The physical properties of the compound, composition and device were measured by the methods described below.
• Example NMR analysis of compound (1) For measurement, DRX-500 manufactured by Bruker BioSpin Corporation was used. In the 1 H-NMR measurement, the sample was dissolved in a deuterated solvent such as CDCl 3, and the measurement was performed at room temperature, 500 MHz, and 16 times of integration. Tetramethylsilane was used as an internal standard. For 19 F-NMR measurement, CFCl 3 was used as an internal standard and the number of integrations was 24.
• s is a singlet
• d is a doublet
• t is a triplet
• q is a quartet
• quint is a quintet
• sex a sextet
• m is a multiplet
• br is broad.
• LC-20AD Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used.
• the column used was YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle diameter 5 ⁇ m) manufactured by YMC.
• a detector a UV detector, an RI detector, a CORONA detector, or the like was appropriately used.
• the detection wavelength was 254 nm.
• a sample was dissolved in acetonitrile to prepare a 0.1 wt% solution, and 1 ⁇ L of this solution was introduced into the sample chamber.
• a recorder a C-R7Aplus manufactured by Shimadzu Corporation was used.
• UV-visible spectroscopic analysis PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used.
• the detection wavelength was 190 nm to 700 nm.
• the sample was dissolved in acetonitrile to prepare a 0.01 mmol / L solution, and the sample was placed in a quartz cell (optical path length 1 cm) and measured.
• Measurement Sample When measuring the phase structure and transition temperature (clearing point, melting point, polymerization initiation temperature, etc.), the compound itself was used as a sample. When measuring physical properties such as the maximum temperature, viscosity, optical anisotropy and dielectric anisotropy of the liquid crystalline compound, a mixture of this compound and mother liquid crystals was used as a sample. When measuring the physical properties of the liquid crystal composition, the composition itself was used as a sample.
• mother liquid crystals As the mother liquid crystals, the following mother liquid crystals (A) or mother liquid crystals (B) were used. The ratio of the components of the mother liquid crystals (A) and (B) is shown in wt%.
• Measurement method Physical properties were measured by the following methods. Many of these are the methods described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (JEITA) or a modified method thereof. there were. No thin film transistor (TFT) was attached to the TN device used for the measurement.
• Phase structure A sample was placed on a hot plate (METTLER FP-52 type hot stage) of a melting point measuring apparatus equipped with a polarizing microscope. While this sample was heated at a rate of 3 ° C./min, the phase state and its change were observed with a polarizing microscope to identify the type of phase.
• the crystal was represented as C. When the types of crystals can be distinguished, they are represented as C 1 and C 2 , respectively.
• the smectic phase is represented as S and the nematic phase is represented as N.
• the smectic phase when a smectic A phase, a smectic B phase, a smectic C phase, or a smectic F phase can be distinguished, they are represented as S A , S B , S C , or S F , respectively.
• the liquid (isotropic) was designated as I.
• the transition temperature is expressed as “C 50.0 N 100.0 I”, for example. This indicates that the transition temperature from the crystal to the nematic phase is 50.0 ° C., and the transition temperature from the nematic phase to the liquid is 100.0 ° C.
• Viscosity (bulk viscosity; ⁇ ; measured at 20 ° C .; mPa ⁇ s) The viscosity was measured using an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd.
• VHR-1 Voltage holding ratio
• the TN device used for the measurement had a polyimide alignment film, and the distance (cell gap) between the two glass substrates was 5 ⁇ m. This element was sealed with an adhesive that was cured with ultraviolet rays after the sample was placed. The device was charged by applying a pulse voltage (60 microseconds at 5 V). The decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined. Area B was the area when it was not attenuated. The voltage holding ratio was expressed as a percentage of area A with respect to area B.
• VHR-2 Voltage holding ratio (VHR-2; measured at 80 ° C .;%) The voltage holding ratio was measured by the above method except that the measurement was performed at 80 ° C. instead of 25 ° C. The results are indicated by the VHR-2 symbol.
• Viscosity (Rotational viscosity; ⁇ 1; measured at 25 ° C .; mPa ⁇ s) The measurement followed the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was put in a TN device in which the twist angle was 0 degree and the distance between two glass substrates (cell gap) was 5 ⁇ m. A voltage was applied to this device in steps of 0.5 V in the range of 16 V to 19.5 V. After no application for 0.2 seconds, the application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. The value of rotational viscosity was obtained from these measured values and M. Imai et al. The value of dielectric anisotropy necessary for this calculation was determined by the method described below using the element whose rotational viscosity was measured.
• Threshold voltage (Vth; measured at 25 ° C .; V)
• An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement.
• the light source was a halogen lamp.
• a sample was put in a normally white mode TN device in which the distance (cell gap) between two glass substrates was 0.45 / ⁇ n ( ⁇ m) and the twist angle was 80 degrees.
• the voltage (32 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 10V by 0.02V.
• the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured.
• a voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum and the transmittance was 0% when the light amount was the minimum.
• the threshold voltage was expressed as a voltage when the transmittance reached 90%.
• the rise time ( ⁇ r: rise time; millisecond) is the time required for the transmittance to change from 90% to 10%.
• the fall time ( ⁇ f: fall time; millisecond) is the time required to change the transmittance from 10% to 90%.
• the response time was expressed as the sum of the rise time and the fall time thus obtained.
• Example 12 1V2-BEB (F, F) -C (8-15) 7% 3-HB-C (8-1) 18% 2-BTB-1 (2-10) 10% 5-HH-VFF (2-1) 30% 3-HHB-1 (3-1) 5% VFF-HHB-1 (3-1) 6% VFF2-HHB-1 (3-1) 11% 3-H2BTB-2 (3-17) 5% 3-H2BTB-3 (3-17) 5% 3-H2BTB-4 (3-17) 3% Mi-H2H-Mi (No. 23) was added to the above composition in a proportion of 0.25% by weight.
• a liquid crystal display element having a mode such as PSA can be produced by polymerizing a polymerizable composition containing the polymerizable compound (1) and the liquid crystal composition.
• This device has a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime. Therefore, the compound (1) can be used for a liquid crystal projector, a liquid crystal television and the like.
• Compound (1) can also be used as a raw material for optical anisotropic bodies.

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