WO2024043149A1 - Film anisotrope d'absorption de lumière, film optique et dispositif d'affichage - Google Patents

Film anisotrope d'absorption de lumière, film optique et dispositif d'affichage Download PDF

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WO2024043149A1
WO2024043149A1 PCT/JP2023/029565 JP2023029565W WO2024043149A1 WO 2024043149 A1 WO2024043149 A1 WO 2024043149A1 JP 2023029565 W JP2023029565 W JP 2023029565W WO 2024043149 A1 WO2024043149 A1 WO 2024043149A1
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group
light
anisotropic film
film
light absorption
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PCT/JP2023/029565
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English (en)
Japanese (ja)
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渉 星野
隆志 加藤
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富士フイルム株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/60—Pleochroic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements

Definitions

  • the present invention relates to a light-absorbing anisotropic film, an optical film, and a display device.
  • Optical films such as optical compensation sheets and retardation films are used in various display devices from the viewpoint of eliminating image coloration and controlling viewing angles.
  • films having a light-absorbing anisotropic film containing a liquid crystal compound and a dichroic substance have been used as such optical films.
  • Patent Document 1 describes a light absorption anisotropic film obtained using a composition containing a liquid crystal compound, a dichroic substance having an azo group, and an oxidizing agent.
  • the present invention was made in view of the above problems, and an object of the present invention is to provide a light absorption anisotropic film having excellent light resistance, and an optical film and display device having the same.
  • the present inventors have discovered a light absorption anisotropic material containing a liquid crystal compound and a dichroic substance, in which the alignment state of the liquid crystal compound and the dichroic substance is fixed.
  • the inventors have discovered that the light resistance of the light-absorbing anisotropic film is improved by further including a compound represented by the below-mentioned formula (T) in the anisotropic film, and the present invention has been completed. That is, the present inventors have found that the above problem can be solved by the following configuration.
  • L t represents a single bond or a nt-valent linking group
  • Q t represents -C(R t2 ) 2 -
  • a plurality of R t1 each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may have a substituent
  • a plurality of R t2 each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms which may have a substituent
  • mt represents an integer from 0 to 2
  • nt represents an integer of 2 or more.
  • Ar1 and Ar2 each independently represent a phenylene group or a naphthylene group, which may have a substituent
  • R1 is a hydrogen atom or an alkyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylcarbonyl group, an alkyloxycarbonyl group, an acyloxy group, an alkyl carbonate group, an alkylamino group, which may have a substituent.
  • acylamino group alkylcarbonylamino group, alkoxycarbonylamino group, alkylsulfonylamino group, alkylsulfamoyl group, alkylcarbamoyl group, alkylsulfinyl group, alkylureido group, alkylphosphate amide group, alkylimino group, or alkyl represents a silyl group, and when R1 is an alkyl group, -CH 2 - in the alkyl group may be substituted with a divalent substituent, R2 and R3 are each independently a hydrogen atom, or an alkyl group, an alkoxy group, an acyl group, an alkyloxycarbonyl group, an alkylamido group, an alkylsulfonyl group, an aryl group, and an arylcarbonyl group, which may have a substituent.
  • An optical film comprising: a base material; the light-absorbing anisotropic film according to [5] disposed on the base material; and a ⁇ /4 plate disposed on the light-absorbing anisotropic film.
  • An optical film comprising a base material, the light absorption anisotropic film according to [6] disposed on the base material, and a polarizer having an absorption axis in the plane, and used for controlling the viewing angle.
  • a display device comprising the optical film according to any one of [7] to [10] and a display element.
  • the present invention it is possible to provide a light absorption anisotropic film with excellent light resistance, as well as an optical film and a display device having the same.
  • a numerical range expressed using " ⁇ " means a range that includes the numerical values written before and after " ⁇ " as the lower limit and upper limit.
  • 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 stepwise.
  • the upper limit or lower limit described in a certain numerical range may be replaced with the value shown in the Examples.
  • each component may use one type of substance corresponding to each component, or may use two or more types in combination.
  • the content of the component refers to the total content of the substances used in combination, unless otherwise specified.
  • a combination of two or more preferred embodiments is a more preferred embodiment.
  • “(meth)acrylate” is a notation representing "acrylate” or “methacrylate”
  • “(meth)acrylic” is a notation representing "acrylic” or “methacrylic”
  • “(meth)acrylate” 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 light absorption anisotropic film of the present invention includes a liquid crystal compound, a dichroic substance, and a compound represented by formula (T) described below, and the alignment state of the liquid crystal compound and the dichroic substance is Fixed.
  • the light absorption anisotropic film of the present invention has excellent light resistance. Although the details of this reason are not clear, it is generally estimated as follows. It is presumed that in the excited state in which the dichroic substance in the light-absorbing anisotropic film is photoexcited, the compound represented by formula (T) quickly receives electrons in the excited state, thereby deactivating the excited state.
  • the compound represented by formula (T) has two or more N-oxyl radicals in one molecule, so the function of improving the light resistance of the light-absorbing anisotropic film is more effectively expressed. It is thought that he did.
  • the light absorption anisotropic film of the present invention contains a compound represented by the following formula (T).
  • L t represents a single bond or an nt-valent linking group.
  • nt-valent linking group include aliphatic hydrocarbon groups which may have substituents. Note that when L t is a single bond, nt is 2.
  • L t is an aliphatic hydrocarbon group which may have a substituent
  • the aliphatic hydrocarbon group may be linear or branched. Further, the aliphatic hydrocarbon group may have a ring structure or may include a ring structure. Among these, it is preferable that the aliphatic hydrocarbon group is linear, since the degree of orientation of the light absorption anisotropic film is more excellent.
  • the aliphatic hydrocarbon group may be saturated or unsaturated.
  • One or more -CH 2 - possessed by the aliphatic hydrocarbon group is -O-, -CO-, -C(O)-O-, -C(O)-N(Rn)-, -O-C Substituted with a divalent substituent such as (O)-, -N(Rn)-C(O)-, arylene group (e.g., phenylene group), divalent heterocyclic group (e.g., pyridylene group), etc. Good too.
  • Rn represents a hydrogen atom or a straight or branched alkyl group having 1 to 6 carbon atoms. Note that the hydrogen atom of the arylene group may be substituted with a substituent (monovalent substituent).
  • the substituent (monovalent substituent) that the aliphatic hydrocarbon group may have are as described below, and among them, a halogen atom is preferred.
  • L t is an aliphatic hydrocarbon group which may have a substituent
  • the number of carbon atoms in L t is preferably 2 or more, more preferably 4 or more, and preferably 20 or less, and more preferably 18 or less. It is preferably 16 or less, more preferably 12 or less, and particularly preferably 12 or less.
  • the number of carbon atoms in L t is 2 or more, the light resistance of the light absorption anisotropic film is better.
  • the number of carbon atoms in L t is 18 or less, the degree of orientation of the light absorption anisotropic film is better.
  • Q t represents -C(R t2 ) 2 -, and the definition of R t2 is as described below.
  • each of the plurality of R t1 is independently a hydrogen atom or a carbon number of 1 to 12 which may have a substituent (preferably a carbon number of 1 to 6, more preferably a carbon number of 1 to 1). 4) represents an alkyl group.
  • the alkyl group in R t1 may be linear or branched, but is preferably linear. Specific examples of the substituent (monovalent substituent) that the alkyl group in R t1 may have are as described below, and among them, a fluorine atom, a chlorine atom, and a cyano group are preferable.
  • R t1 is preferably an unsubstituted alkyl group having 1 to 12 carbon atoms, and R t1 is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, since the light resistance of the light absorption anisotropic film is better. More preferably, it is an unsubstituted alkyl group having 1 to 4 carbon atoms.
  • a plurality of R t2 are each independently a hydrogen atom or a carbon number of 1 to 12 which may have a substituent (preferably a carbon number of 1 to 10, more preferably a carbon number of 1 to 10). 6) represents an alkyl group.
  • the alkyl group in R t2 may be linear or branched, but is preferably linear.
  • Specific examples of the substituent (monovalent substituent) that the alkyl group in R t2 may have are as described below, but among them, a fluorine atom, a chlorine atom, and a cyano group are preferable.
  • R t2 is a hydrogen atom in that the light resistance is more excellent.
  • mt represents an integer of 0 to 2, and is preferably 0 or 1, more preferably 1, from the viewpoint of better light resistance of the light absorption anisotropic film.
  • mt when mt is 0, it means that the ring containing the nitrogen atom shown in formula (T) is a 5-membered ring, and when mt is 1, it means that the ring containing the nitrogen atom shown in formula (T) is a 5-membered ring.
  • mt is 2 it means that the ring containing the nitrogen atom shown in formula (T) is a 7-membered ring.
  • nt represents an integer of 2 or more, preferably an integer of 2 to 6, more preferably 2 or 3 from the viewpoint of a better degree of orientation of the light absorption anisotropic film, 2 It is more preferable that
  • the compound represented by formula (T) is more preferably a compound represented by formula (T-1), since the degree of orientation and light resistance of the light-absorbing anisotropic film are better.
  • L t1 represents an aliphatic hydrocarbon group which may have a substituent.
  • the aliphatic hydrocarbon group in L t1 may be linear or branched. Further, the aliphatic hydrocarbon group may have a ring structure or may include a ring structure. Among these, it is preferable that the aliphatic hydrocarbon group is linear, since the degree of orientation of the light absorption anisotropic film is more excellent.
  • the aliphatic hydrocarbon group in L t1 may be saturated or unsaturated. Specific examples of the substituent (monovalent substituent) that the aliphatic hydrocarbon group in L t1 may have are as described below, and among them, a halogen atom is preferable.
  • the aliphatic hydrocarbon group in L t1 preferably has no substituent.
  • the number of carbon atoms in the aliphatic hydrocarbon group in L t1 is preferably 1 or more, more preferably 2 or more, and is preferably 18 or less, more preferably 14 or less, and even more preferably 10 or less.
  • the degree of orientation of the light absorption anisotropic film is better.
  • the molecular weight of the compound represented by formula (T) is preferably 400 or more, and preferably 500 or more, from the viewpoint of providing a light absorption anisotropic film with better light resistance.
  • the molecular weight of the compound represented by formula (T) is preferably 1000 or less, preferably 800 or less, and even more preferably 700 or less, from the viewpoint of providing a more excellent degree of orientation of the light-absorbing anisotropic film.
  • the content of the compound represented by formula (T) is preferably 0.05 to 5% by mass, more preferably 0.08 to 4% by mass, and 0.05 to 5% by mass, more preferably 0.08 to 4% by mass, based on the total mass of the light-absorbing anisotropic film. More preferably 1 to 3% by mass. If the content of the compound represented by formula (T) is 0.05% by mass or more, the light resistance of the light absorption anisotropic film will be more excellent. When the content of the compound represented by formula (T) is 5% by mass or less, the degree of orientation of the light-absorbing anisotropic film is better.
  • the content of the compound represented by formula (T) is preferably 1 to 20 parts by mass, more preferably 2 to 17 parts by mass, based on 100 parts by mass of the dichroic substance in the light-absorbing anisotropic film. More preferably 4 to 13 parts by mass. If the content of the compound represented by formula (T) is 1 part by mass or more, the light resistance of the light absorption anisotropic film will be more excellent. When the content of the compound represented by formula (T) is 20 parts by mass or less, the degree of orientation of the light-absorbing anisotropic film is more excellent.
  • the light absorption anisotropic film of the present invention contains a liquid crystal compound.
  • the dichroic substance can be oriented with a higher degree of orientation while suppressing precipitation of the dichroic substance.
  • the liquid crystal compound both a high molecular liquid crystal compound and a low molecular liquid crystal compound can be used, and a high molecular liquid crystal compound is preferable because it can increase the degree of orientation.
  • a high molecular liquid crystal compound and a low molecular liquid crystal compound may be used in combination.
  • the term "polymer liquid crystal compound” refers to a liquid crystal compound having repeating units in its chemical structure.
  • low-molecular liquid crystal compound refers to a liquid crystal compound that does not have repeating units in its chemical structure.
  • the polymeric liquid crystal compound include the thermotropic liquid crystalline polymer described in JP-A No. 2011-237513, and the polymer described in paragraphs [0012] to [0042] of International Publication No. 2018/199096.
  • Examples include molecular liquid crystal compounds.
  • the low-molecular liquid crystal compound include liquid crystal compounds described in paragraphs [0072] to [0088] of JP-A No. 2013-228706, and among them, liquid crystal compounds exhibiting smectic properties are preferred. Examples of such liquid crystal compounds include those described in paragraphs [0019] to [0140] of International Publication No. 2022/014340, and these descriptions are incorporated herein by reference.
  • the content of the liquid crystal compound is preferably 50 to 99% by mass, more preferably 75 to 90% by mass, based on the total mass of the light-absorbing anisotropic film, since the effect of the present invention is more excellent.
  • the light absorption anisotropic film of the present invention contains a dichroic substance.
  • a dichroic azo dye compound is preferable, and a dichroic azo dye compound usually used in a so-called coated polarizer can be used.
  • the dichroic azo dye compound is not particularly limited, and conventionally known dichroic azo dyes can be used, but the compounds described below are preferably used.
  • the dichroic substance may be polymerized in the light absorption anisotropic film.
  • a dichroic azo dye compound means a dye whose absorbance differs depending on the direction.
  • the dichroic azo dye compound may or may not exhibit liquid crystallinity.
  • the dichroic azo dye compound 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 (approximately 20° C. to 28° C.) to 300° C., and more preferably 50° C. to 200° C. from the viewpoint of handleability and manufacturing suitability.
  • the light absorption anisotropic film contains at least one dye compound (hereinafter referred to as "first dichroic azo dye”) having a maximum absorption wavelength in the wavelength range of 560 to 700 nm. and at least one type of dye compound (hereinafter also abbreviated as “second dichroic azo dye compound”) having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm.
  • first dichroic azo dye a dye compound having a maximum absorption wavelength in the wavelength range of 560 to 700 nm.
  • second dichroic azo dye compound having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm.
  • the dye has at least a dichroic azo dye compound represented by the formula (1) described below and a dichroic azo dye compound represented by the formula (2) described below. It is more preferable that
  • dichroic azo dye compounds may be used in combination.
  • a first dichroic azo dye compound and a second dichroic azo dye compound may be used together.
  • a dichroic azo dye compound of (also abbreviated as "dye compound") is preferably used in combination.
  • the dichroic azo dye compound has a crosslinkable group because the pressure resistance becomes better.
  • the crosslinkable group include a (meth)acryloyl group, an epoxy group, an oxetanyl group, and a styryl group, among which a (meth)acryloyl group is preferred.
  • the first dichroic azo dye compound is preferably a compound having a chromophore as a core and a side chain bonded to the terminal of the chromophore.
  • the chromophore include aromatic ring groups (e.g., aromatic hydrocarbon groups, aromatic heterocyclic groups), azo groups, etc., and structures having both aromatic ring groups and azo groups are preferred, More preferred is a bisazo structure having an aromatic heterocyclic group (preferably a thienothiazole group) and two azo groups.
  • the side chain is not particularly limited, and examples include groups represented by L3, R2, or L4 in formula (1) described below.
  • the first dichroic azo dye compound has a maximum absorption wavelength in the range of 560 nm or more and 700 nm or less (more preferably 560 to 650 nm, still more preferably 560 to 640 nm) from the viewpoint of adjusting the color of the light absorption anisotropic film.
  • the maximum absorption wavelength (nm) of the dichroic azo dye compound is a wavelength of 380 to 800 nm measured by a spectrophotometer using a solution in which the dichroic azo dye compound is dissolved in a good solvent. It is determined from the ultraviolet-visible light spectrum in the range.
  • the first dichroic azo dye compound is preferably a compound represented by the following formula (1) because the degree of orientation of the light-absorbing anisotropic film to be formed is further improved.
  • the dichroic substance contains a compound represented by the following formula (1), between the first dichroic azo dye compounds and between the first dichroic azo dye compound and the second dichroic dye compound, Due to the presumed reason that the interaction with the chromatic azo dye compound increases, the light resistance of the light-absorbing anisotropic film is further improved, and the degree of orientation of the light-absorbing anisotropic film is also better.
  • Ar1 and Ar2 each independently represent a phenylene group that may have a substituent or a naphthylene group that may have a substituent, and a phenylene group is preferred.
  • R1 is a hydrogen atom or an alkyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylcarbonyl group, an alkyloxycarbonyl group, an acyloxy group, an alkyl group that may have a substituent.
  • R1 is a group containing a carbon atom
  • the number of carbon atoms in R1 is preferably 1 or more, more preferably 3 or more, even more preferably 5 or more, particularly preferably 9 or more, and 10 or more from the viewpoint of a better degree of orientation. is most preferred.
  • the number of carbon atoms in R1 is preferably 20 or less, more preferably 18 or less, and even more preferably 15 or less.
  • R1 is an alkyl group or a group containing an alkyl group, the alkyl group may be linear or branched.
  • R1 is an alkyl group
  • R1 is a group other than a hydrogen atom
  • substituents monovalent substituents
  • R1' represents a hydrogen atom or a straight or branched alkyl group having 1 to 6 carbon atoms. In each group, when a plurality of R1's exist, they may be the same or different from each other.
  • R2 and R3 are each independently a hydrogen atom, or an alkyl group, an alkoxy group, an acyl group, an alkyloxycarbonyl group, an alkylamido group, an alkylsulfonyl group, which may have a substituent.
  • R2 and R3 represents an aryl group, an arylcarbonyl group, an arylsulfonyl group, an aryloxycarbonyl group, or an arylamido group.
  • R2 or R3 is an alkyl group
  • R2' represents a hydrogen atom or a straight or branched alkyl group having 1 to 6 carbon atoms.
  • each group when a plurality of R2's exist, they may be the same or different from each other.
  • R2 and R3 may be combined with each other to form a ring, or R2 or R3 may be combined with Ar2 to form a ring.
  • R1 is preferably an electron-withdrawing group
  • R2 and R3 are preferably groups with low electron-donating properties.
  • R1 includes an alkylsulfonyl group, an alkylcarbonyl group, an alkyloxycarbonyl group, an acyloxy group, an alkylsulfonylamino group, an alkylsulfamoyl group, an alkylsulfinyl group, and an alkylureido group.
  • R2 and R3 include groups having the following structures.
  • the group having the following structure is shown in the form containing the nitrogen atom to which R2 and R3 are bonded in the above formula (1).
  • the second dichroic azo dye compound is a compound different from the first dichroic azo dye compound, and specifically has a different chemical structure.
  • the second dichroic azo dye compound is preferably a compound having a chromophore, which is the core of the dichroic azo dye compound, and a side chain bonded to the terminal of the chromophore.
  • Specific examples of the chromophore include aromatic ring groups (e.g., aromatic hydrocarbon groups, aromatic heterocyclic groups), azo groups, etc., and structures having both aromatic hydrocarbon groups and azo groups are preferred. , a bisazo or trisazo structure having an aromatic hydrocarbon group and two or three azo groups is more preferred.
  • the side chain is not particularly limited, and includes groups represented by R4, R5, or R6 in formula (2) described below.
  • the second dichroic azo dye compound is a dichroic azo dye compound having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm.
  • a dichroic azo dye compound having a maximum absorption wavelength in the range of 555 nm is preferable, and a dichroic azo dye compound having a maximum absorption wavelength in the wavelength range of 455 to 550 nm is more preferable.
  • a first dichroic azo dye compound having a maximum absorption wavelength of 560 to 700 nm and a second dichroic azo dye compound having a maximum absorption wavelength of 455 nm or more but less than 560 nm are used, light absorption anisotropy can be achieved. It becomes easier to adjust the color of the sexual membrane.
  • the second dichroic azo dye compound is preferably a compound represented by formula (2) from the viewpoint of further improving the degree of orientation of the light absorption anisotropic film.
  • n 1 or 2.
  • Ar3, Ar4 and Ar5 each independently represent a phenylene group which may have a substituent, a naphthylene group which may have a substituent, or a hetero compound which may have a substituent. Represents a ring group.
  • the heterocyclic group may be aromatic or non-aromatic. Atoms other than carbon constituting the aromatic heterocyclic group include a nitrogen atom, a sulfur atom, and an oxygen atom. When the aromatic heterocyclic group has a plurality of atoms constituting a ring other than carbon, these may be the same or different.
  • aromatic heterocyclic groups include pyridylene group (pyridine-diyl group), pyridazine-diyl group, imidazole-diyl group, thienylene (thiophene-diyl group), quinolylene group (quinoline-diyl group), and isoquinolylene group.
  • R4 is the same as R1 in formula (1).
  • R5 and R6 are the same as R2 and R3 in formula (1), respectively.
  • R4 is preferably an electron-withdrawing group
  • R5 and R6 are preferably groups with low electron-donating properties.
  • specific examples where R4 is an electron-withdrawing group are the same as those where R1 is an electron-withdrawing group
  • R5 and R6 are groups with low electron-donating properties.
  • Specific examples in this case are the same as those in which R2 and R3 are groups with low electron donating properties.
  • the third dichroic azo dye compound is a dichroic azo dye compound other than the first dichroic azo dye compound and the second dichroic azo dye compound, and specifically, The chemical structure is different from the chromatic azo dye compound and the second dichroic azo dye compound. If the light-absorbing anisotropic film contains the third dichroic azo dye compound, there is an advantage that the color of the light-absorbing anisotropic film can be easily adjusted.
  • the maximum absorption wavelength of the third dichroic azo dye compound is 380 nm or more and less than 455 nm, preferably 385 to 454 nm. Specific examples of the third dichroic azo dye compound include the compound represented by formula (1) described in International Publication No. 2017/195833. compound and compounds other than the above-mentioned second dichroic azo dye compound.
  • n represents an integer of 1 to 10.
  • Me represents a methyl group.
  • the content of the dichroic substance is preferably 1% by mass or more, more preferably 2% by mass or more, based on the total mass of the light-absorbing anisotropic film, in terms of optical properties as a light-absorbing anisotropic film. , more preferably 3% by mass or more, particularly preferably 4% by mass or more.
  • the content of the dichroic substance is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less in terms of the degree of orientation, based on the total mass of the light-absorbing anisotropic film. , 30% by mass or less is particularly preferred.
  • the content of the first dichroic azo dye compound is preferably 40 to 90 parts by mass, and 45 to 85 parts by mass, based on 100 parts by mass of the entire dichroic substance in the light-absorbing anisotropic film. is more preferable.
  • the content of the second dichroic azo dye compound is preferably 4 to 50 parts by mass, and 5 to 35 parts by mass, based on 100 parts by mass of the entire dichroic substance in the light-absorbing anisotropic film. More preferred.
  • the content of the third dichroic azo dye compound is preferably 1 to 50 parts by mass, and 2 to 40 parts by mass based on 100 parts by mass of the entire dichroic substance in the light-absorbing anisotropic film. More preferred.
  • the content ratio of the first dichroic azo dye compound, the second dichroic azo dye compound, and the third dichroic azo dye compound used as necessary is determined based on the light absorption anisotropy. It can be set arbitrarily to adjust the color of the film. However, the content ratio of the second dichroic azo dye compound to the first dichroic azo dye compound (second dichroic azo dye compound/first dichroic azo dye compound) is expressed in molar terms. , preferably from 0.1 to 10, more preferably from 0.2 to 5, even more preferably from 0.3 to 0.8. If the content ratio of the second dichroic azo dye compound to the first dichroic azo dye compound is within the above range, the degree of orientation will be increased.
  • the light absorption anisotropic film of the present invention may contain components other than the liquid crystal compound, the dichroic substance, and the compound represented by formula (T) (hereinafter also referred to as "other components"). good. Specific examples of other components include surfactants, alignment agents, and the like.
  • the light absorption anisotropic film of the present invention preferably contains a surfactant.
  • a surfactant By including a surfactant, it is expected that the smoothness of the coated surface will be improved, the degree of orientation will be improved, and the in-plane uniformity will be improved by suppressing repellency and unevenness.
  • the surfactant fluorine (meth)acrylate polymers described in [0018] to [0043] of JP-A No. 2007-272185 can be used.
  • the surfactant compounds other than these may be used.
  • the surfactants may be used alone or in combination of two or more.
  • the content of the surfactant is preferably 0.1 to 2.0% by mass, and 0.1% by mass based on the total mass of the light absorption anisotropic film. ⁇ 1.0% by mass is more preferred.
  • the light absorption anisotropic film of the present invention may contain an alignment agent.
  • alignment agents include boronic acid compounds and onium salts.
  • the boronic acid compound functions as a horizontal or vertical alignment agent.
  • the onium salt also functions as a vertical alignment agent.
  • One type of alignment agent may be used alone, or two or more types may be used in combination.
  • boronic acid compound a compound represented by formula (30) is preferable.
  • 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. represent.
  • R 3 represents a substituent containing a (meth)acrylic group.
  • Specific examples of boronic acid compounds include boronic acid compounds represented by the general formula (I) described in paragraphs 0023 to 0032 of JP-A No. 2008-225281. As the boronic acid compound, the compounds exemplified below are also preferred.
  • onium salts include onium salts described in paragraphs 0052 to 0058 of JP2012-208397A, onium salts described in paragraphs 0024 to 0055 of JP2008-026730A, and Examples include onium salts described in Publication No. 2002-37777.
  • the content of the alignment agent is preferably 0.005 to 8% by mass, and 0.01 to 5% by mass, based on the total mass of the light absorption anisotropic film. is more preferable.
  • the substituent (monovalent substituent) in this specification means the following group unless otherwise specified.
  • substituents include: Alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 8 carbon atoms, such as methyl group, ethyl group, isopropyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.); Alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, even more preferably 2 to 8 carbon atoms, such as vinyl group, aryl group, 2-butenyl group, and - pentenyl group, etc.); Alkynyl group (preferably an alkynyl group (preferably an alky
  • Silyl group (preferably a silyl group having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, still more preferably 3 to 24 carbon atoms, such as trimethylsilyl group and triphenylsilyl group) ); Hydroxy group; Mercapto group; Cyano group; Nitro group; Hydroxamic acid group; Sulfino group; Hydrazino group; Imino group; Azo group; Carboxy group; Sulfonic acid group; Phosphoric acid group; Examples include.
  • One embodiment of the light-absorbing anisotropic film of the present invention includes an angle ⁇ (hereinafter referred to as "transmittance The 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°.
  • An optical film having a light absorption anisotropic film having a transmittance central axis angle ⁇ of 0° or more and 45° or less and a polarizer having an absorption axis in the plane is suitably used as a viewing angle control film.
  • the transmittance center axis refers to the highest transmittance when the transmittance is measured by changing the tilt angle (polar angle) and tilt direction (azimuthal angle) with respect to the normal direction of the light-absorbing anisotropic film surface. It means the direction of the rate.
  • the Mueller matrix at a wavelength of 550 nm is actually measured using AxoScan OPMF-1 (manufactured by Optoscience). More specifically, during measurement, first find the azimuth angle at which the transmittance center axis is tilted, and then find the plane ( The wavelength The Mueller matrix at 550 nm is actually measured to derive the transmittance of the light absorption anisotropic film.
  • the transmittance center axis means the direction of the absorption axis of the dichroic substance included in the light absorption anisotropic film (the direction of the long axis of the molecule).
  • the transmittance central axis angle ⁇ is more than 45° and less than 90°, more preferably 75° and more and less than 90°, and more preferably 75° and more than 90°; More preferably, the angle is at least 90°.
  • An optical film having a light absorption anisotropic film with a transmittance central axis angle ⁇ of more than 45° and less than 90°, a polarizer having an absorption axis in the plane, and a ⁇ /4 plate can be used as a circularly polarizing plate. Suitably used.
  • the transmittance central axis angle ⁇ can be set to a desired value by adjusting the type and content of the alignment agent, for example.
  • composition for forming light-absorbing anisotropic film is formed using a composition for forming a light-absorbing anisotropic film containing a liquid crystal compound, a dichroic substance, and a compound represented by formula (T). is preferred.
  • the composition for forming a light-absorbing anisotropic film preferably contains a polymerization initiator, a solvent, and the like. , may contain other components mentioned above.
  • the liquid crystal compound, the dichroic substance, and the compound represented by formula (T) contained in the composition for forming a light-absorbing anisotropic film of the present invention are, respectively, This is the same as the dichroic substance and the compound represented by formula (T).
  • the contents of the liquid crystal compound, the dichroic substance, and the compound represented by formula (T) with respect to the total solid mass of the composition for forming a light-absorbing anisotropic film of the present invention are respectively It is preferable that the content of the liquid crystal compound, the dichroic substance, and the compound represented by formula (T) be the same as the total mass of the liquid crystal compound, the dichroic substance, and the compound represented by formula (T).
  • total solid content in the composition for forming a light-absorbing anisotropic film refers to the components excluding the solvent, and specific examples of the solid content include liquid crystal compounds, dichroic substances, formula (T) Examples include the compound represented by and the other components mentioned above.
  • compositions for forming a light-absorbing anisotropic film are the same as other components that may be included in the light-absorbing anisotropic film of the present invention.
  • the content of the other components with respect to the total solid mass of the composition for forming a light-absorbing anisotropic film is the same as the content of the other components with respect to the total mass of the light-absorbing anisotropic film of the present invention. preferable.
  • the composition for forming a light-absorbing anisotropic film contains a polymerization initiator.
  • the polymerization initiator is not particularly limited, but it is preferably a photosensitive compound, that is, a photopolymerization initiator.
  • a photopolymerization initiator various compounds can be used without particular limitation. Examples of photopolymerization initiators include ⁇ -carbonyl compounds (US Pat. Nos. 2,367,661 and 2,367,670), asiloin ether (US Pat. No. 2,448,828), and ⁇ -hydrocarbon-substituted aromatic acyloins. compound (US Pat. No.
  • photopolymerization initiators such as Irgacure 184, Irgacure 907, Irgacure 369, Irgacure 651, Irgacure 819, Irgacure OXE-01 and Irgacure manufactured by BASF. Examples include OXE-02.
  • the polymerization initiators may be used alone or in combination of two or more.
  • the content of the polymerization initiator is 100 mass of the dichroic substance and liquid crystal compound in the composition for forming a light-absorbing anisotropic film. 0.01 to 30 parts by weight, more preferably 0.1 to 15 parts by weight.
  • the content of the polymerization initiator is 0.01 parts by mass or more, the durability of the light-absorbing anisotropic film becomes good, and when it is 30 parts by mass or less, the degree of orientation of the light-absorbing anisotropic film increases. It will be better.
  • the composition for forming a light-absorbing anisotropic film preferably contains a solvent from the viewpoint of workability.
  • the solvent include ketones (for example, acetone, 2-butanone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (for example, dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, and cyclopentyl methyl ether, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, and trimethyl benzene, etc.), halogenated carbons (e.g., dichloromethane, trichloromethane (ch)
  • solvents may be used alone or in combination of two or more.
  • organic solvents it is preferable to use organic solvents, and it is more preferable to use halogenated carbons or ketones because the effects of the present invention are better.
  • the content of the solvent is preferably 80 to 99% by mass, and 83 to 97% by mass based on the total mass of the composition for forming a light-absorbing anisotropic film. It is more preferably 85% to 95% by mass, and even more preferably 85 to 95% by mass.
  • the method for producing the light-absorbing anisotropic film of the present invention is not particularly limited, the above-described light-absorbing anisotropic film is formed on the alignment film because the obtained light-absorbing anisotropic film has a higher degree of orientation.
  • a step of applying a composition for forming a coating film hereinafter also referred to as a “coating film forming step”
  • a step of orienting a liquid crystal component contained in the coating film hereinafter also referred to as an "orientation step” in this order (hereinafter also referred to as "this manufacturing method") is preferable.
  • the liquid crystal component is a component that includes not only the above-mentioned liquid crystal compound but also a dichroic substance having liquid crystal properties.
  • the coating film forming step is a step of coating the above-described light-absorbing anisotropic film forming composition on the alignment film to form a coating film.
  • a light-absorbing anisotropic film-forming composition containing the above-mentioned solvent or by using a light-absorbing anisotropic film-forming composition made into a liquid such as a melt by heating, etc. It becomes easy to apply the composition for forming a light-absorbing anisotropic film onto the alignment film.
  • Application methods for the composition for forming a light-absorbing anisotropic film include roll coating method, gravure printing method, spin coating method, wire bar coating method, extrusion coating method, direct gravure coating method, reverse gravure coating method, and die coating method. , a spray method, and an inkjet method.
  • the alignment film can be formed by rubbing an organic compound (preferably a polymer) on the film surface, by oblique vapor deposition of an inorganic compound, by forming a layer with microgrooves, or by applying an organic compound (for example, ⁇ ) by the Langmuir-Blodgett method (LB film). -tricosanoic acid, dioctadecylmethylammonium chloride, methyl stearate, etc.).
  • alignment films are also known in which an alignment function is produced by applying an electric field, a magnetic field, or irradiation with light.
  • an alignment film formed by rubbing is preferred from the viewpoint of ease of controlling the pretilt angle of the alignment film, and a photo-alignment film formed by light irradiation is also preferred from the viewpoint of alignment uniformity.
  • Photo-alignment materials used for alignment films formed by light irradiation are described in numerous documents.
  • Preferable examples include the photocrosslinkable silane derivatives described in Japanese Patent Publication No. 2003-520878, Japanese Patent Publication No. 2004-529220, and photocrosslinkable polyimides, polyamides, or esters described in Japanese Patent No. 4162850. More preferred are azo compounds, photocrosslinkable polyimides, polyamides, or esters.
  • a photo-alignment film formed from the above material is irradiated with linearly polarized light or non-polarized light to produce a photo-alignment film.
  • linearly polarized light irradiation and “non-polarized light irradiation” 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 light irradiation is preferably 200 nm to 700 nm, more preferably ultraviolet light having a peak wavelength of 400 nm or less.
  • the light sources used for light irradiation include commonly used light sources, 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 Examples include neon lasers, argon ion lasers, helium cadmium lasers, and YAG (yttrium aluminum garnet) lasers, light emitting diodes, and cathode ray tubes.
  • various lasers e.g., semiconductor lasers, helium Examples include neon lasers, argon ion lasers, helium cadmium lasers, and YAG (yttrium aluminum garnet) lasers, light emitting diodes, and cathode ray tubes.
  • a polarizing plate for example, an iodine polarizing plate, a dichroic material polarizing plate, and a wire grid polarizing plate
  • a prism type element for example, a Glan-Thompson prism
  • a Brewster angle a method using a Brewster angle.
  • a method using a reflective polarizer, or a method using light emitted from a polarized laser light source can be adopted.
  • only light of a required wavelength may be selectively irradiated using a filter, a wavelength conversion element, or the like.
  • the irradiated light is linearly polarized light
  • a method is adopted in which the light is irradiated from the upper surface or the back surface of the alignment film perpendicularly or obliquely to the surface of the alignment film.
  • the incident angle of light varies depending on the photo-alignment material, but is preferably 0 to 90° (vertical), and preferably 40 to 90°.
  • the alignment film is irradiated with non-polarized light obliquely.
  • the angle of incidence is preferably 10 to 80 degrees, more preferably 20 to 60 degrees, and even more preferably 30 to 50 degrees.
  • the irradiation time is preferably 1 minute to 60 minutes, more preferably 1 minute to 10 minutes.
  • patterning is necessary, a method of applying light irradiation using a photomask as many times as necessary to create the pattern, or a method of writing a pattern by scanning a laser beam can be adopted.
  • the orientation step is a step of orienting the dichroic substance contained in the coating film.
  • the light absorption anisotropic film of the present invention is obtained.
  • the orientation process may include a drying process. Components such as solvents can be removed from the coating film by the drying process.
  • the drying treatment may be performed by leaving the coating film at room temperature for a predetermined period of time (for example, natural drying), or by heating and/or blowing air.
  • the dichroic substance contained in the composition for forming a light-absorbing anisotropic film may be oriented by the above-mentioned coating film forming step or drying treatment.
  • the composition for forming a light-absorbing anisotropic film is prepared as a coating solution containing a solvent
  • the solvent contained in the coating film can be removed by drying the coating film.
  • the light absorption anisotropic film of the present invention may be obtained by orientation of the colored substance.
  • the orientation step includes heat treatment.
  • the dichroic substance contained in the coating film is further oriented, and the degree of orientation of the resulting light-absorbing anisotropic film is further increased.
  • the heat treatment is preferably performed at 10 to 250°C, more preferably from 25 to 190°C, from the viewpoint of manufacturing suitability.
  • the heating time is preferably 1 to 300 seconds, more preferably 1 to 60 seconds.
  • the alignment step may include a cooling treatment performed after the heat treatment.
  • the cooling treatment is a treatment in which the coated film after heating is cooled to about room temperature (20 to 25° C.).
  • the cooling means is not particularly limited, and any known method can be used.
  • This manufacturing method may include a step of curing the light-absorbing anisotropic film (hereinafter also referred to as a "curing step") after the orientation step.
  • the curing step is performed, for example, by heating and/or light irradiation (exposure).
  • exposure it is preferable that the curing step is carried out by light irradiation.
  • Various light sources can be used for curing, such as infrared rays, visible light, or ultraviolet rays, but ultraviolet rays are preferred.
  • ultraviolet rays may be irradiated while heating during curing, or ultraviolet rays may be irradiated through a filter that transmits only a specific wavelength.
  • the exposure may be performed under a nitrogen atmosphere.
  • curing of the light-absorbing anisotropic film progresses by radical polymerization, it is preferable to perform exposure under a nitrogen atmosphere because inhibition of polymerization by oxygen is reduced.
  • the thickness of the light-absorbing anisotropic film is not particularly limited, but it is preferably 0.3 to 10 ⁇ m, more preferably 0.5 to 9 ⁇ m, since the effects of the present invention are more excellent.
  • the optical film of the present invention has a base material and the above-mentioned light-absorbing anisotropic film disposed on the base material, and has an alignment film between the base material and the light-absorbing anisotropic film. You may do so.
  • Each member constituting the optical film of the present invention will be explained below.
  • a known transparent resin film, transparent resin plate, transparent resin sheet, etc. can be used, and there is no particular limitation.
  • the transparent resin film include cellulose acylate film (for example, cellulose triacetate film (refractive index 1.48), cellulose diacetate film, cellulose acetate butyrate film, cellulose acetate propionate film), polyethylene terephthalate film, polyether sulfone.
  • Film, polyacrylic resin film, polyurethane resin film, polyester film, polycarbonate film, polysulfone film, polyether film, polymethylpentene film, polyetherketone film, (meth)acrylonitrile film, etc. can be used.
  • cellulose acylate film is preferred, and cellulose triacetate film is more preferred, as it has high transparency, low optical birefringence, and is easy to manufacture, and is commonly used as a protective film for polarizing plates.
  • the thickness of the base material is usually 20 ⁇ m to 100 ⁇ m. In the present invention, it is particularly preferable that the base material is a cellulose ester film and that the film thickness is 20 to 70 ⁇ m.
  • One of the preferred embodiments of the optical film of the present invention includes a light absorption anisotropic film having a transmittance central axis angle ⁇ of 0° or more and 45° or less, and a polarizer having an absorption axis in the plane. Examples include aspects. Such an optical film is suitably used as a viewing angle control film used to control the viewing angle.
  • the polarizer is preferably placed on the opposite side of the light-absorbing anisotropic film from the base material.
  • the polarizer may be placed in contact with the surface of the light-absorbing anisotropic film, or may be placed on the surface of the light-absorbing anisotropic film via another layer (for example, a known adhesive layer or adhesive layer). It may be placed in
  • the polarizer is not particularly limited as long as it has an absorption axis in the plane and has the function of converting light into a specific linearly polarized light, and any conventionally known polarizer can be used.
  • 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 stretched type polarizer, and either of them can be applied.
  • a polarizer in which a dichroic organic dye is oriented using the orientation of a liquid crystal compound is preferable.
  • a stretched polarizer a polarizer in which iodine or a dichroic dye is adsorbed to polyvinyl alcohol and stretched is preferable.
  • the polarizer produced is preferred.
  • a light-absorbing anisotropic film that does not contain a liquid crystal compound and contains a dichroic dye compound that is horizontally aligned (in a direction that intersects the thickness direction of the light-absorbing anisotropic film) described in JP-A No. 2010-152351.
  • a light absorption anisotropic film containing a liquid crystal compound and a horizontally aligned dichroic dye compound described in International Publication No. 2017/154907.
  • optical film of the present invention includes a light-absorbing anisotropic film having a transmittance center axis angle ⁇ of more than 45° and less than 90°, and a ⁇ /4 plate. It will be done.
  • Such an optical film is suitably used as a circularly polarizing plate.
  • a ⁇ /4 plate is a plate that has a ⁇ /4 function, and specifically, a plate that has the function of converting linearly polarized light of a certain wavelength into circularly polarized light (or from circularly polarized light to linearly polarized light).
  • the ⁇ /4 plate has a single layer structure include a stretched polymer film, a retardation film in which a light-absorbing anisotropic film having a ⁇ /4 function is provided on a support, etc.
  • a specific example of an embodiment in which the ⁇ /4 plate has a multilayer structure is a broadband ⁇ /4 plate formed by laminating a ⁇ /4 plate and a ⁇ /2 plate.
  • the ⁇ /4 plate and the light-absorbing anisotropic film may be provided in contact with each other, or another layer may be provided between the ⁇ /4 plate and the light-absorbing anisotropic film.
  • layers include an adhesive layer or adhesive layer for ensuring adhesion, and a barrier layer.
  • the optical film of the present invention preferably has a barrier layer together with the base material and the light-absorbing 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 barrier layer for example, paragraphs [0014] to [0054] of JP 2014-159124, paragraphs [0042] to [0075] of JP 2017-121721, and [0075] of JP 2017-115076. Reference can be made to paragraphs [0045] to [0054], paragraphs [0010] to [0061] of JP-A No. 2012-213938, and paragraphs [0021] to [0031] of JP-A No. 2005-169994.
  • a display device (image display device) of the present invention includes the above-described optical film and a display element.
  • the display element is preferably arranged on the polarizer side of the optical film (ie, on the opposite side to the base material).
  • the polarizer and the liquid crystal cell may be laminated via a known adhesive layer or adhesive layer.
  • the display element used in the display device of the present invention is not particularly limited, and includes, for example, a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as "EL") display panel, a plasma display panel, and the like. 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 curved surfaces.
  • the light-absorbing anisotropic film used in the present invention is thin and easy to bend, so it can be suitably applied to image display devices with curved display surfaces. Further, some image display devices have a pixel density exceeding 250 ppi and are capable of high-definition display.
  • the light-absorbing anisotropic film used in the present invention can be suitably applied to such high-definition image display devices without causing moiré.
  • Liquid crystal display device As a liquid crystal display device which is an example of the display device of the present invention, an embodiment including the above-mentioned viewing angle control film and a liquid crystal cell is preferably mentioned.
  • the viewing angle control film As a specific configuration, there is a configuration in which the viewing angle control film is disposed on the front polarizing plate or the rear polarizing plate. In these configurations, it is possible to control the viewing angle in which light is blocked in the vertical direction or the horizontal direction. Further, a viewing angle control film may be placed on both the front polarizing plate and the rear polarizing plate. With this configuration, it is possible to control the viewing angle so that light is blocked in all directions and light is transmitted only in the front direction.
  • a plurality of viewing angle control films may be laminated with a retardation layer interposed therebetween.
  • Transmission performance and light blocking performance can be controlled by controlling the phase difference value and optical axis direction. For example, by arranging a polarizer, viewing angle control film, ⁇ /2 wavelength plate (the axis angle is 45 degrees off from the orientation direction of the polarizer), and viewing angle control film, light can be blocked in all directions. This makes it possible to control the viewing angle so that light is transmitted only in the front direction.
  • the retardation layer 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 optical properties, mechanical properties, and manufacturing suitability from the viewpoint of reducing the thickness of the viewing angle control system. Specifically, it is preferably 1 to 150 ⁇ m, and The thickness is more preferably 70 ⁇ m, and even more preferably 1 to 30 ⁇ m.
  • 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 VA (Vertical Alignment) mode, OCB (Optically Compensated Bend) mode, IPS (In-Plane-Switching) mode, or TN (Twisted Nematic) mode. It is not limited to these.
  • VA Vertical Alignment
  • OCB Optically Compensated Bend
  • IPS In-Plane-Switching
  • TN Transmission Nematic
  • rod-like liquid crystal molecules are substantially horizontally aligned when no voltage is applied, and are further twisted 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 numerous documents.
  • VA mode liquid crystal cell rod-like liquid crystal molecules are aligned substantially vertically when no voltage is applied.
  • VA mode liquid crystal cells include (1) narrowly defined VA mode liquid crystal cells in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied, and substantially horizontally when voltage is applied (Japanese Patent Application Laid-Open No. 2002-2002); In addition to (2) a multi-domain (MVA mode) liquid crystal cell (SID97, described in Digest of tech. Papers (Proceedings) 28 (1997) 845) in which the VA mode is multi-domained to expand the viewing angle.
  • VVA mode multi-domain liquid crystal cell
  • n-ASM mode Liquid crystal cell in a mode in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied, and twisted and multi-domain aligned when a voltage is applied
  • SURVIVAL mode liquid crystal cell presented at LCD International 98.
  • PVA Plasma Vertical Alignment
  • Optical Alignment optical alignment type
  • PSA Polymer-Sustained Alignment
  • the liquid crystal compound In an IPS mode liquid crystal cell, the liquid crystal compound is oriented substantially parallel to the substrate, and when an electric field parallel to the substrate surface is applied, the liquid crystal molecules respond in a planar manner. That is, the liquid crystal compound is oriented in-plane when no electric field is applied.
  • a black display occurs when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are perpendicular to each other.
  • a method of using an optical compensatory sheet to reduce leakage light during black display in an oblique direction and improve the viewing angle is disclosed in JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522.
  • the organic EL display device preferably includes, for example, the above-described circularly polarizing plate and the organic EL display panel in this order from the viewing side.
  • the base material, the light absorption anisotropic film, and the ⁇ /4 plate are arranged in this order from the viewing side.
  • an organic EL display panel is a display panel constructed using an organic EL element in which an organic light emitting layer (organic electroluminescence layer) is sandwiched between electrodes (between a cathode and an anode).
  • the structure of the organic EL display panel is not particularly limited, and a known structure may be employed.
  • Example 1 [Formation of alignment film P1]
  • the surface of a cellulose acylate film (TAC base material with a thickness of 40 ⁇ m; TG40 manufactured by Fuji Film Co., Ltd.) was saponified with an alkaline solution, and the following composition for forming an alignment film 1 was applied thereon using a wire bar.
  • the cellulose acylate film 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.
  • rubbing treatment (roller rotation speed: 1000 rotations/spacer thickness 1.8 mm, stage speed 1.8 m/min) was performed once to obtain a film with an alignment film P1.
  • the thickness of the alignment film P1 was 1 ⁇ m.
  • composition 1 for forming alignment film ⁇ Modified polyvinyl alcohol PVA-1 3.80 parts by mass IRGACURE2959 0.20 parts by mass Water 70.00 parts by mass Methanol 30.00 parts by mass ------------------------ ⁇
  • composition 1 for forming light-absorbing anisotropic film Liquid crystal compound L1 2.716 parts by mass Liquid crystal compound L4 1.195 parts by mass Dichroic substance Y1 0.163 parts by mass Dichroic substance M1 0.109 parts by mass Dichroic substance C1 0.625 parts by mass Surfactant B1 0.003 parts by mass N-oxyl compound T1 0.054 parts by mass Polymerization initiator I1 0.136 parts by mass Tetrahydrofuran (THF) 9.500 parts by mass Cyclopentanone (CPO) 85.500 parts by mass ------ ⁇
  • barrier layer BA1 The following barrier composition BA1 was continuously applied onto the light-absorbing anisotropic film 1 using a wire bar. Next, it was dried at 80° C. and irradiated for 2 seconds at an illumination intensity of 200 mW/cm 2 using an LED lamp (center wavelength 365 nm) to obtain an optical film 1 on which a barrier layer BA1 was formed. The thickness of the barrier layer BA1 was 1 ⁇ m.
  • Orientation degree: S ((Az0/Ay0)-1)/((Az0/Ay0)+2)
  • Az0 represents the absorbance of the light absorption anisotropic film for polarized light in the direction of the absorption axis
  • Ay0 represents the absorbance of the light absorption anisotropic film for polarized light in the direction of the polarization axis.
  • the layer structure other than the light-absorbing anisotropic film 1 of the optical film 1 is Since it has no absorption in the wavelength range of 400 to 700 nm, the degree of orientation calculated above can be read as the value of the light absorption anisotropic film 1 included in the optical film 1.
  • Examples 2 to 9 and Comparative Examples 1 to 2 The procedure was carried out in the same manner as in Example 1, except that the type of composition for forming a light-absorbing anisotropic film was changed to the composition shown in Tables 1 and 2, and the type of alignment film was changed as shown in Table 2.
  • Light absorption anisotropic films and optical films of Examples 2 to 9 and Comparative Examples 1 to 2 were produced and evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • the evaluation of the degree of orientation using the optical film of Example 6 was carried out by changing the wavelength range for calculating the degree of orientation to 400 to 580 nm.
  • the evaluation of light resistance (evaluation 1) using the optical film of Example 6 was carried out by changing the wavelength range for transmittance measurement to 400 to 580 nm.
  • a method for forming the alignment film P2 is shown below.
  • the following composition 2 for forming an alignment film was applied onto a cellulose acylate film (TAC base material with a thickness of 60 ⁇ m; TG60 manufactured by Fuji Film Co., Ltd.) using a wire bar.
  • the cellulose acylate film on which the coating film was formed was dried with warm air at 140° C. for 120 seconds to form an alignment film P2.
  • the coating film was irradiated with polarized ultraviolet light (10 mJ/cm 2 , using an ultra-high pressure mercury lamp) to obtain a film with a photo-alignment film.
  • the thickness of the alignment film P2 was 1.7 ⁇ m.
  • Surfactant In the formula, Ac means an acetyl group. Also, the numerical value attached to the repeating unit represents the mass ratio.
  • N-oxyl compound (MW means molecular weight)
  • Polymerization initiator I1 (IRGACUREOXE-02, manufactured by BASF)
  • Example 10 The light-absorbing anisotropic film 10 and optical film of Example 10 were prepared in the same manner as in Example 1, except that the type of composition 1 for forming a light-absorbing anisotropic film was changed to the composition shown in Tables 1 and 3. 10 were produced.
  • CR0 Tm0/Tm30
  • the optical film 10 was set in a light resistance tester (IIIN-500W manufactured by Eagle Engineering Co., Ltd., XENON LAMP POWER SUPPLY XB-50101AA-A manufactured by USHIO Co., Ltd.) so that the xenon light was incident at an angle of 60°. Xenon irradiation was performed for 40 hours.
  • the contrast (CR) of the optical film 10 after the light resistance test was measured in the same manner as the contrast (CR0) before the light resistance test, the contrast reduction value ( ⁇ CR) was calculated using the following formula, and evaluated using the following criteria. did.
  • the results are shown in Table 3.
  • ⁇ CR
  • Examples 11-12 and Comparative Example 3 The light absorption anisotropy of Examples 11 to 12 and Comparative Example 3 was obtained in the same manner as in Example 10, except that the type of composition for forming a light absorption anisotropic film was changed to the composition shown in Tables 1 and 3. A film and an optical film were produced and evaluated in the same manner as in Example 10. The results are shown in Table 3.
  • the light absorption anisotropic film of the present invention was shown to have excellent light resistance (Examples 1 to 12).
  • the light absorption anisotropic films not containing the compound represented by formula (T) were shown to have insufficient light resistance (Comparative Examples 1 to 3).
  • Example 2 and Example 6 if the dichroic substance contains the compound represented by formula (1), a light absorption anisotropic film with better orientation and light resistance can be obtained. This was shown (Example 2).
  • Example 1 and Example 2 when a compound having a molecular weight of 500 or more is used as the compound represented by formula (T), a light absorption anisotropic film with better light resistance can be obtained.
  • Example 2 Furthermore, from a comparison between Example 2 and Example 5, when a compound having two N-oxyl radicals in one molecule is used as the compound represented by formula (T), an excellent light absorption difference is obtained due to the degree of orientation. It was shown that a tropic film could be obtained (Example 2).
  • the composition 1 for forming a light-absorbing anisotropic film was filled and the surrounding area was sealed. Thereafter, it was heated on a hot plate at 140°C for 30 seconds, cooled to room temperature (23°C), heated at 65°C for 60 seconds, and cooled again to room temperature. Thereafter, the liquid crystal cell 1 was produced by irradiating for 2 seconds using an LED lamp (center wavelength: 365 nm) at an illuminance of 200 mW/cm 2 . Using the obtained liquid crystal cell 1, light resistance was evaluated in the same manner as in Example 1. The results are shown in Table 4.
  • a liquid crystal cell 2 was prepared in the same manner as in Reference Example 1, except that Composition 2 for forming a light-absorbing anisotropic film was used instead of Composition 1 for forming a light-absorbing anisotropic film, and the same procedure as in Reference Example 1 was carried out. Light resistance was evaluated using the method described below. The results are shown in Table 4.

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Abstract

La présente invention aborde le problème consistant à fournir : un film anisotrope d'absorption de lumière ayant une excellente résistance à la lumière ; et un film optique et un dispositif d'affichage le comprenant. Un film anisotrope d'absorption de lumière selon la présente invention comprend un composé de cristaux liquides, une substance dichroïque et un composé représenté par la formule (T), les états d'alignement du composé de cristaux liquides et de la substance dichroïque étant fixés. Dans la formule (T), Lt représente une liaison simple ou un groupe de liaison nt-valent, Qt représente -C(Rt2)2-, une pluralité de Rt1s représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1-C12 qui peut avoir un substituant, une pluralité de Rt2s représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1-C12 qui peut avoir un substituant, mt représente un nombre entier de 0 à 2, et nt représente un nombre entier d'au moins 2.
PCT/JP2023/029565 2022-08-23 2023-08-16 Film anisotrope d'absorption de lumière, film optique et dispositif d'affichage WO2024043149A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080059057A (ko) * 2006-12-22 2008-06-26 주식회사 엘지화학 편광막용 이색성 염료, 이를 포함하는 경화성 편광막조성물 및 이로 형성된 편광막을 갖는 편광판
JP2009145776A (ja) * 2007-12-17 2009-07-02 Nitto Denko Corp 視角制御システムならびに画像表示装置
WO2017170036A1 (fr) * 2016-03-31 2017-10-05 富士フイルム株式会社 Composition colorée, film anisotrope absorbant la lumière, produit stratifié, et dispositif d'affichage d'image
JP2019191507A (ja) * 2018-04-27 2019-10-31 富士フイルム株式会社 光吸収異方性膜、積層体、積層体の製造方法および画像表示装置
WO2022138555A1 (fr) * 2020-12-21 2022-06-30 富士フイルム株式会社 Film anisotrope absorbant la lumière, système de commande d'angle visuel, et dispositif d'affichage d'image
WO2022138504A1 (fr) * 2020-12-21 2022-06-30 富士フイルム株式会社 Film optique, système de commande d'angle de vision, et dispositif d'affichage d'images

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080059057A (ko) * 2006-12-22 2008-06-26 주식회사 엘지화학 편광막용 이색성 염료, 이를 포함하는 경화성 편광막조성물 및 이로 형성된 편광막을 갖는 편광판
JP2009145776A (ja) * 2007-12-17 2009-07-02 Nitto Denko Corp 視角制御システムならびに画像表示装置
WO2017170036A1 (fr) * 2016-03-31 2017-10-05 富士フイルム株式会社 Composition colorée, film anisotrope absorbant la lumière, produit stratifié, et dispositif d'affichage d'image
JP2019191507A (ja) * 2018-04-27 2019-10-31 富士フイルム株式会社 光吸収異方性膜、積層体、積層体の製造方法および画像表示装置
WO2022138555A1 (fr) * 2020-12-21 2022-06-30 富士フイルム株式会社 Film anisotrope absorbant la lumière, système de commande d'angle visuel, et dispositif d'affichage d'image
WO2022138504A1 (fr) * 2020-12-21 2022-06-30 富士フイルム株式会社 Film optique, système de commande d'angle de vision, et dispositif d'affichage d'images

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