WO2024142928A1 - 液晶化合物、組成物、光学異方性層、積層体、積層体の製造方法 - Google Patents

液晶化合物、組成物、光学異方性層、積層体、積層体の製造方法 Download PDF

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WO2024142928A1
WO2024142928A1 PCT/JP2023/044581 JP2023044581W WO2024142928A1 WO 2024142928 A1 WO2024142928 A1 WO 2024142928A1 JP 2023044581 W JP2023044581 W JP 2023044581W WO 2024142928 A1 WO2024142928 A1 WO 2024142928A1
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liquid crystal
group
crystal compound
optically anisotropic
anisotropic layer
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PCT/JP2023/044581
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English (en)
French (fr)
Japanese (ja)
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啓介 中西
啓祐 小玉
峻也 加藤
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富士フイルム株式会社
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Publication of WO2024142928A1 publication Critical patent/WO2024142928A1/ja

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/18—Diffraction gratings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • a numerical range expressed using “to” means a range that includes the numerical values before and after “to” as the lower and upper limits.
  • the various components may be used singly or in combination of two or more substances corresponding to the various components.
  • the content of the component means the total content of the substances used in combination, unless otherwise specified.
  • (meth)acrylate means "either one or both of acrylate and methacrylate.”
  • the solid content means the components that form the optically anisotropic layer, and does not include solvent.
  • the birefringence is obtained by measuring Re( ⁇ ) and dividing the Re( ⁇ ) by the thickness.
  • Re( ⁇ ) and Rth( ⁇ ) respectively represent the in-plane retardation and the retardation in the thickness direction at a wavelength ⁇ .
  • the wavelength ⁇ is 550 nm.
  • Re( ⁇ ) and Rth( ⁇ ) are values measured at a wavelength ⁇ using an AxoScan (manufactured by Axometrics).
  • NAR-4T Abbe refractometer
  • DR-M2 multi-wavelength Abbe refractometer
  • values in the Polymer Handbook JOHN WILEY & SONS, INC.
  • catalogs of various optical films can be used.
  • Examples of average refractive index values of major optical films are as follows: cellulose acylate (1.48), cycloolefin polymer (1.52), polycarbonate (1.59), polymethyl methacrylate (1.49), and polystyrene (1.59).
  • the method of adjusting the birefringence of the optically anisotropic layer includes, for example, forming a coating film using a composition containing a liquid crystal compound, and then heating the coating film to change the state (e.g., isotropic state, etc.) of the liquid crystal compound, thereby reducing the birefringence of the optically anisotropic layer.
  • the present inventors have found that when a conventional liquid crystal compound is used in the above method, the birefringence of the obtained optically anisotropic layer is rapidly reduced when the birefringence is adjusted by heating, making it difficult to adjust the birefringence (e.g., the birefringence becomes 0, etc.).
  • the specific liquid crystal compound has a relatively long mesogen structure having four or more aromatic ring groups or non-aromatic ring groups (hereinafter also referred to as "ring groups") represented by A 1 to A 3 in a linear arrangement, so that the phase transition temperature of the liquid crystal phase to the isotropic phase (Iso) is likely to be high.
  • ring groups aromatic ring groups or non-aromatic ring groups
  • each of the predetermined groups represented by any of L 1 to L 5 is a single bond or has 1 to 20 carbon atoms.
  • the effect of the present invention is said to be superior when it has at least one of the effects of being able to adjust the birefringence more widely and having excellent in-plane uniformity.
  • G represents 0 when b represents 0, represents the numerical value of g when b represents 1, and represents the total numerical value of multiple g's when b represents an integer of 2 to 8.
  • a represents an integer of 2 to 8
  • the plurality of Z 1s and the plurality of A 1 -(L 3 -P 3 ) e may be the same or different from each other.
  • e represents an integer of 2 or 3
  • the plurality of L 3s and the plurality of P 3s may be the same or different from each other.
  • b represents an integer of 2 to 8
  • the plurality of Z 4s and the plurality of A 3 -(L 5 -P 5 ) gs may be the same or different from each other.
  • P 1 to P 5 each independently represent a polymerizable group represented by any one of formulas (Ia) to (Ij).
  • the liquid crystal compound represented by formula (I) has, at least one represents a polymerizable group represented by any one of formulas (Ia) to (Ic) (hereinafter also referred to as "polymerizable group E"), and at least one represents a polymerizable group represented by any one of formulas (Id) to (Ij) (hereinafter also referred to as "polymerizable group R").
  • At least one hydrogen atom bonded to the carbon atom may be substituted with a fluorine atom or a chlorine atom, or all hydrogen atoms bonded to the carbon atom may be substituted with a fluorine atom or a chlorine atom.
  • L 1 to L 5 each represent an alkyl group having 1 to 20 carbon atoms in which at least one -CH 2 - is substituted with -O-, -S-, -NR X1 - or -CO-
  • the total number of -O-, -S-, -NR X1 - and -CO- introduced in place of -CH 2 - in the alkyl group is preferably 1 to 4, and more preferably 1 or 2.
  • L 1 to L 5 represent an alkylene group having 1 to 20 carbon atoms in which at least one -CH 2 - is substituted with -O-, -S-, -NR X1 - or -CO-
  • the position of introduction of -O-, -S-, -NR X1 - or -CO- introduced in place of -CH 2 - in the alkylene group may be either a position adjacent to the polymerizable group represented by P 1 to P 5 or a position adjacent to a bonding position different from the polymerizable group side represented by P 1 to P 5 , or may be any other position.
  • the alkyl group having 1 to 15 carbon atoms represented by R X1 As the alkyl group having 1 to 15 carbon atoms represented by R X1 , the above-mentioned alkyl group having 1 to 15 carbon atoms represented by R I1 is preferable.
  • the upper limit of the number of carbon atoms in the alkylene group having 1 to 20 carbon atoms in L3 to L5 is preferably 12 or less, more preferably 10 or less, even more preferably 8 or less, particularly preferably 5 or less, and most preferably 4 or less, in terms of better effects of the present invention and higher phase transition temperature (Iso) of the specific liquid crystal compound from liquid crystal phase to isotropic phase.
  • the lower limit is preferably 1 or more.
  • the number of carbon atoms in the alkylene group having 1 to 20 carbon atoms in L3 and L5 is preferably 1 to 5, and more preferably 1 to 4, in terms of obtaining better effects of the present invention, increasing the liquid crystal phase-isotropic phase transition temperature (Iso) of the specific liquid crystal compound, and decreasing the melting point of the specific liquid crystal compound.
  • L 1 to L 5 examples include, for example, —O—CH 2 —, —O—CH 2 CH 2 —, —O—CH 2 CH 2 CH 2 —, —O—CH 2 CH 2 CH 2 CH 2 —, —O—CH 2 CH 2 OCH 2 —, —O—CH 2 CH 2 CH 2 CH 2 CH 2 —, —O—CH 2 CH 2 CH 2 OCH 2 —, —O—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —O—CH 2 CH 2 CH 2 CH 2 OCH 2 —, —COO—CH 2 —, —COO—CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—CH 2 CH 2 CH 2 —, —COO—
  • a 1 to A 3 each independently represent an aromatic ring group which may have a substituent or a non-aromatic ring group which may have a substituent.
  • the aromatic ring group or the non-aromatic ring group represented by A 1 is an aromatic ring group having a valence of (2+e) which may have a substituent, or a non-aromatic ring group having a valence of (2+e) which may have a substituent
  • the aromatic ring group or the non-aromatic ring group represented by A 2 is an aromatic ring group having a valence of (2+f) which may have a substituent, or a non-aromatic ring group having a valence of (2+f) which may have a substituent
  • the aromatic ring group or the non-aromatic ring group represented by A 3 is an aromatic ring group having a valence of (2+g) which may have a substituent, or a non-aromatic ring group having a valence of
  • the aromatic ring group or the non-aromatic ring group represented by A 1 is, for example, a group formed by removing (2+e) hydrogen atoms from the aromatic ring constituting the aromatic ring group, or the non-aromatic ring constituting the non-aromatic ring group.
  • the aromatic ring constituting the aromatic ring group and the non-aromatic ring constituting the non-aromatic ring group are preferably 5- to 7-membered rings, more preferably 5- or 6-membered rings, and even more preferably 6-membered rings.
  • the aromatic rings and non-aromatic rings may be either monocyclic or polycyclic, and are preferably monocyclic.
  • the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, and is preferably an aromatic hydrocarbon ring in that the specific liquid crystal compound has better liquid crystal properties. Examples of the aromatic hydrocarbon ring include a benzene ring and a naphthalene ring, with the benzene ring being preferred.
  • the heteroatom contained in the aromatic heterocycle is not particularly limited, and may be, for example, a nitrogen atom.
  • the number of heteroatoms contained in the aromatic heterocycle is not particularly limited, and is preferably 1 to 4, and more preferably 1 or 2.
  • Examples of the aromatic heterocycle include a pyridine ring and a pyrimidine ring.
  • the non-aromatic ring may be either an aliphatic hydrocarbon ring or an aliphatic heterocycle, with an aliphatic hydrocarbon ring being preferred in that the specific liquid crystal compound has better liquid crystallinity.
  • An example of the aliphatic hydrocarbon ring is a cyclohexane ring.
  • the heteroatom contained in the aliphatic heterocycle is not particularly limited, and may be, for example, a nitrogen atom.
  • the number of heteroatoms contained in the aromatic heterocycle is not particularly limited, and is, for example, preferably 1 to 4, and more preferably 1 or 2.
  • An example of the aliphatic heterocycle is a piperazine ring.
  • a phenylene group which may have a substituent or a cyclohexylene group which may have a substituent is preferable, and a 1,4-phenylene group which may have a substituent or a trans-1,4-cyclohexylene group which may have a substituent is more preferable.
  • the bonding positions of Z 1 and Z 2 on the cyclohexane ring are preferably trans-1,4 positions (trans-para positions).
  • the bonding positions of Z 2 and Z 3 on the cyclohexane ring are preferably trans-1,4 positions (trans-para positions).
  • the bonding positions of Z 3 and Z 4 on the cyclohexane ring are preferably trans-1,4 positions (trans-para positions).
  • the substituents which the aromatic ring group and the non-aromatic ring group may have refer to substituents other than -L 3 -P 3 , -L 4 -P 4 and -L 5 -P 5 in formula (I).
  • the substituent include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms which may be substituted with a halogen atom, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an acyloxy group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 6 carbon atoms, and an acylamino group having 2 to 6 carbon atoms.
  • Z 1 to Z 4 represent -COO-, and it is more preferable that Z 1 and Z 4 represent a single bond, and Z 2 and Z 3 represent -COO- (preferably, the carbonyl group is located on the bonding position side with A 2 ).
  • a and b each independently represent an integer of 0 to 8, and 3 ⁇ a+b ⁇ 8.
  • e to g each independently represent an integer of 0 to 3.
  • a and b each independently represent preferably an integer of 1 to 8, more preferably an integer of 1 to 6, even more preferably an integer of 1 to 5, particularly preferably an integer of 1 to 4, and most preferably an integer of 2 to 4.
  • Each of e to g is preferably an integer of 0 to 2, and more preferably 0 or 1.
  • f is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0.
  • 3 ⁇ c+d+E+f+G means that the total value of c, d, E, f, and G is 3 or more.
  • c represents 0 when X 1 is a hydrogen atom, and represents 1 when X 1 represents a group represented by *-L 1 -P 1.
  • d represents 0 when X 2 is a hydrogen atom, and represents 1 when X 2 represents a group represented by *-L 2 -P 2.
  • E represents 0 when a represents 0, represents the numerical value of e when a represents 1, and represents the total numerical value of multiple e's when a represents an integer of 2 to 8.
  • G represents 0 when b represents 0, represents the numerical value of g when b represents 1, and represents the total numerical value of multiple g's when b represents an integer of 2 to 8.
  • E and G will be described with an example.
  • E corresponds to one value of e specified in formula (IX).
  • E corresponds to the total value of three values of e specified in formula (IY).
  • the definition of G has the same meaning as the definition of E.
  • the upper limit of c+d+E+f+G is preferably 14 or less, more preferably 10 or less, still more preferably 8 or less, and particularly preferably 6 or less.
  • the lower limit is 3 or more, and preferably 4 or more.
  • E and G each independently represent preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and further preferably 1 or 2, in that the effects of the present invention are more excellent.
  • e in the group represented by (L 3 -P 3 ) e substituting A 1 closest to Z 2 is preferably an integer of 1 to 3, and more preferably 1 or 2.
  • e in the group represented by (L 3 -P 3 ) e substituting another A 1 may be an integer of 0 to 3, and is preferably 0 to 2, and more preferably 0 or 1.
  • g in the group represented by (L 5 -P 5 ) g substituting the A 3 closest to Z 3 among the multiple A 3s is preferably an integer of 1 to 3, and more preferably 1 or 2.
  • g in the group represented by (L 5 -P 5 ) g substituting another A 3 may be an integer of 0 to 3, and is preferably 0 to 2, and more preferably 0 or 1.
  • the specific liquid crystal compound is preferably a compound represented by formula (II) in that it provides a more excellent effect of the present invention.
  • a1 and b1 each independently represent 0 or 1, and 1 ⁇ a1+b1 ⁇ 2.
  • e1 and g1 each independently represent an integer of 1 to 3.
  • e2 and g2 each independently represent an integer of 0 to 2.
  • e1+e2 represents an integer of 0 to 3
  • e1 and g1 each independently preferably represent 1 or 2, and more preferably represent 1.
  • Each of e2 and g2 independently is preferably 0 or 1.
  • e1+e2 and g1+g2 are preferably 1 or 2, and more preferably 1.
  • a1 a plurality of Z 1's may be the same or different from each other, and a plurality of A 1's may be the same or different from each other.
  • e1 represents 2 or 3, or when e2 represents 1 or 2, a plurality of L 3 's and a plurality of P 3 's may be the same or different from each other.
  • b1 a plurality of Z 4's may be the same or different from each other, and a plurality of A 3's may be the same or different from each other.
  • g1 represents 2 or 3, or when g2 represents 1 or 2
  • a plurality of L 5s and a plurality of P 5s may be the same or different from each other.
  • the lower limit of the molecular weight of the specific liquid crystal compound is preferably 600 or more, more preferably 800 or more, and even more preferably 900 or more.
  • the upper limit is preferably 2000 or less, more preferably 1500 or less, and even more preferably 1200 or less.
  • composition contains the specific liquid crystal compound described above.
  • the content of the specific liquid crystal compound in the composition is preferably from 60 to 100% by mass, more preferably from 70 to 95% by mass, and even more preferably from 80 to 90% by mass, based on the mass of the total solid content of the composition.
  • the curing agent examples include the phenol-based curing agents, amide-based curing agents, and active ester-based curing agents described in paragraphs [0095] to [0098] of JP 2022-125980 A, as well as amine-based curing agents, carboxylic acid-based curing agents, acid anhydride-based curing agents, polymercaptan-based curing agents, isocyanate-based curing agents, blocked isocyanate-based curing agents, and carbodiimide compounds.
  • the lower limit of the reactive group content in the curing agent (the amount of reactive group per gram of curing agent) is not particularly limited, but in terms of the superior effect of the present invention, it is preferably 10 mmol/g or more, more preferably 15 mmol/g or more, and even more preferably 20 mmol/g or more.
  • the upper limit is preferably 50 mmol/g or less, and more preferably 40 mmol/g or less.
  • the lower limit of the hydroxyl value of the phenolic compound is preferably 20 g/mol or more, and more preferably 25 g/mol or more.
  • the upper limit is preferably 100 g/mol or less, more preferably 67 g/mol or less, and even more preferably 50 g/mol or less, in order to provide sufficient curability without disturbing the liquid crystallinity.
  • ma represents an integer of 0 or more.
  • ma is preferably an integer of 0 to 10, more preferably an integer of 0 to 3, still more preferably 0 or 1, and particularly preferably 1.
  • the plurality of R2s when there are a plurality of R2s , the plurality of R2s may be the same or different.
  • the plurality of R3s may be the same or different.
  • the plurality of Lx2s when there are a plurality of Lx2s , the plurality of Lx2s may be the same or different.
  • the plurality of nb's when there are a plurality of nb's, the plurality of nb's may be the same or different.
  • R 1 and R 4 each independently represent a hydrogen atom or a substituent.
  • substituents represented by R1 and R4 include a halogen atom, a carboxylic acid group, an amino group, an alkyl group, an alkoxy group, and an alkoxycarbonyl group.
  • the alkyl group may be either linear or branched.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 3, and particularly preferably 1.
  • the alkyl group may further have a substituent.
  • the alkyl group moiety in the alkoxy group and the alkyl group moiety in the alkoxycarbonyl group are the same as the above alkyl group.
  • R 1 and R 4 are preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a chlorine atom, and even more preferably a hydrogen atom.
  • R2 represents a hydrogen atom or a hydroxyl group.
  • R 2's When a plurality of R 2's are present, it is preferable that at least one of the plurality of R 2 's represents a hydroxyl group, and it is more preferable that all of R 2 's represent a hydroxyl group.
  • L x1 is preferably —C(R 5 )(R 6 )— or —CO—.
  • L x2 is preferably —C(R 7 )(R 8 )—.
  • R 5 to R 8 each independently represent a hydrogen atom or a substituent.
  • the above-mentioned substituent is preferably a hydroxyl group, a halogen atom, a carboxylic acid group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group, and more preferably a hydroxyl group, a halogen atom, a carboxylic acid group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group.
  • the alkyl group may be either linear or branched.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 3, and particularly preferably 1.
  • the alkyl group may have a substituent.
  • substituents examples include a halogen atom (e.g., a fluorine atom, etc.).
  • the alkyl group moiety in the alkoxy group and the alkyl group moiety in the alkoxycarbonyl group are the same as the above alkyl group.
  • R 5 to R 8 are preferably a hydrogen atom or a hydroxyl group, and more preferably a hydrogen atom.
  • L x2 is preferably —CH 2 —, —CH(OH)— or —CO—, and more preferably —CH 2 —.
  • L x1 is preferably —CH 2 —, —CH(OH)— or —CO—.
  • L x1 and L x2 are preferably —CH 2 —.
  • Examples of compounds represented by formula (P1) include the compounds shown below.
  • the composition may further comprise a solvent.
  • the type of the solvent is not particularly limited, and an organic solvent is preferable, for example, cyclopentanone, cyclohexanone, ethyl acetate, methyl ethyl ketone, dichloromethane, and tetrahydrofuran.
  • the content of the solvent is preferably an amount that makes the solids concentration of the composition 1 to 90 mass %, and more preferably an amount that makes the solids concentration of the composition 2 to 85 mass %.
  • the optical axis 30A is aligned along the long axis direction of the rod shape.
  • the "direction indicated by the arrow X” will also be simply referred to as the "arrow X direction.”
  • the optical axis 30A originating from the liquid crystal compound 30 will also be referred to as the "optical axis 30A of the liquid crystal compound 30" or the "optical axis 30A.”
  • the liquid crystal compound 30 is two-dimensionally aligned in a plane parallel to the direction of the arrow X and the direction of the arrow Y perpendicular to the direction of the arrow X. In Fig. 1, the Y direction is perpendicular to the paper surface.
  • the distance between the centers in the direction of the arrow X of two liquid crystal compounds 30 whose directions of the arrow X and the optical axis 30A coincide with each other is defined as the length ⁇ of one period.
  • this length ⁇ of one period is also referred to as "one period ⁇ ".
  • the liquid crystal alignment pattern of the optically anisotropic layer 10 repeats this one period ⁇ in the direction of the arrow X, that is, in one direction in which the direction of the optical axis 30A changes by continuously rotating.
  • the optically anisotropic layer 10 has a liquid crystal alignment pattern in which the direction of the optical axis is rotated in at least one direction in the plane thereof, and the optically anisotropic layer 10 may have a portion in which the direction of the optical axis is constant.
  • liquid crystal compound LCa The liquid crystal compound LCa was synthesized with reference to WO 2008/105538.
  • Example 1 [Preparation of Laminate 1-1] A solution of polyimide SE-130 (manufactured by Nissan Chemical Industries, Ltd.) for alignment film was applied by spin coating onto a glass substrate of 100 ⁇ 100 mm and 0.7 mm thickness, dried at 100° C. for 10 minutes, and then baked at 200° C. for 60 minutes to obtain a coating film. The obtained coating film was subjected to a rubbing treatment to obtain a support with an alignment film. The rubbing treatment was performed using a commercially available rubbing device.
  • polyimide SE-130 manufactured by Nissan Chemical Industries, Ltd.
  • Laminate 1-2 The composition LC-1 was applied to the obtained alignment film using a spin coater at 1000 rpm for 10 seconds in the same manner as in the laminate 1-1. The coating of the composition LC-1 was then heated to 90°C on a hot plate. Thereafter, a thermal curing treatment was performed for 3 minutes in the temperature range shown in the table below. The film was exposed to light with a wavelength of 365 nm at an exposure dose of 1200 mJ/ cm2 using a high-pressure mercury lamp under a nitrogen atmosphere to form an optically anisotropic layer B1. In this manner, a laminate 1-2 was prepared, which was provided with a support, an alignment film, and an optically anisotropic layer B1 in this order.
  • ⁇ In-plane uniformity> The alignment of the optically anisotropic layer in each laminate was observed using a polarizing microscope to determine the alignment caused by the liquid crystal compound.
  • the in-plane uniformity was evaluated according to the following criteria. "A”: The liquid crystal compound was uniformly aligned over the entire surface. "B”: The orientation of the liquid crystal compound was locally uniform within the plane. “C”: The liquid crystal compound was not uniformly aligned in the plane.
  • a photo-alignment film was prepared with reference to WO 2021/182625. Specifically, a glass substrate was prepared as a support. The following coating solution for forming a photo-alignment film was applied onto the support at 2500 rpm for 30 seconds using a spin coater. The support on which the coating film of the coating solution for forming a photo-alignment film was formed was dried on a hot plate at 60° C. for 60 seconds to form a coating film on the support.
  • Laminate 3-1 was prepared in the same manner as laminate 1-1 in Example 1 above, except that the support with the alignment film was changed to a support with a photo-alignment film P-1.
  • Laminate 3-2 was prepared in the same manner as laminate 1-2 in Example 1 above, except that the support with the alignment film was changed to a support with a photo-alignment film P-1.
  • the laminate 3-1 includes a support, a photo-alignment film P-1, and an optically anisotropic layer A3, in this order.
  • the laminate 3-2 includes a support, a photo-alignment film P-1, and an optically anisotropic layer B3, in this order.

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PCT/JP2023/044581 2022-12-28 2023-12-13 液晶化合物、組成物、光学異方性層、積層体、積層体の製造方法 WO2024142928A1 (ja)

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