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WO2025143020A1 - Composition de cristaux liquides, film anisotrope absorbant la lumière, stratifié et dispositif d'affichage d'image - Google Patents

Composition de cristaux liquides, film anisotrope absorbant la lumière, stratifié et dispositif d'affichage d'image Download PDF

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Publication number
WO2025143020A1
WO2025143020A1 PCT/JP2024/045890 JP2024045890W WO2025143020A1 WO 2025143020 A1 WO2025143020 A1 WO 2025143020A1 JP 2024045890 W JP2024045890 W JP 2024045890W WO 2025143020 A1 WO2025143020 A1 WO 2025143020A1
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liquid crystal
polymer
mass
repeating unit
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Japanese (ja)
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渉 星野
拓史 松山
寛之 大草
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Fujifilm Corp
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Fujifilm Corp
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • Patent Document 1 shows an optically anisotropic layer obtained by using a liquid crystal composition containing a liquid crystal compound, a dichroic substance, and an interface improver having a repeating unit containing a fluorine atom, and discloses that by using the interface improver having a repeating unit containing a fluorine atom, an optically anisotropic layer in which orientation defects and the like are suppressed can be obtained.
  • the present inventors formed an optically absorptive anisotropic film using a polymer (interfacial modifier) having a repeating unit containing a silicon atom in place of the interfacial modifier containing a fluorine atom in a liquid crystal composition containing a liquid crystal compound, a dichroic substance, and a fluorine atom-containing interfacial modifier as described in Patent Document 1, and found that surface unevenness may occur or the degree of orientation may be insufficient.
  • a polymer interfacial modifier
  • the present invention aims to provide a liquid crystal composition, an optically absorptive anisotropic film, a laminate, and an image display device that can form an optically absorptive anisotropic film that suppresses the occurrence of surface unevenness and has an excellent degree of orientation.
  • a liquid crystal compound comprising a repeating unit A having a structure represented by formula (A) described below;
  • a liquid crystal composition comprising a repeating unit A having a structure represented by formula (A) described below and a polymer 2 different from the polymer 1,
  • a liquid crystal composition wherein the content of silicon atoms contained in the polymer 1 is X1 parts by mass and the content of silicon atoms contained in the polymer 2 is X2 parts by mass relative to 100 parts by mass of a total solid content of the liquid crystal composition, and a ratio represented by X1/X2 is 1 or more.
  • R A1 and R A2 each independently represent a hydrogen atom or an alkyl group.
  • R A3 represents a hydrogen atom, a halogen atom, or a substituent.
  • X represents a substituent containing one or more structures represented by formula (a) described below.
  • * indicates the bond position.
  • R a1 , R a2 and R a3 each independently represent an alkyl group, an alkenyl group, an aryl group or an alkylenearyl group, each of which may have a substituent.
  • the content of the repeating unit A contained in the polymer 1 relative to all repeating units contained in the polymer 1 is A1% by mass
  • A1 is 30.0 to 75.0% by mass
  • A1 is 30.0 to 90.0% by mass, The liquid crystal composition according to [2] or [3], wherein A2 is 5.0 to 65.0% by mass.
  • A2 is 5.0 to 65.0% by mass.
  • X1 is 0.0016 to 0.057 parts by mass, The liquid crystal composition according to any one of [1] to [7], wherein X2 is 0.0013 to 0.0500 parts by mass.
  • R B4 and R B5 When R B4 and R B5 are substituents, R B4 and R B5 may be linked to form a ring.
  • the liquid crystal composition according to any one of [1] to [10], wherein at least one of the polymer 1 and the polymer 2 has a repeating unit D represented by formula (D) described below.
  • R D1 , R D2 and R D3 each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, or an aryl group.
  • L D1 represents a single bond, —COO— or —CO—.
  • SpD1 represents a divalent hydrocarbon group having 1 to 20 carbon atoms, provided that, among the -CH2- groups constituting a part of the hydrocarbon group, one or two or more non-adjacent -CH2- groups may each independently be substituted with -O-, -S-, -NH- or -N(Q)-, and Q represents a substituent.
  • L D2 and L D3 each independently represent a single bond or a divalent linking group.
  • CyD represents a divalent linking group containing a mesogenic group.
  • D represents a hydrogen-bonding group composed of a hydrogen atom and a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may have a substituent.
  • n represents an integer of 1 to 3.
  • a plurality of L D2 may be the same or different, and a plurality of Cy D may be the same or different.
  • R B1 , R B2 and R B3 each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group or an aryl group.
  • R B4 and R B5 each independently represent a hydrogen atom or a substituent.
  • SpD1 represents a divalent hydrocarbon group having 1 to 20 carbon atoms, provided that, among the -CH2- groups constituting a part of the hydrocarbon group, one or two or more non-adjacent -CH2- groups may each independently be substituted with -O-, -S-, -NH- or -N(Q)-, and Q represents a substituent.
  • L D2 and L D3 each independently represent a single bond or a divalent linking group.
  • CyD represents a divalent linking group containing a mesogenic group.
  • D represents a hydrogen-bonding group composed of a hydrogen atom and a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may have a substituent.
  • n represents an integer of 1 to 3.
  • At least one of the polymer 1 and the polymer 2 has a repeating unit E that does not contain a fluorine atom and a polymerizable group,
  • the liquid crystal composition according to any one of [1] to [9], wherein the repeating unit E satisfies the following condition 1 or the following condition 2:
  • Condition 1 The repeating unit E has a polar group at the end of the side chain.
  • Condition 2 The repeating unit E is represented by the formula (E1) or (E2) described below.
  • R E2 represents a hydrogen atom or a substituent.
  • L E1 represents a single bond or a divalent linking group selected from the group consisting of -O-, -S-, -COO-, -OCO-, -CONR L1 -, -NR L1 COO-, -CR L1 N-, a substituted or unsubstituted divalent aliphatic group, a substituted or unsubstituted divalent aromatic group, and combinations thereof, and R L1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • Ring E represents a ring structure having a cationized nitrogen atom.
  • X represents an anion.
  • L2 represents a hydrogen atom or a substituent.
  • R E3 represents a hydrogen atom or a substituent.
  • L E3 represents a single bond or a divalent linking group selected from the group consisting of -O-, -S-, -COO-, -OCO-, -CONR L1 -, -NR L1 COO-, -CR L1 N-, a substituted or unsubstituted divalent aliphatic group, a substituted or unsubstituted divalent aromatic group, and combinations thereof
  • R L1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the present invention provides a liquid crystal composition, an optically absorptive anisotropic film, a laminate, and an image display device that can form an optically absorptive anisotropic film that suppresses the occurrence of surface unevenness and has an excellent degree of orientation.
  • FIG. 1 is a side view that illustrates an embodiment of a virtual reality display device that is an example of an image display device of the present invention.
  • a numerical range expressed using "to” means a range including the numerical values described before and after "to” as the lower and upper limits.
  • the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of another numerical range described in stages.
  • the upper limit or lower limit described in a certain numerical range may be replaced with a value shown in the examples.
  • each component may be used alone or in combination of two or more substances corresponding to each component.
  • the content of the component refers to the total content of the substances used in combination, unless otherwise specified.
  • “(meth)acrylate” is a notation representing “acrylate” or “methacrylate”
  • “(meth)acrylic” is a notation representing "acrylic” or “methacrylic”
  • “(meth)acryloyl” is a notation representing "acryloyl” or “methacryloyl”
  • “(meth)acrylic acid” is a notation representing "acrylic acid” or "methacrylic acid”.
  • the bonding direction of the divalent group described in this specification is not limited unless otherwise specified.
  • Y when Y is -C(O)-O- in a compound represented by the formula "X-Y-Z", Y may be -C(O)-O- or -O-C(O)-.
  • the above compound may be "X-C(O)-O-Z" or "X-O-C(O)-Z".
  • perpendicular and parallel with respect to angles mean a range of the exact angle ⁇ 10°, and “same” and “different” with respect to angles can be determined based on whether the difference is less than 5°.
  • visible light refers to 380 to 780 nm. In this specification, unless otherwise specified, the measurement wavelength is 550 nm.
  • slow axis refers to the direction in the plane in which the refractive index is maximum. Note that when referring to the slow axis of an optically absorptive anisotropic film, the slow axis of the entire optically absorptive anisotropic film is intended.
  • Re( ⁇ ) and “Rth( ⁇ )” respectively represent the in-plane retardation and the retardation in the thickness direction at a wavelength ⁇ .
  • the substituent W represents the following group: Examples of the substituent W include a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an alkylcarbonyl group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 1 to 10 carbon atoms, an alkylcarbonyloxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylaminocarbonyl group, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (which may also be called a heterocyclic group), a cyano group, a halogen atom, an alkyl group having
  • LW represents a single bond or a divalent linking group
  • SPW represents a divalent spacer group
  • Q represents a terminal group
  • * represents the bonding position.
  • Examples of the divalent linking group represented by LW include, -O-, -Si(CH 3 ) 2 -, -(Si(CH 3 ) 2 O) g - (g represents an integer of 1 to 10), -N(Z)-, -C(Z) ⁇ C(Z 1 )-, -C(Z) ⁇ N-, -C(O)-, -C(O)O-, -O-C(O)O-, -C(O)N(Z)-, -C(Z) ⁇ C(Z 1 )-C(O)O-, -C(Z) ⁇ N-, -C(Z) ⁇ C(Z 1 )-C(O)N(Z 2 )-, -C(Z) ⁇ C(Z 1 )-C(O)-S-, -C(Z) ⁇ N-N ⁇ C(Z 1 )-(Z, Z 1 and Z
  • Each of 2 independently represents hydrogen, an alkyl group having 1 to 4 carbon
  • LW may be a group combining two or more of these groups (hereinafter also abbreviated as "L-C").
  • the divalent spacer group represented by SPW includes a linear, branched or cyclic alkylene group having 1 to 50 carbon atoms, or a heterocyclic group having 1 to 20 carbon atoms.
  • the hydrogen atoms of the alkylene groups and the hydrogen atoms of the heterocyclic groups are preferably halogen atoms, cyano groups, -ZH1 , -OH, -OZH1 , -COOH, -C(O) ZH1 , -C(O) OZH1 , -OC(O) ZH1 , -OC(O) OZH1 , -NZH1ZH2, -NZH1C (O) ZH2 , -NZH1C (O) OZH2 , -C(O) NZH1ZH2 , -OC (O) NZH1ZH2 , -NZH1C (O) NZH2OZH3 , -SH , -SZH1 , -C(S ) ZH1 , -C(O) SZH1 , -SC(O ) Z H1 , where Z H1 , Z
  • L represents a single bond or a divalent linking group.
  • divalent linking group are the same as those of LW and SPW described above.
  • CL represents a crosslinkable group.
  • Specific examples of the crosslinkable group include the crosslinkable groups represented by the following formulae (P-1) to (P-30).
  • R P represents a hydrogen atom, a halogen atom, a linear, branched, or cyclic alkylene group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (which may also be called a heterocyclic group), a cyano group, a hydroxy group, a nitro group, a carboxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonio group
  • a preferred embodiment of the crosslinkable group is a radically polymerizable group or a cationic polymerizable group.
  • Examples of the terminal group represented by Q include a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (which may also be called a heterocyclic group), a cyano group, a hydroxy group, a nitro group, a carboxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonio group, an acylamino group, an aminocarbonylamino group, an alkoxy group, an
  • Each of these groups represents an aryloxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group,
  • the liquid crystal composition of the present invention includes a liquid crystal compound, a dichroic substance, a polymer 1 having a repeating unit A including a structure represented by formula (A) described below, and a polymer 2 having a repeating unit A including a structure represented by formula (A) described below and different from the polymer 1.
  • the ratio represented by X1/X2 is 1 or more.
  • the liquid crystal composition contains polymer 1 and polymer 2
  • aggregation of the polymers is suppressed compared to the case of using a liquid crystal composition containing only one type of polymer having a repeating unit A including a structure represented by formula (A), and as a result, aggregation of liquid crystal compounds and dichroic substances that may cause alignment defects is also suppressed, and it is presumed that the degree of alignment of the obtained optically absorptive anisotropic film is improved.
  • the liquid crystal composition of the present invention may contain two or more types of polymers having a repeating unit A including a structure represented by the following formula (A), and may contain three or more types of polymers having a repeating unit A including a structure represented by the following formula (A). In the case where three or more types of polymers having a repeating unit A including a structure represented by the following formula (A) are included, at least two of the three or more types of polymers may satisfy the relationship between polymer 1 and polymer 2 described below (specifically, the value of X1/X2, etc.).
  • the polymer having a repeating unit A including a structure represented by the following formula (A) contained in the liquid crystal composition of the present invention preferably does not contain a fluorine atom.
  • the content of the liquid crystal compound is preferably 25 to 2000 parts by mass, more preferably 100 to 1300 parts by mass, and even more preferably 200 to 900 parts by mass, per 100 parts by mass of the dichroic material. By having the content of the liquid crystal compound within the above range, the degree of orientation of the dichroic material is further improved.
  • the dichroic substance is not particularly limited, and examples thereof include visible light absorbing substances (dichroic dyes), luminescent substances (fluorescent substances, phosphorescent substances), ultraviolet absorbing substances, infrared absorbing substances, nonlinear optical substances, carbon nanotubes, and inorganic substances (e.g., quantum rods). Conventionally known dichroic substances (dichroic dyes) can be used.
  • a dichroic azo dye compound As the dichroic substance, a dichroic azo dye compound is preferable.
  • the dichroic azo dye compound means an azo dye compound whose absorbance varies depending on the direction.
  • the dichroic azo dye compound may or may not exhibit liquid crystallinity. When the dichroic azo dye compound exhibits liquid crystallinity, it may exhibit either nematic or smectic properties.
  • the temperature range in which the liquid crystal phase is exhibited is preferably room temperature (about 20 to 28°C) to 300°C, and more preferably 50 to 200°C from the viewpoints of handling and manufacturing suitability.
  • nx is a number of 1 or more, preferably a number from 1 to 100, and more preferably a number from 1 to 11.
  • nx is a number of 2 or more, multiple [O-Si(R X11 ) 2 ] may be the same or different.
  • substituent X is a group represented by the following formula (X1). *-L X10 -C(R X20 ) mx (L X11 -a) 3-mx formula (X1)
  • L X10 and L X11 each independently represent a divalent hydrocarbon group.
  • one or more -CH 2 - may each independently be substituted with a divalent group such as -O-, -CO-, -C(O)-O-, -C(O)-N(R X10 )-, -[O-Si(R X11 ) 2 ] nx -, -Si(R X12 ) 2 -.
  • the definitions of R X10 , R X11 , R X12 and nx are as described above. Two R X11 may be the same or different.
  • the divalent hydrocarbon group in L X10 and L X11 includes a divalent aliphatic hydrocarbon group and a divalent aromatic hydrocarbon group.
  • the divalent hydrocarbon group is preferably a divalent aliphatic hydrocarbon group, and more preferably an alkylene group.
  • the alkylene group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 2 to 25, and even more preferably 2 to 20.
  • R 1 X20 represents a hydrogen atom or a monovalent hydrocarbon group.
  • the definition of the monovalent hydrocarbon group in R 1 X20 is the same as the monovalent hydrocarbon group explained in the above-mentioned substituent X.
  • a represents a structure (group) represented by formula (a) described below.
  • mx represents an integer of 0 to 2.
  • mx is an integer of 0 or 1
  • multiple (L X11 -a) may be the same or different.
  • two R X20 may be the same or different.
  • R a1 , R a2 and R a3 each independently represent an alkyl group, an alkenyl group, an aryl group or an alkylenearyl group, which may have a substituent.
  • substituents include the above-mentioned substituent W, and among them, a halogen atom, an alkyl group, an alkylcarbonyl group, an alkyloxycarbonyl group, an alkylcarbonyloxy group or an alkoxy group is preferable.
  • the alkyl group include linear alkyl groups having 1 to 18 carbon atoms, and branched or cyclic alkyl groups having 3 to 18 carbon atoms.
  • alkenyl group examples include alkenyl groups having 2 to 12 carbon atoms. Specific examples include vinyl group, 1-propenyl group, 1-butenyl group, 1-methyl-1-propenyl group, 1-cyclopentenyl group, and 1-cyclohexenyl group.
  • the aryl group may, for example, be an aryl group having a carbon number of 6 to 12. Specific examples include a phenyl group, an ⁇ -methylphenyl group, and a naphthyl group.
  • the alkylenearyl group may, for example, be an alkylenearyl group having 7 to 30 carbon atoms.
  • the number of groups a contained in the substituent X is 1 or more, preferably 2 or more and more preferably 3 or more in terms of providing a better degree of orientation of the light absorption anisotropic film, and preferably 18 or less, more preferably 12 or less, even more preferably 9 or less, and particularly preferably 6 or less in terms of being able to further suppress orientation defects.
  • the repeating unit A is preferably a repeating unit A-1 represented by the following formula (A-1), in that the effects of the present invention are more excellent and the degree of orientation of the optically absorptive anisotropic film is more excellent.
  • R A1 , R A2 and R A3 are the same as those explained in formula (A) above, and R a1 , R a2 and R a3 are the same as those explained in formula (a) above.
  • m in formula (A-1) is an integer of 2 or more, multiple R a1 may be the same or different, multiple R a2 may be the same or different, and multiple R a3 may be the same or different.
  • L A1 represents a single bond, —O— or —NR Z —, where R Z represents a hydrogen atom or a substituent.
  • R Z represents a hydrogen atom or a substituent.
  • the substituent in R Z is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
  • L A1 is preferably —O— or NH—, and more preferably —O—.
  • L A2 represents a single bond or an (m+1)-valent linking group.
  • suitable examples of the (m+1) valent linking group for L A2 include (m+1) valent hydrocarbon groups having 1 to 10 carbon atoms which may have a substituent, in which some of the carbon atoms constituting the hydrocarbon group may be substituted with heteroatoms.
  • the substituent that the hydrocarbon group may have is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
  • the heteroatom include a silicon atom, an oxygen atom, and a nitrogen atom.
  • m represents an integer of 1 or more, and is preferably an integer of 2 or more, more preferably an integer of 3 or more, in order to provide a better degree of orientation of the light absorption anisotropic film. Also, in order to further suppress orientation defects, m is preferably an integer of 18 or less, more preferably an integer of 12 or less, even more preferably an integer of 9 or less, and particularly preferably an integer of 6 or less.
  • repeating unit A examples include repeating units corresponding to monomers represented by the following formulae K-1 to K-38.
  • the monomer represented by the following formula K-1 is referred to as "monomer K-1.”
  • the monomer represented by the formula K-29 is a mixture of monomers having different numbers of -(O-Si(CH 3 ) 2 )-, and therefore is represented by an average value of n ⁇ 11. Also, the same meaning is applicable to monomers with similar notations.
  • the content A1 of repeating unit A relative to the total repeating units (100 mass%) contained in polymer 1 is preferably 10.0 to 90.0 mass%, more preferably 10.0 to 80.0 mass%, and even more preferably 30.0 to 75.0 mass%.
  • the effect of the present invention is more excellent.
  • the content A1 of repeating unit A relative to the total repeating units (100 mass%) contained in polymer 1 is preferably 10.0 to 90.0 mass%, more preferably 20.0 to 90.0 mass%, and even more preferably 30.0 to 90.0 mass%.
  • the effect of the present invention is more excellent.
  • Repeating unit A may be contained in polymer 1 either alone or in combination of two or more types.
  • the content of repeating unit A refers to the total content of repeating unit A.
  • the repeating unit B is a repeating unit represented by the following formula (B). It is believed that the repeating unit B having an amide structure can improve the compatibility between the copolymer and the liquid crystal compound, which is likely the reason why an optically absorbing anisotropic film with fewer alignment defects was obtained.
  • R B1 , R B2 and R B3 each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group or an aryl group.
  • alkyl group in R B1 , R B2 and R B3 include linear alkyl groups having 1 to 18 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms) and branched or cyclic alkyl groups having 3 to 18 carbon atoms (preferably 3 to 9 carbon atoms, more preferably 3 to 6 carbon atoms).
  • R B1 , R B2 and R B3 includes a linear alkenyl group having 2 to 18 carbon atoms and a branched alkenyl group having 3 to 18 carbon atoms.
  • Specific examples include a vinyl group, an aryl group, a 2-butenyl group, and a 3-pentenyl group.
  • the aryl group in R B1 , R B2 and R B3 includes an aryl group having 6 to 30 carbon atoms (preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), specifically, a phenyl group, a 2,6-diethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a styryl group, a naphthyl group, a biphenyl group, and the like.
  • R B1 , R B2 and R B3 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom.
  • R B4 and R B5 each independently represent a hydrogen atom or a substituent. When R B4 and R B5 are substituents, R B4 and R B5 may be linked to form a ring.
  • the sum of the molecular weight of R B4 and the molecular weight of R B5 is preferably 200 or less, more preferably 100 or less, and even more preferably 70 or less.
  • the details of the reason for this are not clear, but it is roughly presumed as follows. That is, if the sum of the molecular weights is 100 or less, there is no steric hindrance of the substituents, and the specific copolymer does not inhibit the alignment of the liquid crystal compound and the dichroic material, and as a result, the degree of order of the liquid crystal is increased, and the degree of alignment of the light absorption anisotropic film is superior.
  • the lower limit of the total molecular weight of R B4 and R B5 is preferably 2 or more.
  • the substituents represented by R and R are preferably organic groups, more preferably organic groups having 1 to 15 carbon atoms, even more preferably organic groups having 1 to 12 carbon atoms, and particularly preferably organic groups having 1 to 8 carbon atoms, in terms of obtaining better effects of the present invention.
  • Examples of the organic group include linear, branched or cyclic alkyl groups, aromatic hydrocarbon groups and heterocyclic groups.
  • the alkyl group preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and even more preferably 1 to 8 carbon atoms.
  • a hydrogen atom of the alkyl group may be substituted by a halogen atom, a cyano group, an aryl group, a nitro group, -OZH1 , -C(O) ZH1 , -C(O ) OZH1 , -OC(O) ZH1 , -OC( O ) OZH1 , -NZH1ZH2 , -NZH1C(O)ZH2, -NZH1C(O)OZH2 , -C (O) NZH1ZH2 , -OC( O ) NZH1ZH2 , -NZH1C( O ) NZH2OZH3 , -SZH1 , -C(S ) ZH1 , -C(O)SZH1 or -SC(O ) ZH1 .
  • Z H1 , Z H2 and Z H3 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cyano group or a nitro group.
  • groups with which the hydrogen atom of the alkyl group may be substituted -OH, -COOH or an aryl group (a phenyl group is preferred) is preferred in terms of better effects of the present invention.
  • the hydrogen atoms of the aromatic hydrocarbon group and the hydrogen atoms of the heterocyclic group are selected from the group consisting of halogen atoms, cyano groups, alkyl groups having 1 to 10 carbon atoms, cyano groups, nitro groups, -OZ H1 , -C(O)Z H1 , -C(O)OZ H1 , -OC(O)Z H1 , -OC(O)OZ H1 , -NZ H1 Z H2 , -NZ H1 C(O)Z H2 , -NZ H1 C(O)OZ H2 , -C(O)NZ H1 Z H2 , -OC(O)NZ H1 Z H2 , -NZ H1 C(O)NZ H2 OZ H3 , -SZ H1 , -C(S)Z H1 , -C(O)SZ H1 , -SC(O)Z H1 ,
  • Z H1 , Z H2 and Z H3 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cyano group or a nitro group.
  • a hydrogen atom atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cyano group or a nitro group.
  • -OH and -B(OH) 2 are preferred in terms of achieving better effects of the present invention.
  • R B4 and R B5 are preferably each independently a hydrogen atom or an organic group having 1 to 15 carbon atoms.
  • the preferred embodiments of the organic group are as described above.
  • the ring formed by combining R B4 and R B5 is a heterocycle containing the nitrogen atom in formula (B), and may further contain a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom in the ring.
  • the ring formed by R B4 and R B5 being linked together is preferably a 4- to 8-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring, in terms of better effects of the present invention.
  • the number of carbon atoms constituting the ring formed by combining R B4 and R B5 is preferably 3 to 7, and more preferably 3 to 6, in terms of obtaining better effects of the present invention.
  • the ring formed by linking R and R may or may not have aromaticity; however, in terms of better effects of the present invention, it is preferable that the ring does not have aromaticity.
  • Specific examples of the ring formed by combining R B4 and R B5 include the following groups.
  • repeating unit B is not limited to the following structure.
  • the content of repeating unit B is preferably 2 to 75 mass%, more preferably 3 to 70 mass%, and even more preferably 5 to 65 mass%, based on the total repeating units (100 mass%) contained in polymer 1.
  • the repeating unit B may be contained in one type alone or in two or more types in the polymer 1.
  • the content of the repeating unit B means the total content of the repeating unit B.
  • the repeating unit D is a repeating unit represented by the following formula (D).
  • the repeating unit D has a predetermined spacer (Sp D1 in formula (B) described later) and a linking group having a predetermined ring structure (Cy D in formula (B) described later), which is believed to improve the viscosity of the liquid crystal composition and further suppress repelling.
  • the repeating unit D since the repeating unit D has a specific hydrogen-bonding group (D in formula (B) described later), it forms a polymer through hydrogen bonding and serves as an air-interface layer with high flatness suitable for aligning a liquid crystal compound and a dichroic substance, and it is considered that the degree of orientation of the optically absorptive anisotropic film formed is further improved.
  • L D1 represents a single bond, —COO— or —CO—, and is preferably —CO—.
  • the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferably an alkylene group having 1 to 15 carbon atoms, more preferably an alkylene group having 1 to 8 carbon atoms, and specific examples of suitable groups include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group.
  • one or two or more non-adjacent -CH 2 - may each be independently substituted with -O-, -S-, -NH- or -N(Q)-, where Q represents a substituent, and examples of the substituent W include the above-mentioned substituent W, and among these, an alkyl group, an alkoxy group or a halogen atom is preferable.
  • L D2 and L D3 each independently represent a single bond or a divalent linking group.
  • the divalent linking group in L D2 and L D3 include -C(O)O-, -O-, -S-, -C(O)NR L1 -, -SO 2 -, and -NR L1 R L2 -.
  • R L1 and R L2 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
  • the substituent that the alkyl group having 1 to 6 carbon atoms may have include the substituent W described above, and among them, an alkyl group, an alkoxy group, or a halogen atom is preferable.
  • CyD represents a divalent linking group containing a mesogenic group.
  • the mesogenic group is a group that represents the main skeleton of the liquid crystal molecule that contributes to the formation of liquid crystal.
  • the liquid crystal molecule exhibits liquid crystallinity, which is an intermediate state (mesophase) between a crystalline state and an isotropic liquid state.
  • the mesogenic group preferably contains 1 to 10 cyclic structures, and more preferably contains 1 to 7.
  • Specific examples of the cyclic structures include aromatic hydrocarbon groups, heterocyclic groups, and alicyclic groups.
  • the divalent linking group containing a mesogen group in Cy D is preferably a divalent mesogen group.
  • the divalent mesogen group include a divalent aromatic hydrocarbon group, a divalent heterocyclic group, and a divalent alicyclic group.
  • Specific examples of the divalent aromatic hydrocarbon group include a phenylene group, a naphthylene group, a fluorene-diyl group, an anthracene-diyl group, and a tetracene-diyl group.
  • the divalent heterocyclic group may be either aromatic or non-aromatic, but is preferably a divalent aromatic heterocyclic group from the viewpoint of further improving the degree of orientation.
  • Examples of the atoms other than carbon constituting the divalent aromatic heterocyclic group include a nitrogen atom, a sulfur atom, and an oxygen atom.
  • these atoms may be the same or different.
  • divalent aromatic heterocyclic groups include, for example, a pyridylene group (pyridine-diyl group), a pyridazine-diyl group, an imidazole-diyl group, a thienylene group (thiophene-diyl group), a quinolylene group (quinoline-diyl group), an isoquinolylene group (isoquinoline-diyl group), an oxazole-diyl group, a thiazole-diyl group, an oxadiazole-diyl group, a benzothiazole-diyl group, a benzothiadiazole-diyl group, a phthalimido-diyl group, a thienothiazole-diyl group, a thiazolothiazole-diyl group, a thienothiophene-diyl group, and a
  • divalent alicyclic group examples include a cyclopentylene group and a cyclohexylene group, and the carbon atom may be substituted with -O-, -Si( CH3 ) 2- , -N( ZM )- ( ZM represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom), -C(O)-, -S-, -C(S)-, -S(O)-, -SO2- , or a group consisting of a combination of two or more of these groups.
  • Cy D is a divalent linking group represented by any one of the following formulae (Cy D -1) to (Cy D -15).
  • * represents the bonding position with L D2 or L D3
  • the carbon atom constituting the ring structure in the following formulae may be substituted with a heteroatom or may have a substituent.
  • the substituent that the carbon atom constituting the ring structure may have include the above-mentioned substituent W, and among these, an alkyl group, an alkoxy group, or a halogen atom is preferable.
  • divalent linking group represented by any one of the above formulas (Cy D -1) to (Cy D -15) include a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,4-piperazine group, a 1,4-piperidine group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo(2,2,2)octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, and a pyrimidine-2,5-diyl group.
  • alkyl group examples include pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, 9-fluorenone-2,7-diyl, fluorene-2,7-diyl group, thienothiophene-3,6-diyl group, carbazole-3,6-diyl group, and carbazole-2,7-diyl group.
  • Cy D in the above formula (B) is preferably a divalent linking group represented by any one of the above formulae (Cy D -1), (Cy D -4), (Cy D -7), (Cy D -10) and (Cy D -13), and more preferably a divalent linking group represented by any one of the above formulae (Cy D -7) and (Cy D -13).
  • D represents a hydrogen-bonding group composed of a hydrogen atom and a nonmetallic atom of Groups 14 to 16 (periodic table), provided that the nonmetallic atom may have a substituent.
  • the non-metallic atoms of Groups 14 to 16 include oxygen atoms, sulfur atoms, nitrogen atoms, and carbon atoms.
  • examples of the substituent that a non-metallic atom may have include a halogen atom, an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (e.g., a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, and a hydroxyl group.
  • a halogen atom an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (e.g., a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, and a hydroxyl
  • hydrogen bond-forming groups include hydrogen bond donor groups and hydrogen bond accepting groups.
  • the hydrogen bond donor group include an amino group, an amide group, a urea group, a urethane group, a sulfonylamino group, a sulfo group, a phospho group, a hydroxy group, a mercapto group, a carboxy group, a methylene group substituted with an electron-withdrawing group, and a methine group substituted with an electron-withdrawing group.
  • the carboxy group and the amide group are preferable.
  • the hydrogen bond accepting group include a heteroatom having an unshared electron pair on a heterocycle, a hydroxy group, an aldehyde, a ketone, a carboxy group, a carboxylic acid ester, a carboxylic acid amide, a lactone, a lactam, a sulfonic acid amide, a sulfo group, a phospho group, a phosphoric acid amide, a urethane, a urea, an ether structure (particularly a polymer structure having an oxygen atom contained in a polyether structure), an aliphatic amine, and an aromatic amine.
  • the carboxy group and the amide group are preferred.
  • n represents an integer of 1 to 3.
  • n 2 or 3
  • multiple L D2 may be the same or different
  • multiple Cy D may be the same or different.
  • n in the above formula (D) is preferably 1 or 2 because the haze of the optically absorptive anisotropic film is less observable (the haze is better), and more preferably 2 because repelling is more suppressed when the optically absorptive anisotropic film is formed.
  • the repeating unit D is a repeating unit in which L D3 in the above formula (D) represents a single bond and D represents -COOH, -NHCOR 2 or -CONHR 3 .
  • R2 and R3 each independently represent an alkyl group or alkenyl group having 1 to 10 carbon atoms.
  • the alkyl group and alkenyl group may be linear or branched.
  • one or two or more non-adjacent -CH2- groups may be substituted with -O-.
  • the repeating unit D is preferably a repeating unit in which L D3 in the above formula (D) represents a single bond and D represents -NHCOR 4 , because this makes it more difficult to observe haze in the optically absorptive anisotropic film.
  • R4 represents an alkyl group or alkenyl group having 1 to 3 carbon atoms.
  • the alkyl group and alkenyl group may be linear or branched. However, among the -CH2- groups constituting a part of the alkyl group and alkenyl group, one or two or more non-adjacent -CH2- groups may be substituted with -O-.
  • Examples of the monomer that forms the repeating unit D include the monomer represented by the following formula.
  • Me represents a methyl group
  • Ac represents an acetyl group.
  • the content of repeating unit D is preferably 5 to 85 mass%, more preferably 10 to 75 mass%, and even more preferably 20 to 70 mass%, based on the total repeating units (100 mass%) contained in polymer 1.
  • the repeating unit D may be contained in one type alone or in two or more types in the polymer 1.
  • the content of the repeating unit D means the total content of the repeating unit D.
  • the repeating unit E is a repeating unit that does not contain a fluorine atom or a polymerizable group and satisfies the following condition 1 or the following condition 2.
  • Condition 1 The repeating unit E has a polar group at the end of the side chain.
  • Condition 2 The repeating unit E is represented by the following formula (E1) or (E2).
  • the repeating unit E satisfying condition 1 is a repeating unit having a polar group at the end of the side chain.
  • the polar group refers to a substituent that has a hydrogen atom and has a biased charge between the bond between the hydrogen atom and the atom to which the hydrogen atom is bonded, or an ion pair consisting of a deprotonated or protonated form of this substituent.
  • ring E represents a ring structure having a cationized nitrogen atom, as described above.
  • Ring E is preferably a ring structure represented by the following formula (E-1-1): In the following formula (E-1-1), * represents the bonding position with L E1 .
  • X represents an anion, as described above.
  • X include halogen anions (e.g., fluorine ion, chlorine ion, bromine ion, iodine ion, etc.), sulfonate ions (e.g., methanesulfonate ion, trifluoromethanesulfonate ion, methylsulfate ion, vinylsulfonate ion, allylsulfonate ion, p-toluenesulfonate ion, p-chlorobenzenesulfonate ion, p-vinylbenzenesulfonate ion, 1,3-benzenedisulfonate ion, 1,5-naphthalenedisulfonate ion, 2,6-naphthalenedisulfonate ion, etc.), sulfate ion, carbonate ion,
  • halogen anions sulfonate ions, and hydroxide ions.
  • Particularly preferred are chloride ion, bromide ion, iodide ion, methanesulfonate ion, vinylsulfonate ion, p-toluenesulfonate ion and p-vinylbenzenesulfonate ion.
  • L E2 represents a hydrogen atom or a substituent, as described above.
  • substituent represented by one embodiment of L E2 include the groups described above for the substituent W. Among them, an alkylamino group having 1 to 10 carbon atoms, an aliphatic hydrocarbon (e.g., an alkyl group having 1 to 20 carbon atoms), a heterocyclic group, and a cyano group are preferable.
  • R E4 and R E5 each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R E4 and R E5 may be linked to each other via an alkylene linking group, an arylene linking group, or a linking group consisting of a combination thereof.
  • the substituted or unsubstituted aliphatic hydrocarbon group represented by one embodiment of R E4 and R E5 includes an alkyl group, an alkenyl group, or an alkynyl group, each of which may have a substituent.
  • the alkyl group include linear, branched, or cyclic alkyl groups such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, hexadecyl group, octadecyl group, eicosyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, 1-methylbutyl group, isohexy
  • alkenyl group examples include straight-chain, branched, or cyclic alkenyl groups such as vinyl, 1-propenyl, 1-butenyl, 1-methyl-1-propenyl, 1-cyclopentenyl, and 1-cyclohexenyl groups.
  • alkynyl group examples include an ethynyl group, a 1-propynyl group, a 1-butynyl group, and a 1-octynyl group.
  • Examples of the substituted or unsubstituted aryl group represented by one embodiment of R E4 and R E5 include a fused ring formed by one to four benzene rings and a fused ring formed by a benzene ring and an unsaturated five-membered ring. Specific examples thereof include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, an indenyl group, an acenabutenyl group, a fluorenyl group, and a pyrenyl group.
  • Examples of the substituted or unsubstituted heteroaryl group represented by one embodiment of R E4 and R E5 include heteroaryl groups obtained by removing one hydrogen atom from a heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
  • heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom include pyrrole, furan, thiophene, pyrazole, imidazole, triazole, oxazole, isoxazole, oxadiazole, thiazole, thiadiazole, indole, carbazole, benzofuran, dibenzofuran, thianaphthene, dibenzothiophene, indazole benzimidazole, anthranil, benzisoxazole, benzoxazole, benzothiazole, purine, pyridine, pyridazine, pyrimidine, pyrazine, triazine, quinoline, acridine, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthyridine, phenanthroline, and pteridine.
  • R E4 and R E5 may have include the groups described above for the substituent W.
  • monomers that forms the repeating unit represented by formula (E-1) include the monomers represented by the following formulae I-1 to I-11.
  • monomers that forms the repeating unit represented by formula (E-2) include the monomers represented by formulas II-1 to II-12 below.
  • the repeating unit E that satisfies condition 2 is a repeating unit represented by the above formula (E-2), since this further suppresses the occurrence of surface unevenness.
  • Polymer 1 having a repeating unit E that satisfies condition 2 may further have a repeating unit E that satisfies the above-mentioned condition 1, i.e., a repeating unit having a polar group at the end of the side chain, and may also satisfy the above-mentioned condition 1.
  • the content of repeating unit E is preferably 5 to 70 mass%, more preferably 10 to 65 mass%, and even more preferably 15 to 60 mass%, based on the total repeating units (100 mass%) contained in polymer 1.
  • the repeating unit E may be contained in one type alone or in two or more types in the polymer 1.
  • the content of the repeating unit E means the total content of the repeating unit E.
  • the polymer 1 having the repeating unit E further has a repeating unit F containing a polymerizable group, for the reason that the adhesion between the optically absorptive anisotropic film and an adjacent layer is improved.
  • the repeating unit F is preferably a repeating unit represented by the following formula (F).
  • R F1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and among these, a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is preferable, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms is more preferable, and a hydrogen atom or a methyl group is even more preferable.
  • L F1 represents a single bond, or a divalent linking group selected from the group consisting of -O-, -S-, -COO-, -OCO-, -CONR L2 -, -NR L2 COO-, -CR L2 N-, a substituted or unsubstituted divalent aliphatic group, a substituted or unsubstituted divalent aromatic group, and combinations thereof, and R L2 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or -L F1 -Q F1 .
  • Q F1 represents a polymerizable group, similar to Q F1 in the above (F).
  • examples of the divalent aliphatic group and the divalent aromatic group represented by L F1 include those similar to those described for L E1 in the above formula (E-1), and examples of the alkyl group having 1 to 20 carbon atoms represented by R L2 include those similar to those described for R L1 in relation to the above formula (E-1).
  • Q F1 represents a polymerizable group.
  • the polymerizable group represented by Q F1 in the above formula (F) is preferably any polymerizable group selected from the group consisting of groups represented by the following formulas (F-1) to (F-7), more preferably any polymerizable group selected from the group consisting of groups represented by the following formulas (F-1) to (F-3), and further preferably a polymerizable group represented by the following formula (F-1) or (F-2).
  • R 30 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and two R 30 may be the same or different and may be linked to each other to form a ring structure.
  • Specific examples of the alkyl group having 1 to 5 carbon atoms represented by R 30 include a methyl group, an ethyl group, a propyl group, an isopropyl group, and an n-butyl group.
  • the repeating unit represented by formula (F-1) is preferably a repeating unit in which R F1 in formula (F-1) is a hydrogen atom or a methyl group, and L F1 in formula (F-1) is a divalent linking group selected from the group consisting of combinations of -O-, -COO-, -OCO-, and substituted or unsubstituted divalent aliphatic groups (preferably alkylene groups having 2 to 8 carbon atoms).
  • repeating unit F include repeating units represented by the following formula:
  • the content of repeating unit F is preferably from 1 to 30% by mass, and more preferably from 5 to 20% by mass, based on the total repeating units (100% by mass) contained in polymer 1.
  • the repeating unit F may be contained in the polymer 1 in a single type or in a combination of two or more types. When two or more types of repeating unit F are contained, the content of the repeating unit F means the total content of the repeating unit F.
  • the content of polymer 1 is preferably 0.001 to 0.500 parts by mass, more preferably 0.002 to 0.400 parts by mass, and even more preferably 0.003 to 0.300 parts by mass, based on the total solid content (100 parts by mass) of the liquid crystal composition. When the content of polymer 1 is within the above range, the effects of the present invention are more excellent.
  • the content of polymer 1 is preferably 0.001 to 0.530 parts by mass, more preferably 0.002 to 0.430 parts by mass, and even more preferably 0.003 to 0.320 parts by mass, relative to the total amount (100 parts by mass) of the liquid crystal compound and the dichroic substance in the liquid crystal composition. When the content of polymer 1 is within the above range, the effects of the present invention are more excellent.
  • the weight average molecular weight (Mw) of polymer 1 is preferably from 2,000 to 1,000,000, more preferably from 3,000 to 200,000, and even more preferably from 5,000 to 80,000, in terms of better effects of the present invention.
  • the weight average molecular weight (Mw) of polymer 1 is calculated in terms of polystyrene by gel permeation chromatography (EcoSEC HLC-8320GPC (manufactured by Tosoh Corporation) using tetrahydrofuran as an eluent at a flow rate of 0.35 mL/min and a temperature of 40° C.; the columns used are TSKgel Super HZM-H, TSKgel Super HZ4000, and TSKgel Super HZ200 (manufactured by Tosoh Corporation)).
  • the liquid crystal composition of the present invention contains polymer 2.
  • Polymer 2 has a repeating unit A including a structure represented by formula (A) above, and is a polymer different from polymer 1 above. It is preferable that polymer 2 is substantially free of fluorine atoms. Substantially free of fluorine atoms means that the total content of fluorine atoms contained in polymer 2 is 5 parts by mass or less per 100 parts by mass of polymer 2. The total content of fluorine atoms contained in polymer 2 is more preferably 3 parts by mass or less, and even more preferably 0 part by mass.
  • a polymer different from polymer 1 means a polymer with a different chemical structure from polymer 1, or a polymer with the same chemical structure as polymer 1 but with a different composition ratio.
  • Polymer 2 is preferably a polymer (copolymer) containing repeating unit A (preferably repeating unit A-1) and at least one of repeating unit B and repeating unit D, and more preferably a polymer (copolymer) containing repeating unit A (preferably repeating unit A-1), repeating unit B, and repeating unit D, in terms of facilitating the production of an optically absorptive anisotropic film exhibiting horizontal alignment (the angle ⁇ between the central axis of transmittance of the optically absorptive anisotropic film and the normal direction to the surface of the optically absorptive anisotropic film is more than 45° and not more than 90°) and in terms of providing better effects of the present invention.
  • polymer 2 is preferably a polymer (copolymer) containing a repeating unit A (preferably, a repeating unit A-1) and a repeating unit E satisfying condition 1 or condition 2 described below, and may further contain a repeating unit F.
  • Each repeating unit in polymer 2 i.e., repeating unit A, repeating unit B, repeating unit D, repeating unit E, and repeating unit F
  • each repeating unit in polymer 1 is similar to each repeating unit in polymer 1, including preferred embodiments, and therefore description thereof will be omitted.
  • the content A2 of repeating unit A relative to the total repeating units (100 mass%) contained in polymer 2 is preferably 5.0 to 50.0 mass%, more preferably 10.0 to 50.0 mass%, and even more preferably 10.0 to 40.0 mass%.
  • the effect of the present invention is more excellent.
  • the content A2 of repeating unit A relative to the total repeating units (100 mass%) contained in polymer 2 is preferably 5.0 to 70.0 mass%, more preferably 5.0 to 65.0 mass%, even more preferably 10.0 to 65.0 mass%, and particularly preferably 15.0 to 60.0 mass%.
  • the content of repeating unit A is within the above range, the effect of the present invention is more excellent.
  • Repeating unit A may be contained in polymer 2 in a single type or in two or more types.
  • the content of repeating unit A refers to the total content of repeating unit A.
  • the content of repeating unit B is preferably 5.0 to 90.0 mass%, more preferably 10.0 to 85.0 mass%, and even more preferably 15.0 to 80.0 mass%, based on the total repeating units (100 mass%) contained in polymer 2.
  • the repeating unit B may be contained in the polymer 2 in the form of one kind alone or in the form of two or more kinds.
  • the content of the repeating unit B means the total content of the repeating unit B.
  • the content of repeating unit D is preferably 10.0 to 90.0 mass%, more preferably 20.0 to 85.0 mass%, and even more preferably 25.0 to 80.0 mass%, based on the total repeating units (100 mass%) contained in polymer 2.
  • the repeating unit D may be contained in the polymer 2 in the form of one kind alone or in the form of two or more kinds.
  • the content of the repeating unit D means the total content of the repeating unit D.
  • the content of repeating unit E is preferably 5.0 to 80.0 mass%, more preferably 7.0 to 75.0 mass%, and even more preferably 9.0 to 70.0 mass%, based on the total repeating units (100 mass%) contained in polymer 2.
  • the repeating unit E may be contained in the polymer 2 in one type alone or in two or more types.
  • the content of the repeating unit E means the total content of the repeating unit E.
  • the content of repeating unit F is preferably 5.0 to 40.0 mass %, more preferably 10.0 to 30.0 mass %, based on all repeating units contained in polymer 2 (100 mass %).
  • the repeating unit F may be contained in the polymer 2 in one type alone or in two or more types. When two or more types of the repeating unit F are contained, the content of the repeating unit F means the total content of the repeating unit F.
  • the content of polymer 2 is preferably 0.005 to 1.500 parts by mass, more preferably 0.007 to 1.200 parts by mass, and even more preferably 0.010 to 1.000 parts by mass, based on the total solid content (100 parts by mass) of the liquid crystal composition. When the content of polymer 2 is within the above range, the effects of the present invention are more excellent.
  • the content of polymer 2 is preferably 0.005 to 1.450 parts by mass, more preferably 0.008 to 1.300 parts by mass, and even more preferably 0.010 to 1.250 parts by mass, based on the total amount (100 parts by mass) of the liquid crystal compound and the dichroic substance in the liquid crystal composition. When the content of polymer 2 is within the above range, the effects of the present invention are more excellent.
  • the weight average molecular weight (Mw) of the polymer 2 is preferably from 2,000 to 1,000,000, more preferably from 3,000 to 200,000, and even more preferably from 5,000 to 80,000, in terms of better effects of the present invention.
  • the Mw of Polymer 2 is calculated in the same manner as for Polymer 1.
  • A1/A2 The ratio represented by A1/A2 is preferably greater than 1, more preferably 1.1 or more, even more preferably 1.2 or more, and particularly preferably 1.3 or more, in that the degree of orientation is superior, and is preferably 8.0 or less, more preferably 7.50 or less, and even more preferably 7.0 or less, in that the occurrence of planar unevenness can be further suppressed.
  • A1 unit: mass %) means the content of repeating unit A contained in polymer 1 relative to all repeating units contained in polymer 1.
  • A2 (unit: mass %) means the content of repeating unit A contained in polymer 2 relative to all repeating units contained in polymer 2.
  • the ratio represented by X1/X2 is preferably greater than 1, more preferably 1.10 or more, even more preferably 1.370 or more, particularly preferably 3.000 or more, and is preferably 41.32 or less, more preferably 25.000 or less, and even more preferably 15.000 or less.
  • X1/X2 is greater than 1, the surface condition and the degree of orientation are more excellent.
  • X1/X2 is 41.32 or less, the surface condition and the degree of orientation are more excellent.
  • the ratio represented by X1/X2 is preferably greater than 1, more preferably 1.10 or more, even more preferably 2.000 or more, particularly preferably 4.000 or more, and is preferably 79.34 or less, more preferably 50.000 or less, and even more preferably 30.000 or less.
  • X1/X2 is greater than 1, the surface condition and the degree of orientation are more excellent.
  • X1/X2 is 79.34 or less, the surface condition and the degree of orientation are more excellent.
  • X1 is preferably 0.0016 to 0.057 parts by mass, more preferably 0.0040 to 0.0500 parts by mass, and even more preferably 0.0100 to 0.0450 parts by mass, in terms of better effects of the present invention.
  • X2 is preferably 0.0013 to 0.0500 parts by mass, more preferably 0.0030 to 0.0500 parts by mass, and even more preferably 0.0040 to 0.0300 parts by mass, in terms of better effects of the present invention.
  • X1 is preferably 0.0027 to 0.0546 parts by mass, more preferably 0.0055 to 0.0400 parts by mass, and even more preferably 0.0100 to 0.0500 parts by mass, in terms of better effects of the present invention.
  • X2 is preferably 0.0006 to 0.0437 parts by mass, more preferably 0.0010 to 0.0300 parts by mass, and even more preferably 0.0020 to 0.0200 parts by mass, in terms of better effects of the present invention.
  • the liquid crystal composition of the present invention may contain components other than the above-mentioned liquid crystal compound, dichroic substance, polymer 1 and polymer 2 (hereinafter, also referred to as "other components").
  • other components include an alignment agent, a polymerization initiator, and a solvent.
  • the liquid crystal composition of the present invention may contain an alignment agent.
  • the alignment agent include a boronic acid compound and an onium salt.
  • the boronic acid compound functions as a horizontal alignment agent or a vertical alignment agent.
  • the onium salt functions as a vertical alignment agent.
  • the alignment agent may be used alone or in combination of two or more kinds.
  • boronic acid compound a compound represented by formula (30) is preferred.
  • R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
  • R3 represents a substituent containing a (meth)acrylic group.
  • Specific examples of the boronic acid compound include the boronic acid compounds represented by general formula (I) described in paragraphs 0023 to 0032 of JP-A-2008-225281. As the boronic acid compound, the compounds exemplified below are also preferred.
  • onium salts include the onium salts described in paragraphs 0052 to 0058 of JP-A-2012-208397, the onium salts described in paragraphs 0024 to 0055 of JP-A-2008-026730, and the onium salts described in JP-A-2002-37777.
  • the content of the alignment agent is preferably 0.01 to 30 parts by mass, and more preferably 0.1 to 10 parts by mass, based on the total solid content mass of the liquid crystal composition.
  • the liquid crystal composition of the present invention may contain a polymerization initiator.
  • the polymerization initiator is not particularly limited, but is preferably a compound having photosensitivity, that is, a photopolymerization initiator.
  • a photopolymerization initiator various compounds can be used without any particular limitation. Examples of the photopolymerization initiator include ⁇ -carbonyl compounds (see U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (see U.S. Pat. No. 2,448,828), ⁇ -hydrocarbon-substituted aromatic acyloin compounds (see U.S. Pat. No.
  • a photopolymerization initiator commercially available products can be used, such as Irgacure 184, Irgacure 907, Irgacure 369, Irgacure 651, Irgacure 819, Irgacure OXE-01, and Irgacure OXE-02 manufactured by BASF.
  • the polymerization initiator may be used alone or in combination of two or more kinds.
  • the content of the polymerization initiator is preferably 0.01 to 30 parts by mass, and more preferably 0.1 to 15 parts by mass, based on the total solid content mass of the liquid crystal composition.
  • the liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability and the like.
  • the solvent include ketones (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, and cyclopentyl methyl ether), aliphatic hydrocarbons (e.g., hexane), alicyclic hydrocarbons (e.g., cyclohexane), aromatic hydrocarbons (e.g., benzene, toluene, xylene, and trimethylbenzene), halogenated carbons (e.g., dichloromethane, trichloromethane (chloroform), dichloroethane, dichlor
  • the solvent examples include organic solvents such as toluene, esters (e.g., methyl acetate, ethyl acetate, butyl acetate, diethyl carbonate, etc.), alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, 1,2-dimethoxyethane, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), amides (e.g., dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, etc.), and heterocyclic compounds (e.g., pyridine, etc.), as well as water.
  • organic solvents such as tolu
  • the content of the solvent is preferably 70 to 99% by mass, more preferably 83 to 97% by mass, and even more preferably 85 to 95% by mass, based on the total mass of the liquid crystal composition.
  • the optically absorptive anisotropic film of the present invention is an optically absorptive anisotropic film (optically absorptive anisotropic layer) formed using the above-mentioned liquid crystal composition of the present invention.
  • the method for producing the optically absorptive anisotropic film of the present invention is not particularly limited, but because the degree of orientation of the obtained optically absorptive anisotropic film is higher, a method comprising, in this order, a step of applying the above-mentioned liquid crystal composition onto an alignment film to form a coating film (hereinafter also referred to as the "coating film forming step") and a step of orienting the liquid crystal component contained in the coating film (hereinafter also referred to as the "orientation step”) is preferred (hereinafter also referred to as the present manufacturing method).
  • the liquid crystal component includes not only the above-mentioned liquid crystal compounds but also dichroic substances having liquid crystal properties. Each step will be described below.
  • the coating film forming step is a step of coating the above-mentioned liquid crystal composition on the alignment film to form a coating film.
  • a liquid crystal composition containing the above-mentioned solvent or by using a liquid crystal composition that has been made into a liquid such as a molten liquid by heating or the like, it becomes easy to apply the liquid crystal composition onto the alignment film.
  • the method for applying the liquid crystal composition include known methods such as roll coating, gravure printing, spin coating, wire bar coating, extrusion coating, direct gravure coating, reverse gravure coating, die coating, spraying, and inkjet.
  • the alignment film can be provided by such means as rubbing an organic compound (preferably a polymer) on the film surface, oblique deposition of an inorganic compound, formation of a layer having microgrooves, or accumulation of an organic compound (e.g., ⁇ -tricosanoic acid, dioctadecylmethylammonium chloride, methyl stearate, etc.) by the Langmuir-Blodgett method (LB film).
  • LB film Langmuir-Blodgett method
  • an alignment film formed by a rubbing treatment is preferred from the viewpoint of ease of control of the pretilt angle of the alignment film, and a photo-alignment film formed by irradiation with light is also preferred from the viewpoint of uniformity of alignment.
  • the thickness of the alignment film is preferably 0.01 to 10 ⁇ m, and more preferably 0.01 to 1 ⁇ m.
  • Photo-alignment materials used in the alignment film formed by light irradiation are described in many documents.
  • azo compounds described in JP-A-2006-285197, JP-A-2007-76839, JP-A-2007-138138, JP-A-2007-94071, JP-A-2007-121721, JP-A-2007-140465, JP-A-2007-156439, JP-A-2007-133184, JP-A-2009-109831, Japanese Patent No. 3883848, and Japanese Patent No. 4151746, and azo compounds described in JP-A-2002-229039 are used.
  • Preferred examples include aromatic ester compounds described in JP-A-2002-265541 and JP-A-2002-317013, maleimide and/or alkenyl-substituted nadimide compounds having a photo-orientable unit described in Japanese Patent Nos. 4205195 and 4205198, and photo-crosslinkable polyimides, polyamides, or esters described in JP-A-2003-520878, JP-A-2004-529220, or Japanese Patent No. 4162850. More preferred are azo compounds, photo-crosslinkable polyimides, polyamides, or esters.
  • a photo-alignment film formed from the above-mentioned material is irradiated with linearly polarized or non-polarized light to produce a photo-alignment film.
  • “irradiation with linearly polarized light” and “irradiation with non-polarized light” are operations for causing a photoreaction in a photoalignment material.
  • the wavelength of the light used varies depending on the photoalignment material used, and is not particularly limited as long as it is a wavelength necessary for the photoreaction.
  • the peak wavelength of the light used for photoirradiation is preferably 200 nm to 700 nm, and more preferably ultraviolet light with a peak wavelength of 400 nm or less.
  • Light sources used for light irradiation include commonly used light sources, such as lamps such as tungsten lamps, halogen lamps, xenon lamps, xenon flash lamps, mercury lamps, mercury xenon lamps, and carbon arc lamps, various lasers [e.g., semiconductor lasers, helium-neon lasers, argon ion lasers, helium-cadmium lasers, and YAG (yttrium aluminum garnet) lasers], light-emitting diodes, and cathode ray tubes.
  • lamps such as tungsten lamps, halogen lamps, xenon lamps, xenon flash lamps, mercury lamps, mercury xenon lamps, and carbon arc lamps
  • various lasers e.g., semiconductor lasers, helium-neon lasers, argon ion lasers, helium-cadmium lasers, and YAG (yttrium aluminum garnet) lasers
  • light-emitting diodes e.g.,
  • Means for obtaining linearly polarized light include a method using a polarizing plate (e.g., an iodine polarizing plate, a dichroic material polarizing plate, and a wire grid polarizing plate), a method using a prism-based element (e.g., a Glan-Thompson prism) or a reflective polarizer that utilizes the Brewster angle, or a method using light emitted from a polarized laser light source. Also, a filter or a wavelength conversion element may be used to selectively irradiate only light of the required wavelength.
  • a polarizing plate e.g., an iodine polarizing plate, a dichroic material polarizing plate, and a wire grid polarizing plate
  • a prism-based element e.g., a Glan-Thompson prism
  • a reflective polarizer that utilizes the Brewster angle
  • a filter or a wavelength conversion element may be used
  • the light is irradiated from the top or back surface of the alignment film perpendicularly or obliquely to the alignment film surface.
  • the incident angle of the light varies depending on the photoalignment material, but is preferably 0 to 90° (perpendicular), more preferably 40 to 90°.
  • the non-polarized light is obliquely irradiated onto the alignment film, preferably at an incident angle of 10 to 80°, more preferably at an incident angle of 20 to 60°, and even more preferably at an incident angle of 30 to 50°.
  • the irradiation time is preferably from 1 to 60 minutes, and more preferably from 1 to 10 minutes.
  • patterning is required, a method of irradiating light using a photomask the number of times required to create a pattern, or a method of writing a pattern using laser light scanning can be used.
  • the orientation step is a step of orienting the dichroic material contained in the coating film. This results in the optically absorptive anisotropic film of the present invention.
  • the orientation step it is considered that the dichroic material is oriented along the liquid crystal compound oriented by the orientation film.
  • the orientation step may include a drying treatment. By the drying treatment, components such as a solvent can be removed from the coating film. The drying treatment may be performed by leaving the coating film at room temperature for a predetermined time (for example, natural drying), or may be performed by heating and/or blowing air.
  • the dichroic substance contained in the liquid crystal composition may be aligned by the above-mentioned coating film forming step or drying treatment.
  • the coating film may be dried to remove the solvent from the coating film, whereby the dichroic substance contained in the coating film may be aligned, thereby obtaining the optically absorptive anisotropic film of the present invention.
  • the alignment step preferably includes a heat treatment, which allows the dichroic material contained in the coating film to be more aligned, thereby increasing the degree of alignment of the resulting optically absorptive anisotropic film.
  • the heat treatment is preferably performed at 10 to 250° C., more preferably 25 to 190° C.
  • the heating time is preferably 1 to 300 seconds, more preferably 1 to 60 seconds.
  • the orientation step may include a cooling treatment carried out after the heating treatment.
  • the cooling treatment is a treatment for cooling the coated film after heating to about room temperature (20 to 25°C). This further fixes the orientation of the dichroic material contained in the coated film, and the degree of orientation of the obtained optically absorptive anisotropic film is increased.
  • the cooling means is not particularly limited and can be carried out by a known method.
  • the present production method may include a step of curing the optically absorptive anisotropic film (hereinafter also referred to as a "curing step") after the above-mentioned alignment step.
  • the curing step is carried out, for example, by heating and/or light irradiation (exposure), and among these, the curing step is preferably carried out by light irradiation.
  • the light source used for curing may be various light sources such as infrared light, visible light, or ultraviolet light, but ultraviolet light is preferred.
  • ultraviolet light may be irradiated while heating during curing, or ultraviolet light may be irradiated through a filter that transmits only specific wavelengths.
  • the exposure may be carried out under a nitrogen atmosphere.
  • the curing of the optically absorptive anisotropic film proceeds by radical polymerization, it is preferable to carry out the exposure under a nitrogen atmosphere, since this reduces inhibition of polymerization caused by oxygen.
  • the thickness of the optically absorbing anisotropic film is not particularly limited, but in terms of the superior effect of the present invention, a thickness of 0.3 to 10 ⁇ m is preferred, and 0.5 to 9 ⁇ m is even more preferred.
  • the liquid crystal compound and the dichroic substance contained in the optically absorptive anisotropic film of the present invention are fixed in their alignment state.
  • One embodiment of the optically absorptive anisotropic film of the present invention is an embodiment in which the angle ⁇ between the central axis of transmittance of the optically absorptive anisotropic film and the normal direction to the surface of the optically absorptive anisotropic film (hereinafter also abbreviated as "transmittance central axis angle ⁇ ”) is more than 45° and not more than 90°, more preferably 75° or more and 90° or less, and even more preferably 80° or more and 90° or less.
  • a laminate having a light absorptive anisotropic film (polarizer) having a transmittance central axis angle ⁇ of more than 45° and not more than 90° and a ⁇ /4 plate (described later) is suitably used as a circular polarizing plate.
  • polarizer light absorptive anisotropic film
  • optically absorptive anisotropic film of the present invention include an embodiment in which the transmittance central axis angle ⁇ is 0° or more and 45° or less, more preferably 0° or more and 35° or less, and even more preferably 0° or more and less than 35°.
  • the central axis of transmittance means the direction that shows the highest transmittance when the transmittance is measured by changing the inclination angle (polar angle) and inclination direction (azimuth angle) relative to the normal direction of the optically absorptive anisotropic film surface.
  • the Mueller matrix at a wavelength of 550 nm is measured using AxoScan OPMF-1 (manufactured by Optoscience).
  • the azimuth angle at which the transmittance central axis is tilted is first found, and then, within a plane including the normal direction of the optically absorptive anisotropic film along that azimuth angle (a plane including the transmittance central axis and perpendicular to the film surface), the polar angle, which is the angle with respect to the normal direction of the optically absorptive anisotropic film surface, is changed from -70 to 70° in 1° increments, and the Mueller matrix at a wavelength of 550 nm is measured, and the transmittance of the optically absorptive anisotropic film is derived.
  • the central axis of transmittance means the direction of the absorption axis (the long axis direction of the molecule) of the dichroic material contained in the optically absorptive anisotropic film.
  • the transmittance central axis angle ⁇ can be set to a desired value, for example, by adjusting the type and content of the alignment agent.
  • the laminate of the present invention has an optically absorptive anisotropic film, and the optically absorptive anisotropic film may be disposed on a substrate.
  • an alignment film may be disposed between the substrate and the optically absorptive anisotropic film.
  • the substrate is preferably a transparent support.
  • the transparent support means a support having a visible light transmittance of 60% or more, preferably 80% or more, and more preferably 90% or more.
  • the transparent support is not particularly limited, and any known transparent resin film, transparent resin plate, transparent resin sheet, etc. may be used.
  • transparent resin films examples include cellulose acylate films (e.g., cellulose triacetate film (refractive index 1.48), cellulose diacetate film, cellulose acetate butyrate film, and cellulose acetate propionate film), polyethylene terephthalate films, polyethersulfone films, polyacrylic resin films, polyurethane resin films, polyester films, polycarbonate films, polysulfone films, polyether films, polymethylpentene films, polyether ketone films, and (meth)acrylonitrile films.
  • cellulose acylate films e.g., cellulose triacetate film (refractive index 1.48), cellulose diacetate film, cellulose acetate butyrate film, and cellulose acetate propionate film
  • polyethylene terephthalate films polyethersulfone films
  • polyacrylic resin films polyurethane resin films
  • polyester films polycarbonate films
  • polysulfone films polyether films
  • polymethylpentene films polyether ketone films
  • a cellulose acylate film which has high transparency, low optical birefringence, and is easy to produce, and is generally used as a protective film for a polarizing plate, is preferred, and a cellulose triacetate film is more preferred.
  • the thickness of the substrate is usually 20 to 100 ⁇ m. In the present invention, it is particularly preferable that the substrate is a cellulose ester film and that the thickness thereof is 20 to 70 ⁇ m.
  • optically absorptive anisotropic film of the present invention is as described above, and therefore the description thereof will be omitted.
  • the alignment film (alignment layer) is as described above, and therefore the description thereof will be omitted.
  • One of the preferred embodiments of the laminate of the present invention includes an optically absorptive anisotropic film (particularly, an optically absorptive anisotropic film having a transmittance central axis angle ⁇ of more than 45° and not more than 90°) and a ⁇ /4 plate.
  • Such a laminate (optical film) is preferably used as a circularly polarizing plate.
  • the ⁇ /4 plate is a plate having a ⁇ /4 function, specifically, a plate having a function of converting linearly polarized light of a certain wavelength into circularly polarized light (or circularly polarized light into linearly polarized light).
  • specific examples of the ⁇ /4 plate having a single layer structure include a stretched polymer film and a retardation film having a light absorbing anisotropic film having ⁇ /4 function provided on a support
  • specific examples of the ⁇ /4 plate having a multilayer structure include a broadband ⁇ /4 plate formed by laminating a ⁇ /4 plate and a ⁇ /2 plate.
  • the ⁇ /4 plate and the optically absorptive anisotropic film may be provided in contact with each other, or another layer may be provided between the ⁇ /4 plate and the optically absorptive anisotropic film.
  • Such layers include an adhesive layer or a bonding layer for ensuring adhesion, and a barrier layer.
  • Another preferred embodiment of the laminate of the present invention includes an optically absorptive anisotropic film (particularly an optically absorptive anisotropic film having a transmittance central axis angle ⁇ of 0° or more and 45° or less) and a polarizer having an in-plane absorption axis.
  • Such a laminate optical film
  • the polarizer is preferably disposed on the opposite side of the optically absorptive anisotropic film to the substrate.
  • the polarizer may be disposed in contact with the surface of the optically absorptive anisotropic film, or may be disposed on the surface of the optically absorptive anisotropic film via another layer (for example, a known adhesive layer or pressure-sensitive adhesive layer).
  • the polarizer is not particularly limited as long as it has an absorption axis in the plane and has a function of converting light into a specific linearly polarized light, and a conventionally known polarizer can be used.
  • a conventionally known polarizer can be used as the polarizer.
  • an iodine-based polarizer, a dye-based polarizer using a dichroic dye, a polyene-based polarizer, etc. are used.
  • the iodine-based polarizer and the dye-based polarizer include a coating type polarizer and a stretching type polarizer, and either of them can be used.
  • polarizer a polarizer in which a dichroic organic dye is oriented by utilizing the orientation of a liquid crystal compound is preferred, and as a stretched polarizer, a polarizer produced by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching it is preferred.
  • optically absorptive anisotropic film examples include an optically absorptive anisotropic film containing a dichroic dye compound that is horizontally aligned (in a direction intersecting the thickness direction of the optically absorptive anisotropic film) and does not contain a liquid crystal compound as described in JP 2010-152351 A, and an optically absorptive anisotropic film containing a liquid crystal compound and a horizontally aligned dichroic dye compound as described in WO 2017/154907 A.
  • the laminate of the present invention preferably has a barrier layer in addition to the optically absorptive anisotropic film.
  • the barrier layer is also called a gas barrier layer (oxygen barrier layer), and has the function of protecting the polarizing element of the present invention from gases such as oxygen in the atmosphere, moisture, or compounds contained in adjacent layers.
  • the laminate of the present invention preferably has a barrier layer having an oxygen permeability coefficient of 200 cc/ m2 day atm or less adjacent to the optically absorptive anisotropic film, and more preferably has a barrier layer having an oxygen permeability coefficient of 50 cc/ m2 day atm or less, for the reason of further improving durability.
  • the barrier layer does not need to be provided.
  • the oxygen permeability coefficient is an index representing the amount of oxygen passing through a membrane per unit time and unit area, and in the present invention, a value measured with an oxygen concentration device (e.g., Model 3600 manufactured byhack Ultra Analytical Co., Ltd.) in an environment of 25°C and 50% relative humidity (RH) is used.
  • the organic compounds contained in the barrier layer include polymerizable compounds with high hydrogen bonding properties and compounds with many polymerizable groups per molecular weight, due to their high oxygen blocking function.
  • Examples of compounds with many polymerizable groups per molecular weight include pentaerythritol tetra(meth)acrylate and dipentaerythritol hexa(meth)acrylate.
  • polymerizable compounds with high hydrogen bonding properties include epoxy compounds, specifically compounds represented by the following formula, of which 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate represented by CEL2021P below is preferred.
  • the laminate of the present invention may or may not have a pressure-sensitive adhesive layer.
  • the adhesive that constitutes the adhesive layer includes a pressure sensitive adhesive and an adhesive.
  • adhesives include rubber-based adhesives, acrylic-based adhesives, silicone-based adhesives, urethane-based adhesives, vinyl alkyl ether-based adhesives, polyvinyl alcohol-based adhesives, polyvinylpyrrolidone-based adhesives, polyacrylamide-based adhesives, and cellulose-based adhesives, with acrylic-based adhesives (pressure-sensitive adhesives) being preferred.
  • the adhesive include polyvinyl alcohol adhesive (water glue), solvent-based adhesive, emulsion-based adhesive, solventless adhesive, active energy ray curable adhesive, and heat curable adhesive.
  • the active energy ray curable adhesive include electron beam curable adhesive, ultraviolet ray curable adhesive, and visible light curable adhesive, and ultraviolet ray curable adhesive is preferred.
  • the thickness of the adhesive layer is not particularly limited, but from the viewpoint of thinning, it is preferably 25 ⁇ m or less, more preferably 15 ⁇ m or less, and even more preferably 5 ⁇ m or less. There is no particular lower limit, and it is often 0.1 ⁇ m or more.
  • the pressure-sensitive adhesive layer with a function of improving the durability of the barrier layer, thereby eliminating the barrier layer and configuring the optically absorptive anisotropic film and the pressure-sensitive adhesive layer adjacent to each other.
  • a configuration in which an alignment layer/a light-absorptive anisotropic film/a pressure-sensitive adhesive layer/a retardation layer are arranged adjacent to each other may be mentioned.
  • the adhesive layer is preferably, for example, an adhesive containing polyvinyl alcohol as a main component, a UV (ultraviolet) adhesive with low oxygen permeability, or a pressure-sensitive adhesive having a hydrophilic group-containing polymer.
  • the display device (image display device) of the present invention comprises the above-mentioned light absorption anisotropic film (preferably the above-mentioned laminate) and a display element.
  • the optically absorptive anisotropic film and the liquid crystal cell may be laminated via a known adhesive layer or pressure-sensitive adhesive layer.
  • the display element used in the display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as "EL") display panel, and a plasma display panel. Among these, a liquid crystal cell or an organic EL display panel is preferable.
  • the display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element, or an organic EL display device using an organic EL display panel as a display element.
  • Some image display devices are thin and can be molded into a curved surface.
  • the optically absorptive anisotropic film used in the present invention is thin and easily bendable, and therefore can be suitably applied to image display devices having a curved display surface.
  • Some image display devices have a pixel density of more than 250 ppi, making it possible to display images with high resolution.
  • the optically absorptive anisotropic film used in the present invention can be suitably applied to such high resolution image display devices without causing moire.
  • a preferred embodiment of a liquid crystal display device which is one example of the display device of the present invention, includes the above-mentioned viewing angle control film and a liquid crystal cell.
  • the viewing angle control film is disposed on the front polarizing plate or the rear polarizing plate, which makes it possible to control the viewing angle by blocking light in the vertical or horizontal directions.
  • a viewing angle control film may be disposed on both the front-side polarizing plate and the rear-side polarizing plate. With such a configuration, it is possible to control the viewing angle so that light is blocked in all directions and only light is transmitted in the front direction.
  • a plurality of viewing angle control films may be laminated via a retardation layer.
  • the transmission performance and the light blocking performance can be controlled.
  • a polarizer By controlling the retardation value and the optical axis direction, the transmission performance and the light blocking performance can be controlled.
  • a polarizer By arranging a polarizer, a viewing angle control film, a ⁇ /2 wavelength plate (the axis angle is an angle shifted by 45° with respect to the orientation direction of the polarizer), and a viewing angle control film, it is possible to control the viewing angle so that light is blocked in all directions and only the front direction is transmitted.
  • a positive A plate, a negative A plate, a positive C plate, a negative C plate, a B plate, an O plate, etc. can be used.
  • the thickness of the retardation layer is preferably thin as long as it does not impair the optical properties, mechanical properties, and manufacturability, specifically, 1 to 150 ⁇ m is preferable, 1 to 70 ⁇ m is more preferable, and 1 to 30 ⁇ m is even more preferable.
  • the liquid crystal cell constituting the liquid crystal display device will be described in detail below.
  • the liquid crystal cell used in the liquid crystal display device is preferably in a VA (Vertical Alignment) mode, an OCB (Opticaly Compensated Bend) mode, an IPS (In-Plane-Switching) mode, or a TN (Twisted Nematic) mode, but is not limited thereto.
  • VA Vertical Alignment
  • OCB Opticaly Compensated Bend
  • IPS In-Plane-Switching
  • TN Transmission Nematic
  • rod-shaped liquid crystal molecules are aligned substantially horizontally when no voltage is applied, and further aligned in a twisted manner at an angle of 60 to 120°.
  • TN mode liquid crystal cells are most commonly used as color TFT liquid crystal display devices, and are described in many publications.
  • VA mode liquid crystal cell In a VA mode liquid crystal cell, rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied.
  • the VA mode liquid crystal cells include (1) a narrow-sense VA mode liquid crystal cell (described in JP-A-2-176625) in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when voltage is applied, (2) a VA mode (MVA mode) liquid crystal cell in which the VA mode is multi-domained to widen the viewing angle (described in SID97, Digest of tech.
  • liquid crystal display may be of any of a PVA (Patterned Vertical Alignment) type, an optical alignment type, and a PSA (Polymer-Sustained Alignment) type. Details of these modes are described in detail in JP-A-2006-215326 and JP-A-2008-538819.
  • liquid crystal compounds In IPS mode liquid crystal cells, the liquid crystal compounds are aligned substantially parallel to the substrate, and the liquid crystal molecules respond in a planar manner when an electric field parallel to the substrate surface is applied. That is, when no electric field is applied, the liquid crystal compounds are aligned in-plane.
  • the display In IPS mode, when no electric field is applied, the display is black, and the absorption axes of the pair of upper and lower polarizing plates are perpendicular to each other.
  • An organic EL display device which is an example of the display device of the present invention, preferably has, for example, the above-mentioned circular polarizer and an organic EL display panel in this order from the viewing side.
  • the substrate, the light absorption anisotropic film, and the ⁇ /4 plate are arranged in this order from the viewing side.
  • the organic EL display panel is a display panel configured using organic EL elements each having an organic light-emitting layer (organic electroluminescence layer) sandwiched between electrodes (a cathode and an anode).
  • the configuration of the organic EL display panel is not particularly limited, and a known configuration may be adopted.
  • the image display device of the present invention may include a reflective linear polarizer.
  • the reflective linear polarizer exhibits the effect of reflecting a part of the light emitted from the image display panel and causing the light to travel back and forth inside the optical system. From the viewpoint of suppressing stray light and ghosts, the reflective linear polarizer preferably has a high degree of polarization.
  • As the reflective linear polarizer a film obtained by stretching a dielectric multilayer film, a wire grid polarizer, etc., as described in JP 2011-053705 A, etc., can be used.
  • a reflective polarizer product name: APF, IQPE
  • WGF wire grid polarizer manufactured by Asahi Kasei Corporation, etc.
  • a first aspect of a virtual reality display device which is an example of a display device of the present invention, is a virtual reality display device having, in this order, an image display panel, a first absorbing linear polarizer (light absorbing anisotropic film), a first retardation layer, a second retardation layer, a reflective linear polarizer, a third retardation, a half mirror, and the second absorbing linear polarizer (light absorbing anisotropic film).
  • a second aspect is a virtual reality display device having, in this order, an image display panel, a first absorbing linear polarizer, a first retardation layer, a half mirror, a reflective circular polarizer, a second retardation layer, and a second absorbing linear polarizer.
  • a third aspect is a virtual reality display device having, in this order, an image display panel, a first absorbing linear polarizer, a first retardation layer, a half mirror, a second retardation layer, a reflective linear polarizer, and a second absorbing linear polarizer. Furthermore, it is also preferable that a fourth retardation layer be provided on the viewing side of the second absorptive linear polarizer.
  • the virtual reality display device of the present invention can use a curved substrate having a lens shape as a base material (for example, a member between the second retardation layer 12 and the half mirror 40 in FIG. 1).
  • the optically absorptive anisotropic film or laminate of the present invention can be processed into a three-dimensional curved surface for use.
  • Fig. 1 is a side view showing an embodiment of a virtual reality display device according to the present invention.
  • 1 includes, from the viewing side, a second absorbing linear polarizer 22, a second retardation layer 12, a half mirror 40, an anti-reflection layer 50, a reflective circular polarizer 30, a positive C plate 60, a first retardation layer 11, a first absorbing linear polarizer 21, a third retardation layer 13, and an image display panel 70, which are arranged in this order.
  • Example 1-1 The surface of a cellulose acylate film (TAC substrate with a thickness of 60 ⁇ m; TG60, Fujifilm Corporation) was saponified with an alkaline solution, and the following composition for forming an alignment film P1 was applied thereon with a wire bar.
  • the support on which the coating film was formed was dried with hot air at 60° C. for 60 seconds and then with hot air at 100° C. for 120 seconds to form an alignment film P1.
  • a rubbing treatment number of rotations of the roller: 1000 rotations/spacer thickness 1.8 mm, stage speed 1.8 m/min
  • the thickness of the alignment film P1 was 1 ⁇ m.
  • the film thickness of the optically absorbing anisotropic film 1-1 was 1.0 ⁇ m.
  • the numerical value in parentheses for each repeating unit indicates the content (mass %) of each repeating unit relative to the total repeating units contained in each polymer, and Mw is the weight average molecular weight.
  • the liquid crystal compound L1 is a high molecular weight liquid crystal compound
  • the liquid crystal compound L5 is a low molecular weight liquid crystal compound.
  • the following barrier composition was continuously applied onto the optically absorptive anisotropic film 1-1 using a wire bar.
  • the composition was then dried at 80° C. and irradiated for 2 seconds using an LED lamp (center wavelength 365 nm) at an illuminance of 200 mW/cm2 to obtain a laminate H1 having a barrier layer BA1.
  • the thickness of the barrier layer was 1.0 ⁇ m.
  • Examples 1-2 to 1-10, Comparative Examples 1-1 to 1-2 The composition of the optically absorptive anisotropic film-forming composition (liquid crystal composition) 1-1 was changed to the composition shown in Table 1 below, and the type of the alignment film was changed to that shown in Table 1 below. In the same manner as in Example 1-1, the laminates of Examples 1-2 to 1-10 and Comparative Examples 1-1 to 1-2 were obtained. The method for producing the alignment film P2 will be described below.
  • Orientation film P2 The following composition for forming an alignment film P2 was applied to a cellulose acylate film (TAC substrate having a thickness of 60 ⁇ m; TG60 manufactured by Fujifilm Corporation) using a wire bar.
  • the cellulose acylate film on which the coating film was formed was dried for 120 seconds with hot air at 140° C. to form an alignment film P2.
  • the coating film was then irradiated with polarized ultraviolet light (10 mJ/cm2, using an ultra-high pressure mercury lamp) to obtain a film with a photoalignment film.
  • the thickness of the alignment film P1 was 1.5 ⁇ m.
  • each repeating unit indicates the content (mass%) of each repeating unit relative to the total repeating units contained in each polymer.
  • the liquid crystal compounds L2 to L4 are high molecular weight liquid crystal compounds, and the liquid crystal compounds L6 to L12 are low molecular weight liquid crystal compounds.
  • Orientation degree: S ((Az0/Ay0)-1)/((Az0/Ay0)+2)
  • Az0 represents the absorbance of the optically absorptive anisotropic film for polarized light in the absorption axis direction
  • Ay0 represents the absorbance of the optically absorptive anisotropic film for polarized light in the transmission axis direction.
  • Transmittance central axis angle ⁇ When the transmittance central axis angle ⁇ was measured by the above-mentioned method using the laminates of the examples and the comparative examples, the transmittance central axis angle ⁇ was in the range of 80 to 90° for all of the laminates of the examples and the comparative examples. In addition, since none of the layer structures other than the optically absorptive anisotropic film in the laminate has absorption anisotropy, the transmittance central axis angle ⁇ calculated above can be interpreted as the value of the optically absorptive anisotropic film in the laminate.
  • Example 1-1 to 1-9 As shown in Table 1, it was shown that by using a liquid crystal composition containing polymer 1 and polymer 2 and having X1/X2 of 1 or more, surface unevenness can be suppressed and an optically absorptive anisotropic film having an excellent degree of orientation can be obtained (Examples 1-1 to 1-9). A comparison of Examples 1-1 to 1-8 with Example 1-9 shows that if A1/A2 is 7.50 or less, surface unevenness can be further suppressed. Comparing Examples 1-1 to 1-3, 1-5, and 1-7 to 1-9 with Examples 1-4 and 1-6, it was shown that if X1/X2 is 1.370 or more, surface unevenness can be further suppressed.
  • Example 2-1 The alignment film P1 used in Example 1-1, which had not been subjected to the rubbing treatment, was used as an alignment film P3.
  • a barrier layer BA1 was formed on the optically absorptive anisotropic film 2-1 in the same manner as in Example 1-1, to obtain a laminate V1.
  • Example 2-2 to 2-3 Comparative Examples 2-1 to 2-2
  • the laminates of Examples 2-2 to 2-3 and Comparative Examples 2-1 to 2-2 were obtained in the same manner as in Example 2-1, except that the composition of the optically absorptive anisotropic film-forming composition (liquid crystal composition) 2-1 was changed to the composition shown in Table 2 below.
  • each repeating unit indicates the content (mass%) of each repeating unit relative to the total repeating units contained in each polymer.
  • Orientation degree: S ((Az0/Ay0)-1)/((Az0/Ay0)+2)
  • Az0 represents the absorbance of the optically absorptive anisotropic film for polarized light in the absorption axis direction
  • Ay0 represents the absorbance of the optically absorptive anisotropic film for polarized light in the transmission axis direction.
  • Transmittance central axis angle ⁇ When the transmittance central axis angle ⁇ was measured by the above-mentioned method using the laminates of the examples and the comparative examples, the transmittance central axis angle ⁇ was in the range of 0 to 10° for all of the laminates of the examples and the comparative examples. In addition, since none of the layer structures other than the optically absorptive anisotropic film in the laminate has absorption anisotropy, the transmittance central axis angle ⁇ calculated above can be interpreted as the value of the optically absorptive anisotropic film in the laminate.
  • Example 2 As shown in Table 2, it was shown that by using a liquid crystal composition containing polymer 1 and polymer 2 and having X1/X2 of 1 or more, surface unevenness can be suppressed and an optically absorptive anisotropic film having an excellent degree of orientation can be obtained (Examples 2-1 to 2-3). Comparison of Examples 2-1 and 2-2 with Example 2-3 shows that, in order to obtain an optically absorptive anisotropic film exhibiting vertical alignment, the surface unevenness can be further suppressed by having at least one of polymer 1 and polymer 2 have a repeating unit E that satisfies the above-mentioned condition 2.

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  • Physics & Mathematics (AREA)
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  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
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Abstract

La présente invention aborde le problème consistant à fournir : une composition de cristaux liquides capable de former un film anisotrope absorbant la lumière dans lequel l'apparition d'une irrégularité plane est supprimée et qui a un excellent degré d'orientation ; un film anisotrope absorbant la lumière ; un stratifié ; et un dispositif d'affichage d'image. Une composition de cristaux liquides selon la présente invention comprend : un composé de cristaux liquides ; une substance dichroïque ; un polymère 1 ayant une unité de répétition A comprenant une structure représentée par la formule (A) ; et un polymère 2 qui a une unité de répétition A comprenant une structure représentée par la formule (A) et est différent du polymère 1. Lorsque la teneur en atomes de silicium contenus dans le polymère 1 est X1 parties en masse et la teneur en atomes de silicium contenus dans le polymère 2 est X2 parties en masse par rapport à 100 parties en masse de la masse totale de contenu solide de la composition de cristaux liquides, le rapport représenté par X1/X2 est supérieur ou égal à 1. Dans la formule (A), X représente un substituant contenant au moins une structure représentée par la formule (a).
PCT/JP2024/045890 2023-12-27 2024-12-25 Composition de cristaux liquides, film anisotrope absorbant la lumière, stratifié et dispositif d'affichage d'image Pending WO2025143020A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018003653A1 (fr) * 2016-06-27 2018-01-04 Dic株式会社 Composition de cristaux liquides polymérisable, ainsi qu'objet optiquement anisotrope et élément d'affichage à cristaux liquides obtenus tous deux à l'aide de celle-ci
WO2021039625A1 (fr) * 2019-08-28 2021-03-04 富士フイルム株式会社 Dispositif d'affichage à électroluminescence organique
JP2022043945A (ja) * 2020-09-04 2022-03-16 Jsr株式会社 光学異方体及びその製造方法、位相差板、偏光板並びに表示装置
WO2023054084A1 (fr) * 2021-09-30 2023-04-06 富士フイルム株式会社 Film optiquement anisotrope, plaque de polarisation circulaire et dispositif d'affichage
WO2024242041A1 (fr) * 2023-05-19 2024-11-28 富士フイルム株式会社 Composition de cristaux liquides, couche optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018003653A1 (fr) * 2016-06-27 2018-01-04 Dic株式会社 Composition de cristaux liquides polymérisable, ainsi qu'objet optiquement anisotrope et élément d'affichage à cristaux liquides obtenus tous deux à l'aide de celle-ci
WO2021039625A1 (fr) * 2019-08-28 2021-03-04 富士フイルム株式会社 Dispositif d'affichage à électroluminescence organique
JP2022043945A (ja) * 2020-09-04 2022-03-16 Jsr株式会社 光学異方体及びその製造方法、位相差板、偏光板並びに表示装置
WO2023054084A1 (fr) * 2021-09-30 2023-04-06 富士フイルム株式会社 Film optiquement anisotrope, plaque de polarisation circulaire et dispositif d'affichage
WO2024242041A1 (fr) * 2023-05-19 2024-11-28 富士フイルム株式会社 Composition de cristaux liquides, couche optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image

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